Contents:
Title
P is for Pegging
The Fantasy A-Z Series
About the Author
P is for Pegging
Part of the Fantasy A-Z Series
By Chris Maxwell Rose
of PleasureMechanics.com
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 śthe 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 śWant 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 śnormal” 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 śpegging” 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. śNice guy looking for lovely lady with strap-on,” śPeg Me Maybe?” or śSeeking 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.
śThought you’d never ask” she said, and we quietly slid out into the cool evening air.
śWhere to next?” I ask, holding her hand tightly as we descend the steep hill.
śYour place?” She says coyly, leaning in to kiss my cheek and ruffle my hair.
śSounds 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.
śAbsolutely, 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.
śDefinitely, babe, I want you to know how much fun I’ve had being with you. I really hope we have bigger anniversaries ahead.” I say, kissing her hand. She looks at me with adoration, her green eyes radiating pure affection.
śI’m so happy to be dating a nice normal guy for a change. You would be amazed at the freaks I’ve met dating in this city.” My heart sinks a bit, and I brace myself for the imminent rejection.
śSpeaking of freaks, there is something I have been meaning to tell you.” I say quietly, realizing this is my opening.
Laura stops in her tracks and drops my hand, crossing her arms over her chest. She looks devastated already, that sparkle I had just seen in her eyes replaced with speculative concern. śWhat, Dan, what is it?”
I pause and shuffle my feet, wondering about the best way to say what I need to say.
śWell first let me say I absolutely love the sex we have been having - you are fantastic in bed and I love everything we’ve shared so far.” Her arms tightened and I felt her gaze drop to the ground.
śBut. . .” She urged me on.
śWell I discovered in college that I am into a few things, and realized since then that most girls I date, well, they are not into giving me what I want.”
śHaven’t I been pretty open so far? Fuck, Dan, I just tied you up and fucked you silly last week. Why don’t you just drop the drama and tell me what you want?” Laura seemed to relax. I wondered where her imagination had gone that this was a relief.
śYes, you’ve been amazing and so I am hopeful you will have an open mind to what I am about to say.”
śTry me.” Laura said, shivering a bit against the wind and looking bored with the conversation.
śOk here it goes. I really love having my ass played with during sex, and fantasize about you to wearing a strap-on and fucking me in the ass.” I glance up, bracing myself for her response. My secret was out.
śWow.” Laura was laughing, but kindly. She grabbed my hand, and the contact feels reassuring. śI was expecting something really kinky with that set-up.” She grabs me by the arm and we keep walking, still in the direction of my place.
śSo you aren’t freaked out?” I ask, a bit shell shocked at her response.
śNot in the least. I can’t say I am experienced at all, but I’m totally willing to give it a shot. I know lots of guys who are into it, I don’t see how it is that different from anal sex on a woman. Which, by the way, I’m not that into so let’s not go there right now.”
We walk in silence for a few minutes. My heart is beating. Give it a shot! Fuck yeah! That is all I have ever asked, but the responses have always been so cruel.
śWow, you really are amazing. Thanks for being so open minded. Other girls I have asked have been totally freaked out.”
śI am not other girls, my dear. Thought you would have learned that by now. Haven’t I ever told you about the time I wore Lee’s strap-on for Halloween?”
No, no you most certainly have not, I thought, as she launched into a story about borrowing her roommate’s strap on for a costume party, where she went as Captain Condom. She wore a big red dildo and wrapped her body in saran wrap, for some Castro party where the theme was Superheroes of the New Millennium. My cock sprang to attention at the thought of Laura in nothing but plastic wrap and a strap-on.
By the end of her story we are at my doorstep, and I find myself fumbling with the keys in my excitement. Laura leans into me, kisses my neck and says sweetly. śEasy there tiger, let’s just have fun tonight. For our next date you can take me to a sex shop and get me suited up. Sound good?”
Sounds like a fucking dream come true, that’s how it sounds. I got the door open quickly, we rush upstairs and I find myself newly in love with this woman. I spend extra time making sure she is happy, giving her very enthusiastic oral sex until she is too sensitive for more. She gets on top, and as she is riding my cock she looks down, grabs my chest and says śYou want to take it in the ass, is that what you want? I’ll give it to you nice and slow until you are begging for every inch.” Just her words send me soaring. Her words and her willingness are enough to propel my pleasure to the next level, and I can only imagine what is ahead for us.
***
I’m waiting on a busy street corner, waiting for Laura to arrive. Today is our big date to the sex toy store to get her equipped. All week I have been fantasizing about her strapping it on, and I just hope I haven’t built it up too much. She has been amazing, teasing me by sending me photos of hot women in harnesses, men gasping with pleasure as they are entered from behind. I’m thrilled that she has been doing a bit of internet research herself. She even sent me a photo of her trying on Lee’s strap-on, but the photo only included one sexy round hip, the leather strap of the harness accentuating the feminine curve of her hip and ass. The tease of it makes me hard every time I look at the photo. It has been a long week, and I am so ready for the fantasy to become a reality. I glance at my watch, I am still ten minutes early. Over eager I guess.
