The Wingman

My roommate, Kent, was the best wingman I ever had. He was a good looking blonde to my brunette and even though I was in good shape at six foot and 185 pounds, he had a few inches on me with my same weight. Every female I knew asked me about him and I would have been jealous if he weren’t so gracious and such a cool guy. The thing is when he answered my ad for a roommate and moved in I quickly became aware of him being heartbroken over Robin who he had been with for three years.

I was a little shocked as Kent was so funny and outgoing and good looking that I figured his ex must be the hottest babe on the planet. I didn’t ask for pictures, I just let my mind run wild. Despite his breakup he seemed ready to get back into the game quickly and since I was single we became a perfect match. He knew about clubs I had never been to with women far hotter than the dives I hung out in. I quickly became self conscious which was not normal for me but Kent assured me that I fit right in. He even mentioned I was a hottie and should work it. Normally I’d smack a guy for that but I realized that through all the moaning and groaning of pussy under me, very few women ever told me I looked good even though they wanted my nine inches. One woman did say I looked good, like “Saint Germaine”, whoever that is but when I’m pounding away I don’t need to be thinking like a saint because I ain’t.

So bottom line I’d take a compliment from a guy over nothing. Besides Kent was a cool guy except for one thing – he was a Yankees fan. I hate the Yankees!!!!! There are two forms of torture I probably could never take: 1. being covered in honey while fire ants do their work and 2. being told the Yankees beat the Red Sox again. I wanted to hate the bastard for his taste in teams but he had a confidence that I lacked and due to his looks was what some call a babe magnet. Every club we went to I noticed more women than I could imagine coming up to us and the coolest thing about him was when they would do their mutual bathroom disappearing act and we would have to discuss which one we wanted, he always let me have the hot one.

So for our first three months as roommates our weekend routines were the same, going home with a couple of hotties. Normally we’d split up and got to their individual homes for the night but I have to admit I enjoyed the rare nights when we would bring the girls back to our place as the walls were paper thin and we could here each other going to town. I don’t know what Kent was doing in there but the screams were out of control no matter which woman he was in bed with. Both women would have multiple orgasms, probably playing off each other’s screams. As for me it was a guy thing, I refused to let go until Kent did. Now either the bastard was good at what he does or he was trying to outlast me but those nights next to Kent I lasted longer than I ever have in my life.

Knowing Kent could hear me I tried to hold back when I finally allowed myself to come but Kent either didn’t care to keep quiet or couldn’t as his grunts and groans were electric. They always seemed to get both women to shoot off one more time. Having sex in rooms next to each other could have been a weird thing but Kent was totally cool about it. Every morning after it was like nothing ever happened so we kept up the routine figuring why mess with what works. We never talked about it because we never had to.

Things subtly changed about three months into the roomie situation though when Kent went to town on himself on a weeknight. I guess he couldn’t wait for our weekend scoring. I went about my normal business until I realized he wasn’t a quick comer even when he was masturbating. I don’t know what he was doing but his breathing came in quickened gasps that first got my heartbeat pounding, followed by my dick.

Now the thing about being a shower rather than a grower, is that it usually takes physical contact to get me hard. That thing dangling between my legs is pretty heavy. But hearing Kent go at it had me stirring. By the time I had stripped to my boxers and slipped into bed for the night I was almost stiff as a board and I hadn’t even touched myself. Kent’s breathing had moved on to full blown grunts and moans and you would have thought the whore of the century was paying him a visit.

Suddenly I was totally taken by surprise when I heard a loud smack. I had no idea what it was at first but his moans grew along with my dick. Suddenly there was another loud smack and I heard him moan louder than he ever had with our weekend women. The smacks continued with louder groans and moans of “Oh yeah, just like that!” There were no other voices in the room – Kent was smacking himself on the ass!

It was then that I realized I was painfully hard and dripping pre-cum. I reached down and touched a finger to the tip of my cock and had to yank my hand away. I was so turned on that another touch of my dick and I would be making a mess. My cock literally moved about on its own, rising up then smacking back down on my stomach and I wasn’t even touching it! If I hadn’t had several months experience at holding back until Kent got off I would have lost it right then and there without even touching myself.

