Emma and I recently celebrated the first anniversary of our first date.
She marked the occasion with a gift. She gave me a new wallet, something she determined that I very much needed. My previous wallet had been given to me as a souvenir of serving as a groomsman in my brother Frank’s wedding.
My brother Frank, whose eldest son now has a driver’s permit in his wallet.
“Oh, thanks, hon,” I said, kissing her cheek. “I’ll think of you every time I feel my ass.”
“You’re welcome. This is only the second time I’ve made it to a year with someone, so I thought it was worth commemorating. Now you can clean out that storage unit in your back pocket.”
“I hate to think of what I’ll find in there,” I agreed. “Anyway, thanks for this memento of our relationship.”
“We don’t have a ‘relationship,’” she shuddered. “We have sex.”
Yes, dear. Whatever you say.
It was a thoughtful surprise. I’m still hunting for a gift for her. I know what she wants, so you would think shopping would be a breeze.
Emma wants to see a man lose his ass virginity.
Early in our relationship . . . I mean, not long after we started having sex, I offered to try to arrange whatever sexual adventure Emma requested. She quickly produced a list.
I roped men to chairs for her to tease.
We flogged men. We flogged women.
We had sex in every room in my apartment.
We made pretzel knots of every threesome and group sex combination I could concoct. I was especially proud of the lezzie threesome I cooked up. Not every fella can do that for a gal.
One day, Emma pointed out that she had never seen me fuck a boy.
“No way,” I said. “I fuck boys all the time. How could you not have seen me fuck a boy at an orgy?”
“We are never in the same room at orgies, moron, that’s why.”
She had a point. At most orgies, she’s fucking her way through one crowd as I’m working another. In fact, we are each the person the other is least likely to fuck at an orgy.
I offered to rectify this oversight promptly. Feeling full of bourbon and bravado, I even upped the ante. I would fuck an ass virgin for her.
“That would impress me,” she nodded. “Thanks.”
“Be ready to be impressed,” I boasted. “He will go from wary virgin to noisy slut before your very eyes.”
She smiled. “You’re cute when you drink,” she said.
“When don’t I drink?” I asked.
I approached my task with plenty of enthusiasm. After all, this project would allow me to hunt down my favorite flavor of boy—straight but curious.
Now, I’ve got nothing against gay boys. I’ve pounded nelly bottoms until I was dizzy from the fog of their poppers.
Bisexual bend-over boys are my brethren. If you need your ass plowed while your wife watches, I’m your man.
Give me an experienced ass any time. I’ll remind that boy of every prison film he’s ever seen.
Even so, I have an abiding affection for straight boys who need to get fucked. One could almost describe it as a sentimental attachment.
After all, the first boy I fucked was Allan, my straight boyfriend in high school. The first fellow to take it on a regular basis was my straight roommate in college.
I understand straight boys who need to get fucked. I speak their language. They need to be reassured that this won’t make them gay, dude. It’s just something that feels awesome. And no, I’ll never tell anyone. Promise.
I also understand ass virgins. I show them what to expect. I talk about how the initial resistance is the most uncomfortable part, but once you get past that, it’s smooth sailing.
I make my dick seem nonthreatening. I offer sensuous foreplay when needed, direct action when preferred, and always, rivers of lube.
Deflowering a straight ass virgin is my kind of project.
The only problem is: where the heck do I find a straight ass virgin?
If I know a guy wants to get fucked, you best believe I’ve fucked him.
If I know he doesn’t want it, I’m not pressing the issue. There’s just too much ass out there that needs fucking; no sense beating your head against a brick wall.
Sometimes, you come so close. Two regulars at my orgies each found themselves in other situations where they decided, what the hey, today’s the day, and got their virgin holes plugged.
I gave them each bloody hell. Some nerve, I said, losing it to other men.
To satisfy this project for Emma, I would have to look outside my usual circle of friends. But you can’t just post on Craig’s List asking for a straight ass virgin. Any pig worth his salt would fake his first time in order to take a good stuffing.
Scouting for a straight ass virgin takes dedication. Cultivation. Care. And a powerful lure.
Emma’s eyes were my lure. With the promise of a naked girl in the room, you can get straight boys to do pretty much anything.
I put up carefully worded posts—none overtly mentioning anal sex—and responded to ads. I weeded through applicants, separating wheat from chaff, looking for the fellow who would get my dick hard and serve as eye candy for Emma.
Topping the list of potential bottoms was a twenty-year-old sophomore. He was straight, but he had a double major, so I figured he could look at life from both sides.
In the photos he sent, he looked very cute, with dark curly hair and sensuous lips.
He had already forged a good friendship with his ass. He enjoyed stuffing toys up there, though, he complained, he had few opportunities to do so in his dorm.
I explained my situation. I had a girl who wanted to watch me fuck an ass virgin. I preferred to meet with the guy first, one on one, to be sure he was a good person before I foisted him on her.
He thought that made sense.
