It was the early 80’s and I was over my friends house who’s dad had a ton of porno mags in his laundry hamper in his bathroom. We used to look at it while his mom and dad were at work. We loved the looking at the hot girls but what got me the hottest were the guys who dressed as girls. When we couldn’t take it anymore we would jerk each other off but I was the only one willing to give head. At 18 years old these guys would explode down my throat. What really got me off was when I would go home and lube my finger and fuck my ass while jerking off. The explosions were massive.
The images of the cross dressers were in my mind one day as I was at the mall when I was using the men’s room. I needed to jerk off so I was looking for one of the stalls to take care of my pressing need. One of the doors was closed but unlocked, and I opened it to find a man in his 30’s jerking off. His mane was Gary, he was surprised and first but he noticed me staring at his cock so he ask if I would jerk him off but I said no. I don’t know what came over me but I told him if we went somewhere else I would blow him. He said lets go to my car in the parking lot.
I was worried being seen with him so I said I would follow behind him 20 or 30 feet behind him and then when in the parking lot I would get into his car. I followed him behind him and it was all I could do to keep my cock from popping out of my shorts. We got to his car and he told me to take out his cock and suck it but there were too many people around. The parking lot at the mall was relatively full s o finding a quiet spot was hard. Since the man was in his 30’s i figured he had to have an apartment or a house so I suggested we go there. Gary mentioned he was married and could not take me home. So I asked if his wife was there and he said she was at work and not due home for a few hours. I said perfect she is not home but he was worried the neighbors would see him bringing home a man to his house when his wife was out.
I thought about it and asked who lived behind him and if the property had trees i could cut through the house behind him and run in through the back door which he would have already open. We drove to the block behind him and it looked like my plan would work so he dropped me off down the block several houses past were I would have to cut through. I gave him a few minutes and proceeded down the block. No one was looking and I ran through the house behind the Gary’s house and I could tell no one was looking and I ran right into his house.
We smiled at each other because we both thought we were going to be able to pull off what was on both of our minds and we were eager with anticipation. Gary led me to the back of the house were his bedroom was and I started to take off my clothes. Looking to the one side of his bedroom he had a bathroom and I notice his wife had a dressing table with a make up mirror and her closet full of clothes. Intrigued I walked over to it and started poking around her make up. Devious thoughts welled up in my mind and I looked over and asked if he wanted a blow job or something unique. Gary knew what was on my mind and I told him to give me 15 or so minutes to transform myself.
I am of slight build and have very little hair. I don’t need to shave and I have no hair except on my legs and under the arms. Even that is very fine and light colored due to my Nordic heritage. My s****rs share a bathroom with me and I saw how they would but on their make up so I was sure I could do it myself as well.
He went to his bed I completely undressed and sat in the make up chair. I put on her wig, started with the cover girl for base, put on rouge, eyeliner, lipstick, a spritz of perfume and slipped into one of her dresses which was on the tight side. Looking further I put on her stockings and was surprised her shoes fit, I’m a mans shoe size 7 1/2. There were white gloves on the table and I put them on as well. I went to her full length mirror and was surprised at how good I looked. To bad I had no tits because I looked good.
Feeling naughty, I walked out of the bathroom and in my best sultry walk I sauntered over to Gary and his looked said it all but his raging hard on said it even more. I spun around a few times so he could see how I looked. I sat in his lap and wiggled my ass. I slid down to the floor and took his cock in my gloved hand and started to jerk him off. The look on his face was full of desire and I thought he was going to bust right there.
I leaned in and took his cock in my mouth and start to suck on his cock and I would here him sigh and his head leaned back but placed his hand on my head to push my head down to deep throat him. His cock was thin but long and I had no problem taking all of his 7". He seemed close so I stopped and pushed him back on the bed and in an act of deep desire I told him to fuck me. He looked perplexed he never had anal sex so I told him to get Vaseline if he had it and bring it back to the bed. I lubed up his got and me ass and laid on my back. I said fuck me like your wife but just enter in a little lower. He lifted my legs up high and slid his cock around trying to get it in. Finally he was successful and Gary was saying "GOD" your so tight and I reached up with my legs and pulled him in with my legs. His cock was thicker then my fingers but it still felt good. The look on Gary’s face was priceless as he could not believe how good it felt. He started moving and his pace picked up to where I knew he was going to cum. He lunged in all the way and collapsed on my and i could feels his cock pumping cum into my ass. I keep pushing on him and he was in ecstasy. His cock deflated and it fell out along with most of his cum. While I was laying there i asked for some reciprocation and was only expecting to get jerked off, but to my surprise he took me in his mouth and blew me until I came. He actually swallowed my load and then we laid naked together for a few minutes. We both knew it was time to get dressed and get me cleaned up so i could leave.
That was the first of many times I would visit him he got to the point where he would but clothes for me so he could dress me up only to undress me.