Where it happened: Home & School
Langauge: English
Sex: Male
Rating: 7
Category: Straight
There are two times I lost my virginity. The first time with a man, and the first time with a woman (in that order). It turns out I’m straight, so they really seem quite different events in my mind, with the latter making a much bigger impression.
First time with a man: It was John, my childhood friend, who it turns out is gay. We admitted to each other one night that we masturbated. The experience was revelatory — a huge weight off, and very arousing. After jacking off in front of each other for a few minutes, conversation turned after a few minutes to something like this:
“We should have sex! That would probably feel great.”
“Good idea. What do we do?”
“I think we…” John gets on the bed and sticks his naked butt in the air.
“Oh.” I try to put my penis in him from behind, but his anal sphincter is way too tight, we had no lube other than saliva, and neither of us had ever had anything travel antiperistaltically in the alimentary canal — an occasion that generally requires some amount of preparation. After failing miserably and finding myself shaking uncontrollably from the sheer speed with which the conversation turned into my trying to stick my dick in his ass, I came up with a neat solution.
“Why don’t you suck my dick?”
“Why don’t I try to fuck *you*?”
“Errrr, no.”
“Come on, why not?”
“I don’t know. Just let me blow you.”
“Ok. But then you have to blow me.”
“Sure, whatever.” It was unspectacular. I came. Then the dreaded moment came. What had I agreed to? At least his penis hadn’t recently been in my rectum. It was unspectacular. He came. John pestered me for the remainder of our (long-lived) friendship to let him have sex with me, but I was never interested, even when he offered me $500. We did regularly give each other hand and blow jobs and even played with some restraints.
The first time with a woman: Marta had slept with multiple boys in the frat house I lived in my freshman year at college. Everyone knew it. She was cute, though, so at most a deadleg was in order for sleeping with her. And, of course, the day arrived when I found myself naked in the oft-abused basement hot tub with Marta.
“You’re a virgin, for real?”
“Yep. Never even seen a pussy up close.”
“No shit. Here…” She spread her legs and arched her back so her pelvis was out of the water and her vagina was inches from my face. Her vulva looked exactly like I knew it would, having been an avid consumer of porn. A bit of a disappointment, in fact. But I was hard, so we ended up in my room.
She was very easy to penetrate, and it felt good. But not as good as I had hoped. This was certainly a superior experience in multiple ways, but just in terms of sheer stimulation, it was surprisingly inferior to my own hand. Alcohol, nerves, and a thin layer of latex. I was so jittery and strangely detached, like I was performing an act I knew well, that I did not come for half an hour. We tried all the standard positions, I think mostly because Marta got a kick out of my neophytism.
“Umm, this is a little embarrassing, but I don’t think I can come. Too nervous.”
“That’s okay.”
Marta showed up at my door a few days later.
“Want to have sex again?”
I closed down whatever I was doing on my computer, took my clothes off, and got in bed with her.
“Would you spank my ass?”
“Um, what? I mean, I’m not sure… uh… are you going to count or something?”
“Yes, master. Do you want me to count in English or Spanish?”
“Uh-huh. You speak Spanish?”
“Yeah, I’m half Cuban. Uno…” Thwap. “Dos…” Thwap. I lost my erection. She sucked me back to hardness, whereupon I got on top of her and ejaculated immediately. While my eyes were still closed from orgasm, my phone rang.
“I should get that.”
“Sure.” Plop.
It was Matt, a high school friend I hadn’t talked to in a while. I put my hand over the microphone. “Sorry — I have to take this.” She got dressed and left unceremoniously. As she walked by me, I realized that something about my behavior just then was rude, although I couldn’t put my finger on it. I put my hand over the mic again for a moment.
“Uh, thanks.”
That was the last time I slept with her.
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