TEEN ANAL SEX

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A Freshman's First Anal
Copyright 2001
Original story by your webmaster.


When I was in college I met this girl who was going to a community college about 30 miles from where I was. She came over to a dorm party at my school and I met her there. She was hanging with her girlfriends, one of whom was after my roommate, so we ended up just naturally sort of hanging out together. We drank some beers and I said " Hey do you want to smoke some weed...", and she said sure, so we went to my room and smoked some bongs. We was sitting together on the bed, and she put her hand on my leg, and somehow we started kissing, and then just went crazy like kissing each other, her rubbing my head and back and then my butt, and I started rubbing her butt, then her tits, then under her shirt.

She had one of those real thin bras on, with the snappy thing in the front, and it came off real easy, and her shirt was up and Jesus did she have a nice set of tits, big and firm with pointy conical nipples. I started sucking on those nips and she was groaning and moaning when suddenly the door opened. It was my asshole roommate with that girl who was after him. The light from the open door shined on the two of us, this girl with me sucking her tits. She screamed a little, and jumped behind the bed. I said " Hey Motherfucker knock next time why dontcha, Jesus did you grow up in a fucking barn...", and he says, "No but it looks like I was coming into a fucking barn huh?". Well, the other girl runs into the room and grabs her friend, and they run out giggling and then laughing like coyotes running down the dorm room hall back to the party.

What the fuck? My roommate and I did some bongs and we laughed a bit ourselves. Then we went back to the party. This girl, whose name I discovered was Debbie, wouldn't come back to my room with me but she said "Give me a call", and she writes her phone number on my hand.

So, a few days later I call her, and we spent the next two weeks talking on the phone for like 3 hours a night. (It turned out later I got a phone bill for like 300 fucking dollars. But it was worth it, as you will hear...) Jesus, did this girl have a dirty mind. She loved to talk about sex. But, she says, she's a virgin, and she doesn't ever want to get pregnant. Still, she asked me if I did it before, and when I said yes, she wanted to hear all about it. We talked and talked. She was 18 years old and a freshman in DUS, and I was 20 and a sophomore. She was a brunette with long thick hair, down to mid shoulder, very feminine, with big brown eyes, a bit of a pouty mouth, and like I said before, really damned nice tits. After a lot of phone time she said why don't you come see me? My roommate is going home to her parents for the weekend so why don't you come visit me in my dorm room?

I hitchhiked the thirty miles to her dorm with a couple of joints and a pint of tequila in my backpack. I called her when I got into her town, she seemed real glad and excited to hear from me. I bought some orange juice (for the tequila) and pizza and coke and she met me on the street corner and took me back to her room.

She was afraid to smoke the grass in her dorm room, but she was thrilled to see that I had some booze, so we made tequila screwdrivers and started to talk. Well, we talked for an hour, and then I realized she was sending me the signals, and I reached out and took her hand. We rubbed hands for a while and then started to go crazy again.

We were kissing so hard it hurt my mouth, and then we got into one of the best make out sessions I've ever had. Her shirt came off, then her bra, and while I was sucking her nipples I unzipped her pants and started rubbing her mound. Man did she like that, she was lifting her hips and pressing against my hand, and then she started to pull down her own pants. I helped her and soon her pants were down around her ankles, and I started to really stroke her pussy through her panties. She was wearing these little white cotton things, simple but obviously expensive with a lingerie look, and the crotch was dark with her juices. Her legs were spread wide and her eyes were closed. I decided to go for it and slipped my hand down her stomach and under her panties, reaching deep. Her pussy was hot and soaking and slippery, and not too furry, she was trimmed nice and neat. It seemed to only take a second to find the mouth of her vagina, and to start to finger fuck her. She was wiggling and moaning and she kicked her pants completely off and lifted her legs up so I could really pump my two fingers into her swollen wet slit.

