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

  ***

  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.

  “You 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.

  “Thanks 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 “Make 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. “Hey 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. “Hey, 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 “I’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.

  “I don’t think that is where it is meant to go, honey” I say, smiling at her playful enthusiasm.

  “Actually, 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. “Hey, I’m Jack, did you all need any shopping assistance today?”

  Before I could stammer a firm “No thanks,” Laura has extended her hand and is shaking Jack’s enthusiastically. “Hi Jack!” she says, still holding on to me with her other arm. “We 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. “Goes 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. “Most 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 “It 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.

  “What 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. “That’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, beau
tiful 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.

  “You 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. “See you guys soon. Have fun and stay safe!” she says, smiling at Laura in particular.

  “Oh 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. “God 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.

  “Are 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.

  “A 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, “her 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.

  “Cheers to new adventures together!” she says, raising her glass and looking me right in the eyes.

  “Cheers!” I echo, clinking glasses. I take a deep long pull on the tequila, enjoying the rush of heat down my throat.

  “Now, 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.

  “Uh, yeah, of course.” I manage to mutter.

  “We’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.

  “Anything else you want to say?” Laura asks, knocking back the last of her tequila.

  “Just 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.

  “You are so welcome. Now, you have no plans tomorrow, right?”

  “None, I cleared the weekend for you as requested!”

  “Great, 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. “I’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 “Instructions: 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.

  “Come in!” she calls and I push the door open. Warm air rushes towards me, and I notice she has been running a sp
ace 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.