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I met Annie in bar the week before Halloween. The bar was having a costume contest and we both ended up winning money (I took 3rd, she got 1st). From there we just started dating. I was very deliberate with her because I was just getting over one of the more painful of my breakups and I wasn’t sure if I had wanted to jump right back into things. Still, I couldn’t possibly pass up a chance at dating Annie. She was young and very beautiful with a wonderfully sardonic sense of humor and an impeccable sense of style. She had red hair, cut short into a Donna Reed-type flip which framed her angular face perfectly, almost angelically. She topped off the look with a kicking pair of librarian-style cat eye glasses that only made her beautiful baby blues that much more impressive.
Beyond that she was physically very different from almost any other girl I’ve dated. Whereas I tend to date short, petite girls with small breasts, no hips and tight asses (that’s not a preference per se, I think it’s a by product of the fact that I’m a little short- about 5’7”), Annie was a departure. While she was tall and curvy, her 34 DD breasts still looked a little large for her 5’9” 125 lb frame. I’m not a tit man, I generally like the whole package, but I definitely learned to love her breasts as much as I loved the wonderful curve of her hips and ass.
Our sex life started relatively slowly, as she didn’t even go down on me (or allow me to go down on her) until we had been dating for about three weeks. I had just gotten back from a week long business trip and I wasn’t even sure if she was still going to be interested in seeing me when I got back, you know, out of sight out of mind and all. When I did get back I was pleasantly surprised with her welcome. Essentially, she kissed me hello when I got to her apartment, then proceeded to turn out the lights, take off my pants and eventually, with some coaxing, she gave me one of the most satisfying blowjobs I’ve ever had, coming close to deep-throating me and, best of all, enthusiastically swallowing my entire load of cum. Things got even better a week later when she practically begged me to fuck her. I complied, of course.
Right there I came to a wonderful realization. I had known all along that I could very easily fall in love with her and end up spending a good deal of time in our relationship. She was everything that I looked for in a girlfriend, a good conversationalist, honest, loyal, and pretty. On the other hand, I was worried about our sex life. Beyond the fact that it had taken longer than I was used to it taking (which really didn’t bother me, because I knew it was coming), I was concerned that I might be a little too much of a pervert for her. My last girlfriend, a drop-dead gorgeous slut with a body and sexual attitude straight out of Hustler’s Barely Legal, had kind of spoiled me sexually.
She basically let me have my way with her, allowing me to live out all my perverted fantasies that I had picked up while watching hours of porn as an adolescent. She told me all of her freakish fantasies as well, like her desire to take cocks in every orifice at the same time and be bathed in cum while I filmed it. Perhaps my favorite memory is when she dressed up in her Catholic schoolgirl uniform and let me tie her to the bed. First I took pictures of her with and without her white cotton panties, then with my dick in her mouth. Then I fucked her in the ass while she begged me to ram her tight hot hole. She pleaded with me to cum in her asshole, but I did her one better, pulling out and blowing my nut all over her face and hair. It was a great and glorious moment that I expected to be just the tip of the iceberg when it came to my sexual future. Unfortunately my ex turned into the aforementioned iceberg not long afterward when she incorrectly assumed that I would never marry her, so she cut me off from sex. I hung around for another year while she strung me along and gave me a ton of bullshit excuses while I hoped for a return to our life of sexual bliss and depravity. It never came, so I gave up.
Anyhow, the point of me telling you that was that I realized that I didn’t big ass porno have to be too worried about Annie as I was misinterpreting her frigidness as inexperience. While Annie was a bit timid in bed, I knew I could mold her into a first-class, grade A, cockslut with a little work and some time. She already had shown that she wasn’t squeamish about the taste of my cum (or the taste of hers- she regularly kissed me after I had eaten her out), she was certainly horny as we had sex an average of twice a day, she had a growing desire to please me, and had only been with one other person before me, so she wouldn’t be all set in her ways.
Still, I knew that I couldn’t spring everything on her at once and I would need to slowly break down her inhibitions while our relationship proceeded at it’s normal pace. My goal was to take this gorgeous young thing from the girl who got squeamish about fucking with the lights on to a down and dirty whore who would let me watch while she sucked and fucked a row of strange men. That would be ideal, but I would be happy even if she let me have anal sex with her and/or cum on her face (my two main perverted fantasies) once in a while.
