Gary

Then there is Gary. Backstory: I was living with Betsy and Jim in a two bedroom apartment. During the summer after my first year at school, I needed an apartment, Jim needed a roommate. We worked together at the mall, so he asked if I wanted to move in. When school started back, I decided to stay in the apartment and skip the dorm.

David and I went our separate ways from there. Shortly after school started, a friend of Jim's, named Betsy needed a place to crash. She started sleeping in my king bed as a matter of convenience. She was married, and her husband was still living in CA. I wasn't that attracted to her. She was a hairdresser and a little wild. I was slightly afraid.

Not long after moving in, October time frame, Betsy came home drunk. And horny. After an hour of drunk sex, she passed out. In the morning, she awoke and apologized.

I said it was fun, and not to worry. She then asked if it could continue. She was always horny, and she couldn't stand it seeing me walk around half naked. I figured if she was OK with her marriage vows, I was cool with it. She was trying to figure out how to lay me since she moved in.

Jim announced he was out of the closet at Christmas time. Betsy pulled me aside and told me, thinking I might 'freak out' that Jim was gay. My response was that I had no idea he was IN the closet, considering how flamboyant he was. And that I didn't care, it was cool. She didn't know about David and I wasn't about to tell her.

As a gay man, Jim was sort of flaming, and it was not a big turn on to me. Plus he had more hair on one square inch of his chest than I had on my whole body. Totally not into him at all, but he was OK as a roommate.

With his coming out came gay friends coming over. There was a gaggle of them, and they were all nice, but I really was not into the gay scene. There was Antoine and Stephan, the inter-racial couple, and there was Jeff, a guy that went to school with Jim. Betsy liked to go to the gay bar with them, as did Sue, I guess you would call her a fag hag that started showing up as well.

They seemed to be over at our place a lot after they were at the bar. I worked two jobs plus school, so hanging with them was a luxury I never really afforded. I went out maybe a dozen times. Jim started bringing home some guy from South America, Philipe. He spent the night every once in a while for a few weeks. He was so quiet, he never really talked much. Not sure if it was language or shyness, but he was the opposite of Jim. After two months, he never came back. Jim said he had to go back home to South America.

If they went to dinner and I was off from the mall job, I usually went with them, the restaurant we hung out at was next door to the bar I worked at, and I could catch dinner before work. It was one of these occasions that Sue was bringing Gary to meet Jim after Jim's break-up. Gary moved back to town from another state, to get a job cutting hair in town. There we were all drinking, eating and chatting when he walked in, and immediately you could tell, Jim and Gary were not going to be a couple.

Jim was flamboyant, but seemed to like his partners quiet. Gary was the opposite of quiet. As a hairdresser, he had this long wild mane of hair, with many colors to it, mostly dirty blond with several different streaks. He stood about 5'6" or so, with a very trim build. He had blue eyes and a nice looking face. He was very open about his gayness, and there was no question he was out. But he had a very quick smile, and a sparkle in his eye.

We all sat at two tables the 8 of us plus a few other friends, all to meet Gary, and he ended up sitting next to me. Everyone knew Gary was being brought to meet Jim. had no intention of doing anything with Gary. That part of my life was not something I was pursuing, besides, sleeping with Betsy was going great.

It was a no strings attached situation that I had no intention of changing up. There were really no guys in my life since Dave, and really, I had a good thing with Betsy, unattached sex when I wanted it. But for some reason we chatted a lot more than some of the folks thought we should have.

Looking back, I often wondered if I was the roommate that Gary thought he was being introduced to, and not Jim.

I wasn't really interested in getting to know him sexually but he was fun to be around, a little impish.

It was a great dinner and we all had fun getting to know Gary, except Jim, who was disappointed he wasn't what Jim was looking for. Or he was miffed that Gary seemed to glob onto me. I was just talking to him like the others, oblivious to what was happening.

I agreed to help him get his license in our state by driving him to the capitol when it fit my schedule. That was when the interesting stuff began.

Gary and I drove to the state offices later that week, and stopped and had dinner in the big city before driving back to the small town we lived in. We had an interesting talk about who knows what but neither of us stopped or got bored. On the way home, he pushed the arm rest up and sat close to me and started stoking my thigh.

I asked him what was up, and he stated he was thanking me for the drive, since he couldn't afford gas money. Instantly my dick started getting tingly and rising to the occasion. I lied and said I had never been with another guy before, and he said, that was great, he wanted my first time to be memorable.

He kept stroking my leg and inched closer to my crotch, noticing my bulge and gently rubbed that as well through my jeans.

"Wow, that bulge is even bigger when it is ready for fun" he said. I am a little bigger than most of the guys I have seen. At six and a half feet, weighing 240, I am pretty sturdy, and have a swimmers body. I swam and played basketball in high school and still swam as way to keep in shape. But I was anything but small. Fully erect, I think I am over 8 inches, but don't care to measure.

