My Roommate Jake

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."

It took me a moment to take it all in. "Not a pussy? No judgement. Artist? Hmmmm. I wonder." I thought to myself. At this point I realized that I don't think I have much to lose at this point, and responded with, "Dare".

"That a boy! Ok. Well, since you enjoy that underwear so much, why don't you take your sweatpants off and your shirt".

I slowly stood up and began to remove my clothes. Jake responded with, "Maybe your dick isn't that small after all, but it still isn't as big as mine." When I had finished, Jake made his choice, "Dare".

"Fine if you say your dick is so big, why don't you take off your clothes then?"

Grinning, Jake responded with, "You would like that wouldn't you? Fairy." And with that Jake stood up and removed his shirt. I had never really looked at him or his body for a long period of time in fear of being caught. I took it all in. His six pack. His perfectly trimmed body. I could feel the blood in my dick starting to flow.

Looking down at my crotch and as he began to pull his pants down, he teased, "You seem to be enjoying the show, wait until you see this". With that, he pulled down his pants, and I counted as they dropped. One inch, two inches, three inches.......... seven inches, eight inches, nine inches.

My mouth dropped. As I stood their wide eyed, I came to the realization that I thought all of the blood in my body was now in my cock. Jake took notice as well, smirking, "I think someone likes what they see. I think that we should stop playing with truths at this point, if you are ok with that?" I nodded in agreement, still awestruck with the beautiful big black cock that stood before me. Nine inches long, as wide as mine. It was beautifully shaved, in fact Jake seemed to have shaved all of his body hair off of his body. I looked so smooth and soft. "Well, I have a dare for you." Still smirking jake said, "I want you to take off that jock strap. It is cute and fits you nicely but think that it may come in the way of other activities in a bit." I did as I was told, not hesitating and anxious for what was to come. My heart was pounding, and I could not stop staring at what I was seeing.

A slowly stood up and did what I was asked, pulling down the jock strap letting my rock-hard cock free from its containment. I could feel Jake's eyes going up and down my body, clearly enjoying what he was seeing. "Good to see that you take care of yourself and that you like to keep yourself well groomed." He said as his eyes stopped at my rock-hard cock.

"Yeah, it was an interesting conversation with Jessica. She thought that you had some desires that she didn't think she would be able to help you with." I did have desires, but I had never really put it into words, just thoughts. Looking at Jake's cock helped with that.

I wondered what it would be like to have his cock in my mouth.

I wondered what it would be like to be a cocksucker.

I wondered what it would be like to let my gay side shine and be the fag I always knew I wanted to be, even just for a little bit.

Even wanting to experiment during college, I had never put labels to it.

I wanted to be a cocksucker.

I wanted to know how it would feel to have his shaft in my mouth. Sucking the tip of his cock, using my tongue to take it all in. Pleasuring him with my mouth until it was too much to bear, and he released his load into my mouth.

I was a cocksucker at heart.

Being able to put these feelings into words surprised me, though I knew they were the truth. My earlier thoughts came back into my head, I did decide I would be a bottom when I was in the shower. Would it be time to possibly explore this side of me as well? I came to the conclusion that only time would tell. I had to see how far Jake would want to go, though I was pretty sure that I would be willing to do anything at this point.

I got up and took a pull of vodka from the bottle, deciding that this would help with my resolve. At this point Jake asked, "Well I suppose it is my turn for a dare... what are you thinking?"

Feeling the liquid courage starting to hit me a bit more, I finally decided to let my desires take control. "I dare you... to let me take a closer look at your dick."

"You can get as close as you want." Smirked Jake.

As I moved closer to Jake, my anticipation, my curiosity, and my desires rose. I wanted to have this stallion of a man make me his dirty plaything. I wanted nothing more to move my hands up and down his body, to truly appreciate his male physique, and to pleasure him with all of my might.

Jake, still sitting on the couch, relaxed a bit as I came near and opened his legs a bit to allow me to kneel down. I gently took his cock in my hands and began to stroke the shaft up and down. Something just felt right about this. Watching the skin of his cock moving up and down in my hand, his balls jiggling up and down, the musky smell of his crouch wafting through the air. I could feel his cock stiffen even more in my hand as I jerked it up and down. What a beautiful cock!

