On which date do you have sex with a new guy?

Having spent most of my life dating women, I'm pretty surprised by how different this is when dating guys.

With girls, there is kind of a preconceived notion that if a girl sleeps with you on the first date, she isn't relationship material. This may be antiquated and many people might not abide by this, but this does seem to be the general mentality. Boys will of course sleep with a girl on the first date if she is willing, but then they will discount her potential and wonder how many other guys she has done that with. Girls know that this is the mentality and delay things a bit.

I think that there is an advantage to waiting. We live in an instant gratification society. It is nice to actually get to know someone so that you can feel comfortable with them and be invested in the experience. I also think that having sex with someone makes you think that you know them better than you actually do. It can lead to a false sense of intimacy.

All of that said, it seems like the norm for gay dating is to sleep with someone on the first or second date if you are ever going to sleep with them at all. Maybe not full on intercourse, but at least a hand job. The guys that I've really liked but tried to delay sleeping with (because I really liked them...) seemed to dismiss me and cite a lack of chemistry. I wanted to resist this but I've since come to the conclusion that this is just kind of how it is. My gay friends say that it is basically the norm.

Given that you haven't had enough time to impress the person via your personality and other compelling attributes, I sometimes feel like the first time I have sex with a guy is a bit of a performance. If I like him and want him to keep going out with me, I have to really show him a good time. In general, I feel like I am so focused on pleasing the other guy that I don't even worry about having a good time my self.

It becomes too much like a performance. I'll go a couple of days without jacking off so I can bust out some massive load. I have strong hands and good touch so I'll flip him over and show off my massage skills. I'm always the first one to suck off the other guy and rarely ever get sucked on the first date. I usually dictate what happens as it seems most guys in Seattle are pretty passive sexually and looking for someone to take charge.

It will frequently take me a day or two to even come to an opinion about the guy. It's usually the third date or longer when I start to relax and enjoy the other person enough to really have fun with having sex with them (or realize that I'm not really interested in this person).

In some ways, I guess gay dating is more progressive in that it acknowleges that sexual compatibility is important and puts it on the table upfront just like all of the other traits that you are using to evaluate a person. However, just like everything else in dating, I don't think you get an accurate view of what things will really be like with someone once the initial lust period calms down. For me at least, it is also more fun to have more invested in the person I am having sex with.

I guess all of this stuff is on my mind since I started dating someone recently and had sex with him on the first date and then had a long, romantic second date and didn't have sex at the end. It made me stop and think about this stuff a lot more. I had actually been upset about not having sex on the second date since we had on the first date. I have since found out that he was pretty sick and toughed it out since he wanted to go on the second date with me but was tired after the marathon second date. It made me think about my expecations and thoughts about all of this.

Where do you meet date worthy guys?

I wanted to toss this out there since I'm still pretty clueless about this. It would be nice to hear specifics from people in the Seattle area, but general suggestions are nice too. I've been dating guys for eight months now. Pretty much everyone I have gone out with have been guys that I've met online.

I live in a house in a neighborhood. Seattle has an area called Capitol Hill which is the gayest part of town, but it is a relatively integrated community so gay guys are all over. I joined a gay sports league and have become involved in a gay community group. I view both of these things as planting seeds that will pay off on the long run. My goal with them also isn't to make sure that I have a date every weekend.

Any other suggestions? Just general ideas would be great. Any fun gay social outings that people can share?

As for online, I've tried gay.com, Manhunt, Craigslist, Connexion, and match.com. Manhunt seems to be just for sexual hookups. Gay.com seems to not know whether it is a dating or hookup site. Match.com is obviously more of a dating site and seems to get higher quality profiles, but there just aren't many guys on it and it neglects gay basics such as HIV status. I've actually had the best luck scanning craigslist just searching for the occasional normal post in the sea of cocks, balls, and asses. Connexion is kind of neat, but there just aren't that many guys on it and it doesn't seem very active.

I actually think that the market for relationship oriented gay dating is left largely ignored. I think that there is a good business opportunity that is untapped.

I've done the gay bar / club thing twice. Once was when I was dating a guy over the summer and I went with him and a group of friends. We went to R Place which is a young hipster place. I had fun but I was just there dancing with my friends and being stupid.