Mercifully, she is a few minutes early as well, and I spot her waiting on the other side of the traffic light. Our eyes meet, and she flashes me an incredible smile, warm and sexy all at once. She looks amazing - tight black jeans with knee high black leather boots, a silver zipper up each side and just enough of a heel to make her float a few inches above the earth. A simple red shirt with a low neckline accentuates her beautiful neckline, and her hair is pulled back in a slick ponytail. A big black leather bag is slung over her shoulder. We hold eye contact until a bus whizzes between us, and when it is gone the light has changed, and she is walking towards me. My knees go weak as I realize this woman is coming for me, of all the men in this city, she is ready to give her attention and her body to me alone.
I am so excited to grab her up into my arms I want to rush into the street and stop traffic in all directions with a long kiss. I try to play it cool and wait for her to step up onto the sidewalk before I reach for her, pulling her tight into my arms.
śYou look gorgeous!” I say, wrapping my arms tightly around her and kissing her neck, all the way up to her hairline just below her ear. She smells amazing, she feels amazing and I am dizzy with excitement. I find myself almost glad that all those other women refused me, so I can experience this for the first time with her, this generous goddess.
śThanks babe. It is not often that I get to go on shopping dates. You ready?” She slides her arm through mine and we walk, arm in arm, as she tells me about her week at work. She doesn’t seem nervous at all as we approach the bright friendly windows of the women-owned sex store. I wish I could say the same. This is new territory for me, the only sex store I’ve been in was a dark windowless warehouse on the side of a freeway. Here, on a bright and busy San Francisco street, this store fits in with the high end boutiques and pet stores, and no one seems to notice when we slip inside. The windows are decorated with colorful vibrators dangling from cardboard clouds, with the phrase śMake It Rain” cheerfully inviting people to explore the art of female ejaculation.
We are greeted by a big friendly woman with a shaved head, her arms fully tattooed and her shoulders much broader than my own. śHey folks, let us know if you have any questions or want a demonstration of anything!” her voice is low and powerful, and she smiles at us as she shuffles papers around behind the counter. My eyes are bugging out of my head as I take in the store. The walls are lined with sex toys of all varieties, rows of dildos and vibrators in shapes and sizes and colors beyond imagination. Towards the back there is a huge display of books and videos, and little display islands around the store had groupings of sex toys for every appetite. Glass cases hold antique vibrators with little informational plaques next to them, and other displays show off the gold and diamond encrusted vibrators that sparkle in the sun.
Laura squeezed my arm and started wandering about, looking casually at vibrators in the shape of rubber duckies and prancing dolphins. śHey, I’d love to get something special for you, pick out something for yourself, ok?” I whisper in her ear. She smiles back and gestures wildly to the whole store śI’ll take one of each! I love this stuff!” She snatches up a particularly large vibrator and flicks it on, touching it to the point of her nose and giggling at the buzz.
śI don’t think that is where it is meant to go, honey” I say, smiling at her playful enthusiasm.
śActually, she seems to know what she is doing. The tip of the nose is one of the best places to get a sense how a vibrator will feel on the clitoris.” A willowy man has slipped up behind us, and I eye his nametag to make sure he is an employee, not a creep hitting on my girlfriend. śHey, I’m Jack, did you all need any shopping assistance today?”
Before I could stammer a firm śNo thanks,” Laura has extended her hand and is shaking Jack’s enthusiastically. śHi Jack!” she says, still holding on to me with her other arm. śWe are in the market for a strap-on set up for our first foray into pegging. What do you recommend?”
I feel my face flush crimson, brighter than any of the vibrators on display, and I want to flee. But Jack casually guides us to a wall of harnesses and begins pulling a few down. Everyone here is just so casual about this, I am trying to talk myself into adopting the attitude and pretending like this is no big deal. But my heart is racing and I can’t stop grinning and blushing as they discuss the advantages of various models of harnesses. There is black leather and red leather, vegan faux leather and cheap nylon, silvery sparkly vinyl and furry cheetah print. A harness for every occasion, it seems like.
Laura hands me her purse and starts allowing Jack to help her into a black leather two strap harness, and I clutch her purse tight to my body, suddenly grateful for the shield. My cock has sprung to attention at the sight of Laura strapping on the harness, and we hadn’t even made our way over to the dildo section yet. Jack explains the options and it feels as complex as buying a new car. The basic model will hold a dildo in place, but you can upgrade to one with a little pocket for a vibrator, or even a removable panel for a double ended dildo. Snaps or D-rings? Washable vinyl or flexible leather? Laura models a few of her favorites including a sparkly silver number that makes her look like a Christmas tree wrapped in lights. She finally chooses one of the simpler black leather versions, and when she looks at me she is beaming. śGoes with my boots!” she says proudly, looking like she is ready to wear it right out of the store.
Jack leads us over to the wall o’ dildos, where silicone cocks are lined up, sizes ranging from just a couple inches to gargantuan toys the size of my entire arm. Jack launches into a size-queen speech that I can tell he has given many times before. śMost people buy too large a toy on their first go. We recommend starting small and working your way up. Most guys feel quite full with even the smallest of sizes. The bigger ones are great for vaginal penetration so if you are going to double-duty you could pick something in the middle, but I’d recommend this little guy.” He thrusts a tiny quivering toy into my hands, it is only about four inches and skinny. It does have a nice weight to it and is super soft but with a hard core. I squirm a bit, feeling strangely like I am holding a dismembered penis. I hand it over to Laura as Jack continues śIt has a nice curve to it, which will hit the prostate nicely as you slide in and out.”