It all feels good no matter what size. "When I saw you get up the other night, I saw this bulge, I had to have it." Gary said. I moaned in response to him still rubbing me through my jeans. He reached over, unbuttoned my pants and opened as best they could while I kept driving, and started rubbing my cock and balls through my underwear.

By this time I was fully erect. He slowly peeled my underwear back, and my cock sprang fee, the blood straining against the skin, I was so hard. He bent over and took my dick into his mouth. It was very warm and soft, for a guy, I thought. He started kissing at the base of my cock and worked his way up the length. It was sending shivers through me as he teased the head and worked his way back down.

Meanwhile, he had his hand on my balls and was rubbing them, and working a finger underneath them and tickling the taint. I spread my legs as best I could in the drivers seat.

He sucked and licked and stroked until he had me close to the edge. I finally had to pull over as I couldn't concentrate on the highway any longer. I leaned the seat back and he kept sucking as I started grinding my pelvis up to his face.

I finally let loose with my load, into his waiting mouth. I sent rope after rope of cum down his throat. I don't think he missed a drop. He sat up, and kissed me with some of my load still in his mouth. It was very intoxicating, as he deep throated me with my own cum. Afterwards when I dropped him off, I planned on driving home and sleeping with Betsy.

But as we sat in the car at his driveway, and he went to get out, he said, "C'mon too, I'm not done. I want that dick of yours stuffed in my ass." I instantly got hard.

When I fucked David, it was sort of a begging thing and he wasn't that into it. This guy wanted me inside him, and that made me hot, and I was eager to try anal with another guy again. I shut the car down and went in with him. He didn't have to ask me twice.

He led me to his room, and we started kissing, slowly at first, but soon with more passion and urgency, as he started taking off my clothes to reveal my extremely rock hard cock.

He got me totally naked and pushed me down onto his bed. As I sat and watched, he undressed. This is the first time I any part of him nude. He was smooth, with very little hair anywhere. He wasn't athletic, but he wasn't flabby either. About the only pubic hair he had was a small patch right above his dick, which was much smaller than mine, but then, he was way smaller than me by almost a foot and a half. He had very smooth, small balls. I reached over and started stroking him. He closed is eyed and moaned.

He moved closer and I bent down and took him in my mouth, and started sucking him. As this was my second guy ever, I am not sure if it wasn't very good for him, and I tried not to get some teeth in the way, but he seemed to enjoy what I was doing. After a while of sucking and kissing his cock, he then climbed up on the bed, laid down, spread his legs and pulled me up.

We ground our dicks together as we kissed for what seemed like forever. He reached down and grabbed both our cocks in his hand, and we started dick fucking. We were both breathing heavy and kissing hard. He let go of our cocks, reached over to his night stand and grabbed some lube, put some on my dick and stroked me as he got me lubed up. He handed me the lube and whispered, "Finger me."

He pulled his legs up exposing his pink smooth hole. I then put some on my finger and started working my finger in. I slowly finger fucked him while cupping his balls in my hand, going to the first, then second knuckle. He was moving his hips, meeting my finger and gently rocking. I got my second finger up to the hole and started working it in as well and we kissed hard, and he said, "Now your cock, please. I'm ready, fuck me."

I moved down on his body a little, and rubbed my cock some more to get lube all over it, and I pushed my purple cock head up to his anus and pushed ever so slightly. He reached down, and guided me in. It took several tries to get the head of my dick past the hole, but once in, I rocked slowly as he guided me till it was all the way in.

We started kissing again, and I slowly started moving back and forth. It's not like a pussy, where you want the clit to be stimulated, and he shifted around till he had me where it felt good for him, and then said "Harder, fuck me as hard as you can." I started thrusting harder and harder, slamming my cock deep into his ass. My balls were slapping against his ass cheeks in a frantic rhythm.

I was enjoying how tight his ass felt around my cock. It was so hot; we were both sweating and panting and moaning. He finally started stroking his dick and yelled he was about to come. He wanted me to come with him. I thrust a few more times and heard him moan and felt his cum spray up on both our stomachs, and that pushed me over the edge.

I think I dumped ten ropes of cum up his ass. I slowed down my thrusting as the waves of my orgasm subsided, and after a few minutes of enjoying myself, I lay down on his chest and planted a huge kiss on him, as his cum and our sweat merged between both of us. I finally slipped out of his ass as I softened, and we lay together holding each other in after glow. we wiped each other off, kissing and fondling each other in silence as our breathing returned to normal.

The next day I lied about where I was to Betsy and was waiting till the next time I could see him, and it was killing me to not just be over at his house. I finally got a chance to go to his house under the pretense of needing to get to the library for school.

I went over to him and we were on the couch and I was just done giving him head when his young sister walked in on us. Gary was hot looking in his own way, but his sister Emily, was smoking, even in pajamas. Emily is my next story.