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Anal Masturbation

This story came about quite unexpectedly. It involves a good friend of mine, William. We have known each other since high school and he was one of the few I have kept in touch with over the years. By coincidence, we have both been living in Knoxville together for years. It has not been uncommon for us to hang out, have movies nights, or a night out on the town. I hooked him up with one of my girlfriends, Sarah, and the two of them seemed to hit it off well. So well, in fact that they dated for about two years.

The end of the relationship came when Sarah got a job in the Nashville area as a teacher. They tried the long distance thing but ultimately it didn’t work out. There is a reason for that.

Sarah, as one of my friends, is a bit of a horn dog. She loves sex. I mean who doesn’t. She also really cared for William. A lot. When she first moved to Nashville, they had planned a beautiful trip to the Caribbean, to give them time together and away from the stresses of the every day. A wonderful idea, right?

Well, as the months passed, Sarah began to get those “urges”. Torn between her love of the cock and her love for William, she gave in to the love of the cock. I can’t blame her. Their relationship changed when she moved. Nothing really major, just subtle things. I guess you can say personalities didn’t sync up anymore.

Anyway, William wasn’t too distraught. They stayed friends. Sarah’s honesty was definitely the reason for that. Sarah went on to become the harlot of Nashville (wink, wink, just kidding). William instead didn’t date. At all. We still hung out and did the things we always did. It was like Angelica Rose and her plus one.

When the time came for the trip to the Carribean, he asked me to go with him. Because he couldn’t get his money back, he never canceled the it. He had hopes that maybe he could find someone. When he didn’t, he asked me. After slugging him in the shoulder for considering one of his closest friends either a consolidation prize or a reluctant travel buddy, I said sure. Actually I believe my exact words were “Sure, why not?”

Que up the Sofia Petrillo story, “Picture it….”. We had a good time driving to Key West, joking and singing horribly to even worse music. The cruise was awesome. He had never been on a ship like that before and it cool seeing it through his eyes. Kind of like your child the first time they go to Disney World and see their favorite character. It was like that.

We checked in with hopes that we could get separate rooms as opposed to the suite he had reserved for he and Sarah. Long story short, we were roomies. Not bad considering we had stayed the night at each other’s houses since we were kids. It was like a cooler, more expensive night at his house. Or my house. You decide.

William and I had a blast the first day we were there. We went diving, walked the beaches, looked at hot men and women —complete with the point system too! That night, we decided to try one of the local spots that was suggested to us by the (really cute) guy behind the reception desk.

When we were seated, we became increasingly aware that it had a very “free spirit” vibe. We ordered our dinner, drank, and listened to the wonderful entertainment. We weren’t aware of it at the time, but apparently at ten p.m. the cabana becomes a dance club.

As neither of us have done the club thing in quite few years, it was a nice change of pace. They started off with some “Holiday” and ventured into Kylie Minogue about an hour later when we finally stepped off the floor. We were more than just a little close on the dance floor. We bumped, grinded, and practically had sex while we let go of our inhibitions there.

Ordering a few rounds of drinks, somehow the conversation turned towards how much fun dancing was. I teased him about being an incredible dancer. You know what they say about a man who can dance, supposedly was the kind of stuff we teased each other about.

He mentioned that it was the closest he’d come to sex since he and Sarah split up.

Which was almost a year prior to the trip. What the fuck, right?

I told him that he needed to get back on the wagon and not waste his talents. To which he responded to “what talents”? I told him that it was his dancing and sexual aptitude as a result of it. He knew I was lying. Or at the very least holding something back.

Now keep in mind, we’d known each other for the better part of thirty years. He was six years younger than me. Most of the girls he dated… “talked”. Sarah thanked me for introducing them because of his “condition”. A “condition” that William had thought I was referring to now as evidenced by his increasingly red face.

I’ll spell it out. The “condition” I speak of is William’s supposedly enormous cock. It is the stuff of legend according to every woman he’s dated. I figured they told me because it wasn’t big at first or that he sucked in bed. You know, make up stories to share in high school type-of-thing. At first, yeah I could believe it. The menderes escort reality of it was when Sarah told me and I didn’t believe her. It wasn’t until she provided me photographic evidence that I believed her.