The forums are one thing, but I find myself a bit in shock as we are discussing the features of something that will be sliding in and out of my asshole. I freak suddenly, wondering if this would have been best left to fantasy alone, until I see Laura fingering a sleek black model that looks more like an exotic animal horn rather than a penis.
śWhat about this one, Dan, or do you want me to have a veiny cock with realistic balls?” My eyes flash over the simple curve of the black dildo she is holding and I am relieved that it doesn’t have much in common with a prosthetic penis. I could see the appeal for some, but I just want something that will feel awesome, I don’t need any realistic visual details. śThat’s the one!” I declare, and toss it into the basket.
Jack makes sure we are fully stocked up with lube, and as he and Laura discuss the merits of water-based vs. silicone lube for anal play, I sneak around the store and throw a few more things into the basket: a massage candle, beautiful satin restraints for bondage and a sleek looking vibrator for Laura. I want to make sure she feels taken care of, I don’t want our sex life to become all about me just because she is willing to explore this fantasy of mine. She slides up to me as I am pondering a range of paddles and floggers. She’s right, this store is awesome and my mind is racing with the sheer variety of erotic possibilities at every turn.
śYou want one of everything, right? I’m telling you, this place is Disneyland for adults. C’mon, I think we have enough to explore for now.” She says, as she tosses a heavy bottle of lube into the basket. I hand her back her purse and head to the register, where the huge butch woman rings us up. I was prepared to spend a small fortune, and with the inclusion of all the extras I am well over $300 when she hits the total button. It feels almost naughty, spending money on sex like this, but when Laura presses into my side and kisses my cheek, my credit card bill is the furthest thing from my mind. The friendly woman slides a big white shopping bag across the counter, and I notice she has wrapped everything in red tissue paper, slid in educational pamphlets and a few announcements about upcoming events. śSee you guys soon. Have fun and stay safe!” she says, smiling at Laura in particular.
śOh we definitely will!” Laura says, and thanks Jack over her shoulder as we head towards the door.
The brisk wind feels amazing as we hit the street, and I feel Laura’s excitement in her quick pace. She is nearly galloping alongside me in her boots, and I check to make sure she actually hasn’t worn the harness out with her. I can’t believe how into this she is. śGod I love that place! So many ways to get it on! To think, so many people limit themselves to meat and potatoes when there is a whole buffet of options. Thanks honey, that was fun.” I am reeling at the fact that she is thanking me, when I am the one high on the idea of my fantasy finally coming to life after all these years. I seriously think I could love this woman.
śAre you hungry? I’m could definitely go for a burrito, there is a great place in this neighborhood.” I say, not really thinking it through. Laura stops in her track and laughs at me.
śA burrito? I think not. I’ve got plans for you this evening. C’mon there is awesome sushi right around the corner.” I don’t even have time to blush before she is leading me by the arm towards the intersection, and my heart soars once again for this gorgeous goddess of a woman, who is embracing my desire so fully and who seems to be getting sexier every time I look at her.
***
We’ve arrived back at Laura’s place, and I am jumping out of my skin with excitement. We had a totally normal date at the sushi place, discussing everything but the toys that were in the bag on the chair next to her. Yet there wasn’t a moment that I forgot about the harness and the dildo, all wrapped up in red paper. I couldn’t stop staring at Laura’s mouth as she slid tender pieces of fish past her lips. I could barely eat I was so excited, but Laura had no problem finishing off our big plate.
Now we are in her apartment, and she has let me know that her roommate is away for the night, giving us the privacy that is so scarce in this tiny San Francisco flat. Normally, if you sneeze everyone hears it, one of the reasons we end up back at my place more often than not. But for this occasion, Laura wanted to be in her own place, śher own lair” as she calls it.
I’m on the couch, ready to tear off my clothes and dive into my fantasy. But Laura is taking her time. She emerges from the kitchen with drinks, tequila on the rocks with lots of lime. She hands me a glass as she slides onto the couch next to me.
śCheers to new adventures together!” she says, raising her glass and looking me right in the eyes.
śCheers!” I echo, clinking glasses. I take a deep long pull on the tequila, enjoying the rush of heat down my throat.
śNow, here is what is going to happen. I’ve done my research and studied some very awesome techniques for giving you back door thrills. I’m really excited to see how you respond. But I also want to say again that I’ve never done this before, so I’m going to ask for some patience and we’re going to take it slow, ok?” She pauses and sips her tequila, looking at me through her eyelashes as she sips.
śUh, yeah, of course.” I manage to mutter.
śWe’re going to use a safeword, just in case you go non-verbal and can’t tell me how you are feeling. So as I am opening you up and beginning to fuck your ass, please use green to mean everything feels good, yellow will mean slow down a little and if you say red I’ll stop totally and slowly pull out. Ok?”
