A Long Way From Youngstown Part 1 by Ben G. (benjaminbk2010@gmail.com)
This is a work of fiction - it was written by an adult and is intended for an adult audience.
Questions, comments, suggestions, small talk...all welcome! Locals a bonus! Email me at benjaminbk2010@gmail.com I live in Brooklyn, NY.
This is a series of stories about a man's transformation to a woman - with steps along the way obviously...
Part 1
I grew up in Youngstown, Ohio. My name is Mike Willis. From an early age I knew I was gay. Youngstown wasn't the best place to explore a homosexual lifestyle, so as I grew up I was eager to get out. My parents also helped with that. To say they were supportive of my homosexuality is a massive overstatement. They basically told me to "shape up or ship out." So, once I graduated high school, I "shipped out" - all the way to New York City.
Once in New York I quickly became entrenched in city life. I had landed a good job, made new friends, discovered some great bars, and had begun having some of the best sex of my life. It is New York City, after all. My parents had slowed down their communication and I stopped seeking them out - so our relationship basically died completely by the time I was 19. I was living and working on my own and having a ball.
I was very much out in terms of my sexuality, and NYC offered me many avenues to explore my desires and fantasies. I had plenty of casual sex, experimented in various fetishes, and dated a few guys, one of which for a long time. We may have been in love, or we may not have been. At any rate, it was a stepping stone for me to serious relationships and seeing my sexual desires in a serious way.
One of my main fantasies since I discovered my own sexuality had been cross-dressing an transsexuals. I was fascinated by them. I would attend club parties and tranny strip shows - I would seek out transvestities on dating sites - I even got the idea that I should dress up myself.
I was generally a bottom when it came to sex. I loved sucking cock and I could take one in the ass with the best of them. My hole was incredibly flexible - not saggy or worn-out, but capable of stretching to fit even the thickest and longest of cocks. I dated an older black man for a period of weeks and his tool was fucking massive - so that's pretty much were I got most of my "training," so to speak.
Dressing up and playing the part of a tranny seemed natural to me. I loved and admired sexy crossdressers and TS porn stars that I had become familiar with such as Bailey Jay, Mint, and Kimber James. There was something so beautiful and sexy and exotic about a woman or man with breasts and a penis.
I decided one weekend to just do it - I went out shopping at a few thrift stores to pick up some clothes. I got a few button-downs/blouses, 2-3 pairs of panties, a pair of thong undies, some jeans, a pair of black tights, a tight tank top, some short black heels, and a short black dress. I then went to the costume store and bought two wigs - one jet black with long, straight hair and cut bangs, and the other more of a wavy blonde look. I had to get some makeup too, so I stopped at the Walgreens. This is New York - no one thought a young boy buying all this stuff was strange.
I went home and was so excited that I threw all the items onto the couch, stripped naked, and started dressing up. I was having a blast trying on all the outfits and imagining guys having their way with me. I'm a pretty feminine guy as it is, but it was stunning to me to see myself all made up like a girl. I looked sexy and beautiful. It was a real eye-opener for me.
I put on a pink blouse, tied it up around my stomach, and put on the jeans. I put on the blonde wig and took some pictures. I did the same with the black wig and the black dress. I put some ads on Craigslist. I was going to suck some cock tonight in full dress...for the first time!
Naturally, I got replies to my ad within a few minutes. Some of the guys I recognized but I wanted someone new to try my new persona with...I came across a guy, older, with a thick, beefy cock and hairy balls...my kind of man. He was in his late 50s, stocky, and a little on the dominating side...perfect :) I gave him my apartment # and told him to arrive in 30 minutes. I put on the black dress with black wig. I did my makeup, shaved my entire balls/ass area, put on my pantyhose....and waited.
The door buzzed in exactly 29 minutes. My heart, already racing, took a flying leap. Sure, I'd sucked plenty of cocks, but never dressed as a sexy female slut. I opened the door and looked at him - I was hoping to gauge his reaction. He smirked and walked right in - apparently I looked okay.
"You look terrific....even better than the pictures," he said.
"Thanks, sweetie," I said, attempting my best faux girly slut voice. This would take practice, I thought.
"Well, let's get down to business...I have to be quick." He unzipped his fly and yanked out his cock. It hung there, tempting me. It was indeed thick, and flaccid at this point (which is how I like it - I like to have it grow in my mouth). He touched my cheek gently and said, "Come on baby....suck that cock for me."
I got down on my knees and gently grabbed his cock with my nail-polished fingers and held it in front of me. It was still soft, but starting to grow. I placed my lipstick lips on the shaft and began to suck slowly and sensually, just like I imagined a true slut would. Of course, that's how I suck, but I really tried to imagine myself as more feminine - I was now a crossdresser, after all.
He placed his hands on my head and guided me as I continued to suck. My head was bobbing slowly but deeper now - taking more and more of his shaft into my mouth and throat. His cock was fully erect now as I sucked and sucked. I took breathers every now and again and I could see streaks of red lipstick on his cock....this really turned me on. I made a mental note to video myself doing this next time. His cock was so thick I could barely fit my mouth around it - that made it even sexier.
I unbuttoned his pants and slid them down his legs to the floor - I wanted to suck on his nuts. They were hairy and a little sweaty, which I like. I held his cock shaft up and took each one of his nuts in my mouth in turn, sucking and massaging with my tongue. He moaned more and begged me not to stop.
I then placed my hands on his butt and started really going at his cock - taking it full down my throat. He was loving it. I looked up at him...he was staring at me with true lust in his eyes as I gobbled and slobbered all over his thick man meat.
Suddenly he stopped me - he pulled me off his cock. I looked up at him - he was smiling. I think I knew what he had in mind so I walked over to my couch and seductively inched my panties and hose down just past my ass, keeping my hairy legs covered. I got on my knees, facing the wall, and pulled my skirt up. My tight, shaved asshole was open and ready for business. I heard him walking over towards me, throwing his pants off of his feet as he did so. I could feel his hands touching my back, my legs, my ass...my hole...I felt his hands on my lower back, and I could sense his legs close behind mine...and then I felt the tip of his cock at my hole - still slick with my own spit...and then I felt him enter me.
The sex was fast and furious - he must have been quite close to cumming. He started really pounding my asshole with that thick cock of his. I was loving it. I started moaning like a bitch - a little high-pitched, a little squealy, begging him to fuck my "pussy". He kept up the pace for what seemed like a long time. I could see myself a little bit in the mirror hanging in the room to my left. I looked like a real cockslut in a black dress getting pounded in the ass...it looked hot and made me that much hornier.
"I want to shoot in your mouth, slut," he said while maintaining the assault on my ass. I leaned forward and his dick popped out of my ass. It was twitching and gaping with pleasure. I turned around and laid on my back. I lifted my legs up and began to massage my gaping asshole...I loved that feeling. He climbed partway up onto the couch and started jerking his sloppy cock vigorously - it was aimed directly at my open mouth. He tensed up and started grunting. I was hit with a Peter North-esque load of cum - thick, ropey, huge, and delicious. It coated my cheeks and lips and mouth...I swallowed all I could and wiped the rest into my mouth with my fingers. I gave his cock a few clean-up sucks and then smiled at him. He simply turned away, pulled on his pants, and walked out the door. The only thanks I got was an email a day later with a brief but glowing review. He sure did make me feel like a slut...and I loved it!
My journey would continue - this was only the beginning. The discovery of my feminie side, my love of cross-dressing, and my love for all things tranny would keep me pursuing my ultimate fantasy of becoming a woman....
To be continued!