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Double Penetration

Aargh! My tablet just blew up with calendar reminders. I love my work, but lately it’s been overwhelming. I have been a corporate attorney for nearly 25 years and also sit on several non-profit boards of directors. While I get to do pretty much what I went to school for and trained to do, the lifestyle doesn’t leave much—or any—room for a personal life. I’ve had a few long-term relationships, but I am drawn to strong women who are as dedicated to their work as I am, and sooner or later, with opposing schedules we would drift apart or someone has to move away for work. I’m from SoCal and was a swimmer all through college and law school. Now I live in Manhattan and try to carve out time to do laps several times a week, but even that goal is getting harder to maintain. It’s one of the best ways for me to de-stress, though.

The other way to de-stress is to spend several hours tending to a beautiful woman, preferably one with a taste for kink. This is hard to find. A grown woman who knows her mind, has traveled widely, can navigate a wine list, enjoys work whether for a company or for herself, but also has the confidence to role-play and let herself be taken care of, aka be “the girl.” I love nothing more than a woman who can be a shark in the boardroom, but who also is the kind of feminist who takes power in sexy dress-up and will lie back—or bend over—and let me do just about anything that comes to mind. I love to lavish gifts on the woman I’m with—lingerie, designer heels, the odd piece of body jewelry. I make good money but don’t have much time to spend it. I have the nice loft in Chelsea that I spend barely any time in. I get good suits tailor-made because, well, it’s easier to call my trusty tailor and order a new one than go to a store to shave off a couple hundred bucks and be stuck with a potentially ill-fitting suit. Same thing with shoes; I basically reorder similar ones I’ve worn in the past. I do have a nice watch my father handed down to me that I actually care about, an Omega. And my only other accessory is a 70s style ID bracelet that my first meaningful girlfriend gifted me in college. It was already retro at the time she gave it to me, but she was into retro and I was into her. Way into her, in more ways than one. Anyway, long-winded way of saying that after investments, I enjoy spending money on very specific gifts for my lover. I guess you could say I’m old school with a modern twist.

My most recent paramour is a perfect example of my ideal woman. Accomplished, beautiful, kind. And in the bedroom, my God. She could Hoover cock like pro and loved it. And while she adored getting her box licked and thoroughly enjoyed “regular” penetration, it was always foreplay to her favorite end goal: getting pegged hard in her ass, with my fingers in her mouth and my other hand strumming her pussy and clit. It was often a game how long I would make her wait before I transitioned my ministrations from her pussy to her ass. Usually she would be a quivering mess and already be so ready to come. Sometimes I’ll make her come right away with my mouth and fingers, especially when I know we have the whole night (or day) ahead of us and have time to go again and again. And sometimes I make her wait and bring her to the brink several times and back again until we’re ready to blow our wad together. And of course, there were those times we come back from dinner so horny after making out in the cab and just start fucking with our clothes on in the kitchen.

She loved to role play, and we had many favored scenarios. The ‘walking in on her while she’s getting dressed’ bit. The ‘stranger in the bookstore’ act while she’s perusing erotica, leading to a greasy fuck in the lav. Then there was the Peeping Tom act while she’s shaving her pussy and ass, which usually ends in an explosive masturbation session, often with me literally bringing in the rear, shaving cream and all. There were many more, but that last one is top of mind as I lie here on my office sofa rubbing my cock through my trousers after hours.

If my ex-lover were here, she would immediately drop to her knees and start working on my cock with her greedy mouth while fingering herself. Sometimes she blows me so hard, her eyes start to tear up and her makeup runs a bit. To gaze at a beautiful, expensively dressed woman wearing sky-high heels, on her knees with her lips wrapped around your cock and her hand between her legs, while her mask to the world is smudged by passion is indeed a sight to behold. I complete this tableau by reaching out to pinch the fabric of her skirt over her hip and fondling her bum cheeks. I snuggle my middle finger in the cleft of her ass and massage her anus through the thin fabric of her knickers.