I made a suggestion. Since you like to play with toys, and you need a place, why not stop over some time? We’ll try out your toys and get acquainted. Then, assuming it goes well, we’ll meet again for the cherry-popping ceremony.
He liked the idea. He wanted to come over immediately.
I was tempted. He was so attractive, and so turned on, that he had me pretty worked up.
Only, I had a date at eight. Not, as luck might have it, with Emma—who may have enjoyed a surprise present—but with Anna, my on again, off again girlfriend.
Most of my lovers would be cool with arriving to find me with a naked boy. In fact, many have.
Not Anna. She was entirely above board and not clued in about my life as a pervert. She knew I was bisexual, of course, but I wasn’t keen to offer the evidence.
Still, this boy was bursting with enthusiasm.
I checked my clock. It was just after six.
Okay, you can come over, I wrote. But only for a short time. I have to kick you out by seven thirty. I have a date coming over tonight.
He replied that he was on his way.
I left my computer and cleaned the kitchen. I chopped ingredients for the dinner I was preparing for Anna.
I made my bed.
I checked my email.
Six thirty passed. Six forty five. Seven.
I had second thoughts. This wasn’t going to work. The boy was taking too long to get to me.
I wrote him a note.
I don’t think we’ll have time for this tonight. I’m sorry. But I would like to meet sometime soon. I think you are very promising!
I took a shower.
Around seven fifteen, he phoned from the lobby. I was still toweling off. I rang him up. We could at least shake hands and reschedule.
I pulled on pants and a shirt just before he knocked. I opened the door.
God, was he cute.
He was over six feet tall, maybe six five, with clear skin and brown eyes that shyly avoided mine. He was carrying a backpack.
“Hey, thanks for letting me come over,” he said, setting down his backpack. “I’m sorry I’m so nervous; I’ve just never done this, meeting someone online and all.” He began to pull of his shirt. “So how do we work this? Do we just get naked, or should we talk first, or . . .”
‘Yeah, okay,” I said, pulling off my shirt. “Let’s get naked. But really, this can only be short. I have to kick you out soon.”
“No, that’s cool, that’s cool,” he said, unzipping his jeans. He stepped out of them, dropping them with his things on the floor. He fingered his boxer waistband for a moment, hesitating before rapidly pulling them down.
He stood naked. His long torso was slender and smooth. His cock was small, almost lost in a forest of dense black hair.
“So, now, what do we do? You want to do stuff in here, or . . . “
I unzipped. “No, actually, let’s go to my bedroom.” I pulled off my pants and led the way down the hall. He bent to retrieve his backpack and followed.
“Thanks for doing this,” he said. He put his backpack on the bed and opened it. “So, okay, I brought a few things. I’ve got this dildo,” he said, pulling out nine inches of silicon. “I’ve also got this thing,” he said, offering a series of balls connected at four-or-five-inch intervals along about two feet of cord. The balls got progressively larger. The last one was the size of my fist.
“You put that in your ass?” I said. I pretended not to notice my erection.
“Yeah, it takes time, though, which sucks with roommates and everything.”
“I can imagine. And we don’t really have much time now. So why don’t we try out the dildo?”
“Okay. Should I bend over the bed, or get on my knees, or . . . “ His voice trailed off.
“Why don’t you lay on your back and spread your legs?” I suggested, pulling lube from a drawer. “You’ve got a nice face and I want to look at you. Scoot to the edge of the bed.”
“Oh, thanks,” he said, settling back. “I don’t think I’m so hot, but people say that, so thanks. Do you think my legs are too hairy? I’m thinking of waxing them.”
“Your legs are fine. Now, spread them . . . actually, here, put your calves on my shoulders.”
“Like this?” He lifted his legs. I helped to settle them near my neck.
“Yeah, that’s great.” I warmed lube in my hand, and then massaged it on his hole. “So, how long have you been putting things up your butt?”
“I dunno, since I was a kid, I guess.”
“And you never put a dick in there?” My finger probed him. His cock grew hard.
“No, I never thought about it really, until now. I mean, I’m just not into guys, I guess.”
“Never even considered it?” A second finger joined my first inside him. He didn’t seem to notice.
I lubed the dildo with my free hand.
“Not really, Like, I know I’d never want to kiss a guy or suck him or anything.”
“Would you mind if a guy sucked you?” Three fingers. I touched his cock.
“Yeah, I guess that’s cool, but I’m not into it.” He put his arms behind his head. “I’ve got a gay friend, my best friend, really, and he’s asked. But I’m not into it.”
“Well, that happens,” I said, easing the dildo into him. “I mean, I know gay men who can’t stand to get their asses touched, and straight guys who like to get fucked. It’s sometimes as much about physiology as sexuality.”
“Yeah, like the prostate and all.”
“Right.” That reminded me to massage his prostate. He was unfazed as the nine inches went in and out of his ass.
I was out of conversation for now. He fell silent. We just focused on his ass.
Seven thirty five.