She had pulled my shirt off, but when I started to pull my pants off she said "Oh no, I don't want to get pregnant...". "Don't worry", I said, "we don't have to fuck, but maybe we can do other things?". She said, "Like what?". And I said "well, you can touch it and you can suck on it." And she said, "Okay", and giggled, and then started to help me take off my pants. As I'm pulling them over my feet she grabs my cock with two hands, and then she wraps one around my cock, and she smiles at me and starts jerking me off. "Like that, right", she says, and I forget about my pants. "Ohhh, YEAH, just like that... Uh, where'd you learn to do that?" She giggles and said, " Me and Kathy practiced with a banana." Kathy was the name of her friend, the one who wanted to catch my roommate. "What else did you practice?", I asked, and she giggled some more and then she said, "Well,  this.", and she bends down and takes nearly my whole cock into her mouth and starts giving me one of the better blowjobs I've had. She sucks me silently for a minute, not moving her head much, but moving her tongue a lot on my cock. Then she lifts her head and says "I've never tasted a cock before. It was a little strong at first, but I think I like it. Did you like it?". And I says "JESUS FUCKING CHRIST oh yes I fucking liked it, do it some more.", And she giggles again (I would eventually get tired of all the fucking giggling, but it seemed real cute that night.), and gets back to sucking me.  She sucked me for the next ten minutes, asking me what to do. I said bob your head, and fuck me with your mouth, and she did it, really eager to please. Before too long she added the thing with her tongue, slurping around the bottom of my cock, and that was enough to start pushing me to an orgasm that I wasn't able to stop. "Ah Gawd baby I'm going to cum from that..." And she stopped for a second and said "Do you want to?", and I said "Jesus YES", and she said nothing but started sucking me again. I knew she wanted me to come in her mouth, and I stopped fighting it and laid my head back and let her suck the cum out of me. I think I was yelling "Fuck, FUCK!". Her mouth was soft and wet and pulsing and I squirted everything I had into it. My balls just kept pumping and pumping. She started to cough softly on my dick, and I could feel her gulping, but she never let my cock go with her mouth. Jesus, women like that are few and far between.

I'm not sure what happened next, I was so blasted, but she ended up in my arms and we were cuddling and kissing. She had cum on her chin. She said, " Do me some more...", so I fingered her and then got down and began licking her pussy. Unfortunately, I wasn't too experienced with that at the time, I think I just got her really excited but I couldn't make her come. Hell, I hardly knew the female orgasm existed at that time. She started to moan, "Oh, I wish you could fuck me.", and when I started to climb between her legs (Okay, so I'm an asshole. You'd have done it too if you were in my place, with her pink pussy right in my face.), she screamed, "NO, I don't want to get pregnant!". I was a little hurt at this, and started to get mad. "Well, I have a rubber, how about that?", and she said "Rubbers break.". We actually sort've had a little tiff for a minute or two there. I don't know why, like I said, okay, I'm an asshole, alright, but for some reason I says to her, "Well, let me fuck you in the ass, then, you can't get pregnant that way.".

(Of course, I knew that cum could drip into the pussy, I'm not stupid, but I said it anyway.)

She was quiet for a minute, and then maybe two. I thought she was gonna throw me out. But then she says, "Okay, if you want to, you can do that.".

You could have knocked me over with a feather. I hadn't really meant that we should actually have anal sex, but here this girl, this virginal freshman, was offering me her anal virginity, even before she gave up her pussy virginity. Holy Shit!

"What should I do?", she asked, and even though I should have said forget it, I wasn't serious, you can get pregnant that way, I found myself saying "You should get on your hands and knees in front of me on the bed.".

Now, I had never had anal sex before, and I was trying frantically to remember what I had read about it in the skin magazines and good old Cosmo. I thought to myself, "I should use a lube.", but I didn't have one, so I said "Hold still", and I pressed the dry head of my cock into the crack of her ass. Naturally, it wouldn't go in. I pressed a bit until she said ouch. Then I said, "Do you have any vaseline?".

She said "What do you want that for?", and, lucky me, all that reading of penthouse stories came in handy, because somehow I had my shit together enough to say "Well, ordinarily I would use the juice from your pussy, but I don't want to risk you getting pregnant.". She seemed to think that this was sweet. Anyway, she stretched out on the bed in front of me to reach a drawer, and came back up with a little jar of vaseline. I took it and said "get back into position.", and bless her horny little heart she did. She looked back over her shoulder at me, and wiggled her butt a little and then giggled, and said, " I can't believe I'm doing this.".

