This is the true story of the beginning of my anal fetish, from vanilla anal, to something harder and more selfish. My sweet, if somewhat prudish college girlfriend who promised me anything for my birthday, ends with her receiving something she didn't quite expect.
I'm a male, fast approaching his 30's. I'll share the beginning of my little obsession with you. It's quite tame, but this was one of those special times that started me down this path, and has lead me to much less tame desires...
I'm a normal guy, an upstanding citizen and a former military man who left the military, to go to college and become an Officer...
In my mid-20's my attendance at the university placed me in a group referred to as "non-traditional" more because of my attitude, than because of my age. My manners, sense of responsibility and seriousness didn't allow me the luxury of a care-free time at college as many of these `little kids' were enjoying, completely sheltered and oblivious to the hardships of reality. Their priorities seemed so far away from mine, despite my being only a few years older than them, that I had little or no interest in them.
That all changed when I met Karen randomly on one of the universities online chat rooms. She was 21, but more mature than the vast majority of the campus, and we hit it off rather well. Her serious manner and upper-class upbringing allowed us to quickly become close. Romantic dinners with a woman who appreciates good food and entertainment more evolved than fast food and binge drinking was a relief. She was generally quiet, but had a strong personality and the largest brown eyes, so big a man could fall into them. She was short (5 feet even), slightly overweight at 135lbs, not fat and not even really plump, but certainly healthy, which was a relief from all the walking skeletons that seemed to make up 95% of the female population on campus.
She was even sexually active... but in a shy reserved way. Her strict upbringing and aversion to the `perverse' was overcome by her enjoyment of sex in general, although she could hardly admit it.
Our sex life was what most people would call "vanilla." Her only deviation from it was her definite interest in being on top. No, she was not a top, but she did enjoy a good ride, which she would put a considerable amount of energy into. Now for me, I rather prefer a woman on her knees where I can enjoy the pleasant view of her ass... which was the very reason that Karen disliked it so much, as "back there" was too private. She couldn't even say the word "ass" let alone things like "Anal sex," "Butt fucking" or any of those crude things that were too dirty for a well bread girl to talk about.
So as she indulged her enjoyment of being on top, I began to explore things more interesting to me. Not that I minded our occasional sex, but there were more important areas to explore after all. And her ass was beautiful, not small but plump and well rounded. Of course it was fat to her but I definitely enjoyed the view, and I suspect she secretly liked me looking. So, back to the important stuff...her ass, which I discovered to be wonderfully accessible to a probing middle finger, in the guise of guiding myself back into her whenever I would accidentally fall out. I made sure it was a frequent occurrence, allowing me an excuse to feel around back there and to eventually get her used to that feeling, without her stopping until I removed my finger, telling me that she was "dirty back there." God, she was cute when she said that.
Eventually she got used to my finger in there. Her enjoyment of other things allowed her to suffer through it. Despite her continuous protests to the contrary, I began to suspect she liked it, fucking her ass hard onto my finger and even sometime stopping if my finger fell out, allowing me time to get it back in... My innocent, sweet, cultured angel might very well enjoy something naughty like that.
My birthday eventually came around and she asked me for one thing that I really wanted for a present. I gave her my "dirty old-man grin" and asked, "Anything?" She replied with a mischievous twinkle in her eye, "yes" and my jaw almost dropped. Now even to this day, I'm firmly convinced that anal sex never crossed her mind. I strongly suspect that she figured I'd ask to make her from behind, something she usually refused to allow, and I usually asked for.
Not wanting to miss my chance, I asked her if she promised I could ask for anything and she agreed. We had just spent an hour or so indulging her position of choice and she probably figured it was time to treat me to mine. So after going out for a nice romantic birthday dinner, we came home and I asked her if I could now collect my prize (something that I refused to tell her before we got home, allowing her all dinner to think about what I might ask).