A couple of weeks ago I went with a group of gay friends and went to Purr, Neighbors, and the Cuff. Purr was mainly just a bar with surprisingly attractive guys sitting around and ignoring each other. Neighbors seemed like the cliche idea of what straight people think a gay dance club would be like. The Cuff seemed like a place where desperate, older, unattractive people go to get laid. I found that going clubbing is sort of boring when you are single, not much of a drinker, and not looking to go home with someone.

In the meantime, I've been mostly focusing on expanding my circle of gay friends. It's grown from one to six over the last year. I've had much more success with that than dating and it has proven more rewarding. I realized one potentially troubling thing is that I am more picky and have a higher bar for friends than I would for dating. I suppose that would probably mean that I'm too focused on appearance as far as dating goes. Ugh...

Christmas Fling

For various reasons, I decided to stay in town for Christmas this year. I've always gone home to visit my family or spent it with a girlfriend. This was going to be my first Christmas actually alone. I wasn't too worried since I have a good group of friends, but this year, it seemed fashionable for everyone to take long vacations over the holiday so as it got close to Christmas things seemed pretty lonely.

I noticed that the online M4M dating was a buzz for the holiday since everyone seemed to be looking for a warm body to cozy up with. I joined the fray and posted an ad. I got a bunch of responses, but none of them were appealing except one from a guy who while cute an thoughtful was just twenty-four years old (and eight year gap). I showed his profile to a friend and he asked when I was going out with him. I told him I was about to hit the delete key and my friend convinced me that I should at least go on a date with the kid. I couldn't come up with any valid reasons not to other than that it just seemed like too big of a gap for me so I responded.

We emailed a little while and ended up going out the next night. We me at a Starbucks after he got off work. Online dating is kind of a crap shoot and his pictures weren' super clear, but he seemed cute in them. He was pleasantly cuter in person. He was pretty shy and was a bit taller than average with short dark hair and pretty blue eyes. I'm normally the shy one but this guy was worse. This made me relax and focus on being friendly to draw him out. He seemed intimidated and nervous, but I felt like he liked me. We were there about fifteen minutes when the starbucks people came and said that they were closing.

One we were on the street, it was freezing and nothing else was open on that road so I got bold and asked if he wanted to come home with me to watch a movie. He had walked so we got in my car and made the twenty-minute drive to a video store by my house, rented a movie, and then went back to my place. I made a little snack and then we went to my TV room to watch the movie. I was getting a little nervous. I haven't done this thing a whole lot and it's kind of exciting not knowing what is going on. I've been on dates with guys where we did just sit and watch a movie. My 24yo date also had moved to Seattle recently from a small town and commented that he doesn't date much and is turned of by the sleazy gay scene so I wasn't expecting anything more than maybe a makeout session.

I had had a friend staying with me recently and the sofa bed in my TV room was still in bed state. We laid on the mattress and started watching the movie. I decided to be bold and cuddled up next to him. He didn't resist, but he didn't reall respond much. Then I brushed my arm against his. We continued like this for about ten minutes before I slightly rolled towards him and he wrapped his arms around me as we kissed.

Things got crazy as we rolled around making out. Hands went everywhere and I reached around to feel his shockingly tight 24yo ass. He moaned, "you're so hot," which would have seemed cliche coming from someone my age but was cute coming from him. Shirts were the first to go and I admired his slightly hairy body. I was prety amazed because he doesn't really work out, but he had a pretty decent body. The up side to being twenty-four...

Pants came off and we dry humped a little before heading to my bed. I picked him up and carried him cave man style (the advantages of being a gym rat) to my room. I tossed him on the bed and stripped his underwear off and attacked him. I got on top of him and kissed him and slid down to his largish cock. It was the second biggest I have encountered and I gagged a little trying to be all slick and do the deep throat thing.