So, I started out slowly. It seemed like she was pretty much only used to having missionary-style sex, so one day I rolled her over and let her ride my cock as she bounced up and down on it. she seemed to enjoy the element of control and was soon moaning wildly. I met her thrusts as I cupped and suckled her enormous tits. My hands slid down her hips and squeezed her round ass as she impaled herself on my thick, 7” dick. Taking my experiment further, I let one finger trace the crack of her ass, brushing past her puckered asshole as I watched her face for a reaction of some sort. I got none… there was no change in her already orgasmic demeanor. I figured I wouldn’t push it, so I flipped her back over and resumed hammering her cunt until we both came.
I decided there that I would first try to introduce her into anal play because it’s a bit more mainstream than facial cumshots. I mean, I could explain wanting to poke her in the backdoor a lot easier than explain wanting to shower her with jizz. It should be noted that I am not obsessed with anal or oral sex; I fervently enjoy your standard vaginal intercourse. I just really like variety, and those are two things that happen to really get me off pretty regularly. My ideal sexual life would be a regular diet of lots of different things, including the romantic, sensual, “making love” kind of sex. My prior girlfriend had tried to satiate my sexual appetite while she was denying me her pussy by letting me cum on her face about once a week, and while it was fun and I have some great mental pictures of it (my cum on her face while she was working out in the gym in our apartment complex, my splooge dripping off her chin while she wore an evening gown), it got real old real quick. I needed the variance in activity. But I digress.
The next time I made love to Annie I did nothing out of the “ordinary”, but simply let her come once (I usually make her come a couple of times) before finishing to keep her horny for what I had planned next. After some post sex cuddling, we turned on the TV in my room. As we lay on our stomachs and watched the tube, I began caressing her back. Kissing her neck gently, I let my hand wander down her ass and between her legs. Still dripping wet, she parted her legs and allowed me access to her snatch. I skillfully inserted a pair of fingers into her and played with her G-Spot while my ring finger played with her clit. She writhed in pleasure as I felt her pussy muscles clench around my digits. I let my thumb wander and let it rest on her cherry asshole.
Sensing no resistance, I put some pressure on it, not attempting to penetrate, but simply add a different sensation that would intrigue her in the future. Her reaction was immediate and positive, as her moans increased in intensity, and I am sure that if I had wanted to I could have slipped a finger into her ass. I refrained and simply slid behind her, inserted my cock in her cunt, and pounded her from behind big tits porno until we both came to a shuddering orgasm. As I fucked her doggie style I brought my fingers, still soaked in her juices, to her mouth. She accepted them greedily and licked them clean. I pictured my fingers as a strangers cock as we impaled her at the same time. I completed the scene in my head with the imaginary stranger pulling out and cumming into her beautiful mouth just as I filled her cunt with my come.
The next day, I skillfully maneuvered us into a 69 position with me on the bottom. I love the feeling of someone grinding her pussy on my face, so this was really getting me off on top of her furious sucking of my turgid pole. I held myself from cumming in her mouth by distracting myself and concentrating on my pussy licking. As I started to lap faster, my tongue strayed northward from her pussy and brushed her asshole. I pretended it was an accident, and resumed eating out her sweet cunt. I got adventurous and did it again, all the while checking for reaction.
This time, I snaked my tongue up and lingered at her ass. I bathed in the depravity of it all as I felt her push her pussy more onto my face, but she did nothing to restrict my access to her ass. In fact, she seemed to enjoy it. When I came to that realization, I could hold out no longer and came hard in her mouth. She groaned in pleasure as I pumped my seed down her throat. I took one last lick of her beautiful ass and sat back to concentrate on her clit, aspiring to return the favor she had given me. I had her panting in orgasm almost immediately.
That night, I was awoken to a very pleasant surprise. I was sleeping on my stomach and awoke to the sensation of Anna kissing the back of my neck while she reached around and fondled my hardening dick. As soon as I got my bearings and realized what was going on, I was all over her, kissing her hungrily, building up for another momentous lovemaking session, when she stopped me, put her finger over my lips and pulled away. Confused, I asked what was wrong.
“Nothing,” she replied, “nothing at all. I just feel a bit inadequate in bed”
“Inadequate!?” I scoffed at her. “Why would you feel that way. I think you’re wonderful.”
“No, it’s just that you’re so… experienced, and I’m not.”
Right there, I started to feel really bad, like I had pushed her too much too fast. I felt like a lecherous pig, and I was pretty sure that I had gone to far by being so forward with my anal play over the prior couple of days. I tried to assure her that she had nothing to worry about, but she still seemed apprehensive. I didn’t know what to do, then her eyes cast downward and she spoke up.
“Hunter… why did you… you know… lick my ass?”
I immediately felt horrible and began to apologize profusely, using the fact that I had quite a bit to drink earlier as an excuse, but she would have none of it.
“No, it’s not bad. I actually kind of liked it.”
