This story is a work of fiction even though parts of it were inspired by real-life incidents. Any similarity to real people, living or dead, is coincidental. All the characters are 18 years of age or older. Do not read this story if it is illegal to read about explicit sex where you live.
(Edited by H.S.)
I awoke the next morning in Madison’s bed. She lay next to me in a deep sleep, tired out from a night of hot, high-energy fucking, and as I looked at her, her soft, peaceful breathing made me want to go back to sleep myself. Even in her slumber she looked regal and graceful, a “peaceful sleeper” as I heard someone refer to it once. Madison was beautiful and growing more beautiful in my sight with every passing day.
Was this a sign that I was starting to have feelings for her?
I was afraid of what the answer to that might be, not wanting to endure that horrid, obsessive yearning for a person who didn’t really care for me in return. I knew that feeling all too well, but the year plus of heartache I had suffered through with Kerry had just now been washed away by my sex-infused few days since meeting Madison.
She had broken my heart, and I’d truly loved her and she had loved me, but she fell out before I knew it, and I was crushed like a pea. Kerry McNamara was a yuppie, a new person in the old neighborhood, a renter rather than an owner like Madison. Growing up in the old neighborhood had given me a sheltered, small-minded outlook, and Kerry was the one who woke something within me, a desire to be a better person, open to new things and new ideas.
But as our relationship moved forward, I discovered that Kerry was really the shallow one. I came to realize that she was ashamed of me, not only because I was younger, but in her mind I was just a dumb native without a college education. This wore heavily on her, and she would say things like, “How can I introduce you to my family? You work in a kitchen,” and, “I can’t be with someone who doesn’t have a degree,” said through her frustrated tears of entitlement.
She was torn trying to live two lives, one with me and another with her preppie-yuppie friends. I would ask her why I hadn’t been invited to this party or that get-together, and she would just brush it off with, “You’d only be bored,” or, “It’s just us girls getting together,” which were lies.
The funny thing was, we’d met at one of those get togethers! Kerry had thrown a party and had invited a common friend, Davey, who, in turn, invited me. Davey knew Kerry through pure logistics: She rented an apartment in his building. Kerry caught my eye, and I asked Davey to introduce me. Her light, freckled skin, green eyes and asymmetrical haircut were fresh air to me. Her thin, athletic figure didn’t hurt, either.
All the girls I grew up with were dusky brunettes with Mediterranean features, so Kerry’s Irish/WASP look was something new and exotic.
Once we were introduced to each other, we spoke somewhat briefly and interacted sparingly throughout the night. I thought of it as nothing more than polite conversation, and romance or even just “hooking up” were not on my mind at all. But as the evening progressed and the crowd dwindled, I found myself alone with Kerry. I can tell you with complete honesty that I had no intentions other than just being a nice guy and helping her tidy up her apartment.
Looking back, I guess I’d missed every signal that Kerry had sent out the entire night. I sure wasn’t expecting her to walk up and kiss me, but that’s just what happened. She approached me, put her hand on the back of my neck, and planted a long, passionate mug on me.
Our post-party cleanup immediately turned into a hot makeout session. Kerry unbuttoned my shirt and pants while I blew in her ear before kissing and licking her long, feminine neck. Since she was taking the liberty of undressing me, I returned the gesture by sliding my hand up her skirt and ripping off her panties. She stopped undressing me and pulled off her own top and bra. I didn’t see any good reason why she should only be nude from the waist up, so I knelt down and slid her skirt off.
I already knew where her bedroom was, because that’s where everyone’s coats had been kept during the party, so I lifted her in my arms and carried her to her bed like a groom carrying his bride across the threshold, except my woman was naked!
My finger brushed the inside of her knee when I placed her down on the comforter, and I could feel the slick wetness there, and it ran up her inner thigh all the way to her neatly trimmed vulva. I couldn’t believe I’d excited her enough to make her pussy juice flow all that way down. My arousal piqued with that thought and the unmistakable bouquet in the air from her womanly honey. I placed my mouth on the inner part of her leg and with my lips and tongue followed the train of her flavorful wetness up her leg until I came to the piping hot gash of pink flesh from which it emanated.
She orgasmed after a few long strokes of illegal bahis my tongue up and down her juice-dripping vaginal lips, and then she came again from some jabs to her honey-engorged clitoris.