I nod and I pause for a moment. All of a sudden this is feeling a little intimidating. I appreciate that she has done her research, but nothing I experienced in the past hurt at all and I am wondering how much more intense the dildo will be, when all I have experienced was fingers. I built this up so much in my fantasy I didn’t think much about the possibility of it hurting.
śAnything else you want to say?” Laura asks, knocking back the last of her tequila.
śJust thank you, I guess. It’s really cool how you are so open to trying this. It is something I have wanted for a really long time.” I say, looking down at my lap.
śYou are so welcome. Now, you have no plans tomorrow, right?”
śNone, I cleared the weekend for you as requested!”
śGreat, so we have tons of time. We’re going to take this nice and slow.”
Laura takes my glass from my hand, sets it on the coffee table and then throws her leg over my lap, mounting me. My cock rises from the sensation of her weight on my lap, her breasts grazing my chest as she leans in to kiss me. I move my hand up her back to the nape of her neck and gather a fistful of her hair. She is grinding her hips just enough to tease me and make my cock throb against my jeans. She gasps as I pull her head back and kiss her neck, all the way down to her collarbone. I release her and she looks me straight in the eyes, and the energy between us is palpable. She puts both hands on my chest and leans in hard, kisses me and bites my bottom lip a bit.
I realize she is enjoying being on top, being in control, and I am more than happy to yield to her. I twist my body and sink into the couch, and she leans her weight into me, pinning me against the black leather cushions. Her long blond hair is falling down all around my face as she leans in to kiss me, her hips still moving in circles. Then she sits up and takes her shirt off in one smooth motion, tossing it aside. Her black bra frames her small breasts beautifully, and her little waist is flexing as she moves her hips into me. She unbuttons my shirt, one button at a time, and then rakes her nails down my chest, hard enough to make me gasp.
She sits up and smiles down at me. śI’m so looking forward to this. I want to open you up really slowly, so you can feel every inch slipping in. I want to hear you moan. But first, you get to go shower. Clean yourself really well, take your time in there, and then come meet me in the bedroom.” With that, she dismounts and walks casually to the kitchen, disappearing from sight. She leaves me gasping for breath and hard as a rock.
In the bathroom, I realize how much she has prepared for this event. On the sink by the toilet is a little bag from the drugstore with a post-it note reading śInstructions: Take your time to empty out. Then fill this with plain warm water and rinse until clear. Your ass is mine, and I want it clean. When you come to me, come naked.” In the bag I find a magazine and a little bulb enema. It looks like the bright nose of some perverted clown. I settle in with the sports magazine and try to relax enough to go, and again marvel at the effort Laura has already gone to in order to bring my fantasy into reality. I suddenly hope that I actually enjoy this as much as I want to, after so many years of yearning. I hear that she is blasting music in the other room, and is in no rush for me to finish up this part of the preparation. So I relax into the moment, and follow her instructions to the letter.
***
Laura’s bedroom door is closed, so I knock lightly.
śCome in!” she calls and I push the door open. Warm air rushes towards me, and I notice she has been running a space heater to make her room a cozy lair in the midst of the chilly San Francisco afternoon. I quickly shut the door behind myself, trapping the warmth.
Laura is stretched out on the bed, and looks like a pin-up goddess. She is wearing gorgeous red lingerie, and over her underwear she is wearing the black leather harness. Her blond hair is fanned out over the pillow, and she is smiling. I notice that the bedside table has been laid out with all sorts of tools and toys, including a box of gloves, the big bottle of lube and the black dildo. She has lit candles on both sides of the bed and trancey techno music is filling the air.
Unsure of what she wants from me, I just stand, naked and exposed before her. The sight of her has made my cock start to come life, and I can feel it bobbing in the warm air.
śHey darling, all clean?” She asks, propping herself up on her elbows in bed.
śYes m’aam, as per instructions. Thanks for that.” I said, a little bashful.
śCome here, and get on your knees at the foot of the bed.”
I approach slowly, taking in the sight of her as she stares me down. As I get to the bed, I notice she has put a pillow on the floor. She really has thought this through, a fact I am finding wildly sexy. Is it possible she is as into this as I am?
I sink to my knees, grateful for the comfort of the pillow underneath me. I stare at her and await further instruction. She slides towards me, feline and graceful in her movements, and pivots so she is on her hands and knees, facing me. She leans onto her elbows, take my chin in one hand and raises my face to her own. Still holding my chin firmly, she kisses me.
śDo you trust me?” She says, staring into my eyes. At such close range, I can see the amber streaks in her bright green eyes, and I am mesmerized. Her mouth tastes like limes and tequila, and I am beginning to fall under her spell.
śYes, completely.” I say, kissing her for emphasis.
śAnd you are ready to give yourself up to me completely, and I can do with you as I wish?” she asks, licking her lips.
śAbsolutely. I am yours.” My cock throbs as I say this, and I take a moment to cherish the idea of giving myself up, a new virginity ready to be surrendered.
She kisses me, first my lips and then each cheek and my forehead. Then she flips over and sits so she is just in front of me, and throws her legs over my shoulders, pulling my face towards her crotch. Her powerful thighs grip my head and press my face into her. I am overwhelmed with excitement as I smell the new leather scent of the harness mixed with her earthy fragrance. I can feel the leather and the silk of her underwear pressed into my face, and I eagerly bring my hands up and wrap my arms around her legs. I take a deep breath in and then exhale, pressed right up into her so my breath floods her pussy with warm, wet heat. She moans and grips me tighter with her legs.
