P is for Pegging (The Fantasy A-Z Series) (4 page)

“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 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.
 

“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.

“Oh 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.
 

“Touch 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.