P is for Pegging (The Fantasy A-Z Series)
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Authors: The Pleasure Mechanics,Chris Maxwell Rose
P is for Pegging
Part of the Fantasy A-Z Series
By Chris Maxwell Rose
Copyright 2012 © Pleasure Mechanics, LLC
All Rights Reserved
Tonight is my three month anniversary with Laura. I have a romantic date planned, dinner and a concert at a little jazz club downtown. Then, hopefully, back to my place. Laura and I have great sex - at least, we’ve had great sex so far, and I can feel there is a ton of potential there. She is fit, enthusiastic and highly orgasmic. I love a woman who knows what she wants and asks for it. So I’m pretty excited for tonight but also kind of nervous. I’ve decided tonight is the night I want to tell her about some of what I really like in bed, and I am not sure how it will go over. She seems open minded enough, we’ve already played around with a little bit of spanking (on her) and bondage (on me) but from my experience the question I need to ask her tonight is one that has ended all too many of my relationships. I’m really hoping tonight is different - I really like Laura and even find myself wondering sometimes if she might be “the one” as they say.
Most of my girlfriends have reacted in the same way. They get confused, they get grossed out, they accuse me of being a closeted queer. It’s not that I don’t understand their initial reaction: I went through all of those same thoughts myself once upon a time. What pisses me off is the refusal to think past the initial disgust and hear me out. I’ve learned to bring up my desire for pegging early on into a relationship, to weed out the close minded women. It’s not that I need it every time I have sex, far from it. Once a month would be fantastic. What bugs me is if a woman is so turned off by one of my greatest sexual pleasures, I just don’t see much of a future together. Most of the women I’ve dated think it is perfectly fine to use vibrators for her own pleasure, but as soon as I want to bring one of my toys in bed, I get accused of everything from perversion to identity disorders. Screw that. I would rather be alone, pleasuring myself every night, than share a bed with a hypocrite.
Maybe I’m being too harsh. Forgive me. It’s just that after three years of dating, and three years of being rejected every time I ask for what I want, I feel a little beaten down.
I’ve been on enough internet forums to know I’m not the only guy into pegging. From what I read, it is actually gaining in popularity. I’m looking forward to the day when it is just another sex act on a big menu, when more guys will speak up about their enjoyment of their own damn asses so the rest of us don’t look so much like freaks. You know, it wasn’t too long ago when using a vibrator was pretty far out for women, and not too long before that when anything other than the missionary position was considered extreme. So I feel pretty confident that someday soon pegging will be considered normal and healthy. I want more guys to know about it - because trust me, it changes your sex life forever in all the best ways.
Deanna was the first to introduce me to my ass. Before her, I never even considered my ass to be part of my body, it was for one function only and that had nothing to do with sex. Deanna and I were together in college, she was a few years older than me. I don’t know what she saw in me, but I’m glad she said yes when I got up the balls to ask her out. She was far more sexually experienced than I and initiated me into all sorts of new illicit activities. But by far, her lasting gift to me was when she showed me how good a little anal play could feel for a guy.
I’ll never forget that first moment of contact. We were in my dorm room, and she was going down on me. She was masterful when it came to oral sex, pulling my entire shaft deep into her throat and working in a steady rhythm. I never knew it could get any better. She must have been in a mischievous mood that day, because her hands started to wander. She was talented with her hands, working my shaft, lightly tugging on my balls in just the right way, even pressing deep into my taint in this way that made my cock swell even harder. She had all of me in her mouth, and my eyes were closed, lost in the sensation of her wet lips working me over. I didn’t even know what she was doing when I started feeling fireworks up my spine, and before I could register her finger on my asshole I was coming harder than I ever had in my life.
When I came out of my post-orgasmic stupor, I asked her what the fuck she had done that had felt so good, and so new. She reported that she had just touched the outside of my ass, she hadn’t even gone inside. Smiling wickedly, she added “Want to experience something really wild? Let me go inside next time!” She was so casual about it, as if she had just proposed something as simple as a new sex position. To me she was like an astronaut, discovering all new galaxies and then casually suggesting we move on to the next cosmos.
That night, after the longest and most thorough shower I could manage, I masturbated more times than I can count, and for the first time I let my own hands wander back to my ass. I discovered that just a little bit of pressure on the outside made my pleasure skyrocket and I couldn’t believe I had never accidentally discovered this in the marathon of masturbation of my high school years.
The next day, I asked her to fly with me to that next galaxy. She warmed me up with her hands, and then, as she stroked my cock, she began to touch my ass. At first she stayed on the outside, moving in small circles. It blew my mind how good it felt. Like sparks flying down the length of my cock and up my spine at the same time. Then she grabbed a little bit of lube and started opening me up, and right as the first tip of her finger slipped in she took my cock deep into her mouth. I nearly passed out at the pleasure. I felt wide open, my cock throbbed and once again my orgasm took me beyond what I knew possible. I didn’t believe her when she said it was just the tiniest tip of a finger that had been inside. It had felt huge and frankly, overwhelming.
