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I’ve been on the business end of my share of cocks, from short skinny little rascals that barely tickled, through average sized that served quite adequately, to a few beefy rams that were painful and threatened to split me in half. Truly, size does matter. But several factors other than cock size matter just as much for sex to be considered phenomenal. Once I experienced a synergistic event that was so phenomenal I’ll never forget it.

In the summer of 2010 I met Jon, an architect who had come to Philadelphia to resolve some problems with a project his California firm had designed. Like me, Jon was bisexual, and after several dates we became intimate. Sometimes I joined him in his hotel room, and sometimes he would come to my house. Because I’m a total bottom, our usual routine consisted of me sucking his cock while masturbating. Occasionally Jon felt like sucking cock and we played 69. Every time I took his cock in my mouth I longed to get it in me.

That subject was broached one night at my place. I cooked linguine with Bolognese sauce served with a green salad and garlic bread. I poured Chianti and we finished the bottle with the meal. After dinner we drank beer in the living room and traded stories of sexual experiences. Jon talked about some of the wild women he had dated. The way he bragged about his conquests, it was obvious that he enjoyed having sex with women. “I like penetration,” he said, giving me a little buzz. “But what about you? What turns you on?” I decided to be truthful to see where it led. “I like penetration too, especially when I’m the penetratee,” I said.

“Really?” said Jon. “You never told me.”

“I didn’t want to push it. I hoped you might bring it up, or maybe it would just happen.”

He laughed. “Well, we’ll have to make it happen.” My heart went into double time. “Not tonight, though. It’s late and I have to be up early tomorrow. Next time.”

I was surprised and disappointed. In bed alone after we said goodnight, my mind raced with thoughts and images of Jon fucking me. I couldn’t fall asleep. I thought of Jean, the woman who introduced me to anal and remembered the first time. I had given her two or three clitoral climaxes with my tongue (I love eating pussy, too) and had a raging hard on. I was about to mount her when she said, “Do you want to fuck me in my ass, honey?”

It was an easy decision. I was forty years old and had never used the back door. I was curious about it, but before Jean, I hadn’t been with a woman who did anal. As it turned out, she really loved getting fucked in the ass. With vaginal sex, she moaned and panted. But on hands and knees with my cock in her ass she went demonic, grunting and snorting like a rutting pig, grinding her ass against me and coming nearly nonstop. Freud postulated penis envy. After years of fucking one wife and several girlfriends, watching their multiple mind-blowing orgasms, I guess I developed a mild case of vagina envy. Exposed to Jean’s anal frenzies made me intensely curious and eventually led to experiments with my own ass. I thought if a woman could get such anal pleasure maybe I could too.

There’s a taboo that says the asshole is dirty, don’t touch it. I never paid much attention to mine, other than eliminating and keeping it clean. My exploration started small. I began by inserting a finger in my ass when jerking off. That boosted the intensity of my orgasms, so I tried bigger objects. With increased size came the pleasure of fullness. I felt a little perverted initially, but I was alone, it felt great, and it was my dirty secret. After months of inserting anything around the house that looked even faintly phallic, I ventured out to an adult toy store and bought a vibrating silicone dildo.

From the look the sleazy guy behind the counter gave me as he handed me my change I imagined he was thinking I know you’re a faggot and you’re going to stick that phony dick in your asshole. He would have been right about the last part. Taking that baby to bed with a tube of AstroGlide I was as excited as a virgin about to get laid. I’m afraid my greedy eyes had been bigger than my asshole when I picked that toy. It required numerous sessions of painful, persistent stretching to get it all the way in. I knew my patient perseverance had been worth the effort when I had the first anal orgasm. I was slowly thrusting with the vibe cranked to the max when suddenly my body convulsed in spasms of euphoric pleasure so intense I had to pull out to stop them! I wondered aloud, “My God! Is that what women feel?” I was hooked on anal.

When Jon left that night he gave no indication when I would see him again. I didn’t want to call him, didn’t want to reveal how anxious I was, so I just waited. When he called I picked up the phone breathless. “I’ve been thinking about you,” he said. “Can I come over Friday night?”

“Of course you can come,” I replied. In me, I hope.

“I’ll be there about 7:30. I hope you’ll be ready,” he said. I couldn’t bring myself to ask, ready for what? It was the first time I heard a hint of dominance in his tone. It encouraged me to believe that I wouldn’t be disappointed.