I reach up as far as I can and run my hands down the sides of her body, across her hips and around her thighs. Over and over again I reach and slide my hands along her body, covering her in feather light touch. She moves into my touch and begins moving her hips, grinding her sex into my face. Then she reaches down and moves the fabric of her underwear aside, exposing her wet lips underneath the small leather patch of the harness. I eagerly move towards her, nudging her lips open with my nose and chin as I gently slide my tongue up and down her inner lips. She is wet and aroused, her clitoris swollen and pink, glistening with her fluids.
śYes” is all she says as she grabs my head and clutches it close to her body, and my whole face is buried in her sex. I take her entire clitoris into my mouth and suck gently, flicking the tip with my tongue. I keep touching her sides and belly with one hand and bring the other down to the entrance of her pussy, resting my finger just outside for a moment while I continue to suck and lick her clit. She is breathing hard and I can tell she is going to come soon if I keep up what I am doing, so I shift it up a bit to keep her going a bit longer.
śFuck me now.” She growls, and following instructions I quickly slide one finger into her, and suck harder on her clit and lips. I curl my finger up and run it along the warm flesh. She moans deeply and I feel her contract around my finger.
śMore” she says, and I add another finger. I hold still and she starts moving wildly around my hand, moving in circles and arcs. Bearing down with my face, I take over and slide my fingers in and out until I feel her start to clench around me and hear her growl turn into a low wail. She clutches the sheets on either side of my face and her thighs tighten around my shoulders. Then she collapses, panting, and I rest my head on her thigh, watching her pussy pulse, wetness dripping across her red lips, my fingers glistening as they rest outside her body.
After a few moments, Laura sits up and strokes my hair. Then she pats the bed next to her, inviting me up to join her. As I stand, I shake out the stiffness in my knees. Once I am on the bed, she gestures to the top of the mattress, inviting me to lie all the way down.
śNow, do I need to tie you up or are you going to follow orders?” She says, kneeling over me, peering down with her big green eyes.
śAs you wish,” I say, knowing I will do whatever she beckons at this point.
śI’ll keep your hands free, for now at least. Get comfortable.” She says, beginning to run her hands down my chest, around my hips and over my thighs. She touches everything but my cock, which of course makes me think of nothing but how her hands will feel once she gets there. I am fully erect, at attention and under her spell.
Still running her hands over my body, she leans down and takes just the tip of my cock in her mouth. The sudden warmth makes my hips buck, and she firmly pushes my hips down, looking up at me as she starts to sink her mouth deeper. I try to take deep, rhythmic breaths, wanting to draw this out as long as possible.
Laura wraps her hands around the base of my cock and holds firmly as she sucks just the head. I close my eyes and soak in the sensations. Exquisite pleasure courses up and down my body.
I open my eyes as she stops suddenly, and I see that she is leaning across the bed, grabbing supplies from the bedside table. She struggles as she tries to get a tight glove on her hand, and we both laugh. I know she has planned this all out but I remember how new to this we both are. As she finally gets the glove to fit smoothly over her hand, I smile up at her, and want to let her know how much I appreciate all the effort she is going to. But before words can reach my lips, I see her reach for the dildo. My breath catches in my throat. All of a sudden it looks huge and formidable. I feel my ass clench in rebellion.
śDon’t worry, we still have a lot of warm up to go. I just want to have it on for when we are ready.” She says, her face twisting in concentration as she slips the dildo through the stretchy ring held in place over her pubic bone by the straps of the harness. She fidgets with it, adjusting it so it is positioned just so. She looks down at herself and then up at me, and we both smile. She sits back on her knees and strokes the dildo with fascination.
śI can’t tell you how hot you look right now,” I say śIt is strange and beautiful at the same time.” I say, drinking in this image of Laura, her breasts cradled in a sexy bra and flaunting a few inches of black silicone. I’m relieved we didn’t get a realistic looking toy, this sleek black look is perfect for her. I’ve seen so many online images of women with strap-ons, but none of them compare to how sexy this is in real life.
śI could definitely get used to this!” She says, continuing to play with the toy, pressing in and grinding her hips into the base. Then she looks up at me and teases śOh, I’m sorry, was there something you wanted?”
śTake your time, darling, the view is great from here!” I reply, stroking my own cock lightly to keep myself hard as she gets used to her new accessory.
She moves towards me on her knees, and lies on top of me. The weight and heft of the toy is between us, and feels totally alien but weirdly stimulating at the same time. We kiss, and I can tell by her enthusiasm that she is enjoying this erotic experiment.
When I try to flip her over so I am on top, she remembers her dominant role and sits up suddenly, shoving me back into the mattress with all her weight.
śOh no you don’t. Your ass is mine tonight!” She says with a hint of devilish glee in her voice.
She leans over to the nightstand and pumps the thick clear lube onto her gloved hand. Then she moves back so she is kneeling between my legs, her dildo bouncing with every movement.
