I had loved wearing girly clothes from the age of 3. I was the second son in a group of 4 brothers. My mom and Dad always told friends that I was supposed to be a girl. That kind of remark really screwed me up. As i grew older, i was small, thin, and had big brown eyes.
In elementary school, the girls decided that i would look good in tights. I found it embarrassing but at the same time, exciting. I didnt do anything about it but one of my friends heard there comments. A few days later, he asked me if he could fuck me. I was frightened by that, but I was also turned on by it. His name was Greg and his sister was a cheerleader a couple of years older.
Greg kept pestering me about it and I kept thinking about it. Finally, I told him I would have sex with him if he would let me dress in his sister’s clothes. I was really excited about the possibility even though I had never had any sexual attraction with boys.
A week later, Greg invited me over to his house while his parents were away with his sister. When I got there, I went thru Greg’s sisters sexy stuff. I didnt plan on actually having sex with Greg but I wanted to wear real girls clothes.
I took a shower and suggested Greg do the same. While he was showering, I went to Kay’s room. I found a sexy nighty on her bed that she had worn the night before. It smelled so sexy that my cock got hard. I put on the panties and the babydoll top and didnt notice that Greg had got out of the shower and was standing, naked, in her doorway.
Greg said I was really pretty. I guess I blushed. He wanted to have sex immediately but I got him to calm down, since I didnt want to waste this opportunity.
I asked Greg if there were any other things that I might wear. Greg said his Mom, who was very sexy, had worn a really hot French maid costume for Halloween. We went to her bedroom and Greg helped me find the outfit. I sent Greg downstairs to wait.
I found some sexy crotchless panties, black thigh high nylons, garter belt, and frilly slips. I had tried my hand with my Mom’s makeup in the past, so it was nothing new to me. I put on makeup, probably a little too much but I liked it. I had found the sexy wig Greg’s Mom had worn and brushed it out. I put on the sexy black French maids dress, the wig and then a pair of black 4 inch high heels.
I checked myself out in the mirror. I could feel the fabric of the frilly slips against my hard cock. I walked out and down the stairs. Greg was sitting on the couch when he saw me. Greg stammered that I was beautiful and stood up to expose his hard cock.
I walked over in front of Greg and I took his hand and placed it on my ass. Greg tried to kiss me but I turned my head. It felt great to be a girl. Greg continued to stroke my ass and I found myself becoming aroused. I turned and Greg and I awkwardly kissed. Damn, it felt great.
We ended up hugging and kissing and as we both got turned on. Greg kept saying that he wished his friends could see me. I told him that wasnt a good idea. Finally, I felt Greg’s hands pushing me down on my knees. I complied and found Greg’s hard cock inches from my face. Greg told me to suck it. His cock was really pretty with a pronounced head.
I dont know how or why it happened but the next thing I knew was Greg’s hard cock was in my mouth and I liked it. He was moaning and holding my head and was gently fucking my mouth. Oh, I liked that, hearing his pleasure, knowing that I was pleasing him like a girl would. Suddenly, Greg shuddered and he pulled me close and began to cum. He pu.ped a huge load down my throat and I liked that too.
Greg pulled his cock out of my mouth and I kissed it, stroked it, and suddenly, it was hard again and I sucked him again. It was nice to be that young.
We spent the day playing around with Greg begging to put his cock in me. I told him I was a virgin and wasnt sure. Greg said his Mom had a bunch of sex toys if I wanted to try some. I said that it might be OK. He got her secret box of lotions and pens shaped toys. I layed across Greg’s lap and he applied lotion to my bottom. I must admit that it did feel great to have him fingering my ass. Then, he switched to one of the vibrators. I had never experienced this but as Greg slowly slid it in and out of my butt. Greg found a bigger dildo and fucked me with that, then back to an even bigger vibrator. He slid that monster into me and i dont know what he touched but i suddenly began to cum, unlike anytime in my life. I turned to Greg and just said, “Fuck me.”
Greg obliged and he fucked me 3 times, right thru my crotchless panties. This was turning out better than I had ever dreamed. Greg finally said he couldn’t fuck anymore but I wanted more. He asked if he should call his friends and I said, “Please.”
Our friends showed up, not knowing who i was. Greg said i gave fantastic head and had a super tight ass. Before i knew it, i had a nice hard cock on my mouth. I sucked until he came then took another. As the night went on I gave my body to these guys. About midnight, the front door opened and there were Greg’s parents and sister. Greg’s Mom was furious and told me to get out. I stammered that my clothes were upstairs, but she said to get out and I could wear my faggot clothes. She pushed me out the door, looking like a whore. I was frightened. It was a mile to my house. I began the long walk thru the darkness.
I was almost home, having ducked out of site several times. The last quarter mile, there was no place to hide, but I had to get home. As I was walking the last way, I heard a car come slowly and stop. A nice looking guy in his 30s asked if I needed a ride. He persisted and I climbed into the car with him. I was nervous but figured he was harmless.
As we sat there, he said, " you’re not a girl are you?" I started to cry and he said it was OK and he understood. He asked me if I wanted to tell him how I ended up dressed the way I was. We pulled into a little park across the road from my house and i told him my story. I felt better after sharing with him. He said he better let me off there, rather than pulling i to my driveway. We got out of the car and standing there in the dark with him, he gave me a nice hug. I found myself kissing him and he kissed back. He was much better than Greg, and I enjoyed making out with him. My hand found his hard cock in his pants. I stroked it, unzipped his pants and pulled his cock out. I knelt down and let him slide his cock into my mouth. I loved his cock, loved the feel of its head against the back of my throat. He suddenly came, pulling his cock out until it was resting on my tongue. My friend said he wanted to see me swallow his cum, which h I did. That obviously turned him on. He pulled me to my feet and kissed me again, his tongue probing to taste his own cum. As we were doing this, I felt his hand slide between my legs, over my cock and onto my ass. He moaned and said I was incredibly wet. I asked if he wanted to fuck me and he picked me up, holding me by my legs and his cock found my hot, wet, cum-filled ass and he fucked me. He bent me over the fender of the car and pounded my ass furiously. When I felt him cum, I also came.
I kissed him goodnight and walked to my house, sneaking in my bedroom window. This had been my introduction into gay sex, and I liked it. Being able to dress like a sexy girl made all the difference. I was a slut when dressed but not interested in guys unless i was dressed. My life changed after this.
After my first gay experience that I listed here, I continued to dress in secret. When school started again, I had expected to get together with Greg, but it never happened. He got a girlfriend and I was out of the picture. I wondered if he thought about how it felt when I sucked his cock or let him fuck me with it. I never knew.
After high school, I moved to a little town about 60 miles away. I got a second story apartment with a balcony. It was an older house, but very quiet. One of the first thing I did was pull out the Penneys catalog I had “borrowed” from home. Since I had purged my clothing collection several times, trying to stop dressing, I needed some stuff.
The first thing i did was shower and shave my legs. I was only 5’6", still thin, weighing 128 pounds. I didnt have much body hair but I absolutely loved being silky smooth. I sat down and spent the afternoon ordering new high heels, bra and panty sets, negligee, cute blouses, a few mini dresses, all of the sexy stuff I desired. I even ordered a makeup kit and a long sexy wig in dark brown. It had cute bangs and I was excited.
It took 2 very long weeks before my package arrived. In the meantime, I had discovered that one of the other renters was a young school teacher, very cute lady, but she had a boyfriend and I was probably 10 years too young for her. But we shared the laundry room. I think the second night I was there, I found her clothes in the dryer. I loved wearing clothes that I knew had been worn by pretty women. Anyway, while digging thru the stuff in the dryer, I found a cute pink babydoll nightie with matching panties. I couldnt help myself, I stuffed my find under my shirt and rushed back upstairs so I didnt get caught. I know she probably wondered what happened to her so y sleepwear but I never confessed.
I took her sexy nightie upstairs and laid it out on the bed. I nervously undressed and slipped on the tiny panties, feeling my cock stretch the silky fabric. I slipped into the cute top and let my hands glide over the material. I decided to put my boy clothes over the top and run to the little strip mall up the road.
I strolled past the various stores, checking out the reflections of my hard cock stretching my Levi’s. I went into a department store and started looking at makeup. I picked out an eyeliner pencil and some cheap mascara and took the items to check out. I also picked up a car magazine, some chips, and a couple of candy bars, thinking that the checker wouldnt notice the makeup. It didnt work and the lady held up the 2 items a d asked, “Are these for your Mom?”, and I said, no, my sister. She said there were better brands for less money and went over to get them. She rang me up and said, " I think you’ll like these better" and smiled at me as I took my bag and left.
I got home right after dark, got dressed and put on my eyeliner and mascara. My hair was long enough to irritate my Dad, so I tried to arrange it as feminine as I could. I felt really sexy and I went out onto my covered porch. I knew nobody would look up there as they drove by, but it was still a little scary. This caused my cock to harden again and I pulled it out of the sexy panties. I slowly stroked it for a long time, stopping only to delay that orgasm I knew was coming. Suddenly, I came and was shooting a huge load of cum thru the rail and into the flower bed by the front steps. Just then, the school teacher came around the corner, headed for the steps. I was afraid to move and continued to let my cum drip into the flowers. I was afraid she had seen me but she didnt seem to notice. I guess the thrill of almost being caught by a pretty woman was a whole new fantasy.
My purchase from Penneys finally came and I played out my new girl things. I probably jacked off 3 or 4 times while wearing the high heels. I loved high heels and these black sandal toed 4 inch heels were perfect. I went out on the porch wearing only the sexy heels and masturbated down into the flower bed, wondering what the young teacher would think. That turned me on.
It took a while, but the next week I finally got the nerve to go out for a drive in my old pickup. Not too sexy but I figured no one would ever notice. Since I was not going to see anyone, I did a really subdued job with my makeup, eyeliner, mascara, some blue eye shadow, and some pale lipstick. I didnt bother with the wig, not wanting to be too noticeable. I wore some black tights and a black leotard, with a black turtle neck over the top, and finished off with the sexy black high heels. I put on some green slacks over the top so I could get to my truck.
I was really scared as I went out to my truck, walking past the infamous flower bed. I pulled out of the driveway and went out along the river. It was dark and quiet as I pulled into a small county park. I stopped and got out to take off my pants. I climbed back in and felt the cool vinyl under the fabric under my tights. I got a little braver as I drove toward town. I stopped at the first light and looked down at my legs, so sexy in the tights. Nobody seemed to notice me as I drove. I headed out to the deserted college.