All day Friday I endured an agonizing anticipation. I kept hearing the words, “I hope you’ll be ready.” I would. As soon as I got home from work I took douched and showered. Because I wanted to be absolutely ready, I put on a T-shirt that barely covered my ass. I planned to welcome Jon in my most accessible outfit. I would have preferred something feminine and naughty, but I’m not into cross dressing. I figure a man should accept that he’s having sex with another man, and not play make-believe. I was too anxious to eat, so I poured a glass of wine and sat in the kitchen watching the minutes pass on the microwave clock. At 7:10 I went upstairs to lube and stretch my ass with my biggest dildo. I was ready.

Jon arrived at 7:35, smiling like a mischievous schoolboy. “I love your outfit,” he said, “Bottomless.” He spun me around like a dance partner and slapped my ass. “I see you’re ready. But first I want a drink. Make me a margarita.”

“The take-charge attitude is new. I like,” I said. “Come on in the kitchen and I’ll make a pitcher. You want salt on the rim?” As I stood at the counter and prepared margaritas, I felt a dribble of lube between my thighs. It’s a great sensation. I like to think it’s probably like a wet pussy. Jon was talking about something that had happened at the job site, but I was too preoccupied with questions, such as, what position will he want me? Doggie or missionary? Will he want me to blow him first or will he plunge right in? Will he want to use a condom? I want to suck him hard first. That was the content of my sluttish mind as we talked and drank margaritas. Two apiece and it was off to the bedroom.

Jon undressed and lay on my bed. I was delighted to see that he was already getting hard. He closed his eyes and gasped when I touched his cock. Immediately it began swelling in my hand and was soon as hard and rigid as steel pipe. I stroked it, teased his balls with my fingertips, and he smiled.

“Can I-- ?” He responded before I could get the words out: “Do anything you want.”

I slid down the bed and wrapped my lips around the head of his cock. He gasped and moaned as I worked my mouth up and down the length of the shaft. I filled my lungs and let my breath out as I tried to take him in my throat. The head cleared the back of my tongue but his cock was more than I could swallow. I felt it swell. I feared he was going to come. I was hard too, my scrotum tight as a tennis ball. Jon pushed my head away.

“What’s wrong?” I said.

“Nothing’s wrong. I’m going to suck you,” he said.

“Gently, go easy. I’m almost ready to come.”

He crouched next to me and began to gently tease my cock with his lips and tongue. Then he pushed apart my thighs and rubbed my anus. As it relaxed he inserted a finger, then another. My sphincter was as yielding as a ripe peach. “Are you going to fuck me now?” I said.

“Absolutely.”

I rolled onto my stomach and raised my ass. He immediately climbed aboard and started nudging his cock between my cheeks. I reached around with both hands and spread my ass. My heart was exploding in my chest and I was gasping for air. My whole body ached with desire. Suddenly he was inside me, and I raised my ass more to get his cock deeper. He started thrusting, slowly at first and gradually quickened the pace. I joined him, meeting his thrusts, and he was all the way in me. I heard Jon’s moans and blending with hoarse gasps and was shocked to recognize my own voice. His cock felt enormous. My whole body stiffened in an anal orgasm and as my ass muscles clenched his cock he drove it all the way in and came. Feeling the spasms as his cock pumped hot cum into me I began coming too, rising in ever more powerful waves of pleasure until a final spasm engulfed me so intensely I wanted it to end.

Later, as we rested, I slowly came down from that total body tingle that follows great sex. I thought about how the right meteorological conditions can come together simultaneously to produce what’s called a “perfect storm,” an event of unusual magnitude. Of course, a perfect storm is a devastating event, not at all what had just happened. I realized that several factors had combined tonight—the excitement of the first time with Jon, the length and girth of his cock, my ass muscles supple and yielding, just the right amount of lubrication, and the united energy we expended—joined together to produce as perfect a sexual experience as I was able to conceive. I fell asleep and dreamed an old woman with long gray hair took my hand and led me through a dark urban landscape.

We continued to have sex once or twice a week until Jon’s assignment ended and he returned to California. Every time I took his cock in my mouth, I longed to get it in me, to ride it until we both came. When I knew we would be together, I rinsed and lubed, just in case. We fucked several more times, and every time was good, but we never again achieved the near perfection of the first.

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4 years ago
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Mary Ellens Marriage

During the past three months my wife had fucked over fifty different men and it is all my fault. I've watched her do most of them, but on several occasions she has gone out on a "date" and not come home for two or three days, during which time I sit at home, play with my dick and wonder what she is doing and with how many. I have only myself to blame because it is because of me that she's doing it. It all started because my dick was sore. Mary Ellen and I have been married for a little...

