Copyright 2003 by NiftyMan
The day I first felt a cock in my ass didn't start out like that was where I was going to go. I was single, I had broken up with my girl friend six months before.
It hadn't been serious. We were together for a while because we liked to hang out, but we never talked about the future, so we knew that we liked the sex but that was about all. After a year, she took a job offer in California and was gone. Done.
So I was single again and was dating, but nothing was really working for me. I met some women but no one I wanted to have sex with.
I day I first felt a cock in my ass started in Washington, DC, where I was living. I went down to Miami for business. I caught an early flight down to Miami for some meetings and was supposed to catch the last flight out that night. It would be a long day, but it would work for me. I didn't have anyone to come home to.
A combination of the meeting running late and traffic problems caused me to miss my flight back. I went to the hotel phones and started calling for a room. I made a reservation at a hotel and they sent a van to get me. But when we got to the hotel, they had to move somebody and they didn't have a room for me. The desk clerk told me that the motel across the street had a place. He had called to hold it.
The motel was not a chain motel and took in overflow from the chains. I went in and there was a good looking young woman at the desk. It was 11 pm and I was worn out. She had heard my story before and told me to hit the pool to relax before turning in. It was a warm night and I thought it would be a good idea. I asked her to get me a couple of beers from the bar and I would be right down. She said her boyfriend was out there getting ready to close it down but it would be okay.
I put on my trunks and went down to the pool. The lighting was way down. He was wearing a speedo and he had just gotten out of the pool. He said that the pool was normally closed but that I could relax for a while. I hadn't planned on trying to pick up the clerk, Barb, and her making a point about her boyfriend, Jerry, put paid on that. He was pretty hunky. I'm not a slouch, but he had a great body.
I got into the pool and it felt great. Barb came out with the beers and after taking a few laps, I drifted over and took a long pull on one. Jerry said that we would have to be quiet, so we talked with low voices. He came and sat on the side of the pool and it looked like he had quite a cock in that speedo. We talked for a little bit and then Barb came out. She said that she had closed up the office. They were the night crew.
Jerry got back in the water and we were talking about guy stuff and then Barb took off her blouse and skirt.
She was wearing a one piece suit under and slipped into the water. She and Jerry were close and touching each other. We talked about my misfortune. She asked me if I wanted a back rub.
She got in back of me and started rubbing my back. She held onto my waist with one hand and rubbed with the other. Sometimes if felt like she had rubbed her pubic arch against the back of my leg. She said that the one who was best at back massage was Jerry. She asked him if he wanted to give me a quick massage.
I guess there was a moment where I really didn't know what was going on, but after a bit, I began to get clued in. He said okay, and she said that it would be better if I was laying down. She said that the sauna was still warm.
We went into the sauna and Barb took a cushion from a chaise lounge along. I stretched out on it and there was just room for him at my feet and her at my head. He started describing for her what he was doing. She said that she was trying to learn massage. Jerry had taken a lot of classes and she was learning from him.
She asked if I was supposed to have my trunks on and he said not during a massage and she asked if I would like to take them off and put a towel over my mid section. I said okay because it was reasonable. He started working on my back and it felt good. He knew what he was doing. He worked on my back and legs. She asked if she could try. They changed positions and she started on me.
Her touch was lighter and she moved up my legs to my ass. I started to get a boner. A couple of beers in a short time and eased my inhibitions. At some point I knew that this was no ordinary massage. She spread my legs and was talking about muscles and such, but her fingers were more interested in my anus and prostate.
She started rubbing up and down the crack of my ass lightly, down to my scrotum, talking about relieving tension. I got hard. Jerry was working lightly on my shoulders. When her fingers dallied over my anus, I knew that they were seducing me. I thought for a couple of milliseconds and wiggled my ass to let her know I liked it. I think I also groaned. She pushed a little with her oiled fingers and I groaned with pleasure then.
I looked up and saw Jerry's cock sticking up out of the top of his speedos. Since he was on his knees on either side of my head, his cock was about four inches from my face. I had never seen a cock up close like that. He straightened fully and I put my arms around him and put that thing in my mouth. Damn! I was sucking a cock!
I had often wondered what it was like to suck a cock whenever I got a blow job, but now I had one in my mouth. It was sort of rubbery, but it was pretty cool. Jerry was leaking a little pre-cum and I tasted cum for the first time. I started working on his knob and he pulled his speedos all the way down so his balls were free. Barb started really playing with my ass and I moved with her hand.
We broke and all started laughing from the tension. Barb rolled me onto my side and started going down on me, playing with my balls, prostate and ass. Jerry stood up, pulled off his trunks and knelt down again. I got that cock in my mouth as quick as I could. I could not believe I was sucking a guy off! He took my head in his hands and started rocking back and forth. I was rocking my hips at Barb and Jerry came in my mouth. That pushed me over the edge and I shot into Barb's mouth. I was fucking giddy.
Jerry pulled me up and started kissing me, licking the cum off my face where it had not made it into my mouth. I was kissing a guy and I liked it. I was shivering with excitement. We collapsed into a happy pile and Barb said "What about me? You guys got off!".
We got our clothes back on and went up to my room. Barb raided the bar for a few beers and we were a little shy with each other. I asked if I could watch the two of them together. Barb started kissing Jerry and he pulled her suit down. She had a killer bod. I started going down on Jerry again and he was getting hard. I went down on her and she had a great pussy. She had him lay on his back and straddled him facing away. She had Jerry spread his legs a little and told me to do both of them. I had this great view of his cock, damn it was a good cock, sliding in and out of her pussy. I went down on her and gave his cock a good licking at the same time. The smell was fantastic. I had his smell and her smell at the same time. She came quickly but he took a little longer. She came a bunch of times before he came and I lapped up his cum as is drained out of her pussy.