“I want you inside me,” she begged me in that deep, breathy voice that post-orgasmic women have. I climbed her trim swimmer’s body, and we were face to face. Her cunt was so drenched in pussy juice that my cock slid into her effortlessly as her sex enveloped my rock-hard manhood. With ten or twelve of the hardest thrusts I could manage, I was about ready to pull out and blast my pent-up jizz all over her flat belly. Just as I prepared to withdraw my hog from the hot, spongy wetness that was her cunt, she stopped me.
“No, it’s OK. I’m on the pill. Come inside me, please,” she urged, and I did so, not willing or even able to hold back any longer. Those familiar contractions shot hot loads of semen into her cockpit.
I thought about only spending the night with her, a one night stand, and that would be it. But to my surprise, Kerry pursued me, at first, anyway. She stuffed my mailbox with letters and cards, sought out my phone number and called me out of the blue “just to see how you’re doing.” Not long after, I was worshiping the ground she walked on. I guess I was the male version of “easy.”
And then, no sooner than she’d sunk her hooks into me, she became ashamed of me! Our sex life was active, but one way only. I always gave her multiple orgasms, always was more than willing to eat her pussy and ass to make her come at least twice before my cock became involved. Despite all that I gave her, it took forever to get her to return the oral favors, and when she finally deigned to do so, it was with a huffy air of distaste and the stern admonition that she would not take my semen in her mouth, let alone swallow it.
All of this resulted in a halfhearted blow job that I halted midway out of dissatisfaction, opting to just mount her and pound her pussy instead. Deep down inside, I knew I was only a dildo with legs to her, but I was so in love I didn’t want to believe it. I didn’t have enough money to take her to the upscale, trendy yuppie places she wanted to go: trendy trap joints serving microscopic portions on giant plates with expensive microbrew beers and even more expensive wines. I knew these places from being in the restaurant business, and they were all sizzle and no steak; gimmicks, and nothing more.
On several occasions, we’d be in some establishment, and they’d ask for my ID, which I couldn’t produce due to the fact that I was under the drinking age, and Kerry would get angry with me and storm off, as if my youth was my fault. I was insufficient, and then her acquaintance, Gerry, who was “just a friend,” surfaced. He was a goofball as far as I could see, but he could easily afford to take her to the swanky haunts she wanted to frequent. Little by little, I was being dumped like trash that had only a minor sentimental value.
Madison was even further out of my league, and she could buy and sell Kerry in every way imaginable. How could I make this work, I wondered constantly.
I told myself not to get attached and to enjoy the time we would have together as a sort of extended one night stand. If I were granted another night of hot butt sex with Madison, awesome, if not, enjoy what I’d had and move on.
I tip-toed out of the room, opting to use the bathroom down the hall rather than the one attached to the master bedroom and disturb Madison’s rest. I used some toothpaste on my finger to freshen up and then took a quick shower, dried off and returned to my place on the bed next to my co-conspirator in the art of backdoor carnality.
After a while, Madison stirred and turned to me. She let out a yawn and a groggy “Good morning.”
“Good morning to you, my dear,” I replied. “Did you sleep well?”
“Yes. Someone wore me out a little,” she said, her sense of humor and sexuality never far away, “but that assured me a sound sleep.”
“Wore you out, did I?”
“Like I told you, it’s been a while since I’ve gotten fucked that hard and that often.” Madison gazed down at my half-mast cock and said with a smile, “Wow! You’re hard more often than you’re not!”
“Well, you make me that way,” I retorted. All this hot talk this early in the morning had gotten me visibly excited.
“No, I just think you’re naturally that way. I mean, gasoline without a match is still gasoline,” she said as she arose and walked into the bathroom. I heard the sound of running water as she washed up. In a short while, she emerged, wearing only a towel. A cloud of steam enveloped her and followed her out. She threw herself onto the bed next to me, and we kissed as she reached down and cupped my scrotum gently in her elegant hand.
The soft caress was more than enough to send my half-hard dick into overdrive in half a second. Madison wiggled down to be eye-level with my cock and balls. I lay on my back, anticipating a nice early morning illegal bahis siteleri blow job. What a woman! She wants to suck me off first thing to start my day off right! Continuing to cup and caress my sac, she made an “OK” sign with the thumb and forefinger of her other hand and began using it to lightly stroke the shaft of my cock instead of taking it into her mouth.