As uncomfortable as it was for William, the “truth” came out. I joked and laughed at his expense while noting that several people who’d walked past us looked. Mostly woman, but a couple of guys smiled and admired him too.

To make it worse, I told him about the picture I saw.

His face was about as red as a beet. I could see the beads of sweat coming down his forehead now. I reveled in his discomfort. Until he turned it around on me.

With my knowledge of his “condition”, he wondered why I never tried to fuck him. My response was because he was my buddy, my William. I couldn’t sleep with William. I admitted a slight attraction to him in high school but once I got engaged, he became something like a brother to me. I reminded him that he stayed the night with me during the lonely nights when my ex-husband was away on trips and consoled me when I discovered his affairs. I also confided in him many of my sexual exploits, starting with John, when I got divorced. He did the same with me. There wasn’t much off limits to us.

This teasing dynamic between us has always existed and we’ve never truly thought much of it. He challenged me, playfully, at first to take him on and try it in response to my razzing of him. I did the “eeehhh” and “gross” thing that little kids do. Honestly I don’t think I had ever thought of William in a sexual way. Completely odd considering my sexuality, right?

Well, the thought was put into my head that night and the more we teased and played with the idea, the more receptive I was to it. Even when we went back to the dance floor, the teasing continued. Except that this time, the teasing was more like a full-blown attempt at getting into each other’s pants. The lines between playtime and business, as it were, had become increasingly blurred.

I think I became aware of William as a man the moment I slid down his body and saw his erection bulging through his slacks. When I rubbed myself against him as I rose back up him, I felt it press into my belly.

He smiled at me wickedly, telling me not to play with fire because I might get burned.

We continued to dance through three or so songs, but it wasn’t until they turned down the lights even more and they changed the tempo from dance/hip-hop/techno to dance/dance (if you catch my drift) that we even cared. Well, “Angel” by Aerosmith was the first slow song they played.

Instead of leaving the floor, we looked at each other for a long moment. He extended his hand and I took it. Pulling me to him, we began to slowly tiptoe into familiar but now awkward territory. I remember resting my head into his shoulder and chest for a great majority of the song. William was always a great dancer. Comes from years of taking dance lessons, I suppose. Seriously.

Maybe midway through the song, I looked up at him to see him looking down at me. Our eyes caught. We smiled, warmly, before reality reminded us of who the other was.

As our heads dipped closer to one another, I had not realized that “Angel” was over. Continuing to dance through “Careless Whisper”, something odd happened at the end of the song.

We kissed.

It was innocent. Brief. Yet it left us in the far end of the cabana, searching for meaning while everyone else around us was dancing.

I mean, we kissed before. Tons of times. With kisses just as innocent as this one. This one, however, THIS ONE carried something else with it. A silent admission.

Realizing we were the only two not dancing, we left the floor together and returned to our seats. Seats on the far corner from where we stopped dancing.

No sooner had we sat down, the dance/hip-hop/techno music started up again. We looked at each other in silence for a moment. It wasn’t a awkward silence, it was one of those “what the fuck happened” moments.

Within five minutes, we were laughing and playing like the kiss never happened. Or that it did, just that the meaning behind it didn’t matter.

I couldn’t help myself.

I was hot.

Sweaty.

Dancing with an attractive man who had a horse cock.

What woman’s libido isn’t going to be shook up after that?

Add copious amounts of alcohol, even if most of it had been danced off over the course of hours, and it is a dangerous mix.

Whether on purpose of mistake, I was now a slave to my own lust.

“William, I want to kiss you.”

He seemed puzzled, as if he did not understand the request.

“Seriously,” I drew in my bottom lip, “I want to kiss you.”

“Ok.” he joked, the realization of what I wanted to do was slowly beginning to kick in.

“I mean like you’re a guy.” I winced as I said it. I couldn’t believe I just said it.

William chuckled, quite confidently, “I can assure you that I am a guy.” escort menderes He looked at me with curiosity before his mood changed. It became…. intense. His brown eyes seemed to narrow and focus.

On me.