I couldn't believe it either, but it was really happening. I remembered reading someone who said 'loosen her up with your finger first', so I decided to try that. I dug a fingerfull of vaseline out of the jar, used my left hand to spread her ass cheeks a little, and started to finger her asshole. The vaseline was a little sloppy, and I almost dropped a big chunk, but somehow I managed to keep it together and push my fingertip into the crinkled brown hole of her anus.

She gasped a bit as I entered, then started to breathe heavily as I pushed the fingertip in and out. "How's that?", I asked, and she said, in a husky voice, "I like it so far.". So I began to finger her more deeply. Every once in a while I tried to push more vaseline into her butt. I was glad I started with a lot cuz it seemed to disappear into her asshole. (Later I realized that using so much lube was a big part of how well this anal sex session turned out. ) It wasn't to long before I was finger fucking her asshole, stroking my finger in and out about once a second. She was moaning and groaning at least as hard as when I was fingering her pussy.

I got another fingerfull of vaseline and rubbed it on my cock. My hand was sticky with grease, and I looked around and saw my underwear on the bed. I don't need those anymore, I thought, and used them to wipe off my hands. Now I was ready for my first anal!

I scootched up behind her again, and using my left hand again to spread her creamy ass cheeks. Her anus was glistening with grease, real pretty, a crinkly brown star about an inch  across. Her anus mouth was open a little bit from my fingering, a little swollen and pink. What a sight. I pressed my cock tip against her asshole, and started to push in.

At first nothing seemed to happen, then it was as if the guardian of her asshole relented, and she relaxed and let me in. "Oh!", she half-shouted, half-whispered. I pushed some more and she said "Wait, wait, that's too much!." So I waited, with my cock head about an inch into her butt. " That hurts a little", she said, and I said "That's okay, it's like losing your virginity, right, so it's supposed to hurt a little.".  She says, "Could you pull it out and put it in again? maybe it would hurt less?", and I says okay, and slowly pull it out, and then I put on some more lube, and I say you ready, and she nods, and I put my cock onto her asshole, and push it in again, only a bit more firmly and quickly this time. I go deeper, but stop and hold still before she says anything. "Gawd, you so beautiful!", I say to her, and I am rubbing her back and ass and legs, but just holding still with my cock in her ass.

After a few minutes of this I tried an experimental stroking, slow, about a half inch thrust into her ass. She groans, but doesn't complain, so I keep it up, but slow. Holy Jesus motherfucking god was she tight. I was still only about two inches into her, but her ass gripped my cock like it was one big round slippery muscle, which I guess is exactly what it was. I was glad I had already come, or I'm sure I would have popped instantly at the feel of her most private opening and entry wrapped so extremely tightly around my cock head.

The pleasure of it was too much and I started to fuck her harder. At first she tried to take it but as I pushed half my cock up her ass, then two thirds, she started to squeak and cry out a little bit. For some reason I realized I should slow down, and I did, actually, I stopped, and stroked her back and sholders again, and then I pulled her erect so that we were both on our knees, with her back pressed against my chest, with my cock still embedded in her ass. I was kissing her and rubbing her nice plump tits. Then I reached down between her legs and started rubbing her pussy.

This makes her go back to moaning and groaning, especially when I was finger fucking her. Then she started to push her butt against me. I kissed her and finger-probed her pussy, which seemed to be getting wetter and softer. She started gasping and wiggling her ass harder and harder. Then, all of a sudden, it was as if somewhere deep in her relaxed and she just pushed her ass all the way up onto my cock. "Ahhhhhhggghh", she groans out loud. "Oh my god! I can't believe it, I can't believe it, I got it in!".

I took an experimental stroke into her and she just yelled out loud, as if she was surprised. "Hold it, hold still, hold still....", she says. Does it hurt?, I asked but she shook her head, and said not really, it's just so intense, I have to get used to it. So I go back to kissing her and finger fucking her pussy, which she seems to approve of very much.

