Anal Play

By Anonymous

The story is autobiographical, except the name was changed.

I met Judy when I was a grad assistant at a big northern school. She was a returning student in her late twenties, and I thought she spent a lot of time around after class; I guessed she felt a little more comfortable with the grad students than the other undergrads, since we were closer to her age. Halfway through the semester, I realized we had developed an attraction for each other; it was just a question of waiting until the end of the semester so I could give in to what I was I feeling and ask her out, without it seeming so unethical. She was a short brunette, moderately pretty, but with a lot of personality, and fun to be around.

Late in the semester, I was teaching a review session at night, and she made a point of dropping by my office for help and staying until everyone else had left. I forget what we talked about; something related to the material, but there was a lot of sexual tension between the lines. She had left a couple buttons on her blouse undone, and I could see some cleavage; my weak spot. She had really nice breasts. I offered to walk her to car in the parking deck. I was saying good night to her; she looked up at me, grabbed the back of my neck, and pulled me to her, kissing me on the mouth. So much for my academic integrity. I melted immediately. Well, “melted” isn’t really the right word. “Sprang to life” is a little more descriptive.

Within five minutes she was down on her knees in the parking deck, sucking on my cock. It was one of those sort of blow-jobs where there’s not even a question of asking if I could come in her mouth; she sucked the whole time as if she was desperate for my come, which I gave her willingly, in big hot spurts. She said she was having her period; I’m not sure if she wanted to hold back a bit, or if she really was. We said goodnight, but not before I’d asked her out. So much for good intentions.

We went out for an Indian dinner and a movie the next week. She was fondling my cock though my pants in the restaurant; I had to pay the check all bent over. I took her home (I’m not even sure we bothered to close the door to her apartment) and practically sprinted for the bedroom. We were naked in a flash. “Let me return the favor from Thursday” I said, and plunged my tongue into her steaming pussy. She moaned with pleasure. I licked, sucked and rubbed my face into her pussy until she came once. I kept going. I pushed her knees up, and slipped my tongue up the crack of her ass, passing it briefly over her asshole.

Those of you who enjoy this little quirk know how it is; you’re really dying to do it, but that first time in bed, you want to slowly feel out the other person to see if they like it, or they’re weirded-out by it. The effect on Judy was electric; she moaned even louder than when she came, and immediately twisted around and put her head between my legs. Where I had gently licked, she sucked and pushed. We lay in a sixty nine position, probing each other’s assholes with our tongues. That night led to much more fucking and sucking; I think I came three times, once in her pussy, once in her mouth, and once, all over her tits, rubbing the come into her big brown nipples with the head of my cock.

I’ve never had a lover who so matched me in anal desires. The next date we went a bit further. Almost before we had our clothes off we had our tongues on each other’s assholes. “I bet I can get my tongue in further than you.” I said.

“You’re so RUDE!” she responded and chuckled, but she immediately spread my cheeks with her fingers and pushed her tongue an inch or two up my ass. I fingered her clitoris while we continued.

One thing I really like about analingus is that when you’re being licked, your cock fits so conveniently between her tits. We continued like this until she came in long shuddering pants, and I spurted all over her tits. We cuddled for a long time, until I got hard again. I massaged her until I was solidly hard, and then I started licking her asshole. We both had the same thing in mind. I put my cock against her asshole and pushed a bit, but it didn’t quite work. She reached into a bedside drawer and produced a jar of Vaseline. I covered her asshole with it, my cock with it, and slowly worked it in. Unlike in Usenet stories, getting it up the back door requires a bit of patience and a lot of lubrication. Judy was incredibly rewarding; her asshole was always tight at first, but after some gentle probing she was riding my cock, thrusting back at me, as if I’d been fucking her pussy.

We kept dating that spring, and every week, we’d add something to it. We loved all the fucking and sucking, and sometimes we’d set the video camera up on a tripod and play in front of it. Judy loved it; it really brought out her ‘slutty side’ as she called it. We’d each only had one previous lover who enjoyed anal sex, so neither of us were very experienced. Every pleasure was something new. She introduced me to the bottom position, lubricating my asshole and finger-fucking me, starting with her tongue and building up to a finger, then two, then three, then four fingers. Nothing was really out of bounds. We were talking over our fantasies in bed; I confessed to her I wanted her in a threesome with another woman. She told me she wanted me in a threesome with another man. We agreed if we could find other people interested, we’d indulge each other, although we were both a little lukewarm about joining in with a person of our own sex.