"I think you know what dare I am going to choose next, but I think you need to earn it." Jake states as he looks down on me. "I dare you to tell me what you want to be and what your deepest desires are."

"What do you want me to do?" I asked looking up at him.

"Say, what you want to be. Admit it to me and let it out in the open."

"I want... I want to be a... I want to be a cocksucker." I barely whisper.

"Louder. I didn't hear you.

"I want to be a cocksucker. I want to suck your dick."

"Oh really? Do you want to be my cocksucker? Do you want me to cum all the way down your throat? Do you want to be my cockslut?"

"Yes.... I want to be your cockslut." As my mouth started to water and my erection grew stiffer.

"I think I am going to enjoy this." Smiled Jake as he moved my head closer to his cock. Rubbing his tip over my cheeks and lips, spreading the precum leaking from the tip of his penis all over my face.

Not being able to take it anymore, I finally opened my mouth and took the tip of his cock in my mouth. Using my tongue I began to swirl the tip all over in my mouth, doing my best to imitate what Jessica used to do to me. Applying a bit of suction, I finally took his shaft deeper into my mouth, making it down 4 inches on his cock. "That's right cocksucker." Jake said," Let your wildest fantasies come true. You may not be able to take all of my dick right now, but we will work towards it. You will be my personal faggot in no time. Let the cumslut come out."

I grinned as I was called these slurs, coming to the realization what he said was true. I removed his cock from my mouth and ran my tongue up and down his shaft gently licking his balls every time I went down.

This continued for what seemed like eternity. My sucking on Jake's cock, taking more and more into my mouth, only stopping and licking his shaft and balls when I needed a moment to recover. I finally adjusted my angle and made it further and further down. As my nose rubbed up to the base of his cock, I finally had managed to take him all in.

"God damn you really are a cockslut. Not too many people have been able to take me all in. Fuck that is amazing. Jessica really did teach you her art" said Jake as he pulled my head up and looked me in the eyes. "Let's go faggot, I want to repay the favor."

With this said, we got up and walked to his bedroom. As we entered, he turned around and pulled me in close. We locked lips and had one of the most passionate kisses I had ever had. Both of our tongues exploring each other's mouths while our cocks rubbed against each other.

Jake slowly pulled back and pushed me on the bed. "You are not the only cocksucker that lives here." As he gave me a wink. I was much more sensual in my cocksucking compared to Jake, wanting to enjoy every feel and taste as his cock explored my mouth. He on the other hand went at it with a fury. A few passes with his tongue on the tip of my cock and then he went at it, bobbing his head like piston in a car, up and down, up and down, taking my full cock in almost his first attempt. Something told me that he had more experience than what he led on.

Not wanting this to end too quick, a few moments later I slowed him down, looked him in my eyes and told him, "We don't want to have this end too quickly. There is one other thing I would like to do tonight."

Grinning Jake quipped, "Just one?" He then started to shift his body. Rolling on top of me, putting his ass and cock right over my face. "Well, I think you should go back to sucking my cock while I take care of some business down here."

I didn't need to be told twice. I shifted his cock downwards and took it in my mouth. I was giddy at this point, loving the fact that I was sucking a cock with no hands needed to guide it. My eyes got wide with anticipation, when I felt Jake pull my legs back, exposing my asshole. "I think I will have to pop this cherry tonight." I could feel Jake's warm breath as he got into position. And then slowly I could feel his tongue work down my scrotum down to my rosebud. He worked his tongue slowly at first, going up and down my scrotum and crack with the full width of his tongue. He finally stopped at my rosebud and began to tongue fuck my hole.

Oh my god what a sensation. I began to moan out loud with pleasure. Jake snapped me back to reality, "Oh you like that do you? Wait until you feel my cock in your ass."

With that, I felt like a man on a mission. In this predicament, a very gay faggot man, but with a mission none the less. I became focused on sucking his cock with reckless abandon. I wanted to make sure he was good and hard for what was going to come next.