Title: All American Sissy Chapter: One
Categories: Trans, Authoritarian
I'm not sure how this all happened, but here I am, laying in bed with my endowment buried inside another man's ass.
You are probably thinking to yourself, what's wrong with that?
Well, my friends, the tale you are about to read will answer your question.
My life has been pretty perfect for 20 years. I was the only child to a well off family. Model student, athlete, and ladies man. Yes. I said ladies man. Throughout high school, girls wanted me and guys wanted to be me. The perfect all American boy next door. I got good grades and played baseball. I had the typical blonde hair and blue eyes, was 6'4" tall and weighed 180 pounds of muscle and had an ass that almost everyone was envious of.
After high school, I went to a local university on a full-ride baseball scholarship. Maintained a high GPA and dated plenty of girls and got hit on by plenty of guys. I had never thought about men in that way, but it really boosted my ego to have them drooling over me. I reveled in my popularity. I was on track to being drafted by a minor league team. Life was good.
All this changed the summer before my last year of college. I had just turned 21 and gone home to visit my family for the weekend. Things were tense. My parents informed me that they could no longer supply me with extra spending money because they had invested all our money into a failed business venture. I was told that I needed to sort through my belongings to see what I wanted to keep and what could be sold. I was devastated. My childhood home would have to go up for sale to cover the debt my parents were in. I left that weekend knowing that the next time I returned, I would be seeing my parents in a small two bedroom apartment.
For my last year of college, I tried to keep up appearances with my friends that nothing had changed. I picked up odd jobs, here and there, for additional cash. When my friends and I went out, I started letting the guys that hit on me buy me a drink or two. When my friends would heckle me about it, I would just tell them "a free drink is a free drink".
Again, let me remind you, I have always thought of myself as a straight man and never would have imagined myself dating a guy, so all this was innocent flirting.
My final year went well. I kept up my good grades, worked, and played baseball. I wasn't the star athlete, but I was still pretty good. I got scouted by a minor league team and was all set to go after graduation. Life was on the upward swing, or so I thought.
At this point in my story, you are probably asking yourself: How am I supposed to bust a nut to this story. This is depressing. And to be fair, I never promised a story you could pleasure yourself to. I promised a story that would explain how a "straight" all American guy ended up in bed with his 10 inch penis buried deep inside of another man's tight ass.
So...Where was I?
After graduation, I moved to a new city. The team had paid for my move and arranged for me to live in a nice one bedroom apartment in the city with a great view. I loved life. I went to practice, hung out with my teammates, dated girls, and worked out. This was the life I worked for.
My parents were doing better financially as well. We talked almost every day and they were extremely proud. All the time they put in taking me to practices was paying off. I would send my parents money monthly, just to be sure they were living a comfortable life. It wasn't much, but it was something.
When my teammates or friends and I went to bars, I was still getting hit on by guys and I was still innocently flirting and getting free drinks. These city men were a lot different from the college boys that bought me drinks. These men were expecting something in return for those drinks, so I learned how to duck out before they wanted to cash in on their investment.
About 3 months into practicing, I sustained a leg injury that put me out for the rest of the season, with no guarantees of being able to play after physical therapy. That's right. There I was in a new city, trying to live my dream life and it came crashing down. The team kept me on, so that they could pay for my surgery and therapy, but I couldn't afford the apartment, so one of my teammates had me move in with him, until I was able to get back on my feet.
The weeks following the surgery were the worst. I needed help with most of my daily activities, from peeing to taking a shower. Luckily my teammate and roommate, Matthew, was a good sport and helped me out when he was home.
Throughout the ordeal, Matthew and I got closer and I learned a lot about him and he about me. I didn't feel like going out, so we usually stayed in and he would bring home beers for us.
On one of these nights, I mentioned to Matthew that I've noticed that since I moved in, he'd stopped talking about girls. He admitted to me that he'd actually met someone he was really into, but wasn't sure if the feelings were reciprocated. After many more beers and some more questioning, he put his hand on my thigh and looked me in the eyes and told me it was me and kissed me on the lips.
I must have looked confused because he withdrew his hand and sat back. He quickly apologized for his action. I was truly stunned. What gave him the idea that I was into dudes?
