I'm married to a very attractive woman and have two kids. My wife satisfies my sexual urges as much as she can but I have a secret that I have kept hidden since we got married. The truth is I like cross dressers, trannies, and lady boys.

When I was a teenager I had a sexual encounter with my best friend Jamie. Two horny teens and only the sexual urge to cum almost daily. We would take turns jerking off on each others young and very hard cocks. We would advance to oral sex within a few months afterwards.

We both got a girlfriend at some point but no matter, we would meet and enjoy each others throbbing cocks many more times even as we got older. By our early twenties our lives took us to live in other States, eventually losing contact. I met the girl I would marry and try to live the straight lifestyle. I got a job with a large company, I would end up traveling a lot and making good money doing it.

I was in Chicago on business and after work I stopped for a drink at a bar on the way back to my hotel. A voice behind me asked if I had a light, I turned expecting to see a guy standing there but it was a tranny. Easy to tell, even though "she" was very attractive regardless.

Her name was "Bobbie" with a lot of makeup, large breasts and eyes that seemed to look into my soul. We moved to a table at her request and began to talk, drink and smoke. Bobbie had long red dagger like nails, her matching red lipstick coated the filter of her cigarette.

She tapped my wedding ring with one of those long nails and smiled. Bobbie asked me directly if I was getting taken care of at home? There was no doubt where the conversation was going and I told her, not completely. Bobbie smiled and those eyes looked deep into my soul.

Bobbie finished her drink and got up, extending her hand to me. I asked where we were going and she laughed. I guess we both knew we were going to my hotel. We started making out as soon as the door closed behind us. Her tongue pushed deep into my mouth and nothing gets my cock tingling as a hot kiss does.

We undressed, well I did. Bobbie took off her skirt, blouse, and bra, leaving her panties, stockings, and heels on. I was stark naked and Bobbie took me to bed and began to suck my cock with hunger.

I was steel hard within moments, Bobbie's lipstick coated my throbbing cock. Then it was my turn, she pulled away and waited for me to make my move. I pulled her panties down and out popped her rather large cock, she was damn near fully erect.

Bobbie spread her legs and stroked her cock a few times until she pulled my mouth onto the head of her cock. She moaned with pleasure as I took the head of her thick cock into my mouth now. I instantly thought of my youth and my best friend, it had been years since I had a cock in my mouth. I had almost forgot the erotic feeling of the warm pulsating flesh in my mouth.

Just as I began to taste the salty fluid Bobbie pushed me away. She told me it was too soon to cum. She reached into her purse and tossed me a condom. She asked if I wanted it doggy or missionary, I told her doggy. Bobbie smiled and got onto her fours quickly.

I spread her stocking legs apart and slipped the condom on my raging hard on. I knelt behind her and put the head of my cock to her hole and pushed. It took a moment before I could open her hole to get my cock inside, slowly pushing deeper until I was balls deep.

We didn't fuck long, within a few minutes I was already to blow my load inside of her hole and she seemed to know. Bobbie leaned forward and my throbbing cock popped out. She turned over and pulled the condom off and tossed it to the floor.

She lay on her back and looked up at me as she stroked her semi hard cock. I knelt between her stocking legs and began to stroke my pulsating cock on top of hers. I began to moan and curse as my orgasm was getting close.

About that time Bobbie moaned and closed her eyes, a thick stream of cum shot upwards and some of it dripping off my cock. That was all I needed to set me off, I fisted my cock and released a torrent of my own cum all over her hand as she milked her cock dry.

From that night on whenever I went to Chicago I called Bobbie to stop by my hotel room. When I was in other places I had either a tranny, cross dresser, or lady boy to entertain my sexual desires for cock.

I have been doing this for several years now. Sometimes I try not to do these things but I'm not able to control my desire for this type of sex. I love women, my wife, but I also love a good hard throbbing cock as well...........................

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Anonymous

by Anonymous on Dec 30, 2017 at 8:21 AM

I'm in highschool and have two friends that I dress up for. I look pretty cute too. We started doing it at sleepovers in middle school. I'd dress up in my or one of their sister's stuff, panties and all and I'd suck them.

It was in eighth grade when Jakie started fucking me panties aside. We tried keeping it secret but Tommy found out and wanted some too, which became even more fun.

I kinda want to try sex with a man now but am scared? There's a man who lives in my aunt's building that comes on to me. He's seen me checking out his bulge in the workout room and pool. He's seen me changing in the locker room and said I look really good in my cute little bikini underpants and wants me to come over and hang out tonight??? Should I???

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