I pulled into the parking lot and got out, imagining what the other students would think if i did this during the day. Mmmm, so exciting. I took my pants with me, just in case. I played them over the tailgate and walked down one of the paths towards the classrooms. I was enjoying myself when some guy yelled at me that this was a closed area. It was a shock to be seen, even at a distance in the dark. I hurried back to my truck, hopped in and left as fast as i could. Damn, that was close.
Coming into town, my truck engine shuddered and shut off. The gas guage was not always working right, so i carried 5 gallons of gas in the bed. No problem, at least until i realized my pants were missing. Shit, this “was” a problem. J had coasted to the curb, which was OK. What wasnt OK was the fact the filler was on the street side and i was wearing tights and high heels. Problem. I sat there for quite a while trying to think of a solution. Only one came to mind, wait until the traffic was clear, jump out and pour the gas in. And hope nobody came by. No choice. Had to do it.
I slid out of the cab, checked down the road, found it clear and grabbed the gas can and started pouring. Just then, i saw lights approaching. But before i could get the empty gas can into the back of the truck, the car stopped behind me. Good news, it wasnt a cop, a young guy in a van. He hopped out and asked if I needed help as he ran up to me. There I was, in tights and a leotard and in high heels.
He told me he saw my legs first and then the high heels. He let me get into the truck but kept the door open. He asked me if I was a guy and I nervously said yes, to which he said, “Cool”. He asked me where I was going dressed like the way I was. I told him I was just out for a drive. He asked if it turned me on to be out in public dressed like a girl? He ad.itted that at first he thought I was a girl, a very cute girl. He said I had sexier legs than most of the girls at the college. I blushed.
He asked if I wanted to get off the main drag and go someplace more secluded. I said that would be nice. I followed his van down to a park by the Veterans Hospital. I pulled in next to him, my heart pounding as I walked around to his van. As I stood there, he just looked at me. He said, “Are you sure you’re not a girl?” We both laughed. He asked if it turned me on to be with a guy in the dark. I told him there were lights along the path, so it wasnt that dark.
We walked down the path, just talking. I accidentally stumbled but the guy caught me. His hand had slid down my back and I could feel it cupping my ass. But it was nice to be close to him. His name was Tom and I remember thinking he was pretty cool.
He asked me about my history, so I told him about how I had gotten to where I was. I told him about my parents saying that I was supposed to be a girl and how, when the toy catalogs came, my brothers wanted the soldier costumes and i secretly wanted the ballerina outfit. He laughed. I told him about the girls telling me i would look great in tights and i was too cute to be a boy.
Tom said the girls were definitely right, on both accounts. He was really interested in my adventure with Greg. As I told about it, I could tell he was very getting turned on. Greg told me that I definitely looked like a sexy girl and I thanked him, and on a lark, I gave him a hug and he hugged me back, again taking the opportunity to hold my butt with both hands. I pulled back and asked him if I could su k his cock. This was a surprise to him I guess, but he said I could if I really wanted to. I told him I really wanted to.There was a park bench next to us, so I sat down and pulled Tom closer, dropping his pants as he got closer. His cock was really nice, not too big, just right with a big mushroom head like I liked. I took his cock into my mouth and enjoyed the feeling of his warm cock as I sucked. I’m not sure how long the blowjob lasted but he finally started to pull out of my mouth. He said he was coming, so I told him I wanted his cum a d slid my mouth back over his cock. I could feel him as he tended up and began cumming in my mouth. I continued to suck, pulling cum from his balls. I guess he really liked it because as I was continuing to hold his co k in my mouth, he said that the blowjob was fantastic. He said it was the best he ever had. But I didnt release his co k and kept sucking until I felt him getting hard again. It took a little longer, but he c finally came again.
We walked back to his van and when we got there, i thanked him for letting me suck his cock. He laughed again. I asked if he would want to fuck me and he said if i fucked as well as i sucked cock, he was willing, but added he didnt think he had anything left that night. We both laughed. He asked me about my story and about what turned me on about having sex with a bunch of guys. I told him that i guessed i was a slut when i was dressed in sexy things. He said that was true, i was a fantastic whore.
Tom suggested that if i wanted to play again, he would like to meet pick me up and take me to the Friday night cruise. He said he’d like to see me in something really sexy. I said sure, and gave him my address. I had my own stud!
A few days after meeting Tom, he called and wanted to know if we were still on for Friday night. I told him I was very excited about being nasty with him. He asked if I was serious about meeting some of his friends and told him I was definitely serious. He asked if he could come over in a little bit and I said that would be great.
I quickly cleaned up and shaved, to be nice and smooth for him. I even touched, just in case and carefully filled my ass with K-Y jelly, hoping Tom was serious about fucking me. Better to be prepared than not. I put on my makeup, wanting to be as sexy as possible for my new guy.
Tom knocked on my door and I opened it for him. He looked at me and said I was even prettier in the light. He came in and I hugged him and kissed him gently, which he returned a little more passionately. I was wearing a long sleeved white peasant blouse over black bikini panties and my high heels.
We sat on the bed and talked about my experiences since I had moved to the apartment. We laughed and talked for a couple of hours. He liked the story of me stealing the teachers pink babydoll nightie. He also like the story of me standing on the porch jacking off.
Tom asked me if I would get naked, except for the 4 inch heels and step out onto the porch. I asked him, “Really” and he said he would like to see me that way. So I agreed, taking off the top then the panties. I stepped closer to Tom and he kissed me again while fondling my bare bottom. Mmmm, this felt so good. Then he bent to kiss my nipples which was also a turn on. He turned me around and pushed me towards the door to the porch. I stepped out, enjoying the cool evening air on my silky body. My cock immediately got hard from being naked in public. Just then, Tom stepped up behind me. I felt his warm and naked body against me. I could feel his cock hardening between my legs. I turned to embrace and kiss him, then dropped down to his hard cock. I opened my mouth to accept its mushroom head and began to suck him. Cars were driving by in the darkness, nobody imagining what was going on in my apartment. This thought turned me on and I sucked him faster, pulling his cock as far into my mouth as it would go, until his balls were against my chin. Tom moaned softly and began to gently fuck my mouth. He came shortly, filling my mouth with his hot cum. I pulled my mouth off his cock and stood up. I opened my mouth to show him my mouthful of cum, then I swallowed it all, then kissed him again.
Tom hugged me, groping my ass as he did. He said, “You are all juicy back there.” I asked if he wanted to fuck me and I turned around and bent over the rail, spreading my legs as I did. Tom stepped up behind me, hard again, and slowly pushed his cock into the moistness of my horny ass. Oh, it had been such a long time since I had been fucked that I enjoyed every inch of my lovers cock. Tom was fucking me deeply and my cock was ready to explode.
Just then, the school teacher appeared at the corner of the house, heading to the front steps. I knew we should stop but I didnt want to. Tom continued fucking me as I watched my neighbor start up the steps. At that point, I just lost it and began to cum like I never had, gushing load after load out and down into the flower bed. But no one apparently noticed and Tom suddenly came, filling my ass with more cum. I liked having cum in my ass, so wet and slippery.
Tom got dressed and kissed me before leaving. I sat in my apartment, relishing the evenings fun. But just then, someone knocked on my door. Shit, I was still in makeup and high heels. I pretended to not be there but a feminine voice said,“I know you’re in there. This is your neighbor and I’m not leaving until you open the door.” So, I slowly cracked the door and she asked to come in. I told her I wasnt dressed and she said she was quite aware of that fact. She then told me she had seen me and my boyfriend on the porch, having sex. She handed me a bag and said there were some things I could have, mostly old lingerie she no longer wore. She said when cars came by in front of the house, she saw me with the guy, clearly naked and clearly having sex. She said that was a good way to get arrested and to just be careful. Then she went back to her apartment.
I opened the bag and dumped out the contents. There were panties and bras, several negligee, a garter belt and 3 pairs of thigh high nylons. In the mix was a long white box, I opened it to find a large life-like vibrator. There was a note saying, “Have fun!”
I put the fake cock to my lips, imagining that this had been in the sexy teachers pussy. I slid it deep into my mouth, all 10 inches of it. I gagged a few times but I finally got it all the way into my throat and as I fucked my mouth with it, I stroked my cock to another orgasm. I was having fun with it, just like the teacher said.
I put on the pink nightie top and went to bed with the teachers toy, turning on the vibrators buzzing shape. I drifted off to sleep being fucked by her toy, imagining what she would think of her faggot neighbor………
The rest of the week was a blur. I gathered up what I was going to wear. Things were complicated by the fact that I was constantly playing with the huge vibrator that the pretty teacher had given me, either practicing my deep throat skills or fucking my ass with it.
Friday night arrived and Tom called to tell me he’d be by at 8:00 to pick me up. I took a long shower, shaved my legs again, then douched and used my K-Y jelly in preparation for some serious ass fucking.
I dressed in the teacher supplied black garter belt, thigh high sheer black nylons, black bikini panties that I carefully split the crotch open, to allow easy access to my tender ass. I slipped into my sexy black high heels and then sat down to do my makeup. I went for a slightly sluttier look, with heavier eye shadow. I topped everything off with a long dark brown wig I had ordered. I decided to wear a very short black velvet mini dress with long puffy sleeves. Once satisfied, I stepped back onto the porch, to my favorite spot and slowly massaged my cock until I shot cum back into the flowerbed. I was now ready to go out with Tom and his friends.
I saw Tom pull in and went downstairs to meet him. I had forgotten about the teacher, who happened to be sitting on the lower porch. I didnt see her at first, but she scared me when she asked,“Got a hot date, honey?” I just smiled as I went by and she remarked,“Must be a lucky guy with that sexy outfit” That was encouraging.
Tom was standing by his van when I got there. He just said, “Damn, you look awesome.” He helped me step into the van, making sure he could fondle my ass again.
We drove into town and stopped at a group of vehicles in front of an alley. Kids were wandering around, joking and doing what young college kids do. Tom helped me out of the van, which was the base for much of the nights activities.
Tom introduced me to his curious friends, welcoming me to their group. Tom and I were making out while people watched, with him lifting up my dress to expose my bare thighs above the nylons. That was making me very hot. I wanted to suck Tom’s cock or to have him fuck me, right there by the van.
I whispered into Tom’s ear that I wanted his cock, then I nibbled his ear lobe. I sat down in the slider side door and pulled Tom’s cock out. With 6 or 7 guys watching, I began to suck my first cock of the night. I sucked Tom’s cock like I had sucked the teacher’s vibrator, deep throating his marvelous cock. He shot a load of cum into my mouth, which I showed our audience. Tom asked, “Who else wants the best head they ever had,” and I soon had another erect penus between my lips.