He was adorable. His face was so peaceful. I would have enjoyed toying with his hole all night.
I massaged his smooth, flat belly.
“So, you know how I want to fuck you in front of my friend? You’re cool with that?”
“Yeah,” he said quietly, his eyes closed. “It sounds hot.”
Oh, Emma, I thought. I’m so sorry for what I must now do.
“Well, actually, I’m gong to fuck you tonight. Now.” I took the dildo from his ass and placed it on the nightstand.
He opened his eyes. “Will she be mad about that?”
“She’ll be fine,” I said, pulling a condom from a drawer. “I think she’ll like to watch you anyway. You are very beautiful when you are getting your ass filled.”
“Thanks,” he said. “Just, you know, I’ve never done this, so . . . “
“I know, baby. I’ll be gentle. Don’t worry; if you can take those toys, you can take my cock.”
He watched as I rolled a condom on my shaft.
“Okay.” He lay back. “Let’s do this.”
“Great. I’m going to stand beside the bed. You just put your legs back on my shoulders . . . good. Now, I’m going to guide the head of my cock into you.”
I watched as the top of my cock went in. “You okay?”
He breathed out, nodding.
“Okay. Now, a little more . . . you okay?”
“Yeah, just . . . man.”
“You need me to stop?”
“No, no, keep going . . . “
“Okay. Here’s the rest of it.” I leaned forward. His knees tensed against my chest. "Okay, it’s all in you. How do you feel? All right?”
“Yeah, yeah.” He looked up, away from me. “It’s just different.”
“Different, but okay?”
“All right. Let’s just rest here and let you feel me inside you for a bit.” I stood, keeping my cock still in his body. His eyes looked around the room, as he tried to focus on anything other than the sensation within him.
Finally, he gave into it.
I pulled back a bit, then eased back into him. He took it well, so I continued. I gradually began to increase my pace.
“You enjoying this?” I asked.
“It’s just . . . it’s like nothing else . . . nothing else, man . . . I’ve never done this.” His eyes met mine, for just a moment. He had the look of epiphany.
“I know, baby.” I put a hand on his chest. “Now, I want to come closer to you so I can give you more. Are you okay with that?”
“Yeah, that’s cool.”
I eyeballed the clock. Seven forty seven.
I leaned over him, pressing our bodies lightly to one another. Resting my weight on my elbows, I began to move deeper into him.
“Fuck . . . wow, that’s so . . . I’ve never done this.”
“I know, baby, I know,” I whispered. I longed to kiss him, but you can’t kiss straight boys. They freak.
Instead, I began to pound him hard.
“Oh, yeah . . . yeah, that’s so . . . oh shit, man, I’m going to cum . . .”
I stood back to watch. His cock jutted into the air, throbbing up and down. Neither of us touched it.
It shot. It shot across his chest to his cheek, covering his belly, hitting the sheets over his head. He moaned and said something inaudible. I rubbed his legs and continued to fuck him, riding out his orgasm.
As it subsided, I fucked him more gently.
He looked at me.
“Mister, that was amazing,” I smiled.
“Yeah, man. Wow.” He fingered the cum on his cheek. “Did you see how much I shot?”
“I sure did. It’s like we pumped it out of you, but good.”
“Yeah, I guess.”
I eased out of his ass. “Okay, well, much as I hate to do it, we have to end this for now.”
He looked at me. “You don’t want to cum?”
“Not tonight, man. Next time.” I pulled the condom off my cock. He sat up.
“Oh, well, thanks,” he said. He scruffed his hair. “I guess I didn’t do it for you, but that’s cool . . . “
I leaned forward and took his cheeks in my hands. I brought my face level to his.
“You are a fucking gorgeous man and I am so turned on by fucking you, I could go all night. But I’ve got a date coming any minute and I need you gone.”
I stood. “Anyway, I have to fuck her, so I need to hold out.”
“Oh, that’s cool. Wow, okay,” he stood. “I should get dressed.”
“Let’s clean you up first.”
I took his hand and led him into the bathroom. I cleaned his body with a washcloth. I told him anytime he wanted to get fucked, or needed a place to play with his ass, he should drop me a line.
“Hey man, I will. That was really awesome. Awesome. I guess I can tell my gay friend we did this—now I guess I can let him fuck me too. I mean, I guess he knows I’m not gay, but this is just physiological, like you said.”
I held his cock in my palm as I gently washed it. “I bet he’d be glad to hear it,” I said.
He dressed, packed his backpack of sex toys, told me I was very cool, and left.
Seven fifty eight.
I ran to the shower.
Eight twenty six.
Anna arrived, late as usual.
The next day I sent a note to the boy, saying it was great to meet him and I looked forward to more.
A few days later, horny, I wrote to ask what he was up to.
A month later, I asked if he would like to meet again. I asked if he was still interested in being fucked as my friend watched.
I never heard from him.
I still owe Emma a gift.
But I tell you what: his gay friend fucking owes me a drink.