My First Time (with a guy)

After my first disastrous date, I got better about crafting more specific ads and being more careful about being picky and careful about getting clear pictures before agreeing to go on dates with guys I had met online. Ideally, I would have had other options besides online dating to meet guys, but I'm not a bar person and I have horrible gaydar so it isn't like I can just meet guys on the street.

Over the span of a couple of weeks, I went on more than a dozen first dates. None of them had any appeal to me. I started to think, maybe I am just a kinky straight boy. The guys were mostly nice, but I just wasn't feeling anything for any of them. I'm very athletic and am pretty attractive. I'm used to being around good looking people so I was dissapointed going out with guys who said that they are fit but weren't and had little to talk about other than their sexuality. It's great that there are a bunch of gay organizations (and I have become involved to a degree with some of them), but it is sad to me if that is your whole life.

Anyway, it had been roughly two months of dating boys and I still hadn't had so much as a kiss. I was frustrated. I had emailed this ridiculously good looking guy on gay.com with a bizarre profile. His profile was so strange that I didn't think it was real. A couple of days later, I got the gay.com messenger working for the first time (I didn't have Java installed on my computer so it hadn't ran before). When I logged on, he started chatting with me. I was in shock. We had a long conversation through IM (which I hate...) and made plans to get together.

For some reason, I thought that he was just interested in being friends with me. He's a huge fitness guy and I do some pretty out there and challenging physical things so I thought he was interested in being friends with me. I had told him my background and he gave me a little advice and indicated that he could give me some more. I offered to cook him dinner that week and he got excited and thought that sounded fun.

At this point, I wasn't sure if this was a date or if I was making friends. I cooked a seven part meal (yeah, trying too hard...), put music on that was more fun than cheesy romantic, lit some candles, and lit a fire.

I finally heard a car and looked out the window into the cul de sac and saw a really attractive guy walking towards another house. I opened the door and looked at him on my neighbors porch. He saw me and came heading over. He was VERY attractive. Like just walked off the cover of Men's Health attractive. He was wearing shorts and a tank top. He was puzzling to me. Hearing him talk, he was obviously gay, but he had a masculine voice and presence at the same time.

We shook hands and he seemed very excited about the food. He started off by telling me that he had just accepted a job offer in another state. I was pretty bummed, but figured that it would be fun to talk with this guy and that I could make an out of state friend.

He was very impressed with the dinner and then I brought out dessert (from scratch brownies and homemade ice cream-- yeah, too much, I know...). After dessert, he motioned me to follow him to sit over on the chairs by the fireplace. He sat in a chair by the fire place and I sat on the couch (kind of dissapointed that he wasn't sitting on the couch also).

He said something like, "so what do you want to know about dating guys and having sex with guys?" We talked for hours about everything. It was really fun. At the time, I had one gay friend, but he didn't know I was attracted to guys at the time and we had never talked about sex or dating. We also talked about fitness, travel, etc. It was a blast.

Eventually, it started to get late and he got up to go to the bathroom. I assumed he would leave when he was done. I was surprised when he came back and kneeled down in front of me and took off my shoes. My heart almost burst. He then sat down on the other side of the couch and smiled.

We did this cat and mouse thing for a while. He put a foot on my thigh and I took off his shoe. Then the other foot. Then he pulled one of my legs up and sat it on his lap. Then the other. We didn't stop talking though and each of these things happened about twenty minutes apart. He was letting things move slowly at my comfort level. He started rubbing my feet and commented that my heart was pounding. We started rubbing each others feet.

Eventually, I asked if I could rub his back. He said yes and took off his shirt and laid across my lap. We were both about the same height (just under six feet) and both slabs of muscle. He's of Russian descent with dark blond hair and blue eyes. I have brown hair and eyes and more olive skin. It seemed like a nice pairing.

My hands dove into his back with as much as I could throw at him. He liked rough strong pressure and moaned a little. Eventually he rolled a little to the side and tilted his head up to me. I leaned down and he kissed me aggressively. I remember being surprised by feeling his stuble and how rough his skin was. He wrapped his arms around me and I can still remember feeling both of our hard bodies grinding into each other. He squeezed me really tight and moved until our whole bodies were pressed against each other. I felt his erection pressing through his shorts and reached around to feel his ass. We rolled around almost like we were wrestling. He pulled my shirt off attacked me. He was very aggressive and I liked it.