They collapsed on the bed and I lay next to them. Barb had her hand on my ass and I spread my legs a little. She took that as an invitation to slip a finger up my crack and find my anus. I had decided that if Jerry wanted to fuck me, I wanted him to. I always wondered what it felt like to get fucked in the ass but I worried about the people that I would meed while trying to accomplish it. Here I was with two great people who were loving and I thought I could trust. But I didn't feel I could just come right out and say that I had always wanted to try getting fucked in the ass, wanna take care of that for me?
Barb took my hint and pushed on my anus. I wiggled my butt a little and she started playing more with it. It was a little irritating, and I think she knew that.
She got up and got the massage oil from her bag and came back to bed. Soon I felt her slippery fingers playing with my ass and it felt good. I think she liked ass play also because she knew how to do it.
She slipped a finger tip in and out and I thought I had gone to heaven. If he didn't want to do me, maybe she would do me with a dildo. "Jerry", she said, "I think I found someone for you to fuck". I turned to look at her and she was looking right into my eyes from about six inches away. She slid her finger in deeper and started a little action with her finger. My hips went with it and I was squirming on the bed pretty good.
Jerry looked past her at me and I must have had a goofy grin on my face because that is the way I felt. He had a sort of smart ass look on his face "Want some cock?" and he laughed. We all laughed, that nervous laugh that happens when taboos are broken.
He went over to my side of the bed so that I was in the middle. Barb and I both rolled over and he put his hand on my cock. He was propped up on one elbow. "Want me to fuck you?" I didn't answer right away and he said "I don't want to do anything that you are uncomfortable with." I had this impulse to run, but I tried to talk and my throat was dry. It took a couple of tries to get out "I want you to fuck me. Please fuck me."
Barb turned my face to her and started kissing me and Jerry started playing with my cock, working back to my anus. I spread my legs so he could have lots of room to play. Barb hooked one leg over my left and Jerry had one over my right and I was really spread out. I felt like I was being devoured. Jerry put some massage oil on his hand and started playing with my ass in a big way. The touch of his fingers on my ass was amazing. I wanted them inside of me, I wanted him inside of me.
I giggled a little bit when I thought of what I must look like, spread out that way and then he put a finger in me and the giggle turned into a groan of pleasure. I was really impatient and wanted him to fuck me now! Barb was kissing me and that was pretty good too. He had two fingers in me and was taking it slow and I came to appreciate that later. I was tight around his fingers and he used lots of oil.
He started talking to me about how he was going to like fucking me, that I would like it. I was really turned on by that. He said that he wanted me on all fours and I was there. Barb positioned her self so I could go down on her and I did with relish.
This was back in '81 and there was no talk of safe sex then. People just got it on and that was what I was going to do. Jerry was in back of me and I knew that he was about to enter me. I felt the head of his dick on my anus and he told me to push back on him. I pushed back and nothing happened. I pushed back harder and the head of that magnificent cock popped in. It hurt more than I anticipated and I just about called the whole thing off, but I knew that it would go away. Jerry pulled out and then pushed in again. He held my hips with his hands and I pushed back against him a little and eased up. Together we worked on him until I felt his pubic hair against my ass.
I knew that he was in then and he pushed a little more. I almost passed out from the sensation of him pulling his cock all the way out and then sliding it all the way back in. It wasn't pain, just intense sensation. I stopped eating Barb for a moment and she said that it would get better. "Now give this guy a good fuck, honey" she said in a teasing tone. I was ready at that point and he started fucking me.
He really knew how to fuck and I learned from him. Nice slow steady strokes that made me whimper and almost beg to be fucked hard. Then he would grind his pubic hair into my ass and pull out again. I started pushing back on him, rocking on the bed. Barb soon had an orgasm, bucking against my mouth.
She pulled away from me and I concentrated on getting fucked. I really liked the feeling of being held by his hands and feeling him power into my ass. After Barb recovered, she crawled under me and took my cock in her mouth.
I wasn't really hard then but I got hard fast. Rocking back and forth between that cock in my ass and just the head of my cock in her mouth had me on the edge. I must have squeezed my ass because Jerry let out a groan. I felt Barb reach between my legs and Jerry said "Oh, baby, don't do that"
She had a finger on his anus and was playing with him.
She soon set the pace and he was flexing his legs and banging hard into me. I couldn't believe the sensation as he fucked my ass. There was this great slap of his thighs against mine and I knew I was going to cum. He started breathing in short breaths (I was already there) and then I was cuming and I think it pushed him over the edge. He made these mighty stabs into me with his cock as he came in me. I really liked that. I had been fucked.
Barb slid out from under me and I collapsed on the bed with Jerry on top of me, still in my ass. He pushed into me and gave me another squirt and I squeezed my ass on him and he yelped. I turned and there was Barb's beautiful cunt right in front of me and leaned over and slicked it with my tongue. She flinched and we all laughed.
Jerry started to get off me and pushed in one more time and I pushed back but then he popped out. I thought about all that had happened that day and there was not one thing that I would change. I looked at Jerry and said "That was great" I told Barb to slide between us and I spooned her as she was kissing on Jerry.
After a bit, they got up and said that they needed to go, so we had some hugs goodby and they left. I had a hard time sleeping after that. I wanted some more sex. But I dropped off to sleep.
I saw them one more time in Miami but they were going off to join a commune and we didn't hook up, just talked about it. I found other hook ups in Miami for a while before I decided to get married and have kids.
I liked sex with men, I still do, but I'm married and that is more important to me. My wife and I have some friends with an open marriage, but we seem to be doing okay right now. When the kids are out of the house, we may be more expiremental. When my wife and I first got together, we were pretty wild, so I know she has it in her.