P is for Pegging (The Fantasy A-Z Series) (2 page)

 
“Definitely, 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.
 

“I’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.
 

“Speaking 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. “What, Dan, what is it?”
 

I pause and shuffle my feet, wondering about the best way to say what I need to say.
 

“Well 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.
 

“But. . .” She urged me on.
 

“Well 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.”

“Haven’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.
 

“Yes, you’ve been amazing and so I am hopeful you will have an open mind to what I am about to say.”
 

“Try me.” Laura said, shivering a bit against the wind and looking bored with the conversation.

“Ok 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.
 

“Wow.” Laura was laughing, but kindly. She grabbed my hand, and the contact feels reassuring. “I 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.
 

“So you aren’t freaked out?” I ask, a bit shell shocked at her response.

“Not 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.
 

“Wow, you really are amazing. Thanks for being so open minded. Other girls I have asked have been totally freaked out.”

“I 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. “Easy 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 “You 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.
 

“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, 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.
 

“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.