Once home (we were actually living in her dorm room – a spacious single) we went and showered, and came back to the room, when she finally forced me to make my wish or lose it. I gladly did, kissing her deeply, warming her even more than the shower did, naked and wet; I whispered in her ear "I want to make love to you... back there." Her body froze and I could tell she was stunned... but I had used all the proper words as to avoid an immediate rejection. After a long pause, I said "You did promise anything. I suppose I could let you back out.... ," Which again was rather evil, because promises were a big thing to her, and I always did my very best to keep all of mine, so she felt obligated to allow me to indulge myself.
To my delight she finally formally agreed and I kissed her deeply again to show her my passion for her, and my thanks. However, to my disappointment, she placed a last minute condition on my birthday present, two actually. One, that I had to stop if she said I had to... and the other, I had to wait for the weekend, which she reasoned it being a long weekend, most of her neighbors would leave to go home. I reluctantly agreed. I was slightly angry but there was nothing I could do... chivalry and all that. So instead, I nudged her onto her knees, and stared openly at her ass as I moved in behind her without any further ceremony. She knew I was disappointed and felt cheated, so she allowed herself to be guided to the floor and to allow me some relief now, as the weekend was still several long days away.
With every selfish intention of enjoying myself on my birthday, I entered her pussy hard from behind. I worked my thumb into her ass and I could tell she felt humiliated, but without protest she allowed me to take her. I took her hard, right from the first stroke, making her grunt and whimper slightly into the carpet as I pictured myself in her ass. Her not-quite broken promise made me somewhat angry and I allowed myself to fuck her roughly, for the first time we didn't make love, but rather I took her and for the very first time I got a perverse pleasure from the noises she was making. I could tell she felt humiliated, and that it was uncomfortable, and that excited me all the more... not because I was hurting her, but because she was letting me. Never once did she try to make me stop.
The weekend finally came, and after a bad week I was in no mood to accept any excuses. She surprisingly didn't make any and invited me meekly into the room that Friday night. All of her neighbors had predictably gone off to enjoy the weekend, and we could enjoy ours in peace and quiet... or rather I could enjoy mine.
She looked nervous, but resigned to keeping her promise. The futon mattress was laid out on the floor, and not in its usual couch position and she had placed a bottle of lotion next to it, so I knew that she was willing to go through with our deal. I asked her anyway if she was ready, chivalry still partially in existence dictated that I give her one last chance to escape my little trap, but she answered only by turning around and pushing her jeans down over her round bottom and then removing the rest of her clothing without a word... I was already rock hard, my balls aching from anticipation all day. I knew I wanted this... and she knelt on the futon facing away from me, staring at a glass faced bookcase on the wall. I suspect this allowed her to watch my approach as she was still quite nervous, but as I was to discover, it was an incredible view of her face as well.
Her plump bottom was in the air, and she was clearly nervous but not saying a word. Probably because she didn't trust her own voice and I didn't want her to get too scared and back out, so I approached quickly and whispered to her as I put lotion on my fingers, that I would get it over with as quickly as possible... I was determined not to go slow, which would let her tell me to stop before I even got in.
With care I pushed my finger into her rectum, that tiny brown/pink hole was very tight. Her mind told her body yes, but her bottom was defiantly and firmly saying NO. I can still feel my middle finger being choked by how tight she was... so much tighter than normal. I loved it. She looked so good. Her nervous whimper as I pushed that finger in, I knew I was going to enjoy this.
Carefully and gently I got up behind her... my hand on her back to console her and assure her she'd be alright. I leaned over her and whispered how good she looked, and that this was the best present she could have offered me, I was sincere in thanking her and I wanted her to know just how thankful I was.