I sucked any of Tom’s friends that were willing, which turned out to be all of them. A couple of girls came by and watched and one of them asked how they were supposed to compete with a slut like that. Tom said it would be tough, because I wasnt even a girl. The girls stepped up closer to see what I was doing. I finished the cock I was one, pulled back and opened my mouth to show them the load of cum on my tongue. I swallowed, opened my mouth to show them the cum was down my throat. I looked at them and said,“i like cum.” One of them said, “it looks like it, bitch.” I just smiled.
Some new guys showed up after hearing what was happening by the van. I sucked some more cock, ate some more cum, this was being a great night. More girls were there watching and making sexy comments as I satisfied the growing group.
Then I heard Tom ask if anyone wanted to see his “girlfriend” fucked. It sounded like a football game from the whistling and yelling. Tom stepped up and helped me bend over into the van. With everyone watching, he flipped my short dress up over my waist, showing the garter belt and panties. I whispered they were crotchless and for him to ease his cock into me. He did as I instructed and began making love to my ass. He seemed to enjoy being watched as he co tuned to fuck me. He finally came in me and pulled out. Another guy took his place, then another, each depositing their hot cream in my ass.
I heard someone say ,“Hey, Sue is pulling a train a few cars up.” Wow I had gotten a girl so turned on that she was following my example. I knew I had fucked at least 30 guys but I wanted to watch this “Sue girl”. I pulled my dress down and took Tom’s arm th walk over.
Sue was a small, cute blonde and was really satisfying the guys. After watching her do 3 guys, there was a break in the action. She was completely naked in the back of somebodies Mama’s car. Someone pointed out her seriously cum-filled pussy. It looked so inviting and Tom said I should eat it. I had never been with a girl but I wasted no time getting between Sue’s legs. I could see the cum dripping from her sexy pussy and brought my lips to her tender lips. I kissed her pussy, I licked her pussy, the taste of all that cum driving me crazy. She had cum running down the crack of her ass and I ate that too. Sue was moaning loudly and the crowd was egging us on as I devoured her. When I had finished, Sue thanked me,saying she had never had an orgasm in her life. I pulled her out of the car and pulled her naked body close and we kissed. I had remnants of cum on my lips and tongue and I let her taste it. Without saying a word, Sue knelt in front of me and lifted my dress to expose my hard cock. She took my cock into her warm mouth and started sucking. I had almost forgotten we had an audience and found myself highly turned on. Then I came, one shot of cum after another. Sue took it all, then stood up and kissed me. She hadnt swallowed my come and she used her tongue to feed me my own cum. The crowd definitely liked that.
I had found people that liked what I did and the way I looked. I was happy.
After that Friday night, I had to take a few nights off to rest up. I spent a lot of time reassuring myself that it hadnt been a dream. I couldnt believe how the local kids responded to me, no name calling, no disrespect. It was just fun and honest sex.
One evening, my phone rang and a famine voice asked if this was Miki. She said she was at the Friday night event and watched me. She said she was a friend of Tom’s. She said she was into some slightly kinky stuff and thought that I might enjoy it. I told her to tell me more. She asked if she could come over and I said OK. She said she would like to see me in makeup and lingerie if I didnt mind. Oh, I didnt mind at all.
I did a quick shower, did my enama, put on my slutty makeup, black teddies with garters, black thigh thighs, and my black 4" high heels. I just brushed my hair around to look as feminine as I could. As I looked in the mirror, I couldnt help but get turned on. I then put a sheer black top that came with the teddie. Just then, there was a knock. I was wondering if Tom would be coming as I opened the front door.
Instead of Tom or the girl, my Mom was standing there. Oh, fuck! How would I talk my way out of this. Mom said, "Mike, is that you, what are you wearing? What are you doing? " I mumbled something about being in a play at school or something. I dont think Mom bought a y of my story as sheooked around the room, spotting the huge vibrator on the table. Then she just back ked out the door and said she’d just tell my Dad I wasnt home. Then she left. I was fucked.
A few minutes later, another knock. I asked thru the door who it was and I heard, “this is Tina, I just called”. I opened the door and there was the cutest little brunette I had ever seen. She came in and said that i was pretty careful about the door. I told her how my Mom had just been there and I had opened the door dressed like I was. Tina got a big kick out of that as she handled my vibrator. She said she wished she had been there because she would have come up beside me with the vibrator and slipped it up my ass as my Mom watched. I told her she was nasty and we both laughed.
Tina said she was big and loved having sex with girls and doing nasty things with sissy guys. I asked, “Like fucking guys with a huge vibrator in front of his Mom?” She said, “Yeah, stuff like that.” Damn, I liked this girl.
Tina had dark stockings, high heels, and was wearing a short black trench coat. She asked if she could take it off and I told her that was fine. She took it off to show she was wearing all leather lingerie. Damn, she was sexy. She asked if I liked taking orders from a dominant woman. I didnt ready know what she meant. Wrong answer! She told me to step outside on the porch. She said Tom had told her about fucking mouth there. We both went out and she instructed me to bed over the rail. I did as she said and she kicked my legs apart and slid the huge vibrator into my ass. As she fucked me with it, she said this thing is really big. She asked if I could take it all a d plunged it all the way into me, holding it there while she reached around to stroke my cock. I dont know what that vibrator touched, but within 4 strokes, I shot my cum out I to that poor flowerbed.
Tina kept fucking me with it, then left it in me, vibrating away. She said, “Come inside, I wa t you to eat me. I saw you eat Sue after she had pulled the train and that was so sexy. I only had 4 guys fuck me tonight but I think you will enjoy all of my cum.” She played back on the bed and pulled off her sexy panties, which were covered with cum. She demanded that I suck the cum off them. I did as instructed, enjoying the white, frothy cum. Then she said, “Eat me, you fucking faggot.” I do t know why, but having a sexy bitch tell me to eat her wet pussy and then calling me names. With the vibrator still massaging my insides, i came again. We ended up with Tina sitting on my face with her pussy dripping the remaining cum into my mouth. Tina just told me to eat all of the cum and if i did a good job, i could be her bitch. This was fantastic.
She told me to dress tomorrow evening and she would pick me up and show me a good time. I asked what i should wear and she told me the pink nightie would be fine, along with some pink high heels. I told her I didnt have any and she said, “Get some.” Then she left.
Where were we going? I guess it did t matter. I’d go anyplace with Tina. I wanted to be her bitch.
The next day, I got up and showered, shaved, put on some eyeliner, mascara, a tiny bit of pink eyeshadow and fluffed up my hair to look feminine but not over the top. I dressed in white lace bikini panties, my white long sleeved peasant blouse, and a pair of very short white Levi cutoffs, and a pair of white sandals.
I carefully snuck down the stairs and around my apartment to my old truck. Not much going on at that time of day. Tina had left orders for me to get some pink high heels and I wanted to please her. As I drove, I felt my cock edge it’s way down my left and push out of my panties. It was strange to drive with my cock exposed like that. I drove to a small strip mall where there were 2 shoe shops.
I left my truck and carefully made my way to the stores. As I walked to the first store, I noticed that most of the sales people were women, so I just looked in the windows and passed the place, too nervous to go in.
I walked to the other end and met a couple of guys coming towards me. I had tucked my cock back in and snuggled my panties up to hold it. I tried to walk as femininely as I could. I could feel the guys looking at me, but nothing was said.
As I approached the other store, all I could think about was pleasing Tina. I studied the display windows and to my delite, there was an extremely pair of sandal toed pink platform heels. The heels were probably 5 and a half inches with one inch platforms. Just what I needed.
I nervously walked in and the place was deserted. I picked up the pink high heel and was studying it when a male voice said, “Do yo want to try on a pair?” I turned and just nodded. He was an older guy, maybe 50, nice looking in a dorky kind of way. He said to sit down and he would check my size. Damn, I hadnt expected that and my hope had been to grab, pay, and go. He was polite and showed me to a seat. I put my foot on the measuring tool and he got the measure. He came back with a couple of boxes and helped me into the first pair.
As I watched him fasten the buckles, I became self conscious. He stood up and asked how they felt. He said to walk a bit, which I did while watching myself in the mirror. Damn, they really made my legs look sexy.
The salesman said they looked a little big and suggested I drop half a size. So, as I switched sizes, I noticed my cock trying to escape ed my too-short cutoffs. The more I tried to control my harden, the bigger it got until it was poking out in my lace panties. The salesman noticed immediately and I almost started to cry. He said, “it’s ok, it’s ok. You look great. Dont worry about it. The shoes look perfect.” I stood up, feeling better about myself and I walked around the store, again watching myself in the mirrors. I told the salesman I would take them.
I paid at the register and the salesman, who had been very professional, asked if I would be interested in some sexy stuff left over in stock from when the place had been a high end women’s clothing store. I told him I didnt have more money. He motioned me to come to the rear of the store, telling me that I could have whatever I wanted, since he was going g to be thrown out anyway.
He asked me about the way I was dressed and my attraction to high hes. I told him some of my story as he searched thru boxes. He asked," Would you be interested In some crotchless panties?". I blushed and said sure. He handed me a whole box of assorted panties, threw on some thigh high nylons that were hanging on a display. He said there were more things, lingerie, and other stuff. As he searched, I asked again about paying him. He just smiled at me and said if I’d model the crotchless panties for him, that was payment enough.
So, as he was finding more things, I stepped out of my cutoffs and panties and slipped on a pair of white crotchless panties. There was no place for my cock to hide, so it just stood out. The salesman came off the ladder and turned around. There I stood, showing him my ass under the peasant blouse. I walked down the aisle and turned to walk back. He was speechless and as I approached him, I turned and took his hand and put it on my bottom. I reached over and touched his hardening cock thru his slacks. I asked him if I could suck his cock, but he didnt answer. So I unfastened his belt and let his pants and boxer shorts drop down around his ankles. As he looked out thru the curtain, I kissed his cock which jumped at my touch. I took it into my mouth, enjoying the texture and feeling as it hardened. I slowly sucked him, trying to make it as pleasant and erotic for him as possible. I moaned as I sucked him, pulling his cock free to beg for him to cum in my mouth, to feed me his cum. I dont think his wife was much into giving head, just from his reaction. He finally quivered and came in my mouth. I pulled back and opened my mouth to show him his cum in my mouth. He just stared at me, so I hungrily swallowed his load and went back to su king his cock, trying to get every drop of his warm cum out of him.
