My First Story (hopefully the first of many). I hope you enjoy it!
This story is fiction and all characters portrayed within it are over 18.
Jake is a good friend of mine from high school. Though we were a couple hundred miles apart, he would often come to my school, or I would go to his on the weekends for parties and generally hanging out. We even had worked together for a while, he got me my first job out of school, until he left for a better opportunity. He had recently purchased a house and was looking for a roommate to help make ends meet. After spending a couple of years in an apartment, I could think of no better place to live, it certainly would be nice to have some extra space. It was also nice because he had to travel sometimes for work and we really only saw each other on the weekends, if at all.
He owned a nice house, and it had a home gym in his basement. I liked to take care of myself, doing yoga and working out when I had time. I was proud of the fact that during college I was able to keep myself in shape and not gain the freshmen 15. I was 6'3 about 195 pounds, medium build with a washboard stomach, and a round bubble butt that I was very proud of. It was certainly enjoyable having girls at bars check you out when you were walking past.
We both enjoyed the night life and Jake was a great wing man when going out, when he was around. At 6'6 220 pounds, he looked like he should have played professional sports. Like me, he liked to take care of himself, working out (he had the six pack I could only dream of, and often did) and making sure that he was always dressed for the occasion. I don't think I ever saw a 5 o'clock shadow on his smooth black skin. To say that he was attractive was an understatement. Our typical Friday night (when he was in town) was to hit up some of the bars in town, see if we could meet someone interesting, and see if they wanted to come back to our place for drinks. Sometimes this worked, Jake seemed to have better luck than me, other times I went home tipsy, alone and horny. When this happened, Jake liked to tell me laughing, "You know if you were bisexual, you would have twice as many options to pick up when we went out" typically right after his previous night's score had left the following morning. I usually just brushed off with a laugh and called him a whore. What he didn't know was I had thought of experimenting in college, the fantasy was always there, I just never got the chance to act on it. I got caught skinny dipping once (by my ex that I had recently broke up with) and another time, the guy's roommate walked in before we started. When I watched porn, if I was feeling extra adventurous, I would watch two guys and a girl fuck. There was something extremely attractive about watching a cock slide in and out of another man's asshole. I wondered what dick tasted like and thought of many things I wanted to try before I settled down.
I got home one Friday from work and found Jake putting beer in the fridge. Usually when it wasn't payday and he had just paid a bunch of bills he would want to chill at home, and bullshit about sports, girls, work, or old friends that we kept up with. It looked like this was one of these nights. "Beers later if you want to" he said after I walked through the door. I nodded in agreement and went up to shower after the day.
I undressed and hopped in the shower. I lathered myself up washing all parts of my body, paying special attention to my dick. I liked keeping myself shaven and loved the way that it felt rubbing my hands over my smooth balls. I thought about a friend of mine from college who recently came out (one of the missed opportunities) and a post he had on social media with his boyfriend. The thought of it made my dick semi-stiff. At half erect, my circumcised dick was about six and a half inches long and when fully erect it had plenty of girth, almost an inch and three quarters across. Not massive, but I liked to believe above average. I wondered to myself if a gay man would like my cock, all the girls I had slept with never complained....
After pondering to myself for a bit (such as, would I like to be the bottom or top. Decided on bottom. Though it wasn't a tough choice.) I rinsed off and decided that beers were in order. I went to my room to get dressed and decided I was feeling frisky tonight. I had a secret stash of underwear that I wore when I wanted to feel sexy, even if I didn't show anyone. Tonight was a rainbow jock strap that lifted my butt and made it look rounder than it was. I slipped it on and looked at myself in the mirror. It lifted my butt cheeks and made my round butt look even better. It kept my package all secure and I loved the feeling of openness on my behind. One last look at the mirror and I put some sweatpants on and a t-shirt. I thought to myself, "I may not look sexy now, but god I feel sexy underneath my clothes...."