I felt warm. As if something dirty had just happened.

I reached across the table and placed a hand between his legs, a vain attempt to touch his cock, “I know you’re a guy”, I felt my breath catch in my throat, “I am very aware that you are a man.”

“You don’t say?” he teased, widening his legs to allow me access to what I sought, the fucker was teasing me!

“I do.” I nodded. I felt the warmth of his crotch, the sudden stretching of fabric as I struggled to reach just one…more…inch….

He chuckled, quite amused at himself. Or the situation we were staring directly into now, I wasn’t sure. “I have to say,” he paused, the dramatic type, “I am well aware that you are a woman, Angelica.”

“Am I now?” I pursed my lips, the response coming from my lips like a whistle.

“Not just now,” He intently narrowed his eyes at me, “I’ve always been aware.”

Oh God, I remember thinking: I want to fuck him in the worse possible way. It had been a while since I had sex, four months, which for me is a lifetime. I needed that familiar release now in the worst and most incredulous way. The urge was too much to contain anymore. All that dancing, grinding, bumping, intimacy, and teasing was too much to resist. Especially with an available cock right in front of me…

“How about that kiss?” He was continuing to egg me on, “Show me that you are a woman.”

He watched me push my chair back, rise to my feet, walk around the table, and looked surprised when I leaned over to kiss him. Abruptly, he shoved his chair back and pulled me down onto his lap. My spine tingled as I felt his strong hands splayed across my back and traced the outline of it down to my hips.

“I want you, William.” I admitted, kissing his neck, “I want to have sex with you.”

A blatant admission. I have to admit, I hadn’t thought about the repercussions of a sexual interlude between us. Could we keep it simple? Sure we could, I assured myself.

Fuck it, I thought. I need this. I need to sate my desire.

“We should do this my way,” he said wryly against my lips, “because I have lots of ideas for what we can do with each other.”

“You may speak the truth.” I spoke partially above a whisper before kissing his lips again.

I leaned in close to William and bit the fleshy and warm bottom of his ear before whispering against his neck, “However, I think you will find that doing this my way is going to be way more fun my way.”

To emphasize my point I shifted my bottom against his erection, innocently at first, before I noticed my “wiggle” had much more of an impact than I had anticipated which was quite advantageous for me. I could feel the pulse of his erection through his clothing and I murmured my delight to him as he sucked in a deep breath and held it for a moment before releasing it slow and measured, a vain attempt at maintaining some decorum of control.

With an enchantingly, wicked smile, I moved against him once more in a very slow and leisurely seesaw manner. This time, the effect was two-fold and served to spike my senses as well as his with Flash-like speed. I could not help but laugh to myself at the delirium I imagined us to be entwined in soon. The thought of his cock deep inside me made my clit throb.

William took possession of my hips, fingers splayed and exerted pressure downward, holding me firm against his straining cock. His dark, brown eyes closed for a long second before reopening consumed with fire and determination. I can’t exactly explain what that “look” is on a lover’s face but it is one of “the looks” that make me ready to fuck my lover until the last ounce of energy is gone from their body.

I had to kiss him at that moment. My will became exerted over his in the next. There was a certain urgency within my body that was itching to come out. That impatience, for lack of a better word, gave a power to the kiss that might have otherwise been lacking. I wanted to ransack and ravage this man; I didn’t want a taste and I certainly did not to sample his “goods”. I wanted a full-on gluttonous preview of what was to come this evening.

He tried to pull away. William tried to take control but I was not having it this night. I gripped his face, “No. If you do not play by my rules, then you shall not have me.”

In reality, he could have easily broken free from me. He was a lot larger than me. Stronger, too. Both facts were clearly known, hell, Stevie Wonder probably could have guessed this man could have turned the tables on me quite easily. Instead, William conceded to my order.

He was mine.

William did curl one hand around the back of my neck and ensured that our bodies did not part. His kisses were less forceful, his tongue exploring me in a grazing rhythm in tune menderes escort bayan with the pace and lead I had established. His free hand came to drift slowly down my back, sliding upward for a moment, as his fingertip came to rest on the plump outer curve of my cloth-covered breast.