3 years ago
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Boys Will Play While the Wifes Away Part 2

This Part has plenty of action but for best results I suggest you read Part 1 first. My drive home from the mall flew by in an instant. I had only gone there to buy make-up and ended up with a bag full of cosmetics, panties, blouse and a skirt – not to mention being sucked off in the changing rooms by the cute Asian salesman, Philip. It’s still hard to imagine that I had spent 36 years of my life without experiencing the touch of another man. My legs were still like jelly as I rushed into...

Gay Male
2 years ago
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The Transformation Spellchecked version

We were the team of 8 people who started from Kenya. Everything was alright until that day... I had gone to Nairobi to buy some liqueur as there were only few bottles left. The capital was some 400 miles from our camp. I came back in the evening only to find the nest empty.i searched everywhere but got nothing. There was no trace of any human being. There was a very queer atmosphere. Something was very strange. I rushed to our site.. As I reached there, I found the body's of my mates. I...

2 years ago
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ProeliatorChapter 3

It didn't' take too long to get back to camp. To keep myself safe and to hone my skills, I monitored the area to see if I would be attacked. When I came near the camp I called loudly, "Do I have permission to enter the camp?" In a few moments it was one of the Romans that told me to enter but he had his spear raised. He was one of the ones more antagonistic to me. I said, "Are you going to throw the spear at me when I have my knife sheathed?" "Where did you go?" "To make sure you...

3 years ago
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Horny Pregnant Mom

Introduction: Husbands gone, time to play… Monica was 8 months pregnant. Her husband Greg was an over-the-road truck driver and was usually gone 6 days a week. Monicas hormones were in overdrive. She was so horny, and she really needed to get laid. So, the day she watched her son Jeff as he climbed out of the shower didnt help her much. It was an accident. She had been doing the laundry and was taking a load of clean towels to the bathroom. As she entered the bathroom, her son Jeff had just...

4 years ago
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Curious No More

I began dressing in my sister's clothes. I would get so hard and excited when I felt the soft panties against my cock and the bra wrapped tightly around me. But my dress up time was always short. Now that I live on my own I have my own femme wardrobe and plenty of time to dress and perfect my makeup and appearance. The more I dressed and the longer I stayed dressed, the more I wondered what it would be like to be held closely by a man and feel his warm embrace. Soon I began to wonder what it...

Crossdressing
3 years ago
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Catch 22 WifeChapter 6

The dancing and the short but stressful conversations on the couch had drained me and I fell to sleep quickly despite the uncomfortable couch. The lack of a comfortable mattress meant that I had an uneasy sleep, and when one of the ladies decided to sneak out of the bedroom later, her attempt to be quiet brought me back to wakefulness, although I turned my body so that my face was buried in a pillow, trying to appear asleep. The lady came out to stand just near the couch, and for a moment I...

3 years ago
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Three Days

"Don't forget your promise," she told me. "When I turn 18, I'm moving out too, and I'm coming straight to your place." "My casa is your casa or whatever." Of course, I had forgotten all about that. I hadn't seen her or my mother since then, just talked on the phone. And I'd been joking with her. But my sister wasn't on my mind that night. I had called her earlier in the day and left a message wishing her a happy 18th birthday. I had also sent her a card with 100 dollars in...

4 years ago
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Charladys Bout of Sexual Roulette

After Charlady's last epic adventure, (Charlady's Jamboree), Master Ray revamped the play room, he had a specially made table built to his own design. This Table was six feet six, circular in size and shape and with a standard double mattress would adequately stand in as a double bed although a little quirky in its design. When I explain you will see why, for the whole table top was designed to rotate about a central axis. Further features we also incorporated like slots fro wrist and ankle...

4 years ago
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Youth Training CenterChapter 7

Jim Neilson was led into a small room in the center of which stood an odd looking chair. Not recognizing the device as the close relative of a birthing chair, Neilson circled it, staring at it curiously. The plastic, anatomically shaped seat stood at about the same height as a barber's chair and had controls that would allow it to be raised or lowered to any height. The seat back could also be raised or lowered allowing the person seated in the chair to be sat up straight or leaned back into...

