My First Time with a Guy : Part I

After years of fantasizing about being with another man, I finally got the courage up to go through with fulfilling my fantasy. It all started with a simple posting on a gay sex hook-up site. I simply posted my stats as being "a white, 24 5"11 175lb CD curious guy looking for an older CD admirer who is strictly a top to break me in as his bottom". I got several replies based on the pictures I posted but only one reply really fit the criteria I was looking for and his name was John (named changed to protect his identity). John was a 43 yo white guy who had been divorced for about a year.

He said he had only been with one guy before and that he was only interested in being a top and that he wasn't even interested in sucking my cock, which is exactly what I had fantasized of as playing the "women's role" in the gay sex. He also mentioned, that he enjoyed anal with his wife so it wouldn't be something totally new to him, this made me happy to know that he would know more about what he was doing since obviously I had never had anal before.

After getting John's reply, we chatted online for a few weeks and exchanged some pictures, mainly pictures of me as he asked me to model all of my lingerie outfits for him so he could choose which one he'd have me wear when we finally got together. We also used these photos to cyber. Finally after a few weeks John had eased my nerves enough to finally go through with it, so now we just had to set a time to actually meet up which was tough since I live with 2 roommates who know nothing about my situation.

Though it was tough to find a time when they weren't around we finally caught a break one week as I learned on Wednesday that both of my roommates were going out of town for the weekend. So we decided He would come over after work on Friday. The only request he had was that I answer the door dressed in my lingerie and that he'd bring the lube and condoms.

I was so anxious and nervous Wednesday and Thursday that I could barely sleep and keep myself from masturbating while fantasizing about Friday and how everything would go. Finally Friday came, and just before John arrived I took a shower and cleaned made sure I was clean shaven so I would look good in my outfit for him. Next I got ready putting on my lingerie and stockings. No more did I do this and John called telling me "I am on my way, I should be there in about 10 mins." Now my heart was really racing, I just kept thinking, "this is really going to happen." About 10 mins later I heard a knock on the door.

I walked to the door, opened it, and there stood John. My stomach dropped in fear of the situation becoming so real. I invited John in and after the door closed, he reached in to kiss me. I always was against the idea of kissing another guy even though I wanted to do everything else, but in the moment I leaned in subconsciously and french kissed him, while he put his hands on my ass, giving a little squeeze. Next he asked me, "Let me take a look at you in that sexy outfit." So I gave turned and gave him a look at my ass that he was just squeezing and asked "do you like what you see?"

He replied "mmmm....wow does your ass look great in that outfit, the pictures gave this outfit no justice, and I cannot wait to get that thong down around your ankles. We are going to have a lot of fun with that ass. " I just smiled and told him I think we should take this to the bedroom. He nodded his head in approval so I took his hand and we walked to the bedroom with him staring at my ass the whole way. I was so happy that he was so impressed with the way I looked.

When we got to the bedroom John took off his shoes and socks and took as seat on the edge of the bed and told me it had been a long day at work. He suggested that I should give him a lap dance so he could play with my ass a little bit and I could relieve some of my nervousness. After a few minutes, John had gotten quite the erection and he said, "if you are ready I think it's time that you suck your first cock." So I slid down off of him and got onto my knees with him standing in front of me. As I began to unbuckle his belt and slide his pants off, he removed his shirt, now the only thing between me and my first cock was his pair of boxer briefs which were barely holding back his bulging erection.

Next, I calmly pulled down his boxers as if I had sucked many dicks before and out sprang his erection. His cock was even bigger looking that in the pictures. I then grabbed his cock and quickly leaned in licked up the back of his shaft up towards his mushroom head. John just moaned "mmm it's been such a long time, and that feels so good."

As I reached the tip of his cock I started to take it in my mouth and began bobbing my head. All I could think about at first was all of the articles that I had read online about how to give a good blowjob. But after a few minutes it just began to feel natural and I started to really get into it. I started to taste the pre-cum that oozing into my mouth. Every few mins I would pull it out of my mouth and lick his shaft and swirl around his head. John was enjoying receiving as I was giving the blowjob but then he abruptly pulled his cock out of my mouth, leaving me begging for more.

John told me, "You can suck me again later, but now I want to get that ass ready for my cock." So, he told me "get on your stomach on the bed and prop your ass up in the air." Next he grabbed the lube and slid my thong to the side and started licking in and around my hole. After a minute or two he popped the lube open and started messaging my rim with it and slowly trying to stick his finger in me. Once again I found myself to be really nervous, so I was a tensed up and he told me, " relax and just think about how good it felt to use your dildo once you got loosened up." Once I relaxed John was able to get 2 and then 3 fingers in me fairly easily.

Then he asked me to take my thong off and leave the rest of my outfit on. I knew what was coming next. After I took the thong off I reassumed my position and prepared myself to be fucked doggy style. No more once did I got back into position, John had his cock pressing against my asshole. He began to rub me with his cock and just teasing me. Finally I found myself begging John, "please put your cock in me, I can't stand the teasing anymore." and he replied "tell me how bad you want it".

I said "I want you to fuck me soooooo bad, make me your little cockslut John, show me how a real man fucks." So he started to insert his cock into me and at first it hurt because it was stretching me so much. Finally, he got his full girth into me after a minute or two. Slowly he began to slide his cock in and out of my ass and at first it didn't really feel very good, but I reminded myself to relax my ass muscles as that always felt better with my dildo.

As John began to pick up the pace I relaxed more and more and really started enjoying being fucked. John started talking really dirty to me and I found it to be a real turn on. He kept saying "you like that big cock in your ass, don't you, you little slut" All I could do was moan and reply "uhh huh, or oh yeah."

Though I was really enjoying being fucked doggy, I told him I wanted to ride him. So he pulled out and laid down on the bed. Without his cock in me I felt really empty, so I quickly changed positions and got on top of him and took his cock back into my ass. After riding him for a few minutes he told me he wanted to see the reaction on my face when he cummed. So we changed positions again and this time I was on my back. He got into position onto of me and once again pressed his cock again my ass and inserted it. This time we began to kiss as he was fucking me but after a few minutes he stopped and told me he was about to cum.

So he stopped kissing and he started fucking me really hard and then he blew his load into the condom, pulled out and collapsed on the bed next to me. I was all sweaty and sticky as I had blew my load all over my chest and got a little on John as well just before he blew his load. After about 15 mins or so John asked for a towel so he could shower. I gave him a towel and he told me "I can't believe that was your first time, you were a natural and if you ever had any doubt, that you were a bottom, then you can rest assured now because you loved taking that cock way too much to be anything else." Then he, turned back again and said, "Just so you know, I will gladly fuck you anytime." Then he went off to take a shower as I lay there, thinking to myself about what a little cockwhore I had just been and but how good it felt. I was so happy that I had lived out my curiosity.

(To Be Continued)