Well, it finally happened. At 27 years old and after years of having the urge to mess around with another guy, I finally worked up the courage to see it through last weekend. My first time wasn't your traditional first time. I was looking for a something specific. I am an athletic and muscular… in short, I am a jock. Very straight acting with a girlfriend, and you would never guess I had this side to me. When it comes to guys, I am not attracted to other guys like me. I am attracted to skinny nerds who are shy and timid. Now, you're probably thinking this is because I'm a jock and I want to manhandle and have my way with a guy smaller than me, but that assumption would be wrong. In fact it's quite the opposite. I had a strong desire to be fucked, manhandled and humiliated by a scrawny guy. I had fucked myself with toys many times but obviously never experienced a real cock. On to the story. After many hours on Grindr, I wasn't finding what I was looking for so I reluctantly created an ad on Craiglist. I said I was looking for a" skinny nerd type" who may have gotten picked on in high school and wanted to take it out on a jock. I posted a picture of my athletic body and muscular bubble butt. I obviously received a TON of responses from interested guys, but only two that really fit what I was looking for. They both sent me some pics and I emailed back and forth a bit with both of them and eventually we chatted on the phone. They both seemed like normal guys but one really interested me more than the other. When I talked to him on the phone he was very quiet and reserved. He was a pre-med student at the local university an said he tutored other students in his classes. He also said he was on a "math team" in high school. Bingo. This was the guy. He said he lived by himself so I could come over there. Obviously it's pretty sketchy to meet someone from craigslist at their place, but this guy really didn't seem threatening or dangerous so I agreed. Like I said, I've never been with a guy before so I quickly cleaned out my asshole as best as I could, grabbed some condoms and flew out the door. I didn't know if he would actually fuck me but I wanted to be prepared. He lived in a typical university apartment complex with a bunch of drunk kids running around. I knocked on the door and the cutest, nerdy looking guy I've ever seen answered the door. He was short and looked to be only about 5'4'' or so. He had on glasses, which is a major weakness for me. I could see how this kid may have gotten picked on quite a bit by guys like me. We sat down on his couch had a some beers and chatted for about 15 minutes to warm up to each other. He had a PS4 so we played Halo for a bit (he was good). I could tell he was getting fidgety and my cock was hard the moment I walked in the door, so I scooted over to him on the couch and started to kiss his neck. Remember, this was my first time so I was pretty clueless about what I was doing, I just knew I had to do something because he was to shy to get it started. I never had the desire to actually kiss a guy, but we began passionately kissing and all those thoughts went out the door. He stopped kissing me and quietly said, "suck my cock." I didn't say a word. I just dropped to my knees in front of him, unzipped his pants and released his cock. Now, I've seen a lot of dicks in gym showers throughout my life but this was the biggest one I had ever seen. It was really disproportionate with the rest of his body and had to have been about 9 inches long. I muttered "fuck…" under my breath and he let out a giggle. I took the dive and put him in my mouth, tasting the sweet pre-cum oozing out. Being my first time sucking a dick, I gagged more than I thought was possible. He didn't seem to care and began to forcefully shove his dick down my throat. I was vomiting on his dick but he kept it going. I thought, "is this a dream?" He was really taking his aggression out on me. He slipped his dick out of my mouth and walked to the middle of his living room. He stripped off his clothes and beckoned me over. I told him I was having second thoughts because he was so big and I had never taken anything that big inside of me He just said "get over here and lay on your back" in his tiny high pitched voice. I obliged. I took off my clothes and laid on the floor in front of him. I told him I had condoms but he said he was clean and didn't want to use those. I believed him (and the condoms wouldn't have fit him anyways). He lubed up his dick and my asshole and lifted my legs in the air. I thought with the aggression he was exhibiting he was going to ram it in as hard as he could so I braced myself. Instead he eased inside of me until my hole was relaxed and ready to take it all. After a few minutes he began to work it faster and faster until he was pounding me real good. I was already loving what was happening to me so wasn't expecting much more, but all of a sudden I saw some rage come over him and he started to slap my face and chest. I exclaimed "fuck yeah" and he told me "you're not supposed to enjoy this you asshole." He spit in my face and slapped me again. I was in heaven. He fucked me good for another 10 minutes or so before blowing his load inside of me. I had never felt that sensation before but now I think I'm addicted. He pulled out and laid beside me exhausted. I was jerking off this entire time and blew my load all over my stomach not long after he finished. He was suddenly back to his shy self and quickly put on his clothes and said, "thanks." I followed his lead and put on my clothes. He said, "thanks for coming over. We'll have to do it some other time." I just nodded and walked out the door a happy man. Pretty good for my first time.