She bows down again, taking the top of my cock in her mouth, wrapping the ungloved hand around the base of my cock, and then slides the gloved hand down past my balls and begins gliding over my perineum.
I am flooded with memories of the sensations of when I first explored this in college, and all of a sudden I am not worried about what is to come. My body lights up with sensation as she slides her hand down and around the outside of my ass, making the whole area slippery with lube.
She continues to work my cock as her hand explores the area. I can tell she isn’t quite sure what to do, so I drop one of my hands and rest it over hers, guiding her in what my body remembers it loves. First I show her how to push deep into the perineum, and I can tell she is hesitant to use so much pressure until I moan with pleasure, and then she pushes into me with more muscle. As she pumps onto the perineum I feel my cock swell, growing impossibly larger even though I am already as hard as I’ve ever been. Again, I breathe deeply and try not to let myself slip too close to climax.
I take her hand and move it back down to my ass, and show her how to move in circles and gentle pulses right over the opening. Each move feels incredible, my nerves are on fire and I can feel each tiny movement as if it was a huge acrobatic act on my ass. I need to focus on feeling more and more sensation so I can take it all in and not be overwhelmed.
Laura comes up for air but keeps stroking my cock with her one hand while she plays with my ass with the other. She looks at me, and I nod in approval of all that she is doing. I feel her hand shift and focus more on the incredibly sensitive area right at the opening. I remember Deanna encouraging me to breath and relax, way back when I was first learning about this new arena of pleasure. So I take breath after breath and just focus on relaxing, and flex my butt muscles a few times to try to feel more precisely what is going on down there.
As I exhale, I feel one of her fingers slowly slide into me. I gasp at the sensation of opening up to her, and she lets out a little growl.
śThat’s right baby, I’m inside you now” she says, and I feel her arousal in her voice. I find myself thinking about this switch, feeling my girlfriend inside me instead of the other way around.
New sensations wash over me, and I want more. I look up at Laura, her brow furrowed in concentration, and let out sounds of pleasure, wanting her to know how good it feels.
She continues to stroke my cock slowly, and with each stroke I feel sensations move from the base of my spine all the way up through the entire length of my dick. I feel huge, like my cock is enormous and powerful and connected to my entire body.
Soon, she has a finger in my ass all the way, and I feel her start to glide along the prostate. It almost tickles, it is such a new and unexpected sensation. Mostly, it just makes me want to ejaculate, and all of a sudden I realize I’m not going to be able to hold off much longer.
I feel my ass muscles clench around her finger, and when I look up at her she has her eyes closed and is smiling. I buck my hips, and her grip on my cock tightens. As her finger moves gently inside me I feel my entire pelvis clench and then I am past the point of trying to draw this out any longer, my orgasm is exploding from deep within and I am coming hard. My eyes squeeze shut and I let out a deep roar as my pleasure explodes, and then it is all I can do to catch my breath.
Laura must have just held still inside me, because a few minutes later I hear her voice.
śFlex for me a few times, babe.” She says, and I open and contract my butt a few times as she slides her finger out. My cock jumps at the sensation of her sliding out, but I am spent.
She leans over and kisses my chest a few times, then jumps up and scrambles to the bathroom. I hear the faucet running as she washes up, but mostly all I can focus on is the warm streaming sensations running through my body.
When she comes and snuggles next to me, I notice she has taken off the harness. Her body feels amazing pressed next to me, and I doze off feeling the warmth of her breath on my neck.
***
I wish I could report that the next morning I took the full length of the dildo like a champ, and that we spent the rest of the weekend fucking like bunnies. The truth is, the next morning I was more interested in a great brunch than being pegged.
Don’t get me wrong, I was still eager for sex. But after so many years of craving anal play, the one event felt so deeply satisfying that I didn’t feel like I needed to repeat it. So when we woke up that morning, I was more than happy to spend my time pleasuring her, taking my time to work her up to a series of orgasms that sent her howling. We brought the new vibrator into bed to give it a test run, and she rode my cock as she pressed the smooth toy into her clit, and grabbed my chest so hard as she came that I had bruises for a week. Then I took her out to a fancy brunch place, where we took turns cracking little sex jokes as we talked about the week ahead and luxuriated in that romantic casual vibe that is one of the best parts of eating Sunday brunch together after a good weekend of fucking.
Our sex life remained on fire month after month, as we started adding weekday sleepovers to our weekend date routines. I kept waiting for it to get routine and boring, but that never happened. We went back to the sex store a few times and bought new toys to experiment with, and it seemed like the closer we got the hotter the sex was getting, as it got more intimate and honest.
Laura was always open to adding some anal touch into the mix, and I had almost forgotten about the big event of being pegged. Fingers, I found, were more than enough to give me that intense sensation and make my orgasms twice as potent. She gradually worked up from just one finger to two and then three, and the fullness and bigness of penetration was more than enough for me. She even let me start to play around with her ass, just on the outside, and was shocked that she enjoyed it after so many attempts at anal sex that just ended up being painful and embarrassing.