About that time, a couple of women came in and he hurriedly pulled up his pants and went out to great them. I put on my cutoffs and decided to wear the pink heels home, knowing that no normal woman would dress that way. As I walked out, the 2 older ladies looked up at me. I smiled and told the salesman thanks for the panties. I told him I’d be back and I walked out the door, feeling like the slut I was. Tina was going to be happy with her faggot cocksucker. I didnt even notice if there were people in the mall as I headed for my old truck.
After my visit to the shoe story, I made it home without any problems. Of course, I still had to make it around my apartment without being caught. Stepping out of my truck, I had to look down at my new high heels and admire my sexy legs.
I went into my place and layed everything out just to see what the salesman had given me. I had taken off my top and my cutoffs and was wearing just the heels and the white lacy crotchless panties. I rubbed my flat chest and massaged my small nipples, feeling so sexy.
I sorted my new lingerie, finding a sexy light pink crotchless teddy with attached garters and some light pink thigh high nylons, not normally my color, but they matched the new shoes.
I then had the urge to step outside on the porch, in broad daylight, dressed as I was. I really didnt care who saw me. I was walking around, enjoying the coolness of the air and the freedom to be myself, when a male voice said, “Nice legs”. It was my mailman, a guy in his 60s. Since he had already seen me, I decided I would talk with him. I asked if he liked my new shoes, and he did. After a few minutes, I asked him if he wanted to see me do something kinky. He said sure, so, with traffic going by, I started massaging my cock and in a few minutes, shot a load of cum into my favorite flowerbed. He laughed and continued on his route.
I went inside and got cleaned up for the evening fun with Tina. I dressed in the pink teddy, slipped on the nylons, then my new shoes. I fixed my makeup, being careful not to go over the top and retain some of my boyish looks.
Tina showed up at 5:30 and I let her in. I modeled my new shoes and my new lingerie. She said I looked perfect. She was wearing her normal black trenchcoat over her leather dometrix lingerie. She handed me a light pink trenchcoat, like hers, only shorter. I put it on and i was ready for whatever she wanted to do. Before leaving, she asked if she could borrow my big vibrator, so i gave it to her.
We walked down stairs and discovered the teacher sitting on her porch. She asked, “Where are you 2 cute girls going tonight?” I blushed as Tina pulled out the vibrator and showed her, telling her we had big plans. She took th he vibrator and slid it between my butt cheeks and as we talked, my cock got hard and poked out of my short coat. The teacher said i should get that in out of the cold and Tina gently grabbed it and led me to her car.
I asked where we were going. She asked if i had ever been to the boys dorm at the college. She said there were 300 horny guys there and i might be able to get together with 20 or so. We parked in the lot and got out of the car. Tina told me to leave the coat there.
As we headed to the auditorium, we picked up a large group of guys playing softball and they followed us. I just smiled at them, trying to be sexy. Once inside, Tina led me up on the stage. She then addressed the group and asked if any of them wanted to see her with her faggot sissy, pointing at me. She said, “He sucks and fucks, if you’re interested.”
She told me to bend over a chair and spread my legs. I did as told and she slipped out of her coat, showing the crowd her sexy outfit. She took out a large brandy glass and told them that she would like to see it full of cum by the time she left. It disappeared into the seats. She then slid the huge vibrator into my ass, causing me to sigh deeply. She then fucked me with it while the guys watched.
She had me lay on a piano bench, on my back. Tina told them to step up and try her sissy. Two lines formed and i had guys fucking my mouth and my butt. It was nice to have the guys match their rhythm and fuck at the same time. I imagined their cocks touching deep inside, even though i knew it wasnt possible. I fucked and sucked for a long time, losing track of how many. Tina was leaning over the chair, taking several cocks into her pussy. It looked great.
Finally, when everyone was done, she asked if the 4 black basketball players were in and one guy said he’d go check. A few minutes later, 4 tall black guys walked in. Tina said hi to them, obviously knowing them. She told them she had brought a new faggot for them to fuck. They quickly stripped down, showing their cocks, one about 7 inches, 2 that were 8 inches, and the last that had a good 10 inches soft. One stepped up and noted to the others, "This faggot is full of cum, i think I’ll add my load to it. The audience cheered. The big guy stepped up to my face, still on my back. He told me to suck his dick. I opened my mouth and let him put his cock in. He began to get hard and told me to get ready for the biggest cock I had ever had. It was huge as it came to full erection and he forced it deep into my mouth. He pulled it out and shoved it in again. The guy fucking my ass came and was replaced by one of the others. The audience was going crazy as the black guys fucked me. The big guy pulled out and said he was ready to cum. I looked up and told him I wanted to eat his cum. He just looked at me, slid his cock in and came to a shuddering climax. I continued to suck, trying to suck his cum right out of his balls.
I looked at Tina and she smiled. She asked the audience if they wanted to watch me eat her cum-filled pussy while I got 12 inches of black cock up my ass. They cheered as the big guy lifted my legs up onto his shoulders a slid his huge cock into me. Tina stepped up over my mouth and dropped her juicy pussy onto my mouth. I was trying to eat all of the cum as it streamed out of her pussy. As the crowd yelled and whistled, the big guy suddenly came in my ass. Tima stepped away, I guess satisfied I had did a good job cleaning her.
She pulled me to my feet and while holding my wrist in the air, she asked if her faggot sissy had put on a good show, they cheered again. Then one of the guys stepped up on the stage, carrying the big brandy glass, about 3/4 full of cum. Tina held it up and told them they had done a great job. She then asked what she should do with it. Somebody yelled,“Make the faggot drink it”, and the group yelled out for me to drink it.
Tina handed me the big glass and said, “You heard them, bitch. Drink it. Drink all of the delicious cum and dont waste a drop.” I just looked at the glass of cum, then, put it to my lips and began to drink it. I could hear guys saying shit like that’s disgusting, gross, and a few other rather negative things. But, secretly, I wanted to drink it, to swallow the cum from all of these young guys. As I drank it, gulping it down hungrily, Tina’s hand took my cock and started stroking me. She told the guys that I obviously was the best cum but she ever had. As I emptied the glass of cum, I came in Tina’s hand. She brought it up to my lips and I started licking my cum off her fingers. I could feel cum running down my inner legs and Tina put my vibrator against my asshole , turned it on, and shoved it all the way in.
As we left, guys were telling Tina to bring me back. She said she would. Somebody handed her some pictures of me being fucked by the big black cock. She told him she might send them to my Mom if I ever disobeyed. I was her bitch, her fuck toy, her cum-slut. And I liked it.
On the way home, she asked if I had had a good time and I told her I had. I told her I had sure fucked and sucked a lot of guys. She said, “Yes you did, 112 guys by her count.” That was a lot.
I got home and went straight to bed, not even taking off my high heels. The vibrator was still buzzing away and every once in a while, I would cum. I licked my lips and tasted remnants of all that cum. I fell asleep, happy.
I woke up the next morning, laying there trying to remember everything from the previous day. It was like a dream, but I knew it wasnt. I tried to think of a good reason why I would have fucked and sucked so many guys. I couldnt. I guess my only reason was to please Tina.
I managed to pull the big vibrator out of my bottom, its batteries completely dead. I went in to shower and as I stood there, I spread my legs and let the cum drain from my body. I couldnt believe how much there was. I finished my shower and decided I better take a few days off from my recent activities.
In the afternoon, I got a call from Tina, checking on me. She asked if she could come over and I agreed. I dressed in a dark green babydoll nightie with matching panties. Tina showed up, wearing a cute top and Levi cutoffs, not her usual attire.
She had a large folder and she asked me if I wanted to see something cool. I said sure. She pulled out a stack of photos that she had enlarged from the day before. She eagerly showed me one of me on my back, with long lines waiting to fuck or be sucked. My cock twitched as i looked at the photo. She continued to go thru them. I guess my favorite was the one with the big black guy fucking me while Tina had been feeding me cum directly from her pussy. The final one was me holding the big brandy glass, drinking all that cum. Wow!
Tina said she had gotten a call from a friend at the college and she had been told how much the guys enjoyed it and wanted to know if we wanted to come back up. Tina asked me what I thought and I told her that I would if she wanted to. She told me that she had been extremely turned on watching me. She said she never dreamed anyone could do what I did. She said for her, watching me drink a quart of cum was hot. She asked if I would do it again and I told her I would.
Tina then stripped naked and pulled my panties off. She layed back and pulled me on top of her. She put her lips to mine and kissed me. We kissed and our tongues touched and Tina pushed me down between her legs and she ordered me to eat her. I spread her legs and my tongue pushed deeply into her velvety pussy. She pulled me up and her hand grasped my cock and guided it into her. We fucked for a while and I eventually came. Tina again pushed me down to her pussy and told me to eat her. I liked this girl. We layed together and talked. I told her my whole story, about my Mom and Dad telling friends I was supposed to be their daughter. She asked what they would think if they saw me fucking the huge black cock. I told her they wouldnt like it.
After Tina left, I didnt see or hear from her the rest of the week. By the weekend, I was getting really horny. I decided that I should go back and thank the shoe salesman and see if he had any more treasures. I dressed in all black lingerie and lit on the black velvet mini dress. I did my makeup and slipped into my long dark brown wig and black heels.
I drove to the mall and proudly walked to his store. He was with a customer and didnt pay too much attention. I went to the end of the store and watched him in the mirror until the lady left. I turned around and approached him. He didnt seem to recognize me until I asked if he remembered me. He blushed and said hi. I told him i said i was coming back. He thanked me and told me i was really sexy as a woman. I smiled at him and bent forward to get a gentle kiss.
He said he was glad i came back because he had boxed up the rest of the erotic clothes from the rear of the store. We stepped to the rear of the store and once behind the curtain, i lifted the back of my dress and asked if he thought i had a sexy bottom. He said it was fantastic as his hands started feeling my soft skin.
I knelt down and eased his cock out, and started sucking him again. I got him to quickly cum. I told him I wanted his cock in my ass and wanted to feel him cum in there. He started getting hard, so I pulled him out into the store. I bent over the counter and begged him to fuck me. He was a little nervous because we could see people walking past but he slid his cock into me. He whispered into my ear that my ass was so tight. His pace picked up and he began to fuck me faster and faster, his balls slamming into mine. Just then, a woman walked into the front door, took one look and backed out, obviously not comfortable with what she saw. My salesman came at that point and continued standing behind me with his cock draining his cum into me. I kissed him again and we collected the 2 boxes and he helped me carry them to my truck. At the truck, I secretly reached between my legs and ran 2 fingers into my as, covering them with his cum. I kissed him again and as I thanked him, I slid the 2 wet fingers into his mouth. I asked if I could come back. He just nodded.