He was super verbal and kept randomly moaning "fuck, fuck, fuck." After dating a really silent, awkward guy for a while, this was a pleasant change. I played with his ass and he got excited so I reached for some lubricant and worked a finger into him. His ass relaxed pretty easily to let my finger slide in and I worked the inside of his butt while continuing to suck him. I did a sniff test and decided against rimming him even though I wanted to :)

He was really getting into my fingering him and I decided I wanted to lay on him and grind my cock against his ass for a while and then try fucking him. I rolled him onto his belly and slid on top of him with my arms holding his down. I slid my cock between his cheeks a couple of times and then the head caught onto the rim of his hole. I had fucked one other guy before and it was way harder to enter him than this so I was surprised when the head of my cock slid into his ass. I was totally in lust and was kind of sex crazed. He started moaning and to my shock he opened his ass and lifted it up at me and then I matched him by sliding my condom less cock all the way in to the hilt. I knew I was doing something really bad. If I had been in his shoes, I would totally have pulled the plug and put a condom on the guy. As a circumsized top who knows that I'm HIV- negative, I just started thrusting. Eventually, I rolled him on his back and put his ankles around my ears as I reentered him. He started stroking himself and shot all over himself. I picked up the pace and absolutely exploded inside of him. I could feel my come hit the wall of his ass and then slam back into me. It was crazy. He moaned as I came. It was the hottest sex I have ever had, but I felt super guilty. I know that my more aggressive personality and physically imposing build probaly intimidated him.

We talked about it after and I asked him about condom usage and his sexual history. He's had very little sexual experience and not much anal sex. He's always been safe and we were both in a little bit of shock about what happened.

I spent my Chrismas Eve, Christmas, New Year's Eve and a lot of the holiday season hanging out with him. He's a good guy. We dated for about a month. He had a pretty bad breakup before me and was already battling depression so we stopped dating but are working on a friendship. I think that the age difference was a big problem since we definitely were at different levels and things got worse as time went by. Still, I don't regret it. I had a nice holiday season with a really nice guy. I'm convinced that I'm going to basically stick with a +- five year age window from my age going forward though.

Oh my god

I just noticed that I got linked to from The Great Cock Hunt. I've been reading his blog for years. I have been lazy and haven't updated this blog for a while. I kind of assumed that nobody was reading it so I didn't put much energy in. It got me excited to blog more. I was shocked when I logged in and had actual email from Alex. I almost felt star struck :)

My first boyfriend

As things were winding up with the intern, I posted a random "who wants to watch a movie and cuddle" ad on craigslist. As always, there were a bunch of responses, but a couple of them were actually worthwhile. One guy was pretty cute and I tentatively made plans with him that weekend. I got mail from another guy who sounded nice, but his pictures didn't come through. I only had one free day over the next week. I got mail from the nicer sounding guy with pictures, but he wasn't quite as attractive as the guy I already had plans with. Still, he sounded like the better guy. The other guy just wanted to feel a hard body against him whereas the second guy seemed to have more potential. Then I noticed the first guy's email address was a permutation of "slut seattle" so I decided to cancel and go with option number two.

I made plans to meet him at the dog park. Oddly enough, he told me he was going to borrow his dog from his ex. This should have been a red flag to me.

We exchanged nice mails throughout the week. Eventually they got flirty and then they got hyper flirty. Me, "I'm going to wrestle you and pin you to the ground." Him, "I'm okay with anything as long as you are on top of me." Eventually, he asked for my IM info (god I fucking hate instant messaging...). We started chatting a lot and things started getting more graphic. At one point I pressed him on whether he was a top or bottom, and he got uncomfortable and said that he just wanted to let things develop naturally. I warned him that I'm really inexperienced and shy on dates. He assured me that he was friendly and that things would be fine.

I got to the dog park early and spied vehicles pulling in. We had told each other which vehicles we drove and I saw a car that matched his description and saw a guy that vaguelly fit his description jump out. He was a year older than me, three inches shorter, and mediteranean. Honestly, I was a little dissapointed when I first saw him. He had kind of an average to mildly fit body with a flat ass and a tiny belly. He had a cute face and a great smile though. When we greated each other, he had a great voice. He was pretty masculine. He had a very friendly, warm demeanor and was quite flirty. I relaxed a little with him and enjoyed watching our dogs play. We lapped the park and then I asked if he wanted to grab lunch. He did but was puzzled about what to do with the dogs. It was a hot day.