As I start shoving two fingers harder and harder into her pussy, her asshole is sort of naturally pushing back onto my cock. Something was good about that position because she starts moaning, and I mean serious moaning, in time with her asshole sliding on and then off my cock. I had one arm wrapped around her and that hand grabbing ahold of her hefty tit. I start to pinch her nipple between my fingers, sort've rolling it between fingers and thumb. Our faces are pressed together and our lips are rubbing and touching, we are not really kissing but the wetness of our mouths is still in contact somehow. She was moaning and groaning and mewing into my mouth, and when I pulled my fingers out of her pussy and started rubbing the front of her mound, where I knew her clitoris was supposed to be, even though I have to confess that I wasn't really sure what a clit was at that time in my life, hah hah. Anyway, she sure seemed to like it, because she started groaning harder again, and then she started to push her asshole onto me, actually fucking me herself with her ass.

I started fucking back into her butt, the two of us erect on our knees, spooning, her ass grinding into my crotch. This time, while she was giving out with a little "Yiii" shout of shock everytime I shoved into her as deep as I was getting in that position, she didn't say no. In fact she was trying to push back against me harder and harder, and curving her back so my cock would go in as deep as it could go. "Yiiiiihhhhh", and then a grunt, sort've an "Uuuugggghhhh" of pleasure everytime I pulled out. She was making sounds constantly now, it was "Yiiiiiihhhhh ...... uuuugggghhhh", "Yiiiiiihhhhh ...... uuuugggghhhh", and then when I started to stroke faster.  "Ahhhh, Ahhhhhh,  Ohhhhhhh,    Yiiiiiihhhhh ...... uuuugggghhhh", over and over as her asshole relaxed and I fucked into her slippery and smooth rectum. The sounds she was making are still burned deep into my nervous system, man, somehow I knew she was in serious fucking exctasy from my dick in her ass, that she was putty in my hands, completely at the mercy of my manhood sliding in and out of her bottom. What a feeling of power and delight. I'll never forget it. The anal surrender of a young woman.

Fucking in that position was tiring, though, and when we started kissing we ended up on our hands and knees again, she underneath me with my cock now nestled full length in the tight tunnel of her asshole. I start fucking her again, but she wasn't ready, and cried out, saying, "That hurts, it hurts again, hold on a minute, pleeaase!". Which I do, I hold still. Which isn't that easy when your on your hands and knees in that position, but I do it. " When you're ready, you fuck me, okay?", I says, and she nods, and then she says "Can you put your fingers back on my pussy again, that really helps.", so I do, I reach underneath us and twist around till I find her pussy with my hand. I just stroke my fingertips up and down her slit, and sooner than I expected, she started making those sounds of pleasure again. I realize she is still soaking wet, and before long my fingertips have found the flower-like mouth of her vagina, and I am finger fucking her again. Well, I'll tell you, this finger fucking works like magic. Not thirty seconds after my fingers are thrusting into her pussy she starts bouncing her ass back onto my dick.

Debbie was only moving about an inch at a time, but my cock was already shoved pretty deep into her asshole, so the friction of her ass-mouth and the inside of her anus on my cock was just about perfect, loose enough to slip and slide, but tight enough to firmly suck at my cock. Debbie started to grunt in time with her pushes back onto me, sort've an "Oh,oh", "Oh,oh" sound, with a loud "Oh" when my cock was in as far as it could go, and a softer, more pleasure-filled "oh" when she pulled herself off of my cock. I kept finger fucking her pussy mouth, and, even tho my position wasn't a good one, I started to fuck back into her ass with my hips.

"Oooohh God!", Debbie moaned underneath me, as both she and I sped up a bit, her pushing her ass back, and me fucking into her anal mouth. Then she screamed again, a short sharp "AAAHHHH!". "Are you okay?", I asked. She just nodded her head up and down, hard. I had stopped fucking her, and she looked back over her shoulder at me, and didn't say anything, but started to push her ass back on my cock, grinding her ass into my crotch. Then she crouched down a bit, and pulled her ass up off of my cock about two inches,  and slapped it against my crotch, forcing my cock into her asshole.   "Ahhhhgggghhh - ohhhhohhhh", she moan-grunted. She did it again, and grunted even louder.   Again. This time the sounds were more desperate. She pulled herself off again, this time moving more slowly, just a quarter inch a second, sliding off my dick, moaning at every millimeter. When she stopped, she just held still, gasping. Then she said, "Jesus Christ, what do I have to do to get you to fuck me harder?".

