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!