I just found this site and thought I would share how I lost my man cherry to my friend Steve this past summer. Let me give you a little backround. I met Steve four years ago when I started a new job. We became friends. It was a year before I knew he was gay. I found out because I wanted to fix him up with my wife's cousin, so he had to tell me he was gay. I had not suspected, he did not talk about his personal life, or let on in any way. It did not bother me, we continued to be good friends at work.
On to this year. My wife wanted a divorce and we had to sell the house. She had moved out and stuck me with lots of bills. I had to sell the house.
I had talked about moving back in with my folks to save on living expenses for a few months so I could quickly pay bills down. When the house sold in May, Steve made me an offer. I could stay rent free in one of his extra bedrooms to save me from having to drive the hour to and from my parents everyday. I thought about it and accepted. He had a pool and it was going to be summer. We wrote an agreement it would not be more than three months before I would be out. He did not want a permanent roomie but wanted to help out.
I moved a few things in the first week of June. Everything was fine, just like being roommates. He was doing his best to keep me in good spirits because the divorce really had gotten me down. The second weekend I was there, Steve was going to be out of town all weekend. I would have the place to myself and looked forward to being alone, thinking, and enjoying the pool. As usual, he told me to make myself at home. Before leaving, he told me if I wanted to watch some porn, there was some downstairs in the basement entertainment center. He added, "Don't worry, there is some in there for you." That was the first reference he had made about being gay since I moved in.
I had gotten married at 18 and had only ever slept with my wife. Now at 26, I was single and would have to learn to date. I thought I would never get laid. After Steve left, I got curious about his comment about the porn. My wife and I on occasion rented porn and I loved it. I was horny and decided to check out the porn and have a good jackoff session. So, I made my trip to the basement to check out the porn. I opened the drawer and found a fairly good size collection. I recognized some of the titles as classic straight porn. Then I read some more titles and reviewed the boxes.
I found a group of bisexual videos and as expected, gay videos. I consider myself sheltered grouping up and while I was married. Now I was alone with all kinds of porn and found myself checking out the guys on the boxes of the bi and gay videos. I decided to pop in one of the bi videos and turned on the TV. I watched as the image on the screen was a guy sucking off another guy while fucking a girl. I moved back into a chair and dropped my shorts, naked from the waist down. I watched on the screen as they all shifted and soon one guys was fucking the other with he eat the chick out. I had found my hard cock and was strokin. Halfway through the next sceen, I was shooting my cum into the paper towel I had brought for the occasion. As my dick got soft, I was fast forwarding from scene to scene to see as many images as I could. I put the tape away and went back upstairs to watch tv until bed. I went to bed thinking about the porn and imagining Steve watching the porn and jackin off to it. So I headed to the basement naked and another paper towel in hand. I picked a gay video this time. I watched the story unfold about a guy having his first gay experience and then hunting down more men. I slow stroked watching the scenes, often bringing myself close to cumming then backing off and saving it. After about a half an hour, I couldn't hold back any longer and let loose, this time shooting a huge load of cum onto my chest and stomach. I went to bed and slept great.
The next day was Saturday and I had planned to lounge around the pool. I slept in and I headed to the pool. By mid-afternoon, I was horny again so again to the basement. This time I pulled out a tape with no box or label. It was with the porn, so figured it was a copy of some type of porn. The image came on the screen, it was three guys on a bed. Then I realized one of them was Steve and it was his bed. He was lying back getting blown by some guy who was getting fucked. Almost immediately, the guy doing the fucking started cumming. After that, he pulled out of the guys ass and Steve said it was his turn. I watched him put on a condom as the guy moved on to his back and Steve moved and quickly put his cock into the guys ass and started fucking him. I think this is when I knew I wanted Steve to fuck my ass. I laid on the floor on my back and played with my ass as I watched Steve ass pumpin the guys ass. Soon Steve came and so did I. There were a total of three different sessions on Steve's home fuck tape. I watched Steve do everything... sucking cock, getting blown, fucking and getting fucked. I wanted to see what it was all about. I jacked off one more time before bed watching Steve fuck.
Steve was to get home Sunday evening. I spent the day by the pool. I did a lot of skinny dipping. The water felt great on my balls and cock, which was hard most of the time. I found the jets stimulating on my ass as I let them stimulate my hole. I was trying to figure out how to approach the subject of Steve fucking me.
I was in the living room watch TV when Steve got home about 7:30. I had a couple of beers by the time he arrived and he grabbed one and sat down with me. He asked how my weekend was and I said it was great and relaxing. He asked if I had made myself at home and I said yes, and I had even checked out his porn collection. He asked if some of his old stuff met my needs. I said, "Yes, but some of your new stuff was great too."
He looked surprised and said, "Really, you saw some stuff that got you off?"
Now was the time, so I said, "Yes, and the one of you was really hot, I think I would like you to do that stuff to me."
"How much stuff?", he asked.
I told him, "I want to see what it was like to have a cock in your ass, I want you to fuck me."
"Gladly, I'm horny as hell", he said as he stood up and headed to his bedroom. He emerged still in his boxer briefs, carrying some condoms and a bottle of lube. He set those down and came over to me. "Lets see how serious you are first, I want my cock in your mouth first." I looked at his crotch and saw partial wood in his briefs. He pushed them down and out came his cock. I nervously reached up and took it in my hand. I felt it getting harder as I began to feel it and stroke it. I moved forward and took it in my mouth. I did the best I could for my first time, but not taking a lot of him in my mouth. After about a minute, Steve stopped me, pulled out, and said, "You will get better, now lets see what you have."
I stood up and took off my tshirt and shorts and was naked. "Nice", he said as he dropped to his knees and quickly took my already hard cock in his mouth. It was an excellent blowjob from the start and why not, it had been forever. He started playing with my ass and starting to finger my asshole.
By the time he worked two fingers in, I was about to cum and he obviously knew it because he stopped and said, "not yet buddy". He ordered me on my back and he took the lube and put in on my hole. He told me to play with his cock while he got me ready and I did. He worked three fingers into me and said I was ready. He told me it would hurt at first, but then I would get used to it. He put the condom on his cock, added some lube to the tip and moved into position. I watched him as I felt the tip of his cock push it way into my loose hole. I hurt at first as he held his position until I got used to his presence. Then he moved in a little further. Soon he as short fucking me and moving in inch by inch. The pain turned to acceptance, and then to pleasure as he had soon buried his seven inches into me. I was fully hard again as he fucked me. I could tell he was enjoying himself and that made it more exciting. I reached to stroke my cock, but he said no, he would take care of it when he was done. He started slamming my ass hard now as he said he was about to cum. He took a few last long hard strokes as he buried it deep and started shooting his cum into the condom in my ass.
I was so hot for having given another guy pleasure, I needed to cum bad. He pulled out of my ass and immediately took my cock in his mouth. He was stroking and sucking me hard and fast, knowing I would cum quickly. I gave the announcement, "I'm gonna cum", like I had always given my wife, but he did not move, and sucked me even harder. I went over the edge and started cumming. Steve kept him mouth on my cock and took every drop of me into his mouth and swallowed it.
After he got the last drop out, he looked up and me and smiled. "I fantasized about this, but never dreamed you would ever". I told him I surprised myself, explaining I had never done any experimenting at all life, and the more I saw his videos, the more curious I got.
I spent the rest of the summer at Steve's. Lounging by the pool, paying my bills down, and either getting blown or fucking almost every night. I have since moved into my own apartment and started dating and having sex with women again. I am having a great time and I still drop by Steve's when the dating scene is not working out or when I am particularly horny.