I peered down to see what the delay was after having waited a while for her gorgeous lips to begin working on me. She was staring at my stiff sex organ as if she were in a trance. Finally, she broke the silence with a question: “So tell me, what did Kerry say about your penis?”
How did she know I’d just been thinking about Kerry? I was taken aback, stunned that she was able to read my thoughts, and then quickly dismissed it as coincidental. I had only mentioned Kerry to Madison once, but she seemed to already know what type of relationship it was. Even with these thoughts racing around my head, I managed to give Madison a candid, honest answer: “Nothing. We didn’t go into detail, not much dirty talk. She was sort of stuck up, and. . .”
“You have a beautiful penis,” Madison interrupted in an even tone that was sexy in its seriousness. “It’s really aesthetically beautiful,” she continued as she revered my “beautiful penis,” devouring it with her eyes.
I was flattered by her sincere compliment, and I thanked her, remembering that for Madison, sex was sacred and serious. She always engaged in shameless, frank sex talk with that even tone of hers that made it all seem so much sexier in its emotionless, blunt way.
“The cock head is flawless in its shape. The shaft has the ideal width and perfect curvature. Oh, and the veins are gorgeous, bulging out in the right places,” she opined, still gazing lovingly at my meat pole.
“Is it big enough for you?” I asked in my naive way, still needing approval.
“Do you know how many inches you are?” A wry smile crept across her beautiful face.
“You mean, you’ve never measured your own cock?”
“No, never. I always thought it was a weird and stupid thing to do.”
“Oh, come on! All guys measure their cocks.”
“Not THIS guy.”
“Really!” Madison exclaimed with a scrutinizing raise of her lovely brow.
“So, is it big enough for you?” I probed again.
“I can’t believe this! You don’t even know what you have!” she said with a smile of genuine appreciation of my humble honesty. “Well, let me tell you, your cock is perfect. They should cast it and make dildos from it, it’s so beautiful!”
“Uh, thanks,” I said through my blushing face. It was the best compliment I’d ever received. I was moved by her affirmation of my manhood, and I felt the rare feeling of acceptance that I’d been seeking so desperately.
Madison’s next question interrupted those thoughts and almost knocked me off the bed. “So, what does our friend Gemma say about your beautiful penis?”
Embarrassed, shocked and a little vexed, I shot back, “Nothing. She wouldn’t have any idea.”
“But you HAVE Fucked her, no?”
“NO! We are not fucking. We have never fucked. Furthermore, Gemma is my boss and-your-question- is-weird-and-unsettling-please-stop!”
“But you want to fuck her, or at least have thought about fucking her.”
“NO!” I answered, somewhat more perturbed.
“I saw you ogling at her the night we met,” she chided playfully. “Like sneaking a peek at your hot cousin’s behind!”
“She’s my boss, and that’s it.”
“Don’t be ashamed, dear. She’s a beautiful woman, inside and out. Gemma is so sweet and kind and. . .”
“You don’t work for her,” I sneered.
“Okay, okay. I just thought. . .”
“You thought wrong.” I shot back. We were both quiet for a moment, and Madison was lying on her back next to me. It was time to change the subject. “Well, enough about me,” I began. “How about we turn the tables and talk about the Mysterious Madison Foss?” I asked, both to lighten the mood and perhaps have that early morning sex after all.
“What would you like to know? I have nothing to hide and everything to tell,” she retorted with that sexy smile and smoldering stare.
“Let’s see: It’s about our favorite subject.”
“When did you know you were anally inclined, and when and to whom did you lose your anal virginity?” I wanted to know this even if I was becoming attached to her and might later feel a slight pang of male jealousy. Carrying the knowledge of Madison’s rear-end asscapades might bother me in the future, being somewhat sheltered in my small-minded, small neighborhood way. But the curiosity of the events and experiences that made the Anal Queen that lay next to me who and what she was, well, it was irrepressible. It was a curiosity so strong and erotically stimulating that I was asking questions instead of working our foreplay into another hot romp, so again I queried, “When did you discover that you had an anal fixation?”