I drove back home, happy with my day’s accomplishments.
For the next few days, I tried to catch up on school work. Because my activities had distracted me, I was seriously behind. Tina called a couple of times, wanting to find someone to play with, but I had to tell her I was playing catchup at school. She got mad at me and told me I was supposed to be her sissy slave. I told her I was but she didnt seem to believe me.
Finally, a couple of weeks later, she called and demanded that I be ready to go back to the dorm. Since I was super horny, I said I could do it. She was still mad and told me it was about time I perform my duties. She said that she had been thinking about what had happened when my mother showed up unexpectedly. I told her I was sorry for not being a good sissy. She let it go.
Tina came by and went thru my lingerie. She picked out a black garter belt, black thigh highs,black crotchless panties, a sheer black see thru top that was like a mini dress. She said I should go super slutty with my makeup, really go for the whorish look. I asked wig or no wig? She said, no wig this time.
She picked me up the next afternoon and drove me to the boys dorm. On the way, she said she was still mad because I had not done as I had promised. She said she had to teach me a lesson. So I’m thinking, “this should be fun.”
She said she had gotten ahold of her friends at the school and she was sure we would have a bigger turnout. A bigger turnout? Last time we had over a hundred guys.
Tina pulled in and parked and ordered me out. She was obviously irritated. We walked to the auditorium, me following her. When we walked in, the place was packed. Tina told me to go back to the car and get the brandy glass from the trunk. All I could find was this huge glass, probably half a gallon. On the way back, a guy asked me if I was going to drink that much cum. I told him I’d try. He told me I was one fucked up faggot. I just smiled at him.
Tina was on the stage and she told me to hand the glass to the front row. As I looked around, there were a lot of female students mixed into the crowd. My cock got hard thinking of women watch me do my faggot stuff in front of them.
Someone had brought one of those leather covered exercise horses over and placed it in the middle of the stage. Tina ordered me to bend over it and a couple of her guys spread my legs and cuffed them on the corners, then they did my hands. I was completely helpless, but I was liking it. I heard Tina ask who’s first. She told the crowd that her faggot had been very bad and needed some serious punishment.
I felt a cock probing my ass and the crowd cheered. Then the fucking started. A cock was soon presented to my mouth, which I welcomed as I began sucking it. Camera flashes were going off as guy after guy took their turn, either getting a blowjob or fucking me. My only problem was I couldnt see much from my position. I could tell there was other things going on, I figured Tina was fucking guys she liked. She would feed me that cum later, I was sure.
The fucking continued much longer than before, the crowd roaring with every new cock. Finally, someone took off my restraints and I was allowed to stand up. Again, the audience responded, shooting and making cat-calls. Tina asked them if they wanted to see me fuck the black guy with the huge cock? The crowd yelled for more. The piano bench was brought out and I was ordered to lay back on it. The big guy strolled out from behind the curtain and was fully erect. The girls were no responding on their own, not believing that anyone could handle that much cock.
Tina walked over and announced that while the guys were having their way with me, she had fucked 41 guys. She asked if I had any idea how many cocks I had taken. I had no idea. She said 142 guys had fucked me and I had sucked 181 cocks.
She then said I was going to eat her pussy which was gushing cum as she straddled my face. As I started licking her dripping cunt, I felt my legs being lifted up on the black stud’s shoulders. My butt was also full of cum as he slowly pushed his cock into me. I could hear the women screaming for him to fuck the faggot, fuck the faggot. We probably performed for 20 minutes before Tina was satisfied. The cock was pulled from my ass and Tina whispered that I needed to beg for the big cock to be placed on my mouth. I begged, but she made me say it louder, and louder again. I got on my knees and took the cock into my mouth and wrapped both hands around it and sucked and jacked it off. Tina said I should beg for his cum. So I begged for it, begged him to feed me his cum. He finally shot his cum down my throat.
Tina helped me stand up, then asked the audience if they thought I’d had enough cum. Apparently, the answer was no, because one of the girls brought up the big brandy glass and handed it to me. As I looked at it, I could see there must have been half a gallon of white creamy cum in it. I didnt think I could possibly drink that much cum. Tina looked at me and said, “Drink it bitch! Drink that hot cum!” The audience started chanting ,“Drink it bitch! Drink that cum you fucking faggot!” I tipped the glass up with both hands and started guzzling that cum. Oh, I love cum! I stopped a couple of times for air but Tina told me to keep drinking, which I did. I was almost finished when Tina told the crowd we had special guests. I was finishing the last little bit when I heard Tina say, “My sister’s parents just showed up to watch their son in his latest performance.”
I looked up at the center doorway, and there were my Mom and Dad, looking at me in horror. The crowd erupted in a standing ovation. Tina took the glass from me and asked if I had anything to say to them. I watched them turn and rush out of the building in total disgust. I was too ashamed to try to catch them. I was a fucking cum slut and they had seen me do what I enjoyed doing, sucking cock, getting fucked, and drinking cum. And for some bizarre reason, I grabbed my cock and began jerking off in front of everyone until my cum splattered on the stage. Why did I do that? I dont know? I’m a slut is the only answer I could cum up with. A fucking slut.
When I got home, I tried to call my parents but they wouldnt answer. I kept calling until my Mom finally answered. When I tried to explain, she wouldnt listen. She said I had no place in their lives and to never contact them again, ever. She said I was not part of their family and leave them alone.
I was devastated, lost, and unsure what I would do. I continued to dress up, but rarely went out. Tina was apparently finished with me. I was at my lowest low. The money my parents had been sending disappeared and I knew I needed a job.
Then one day, I got a call from an older guy, asking if I was looking for a job. I asked what kind of a job. He said it was completely legal and he was sure someone with my skills could handle it. My skills? I didnt know this man.
He gave me a time and an address and thanked me for my time. He seemed nice and I did need a job. What would it hurt. I decided I’d check it out.
The next day, I put on my best boy clothes and drove my old truck to the address he had given me. It was a huge house on a hill overlooking the river. I knocked on the front door and it was opened by a distinguished looking gentleman. He looked a little disappointed as he welcomed me into his house.
I asked him what was wrong. He confided to me that he had been at the college in the audience and had expected that I would be dressed as a girl. I guess I smiled and blushed as I thought about it. I told him I had been dressed in sexy feminine things right before I came out. He asked why I changed and I told him I thought I was here about a job. He laughed and said, “You are.”
He started telling me how he had heard stories about me and had gone to the college to see if they were right, and he said he was amazed by both my beauty as a woman, but also by my skills to please men. He said he had never dreamed there was anyone that could suck and fuck like I had. He said that recent surgery for cancer had left him unable to perform sexually, he still got gratification from watching me.
He went on to say that he had lost his wife a few years earlier and his son had died in a motorcycle accident, so there was no family. He said that when my parents walked away from me after witnessing my homosexual activities, he said he had to reach out. I thanked him.
I asked about the job and he said he needed a hostess, somebody that was willing to do whatever was needed to make his business partners happy. He asked if I could do that and I told him I was good at following orders. He laughed and said he had seen that at the school.
He said his name was Harold Footh and he ran several businesses. He said that he would prefer that I live on site and be available for special occasions. I would have a bungalow for myself but also the full run of the house and pool area. Anything I needed, he would take care of. Then he asked, “Want the job? I think you will be very happy here. Come on, work for me.”
I told him I would be happy to take the job. He handed me a clipboard and asked me to write down my sizes and any special things I might need. I filled it out, noting all of my girl sizes. He looked it over and said fine. He walked me out to my truck and as I got in, he said the truck wasnt going to cut it. He said he would get me more suitable transportation when I came back to start my new job the next day. I told him he didnt have to do that but he said it would be his pleasure. He then had one request before he let me go. I said OK? I asked him what that was and he quietly said that if it was OK, he’d like to have my permission to watch me have sex with my special friends. I leaned out of the truck and hugged him, telling him I’d be honored for him to watch.
I drove home, my mind whirling about what had just happened. I went to packing my few items. I felt the need to put on some sexy things. I took all of my boy clothes and boxed them separately. I put on my sexy white lace crotchless panties, white cutoffs, a pale pink long sleeved peasant top and my pink platform heels. I took my boy clothes and drove to Goodwill and gave them away. I was done with boy clothes.
I drove out to see my shoe salesman. I needed to be fucked. I walked into the mall, confident in my new female role. I walked into the shoe store and my salesman was busy flirting with a couple of 20-something girls. I walked over and as they watched, I gave him the most erotic kiss I could. As I did, my hand found his cock in his slacks and I rubbed it to full erection. I looked at the 2 women and told them I was going to suck his cock and then he was going to fuck me. I asked if they wanted to watch. They looked at each other, then agreed they would like to watch. The salesman locked the door and the 4 of us walked into the back.
Once there, I stripped the surprised salesman completely naked and kissed his lips, his neck, his nipples, then knelt in front of his hard cock. I looked over at the 2 women as I took his cock into my mouth. I slowly sucked it, each time letting his hard dick slide further into my mouth, until his balls were against my chin. I left it right there and let my mouth massage his cock as I continued to alternate between soft sucking and harder sucking. My salesman suddenly grabbed the sides of my head and yelled out he was coming, which he did. I co tinued sucking his cum out of his balls, finally releasing him.
One of the women said she had never seen anyone deepthroat a cock like that. And the other asked how I made him cum without moving, just by sucking. I just smiled at them. I asked if they wanted to try his cock and one knelt down beside me. I held his cock to her lips and said, “suck it, slut.” She did and he was soon hard. I thanked her and told her I needed to borrow the cock for a few minutes. I backed my ass into his hard cock and told him I needed him to fuck me. I spread my legs, grabbed the back of a chair and felt his cock enter my eager ass. I loved the feeling of being fucked in the ass, the feeling of having these 2 women watching.
Just then, the curtain suddenly pulled open. It was the salesman’s wife, bringing him lunch. Her sudden surprise arrival led him to suddenly cumming as she watched. She said, “So this is you secret lover, the one you talk in your sleep about? Shes a fucking guy, you asshole.” Then she walked out. The 2 women just giggled, I guess happy they weren’t yelled at. I turned, kissed the poor guy on the lips and told him I’d be back.