It is funny how you can fantasize and yearn so deeply for something for so many years, and then let go of the desire for it so easily. I felt totally satisfied with my sex life with Laura - not only had I found an open-minded woman who was down to experiment with my unusual desires, but she was turning out to be more than I could have ever hoped for. After less than a year of dating her, I was beginning to seriously consider asking her to move in with me and even found myself thinking about spending the rest of my life with her. I was in love, I was shocked to discover, and the overwhelming need to experiment with pegging had taken backseat to the fact that I was just simply smitten with this woman.
So being pegged was the last thing on my mind when I went over to Laura’s last Friday night. She welcomed me with a long kiss, we sat and talked over a few glasses of wine, and eventually I excused myself to use the bathroom. I noticed a sly smile as I stood up, but didn’t know what to make of it.
When I got to the bathroom, I found the little red bulb enema and another love note. śWe have unfinished business. If you are up for it tonight, use this well, take a shower, and report to bed.” A clean fluffy towel was laid out for me. I paused for a minute, and then decided to go for it. I felt up for the adventure.
When I returned to the bedroom, I found Laura standing by the window, leaning into the wall and gazing out to the busy San Francisco streets. She was stunning. She was wearing knee high black leather boots, the harness and dildo, and a black and red corset top that pushed her small breasts together and sculpted her body into a sleek hourglass. Her long blond hair fell around her shoulders, and the arc of the dildo subtly emphasized her curves. Damn she was gorgeous. My cock immediately came to attention as I walked towards her.
She turned to me, and wordlessly began kissing me hard, pushing me towards the bed. I stumbled back under the weight of her enthusiasm and let her guide me as she kissed me and ran her nails down my back and chest.
When I hit the mattress, she immediately flipped me over so my face was down and my ass in the air. I felt her mount me, straddling my hips and resting her full weight on my ass. Then she ran her nails up and down my back with increasing intensity until I was gasping for mercy. Next came kisses and long licks, up and down the sensitive tracks she had made with her nails. She bit at my shoulders ferociously, not letting up until I cried out.
I was still reeling from all of the sensation on my back when I felt the first blow on my ass. I felt her hand come down and heard the sound of the spank at the same time, and the shock of it made me laugh out loud.
śOh is this funny? Huh? I guess it isn’t hard enough if you are laughing!” She said, with an edge of laughter in her own voice. Then the spanks came one after another, until my ass was sore and the skin on fire. She played with the hot flesh, pinching and biting my cheeks. I groaned and tried to focus on all of these crazy sensations, changing so quickly sometimes I couldn’t tell what was happening.
Then I felt her hands pulling at my hips, and I moved back towards her so I was on my knees and elbows, my ass high up in the air. For a moment I felt a strange flicker of shame, being all of a sudden in this position that is so strangely primal and yet so vulnerable. But that passed quickly when I felt Laura’s hand reach between my thighs and wrap around my hard cock. She had obviously lubed up her hand because it glided along the shaft smoothly. After a few strokes, she let go.
śTouch yourself all you want, I’m going to focus back here.” She said, giving me permission to continue stroking my cock. I was eager to follow her command, and grabbed my dick as I buried my face in her soft sheets.
I felt her finger begin to circle my asshole, which was so exposed in this position she could touch every inch of the area easily. She pressed in with deep but broad pressure, and I moaned into the bed as I felt my asshole begin to open up to her touch. It was becoming easier and easier to relax and feel the sensations, the more we played with my ass, and I was able to just feel how amazing it felt to feel her finger slide in and out, my muscles yielding open with every stroke.
She pulled her finger out and I could hear the snap of the latex as she stripped the glove off. She rested one hand on the base of my spine, and used the other hand to scratch my back and spank the sides of my ass.
It was then I felt the tip of the dildo resting outside my ass. She didn’t push, she just let me feel the weight of the toy massaging my ass as she slowly moved her hips in small circles.
The tip of the toy was smooth and heavy, and felt amazing against my ass. I gripped my cock harder and pushed back a little, taking a deep breath and flexing my ass open into the heft of the toy. Her hands gripped my hips, and I felt my cock swell with arousal as the tip of the toy entered me. It felt impossibly huge as it slid past both rings of muscle and I couldn’t help but start to move my hips back and forth, exploring the sensations as the entire length of the toy slowly slid into me.
Laura held still, allowing me to direct the motion at first. I glanced over my shoulder and our eyes met as she beamed at me, a wicked look in her eyes. As we gazed at each other, she raised a hand and slapped my ass firmly, making me gasp out loud. I could feel my ass flex around the toy with the impact and was stunned at how incredibly good it all felt.
Slowly, she started to take over, thrusting her hips back and forth to move the toy in and out of me, stopping just short of pulling it out completely each time. Occasionally she slapped the side of my ass or raked her nails down my back, and the added sensation would send me flying blind through a wave of pleasure.
Then her movements slowed, and I felt her clutch at my hips firmly. She started rocking her hips, and the motion made the weight of the toy rise and fall on my prostate, like a slow drumming that sent pleasure out through my entire cock and up my spine at the same time. I took a deep breath, stroked my cock firmly a few times and was launched into the throes of the most powerful orgasm I have ever experienced. My entire body was singing with sensation as she gently pulled out, and I collapsed onto the bed, laughing with joy at how good I felt. She undid the harness, tossed it onto the bedside table and collapsed on top of me, playfully kissing and pinching me as I recovered.
