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This is a true story, but before I get a bunch of safe sex lectures the events depicted took place in the fall of 1982. Back in those days 'safe sex' meant plugging your vibrator into a grounded outlet.
My college girlfriend, Paula, was a really kinky girl. Soon after we started dating she introduced me to her collection of toys and the thrill of anal penetration. She did such a good job that it became one of my favorite things to do. Paula had a bisexual male friend from back home going to the same school as us. We used to hang out together quit a bit. One night the three of us were doing some drinking and smoking some pot. Pot always got Paula horny and pretty soon she started snuggling up close to me. I was getting a little nervous because Ted was there, so I was telling her to wait till later. At that point she was nibbling my ear and whispered that she'd like to try a threesome with Ted if I was willing. I wasn't sure but being pretty buzzed I agreed on the condition that I didn't have to do anything I didn't want to. Paula suggested the idea to Ted and he, of course, said he was into it. We undressed each other and got on the bed. I love Paula's pussy, so I lay on my back and had Paula straddle my face. I was licking away at her while she was grinding her snatch into my face when I felt a mouth engulf my dick. Expecting it to be Paula I was surprised when it turned out to be Ted. He was actually a pretty good cock sucker, obviously experienced. I thought I would have been turned off by it, but with Paula's pussy in my face I was anything but turned off. After a while we switched positions and I started fucking Paula doggy style. Ted got underneath us and started to lick my dick as it went in and out of Paula. That was an awesome sensation. He started to take bigger swipes, and was soon licking my balls and all way back up to my asshole. We were all getting really turned on and I came pretty fast. After I came Ted took my cock in his mouth and gently licked the juices off. After that Paula started sucking on Ted's dick. She wanted me to join in but I just couldn't do it. It was really fun to watch her giving him head though. In his excited state Ted didn't last long either and he shot off in her mouth. We lay there talking about what we had done and smoked another joint. Paula started telling Ted that I liked it when she fucked me in the ass with her dildo. I was getting a little embarrassed with her telling Ted all of our intimate secrets. She came right out and suggested that Ted fuck me in the ass while she watched. I said I didn't know if that would be such a good idea. They both started trying to convince me, Ted saying he'd be gentle and Paula talking about how sexy it would be and how much I'd like it. With the kinky nature of the discussion I started to get aroused again, so I agreed on the condition that Paula would help and make sure that Ted was gentle, and that we could stop if I wanted to. I lay face down with a pillow underneath me as Ted and Paula got behind me. With my naked ass propped up in the air I felt very vulnerable. If I said I wasn't nervous I'd be lying. Paula had gotten out some lubricant, a small vibrator, and our dildo. When I saw our dildo next to Ted's dick I became a little more relaxed because they were equally thick and the dildo was longer. Since I had been enjoying the dildo for the past few months I knew that I would be able to take his cock and that it would feel good, but I was still nervous because what I was about to do was so naughty. After all, it's not every day that you get talked into letting a guy shove his big cock up your ass. Paula lubed up a finger and slid it into me. It felt great as always and my dick got instantly hard. I had her toss me her panties and I wrapped them around my cock so it would feel better that the pillowcase.
I felt a second finger enter me and looked back to see that it was Ted's.
Now they were both finger fucking my ass. It was great, they would stroke in unison and then alternately as I pushed my ass up to get them deeper. Paula knew from experience, and my thrusts, that I was ready for more. They pulled their fingers out and Paula lubed up the vibrator. She placed it at the entrance to my asshole and pushed. It slid in easily and the vibrations sent waves of sexual excitement rippling through me. Paula and Ted took turns fucking me with the vibrator for a couple of minutes to loosen me up and then pulled it out. I looked back and Paula was lubing the dildo while Ted was stroking his cock. I told her to skip the dildo so that I wouldn't be too loose for Ted's initial penetration. I could tell that Ted was really horny because his cock was hard as a rock as he rubbed the lubricant on it. Paula straddled my back facing back toward Ted. She reached her hands down and spread my cheeks as Ted placed his cock at the entrance to my well lubed hole. I was still a bit nervous but really excited thinking about what was about to happen. Ted began to push into me making very gentle thrusts. His cock was much warmer than the vibrator and I think that helped my ass relax and allow him in. Soon he had the head wedged in my rectum and it felt great. After giving me a minute to relax Ted was quickly able to get the rest of his cock into me, I could tell that he was all the way in when I felt his pubic hair against my ass cheeks. That was a new sensation and I thought it was really nice.
His cock felt really good in me and was making my cock hard as stone. Ted began to gently thrust in and out. Paula meanwhile was cooing about how horny she was getting watching Ted's cock slide in and out of my ass. Seeing that I was handling Ted's strokes quite well Paula got up and moved around so that my face was in her pussy. This was great, I was getting to do my two favorite things in life at the same time; eating pussy and getting butt fucked. With Paula off my back Ted was able to lie on me. With most of his weight on his elbows he was able to reach under me and play with my nipples. I loved it when Paula pinched my nipples while fucking me with the dildo, and it felt just as good with Ted's cock in me.
I was in ecstasy as Paula thrust her pussy in my face and Ted thrust his cock in my ass. He was alternating between long deep strokes and fast shallow ones, I was thrusting my ass back to meet every one. After Paula came a couple of times she had me get up on my hands and knees so that she could climb under and watch Ted's cock going in and out of me. This also let her take over on my nipples and afforded me a really good view of her pussy. I was glad that she had brought Ted off in her mouth earlier because he was able last a good long time, and I never wanted it to end. My ass was hot, wet, and open as I took thrust after thrust from his rigid member. From time to time Paula would start playing with my dick and I would have to make her stop because I didn't want to cum yet. Ted had been fucking my ass for about 30 minutes when finally, after a few particularly fast and deep strokes, he announced that he was about to cum.
Paula slid up so that my cock would go into her mouth. As Ted made his final thrusts I ground my ass hard against him trying to get him in as deep as possible. Paula, sensing my need, reached her hands back and spread my cheeks wide, allowing Ted to penetrate me as deeply as possible.
The sensation of his final inch sliding in was just too much. Ted dumped his load deep in my ass as I shot mine in Paula's mouth. We had so much fun and were so into it that we fooled around all weekend, between the two of them I must have taken it up my ass ten times by Monday morning. Paula, Ted and I were able to have sessions eight more times that semester before Ted, unfortunately, flunked out and had to go back home. To this day that Fall semester has been my only experience with another man.