I had him follow me to my house. I got the dogs some water and cooked lunch. We chatted and had a nice time. After lunch, I gave him a tour of my house. It ended in my bedroom and then I realized this was kind of awkward. I suggested we go sit down in the other room. We both sat down on the couch. I warned him before while IMing that I had never made a first move with anyone. He sat there and laughed and said, "you really aren't going to initiate anything so how about we just hold hands." That was all it took. I pounced on him and soon we were rolling around on the couch. Then I rolled him off the couch and pinned him to the ground. I rolled him over and laid on him kind of like we were in missionary position. There was a lump as hard as a tire iron in his shorts. We took off our shirts and rolled around some more and then he said he was getting rug burn. I apologized and led him to my bedroom.

I wasn't interested in having a fling so I had decided that our pants were staying on. I told him that was what I wanted and he said he was fine with that. We played around for hours and were having a great time. After a couple of hours, I knew that he had an event he needed to go to that night and that he needed to leave soon. I pulled his waist band back a couple of times and looked inside. Finally, I decided that I wanted to send him off with a blow job. I pulled his pants down and started sucking him. He asked if he could reciprocate and I told him no. I sucked him earnest for a long time. He said, "you want to see it work don't you?"

He warned me that no one had ever gotten him off through oral (he wacked off a lot and was kind of rough with himself). Eventually, I shed my pants and we stroked off together. I've always been a projectile shooter with high volume, but I was surprised when I came how intense it was and how many pulses there were. I sprayed everywhere and hit him in the ear. Then he came and shocked me. He completely soaked me from waist to head and got some on my face. It was actually quite a sweet and tender experience (after toweling off).

We met up the next day and took turns fucking each other. It was really sweet and seemed innocent. He hadn't dated much. He had been in a seven year relationship and he ended within the last year. He hadn't had sex for the last couple of years of his relationship. He made up for lost time with me. We exchanged loving emails and talked on the phone every day. We saw each other a couple of times per week.

We had some disagreements but the hardest things were probably that he was in a pretty rough place in life. He and his ex owned several properties together and were still in daily contact. They were also best friends. They fought all the time, and my boyfriend couldn't tell his ex that he was dating. My guy would invite me to things and tell me how thrilled he was that I was going to be his date and then cancel because he found out his ex might be there and felt like it would hurt him too much.

We dated for two months.

Eventually, his ex couldn't afford to live in the house they used to live in together by himself. It was really sad to both of them when the ex was moving out of their house to get it ready to sell. When things were already tense, their dog swallowed a ball and died. It was too much and his already emotionally fragile ex had a meltdown. I stayed up at night with my boyfriend crying about his ex and being afraid the guy would kill himself. I'd take him out to do something and he'd think of gifts to get his ex for Christmas that might bring him some happiness.

On a Friday night, we had talked about getting together and then he decided that he'd rather stay home. He called me the next day told me that he had gone over and smoked pot (and I am pretty hardcore anti-drug) with his ex. I had a hugely busy day and then accompanied my boyfriend to a commitment ceremony for his coworkers that he didn't even like. It was an awful experience. We hadn't had sex in over a week and I wanted to at least cuddle with him after it was over, but he said he just wanted to be by himself that night. I was feeling really unappreciated and abandoned.

The next day, he called me up and said that he really wanted to see me. He was just going to have brunch with his ex (for chrissake!) and then grab a couple of things from his old house and that we could get together in a couple of hours. I was all excited and cleaned up and made plans to have some fun with him. I got everything done and sat around waiting. I heard from him around 6pm that night. His ex's brother had come over and he had got caught up chatting with him and helping his ex. He acted really put out and tired. I told him we didn't need to get together and he acted relieved. I quickly ended the call.

After I got off the phone, a friend called and asked me if I wanted to run grab dinner. I said sure. Then he called back and said he wanted to come over. I told him after dinner. When I got back, he came over and I told him that I was pissed. He was furious that I wasn't being sensitive and supportive. We fought and fought with no resolution. Eventually, we kissed and sort of made up with no resolution. We made out and then went to get ready for bed. He stripped down to his underwear and I came over to him and started to slide his underwear off and he got mad at me and said that we could do that in the morning since he was tired. I was annoyed. I got up the next morning early and went to the kitchen to try and surprise him with breakfast. I started cooking and then he appeared in the kitchen fully dressed and said that he should get going. I couldn't handle it and told him I couldn't see him anymore. He seemed relieved. It sucked.