Jake was sitting on the couch and as he noticed me walk towards the fridge, he asked me to get him a beer. The conversation was the same as always, talking about his job, the new intern they had just hired (he was going to take a shot at her), and asking what was going on at my work (to catch up on his old coworkers). After a few beers had gone down, he asked me about one of my girlfriends in college that he had met. "Did you ever bang her? She seemed like she would have been a freak in the bed." He asked. Jessica. Yeah, she had been. She was the first and only girl that let me do anal with her and she was so good a deepthroating my cock. She said it was her art. She would begin at the tip of my cock, slowly circling the tip making sure to just touch the sensitive parts without providing too much stimulation. She would lick the shaft from one side to the other gently massaging my balls. As she got down to the base of my cock, she would suck one of my balls into her mouth, gently tugging at them pulling my dick up and down giggling as she played. When she decided she had teased enough, often hitting the sensitive parts of my cock off and on, bring me almost to climax and then moving on to the other parts of my dick, the main event would arrive. She would wrap her hand around my cock, underneath my balls and apply just enough pressure to act as a cock ring. Slowly, she would wrap her lips around, at this point, swelling head of my cock taking it all in. Fully engulfing the cock as she moved down, swishing with her tongue as she went. Taking her time until her nose met the base of my dick. She would start slowly at first, but then picking up speed until I could barely stand it. At the last moment, she would release her grip on my cock, and I would shoot my load down her throat. She, taking every drop of my warm salty cum, and me spasming with delight.
Jessica also had been the girl that had caught me skinny dipping with another guy. I had a feeling that we may have gotten back together sometime in the future, we broke up because she was going studying abroad and didn't want to be tied down but catching me kind of put an end to that possibility. Every time I saw her after that (until she left), she never mentioned anything, but she always looked at me with a little shit eating grin. The last thing she said to me before I left was, "I loved my time with you. I think I have taught you enough to be an artist yourself if you so choose to." She smiled and walked away.
"Yeah, she was a good time." I said, hoping to leave it at that. "Someone is holding his experience close to his chest." jested Jake, though he wasn't drunk, you could tell the alcohol was beginning to have an effect. "Hmmm. I think you should open up more. I have an idea. What about a game of truth or dare? I will be 100% honest and complete any dare if you will." I thought his is odd of him, I have known him for over 15 years, and he has never suggested something like that. He got up, grabbed a bottle of vodka from the cupboard and said, "Come on it will be fun. Nothing better to do on a Friday night". Still apprehensive, but also a bit loosened up from the beer I sighed, "Fine I suppose we could play a bit". "Excellent" responded Jake.
We played a couple of rounds back and forth with some pretty civil questions, "Who is the hottest girl at your work?", "If you could bang anyone, who would it be?" and had a few shots as dares. Then one round, in response to my truth, Jake asked, "Why did you never get back together with Jessica after she got back from studying abroad, did she find someone else with a bigger dick?" I responded with, "No. I have a big cock and she was perfectly happy with it. I just never heard from her when she got back". He responded with, "Yeah, sure. That is what it was, I am sure."
"Seriously?"
"Well, why else would she not want to get back with you?"
"I have a massive cock. I bet it is bigger than yours!"
"I doubt that man. You have no idea."
Without thinking, I jumped up and said, "Bullshit!" and pulled my pants down. "How do you like that!" A small grin showed on Jake's face at that point, and he sheepishly responded with, "Do you wear rainbow colored jock straps often or is tonight a special occasion?" At this point I felt the blood leave my face and a realized that my sexy little secret was a bit out in the open. I slowly pulled my pants up and sat back down.
Calmly, and still grinning, Jake responded with, "Well, I will go with truth".
After a moment, I asked, "Why are you so concerned with Jessica and my relationship? What is going on?"
"Well in my travels, I saw Jessica last week and you came up in our conversation. She said something about skinny dipping and you having the tools to be an artist. I also noticed in the laundry a few times, the thongs, jock straps and gay underwear that you seem to enjoy. At first I didn't really think about it, but after I met up with Jessica I began to wonder if my roommate was a bit of a fairy. Maybe he took my advice to expand his horizon to cocks instead of just going for pussy. Sounds like that may have been the case in the past. At least you were trying to. No judgement from me, I have known you for too long for that. Unless you are a pussy, which the jury is still out on. I would judge you for that. You can be a fairy, just not a pussy".
Still wearing his little grin, he finished with, "It is your turn by the way."