Madison considered canlı bahis siteleri my question for a moment, and then she began, “I guess always. Well, I knew I wanted it when I first heard other girls talking about it and was slightly turned on by the idea. They would talk about how only a super slut would give her ass to a boy. They would say it’s even worse than if you sucked a guy’s cock, so I was intrigued by the naughty, taboo nature of it. Then I forgot about it for a while ’til later when I started to masturbate regularly.”
Not only was I learning about life in general, I was becoming more and more studious in my sexual education. I was clueless about women masturbating. I was under the impression that women didn’t play with themselves, in real life anyway. “You mean women play with themselves? For real?” I asked.
“Of course we do! All the time, and any woman who says differently is a liar.”
“Wow.” I was yet again in awe of both the truth and Madison’s openness.
“Just as much as you guys, if not more. We can get off driving down a bumpy road. We’re sexual beings just like you men are.”
Listening to this was almost as good as watching porn. My pulse quickened, and I felt those sexual butterflies in my stomach flutter in full, astonished enjoyment . The feeling of being let in on a deep, dark, sexy secret, like when I witnessed Gemma sucking Big “D’s” cock. What the fuck! Why does Gemma keep intruding on my thoughts? I thought to myself.
Madison continued. “Getting back to your question, I would wait ’til I was alone. I would draw a hot bath, as hot as I could stand it.”
I hung on her every word.
“All the blood vessels would open up, and I would get flushed with color, an invigorating feeling. I would loosen up both mentally and physically. All the muscles would warm and relax, and then I would start with my nipples. I would tickle and then pinch them. Then I’d caress my own body, my side and tummy down to my hips. Then I would begin to gently rub my entire pussy with my hand, eventually spreading my sex open and feeling the hot water pour over my clit.
“At first I would just enjoy the sensation but would little by little begin to masturbate my clitoris with my middle finger while I spread my vagina open with my index and ring fingers. Once I was all worked up, I realized my pussy would expand and open up and that my wonderful joy button would swell with my excitement. At first I was playing with the middle finger but then I no longer had to hold my pussy lips open. I could rub my clit with two, then three, then all four fingers, and what started out as slow and gentle would become vigorous and spirited rubbing. I would by now also be gyrating my hips and body ’til I came.”
Madison was looking like she was enjoying reliving the fond memories of pleasuring herself as much as I enjoyed listening to it, all the while knowing how much she was wrapping me in her sexual web. There was also honesty in her tale, for sex was a sacred “process of pleasure” and masturbating was a form of sex and therefore important. Make no mistake, she loved hardening my cock with her stories and loved being open.
Perhaps we both shared yet another sexual trait: that weird, out in the open, carefree feeling that I had lately found so gratifying.
“I was masturbating like that one fine day, and as I got worked up and was in the throes of an oncoming orgasm, bucking and rubbing, my hand accidentally slipped past my pussy and slightly grazed my asshole. My middle finger inadvertently caressed the circumference of my anus. It was as if I had pressed a button that was directly wired to the pleasure centers of my brain, shocking and sensual, and I wanted more of it.
“Just like you, I had been tainted by the opinions of some of the company I kept. I was under the impression that if you touched your own asshole you would hurt yourself or you were a dreaded ‘slut,’ and it was totally wrong and the ultimate of taboos. I was led to believe that a girl who let a guy put his penis in it would ruin her life. She’d get a scarlet letter; an ‘A’ for ‘anal’ instead of ‘adulteress.'”
Madison sort of giggled at herself, both for her literary joke and at her old mindset. “But how could I have denied myself of what secretly felt so good?”
I shook my head in agreement.
“I mean, why should I? It wasn’t as if anyone would know. I came to terms with my desires, and after that, I slowly incorporated ass play more and more into my masturbating ’til it just became standard. I suppose you could say that I fell in love with my own asshole.”
She smiled at me and my erection, enjoying the power that her mere words had over me. I wanted to play more as well. Feeling like a sexual talk show host, I pressed her for more: “So that’s how it started, but tell me, when did you have a dick in your ass for the first time?”
“Well, I was in collage, and my first steady sex partner, Ron, tried to do it to me a couple of times but he was clueless. And to think I had waited forever for him to get around to it! I was like you: too shy to ask him for it. When he became bored enough to finally try something new, he had no idea what he was doing, and in both attempts failed to penetrate me anally.