Kent was getting into it as much if not more than usual and I was not sure what to do with the feelings I was feeling at that moment but suddenly he let loose and it sounded like someone was ripping his guts out. He screamed so loud and long with profanities that I suddenly wished his magical hand was on me. I almost came but held it in check and turned onto my stomach, hoping my weight would force my hardness down.

What happened next totally caught me off guard. He went into a round of heavy breathing, “Oh goddamn that was good!” “Oh my god!” “Man that made me hard!” Things like that. I’ve had the deep breathing after coming before when it was really good and I tried to cover my ears until his pants and moans settled down into slumber but within moments I heard, “I can’t believe I’m getting hard again! Oh yeah, make me hard! Oh yeah stroke that hard dick!”

I couldn’t believe it. I was never quick on recovery but Kent had never gone for second helpings before but his groaning and moaning grew. He was breathing hard and once again an occasional slap on his ass would sound out. He was much quicker to build this time and when he blew I’m sure even the neighbors knew. I almost wanted to check on him to make sure he was okay, except that I wasn’t. I yelled out an “Oh fuck!” that was more spontaneous than anything I had ever felt in my life. It was an involuntary yell followed by a few quick mumblings and moans, I’m not sure what I said but I do know my dick rubbed against the sheets and shot off, a huge load, one big enough to brag about. My gut wrenched and the orgasm seemed to go on forever.

I could care less if I was heard or not, I probably was as Kent suddenly became quiet. I probably would have thought about the implications of what just occurred except, unlike Kent going for round two, I was down for the count.

I woke and showered, getting hard in the process dammit, and wondered how to handle what had occurred the night before. When I finally stepped into the kitchen, Kent was soap scrubbed fresh and in a pretty good mood. A very good mood. Before long we were laughing about the normal things and all I could figure was he never heard me. He was cool that way. Why should things be awkward when you are roommates? Sometimes you’ve gotta do what you’ve gotta do. Not only were things back to normal but Kent thanked me for helping to get over Robin. He was feeling better day by day and that made me feel good.

We took two weeks off from fishing for hotties because we were both suddenly busy with our jobs, besides we were soon going to attending an exotic Halloween ball that we both heard was out of control. Halloween came quick and we dressed as Fred and Barney, allowing for literally nothing but a little fir covering our bodies. I tried to keep my dick at bay as the softness and air circulating around my cock felt very interesting. Kent filled out his loincloth better than I did and I quickly understood why the women chose him first. He was ripped. It was cool of him to always let me have the hotties. I’m sure he knew he could have his pick.

Funny that after thinking how great he was for that Kent finally decided to pick the hottest woman for himself that night. The place was rocking and the costumes were incredibly risqué and erotic. Women were wearing nothing but paint or less and men were flashing everywhere. I saw someone flash who was much larger than me which I had never seen before. I was shocked and held my breath until his plastic dick dropped to the floor. What was underneath was far smaller. Kent loved that and dragged me further into the craziness.

We danced with various women and got grabbed and groped throughout the night. I had more to drink than I usually did and was having a great time. Things changed a little when we were approached by two women dresses as doms in red and black leather. The one in black was the hotter of the two and I naturally gravitated towards her but for once Kent chose and was chosen for her. My lady in red kissed me a lot during our dancing and even stroked me under my clothes but soon wandered after a WWF type in leather. I figured Kent was over Robin and decided to finally go for the hotter of the two.

That left me alone but I managed and soon hooked up with an Asian woman dressed in a manga getup I never heard of but I figured the translation meant, nipples are showing. There was live sex in various parts of the club and I was ready for action. The manga chick went down on me in a dark corner. We soon had an audience and I felt a hand caress my ass as she did her thing. Her mouth was amazing and I forgot about the hand on my ass until it smacked me hard. I thought about Kent that night and suddenly I was rock solid. An ass slap or two later and I was shooting somewhere into the crowd as manga released her lips and stroked me off.

I thought she would want my number but she disappeared in the crowd. A guy in a Zorro mask reached reached for my softening cock and I let him stroke it a few times and let a male suck me briefly for the first time ever before I finally pulled away.

The night ended with me going home solo while Kent brought black leather dom home. That night, our relationship changed forever…