P is for Pegging (The Fantasy A-Z Series) Read online

  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.

  “Hey darling, all clean?” She asks, propping herself up on her elbows in bed.

  “Yes m’aam, as per instructions. Thanks for that.” I said, a little bashful.

  “Come 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.

  “Do 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.

  “Yes, completely.” I say, kissing her for emphasis.

  “And you are ready to give yourself up to me completely, and I can do with you as I wish?” she asks, licking her lips.

  “Absolutely. 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.

  “Yes” 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.

  “Fuck 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.

  “More” 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.

  “Now, 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.

  “As you wish,” I say, knowing I will do whatever she beckons at this point.

  “I’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.

  “Don’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.

  “I can’t tell you how hot you look right now,” I say “It 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.

  “I 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 “Oh, I’m sorry, was there something you wanted?”

  “Take 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.

  “Oh 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 peri
neum.

  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.

  “That’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.

  “Flex 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. “We 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.