The next morning, I packed my belongings into a few boxes and put them into my old truck. I dropped a note in my landlord’s mailbox thanking them for renting to me. I had decided since my new boss had been so disappointed at seeing me in my male clothes, I’d show up as cute and feminine as I could. I wore all white lingerie, including some white thigh highs and white 4 inch heels, along with a pretty pink mini dress. I also wore my sexy dark brown wig. Ok, I was ready for the world.
I walked back around the house to my truck, planning on leaving for my last time. As I rounded the corner, there was the cute teachers boyfriend, leaning on his car, looking back up the drive. He turned to see me, and seemed to be speechless. I said, “Hi,” and he muttered a quiet Hi back. He then said,“You’re the guy from upstairs?” I told him I was and all he could say was, Damn. He said his girlfriend said I was the prettiest boy she had ever seen. He said, " You are the prettiest human being I have ever seen." I blushed at that. This guy was sweet. I asked why he was waiting and he said he had a lunch date with his teacher friend, but he was an hour early. He thanked me for stopping and introducing myself. As we stood and talked, I could see him stealing glances everytime I turned or bent over. He asked me about why I started crossdressing and I told him my story, or at least some of it. I told him about dressing for my best friend and doing my first blowjob. He surprisingly said that he wished he had had a friend like me when he was young.
I asked him if he’d like to see what he missed? He said, what do you mean? I told him if he wanted to follow me to the little secluded garden in the rear of the apartments, I would show him. I took his hand and led him around the corner. I pushed him up against the wall and eased his pants down. He had an immediate hard on. His cock had a large mushroom head, like I liked. I sat down at the picnic table and pulled him to me. I slipped my mouth over his cock and gave him a nice, long wet blowjob. He tried to pull out as he was about to cum but I took his cock out of my mouth and told him I loved cum. Then I slipped his cock back to my mouth and made him cum. Mmmm, he tasted good. When I had finished, I asked him if his teacher friend sucked cock like that. He said, not really, and we both laughed. He then said he better get to the parking lot. As we walked around to the lot, the teacher was just getting out of her car. She said, “Dont you look pretty today.” I thanked her and she asked what we were doing around the house. I smiled at her and quietly told her I had been giving him the best blowjob he had ever had. She looked at me and then at him, and said, “Yeah, right.” I told her I was showing him the garden area, and that I was moving. She asked if I was moving in with the little brunette and I told her that we broke up. The teacher said I should stop by if I was ever out that way. I told her I liked her boyfriend, he was sweet. I didnt bother to tell her I loved sucking his cock or that I liked eating his cum.
I got in my truck and backed out, waving at the two cuties. I drove thru town and out to the big house. I parked next to a new white Corvette, wondering who was there. I carried my two small boxes to the front door and knocked. Harold opened the door for me and said, " That’s more like it. You look fantastic. I took the opportunity to pick out a car more suited to your new position. What did you think?" I looked at him in disbelief and asked, “The Corvette?” He just smiled and said if I didnt like it, I could get something else. I gave him a big hug and he told me to go out and give the salesman the keys to my old truck. I did as he said and watched my old rig make it’s way out to the road and disappear.
I went back inside and Harold asked if I was ready to start work? He said I could take my things to the bungalow and settle in. He said one of his secretaries had picked up my uniforms and other necessities and layed out one in my room.
I was eager to see what my new boss expected of me. On my bed was a complete French maids outfit. Fantastic!! I always had a fascination for those short black dresses, the white petticoats, little white lace aprons.
I quickly undressed and put on my first French maid outfit. There was a short sexy wig with a lace band on the top. As I looked in the mirror, all I could think was that I made a sexy maid. I walked over to the big house.
Harold had me model my outfit for him and said he was very happy with it. He asked if I had any reservations about the job and I told him that as long as he let me know what he expected, I was good with it. He said he was expecting e close friends for a meeting in a few minutes. He said they were used to getting what they wanted, so i should go along as i saw fit. He said, dont be afraid to say “No.”
I was to bring drinks and basicly be eye candy. I asked if they knew i wasnt really a girl? He said, “Not yet”, and laughed. The door bell rang and Harold asked if i would greet his guests. I went to the door, opened it and directed the men to Harold. All three looked at me as they went by, one of them uttering something about Harold always having the most beautiful girls working for him.
I went to the bar and waited for the guys to order their drinks. After ordering, they went back to the boardroom to discuss whatever rich guys discuss. I just puttered around the bar, bending over to show my panties, smiling at them when they looked at me. They finally came to some kind of positive agreement. Harold called out, “Miki, can you bring us some brandy?”
I took them the brandy and asked if they needed a thing else. I heard one of them mutter, “A blowjob would be nice.” I walked over to him, smiled at Harold, and asked Harold if he minded, as I motioned Richard, to join me on the deck. Harold said ,“No, of course not.” I escorted Richard outside. I ran my hands up his chest and onto his shoulders, then I knelt down in front of him and pulled out his cock. He apparently was a little frightened by what was going on and his cock had not started to get hard. I could fix that. The other men were standing behind the glass watching. I kissed Richard’s cock and it started to respond. I took his soft cock into my mouth and then eased his balls in with his cock. That did it. He began to harden and I began to suck him. I looked over at Harold and he looked like a proud Papa. I sucked Richard until he finally came. I then stood up and asked if anybody else needed to have their cock sucked? Not so surprising, both guys said sure. I sucked both of them to fantastic orgasms. When we came in, Harold said I certainly deserved a bonus. I smiled at him and told him it was part of the job and I enjoyed servicing his friends.
I escorted the men to the door and I think all three managed to cop a feel of my ass as they left. I came back in and Harold handed me a check for $10,000. I protested but Harold said I earned it. He said during their meeting, the guys were so interested in what I was doing, they agreed to everything. He said he was going to make over a million dollars on that agreement , and he thanked me again.
I took my bonus out to my little place, thinking that I was going to love this job. I changed out of my uniform, into cutoffs peasant top, and high heels and walked out to my new Corvette. The paperwork was in my name and there was an insurance coverage letter there too. I started the car up, thinking, “Boy, this is way better than a 1959 Dodge truck.”
My life had really changed.
As I drove my new Corvette thru town, I had to wonder what was next in my life. I guess there was no hurry, as my new boss obviously had plans for me. As I drove. I found my cock hardening with the many thoughts rushing around in my head.
It was late and not much was going on in town. I saw Tom’s van at the regular spot and thought I’d stop and see if I could find some cock. I pulled in next to Tom’s van and got out. Tom was there along with a couple of friends. Tom greeted me with a big hug. He then told me he heard some sexy stories about me at the college. He laughed and I asked if they were good. He said they were, especially about fucking over a hundred guys. I blushed and told him I was having fun, that’s all.
I told Tom and his friends that I was horny and hoping to suck some cock. They all agreed. I sat down in the Van’s rear door opening and pulled Tom close, pulled down his pants and watched his cock spring to life. Tom really did have a nice cock. I slid it into my mouth and pulled Tom closer, indicating I wanted him to fuck my mouth. He complied and was soon fucking my face. I liked it when guys did that. Tom kept thrusting deeper, not realizing I could take it all. Then he came, filling my mouth with his cum. He pulled out and I opened my mouth to show Tom and his friends the cum rolling around on my tongue. Then I seductively swallowed the sperm.
The other guys wasted no time in presenting their cocks to me. I hungrily satisfied each of them. After finishing, Tom asked who the Corvette belonged to. I told him it was mine, which he had a hard time believing. I assured him it was mine and i told him i was working in town. I didnt give him a lot of information, just that I’d be around.
As we we talking, a couple of girls pulled up and got out to talk to the boys. One of them looked at me and said she had seen me at the college. She said i was awesome and she found it very exciting when i fucked the big black cock. She said she came while watching, it was hot. Tom asked, " a black cock? How big? The girl said it was huge, maybe 14 inches long. I corrected her to tell Tom it was only 12 inches. Tom laughed and said that must have been hot.
The other girl told him what was really hot was when the guys collected all of their cum and i drank it. I just smiled and told them i liked cum.
I drove back to my new place thinking about Harold had said about if i needed anything, i just needed to ask. I had been thinking about it for a long time, i needed boobies. Yes, that’s what i needed. I’d ask Harold if he would help me get some. I masturbated again as i pulled into the driveway.
This was going to be fun. I wanted to be the best slut possible.
I liked my new place, although I did miss my porch and being able to go out there at night and enjoy the idea of being discovered. But my patio did overlook the river, not that there was anybody at night.
The next morning, Harold called and said I could have the day to myself, since he was going out of town. I showered and went in to see what I wanted to wear. There was a black bikini, very skimpy but equally sexy. I put on the bikini and some black heels. I went out to the pool and stretched out on one of the lawn chairs. I spent a little too much time in the sun and got a little pink. When I took the bikini of, the skin underneath was my normal skin color, looking very erotic, showing my tan lines. I dont know why that excited me but I spent hour rubbing my little nipples and squeezing my pretend breasts.
I didnt see Harold until the next afternoon when he called me to come to the big house. I was wearing sexy panties, heels and a see thru top. When I walked in, Harold looked at me funny and asked if I had been sunburned. I told him I had dozed off in the sun. He laughed and told me to be more careful.
He went over plans for a party he had planned for the next weekend. He said he was leaving it up to me to decide what needed to be done. He said some were bringing wives, so I needed to use a little discretion but he did understand that some of the women were pretty wild. I told him that I’d be careful.
Harold asked if I needed anything for the activities. I confessed that I was curious about female hormones and breast enhancement. He thought for a minute and then said if I was serious, he would arrange a doctors visit. He said he thought that some nice boobs would be fun. I left the room dancing and singing, “I’m getting new boobies, I’m getting new boobies.” I heard Harold chuckle.
Harold had given me a list of guests and a brief biography of each. I studied those, trying to get an idea of who would play and who wouldnt. Most would, but the wives were hard to read.
On Wednesday, I got a call from a doctor friend of Harold’s. I went to the appointment, dressed in a white blouse and black slacks, not too over the top. The doctor and his staff were very nice and very understanding. I was given a full physical, which was a little nerve racking, since I was without any body hair.
Afterward, the doctor talked to me, explaining the procedures. He said he wanted to start with some hormone treatment to get my body more feminine, then follow up with breast implants. He asked if I was sure I wanted to do this, and I told him I was sure. He said the nurse would come in and give me an injection and a prescription. He did say that my sex drive might diminish. I thought, humm, I doubt it.
Friday night, I dressed in my cute French maid outfit, did my makeup and put on my wig and heels. Harold had hired a bartender and 2 young guys to carry drinks. My job was to greet the guests and escort them into the house.