Stiff and hard, I positioned myself slightly above and behind her beautiful pale, virgin ass. My cock could never have been harder in my life. She was letting me do this to her, and she definitely didn't want it...and that excited me even more. Firmly against her ass I pushed with increasing pressure, my 210 pound, 6'3" body made entry easy for me. For her she all but screamed when the head pushed unceremoniously into her most private hole. Her shoulders immediately fell to the futon and her face buried in the single pillow that she had laid down. She moaned into it loudly enough that I could tell it wasn't a moan of pleasure, but she still held her ass firmly in the air. She was letting me hurt her. Allowing me into a place she had been guarding for her entire life and it was mine to enjoy. Definitely mine when I pushed the full 6.5" length of my cock into her. She screamed silently into the pillow, her entire body tense and rigid beyond belief. I stopped for a second in amazement, and then withdrew almost my entire length. She seemed to relax, and the relief in her body became clear until I pushed myself firmly back into place... not a hard shove, but a steady advance and her head came up this time... her beautiful brown eyes and cute round innocent face cringing in pain, all of which I could see clearly in the glass door of the bookcase.
She was shaking her head now. Finally finding her voice and much too loudly she said between gasping breaths, "STOP, stop, stop, stop, it burns... I can't do this." After that final push I began to pull back out as she was saying that. I became somewhat angry, as she felt so incredibly good, but was now demanding that I stop. I pushed in again and she tried to pull away. "I can't! Stop please. I can't do this yet."
"You promised Karen."
"I know, I know... god it hurts. Just stop." I pulled out, frustrated, but obeying my agreement to stop; I rubbed my hand over her back. "It's ok. I stopped." And I had. She stood, grabbed a robe and left to go to the bathroom with tears brimming in her eyes.
I felt bad. Like I'd gone too far and raped her or something. But it felt so damned good. What scared me though was not how good it felt, I had had anal sex before, but rather how much I enjoyed her holding her ass up to me, while I did it while I hurt and humiliated her. I couldn't get the sound of her distressed moans out of my head. I was a sicko.
She came back after a while, and kissed me and thanked me for stopping. She confessed to knowing how much I wanted it, and she PROMISED that I could try it again Monday morning before the other students returned, if I gave her a couple days to rest. I could do nothing but agree, and we watched movies instead, late into the evening. We watched stuff like the Princess Bride and other nice girly movies. I do confess to liking the Princess Bride... but the rest were more to console her. That night we made love normally, I insisted that she get on top and after a few minutes she was enjoying herself, and her humiliation was forgotten. I didn't attempt to even touch her ass until Monday morning.
Eventually Monday came, and the morning was spent cuddling lazily when she finally asked as it neared eleven, if I wanted to try it again back there. Of course I answered with a resounding yes, punctuated by a long deep kiss, which she smiled and returned. I could tell she was still scared but she had felt horribly guilty all weekend for making me stop, that she had promised not to make me stop this time.
An evil bastard might take this as a green light to go far and beyond our previous attempt and launch right into something far more sexually fulfilling now that I had this blanket promise to fuck her and not have to stop, but my interest in such things had yet to develop. I wasn't without my frustration, and her agreement to go through this again, ended my guilty feeling about how I had enjoyed doing it and so we tried again, this time with the promise of being able to enjoy her completely.
Onto the futon again, its blue cover and single pillow awaited me after I returned from my morning trip to the bathroom, and this was definitely an encouragement. Her nervousness was back and her wide brown eyes made her look so sexy and innocent, yet she had prepared for her own ass fucking, something so nasty that I could hardly believe that my prudish little girlfriend allowed, and even prepared for. Once again she told me that she wouldn't make me stop, but that I should go gently because she thought I had torn her a little bit Friday night.
She knelt on the futon with her ass in the air again, and put her shoulders on the mattress as well. Her breasts, an ample C cup were still visible squashed sexily under her and her ass was pointing right at me, all without prompting or coaxing. She was letting me hurt her again. She watched me in the glass cabinet again as I picked up the lotion bottle and lubricated her tiny hole. She sucked in her breath a little when my finger entered and she said the lotion stung a little where I had torn her, but she didn't make me stop. I couldn't help but think how incredible this was. She wouldn't look at me directly, but she was watching my every move in the glass door. I slipped down my boxers, and stood behind her looking down at her wonderfully full ass. Her bottom, so open and displayed voluntarily even thought she knew it was going to hurt badly.
