#258) Matching Fantasies

This blog has REALLY helped me process some stuff from my past! As I posted in #218 “Cinco De Mayo Latinx”, I finally feel ready to move on and start dating again. Part of the reason for this closure is that I ran into my former lover and didn’t fall apart afterward. We had a civil discussion, laughed a little together, and kissed one another on the cheek good-bye. This chance encounter with Kyle made me reminisce about something he told me once.
It was early in our relationship. We’d just made love, and were now sharing pillow-talk, one of my favorite things to do in this world. I’d shared with him that he was the oldest man I’d ever “been with” and shared that total number of men.
“How about you, how many women have you slept with?” I asked.
“I’ll tell you, but you won’t like the answer…”
I was nonplussed. Was it thousands, like Wilt Chamberlain? Nervously, I pressed Kyle on it. “How many?”
Kyle cuddled close to me, which I loved; it nonverbally said that he didn’t want this to be a division between us. Then he said, “I don’t honestly know. It’s in the hundreds. Hell, my first time was with six women at once…”
I sat up in the bed a little straighter and tried to digest what he’d said. I decided to parse his statement.
“You lost your virginity to six women at one time?”
“Well, not technically. I mean, I climaxed inside just one of the women for the first time, but, yes, I was with six women at the time…”
“That sounds like a great story,” I responded honestly. “Spill the tea…”
He launched into the fascinating tale, “I was in college, dating a girl, Eileen, but getting nowhere with her. I invited her to a concert. She said that she didn’t know if she was free and would get back to me. Later, she called to say that she was busy that night, but that some girlfriends on her dorm floor were interested in going. Could I buy tickets for them all together and they’d reimburse me. I agreed, bought the tickets to our university basketball stadium where the concert was being held, gave them to Eileen and she gave me more than the total I’d spent. I’d made a profit, so I felt great. Then the night of the concert, I met these six girls at our seats.”
He set the scene, “I was a dude with hair down past my shoulders, wearing skintight bellbottoms and boots. The girls were all Jewish, all close friends, two were sisters. They were not glamour queens, but were all attractive, lots of long, wavy hair, lots of giggled, “Oye!” reactions when they saw me, several large noses and several that were so small, they were clearly the work of plastic surgeons. They were fun, easy-going, post-hippie chicks. During intermission, we walked around the concourse of the stadium and different girls would take turns to hold my hand. One of them produced a joint and we all smoked it. It was sweet, and at the end of the concert, I told them that. One girl, Suzie, said that they’d been talking, didn’t want the evening to end there. They invited me back to their dorm, right down the hall from where Eileen lived! I go, and as soon as we’re behind closed doors, clothes start coming off, and I’m surrounded by naked women, bouncing boobies, lovely bottoms, hairy pubic bushes, smiling, stoned faces…”
As Kyle reminisced and recounted this story, he started to get another erection. He was a man of near sixty, who had just fucked me silly a few minutes before. He also never took a performance enhancing pill in the entire time I knew him. My respect grew for this virile man-child, even more than the high esteem I already held him in. I spat on my palm, and along with my juices that were still on his cock, languidly jacked him while he continued the retelling.
“They had me lay face up on my back on a bed and took turns. They put a fresh condom on me with each new partner. It became kind of a game. I did not have intercourse with all six. The girl I was most attracted to, one of the sisters, just kissed me passionately the whole time, while I fondled her. As you now know, I last a long time, and they thought that was great. After a long time of fucking, Suzie said, “I’ve been watching, and Kyle likes butts, he’s always watching each of us as we walk away from him!” So she mounted me, but faced the other way around, what we now call reverse cowgirl. She was right; I did like looking at their asses, liked looking at hers flex as she rode me, and I finally climaxed, to a lot of applause and cheering…”
With a very brief refractory period, the dear old guy’s manhood was fully erect. I kissed the knob.
“That’s quite a story! Is it all true?”
Kyle put his right hand in the air as if swearing and replied, “Hand to God.”
I swung my leg over him and mounted him, sinking down on his delicious cock slowly.
“If you had to guess, would you estimate you’ve been with closer to two hundred women or eight hundred?”
He gestured with a thumbs-up for the higher figure. I rode him languidly, it was a lazy, lascivious, lovely fuck. Utilizing my old gymnast’s training, I lifted a leg and spun around on his cock to face backward, to give him a good look at my ass.
“I find it interesting,” I said while enjoying the ride, “that you didn’t lose your virginity until you were in college…”
“A combination of strict religious upbringing and being discerning,” he replied. I could say the same about my identical circumstances.
“I’m not jealous. I’m not threatened that you’ve known so many women,” I said truthfully. “I hope I rate near the top in terms of memorable quality…”
He sagely responded, “I never spanked any of those six girls. I continued to see Suzie for a little while after that, but never disciplined her once. I’ve spanked you repeatedly in the short time I’ve known you, Jeanie. And every time has been pure fireworks! You are right up there at the top…” and he started to buck his hips and swat my bottom. Talking became impossible. But I couldn’t shut off my mind. Kyle was a life-long learner. He was independently wealthy, so could indulge any of his many tastes. He lived his life to the fullest, then and now. I wanted to share life with him. I shared two years of fun with Kyle, which, looking back on it, was a good run.
Lord knows I’m not wealthy. But I hope to have an orgy similar to the one Kyle described sometime in my life. When I saw the above featured photo, this hope sprang to full bloom in my fertile imagination. I think it’d be euphorically liberating to fuck someone in another’s presence. I’d love to realize that potent fantasy of naughty schoolgirls being brought to me, their headmistress. I’d spank them one after the other, then harness into a strap-on and fuck one after another, while all the others watched and masturbated, then fuck each up six different, tight, virginal anuses, while all the others watched and finger-fucked their own rosebuds. I suppose that I ought to feel guilty for harboring such a nasty dream, but I don’t in the least. I’d like to prove to the world that you don’t have to be fabulously rich to get all the juice out of life.

6 responses to “#258) Matching Fantasies”

  1. I learned it the other way around.
    I was once rich. Very rich. I could afford to do what I wanted. Once, I let 6 girls beat me, they beat me, humiliated me, humiliated me and urinated on me. All 6 of them fucked me with their strapons. It sounds horrible, but it was a liberating experience.

    Liked by 2 people

    • I have never peed on another, or been peed on, but I’m intrigued by it. I wouldn’t want it in the face, but while in the shower, I could see getting on my knees and letting a lover bathe me in their warmth… But group sex is something I’m definite about.

      Liked by 2 people

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