The guests started arriving and I greeted them. I was getting some serious looks from the single guys and some admiring looks from the wives. The night went very well and all of the people seemed to be doing well. One guy was groping my ass when one of the women came over. She told the guy to knock it off, but I took his hand and put it back under my short dress. The woman looked at me and said that wasnt how a young girl should act. I whispered, “I’m not a just a regular girl”, and winked at her. I took her hand and put it under my dress on my panties, allowing her to feel my soft cock. But instead of being shocked, she cupped my cock and balls, gently rubbing them thru my panties. She yelled across the room, “Sharon, this pretty French maid is a boy”, and the other women came to check me out. The women had many questions, was I gay, did I have sex with men, was I going thru sex change surgery, and on and on.
I told the basics of my story and how I had just started hormone therapy. One of the women asked what I liked about having sexy with men. I told the women that I just loved to suck cock and was pretty good at it. They were curious if I did anything else and giggled when I told them I liked to be fucked. One of the ladies asked if I ever let anybody watch and I told her it turned me on, a lot. She asked if they could watch me have sex, so they could watch. I looked around and told them it looked like all of the guys were busy with Harold. Another lady asked if I liked black guys? I said I did, why? She said there was a tall nice looking black guy parking cars. I said, “Really?” Two of the women said they’d go out and offer him a couple of hundred to come in and put on a show.
The three came in and I saw this was my friend from the school and went over to give him a hug. He said hello and asked if these women were serious. I told him they were definitely interested in seeing us have sex together. He smiled and said he remembered the last 2 times I had sucked and fucked him. I said we should do the same as before. We went to the living room, along with the giggling women. We undressed, me down to my garter belt, nylons and high heels. I had to run out and do my K-Y treatment, but came right back. The black guy had his back to the women, so I stepped up beside him, so they could see my cute bottom next to his firm muscular butt.
I turned him to face me and I reached over to lift his massive cock. The women were impressed as I head it. I stepped over and kissed my friend. One of the women uttered. “Damn, that’s sexy”. He held me close, then let me slide down to his big cock. I kissed it, then slipped my mouth over it. I heard the women excitedly discussing how huge the cock was and no way they could handle it. At that, I knew it was time to show them what I could do with this 12 inch cock.
I slid the cock into my mouth, about half way and sucked on it. Then once I knew the women were excited, I pushed another couple of inches into my mouth. I then reached around to hold onto that sexy black ass and pulled him forward, almost to the hilt. He pulled back and I urged him to go deeper. He took the hint and started fucking my mouth. Just then, i noticed the guys had joined the women, watching my little sex show. My stud started fucking harder and harder before finally pulling my face to his body and began shooting cum into my mouth. I sucked cum out of his balls as the group watched. He slowly pulled out and i opened my mouth to show them the cum, then i closed my mouth and swallowed, then opened to prove i had eaten the huge load of cum.
A blonde ladies asked if i could fuck him and i said i would if he wanted to, but he might need a hand or 2 to get in the mood. They took the hint and came forward and started touching probably the biggest cock they had ever seen.
I noticed Harold overlooking what was happening and he smiled and gave me a thumbs up. Then, one of the women said, “Miki, we think hes ready.” I walked over and reached out for my guy’s cock and asked if he would please fuck me. He said, “Oh, get ready, I want your ass.”
I turned one of the big leather chairs around and bent over the back, spreading my legs for my black lover. From this angle, everybody could see his huge cock as he fucked me with it. We fucked, and fucked, and fucked until he finally shuddered and I could feel another load of cum as it filled my ass. He finally pulled out and cum began seeping from me. The general opinion was that was HOT. I just smiled. I asked if anyone else wanted to put on a show. No answer. So I addressed the blonde lady and told her if she would fuck all of the guys, I would eat her pussy afterwards. She declined but said Maria might take me up on it. I looked at the pretty lady, definitely Hispanic, and asked her if she would. Her husband nudged her and said, “Honey, why dont you, I want to watch.” He helped his wife undress and she had a very sexy body. Clothes started coming off and soon she was being fucked by multiple cocks. The other women were busy with my black lover, cleaning his cock and stroking him as they did. I think they all took turns trying to suck him but none could take much.
Finally, Maria was finished, or she thought she was. I told her she missed a guy and I brought my lover over to her. She didnt protest when he leaned her back in the chair, lifted her sexy legs up over his shoulders, and started teasing his huge dick into her. She was tight, but all of that cum made her extra slick. They fucked for about 15 minutes with everyone watching. One of the husbands had made his way over to me and I felt his hand slide between my butt cheeks and into my cum-filled ass. He finger banged me for a few minutes, then slipped his cock into my super juicy ass. At the same time, he reached his hand around to push his wet fingers into my mouth. I sucked the cum off his fingers as he fucked me.
Soon, Maria was finished and the other women told me to eat her, to suck the cum out of their friend. I knelt between her legs and admired her wet pussy. I lowered my mouth to her pussy and began eating her out. She was really getting off to this, screaming and convulsing as my tongue tried to keep up with her. Soon, I had another guy inserting his cock into me. I found it very comfortable to have a cock fucking me while I ate a creamy pussy..
Everyone started to get tired and we all collapsed on the couches. The lady sitting next to me slowly slipped her hand into my lap and she found my cock, she stroked me until I came, then realized he’d down between my legs and fingered my leaking ass. She told me I did a wonderful job and she learned a lot. She asked me if I thought that I could get my black friend to fuck her sometime. I told her I was sure I could accommodate her.
When morning came, everyone got dressed and left. I was standing at the open door with Harold’s arm around my waste. He told me I really did well with his guests and they had come to some terrific business dealings. He said we were a great team. He went to his desk and pulled out his check book and began writing. He handed me a check for $200,000 and said he would pay for my new boobie. He told me to take a few days off. I told him it was too much money and tried to hand the check back but he wouldnt take it. He said he had enty as was going to make a lot more. But I told him I was just having fun. He said he could tell, now, take the damn check. I did what he said. I was liking this job.
The next month went well. I was taking my female hormone pills and getting weekly hormone shots. My body was changing, getting softer, my nipples were getting bigger and way more sensitive. Harold’s secretary had found me an understanding beauty salon and my hair was getting longer and more feminine looking. I hadnt had any new lovers and I needed one. I was horny and craved a cock to suck. I had driven around town, and while I got a lot of looks, no guys. Harold had been travelling so there were no visitors at the house.
I decided I’d visit the local adult store, there had to be horny guys there. I dressed in a super short slutty dress, red in color, showing a lot of cleavage, since I was starting to have some. I put on a pair of 6 inch platform heels, like a hooker would wear.
I drove to the adult store and got out, pulled my dress down and walked in. The guy at the counter asked if he could help me. I looked around, not many guys, so I told him I wanted to suck cock. He just looked at me, then pointed down the hall. He said there was one room with a glory hole. He said to go in and put my hand on the opening.
I did as he said. This was a very clean place and a tv screen showing porn. I heard the door open in the next cubicle and then a nice hard cock appeared thru the opening. I stroked it a few times, then put my mouth over it thinking, this is what I need. I sucked until the cock filled my mouth with cum. The cock disappeared and as I was getting ready to leave, another hard cock came thru the hole. I sucked cock all afternoon, getting my fill of cum.
As I left the stall, I was greeted by a hall full of guys, guys I had sucked. One of them asked if I would like to fuck. I asked if he cared that I wasnt really a woman? He said it didnt matter to him and asked if anyone else minded. No complainers, so the first guy led me down the hall to a large room with a bed in the middle.
I took of my dress and panties, but kept on the garter belt, nylons, and stripper heels. The guy was naked by then and pushed me back on the bed, spread my legs and I helped his cock find my asshole. The room was full of horny guys, watching as the guy fucked me like a mania . It was great. When he finished, another guy mounted up, also fucking me and shooting his cum into me. I guess I fucked 20 guys but as I layed there, I noticed a cute young guy watching. I motioned him over but he just stood there. I asked his name and he said it was Billy. I told Billy I wanted him to eat me. He protested pointing out that it was my butt and it was full of cum. I licked my lips and reached down and ran my fingers over my wet opening, then licking my fingers. I again told Billy to eat me. The other guys grabbed illy and picked him up and carried him to my dripping asshole. They held him there and again, I told Billy to eat me. The guys pushed his face between my legs and I could feel his hot breath on my inner thighs. I reached down and pulled his face into my wetness, again telling him to eat me. He started licking sloy, but as he got to tasting my cum, he started licking faster and deeper. The guys let him go so they could watch and he continued eating me. His tongue was sliding deep into my ass, getting every drop of cum. I actually told him he could stop and he continued until I was clean.
I told him I’d like to watch him suck a cock. He didnt offer much resistance and he was soon on his knees, sucking several of the hard cocks presented to him.
Billy was small, like me, and very cute, blond hair and light completed with big blue eyes. I asked the guys if they thought I should teach Billy to be a slut like me. Billy’s eyes were wide open as I asked him if he wanted to be a slut like me? He just nodded his head, without uttering a word. I then told him it wss settled. He would be my bitch and do what he was told. He would suck cock and get fucked whenever i told him.
Over the next month, I continued with my hormone therapy. On my next doctor’s visit, my doctor examined me and told me that if I was ready, he would perform my breast enhancement. I was thrilled. I immediately went to see Harold and tell him what was happening. I told him I had met a young guy, much like myself, that’s was willing to step in for me while I was healing.
Harold said he would like to meet him first but he was going to be out of town for 3 weeks. I told Harold that was perfect, that I could train him. Harold asked if he would be interested in moving in with us. I told him that would be perfect.
I called Billy and told him I’d pick him up at his place, his Mom’s house. I pulled up to her house and got out. I was wearing a modest floral dress with 3 inch heels. His Mom answered the door and greeted me, inviting me in. She seemed relieved that Billy had a girlfriend. I told her that my boss wanted Billy to work for him and live on site. She said that would be nice.
Billy came out and I went up and hugged him and gave him a nice quick “girlfriend” kiss. His Mom asked where we had met and I quickly told her it was at the bookstore. Illy looked a little frightened, but I didnt say it was an adult bookstore.
We left and on the way, I told Billy today was the first day of the rest of his life. I told him his training started as soon as we got back to Harold’s place and got settled. I walked Billy to the other apartment next to mine. I had already ordered Billy’s new clothes and told him to get showered and I would be over to help him.