After a good quarter hour of these gymnastics, she would stand up, undo and take off her dress, then pause for me to appraise her. She favors brief-cut knickers—no thong here—which is mid-rise, lacy, and nearly transparent. A retro look that’s reminiscent of granny kurtköy escort pants, yet decidedly not granny pants. Likewise, her bra is an underwire half-cup balconette style that barely covers her nipples and set off her breasts beautifully. That day she might have on thigh-high fishnets; she never wears full tights. She claims they make her too hot. She’s hot, all right. And she’s still in in her peep-toe Louboutin pumps with the trademark red soles that I had gotten for her. I sit up on the sofa and hold up my arms in an invitation. She comes closer and I grab on to her hips to bury my face in her crotch. Sweet Lord, what a wonderful aroma. The combination of a wet pussy, light waft of the day’s perspiration, with a faint echo of perfume or body wash. My cock instantly weeps up a fresh bead of precum.

I reach around to squeeze her ass as I gnaw on her mound right through her underwear. She bends one knee and places a high-heeled foot on my expensive couch, being mindful not to mar the fabric with her stiletto. I spy the gleam of her dark red toenail varnish through the small front opening of the peep toe, through her fishnet. I wouldn’t say I have a fetish exactly, but my favorite body part—my Kryptonite—is the ensemble of a woman’s legs, feet, and ass. I don’t think I’ve ever told her this outright, but she knows it and always displays them to their best advantage. With her one leg up, I have better access and stretch my tongue to the skin where the panty ends and the flesh between her pussy and legs meet. With one finger, I peel the fabric on one side slightly back so that I can lick the pillowy edge of her smooth outer labia. She tugs on a handful of my hair and lets out a soft sigh. I repeat this with the fabric on the other side, so that for a moment it’s like she has a reverse wedgie, where the wedgie is between her front pussy lips instead of in her ass (that’s for another time). This also has the effect of applying pressure to her clitoris thereby enhancing the sensation. She is all wet around this pussy wedgie. I lap at her mound like this for a little while before teasing the first knuckle of two fingers into her eager pussy.

We are lost in this rhythmic movement until I abruptly lift my head and rearrange her knickers to cover her pussy. I guide her to turn around so that her ass clad in the see-through undie is right in my face. I press my nose into the silky fabric and take a deep inhale. The combined scent of her ass, girl sweat, and arousal made my head spin, my mouth go dry, and my cock spring to full attention. Reader, know that my lady is a meticulous groomer and very fastidious. Her ass is clean yet smells of a musk from everyday activities like rushing for the subway, sitting for long periods at her desk, etc. I also know her pussy is wet most of day, since she tells me she often replays our latest escapade in her mind while at work. So you can imagine the sweet, delectable scent I am inhaling right now. I ache to taste and coat my tongue with it. The head of my cock is now glistening from the precum that has been seeping. It’s been a long moment since she took her mouth off my cock, so the precum is collecting, waiting.

With my nose and jaw still tightly pressed into the cleft of her fragrant backside, I start to massage small circles with my thumbs along the edge of her underwear and ever so slowly begin to insinuate my thumbs underneath the fabric and towards her sopping pussy. I continue to nuzzle my nose slightly up and down her ass crack, with the thin fabric of the knickers still between us. Then I take one hand to peel down the top edge of her panty halfway down her ass. I inserted the thumb of my other hand into her pussy and at the very same time, rasped my pointed tongue from her brown wink to the top of her ass cleft. She slumps forward slightly and lets out a small sob. Luckily a lamp stand was nearby so she was able to steady herself. She reaches one hand back and held a cheek open so I can admire her crinkly anus in the lamp light. The other cheek is held open with my panty-lowering hand, and I set to tongue-lashing her in earnest. I swirled my tongue all around her backside, her goose-fleshed buttocks, the papery thin skin surrounding her anal area, and of course, the rubbery anus itself. I love the sensation of stabbing my tongue into her anus and having the ring squeeze my tongue. Likewise, when I withdraw my tongue, the ring hugs around my tongue like it doesn’t want to let go, but then does. In and out. Squeeze and release. Sometimes I alternate by thumb-fucking her ass while I lean down to lick and suck her pussy. I can’t get to her clit, but she’s covering that just fine. I could have continued doing this for a very long time. There are few things more bewitching than a woman offering her female charms to me this way. Nirvana.

