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.