We exchanged emails after that and it seemed like we might reconcile, but then we started arguing through email. Email is such a bad form for communication, but it is especially bad for negative communication. The tone and subtlety are lost. Things escalated until each of us were saying very hurtful things to each other. He got mad and stopped speaking to me. It's been a couple of months and we have little to no contact anymore.

I honestly don't have any interest in dating him, but he was a special person to me and I hope to have some sort of friendship with him at some point. He really wasn't in a spot were he should be dating. He knows that now, but I was kind of collateral damage. Still, he was a nice guy and it was important to me to see that I could have a relationship with a guy. I do know that there are nice guys out there now. I just need to find some who don't have dysfunctional relationships with their exes :)

My first time as a bottom

After some experimentation, I've found that I'm more of a top than a bottom, but I don't mind bottoming. It just doesn't excite me as much as topping.

I remember playing around with sticking fingers and objects in my butt when I would take baths as a little kid. It wasn't sexual, but it felt nice and seemed fun. I didn't connect playing with my ass and masturbation until I was in my mid twenties. I remember reading about the prostate gland and jacking off in the shower while fingering myself (which stretched the limits of my flexibility). I shot so hard that I hit the ceiling of the shower.

A couple of years later, I had a kinky girlfriend who read all of the sex columns in the various magazines. The bend over boyfriend phenomenom was all the rage so we went to Toys in Babeland and got a strap on and harness. She was the first person who I had fucked in the ass, and it seemed fair to let her have her turn. I remember being on all fours and thinking what a mind fuck it was to have my six inch shorter, trim girlfriend lined up behind her muscle boy boyfriend getting ready to pop my cherry. I thought that she would do a little prep work like I had always done with her and go slow, but she just rammed it in. It hurt. A lot. We had to stop and then wait a little to try again. Once again she plowed in. It hurt but was tolerable. Then she started jack hammering me like a drunk frat boy (which would have been sexy if she was actually a drunk frat boy...). She started saying things like "take it bitch" and "you like your ass fucked." It was okay having a girl trying to be a porn star with a cold and not quite lubricated piece of silicon up your ass really is a mediocre experience.

Fast forward to this summer... I had my first time with a guy sexually and then I decided to be more careful since the experience didn't go well. I dated a little, but it was like before. Nobody stood out and I didn't go so far as even kissing anyone. I had a gay friend from out of town stay with me for a couple of weeks. He's a little older than me and happily partnered. He actually had no idea I was attracted to guys. I told him about my experiences and he gave me some advice. We hung out together a lot while he was in town and it was almost like having a boyfriend except the we didn't have sex.

After my friend left, I was pretty lonely. I have a lot of friends, but I had gotten used to having someone around to chat at night with and someone who I could share intimate thoughts with. I had had live in girlfriends pretty much since I was twenty-six so I hadn't lived by myself until this spring. I started up the dating pipeline again. Unimpressed with gay.com, I went back to craigslist. I posted an ad trying to specify that I wasn't looking for casual sex and that I was looking for a guy with boyfriend potential. I got the usual assortment of head less dick pictures.

Then I got a flirty mail from a twenty-four year old. He commented that it was nice to see an ad from someone who wasn't looking to just get down on his knees. He had a great body. He included a picture of his face but it wasn't too detailed and he was turned at an angle. His hair was longish (I'm a fan of short hair), but wasn't long enough to be a deal breaker. We started swapping mails. I asked if he'd like to meet on the waterfront to talk and grab some ice cream. He was excited to meet up.

When I met him on the waterfront a couple of days later, I was standing around looking for him. I saw a really good looking guy with super short hair in an abercrombie shirt. He looked like one of their models. The guy was looking around and then started waving to me. I was in shock. I never would have recognized him, but he looked much better in person.

He seemed a little flustered and I assumed that he was dissapointed when he saw me. I figured that even if he isn't interested, there is no harm in chatting with a cute boy in the sun. We walked back to his car and he grabbed some Indian takeout. We went and sat down at a table overlooking the water and chatted.

