I’ve been on the business end of several cocks, from short skinny little rascals that barely tickled, through the 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 was the beneficiary of 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 long to get it in me.
That subject was broached one night when he was at my place for dinner. I made pasta Bolognese 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 talked about some of our 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 being penetrated,” I said.
“Really?” said Jon. “You never told me.”
“I didn’t want to bring it up. I hoped 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, but 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. I recalled 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 repeatedly. Freud postulated penis envy. After years of fucking one wife and several girlfriends, watching their multiple mind-blowing orgasms, I guess I developed vagina envy. Exposed to Jean’s anal response also made me envious and eventually led to experimenting 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 elimination and keeping it clean. My exploration started on a small scale. 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 little 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. The guy behind took my money glared a look that said I know you’re a faggot and you’re going home 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.
Jon left without giving any indication when we would be together again. I didn’t want to call him, so I just waited. When he finally called several days later 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.
“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 an enema 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 form. My female side 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.”
“I like the take-charge attitude,” 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, probably not unlike 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 mind as we talked and drank margaritas. Finally we went 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 swallow. The head cleared my tongue but his cock was too thick to swallow. 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.”
“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 fresh dough. “Are you going to fuck me now?” I said.
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, joining his rhythm, and he was all the way in me. I heard Jon’s moans and someone’s hoarse sobs 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 all the ideal conditions can come together at the same time 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. It usually was blowing him and jerking myself off. 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. He fucked me several more times, and every time was good, but we never again achieved the near perfection of the first.