I’m watchful of the tempo of her machinations on her clit, wanting to make sure I’m inside her when she comes. I love to feel her insides pump my cock while she’s orgasming. malatya escort I put both hands on her hips and without even looking at me, she understands my wish. She slows down her pace as I stand up and line up my cock with her pleasure center. At 5’8″ in five-inch heels, she’s a good match for my 6’2″ frame. I pull her knickers down below her ass cheeks now and quickly guide my drooling cock into her cunt in one movement. There’s a sense of urgency in both of us as I start to piston my cock into her like it’s the last thing I’ll ever do. She leans more forward over the piece of furniture and gives in to the assault. This also makes it easier for her to play with herself. Her handbag is within reach (knowing her, she probably planned it) and even with eyes closed, she easily finds her travel vibrator and clicks it onto its highest speed and starts furiously working on her clit.

I can feel the rising hint in my balls and know my orgasm is not far off. I gob some spit into my hand and swab it onto her asshole. I repeat this a few times more to maximize the makeshift lubrication by finger-rimming her anus with my saliva. Meanwhile I can tell by the concentration on her face that she is also close. I pop out my cock head and slowly stuff it into her ass hole. She wants it, but it’s still a tight fit and takes a moment. She gyrates her hips to facilitate insertion. It’s not my goal to have my entire cock in her rectum anyway; there’s simply not enough time. I’m fucking her ass with just my cockhead. The moment her anus wraps around the bottom rim of the mushroom head on my way in, I start to withdraw in order to repeat. We’ve done this countless times, but every time I am still mesmerized by the sight of her anus dilating and then reflexively squeezing closed.

I’m striving to coordinate with her rhythm and once I’m pretty sure she’s on the same timing, I let me myself go and allow my jizz to erupt. She’s coming too, so I pull out mid spurt such that some of the thick substance ended up just inside her ass and the rest jets onto her anus as it’s clenching and re-clenching from her intense orgasm. Once I’m spent, I use my semi-hard cock to gently press some of my semen into her well-loved asshole, still slightly pulsing. It’s our version of the cream pie. Stuffing the pie after the fact, if you will. So beautiful. So nasty. My girl is bent over still in her stilettos, knickers down, cum on her ass, moisture dripping down her inner thighs. Her posh façade now a spectacular ruin. I lean down for a deep kiss as she coos her appreciation and rubs her ass in my crotch.

Well, that’s one way it could have gone down if she had been here. But sadly, she was also very successful in her work and was seconded to Amsterdam a few months ago. We spent an entire weekend bidding our farewell, doing everything we liked with each other as if for the first time, because it was likely for the last time. I’m sure she’s keeping busy with some lucky Dutchman now. And here’s me, rubbing my cock through my pants on a Thursday night.

…Funny thing is, I took a break from work tonight to relax a moment and ponder someone who just came into my peripheral vision. My law firm has several offices across the country. I’m a partner based in New York, but our Operations is based in Chicago. Our head of communications there travels several times per year to all the offices to meet with the partners and stakeholders. Lizzie is younger than me, 32? Hard to tell these days, and any way, who cares? We’ll all live to 90 and run out of retirement money. But I digress. She’s very nice but doesn’t overdo with the niceties, which I appreciate. Very good at what she does, and everyone likes her. The assistants like her. The partners and associates respect her. It’s all good. I don’t look around at work to hook up with anyone. For a partner, it’s a huge no-no. So suffice to say, she was not on my radar at all. She was just an affable coworker that I am happy to collaborate with because she is very efficient and effective.

This was until the most recent trip she made to HQ. Three almost imperceptible revelations conspired to turn my head, and now I can’t stop thinking about her. I mean, seriously, she’s very easy on the eyes but not in a way that makes you do a double-take. She wears glasses which automatically lend a professional air. But everyone wears glasses here, myself included. Her figure is nice enough; more a straight figure, small chest, slim hips. Just like countless young women who do yoga or Pilates these days. She does have a quick stride which I like. She’s patient at work, but her stride implies a certain impetuousness. And up to now, the only thing that might have made me linger my gaze are her beautifully pedicured feet which are on display in summer when all women everywhere are sporting open-toed shoes. So again, not that specific to her. Beautiful toes though, a high arch, slim ankles. Hmmm. But no, I don’t date at work.