We started a little fantasizing, asking the other exactly what we’d want to do in a threesome. I was a little surprised when she told me that she’d give anything to watch me being fucked in the ass by the other man, although the way she enjoyed it when I let her finger-fuck me should have been a big hint. That week, I thought I’d indulge her as best I could. I didn’t have any bi friends of either sex, but I went to a sleazy adult bookstore I knew had toys, screwed up my nerve, and bought a big strap-on dildo. I took it home and gift-wrapped it.

The next night, I showed up at her door with the present and told me I’d tell her when she could unwrap it. She understood immediately it was something sexual, and immediately pulled me inside, dropped to her knees, and started sucking my cock. We went into the bedroom, and began playing. I told her to “Lick my Asshole” (she liked talking dirty) and she really cleaned me out until I was ready to burst. I told her to unwrap the present. She did, and shrieked with pleasure. I got on the bed, kneeling, with my ass up in the air. She took it out, strapped it on, slathered my ass and the dildo with Vaseline, and slowly slipped it in. It hurt a lot at first. As I got used to it, it became incredibly pleasurable; I can’t believe how much I enjoyed it, especially because I’d never had any gay fantasies, let alone experiences. I have to recommend it for the straight man!

Judy just loved fucking me. The dildo vibrated, and she usually came quickly while buttfucking me. I was right on the edge of coming as soon as the big rubber cock was inside me. We’d include this almost every week. Usually, as Judy was coming, she’d grab my cock, pump it a few times, and I’d come with her. Often, we’d fuck face to face, so I’d spurt on her face and tits. We’d never waste come, so that would mean I’d lick it off and share it with her.

A few weeks later, I went back to the bookstore and bought a double-ended dildo. We used to share it; a great toy. Sometimes we’d both take an end in the ass, sometimes she’d take the end in her pussy. Particularly when we were playing with the video camera, one of us would suck on an end. God, sometimes in the afternoon when I was trying to study I’d pop the tape in the VCR and jack off to her to her deep-throating the big dildo with the far end shoved up my ass. My favorite video, though, was one we took where her bedroom opened out onto the patio. There was a big sliding glass door, and we sat the camera up out on the patio, almost on the ground pointing upwards. She sat on the ground facing the camera, and I backed down onto her ‘cock’.

There’s a incredible scene of her fucking me up the ass; she reaches around and jacks me off, shot after shot of come splashing onto the door right in front of the camera. When I’m done, she crawls around me, still wearing the big dildo, and licks all the come off the window while looking into the camera. I love watching myself shoot off on camera.

Once, we fucked right after we’d finished a dinner, right on the table; I made her lick my come up off the dining room table. We relaxed in each others arms for a few minutes. As we were panting on the table, she said “Let me finish off the dishes.” (She was incredibly fastidious in keeping her apartment neat.)

I asked her to hurry. I said “Do you know what the word ‘marinate’ means?”

She said “yes,” looking puzzled.

I said “Good,” and took a grape out of the fruit salad, and shoved it up her pussy. She gave me a look that would melt brass and disappeared into the kitchen. I went into her bedroom and stretched out on the bed. I heard frantic cleaning up noises from the kitchen, and she came flying into the bed room, and landed twat-first on my face. I licked and sucked her pussy, eventually sucking the grape out. I don’t know what got into me, but I then pushed the grape up her ass, and sucked it out. Her reaction was just indescribable. Eventually I went into the kitchen, got the whole bunch, and had her bend over the bed, and shoved them alternatingly into her pussy and her asshole, sucking them out. (I didn’t count; I don’t know whether I got them all back.) That night we had the most incredible sex; I fucked her in the pussy, then she strapped on and fucked me in the ass; then she sucked me off, then I ate her pussy and ass, then she fucked me again, then I fucked her in the ass just before we dropped off to sleep.