When our eyes met, there was nothing but affection and possibly even love. She was glowing, as if she was the one who had just had a full body orgasm.
śDamn that is a lot of work, I have to give you guys more credit now!” she laughed as I stroked the hair off her sweaty face.
śThank you babe, that was incredible” I managed to utter in between breaths.
śFuck yeah, that was fun! It is so hot to see you move, to watch the toy moving in and out of you. I swear I could feel you, I think I have phantom cock syndrome!” Laura joked, rolling on top of me. She reached around and undid the clasps of her top, tossing it on the floor as her breasts bounced back to place. She was hot and sweaty and radiant.
I reached up and grabbed her hand, bringing it to my lips and kissing each finger, one by one. I lingered on her ring finger, looked up at her, and wondered how long I had to wait before asking her to marry me. In that moment, I felt like I had all that I ever could want and more, and silently vowed to keep this good thing going.
She must have read my mind, because she got very serious and smiled down at me. śWhat are you thinking right now?” she asked, grinding her hips into me a little bit.
śI was just thinking about how amazing you are. And how it is kind of unfair to kick your roommate out all the time for our dates.”
śWhat, do you want her to listen? Or join in? Not going to happen, Lee is not into guys like that.” She said, a little confused.
śNo, I guess I was just wondering if it is too early to invite you to move in with me.” My voice trailed off, as I desperately tried to sound less serious, suddenly aware of what a big step this was. But Laura just smiled, grabbed my hand and clutched it hard.
śYou do know that in this city living together is almost as serious as marriage, right? I would be giving up a rent controlled apartment in the bargain.”
śWell yeah, but, you know, I don’t happen to have a ring on me at the moment.” I joked, hoping that wouldn’t freak her out.
She leaned into me and kissed me deeply. I wanted to take that as a yes. Then she leaned over and fumbled with the harness for a minute. When she leaned back up she was holding the black ring that held the dildo in place on the harness, and she looked down at me with gleaming eyes.
śYeah, but I do!” She said, as she wrapped her hand around my cock and slipped the stretchy black ring all the way to the base. Then she stretched out on top of me and kissed me, still holding my cock with one hand.
I should have known our engagement would be as untraditional as the sex we were having, as modern as this city we were living in. She didn’t even move in for a few months, and we aren’t planning to get married anytime soon. But I think both of us think back to that night as the moment we both knew it was forever. As she slid that ring around my cock, I knew I had found the woman who would adventure through life with me, fulfilling one fantasy at a time.
The Fantasy A-Z Series:
A is for Anal
B is for Bondage
C is for Cuckholding
D is for Domination
E is for Exhibitionism
F is for Fisting
G is for Golden Showers
H is for Harem
I is for Intergenerational
J is for Jealousy
K is for Kama Sutra
L is for Lingerie
M is for Massage
N is for Naughty Nurse
O is for Orgy
P is for Pegging
Q is for Queer
R is for Ravishment
S is for Spanking
T is for Threesome
U is for Underwater
V is for Voyeurism
W is for Whips
X is for X-Ray Vision
Y is for Yearning
Z is for Zero Gravity
Each short story in this series is designed to explore a common fantasy through explicit erotic fiction. Titles will be released one at a time, in order of popular demand. Vote for your favorite (or suggest an additional title!) at www.PleasureMechanics.com/FantasyAZ
As one half of the sex educator team The Pleasure Mechanics (www.PleasureMechanics.com) I have been writing about sex for over a decade - mostly focusing on sexual technique how-to guides as part of our commitment to teaching the physical skills of pleasure. I’ve always loved to write, but only in the past few months have I given myself permission to turn my passion for the pen towards writing erotic fiction. I am dedicated to teaching about sexual pleasure, and believe that great erotica can both entertain and educate, offering the opportunity to explore your own arousal and turn-ons while temporarily slipping into the skin of my characters as they explore the vast world of sexual potential.
I started my erotic fiction writing adventures with the Fantasy A-Z Series because I am fascinated by the universal themes that emerge when the most common sexual fantasies are examined. Underneath our very personal fantasies are the common themes of power and seduction, longing and yearning, adventure and ecstatic journeys. We, as human erotic creatures, are all capable of a vast range of erotic experiences and yet many of our sexual realities are very narrow and predictable. I believe that erotic fantasy is one of the most powerful ways to safely explore the universe of erotic potential and discover your unique constellation of arousal and desires.
I write with the earnest hope that you will get turned on, see yourself reflected somewhere in these pages, and discover something new about yourself as an erotic creature. I’d love to hear from you - you can always contact me through our website, www.PleasureMechanics.com. While you are there check out our bestselling videos, stroke-by-stroke guides to touching every inch of your lover’s body. Our website also offers an extensive A-Z index of sexual information, techniques and strategies to maximize your experience of sexual pleasure.
I’ll be releasing new volumes of The Fantasy A-Z Series over time. Check out upcoming titles and vote on what will be written next at www.PleasureMechanics.com/FantasyAZ
Cheers!
Chris Maxwell Rose, PleasureMechanics.com
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