Anyway, this winter we were all finishing kayseri escort up a meeting, and when she got up to walk out, I swear I could detect the telltale ridge of stocking top beneath the clingy fabric of her dress. Not clingy because she was wearing a sexy outfit to work, but due to a bit of static. It was fleeting because her skirt fell back in place so most people wouldn’t have noticed, but I am a connoisseur of open-top stockings and know the hallmarks well. She also happened to be wearing a higher-heeled shoe than her usual boots, and the combined effect of the suspected thigh-high or garter, the tantalizing leg line tapering to the slim ankles and—because they are covered with hosiery so I have to imagine—the beautiful feet I had seen back in summer. I felt a twitch in my cock, and like a cartoon character, I gave my head a light shake and blinked away the vision. Huh, maybe I do have a fetish. I’m just admitting to that now at 49 years old.

Later that week, we were in another long meeting and something was off with the HVAC so the office was really hot. Lizzie took off her blazer at one point and spent the rest of the time in her sleeveless silk top. She is always well-dressed, hence the top was quite stylish even if it did show more skin than usual for her. Hell, we all wished we were in T-shirts. At one point in the afternoon though, I noticed her bra strap peeking out from the back armhole of her top. This is hardly noteworthy, except that I recognized the strap because I have purchased a brassiere of this particular exclusive brand for a lover and have lowered the straps off her shoulders many times. It is a beautiful garment that covers everything yet conceals nothing. The mark is Agent Provocateur and is very expensive. As in, you can take a short flight somewhere for what this bra costs. An accessory meant to be admired and taken off by eager fingers, or kept on during illicit acts… And my dear colleague is wearing it to work! This woman either has a lover who lavishes gifts on her as I would, or she really pampers herself. Both possibilities are appealing, although I did find myself feeling envious of such a lover. Rather disconcerting because not 3 days ago, I only ever appreciated her pedicure.

These two occurrences by themselves were titillating but actually not earth-shattering. Sneak peeks of women’s undergarments? Come on. It could also be I’m so overstretched with work and other commitments that I am projecting. But at the end of this same day, a new detail was revealed which was not ambiguous, and I’m certain I didn’t imagine it. Again it was after the meeting, and Lizzie was bending over to pick up her laptop case. I think she forgot she wasn’t wearing her blazer, and as she bent over, her top rode up a bit in back, I could clearly see the glint of metal from a whisper-thin belly chain just above her waistband. The clasp of the chain was just above where the dimples of her low back would be, not visible because of the waistband, and the end of chain trailed down out of view, towards her crack presumably.

The chain in itself was a turn-on enough, but I know that such a dangling chain could have a butt plug attached to it. Seeing that made me a bit weak in the knees, and thank Christ I was already sitting down so that I didn’t have to cover my growing hard-on. I go crazy for body jewelry on a woman. Body chain, belly chain, clit studs, you name it. I love when a woman doesn’t seem to be wearing much jewelry until the clothes come off and you discover her assets are strategically adorned. And to that point, Lizzie always wears just her Cartier watch, eyeglasses, earrings. No rings or other accessory, minimal makeup. But clearly, her accoutrements are not for the casual gaze: the thigh-highs, the high-end lingerie, the belly chain with potential sidecar. How can she just walk around like that, cool as a cucumber?! And was this slow reveal for my benefit, or dumb luck??

Somehow I make it back to the office without anyone noticing the bulge in my pants. An imagined scenario was forming in the back of my mind: lifting Lizzie onto my desk and eating her out with her stockinged legs slung over my shoulders while she tweaks her nipple underneath her fancy bra and rubs her clit. She keeps her eyeglasses on, but her eyes are closed and her head thrown back. Her belly chain twinkles right above my eyes, the end of it behind her and looping forward disappearing into her asshole, anchored by a plug. The librarian-gone-wild stereotype on steroids.

Absent-mindedly fondling my cock while pondering if she would have a trimmed pussy and ass—in my experience, women who adorn their body also go bare—I checked my email and see a message from the administrative manager: “Dear staff: Please mark your calendars for an all-hands 3-day off-site coming up in Napa Valley. While we hope you will have ample opportunity to get to know your colleagues from across offices better, it’s not all play and pretend work. We have team sessions planned, with the preassigned teams detailed below. Dress code is resort casual. Work hard, enjoy the facilities, and have fun!” I scan the email further and see that Lizzie and I are on a few breakout teams together.

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