The next weekend, I was determined to take it a step further; I was awash with anticipation for the *kinkiest thing I’d ever done. Yay ! I went out shopping that Friday for all I’d need. I brought her to my place, as my house-mate was away for the weekend. We fucked on the couch, and then I brought into bathroom. I ran a nice tub of water over her, kissing her and massaging her neck. I opened the bathroom cabinet and pulled out the enema bag. Her eyes got all big. “I have some special plans for you, and I want you to be all clean for them.”

“Okay”, she said, “but you too.” I nodded. I got the big jar of Vaseline that had become a staple in our sex life, reached into the water, and lubricated her asshole. I filled the bag with warm water, added a tiny squirt of baby shampoo, and screwed the nozzle in. I inserted it a couple inches up her ass. She moaned. I slowly filled her with the entire quart of water. I backed into the tub. She licked my asshole for awhile (I enjoyed a freshly washed asshole; she seemed to enjoy it more if it was a bit dirty) and filled me up with water. We took turns on the toilet noisily blowing it all out, then refilled each other with fresh water. This time, we turns on the edge of the tub going down on each other, coming. We expelled it into the toilet again.

I took her by the hand, and led her into the dining room for dinner. I’d set the table, complete with lit candles. On the table was a bizarre dinner, at least if you didn’t know what it was for. There was a bowl of fruit salad, mostly grapes, strawberries, and peaches. There was a bowl of olives. A squeeze bottle full of vegetable oil. An assortment of candy bars. A can of whipped cream. A bottle of warm champagne. Some carrots. A cucumber. Her eyes lit up immediately. She pulled herself right up onto the table. I lubricated her ass with the oil, squirting a lot up there. We started out with a fruit salad, filling each other full. After we started having trouble getting more in, we fucked it in; me ramming it in with my cock, and her with the strap-on. If you like anal sex and analingus, you can’t imagine how nice this is. I came hard in her ass while packing the grapes in, and shoved some more strawberries into her now gaping asshole. As I pushed the strawberries in, I licked up the mixture of come and grape juice trickling out her asshole and shared some with her in a scalding kiss. She filled me with more grapes. We got into a sixty nine position right there on the table, and started licking and sucking. It was apparent only the stuff near the anus could be sucked out. We started fucking with her on top facing away, and just as she came, she squirted out a corn- hole-ucopia of fruit all over me. We hunted down the fruit that had the most come on it and shared it.

I pulled out before I came. I sat on her chest, jacking myself off. She locked her tongue into my ass, and just as I sprayed come all over her titties, I squeezed hard, filling her mouth with fruit. She came as it happened. I can’t tell you all the combinations we went through that night. Maybe you at home, playing with yourself as you read this, can think up some new ones. We really tried to stretch ourselves. We killed ourselves laughing as we set up my video camera, to videotape each other shitting candy bars into each other mouths. We gave each other a warm champagne enema. This is great for two reasons; first, you get really drunk, and second, you fart uncontrollably when all that carbon dioxide starts getting released, which seems really funny when you’re drunk.

She took me by the hand and we stumbled back to the bathroom, giggling all the way. She thrust me down in the bathtub, squatted over me, and blasted champagne all over me, laughing hysterically. As the champagne dwindled off, a jet of pee started and hit me on the chest. As soon as she realized what was happening, she stopped and got terribly embarrassed. I told her it was fine, and that it felt good. “Really?” she asked. “Show me!”

I pushed her to her knees, stood, and started pissing on her tits. I sprayed all over her, and as I finished, she stuck out her tongue, and I finished in her mouth. She loved it!

At the end of the evening, we’d finished all the food except for the olives (they didn’t go with anything else) and some of the candy bars (we were getting sick of sugar; besides, who wants to be called ‘fudge-packer’ when you really ARE one). I’d come five times in the evening, and I can’t tell you how many times Judy came.

I moved away not too long after that, but I still cherish the memory of all the things we did. I think it was one of those relationships that was partially driven by sexual exploration, and after that night, the relationship was a little anti-climatic, if you’ll forgive the pun. There wasn’t much else to really do after that. She didn’t like the idea of bondage; we played golden showers a bit more, once drinking all the other could produce, though neither of us liked the taste much; we’d usually only swallow it when we’d been drinking a lot and it was watery. We never did find anybody we wanted to have a threesome with us, which I still regret, but it was still a great relationship.