From then on, anal play was a pretty regular part of our sex life together. Trust me, I spent plenty of time pleasuring her, my face buried between her delicious thighs, my fingers expertly bringing her to multiple orgasms. We fucked in just about every position, we were barely twenty years old remember and had plenty of time to explore. As I learned to relax and open up even more to her gentle touch, she eventually worked up to having two fingers inside me, and began directly stimulating my prostate. Unbelievable. It felt like she was reaching inside me and pushing a button directly wired to my cock. My dick felt twice as large, and I could feel sensation from the sensitive head all the way back into my body. My orgasm built up from deep inside of me, and exploded out with tremendous power. Funny, it felt both like how I imagine women’s orgasms must feel, all internal and pulsing, but at the same time I felt like a superhero, more manly than I normally feel during sex. Anal play, I came to learn through Deanna’s skilled touch, put sex on hyperdrive. Everything felt bigger, harder, more powerful.
It felt so good I could not understand why this wasn’t taught to all guys, on those days they separate the boys and girls during gym class and reveal the secrets of reproduction. Why the fuck hadn’t I heard about this before? Either Deanna was part of a secret sex society or more guys were into this but just not talking about it.
We broke up when she graduated. That summer I quickly discovered that while I could touch my own ass a little bit while masturbating, I was never able to reach inside like she did, and it never felt quite as good while doing it to myself. When I asked the next girl I dated to try it out, that was the first in what would become a long line of rejection. Most girls were simply grossed out, others were confused. I tried to describe to them how good it felt but I didn’t get much interest on their part. One girl was willing to touch outside, but never go in. And now that I had a taste of how good it felt, living without it was pretty depressing.
At first I freaked out, like most guys do I suspect, and worried that I liked it a little too much. Why couldn’t I be satisfied with “normal” sex - blowjobs and fucking seem to be satisfying for most guys. The only guys I had heard of liking anal sex were gay men. Trust me, I have nothing against gays. My best friend from high school came out to me senior year and we are still tight. I live in San Francisco, where it often feels like they outnumber us straight guys three to one. But I had never been into guys, and I certainly don’t feel like a closet case. So what was with my new obsession with anal stimulation?
For answers I turned to the great oracle of our time, Google. My first searches revealed lots of graphic porn, men with entire fists buried in their asses. Not quite what I was looking for, though my mind was appropriately blown open to the possibilities. I didn’t even know what to search for - and believe me, I tried every combination of words I could think of. Eventually I found a few good sites that explained why prostate massage felt so good, and reassured me that a lot of straight guys like me were into it. That was reassuring.
I first came across the term “pegging” on a forum where guys were sharing their techniques for anal play, and sharing stories of how they got their wives and girlfriends to try it out. All of the guys were raving about pegging - encouraging us novices who had just experienced a few fingers here and there to take it to the next level. They described hot women wearing a strap-on, bending them over and fully penetrating their ass. I couldn’t stop reading their enthusiastic descriptions about opening up fully to anal penetration and feeling a hot woman behind you, claiming your ass and filling you with pleasurable penetration. Sign me up, was my first thought. Everything had felt so good up to that point I knew I wanted more.
I guess you can say it has become a bit of an obsession for me. Or at least a very persistent fantasy. I’ve been with a few girls since I graduated and moved to San Francisco, but none of them have been willing to do anything more than a little external touch while going down on me. I’ve thought about trying online dating, and entertained myself for hours writing ads I never put up. “Nice guy looking for lovely lady with strap-on,” “Peg Me Maybe?” or “Seeking Strap-On Lover” The thing is, I’m a pretty traditional guy. I don’t want just the sex, I want a relationship with a woman who is willing to be with me in all of these ways I desire, who is as interested in meeting my sexual needs as I am in meeting hers.
I feel pretty hopeful about Laura. I met her through one of the guys on my rugby team, her roommate is a lesbian and she grew up right here in San Francisco. You never know who will be into what, I’ve definitely learned that the hard way. But I like Laura enough to tell her the truth about what I want in bed, and I’m just hoping she doesn’t run for the hills.
I’ve had so many fantasies about her pegging me, it almost feels real. I imagine her slender body with a black leather harness accentuating her hips, her long blond hair swinging as she thrusts
into me, her small breasts quivering with every stroke. She would look fucking hot, and I would be so into having her be my first.
***
Dinner was fantastic, and once again we talked easily and openly. I love that we can move from topic to topic so easily, and that there is so much to say. We both work in the environmental sciences, but try not to get too focused on work during our dates. Global warming isn’t so conducive to romance. The concert was not quite as fabulous as I expected. The old jazz musician played like he was worn thin, as if he had wanted to retire years ago but still took these gigs to pay the bills. Laura seemed relieved when I leaned over halfway through and asked if she wanted to get out of there early.
“Thought you’d never ask” she said, and we quietly slid out into the cool evening air.
“Where to next?” I ask, holding her hand tightly as we descend the steep hill.
“Your place?” She says coyly, leaning in to kiss my cheek and ruffle my hair.
“Sounds good, how about we walk? It isn’t too far, we’d be waiting for the bus longer than it would take to get there. You good with that?”
I feel my nervousness rising in my throat, knowing it is now or never. It just isn’t the easiest thing to slip into conversation, asking a girl if she’d be interested in strapping it on.
“Absolutely, stretching my legs feels good after that cramped club. What was up with that guy? He was half asleep on his guitar. Thanks though, it was a sweet thought. Thanks for making tonight special. I feel a bit like a school girl celebrating such a small anniversary, but it has been a great.” She squeezed my hand.