Adult Youth, oral anal, b/MMM
This story is a work of fiction and contains descriptions of explicit sexual acts between a consenting youth and an adult male and as an adult with adult male. If this type of content offends you or you are under the age of 18 do not read it.
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You may contact me at pomowolf74@gmail.com if you like. All flames will be ignored.
Jonathon dresses as Joan By Wolf
The first time I actually-had anal sex with an adult male was after making a date with a fellow cross dresser. I had always wished that I had been born a girl. I had very feminine looking features. My platinum blonde hair would eventually darken to a brown color. There was a neighbor family where the children were grown and the youngest girl was away at college.
The parents were in their fifties. They looked like a couple of comfortable older couple that no one would ever suspect that either of them would have prurient interests, but the husband took an interest in me because he thought I was such a pretty boy. I was a slender ten-year-old and he was thrilled to have my company. He was always telling me how much I reminded him of his daughter.
He told me all about the trunks in the attic full of the clothes his daughter had outgrown. He invited me to follow him upstairs to check them out. I found the attic to have been turned into a girl's bedroom. There was both a hope chest at the foot of the bed and a steamer trunk in the room. Trew to his word, they were full of his daughter's outgrown clothes. He encouraged me to try them on. He even helped select attractive outfits for me to try on.
We played dress up games for a few days before started having me sit on his lap and he started kissing me and playing with my stiff little penis that he pulled out of her tight little panties. That led to us sucking each other's penises. It was all very thrilling and we carried on for years, but he never showed any desire to indulge in any anal activity. My family eventually moved to another town.
I continued to be fascinated with cross dressing and continued to find ways to procure girl's clothing to fit my age of maturity for the time. I continued my cross-dressing activity while in college. I enjoyed showing off for older men on my computer and masturbating for their benefit.
One evening I hooked up with another crossdresser about my age. At the conclusion of us milking out dicks for each other's benefit, we agreed to meet at his apartment. We drank Champlain to break the ice before we opened our luggage and compared each other's taste in clothes. He was more the fashionable tramp, while I prefer the innocent college school girl. She preferred to be the aggressor and sat on one of the chairs in the front room and had me sit on his lap while she felt me up and kissed me very passionately with tongue. She even bit my lower lip, while she fished mt penis out of my creamy white nylon panties and ski fully masturbated me until I squirted cum all over my pleated skirt. I assumed that I was expected to get on my knees between her legs and suck her clit until she fed me her cum, but she had other ideas.
She had me stand and she got up and led me by the hand to the bedroom and has me lay on my back in the middle of the bed and she reached under my skirt and grasped my pantyhose and ripped them open to get at my sissy asshole. She removed the wrap-around dress exposing that all she was wearing was a B cup sized bra and matching black bikini panties and held his own clit tightly against her body. Noone would ever suspect that she was sporting a six-inch cock. She lifted my legs up by the ankles and placed my heels on her tits and guided her clit to my boy pussy and forced it into my colon and proceeded to take my cherry. When he started to achieve his orgasm, he pulled out and cream pie my ass and came all over my external overs and my own clit. I had been crying like a baby the whole time she was fucking me. When she was finished cumming in my ass she licked the tears from my face. Before we bathed and cleaned the makeup from our faces and changed back in our male attire and packed up and left the apartment.
The next guy I made a date with became a problem for me. I met him at my motel room. He did a good job fucking me, but the next time we meet he face fuck me with his huge 10 to 12-inch cock. I was forced to swallow his whole load that night. We were in the 69-position with him on top of me. I enjoyed the sex even though my throat was sore for days. I had a firm wedge pillow and he put me over it and fuck me hard and deep twice. I accepted that that was the way he wanted to fuck me and always did it twice. He wanted me to cross dress for him and to meet his dog and his girlfriend. but I never got around to doing that, plus he got obsessed with me. I had to threaten him to leave me alone.
I eventually met another guy that was a white dude with a huge thick monster of a 12-inch cock, plus he had the amazing ability to stay hard to fuck my ass until I begged him to stop. He would take me to his place and fuck me and make me suck him off. I was hoping to try bondage with him. but he got mad because I never help with travel expenses.
I sucked another man cock before I moved to another apartment that happened to be closer to him, so that we could hook up more often. I was thrilled to suck his cock and the feeling of his 12-cock in my sissy pussy. I even learned to endure enemas to make it easier for him to fuck me. He gave me a butt plug to wear when I was not with him to stretch my sphincter. I took to wearing body stockings that were crotchless, and maid outfits more for his pleasure. He would spank my ass so hard once it left a mark on my ass that I still have.
Another time he put me in a body wrap and fuck me and left me on his bed after he pissed into my colon to suffer in silence for the want of a shit. He would fuck me while I was still in the wrap and use Duck-tape to close the hole and let me suffer for an hour or so before doing it over-and-over again. I eventually had an explosive bowel movement that soiled the bed so badly that the mattress had to be replaced.
He became my Daddy. I would suck his cock in public: in parking lots, restaurants, and theaters. I would go home with his cum on my face. Several times he would cream-pie my sissy hole in public. One time we were making out he talked me into going to an apartment and made a few phone calls to invite friends to come over and participate in a gang banking me. Daffy put his cock in my sissy hole and his friends fucked is ass and our mouths. Guys were standing over us jacking off and squirting cum all over our bodies. When it was over I was consumed with guilt, and his wife found out about what he was doing with me.
I haven't been able to find anyone since then, plus I moved to cedar park, Texas.
If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to pomowolf74@gmail.com
If you enjoy Nifty, please make your donation to Nifty Archive Alliance to help keep the site running and stories available.