I called my friend at the beauty salon and asked if she had time to give a makeup lesson and she said she had the rest of the afternoon clear. She came over and i took her back to Billy’s apartment. I knocked and Billy told me to come in. He was wearing a cute nightie and was shocked at a woman coming in with me. I told Billy that Barb was familiar with girls like us. I left to allow Barb to teach Billy how to do his makeup.
I was sitting on my patio when Barb came out. She stopped and told me she thought Billy had it but she would come over in a few days and see how he was doing. I thanked her and gave her a crisp hundred dollar bill.
I walked over to see how Billy looked. I knocked and he answered. I was impressed by how he looked. He made a very cute girl. I told Billy his new name would be “Billie”. I told him that from now on, he would only wear the clothes I gave him. I told him Harold wanted to meet him when he came back from his business trip. I told him that sometimes he would wear the French maids outfit, other times, sexy things. I told him if he had questions about how to dress to just ask me. Billie had shoulder length blond hair and Barb had helped him steal it. I told him to pick out something sexy and we would go out onto the property and discuss his duties.
Billie dressed in a white frilly blouse and short pink skirt, pantyhose and some cute 4 inch high heels. He looked very sexy. He was a little nervous as we went out and strolled around the grounds. I gave him some pointers in how to walk like a woman in high heels. I reminded him again that he had to do what I told him, when I told him. He said, OK, to that but I wanted to test him. As we came around to the front area the landscaping crew was working. I sat down on one of the many benches and pulled Billie down next to me. The landscapers were watching us as we sat together. I be t over and kissed Billie on the lips. We kissed for a long time, our tongues probing each other’s mouths. Then, I said, “Billie, I need you to suck my cock until I come, then eat me”. Billie said the guys were watching. I told him that it turned me on. I layed back, pulling my dress up exposing my legs but hiding my cock. Billie looked at my cock and immediately lowered his face to it. He began sucking me and I must admit, he was pretty good at it. I looked over at the landscapers and noticed they had moved closer, pretending that they were working. It excited me to have them watching and I came at Billie’s blowjob. I spread my legs and told him to eat me, and his lips found my sensitive opening and his tongue skipped into me, eating me like I had asked. I looked up to see that the landscapers had came right over to where Billie and I were putting on a show. They were Hispanic but I knew they were turned on. But I figured Billie had enough fun for one day. We walked hand in hand back to the main house, where I took Billie in my arms and we kissed again while waving at the groundskeepers.
I was ready to teach Billie more of what was expected of him. I made my appointment for my surgery and was ready to move on. Billie asked me about my hormone therapy and said he would like to do what I had done. He asked if he could get tits like I was getting. I told him that would depend on how he did his new job and it would be Harold’s call, but i told him i was sure there would be no problem. Next time, more training for Billie.
Over the next couple of weeks, I coached Billie about what was expected if her. I knew that she had not had any anal activity and I needed to fix that. So, one evening, I took a collection of vibrators to Billie’s apartment. We sat on her bed and started making out. She had really gotten very good applying her makeup and looked very feminine. We started getting more serious and I had Billie lay back on the bed, spreading her legs for me. I started sucking her cock and as she got more and more excited, I slipped one of the lubricated vibrators into her ass. It didnt take much of the buzzing action to make her cum. I sucked down her cum, like I liked. As we layed there, I introduced her to my other toys. As the size increased, Billie took them with ease, begging for more and more. I got between Billie’s legs and slid my cock into her. There we were, both in sexy lingerie with me fucking my new trainee.
Everyday, we spent the day making love, always ending with me using my huge vibrator in her sexy ass. She was really getting into having a huge cock replica in her ass.
Harold came back from his trip and I arranged to bring Billie to an interview the next morning. I told Billie to dress in her French maid dress in the morning.
Billie and I went to meet with Harold, both of us dressed in matching outfits. Harold interviewed Billie and seemed pleased. He asked if she understood that she might be requested to perform sexual activities while acting as a hostess. She said she understood. I looked at her and said, “Eat me, you sexy slut.” Billie pushed me back on the overstuffed leather couch and slid down between my legs and started by sucking my cock before turning her attention to my ass. Harold seemed to enjoy the show as Billie’s tongue fucked my ass. Finally, I stood up and pulled my dress and petticoats up, exposing my hard cock, I pushed Billie down to my cock, grabbed the sides of her head and started fucking her mouth. As our boss watched, I shot my cum into her mouth, which she swallowed.
Needless to say, Billie got the job. We were a nice pair, me with big brown eyes and brown hair, Billie had bright blue eyes and beautiful blond hair. We would definitely bring something new to our bosses special meetings.
The next week, I had my breast implant surgery. I was a little sore and bruised but I was happy. My new boobies were not huge, but very natural looking. I was very happy with them and couldnt wait to heal up so I could flaunt them.
While I was recuperating, Billie got to host one small meeting. Harold told me she did a great job and asked if it would be alright to furnish her with a car of her own. I told him I thought that would be a wonderful surprise. I suggested that a red Corvette, matching my white one would be pretty sexy. Harold laughed and told me it was a done deal, his two girls would have complimenting cars. I told him that she had asked about breast enhancement, like mine. Harold said that would be perfect, again, he liked the idea of his two girls had matching tits.
A couple of days later, Harold called us to his office. I showed him my new boobies and thanked him. He looked at Billie and asked, “Would you like some oobies like Miki?” She looked at my tits and told Harold she would love some. Harold told her she had earned them and that he had another surprise. We walked outside and there was her new Corvette, parked next to mine. Billie gave me a big hug and kissed me. I told her that Harold had bought her the car and he should get the hug. She rushed to Harold and gave him a nice hug, then ran to her new car and slipped behind the wheel. She was very happy.
I healed extremely well and I loved my new tits. Billie had started his female therapy and was starting to look amazingly feminine. We were laying by the pool, both of us wearing just very skimpy bikini bottoms and high heels. My suit was white and Billie’s was hot red. I asked Billie if she had ever told her Mom what he was doing. She said she hadnt gotten up the nerve to tell her that her baby boy was living as a girl. He said his parents were divorced, so he didnt have to face an angry father. I laughed. I asked if he had thought about being honest with his mother, that he might feel better.
I continued to press Billie to meet his mother as Billie. He finally agreed. I told her she better call first and let her know you have a secret to share. He agreed, then asked if I would go along.
We got into Billie’s red Corvette and drove to her mother’s house. Billie was very nervous but I told her it would be alright. Billie knocked on the door and Billie’s mom opened the door, looking at 2 cute girl standing on the step. She recognized me, then just stared at Billie’s feminine face. Finally, she asked, “Billy? Billy, is that really you?” Billie said it was, that he was now “Billie”, a sexy girl, living as a female, working as a female. Billie’s mom was starting to cry and said she had always wondered about Billy’s sexuality. She said she was more comfortable with Billy being female rather than being a guy having sex with guys.
Then, she asked me if I was also born a boy and I told her I was. She said i was too pretty to be a boy and said i looked so feminine and my breasts were very natural. I told her Billie was going to get breast enhancement surgery. She asked if we were a couple, and i looked at Billie and said," I guess we are". Billie bent over and we kissed. His mom seemed to be accepting as we sat together. She asked if we wanted some tea and went to fix some. I let my hand slip under Billie’s short dress and was shocked to find he had a hard cock. I started stroking it while he talked to his mom in the kitchen. I felt his body tense and she came right there on her mom’s couch. I quickly grabbed a tissue and cleaned his wet cock before her Mom came back.
On the way back to our place, I asked if he wanted to meet an old friend? He asked what kind of friend and I told him it was a guy I met while shoe shopping. We drove to the shoe store at the mall. We walked in together, getting a lot of attention from the guys we passed. We walked up to the shoe store and walked in. My friend was setting up a display when I walked up and said," Hi, remember me?" My friend was wearing a name tag, Nick. I gave him a hug and introduced Billie. Nick told me his wife almost divorced him when she caught us having sex. I asked how he managed to escape that. He said it had been close. His wife was really pissed but the fact I was not a woman, she felt a tiny bit better but he was never supposed to repeat the act.
So, I asked Nick, “So, you wouldnt let Billie suck your cock?” He didnt really have an answer so I added that Billie wasnt a woman, and she would love to suck your cock. Billie stepped forward and gave Nick a peck on the cheek and her hand found the outline of his hardening cock in his slacks. I told them to step into the rear and I would watch the store. They disappeared behind the curtain just as a tall, good looking guy came in. I asked if i could help him and he said he needed a pair of work boots. I asked the size and went into the back, where Nick was getting a very thorough blowjob from Billie. I told Nick what I needed and he pointed at the shelf behind me.
I went back to my customer and told him to sit down. I sat on the fitters chair, spreading my legs slightly to show my thong panties. I was slipping the boot on and I looked up to see my customer looking at my new tits. My nipples got hard at the new attention. After being satisfied with his boot selection, I walked over to the shoe liner rack and bent over, keeping my legs straight and showing him my long legs and my ass. I walked back and he asked for another pair, so I repeated the move. I could tell he was incredibly attracted and asked if he needed anything else. He ended up picking out 4 pairs of shoes. I walked into the back and discovered Billie with her dress pushed up over her sexy bottom and ick fucking her furiously. I went back out front and asked my customer if he wanted to see something really hot. I led him back and he saw Nick fucking Billie. I saw his cock hardening and unzipped his Levi’s and pulled his cock free. I knelt in front of him and took his cock in my mouth. I sucked him for several minutes until Nick came in Billie’s ass. I told my customer my friend would enjoy fucking him. I directed him over and guided his cock into Billie’s cum-filled butt. He wasted no time before he was fucking her, saying that this was the tightest pussy he e er fucked, it realizing it was Billie’s ass he was fucking. When they had finished,, I kissed Billie on her sexy lips as the 2 guys watched. Nick thanked me for selling the guy all of the shoes and said if I ever needed a job, to just call him. He gave willie a big hug and that led her for the fun time.
We left the store and as we walked thru the mall, picked up a group of guys following us. Billie looked at me and whispered," I have cum running down my thighs". As the guys followed, I reached under her skirt and ran my hand up between her ass cheeks, while lifting he dress up to expose her cute ass to the guys. I let my hands massage her tender asshole and brought my cum-covered fingers out. I turned to look at the guys and brought my wet fingers to my mouth and licked the cum off. I repeated the touching and cum eating as the guys continued to watch. We walked out to Billie’s red Corvette and left before the guys got to us. I looked at Billie and asked if she had fun. She said it had been a wonderful day. We drove home to enjoy the rest of the evening.