The feel of his fingertips sinking gently against the fabric of my maxi dress ignited a deeper fire within my belly. My breathing changed instantly at that moment. I was very much aware of how vulnerable I was presently and the control I possessed, however imaginary, made my stomach ache for more of his touch.

Perhaps it was gratification but he chose to inhale my increasingly erratic breaths and drew me closer. A solitary moment later found my body arching upward to him, allowing premier access to the body part that he was massaging. He kissed the taut tip of my nipple through the maxi dress before waving his hand over it. Slowly his index finger pressed against my nipple. My instinctive response, of course, was to give more of myself to him by pressing into his hand.

I felt the flex of his hips as he thrusted upward, ramming his cock against my bottom. I giggled softly and my head flew back in response to the sensations I felt. His hands clamped hard onto my hips and exerted a rough downward motion. His cock literally pressed against the lips of my pussy. I found myself needing more than this feeble foreplay. He must have felt the same way because we both groaned at the pleasure building up within us.

I was no longer in a mood to wait. The urge to take him was quickly becoming a necessity.

“I’m done.” I murmured against the side of his head, pushing him away as I spoke the words.

I could almost hear the skipping of his heartbeat as he saw me pull away. The next moment his eyes widened as I reached for the zipper on his slacks. “I am done kissing.” I bluntly stated.

The zipper was down and I stood up.

Reaching for my nearby purse, I reached inside and fiddled for a moment before withdrawing a foil wrapped object. I held it up and with my teeth ripped it open and placed it upon his considerably more than generous cock.

A momentary thought about kicking off my sandals was pushed away. William had given thought about rising to his feet and fucking me against the wall. I saw it in his eyes. I sensed it in his movements. I wasn’t having it.

Placing my hands on either shoulders, I leaned against him and kissed his lips. It was soft and tender, with lips parting before our tongues danced against one another. I couldn’t wait much longer, my entire body was on edge. I was eager for his sex to be inside of me. I had to stifle my excitement as I straddled him, already imagining that magnificent cock deep inside of me. His hands lifted up to my sides and led me in, helping to raise the hem for our ascent to ecstasy.

William adjusted my position only slightly in order to bring the crest of his cock against the wet, throbbing lips of my pussy. With determination, he gripped my hips while our teeth gritted in pleasure as my flesh parted for him.

The world around us was muted and solitary in the next few moments. The silence, in reality nonexistent, was mentally manufactured by me as I began to take the full sensual force of what William was giving to me. That impact—with slick, electrifying friction as our bodies merged— caused me to yield to the desirable, the wanted, the needed, and the incredible sexualized invasion I was enduring. I felt a combination of pain and frantic pleasure wash over me as I came to rest completely on his cock. I felt it’s head pressing against the walls of my stomach.

I could hardly breath as I adapted to the careful yet raw burrowing of William’s massive cock inside of me. He took advantage of my momentary loss of perceived control and slipped his hands under my bottom. He took deliberate care to slide me back up his cock with a leisured and controlled ascent; no doubt to prolong the writhing sensations of having his eleven inches of sinful delight inside of me.

It worked.

I felt every soul-shattering degree of friction he provoked within me. I couldn’t help myself but to cry out in joyous delight as he completed one single thrust. It may have been too much for Samantha from Sex and the City, but a cock this size was more than pleasurable, it was downright fucking incredible.

My hips trembled in response to the second thrust of downward motion. My fingertips clutched at his shoulders as I felt him brush against my clit as my flesh gave way to him. I panted bit my lip, cursing at him in thought only, as I feverishly demanded more of his offering to me.

He must have sensed my distress because he obliged. We began to pick up speed and tempo, but each thrust was full and complete. I could sense his own impending climatic rush, but it was irrelevant to me. Despite his own condition, he lifted me up again so that we could both feel the lust-filled rapture that had made us victims of our own desire.

God, it was glorious. Every inch of my body hummed. I was awake and hungry. At the next depth of my descent, I arched away from him. Arms flailed behind me and my head fell back. Blood rushed to my head, providing me a vertigo-like rush of warmth, as my nerve endings elsewhere began to tense.

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