He was a PhD student in mathematics from Israel doing a summer internship. He was fun to talk to and I was having a good time. When he moved, I noticed his shirt sleeve pull up and looked at the definition in his arms. I liked the way his t-shirt hugged his lean, muscular body. I assumed once again that I was out of his league and nothing would happen. I think that was a good thing since I relaxed and just had fun chatting with him since I really had no agenda.

I asked if I could buy him some ice cream and he was excited. We went and got some Ben & Jerry's and enjoyed more sun. It was really nice. It was fun hearing about Israel and I was excited about making a friend from out of the country. After we talked a while, he made some comment that we should get going. I thought that he wanted to leave and then he asked if we could go back to my place. He seemed a little timid about it. I was kind of in shock but said yes. I had parked in a free parking quite a ways away so we got in his car and drove back to my car. He made a comment about how nice it was going to be to not sleep alone.

The drive back to my house seemed to take forever. When we got to my place, I realized that I had my neighbor's dog and that my neighbor would be coming by to pick him up. I kind of panicked and remembered I had the neighbor's key and told the guy that I needed to drop my neighbors dog off. I grabbed the dog (leaving my dog who was mauling my date) and ran over to my neighbors house. Fuck. I had grabbed the wrong key. I ran back to my house (still with the dog) and the boy looked confused. I grabbed all the keys in my drawyer and bolted over. I had so much adrenaline that I was shaking. I returned the dog and came back.

He was sitting on one side of the couch looking sexy. I sat on the other end (I have a long couch). We nervously talked for a little while. He considered himself bi but had very little experience with guys and was totally in the closet. Finally, he asked why I was sitting so far away. I said that he could move closer if he wanted. He smiled and crawled over. He was a little taller than me (6'1") but he was more of a swimmers build. I have a weight lifter / football player's build and picked him up so that he straddled my lap. We attacked each other and started kissing. I remember him smelling very masculine. We started groping and hands were everywhere. Finally we got up and walked to the bedroom.

We both stripped and I was in shock. He had a huge cock. It was really long, but it was incredibly wide and bulged in the middle like a snake that had swallowed a mouse. He was very proud to show it off and liked my reaction. We rolled around naked and he told me that he isn't into sucking guys. He also had never tried anal and that he hoped that we could try that at some point.

After playing for a while, I started sucking him. His crotch had more of a musky odor and he leaked precum like crazy. He was so big that it was a little hard to work with. He asked me to lick his balls and he really got off on that. I was sucking him and he grabbed my head and kind of pushed me down a little on him. He told me not to try to swallow it all and to wrap a hand around the base. I gagged a bit but got a little better with some practice. I looked up and he moaned, "suck my big dick" as his eyes rolled back in his head. We alternated making out, me sucking him, and him jacking me off for a while. I decided I wanted to try a little more.

I grabbed a condom and suited him up. It looked absurd. It was a normal condom and his poor cock looked like ten pounds of potatoes in a five pound bag. It looked really uncomfortable and left a couple of inches of shaft exposed. Still, it was all I had and I wanted to give it a try.

I got on all fours and lubed myself up. I tried to prep myself a bit with fingers. He got behind me and rammed himself in. I doubled over in pain and made him stop. It hurt like hell, but I was determined and asked him to try again. He said that maybe he should lay on his back and then I could lower myself and control it. We tried that and it worked pretty well. I worked my way up to it. It still hurt, but it was tolerable. After a while it went to nuetral and then started to feel good. He was super concerned about STDs and didn't want me to lower myself enough that my ass touched his unexposed shaft (given that both of us had essentially zero exposure, he was being a little over paranoid, but whatever).

I decided to try something different and climbed off and got on my back. He lifted my legs up and started to fuck me missionary. This felt really good. He completely pounded me and after a while he said he was getting close and asked where he should come. I was having a porn star moment and said in my mouth. He pulled out and peeled the condom off and made a comment that he was happy there was no shit on the condom (smooth...). I started sucking him but he wanted to do it himself so I licked his balls while he beat off. He got close and said that he was about to come. I took him into my mouth and he thrust deep and unloaded. Unlike my first experience, this guy had a strong, pungent taste.

