Bisexual Man Takes Cock Up His Ass for the First Time

I have always been aroused by the thought of sex with a guy. I was 14 the first time I masturbated and my fantasy was giving another guy head. I was an athlete and my family was prominent in the area so I never acted on it, I guess out of fear. That's what got me here, almost 11 years later.

My relationship with Tom started out by accident and luck. Still fearing being "found out" I would jump on the internet's gay chat rooms and chat, when I was alone. One night, I was chatting in the room when an private message box popped up and the guy introduced himself as Tom and that we were from the same city. I was a little startled, but excited at the same time. Usually the chat rooms I was in were country wide and I never spoke with someone that close. We started chatting on a regular basis on the internet.

I had a girlfriend at the time and actually meeting this guy was out of the question. After about two weeks of chatting, he said he understood my position and gave me his phone number just in case I ever wanted to talk. I memorized the number in about 5 seconds, but figured I'd never call it.

About a week later, I was driving home from work and I found myself thinking about him. I felt like I was on autopilot as I dialed his number into the cell phone. One ring, then two, then a "hello" came from the other side of the phone. His voice was easy, and I could tell he was gay by the sound of it. I answered back, "Hello? Tom?".

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Tom said "yes? May I help you?" At this point, I was literally shaking. "Tom, this is John...We've been chatting on the internet".

Tom's voice lit up, "John, how are you?"

That started a conversation that lasted an hour and a half (in the car). The funny thing was that when I dialed his number, I was only 5 minutes from my house. I drove by my house and seen my roommate was home, so I pulled out and drove around talking with Tom for the next hour and some minutes and finally pulled back into my drive. I told Tom that my roommate was home, but if I got a chance, I'd call him back.

Well as luck would have it, my roommate was walking out the door, he told me he'd be back in a few hours. I waited 10 minutes to make sure he wasn't going to pop back into the apartment and I dialed Tom's number again.

This time Tom answered in a flirting voice, "so you couldn't wait to call me back, could you".

Playing into the flirtatiousness, I replied, "no, I just kicked my roommate out so I could talk to you".

He started laughing and said, "so your all alone then? Well strip out of your clothes".

It was like I was under his power. I had dated many women and never done phone sex, but this call was different, I did everything he told me to and this conversation ended with a mess all over my stomach. I told Tom I would call him soon and I did.

Well this starts a week later. I pulled up to the house, nervous and a little shaken, but elated. I opened the door and got out. I thought to myself, "I could turn back, I probably should", but I decided no way, not now. I was closer than I ever was before and now it was going to be a reality. Three hours before, I was at the bar with a bunch of friends, if only they could see me now. We were talking to women and slamming beers with no one suspecting what I was about to do. At 2:30AM, I jumped in my car and I was quite horny. I picked up my cell phone and dialed Tom. I was drunk and it was easier to talk to him.

"Hello?" the voice was half asleep.

"Tom?" I said when I heard the phone pick up. I knew it was late and he was probably sleeping. I hoped he wasn't mad.

"John?" his voice woke up and he was happy to hear from me. I was elated.

"How are you tonight?", I asked, trying to just make conversation.

"I'm good, but I know you didn't call to see how I was doing. Why don't you come over right now and let me show you what a man feels like", was his reply.

I was shocked, not in a bad way, but that he knew exactly why I called. It's kinda funny looking back on it. We talked the whole time I was driving over there which brings me back to getting out of the car.

I walked up to his door, and he was there waiting for me. He was wearing a bath robe and was standing at the door. I hadn't seen a picture of him, but he was a good looking guy. I was pretty happy!

He invited me downstairs and turned on the TV. I sat across from him and he asked me if there was anything I wanted to do. I said TV was fine, I was nervous.

Well Tom got up, put in a video and pressed play. Gay porn came on across the screen and I instantly felt my groin bulging. Tom came back and this time sat on the far side of the couch, but next to me. He could tell I was into it, but at the same time, knew I was conflicted in my feelings about this whole ordeal. He inched a little closer, then closer and 5 minutes later, he was sitting next to me. He put his hand onto my leg and asked if it was alright if he could do that.

I replied in a quiet voice, "yes".

We watched the video for about 5 more minutes and Tom started touching his cock with his hand outside of his robe. I looked over and watched as he did this, and again, he asked me if it was alright if he did that. And again, I replied yes.

As soon as I replied yes this time, his hand shifted up to my belt and unfastened it. He then proceeded to unbutton my jeans and he stood up. He pulled my jeans and boxers off at the same time to reveal my excitement. I was as hard as a rock and he just grinned at me and asked if I was comfortable. I nervously laughed and said yes, but he could feel me shaking. He went down to his knees and put his mouth on my cock and almost instantly, I felt like I was going to cum. No woman had ever done that to me before.

I quickly told him to stop. He stopped and looked a little disappointed. I think he thought I wanted to stop totally, but when I knelt down on my knees so we were belly to belly, he knew differently. It was like something took control of me. I opened his bathrobe and it reveled a thick cock that was no less than 9 inches long. I put my hands around his waist and he sat down on the couch with me between his legs still on the floor. I touched his cock and I could feel mine pulse while I did it. I didn't know what to do.

He then put me back on the floor, seeing I was eager to learn, but totally inexperienced and put me on all fours. He then said, "just stay there a minute." To which I was fully compliant.

He came back in a matter of seconds with a condom and some KY. He put the condom on and rubbed the KY around his magnificent cock. He asked me if I wanted "it" and of course I told him yes. It was something I had told him many times on the internet and phone.

Just as he inserted his cock, which amazingly took only one or two tries to get in (I may not have ever been with a guy before, but having the feelings I did, I experimented prior to this). It was amazing. I felt it go in and I loved it. He went slow and it felt almost indescribable. Just then I thought of my girlfriend, not that I felt bad about cheating or anything, but that I wanted her to see me taking it in the ass. It aroused me more. He rolled over and put me on top of him and I rode his cock. I loved every second of it. He tried to touch my cock a few times but I warned him I would cum if he did. He then told me to relax and when he was going to cum, he could grab my cock and we could cum together.

A few minutes into it, I could tell he was going to cum. He reached over for my cock and grabbed it and started stroking it hard. I knew he was about to cum so I put my hips into it like a girl does and he stroked harder releasing his load. I instantaneously released mine with a shot that hit his chin. He continued to stroke me until I was empty. When we were finished, he licked what cum he could off his chin and we went and cleaned up.

This was the first time I did this and we are still friends three years later.

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