My First and Only Time

My first and only time.

This happened more than 20 years ago when I was a young man. I had a best bud, Mike we'll call him, and he was the same age as me. We were always hanging out together and we had all kinds of things in common. We liked the same sports teams, kinds of cars, clubs, alcohol, and (I thought) the same kind of women. Tall, slim with big boobs, tight asses, and long flowing hair. At least that's what I thought, until that one time, after a night of drinking.

We went back to my apartment after we had left the club. We were both very drunk and neither of us should have been driving but since my apartment was closest to the club, we got in my car, left his in the parking lot, and drove to my place. When we got there, I asked Mike to open the bottle of vodka that was sitting on the bar because I had to go take a wiz.

When I got back, Mike handed me my drink and we sat down on the couch. I asked him if he wanted to watch TV and he said sure. So I turned it on and some softcore porn was on. I looked at him, he looked at me and we could tell what the other was thinking. What the hell, why not. So we settled into our seats and just watched as the woman on TV acted like she was sucking the man's cock.

"Man, I wish we had met some girls at the club. I could really use a good blow job right now." I told Mike as the bulge in my pants begin to grow and stiffen. "I could use one of those too." He said back to me. Then I told him that I needed to jack off and he said go ahead and that he was thinking the same thing. So I undid my pants, whipped out my cock, took a swig of my drink, and then proceeded to beat my meat. I looked over at Mike and he was going to town on his own cock, but he wasn't looking at the TV.

Nonetheless, I continued to watch the TV and enjoy the feeling that my hand was giving my cock. Then Mike moved closer to me and asked a question that I never thought I would hear from him, "Do you need some help with that?"

I just looked at him, confused. I mean, he liked women right? So I asked him what he meant by help with that. The next thing I knew, he had moved my hand and was stroking my cock. To say I was shocked is an understatement. I jumped up and was like, "Man, what the hell?"

He looked embarrassed and began to apologize, "I'm sorry. I thought you wouldn't mind if I helped you out." I just looked at him. I didn't know if I should kick him out, beat his ass, and then kick him out or let him jack me off. I mean, it was 2:00 in the morning, it was just me and him in my apartment and I wasn't going to tell anybody, so why the hell not?

I sat back down and told him that if he told anybody, I would deny that this ever happened and that our friendship would be over. He agreed and I took another swig of my drink. Mike took a swig of his drink and then proceeded to stroke my cock, while he stroked his own.

I was really starting to get into someone else stroking my cock for me and I begin to really, really relax when I felt Mike's tongue on my cock. I looked down as Mike began to swallow my cock. Now I had agreed to him jacking me off but this was going too far...or was it.

As Mike begin to bob his head up and down on my cock, I began to realize that this was probably the best blow job that I had ever had and it didn't take long for him to deep-throat my cock. For the next 5 or 10 minutes, his tongue tricks brought me to sheer ecstasy. He was so good at sucking my cock that saliva was running down my ball sack into my ass crack.

The next thing I knew, he had slipped a finger in my asshole. At first, I jumped and was going to tell him to stop and that we were done, that is until he hit (what I would find out later was my prostate) a spot inside my ass that sent me over the top. I begin to fuck the shit out of his face and all he could do was hold on.

It didn't take long before I felt the need to release and I grabbed the back of his head and shoved my cock into his mouth and touched the back of his throat. He sucked down every bit of my jizz and I jizzed a lot. When I was finally finished, I let go of his head, he sat up and wiped his mouth. "Did you like that?" he asked. All I could do was nod my head and try to catch my breath. Then he stood up in front of me and said it was his turn. I was thinking, What the hell are you talking about, I am not sucking your cock. But then he assured me that he didn't want his cock sucked, he wanted his ass fucked.

I was like, no fucking way am I going to fuck you in the ass, but then to my surprise, my cock was hard again. Then my thoughts turned to, a man who just sucked your cock, you jizzed in his mouth, the least you could do is fuck his ass, so I agreed.

I said ok but just this one time. Mike smiled, took off his pants, and got on all fours in front of me. I got behind him on my knees, spread his ass cheeks, and lined the head of my cock up with his asshole. I gave one forceful push and my cock slid all the way in. Having my cock in an asshole was a new experience, not to mention, this was a man's ass, but it felt tighter than any pussy that I had ever been in.

I grabbed hold of his hips and began to fuck his ass like I was trying to impregnate him. He met my every thrust with his own and would squeeze my cock as if he was trying to milk it with his ass. I began to feel as if he was a woman and I was his man.

The more I stroked his ass, the better it began to feel until finally, I was ready to release my load. I tried to pull out but he urged me to cum in his ass. I must admit, the idea of leaving my seed in him wasn't too appealing until I realized that cleaning it up would be his problem. Not mine, so I grabbed on tight to his hips and slammed my cock into his ass one last time. I thought I had jizzed when he sucked my dick but I jizzed so much more into his ass that when I pulled out, my jizz squirted out of his ass and onto the floor.

I fell back, onto the floor and watched his ass pucker as my cock went limp. Mike turned around with his cock rock hard and said that he need some relief. I told him that there was no way that I was going to let him fuck me in the ass and he just laughed. "No silly, I just want you to watch me jerk off. That's all."

I figured, what the hell? After all, he did suck my cock and I fucked him in the ass. How bad could watching him jerk off be? I didn't know how wrong I was but since I had already told him that I would watch him, it was too late.

Mike was about 4 strokes in when he let out a slight moan. To my surprise, that turned me on and my cock was now standing at attention for the 3rd time that night. The next thing I know, I'm in between Mike's legs, with his cock in my mouth. Now I had never had a cock in my mouth, nor have I since but that night, it felt natural and I must admit, I kind of enjoyed it. Before Long, I moved my hips over Mike's head and he sucked my cock into his mouth again.

I don't know how long we were in that 69 position but I do know that was the first and only time that I have ever had cum in my mouth. Mike was grateful and he thanked me for everything repeatedly. Mike and I continued to hang out but we never discussed that night nor did we ever do it again.

It's been years since that night and not a day goes by that I don't think about it. I'm married now and I have wanted to tell her about that night but I haven't built up the nerve. I still keep in touch with Mike but we never discuss that night. Maybe one day, when we're hanging out again and are a little drunker than we should be, we will see how far we are willing to go. Maybe, I will let him fuck me in the ass.