After it was over, he was kind of paranoid and lectured me about swallowing (annoying since he had been thrilled in the moment...). He warned me about STDs and asked me if I had done that before. I told him once and he asked me about it. He seemd a little nervous and I felt like kind of a slut (but in a bad way). He was supposed to check in back home so he went in the other room and called his family. The whole thing felt surreal.

He cuddled with me while I jacked off. He told me that he wasn't into cum and he seem startled when I came and a little uneasy.

He asked to stay over and was a super cuddle bug. I went to pee and he stopped me before I came back to bed and asked me to flex for him. I felt really, really cheesy, but he seemed to get into it. He told me that he was really attracted to me when he first saw me and thought that I looked really dissapointed when I saw him (far from the truth...). From how I talked to him, he thought I wasn't interested in him but was trying to be polite and friendly. He told me how much he liked the pictures that I had sent him (not naked, but in a swimsuit). He was into the muscle thing.

We went to bed cuddled up together and I was happy.

I got up before him the next day and made belgian waffles with fruit. I brought them to bed and we ate. Then we started fooling around. I sucked him for a while and then he beat off and came on his belly. He commented that he never felt sexual in the morning so he was surprised.

We did yoga together and it was fun to do naughty yoga with a cute boy. After it was over, we messed around a little bit. Then he wiped up again with a towel. I said that we should shower, and he said he didn't need to and just asked if he could borrow a shirt from me. I gave him one and he headed off to work (WTF!). I was pretty happy.

We emailed the next day and he told me he was freaked out and needed some time to process that he had sex with a guy. I was pretty dissapointed. I sent him nice mail a couple of days later and got a terse response. I figured that I wouldn't see him again, but I kept getting really short, terse emails from him. We finally agreed to get together again. He asked me to cook him diner and if we could watch a movie.

He came over and I had cooked a really nice meal. I served the food and we sat the table and he got up and came over and hugged me. He liked the food and he commented about how awful things had been for him and then he commented about being so mean to me. He told me about his internship last year. He met a guy and they got together occasional and they would fool around. He knew the other guy was having sex with other men and he didn't care. He fell in love with him. When he returned to Israel in the fall, he was really heart broken. He told me that is was important that we didn't get too attached to each other.

After dinner, we kissed and rolled around a little in bed. Then he said that we shouldn't kiss anymore since we will get too close and get hurt. It was bizarre. We went to watch a video and he suggested that we watch some porn and beat off so that we could both be more relaxed. I was weirded out. I put some porn on the DVD player and we he started stroking himself and asked me to suck him. I did for a little bit and then crawled up to kiss him. He kissed me a little and then reiterated that we shouldn't kiss. I went to the other side of the couch and he asked me to lick his balls. I did for a second and then realized the absurdity of the whole thing and stopped. He was totally conflicted. He finally came. I cuddled up with him during the movie and he alternated between cuddling and being awkward. He told me that I'm a really nice guy and that I deserve someone nice. He told me that I'll have better luck if I play hard to get and don't make myself so available. He also said that I should work on my self confidence. It was weird to be lectured by a closeted 24yo who has no idea what he wants. He's clearly gay and just can't come to terms with it.

He asked to spend the night. I honestly wanted him to go but I said he could stay. We got in bed and cuddled a little. He laid on his belly and I laid on top of him and wedged my erection between his ass cheeks and started kissing his neck. He told me to stop and that we need to just be friends. I gave up and rolled to my side of the bed. I started to try to try to go to sleep and he acted hurt and asked why I wasn't cuddling with him. I've never been so frustrated. He went to sleep and then I went in the other room, beat off, and came back to bed.

I got up the next morning and dressed before he got up. When he got up, I was fully clothed and told him that I had cooked breakfast. We talked during breakfast, but it was obvious that I was annoyed. I was fully clothed and didn't touch him at all. He finished eating and said goodbye and left. We didn't hug, shake hands, or anything. I've never heard from him since. I hope he is doing well. I think he is in a rough position. It's kind of sad too since I really liked him. I've since learned to not get involved with guys with that much of an age gap (eight years), guys who aren't out, and guys who are pulling that bi-curious shit.

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...