I responded that I wasn't gay. He, again, apologized for misreading the situation, as he always saw me flirting with guys and assumed I was gay or at least bisexual. I assured him that I was neither and shared with him the story of my financial struggles and that my flirting with men was an easy way to obtain free drinks.
We ended the night on a good note. No awkwardness or so I thought.
That night, sleep did not come easy to me. It had been a few months since the last time I had sex or wanted to bust a nut. I was in a sort of depression from my injury and loss of financial stability, but that kiss had awakened something inside me.
Over the next few weeks, things seemed to be normal between us. Physical therapy went well and I was on the mend, moving around on my own without the assistance of crutches.
My thoughts did keep going back to that kiss.
One night, as a surprise, I decided to cook dinner for him. I made sure to make his favorite dish as a thank you for helping me when I needed it.
He came home and was pleasantly surprised by the meal. We had dinner and drank and had one of the best nights. In retrospect, this was apparently our first date and I, a straight man, initiated it.
Like I said, we had a great night that included a great meal, drinks, and great conversation. He helped to get the dishes cleaned and then we headed to the living and finished off the 3rd bottle of wine. By that time, it was late and we were buzzed. I hadn't even noticed that his hand was resting on my thigh, gently squeezing. It felt good. Keep in mind it had been months since I've had sex and weeks since the kiss.
I just sat back, closed my eyes, and let him do what he wanted. I opened my eyes when I realized he was tugging at my pants to get them off. Not realizing I wasn't wearing any underwear, my full 10 inches slapped him in the face upon its release from confinement.
He was a little surprised at the size. This was his first time actually seeing my cock. He stared in amazement and then started to worship it for all its glory. I've never had another man suck my cock before, so this was a new sensation. His mouth was so warm and he was skilled with this tongue. His throat seemed endless and he took my full size into his mouth, his lips touching my pubic hair.
I was in heaven.
After what seemed like an eternity, he got up off his knees and pulled me up off the couch and like an obedient puppy, I followed him into his bedroom.
He peeled off my shirt and there I stood, naked in another man's room.
He pushed me onto the bed as he started to undress himself. He straddled my groin and started playfully grinding his firm butt on my very hard cock. His cock was hard and dripping all over my abs. I wouldn't say it was small, but it definitely wasn't as big as mine.
After about 30 minutes of grinding and playing with my nipples, he spat on his hand and rubbed it on my cock.
In my mind, I knew what was about to happen and I wasn't sure I was ready, but all of the sudden, I felt a tightness around my cock. Oh fuck! I was inside of his ass, bare, and without any lube. Before I could protest, he stopped moving. I was balls deep inside my roommate's ass.
Matthew bounced on my cock for at least an hour. Expertly not allowing me to cum. I wasn't sure what he wanted but I wanted to cum.
Squeezing my cock with his tight ass muscles as he bounced up and back down again, I felt like I was about to burst. He asked me if I wanted to cum. I nodded. He told me I had to tell him, so I did. "Please, Matty, let me cum," I begged.
No sooner did those words pass my lips did he bounce one last time. Our orgasms hit simultaneously as I left his ass muscles gripping around my cock, hard, as his own cock was doing a spastic dance and squirting its juices all over the place. On my chest, abs, and even face. I'm not sure how long I was ejaculating or how much, but boy did it feel good emptying out my balls.
As we both came down from our orgasms, he slowly released my semi-hard cock from the depths of his bowels and started licking his own cum off my body. As he reached my face, his lips touched mine and I instinctively parted my lips, unknowing to me, that was his invitation to release the cum he had collected in his mouth into my own. This was my first taste of cum and it wouldn't be the last, but I didn't know it then.
I gathered my belongings and walked to the bathroom to take a shower. Little did I know, that was the night my life would change.
After my shower, I walked back to my room and heard noises coming from my roommate's room. The door was still ajar, so I peeked in. What I saw next was horrifying. On his computer was a video of the events that just unfolded in his bedroom.
I retreated back to my bedroom to find a text message on my phone. It was from Matthew. Just the word "Thanks" and a clip of the video.