Eventually, I went for his zipper and he said that this is what beds are for. I stood up and then picked him up which seemed to shock him since he was close to 200lbs. I picked him up and started walking to the bedroom. Then I pushed him up against the wall and started grinding against him and groping his ass. From there, I picked him up again and carried him to the bedroom.

I took off his shorts and my jeans. I was surprised and kind of freaked out that he was wearing bikini briegs (gag). He probably felt the same way about my jockey sport boxer briefs. I threw him on the mattress on his back and looked down at his erection. It pointed straight up against his body. I got down and had one of those now or never moments as I grabbed it with my hand and guided it into my mouth. I was surprised by the texture and the lack of odor and taste. As I sucked on him, he eventually let out a little blob of pre-cum which caught me off guard. It actually felt rubbery in my mouth. I was also surprised that I didn't gag or have any problem fitting the whole thing in my mouth. It seemed roughly normal sized.

I went to town on it and then licked his balls. What I lacked in skill and experience, I made up for with sheer enthusiasm. Continuing the licking, I pushed his thighs up to his chest. His tight ass cheeks spread and I eyed his fuzzy asshole. I decided "what the hell" and dove in with my tongue. He seemed schocked in a good way and started telling me that he didn't know how much longer he could hold out. I licked him for a while and he grabbed himself to beat off and I smacked his hand and said, "that's my job." I was channelling my inner porn star... I switched back to sucking him and tried to put a finger in his ass. He commented to be careful so I pulled it out and just teased the outside a little. Pretty soon, he shot in my mouth. I was surprised that it had very little flavor (which I would later learn isn't the normal case...).

I swallowed (I figure that I always liked it when girls did for me) and crawled up him to kiss him. He commented that he didn't believe me that I had never done this before. I told him that it was my first time. Then he commented that I was an advanced student and that I must watch porn. He commented about the rimming and me being able to, as he said, "deep throat" him. He told me that I could eventually train my throat mucles to attempt to swallow and that can stimulate a guy. I felt like "one thing at a time..."

I asked him if I could jerk off on his chest and he said of course. He laid next to me and started to stroke me but he was really rough and tried bending my cock in bizarre ways that didn't feel good. I took over and he played with my nipples and kissed me. I felt self-conscious so it took me forever which meant that by the time I came, I exploded all over him. Then we rolled around making out with the come making things slippery.

Then he got up and we both realized that it was 5:30. We had been up all night. He cleaned up and got ready to head out.

At this point, I realized I didn't know his name (He had said it when he walked in, but I had forgot it). I also didn't have his phone number. I had this weird feeling that I would never see him again. I asked if he wanted to go out again and he wrote his name and number on a piece of paper. I felt relieved. It was important to me that this not just be a one night stand.

I sent him email the next day saying that I had a really nice time. I waited two more days and didn't hear from him so I sent another email expressing that I was dissapointed not to hear from him. He IMd me that night and chastised me for the "harassing" email. Eventually, we made plans to go out the next weekend.

I was beyond excited. I made reservations at a nice restaurant and got tickets to a play. When we met at the restaurant, he kept teasing me. At first it seemed okay, but then it just seemed like he was doing nothing but putting me down. We were sitting on a balcony and when we were getting ready to leave, he grabbed a handful of food and tossed it down on the people seated on the main level.

I should have ended the date, but I was in shock. We went to the play and he put down the play and mocked a bunch of things. He started telling me about the other guys he had hooked up with and about this group he is involved with for groups of gay men to get together and jack off together. There was an older couple sitting next to him and he seemed to be saying the things to shock them as much as me. At the end of the play (which was fantastic) everyone stood up when the main actress came out for her bow. He just sat in his seat and didn't even clap.

We walked out and he said that he was tired and wanted to go home. I said okay and spun around and walked away. He chased me and gave me a hug and told me that he wanted to go out again. Then he looked at me and said, "you don't even know what to say when you don't have cliff notes." I got in my car and started to drive. I realized that my body was shaking. I felt so dissapointed and hurt. I had gone like five days without jacking off, read reviews of the play, and put forth a lot of effort. I was also just really excited to see this guy. If he didn't want to see me, I don't know why he agreed to go on the date.

I got home and had this weird suspicion that he was online. I checked and sure enough, he was online on gay.com. I started to ask him about the evening and if he hadn't wanted to see me why did he go on the date. He insisted that he had fun and wanted to go out again. I started asking him questions and told him how dissapointed I was. Then I mentioned that I had gone five days without masturbating for him. With my dignity gone, we never communicated again. Too bad I did't just leave it as a one night stand...