“Yeah, I liked it a lot, but it made me feel bad because I know that you wanted more but you didn’t feel comfortable asking. I know you want to…,” she paused to collect her thoughts, then took a deep breath and continued, “I know you want to do more… like fuck my… fuck me down there.”
I confessed that I did, but I said it was not a big deal and that I was just playing around and that she shouldn’t worry. I was very concerned that my whole plan had backfired and she now thought I was an enormous pervert.
“You don’t have to apologize, Hunter. I think it’s OK. In fact, I really want you to.”
“What? Are you sure? Why?”
“I’m sure. I want to make you happy in every way, and especially in bed. I also want you to teach me about different kinds of sex… I will do pretty much anything that you want done, and I want to learn and grow sexually with you. I can tell that you want to have anal sex with me, so I want to do it with you.”
Once I recovered in shock that this sweet innocent young girl was basically telling me she wanted to be my personal fuck toy, I regained my composure and blacked porno spoke.
“Well, if that’s the case, then the first thing you’re going to have to do is learn to vocalize things. I want you to let your mind go when you’re in the mood and speak freely. I want you to talk dirty, none of this ‘fuck me down there’ stuff. You’re going to have to beg for it.”
She giggled a bit, then looked me dead in the eye and said, “Hunter, I’m just a young slut in training. Will you please bend me over and stick your big, long, hard cock in my virgin ass?” With that, she turned around, stuck her face in a pillow and her ass in the air. She then reached behind herself and pulled her ass cheeks apart, exposing her tiny hole.
My dick practically detached itself from my body it sprung up so quickly. I knew that I should milk this, though. “No, whore. You’re going to have to get me ready first. Lay down so I can fuck those big round tits.” I couldn’t believe that I was saying this to a girl who not hours before I was worried about using the word “pussy” around. I was in heaven.
She complied and I slid my cock between those mounds of fun, and began to screw her breasts. She was a trooper and licked the head of my dick as it neared her face on every thrust. I decided to go for it all and said “Annie, I want you to know that the next time I do this, I am going to shoot my cum all over your beautiful face. (she squealed… obviously enjoying the dirtiness of it all). You’re going to beg me to do it and when I do cum, you’ll open your mouth and smile as you show me how much you like it.” “I’ll do whatever you want, Hunter. I’d love to feel your cum all over my face.”
“That’s good. Since you’re being so good, I’ll comply to your original request. Bend over, slut, and get ready to take it in your ass.”
She bent over. I grabbed her hips and thrust my cock in her pussy for lubrication. It took a Herculean effort of concentration not to blow my load in her cunt right there, but I refrained. I eased my dick out, and backed up. I buried my face in her ass, shoving my tongue deep inside her hole. I continued fucking her backdoor with my tongue until I felt the resistance lessen. My dick is a good seven inches and it’s pretty thick too, so I didn’t want to assault her with it without at least warming her up first.
I stood up behind her and pointed my cock at her asshole. I heard her gasp as I pushed against her puckered ass. Slowly, I pressed on. The head slipped in and I felt her muscles tighten in response. I told her to relax and push against me as it would help ease my entry. She did, and I started to slip in more and more. I would stop every inch or so to give her a chance to soak in the feeling. The last inch, I couldn’t take it much more and I shoved it in, burying my rod to the hilt.
“Can you feel my cock in your asshole, slut? It’s all the way in. How do you feel, bitch?”
She winced in pain, but powered on through. “Mmmm… like a whore… keep talking. Make me feel like a cheap slut.”
Ohhh, I was digging this… “Ok,” I said, “You’re about to get assfucked.” With that, I started bucking wildly. I heard her yelp in pain at first, but I didn’t care. I just kept pounding. Eventually she got in a rhythm and started meeting my thrusts. I was going nuts. Then she looked at me, smiled her gorgeous smile, winked and said, “Hunter, how’s about you spraying your nut all in my ass. I can’t wait to feel you cum in my bowels.”
Yeah, that did it. I unleashed a torrent of jizz into her ass as she giggled with pleasure. I fancy that she had a little orgasm with me there then, but I’m not sure. Frankly, I don’t think she cared. She was glowing with the realization of her newfound sexual power. She had seen that she could get me off harder than ever before, and couldn’t wait to do it again.
I, on the other hand, was basking in the glow of the knowledge that I had just butt fucked a girl that everyone thought was so pure, and also that I had, again, just scratched the surface of what could come in the future. I would make this girl the ultimate fuck machine. I had no idea, right then, how correct I was. She would eventually become many things to me. She would become my confident, my best friend, and my wife, and on top of all that, the fulfillment of every erotic fantasy I ever had. Those fantasies began to come true, as early as the very next day…
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