I slicked myself up with the lotion and knelt behind her and placed my cock against her tiny hole. The sun was up, and I could see everything with perfect detail that even to this day I can remember. The sweet cherry smell of the lotion, her nervous, shallow breathing and the wrinkles of her semi-virgin anus...the anus that in moment I would drive myself into.
Secretly I watched the glass, her face now shown with fear and anticipation of pain that would surely come. I couldn't resist that excitement at her giving herself to me, knowing I would be hurting her tender ass-hole again. Firmly placed against her ass, I gripped her shoulders and with one long and firm push, I sunk myself down into her ass. I watched in what seemed like slow motion as my shaft forced itself into her, and she clawed the futon and buried her face in the pillow and screamed long and loudly between her clenched teeth. I almost came right then.
I pulled out of her quickly and her head came up and we locked eyes in the glass door. A second before I plunged back in I took the pillow away from her, and tossed it aside. I needed to hear her. I had pulled out of her "to let her rest" but it was the entry I wanted to enjoy again. Her ass closed up and I once again placed my head against her tiny opening. Gently I nudged her knees apart further and she opened them up wide, my hand pushed the small of her back down arching her ass up at a better angle and she obeyed silently. She was really letting me do this. So sweet, and so innocent, I was about to sodomize her roughly and she knew it, and was letting me do it...
My cock entered her again, this time hard and fast, and I began to stroke in and out of her tight, tiny ring. I can only describe her response as a sobbing wail between clenched teeth and into the futon mattress that we were on. From the sound she was making, I knew I had torn her anus again. I couldn't help but fuck her harder. After a few more steady strokes, she was breathing in gulps between sobbing moans, each exhale she whimpered over and over "it hurts, it hurts, it hurts" as a chant while I began fucking her in earnest.
With my right hand I stroked her hair as I paused for a few seconds to keep from coming, but to her it was because I was worried about hurting her, and I turned her head to one side and her tear streaked face was bright red. I wanted to hear her without the futon getting in the way.
Oddly balanced with one hand on her hair I began to fuck her again, and watch her beautiful face cringing in pain with each stroke as I went faster and faster. She turned her face back into the futon mattress to hide her almost constant crying now, and I couldn't believe she was still letting me take her. I was sawing deeply in and out of her and could barely make out her whimpering as I did so, but it sounded like she was repeating "I can't, I can't, it hurts" and I knew my time was limited, so I fucked her harder, leaning down on top of her as she began to unconsciously pull away. Quickly grabbing the pillow from earlier, I pushed it under her hips, and she collapsed on it, but not so much that I couldn't still enter her.
`Stop, stop....please stop!"
I pretended not to hear, because I would have to stop without coming if I did hear it, and I needed to come. My full weight was on her now and in between breaths and clenched teeth, I hissed "I'll come. Just let me cum. I'll be quick. I promise," punctuating each sentence with a hard, deep stroke. She seemed to relent, but continued to whimper and moan with each of my now desperate thrusts. I was almost raping her now. Her sobs and tears clearly visible with her face in the air, I was making her scream silently by twisting my hips savagely each time I was in to the hilt. With one final shove I was in to the root when I began to cum uncontrollably, shooting what seemed like a weeks worth of hot salty cum into her now torn anus.
I collapsed on her, and her plump ass seemed to fit wonderfully against my hips. We were both breathing hard, and my cock still spurt a few more times, but she was no longer screaming and was just laying under me breathing hard. Still buried in her I didn't move because each movement hurt her terribly, and I told her I would just lay here and let her recover. I rolled my hips a little "getting comfortable" and she gasped, as she wiped tears out of her eyes hoping that I didn't see them. I don't believe Karen realized just how loud she was, or how much I loved what she sounded like. My cock was beginning to soften as the last few spurts emptied deep in her bowels. I moved my now softening cock out a little, and back in and she barely made a sound except for an occasional gasp. She was clearly relieves as I stoked her hair and told her just how incredible she was, and how much I loved her and her birthday present. I carefully pulled out and as my head came out she hissed, sucking in air between her teeth, and I laid down next to her, softly kissing her cheek and neck.