Let me tell you, this wasn't the first time I had trouble figuring out what a woman wanted me to do during sex, but I don't need much more of a gold-plated invitation that that!

I didn't say anything, but moved into a better position, not crouched over so much. I grabbed her hips and pulled her up into a classic doggy style. She moaned as I made her move. I started to stroke into her asshole. She took the first stroke in silence, then as I pulled out she started to groan. I fucked into her again, moving pretty slow still, but I pushed the whole length of my cock into her and ground my hips against her asscheeks. Her body shuddered. Oh man what a sight! What a feeling to watch her body take my cock in through that secret anus. When I pulled out I saw her anal mouth suck at my cock, like a rubber tube almost a half-inch long wrapped tightly on my dick shaft, holding onto it trying to keep me inside of her.

Debbie seemed to like the withdraw stroke more than the entry stroke, because when I pulled it out slow like that, watching the way her anus wrapped around my dick shaft, she moaned like a cat in heat, almost a howl of pleasure. I pushed back into her, harder and faster than before, and she sort've squealed, a high "EEEEE". Then I pulled out slow again.

Her whole body stiffened and shuddered, and she moaned loudly, "Ohhhh God! Ohhhh God!." I shoved back into her, and pulled out slow again. "Ooooohhh my fucking God!", she shouts, pushing her face down into the bed.

I don't know why, but I decide to fuck her harder. I push my cock in, and notice that her asshole is getting looser around my cock. I take 3 or 4 strokes into her, like I was fucking into her pussy from behind.

For the first few strokes she is silent, just stiffening and shuddering like she was before, and then she starts to blubber something incoherent, "OOWWWW GAWD AGGGHHH FUUUUHHHH, OHHHH MUUUHHHH GAAAAWWWW...! She thrashes and jerks, and then stiffens her whole body, arching her back, and suddenly I can feel her asshole clamp down on my cock, and she is screaming "AAAAHHHH - AHHHHH!" and gasping and shaking.

I realize that I am seeing my first female orgasm. I had never been sure what the fuck an orgasm was supposed to look like before.

I stroke into her one more time, and this time when she shouts I know it's not with pleasure, but with something like panic. "Don't move, please don't move, it's too intense, it's too intense, just please hold still!". Well, I try to hold still. She reaches back and clutches at my arm and pulled me down towards her. She moans deliriously as my cock moves inside her, but somehow we end up lying on the bed in spoon position, my cock still embedded in her ass.

We are kissing and talking sex-blasted lovers talk, mumbling meaningless things, "Are you okay?", "You are so beautiful" stuff. After a few minutes, tho, she says "Oh god, I think I have to go to the bathroom...". I pull my cock, which is still half hard, and of her ass, and she "Yikes!". She put on a robe, and ran down the hall to the bathroom.

I wiped myself off a bit, and pissed in this little sink that was part of this girl's dorm accoutrements, part of a half walk-in closet deal. A sink in your dorm room, imagine that shit!

When Debbie came back in, she seemed a bit nervous. She sat down next to me and said, "Are you mad at me?". "Jesus no!", I said, "Whyever would you think that?". "Well,", she said, "I know you didn't, you know, squirt your stuff into my bottom.".

I said, 'It's okay, don't worry about it...". She was silent for a second, and then she said, "Well, we can do it again if you want to....".

 

authors note: I never did fuck Debbie in the pussy. We were together only a couple of weeks, and I did fuck her in the ass again that night, and several more times. Boy did she get pissed at me when she learned that it's possible to get pregnant from anal sex, if the semen drips out into the vagina. Whoever she married sure got himself a top quality anal slut. A girl who loves anal like Debbie did is a treasure!

 

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