2 years ago
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The ProdigalFiftysix

BEFORE WE GOT STARTED on the task of packing Sunday morning, we had to take care of Melody’s cramps. Her period was a day away and would make her useless for carrying things around. The cure seemed to work for several hours, and we could get work done between treatments in the tub. She made packing boxes a little more enjoyable. Our cars were parked in the drive and on the street to make room for boxes in the garage. Each box was labeled with what room it would be moved to in the new house....

3 years ago
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Powerball

Barry and Jill Thomas lived in a small town in Northern Tasmania having a population of around 5,000 and they had known each other since primary school, in fact both attending that and the area's High School together right through. Barry was a well built 180 centimetre tall tractor driver working for a ploughing contractor, and Jill was a curvy girl of average height and nice appearance, who, due to the size of her breasts had sometimes had her described as "dairy fed." She was pretty but...

4 years ago
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Fiftieth High School Reunion

Fiftieth High School Reunion When I received my Fiftieth High School Reunion packet I almost shredded it along with the other junk mail. I went to my tenth reunion and never went back. I realized that I didn’t like anyone that I had attended school with, I was the youngest member of my class, and I was a nerd. I didn’t know I was a nerd. Not until I saw the movie called Revenge of the Nerds. That was when my wife and finally realized that I was a nerd. I had been sixteen throughout...

1 year ago
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HandsOnHardcore Susy Gala A Manager8217s Advantage Fucking The Secretary Under The Sun

Manager Alberto Bianco is a lucky guy. He makes a lot of money, lives in an awesome mansion with swimming pool, and gets a chance to fuck his secretary Susy Gala whenever he wants to! What a life. Sit back, and see for yourself… The busty brunette hot babe with brown eyes walks up to her boss and seduces him by grabbing him by the balls. The tattooed glamour porn star from Spain is so hot, Alberto’s dick get hard the moment he sees her. She takes off her bra and wraps her massive...

xmoviesforyou
3 years ago
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The Life of RyanChapter 29 Warming up to Kristen

Kerri and Jenna had taken a day off together to go shopping. They had more money than each of them had ever had before, and hit some high-end clothing, shoes and lingerie stores, loving the spending power they now had. They figured that planning ahead for the upcoming 3-week cruise vacation involved lots of shopping. They returned around 7:30, toting about a dozen bags each, and walked into the main living room where a movie was playing on the big screen TV ... and where Ryan was casually...

4 years ago
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Runs in the Family Part 3

It was astonishing how quickly a life of thirty years could fall apart. One single night, one simple mistake, one marriage dissolved. Bianca had her taste of Bruce, and she was satisfied. Or so she thought. But sleeping with Vince when he returned from his trip become a chore, where she counted down the minutes until he finished. Then she was imagining her son-in-law again, seeking some solitary pleasure while her husband slumbered beside her.When she came up pregnant, Vince was furious. And...

Cuckold
2 years ago
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Collateral Ch 5

Chapter FiveJake was getting restless. There was no TV or other means of entertainment he could use while waiting for that annoying bastard. He had a mind to just get out of the house, but he didn’t want Klaus to chase him down from the first day. There was enough time to observe his surroundings later. For now, he had to admit he was very curious about this insanely rich guy, at least by his standards, and his unusual interest in someone like him.The door finally opened, Klaus coming in with a...

2 years ago
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The Witches of Fairmont High

Given all the recent controversy, I should mention that this story can be posted or archived without further permission from me. I write for my own enjoyment and for the enjoyment of others - not for money, fame, or anything else I can think of. With that in mind, please enjoy. And, oh, by the way, this story is pretty PG (maybe PG13). No steamy sex scenes or the like. Still the them is essentially adult and TG, so if you don't like this sort of stuff, don't read it. Again,...

3 years ago
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Babysitting Sis

He went looking through the house, checking her room and the bathrooms, the den and family rooms only to find them all empty. As he was approaching the sliding doors he heard a splash and realized that she was in the pool. He opened the door and yelled again for her to come eat, turning away as he did to head back to the kitchen. She followed him in a minute later, clad in a bikini that left little of her young body concealed. The pale blue cloth stretched over her already somewhat developed...

4 years ago
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Taking the Long Shot Ch 0102

Copyright© 2008 by Denham Forrest (The Wanderer) * Although there is some mention of violence, murder and even rape in this four chapter story. It is completely devoid of any intimate sex. Clarification:- DHS in the UK, historically stands for the Department Of Health and Social Services, that was charged – among other things – with handing out cash to the unemployed and the financially destitute. It’s now been abolished under the British government’s normal system of spending more cash...

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