The Merry Widow

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Female peeping Tom spies on a couple shopping lingerie.
3.6k words
4.44
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I like to watch.

As the female owner of a very exclusive lingerie shop in the Village, I am witness to the gamut of lingerie shopping scenarios: Young professional women buying their first good bra. New moms looking to regain their confidence post baby. Older, affluent women who know what they want and don't mind what they spend. These women, I aim to assist with the pure intention of having them leave feeling beautiful and confident.

But for the voyeur -- orvoyeuse -- in me, I enjoy watching couples who come in shopping for sweet nothings, and believing no one is paying attention, get it on in the dressing room. In truth, owning this shop is a hobby for me. I married well, was sadly widowed, and between my inheritance and investments, I never need to work again. My dear husband and I loved lingerie play, and I kept quite the collection for our mutual pleasure -- corsets and merry widows, garters and stockings, peekaboo knickers, you name it.

We made quite the game out of dress-up, usually leading up to me enjoying multiple orgasms and him exploding in my mouth or in my rear, but only after hours of toying with each other. Oh yes, we were hardcore anal lovers. It got to the point where we bypassed "regular" intercourse altogether -- or if we did have regular copulation, it was almost a nostalgic appetizer to the main entrée.

I adored taking his fat cock in my rear, and he often played this fact to his advantage. Sometimes he would tease me mercilessly for an hour or more, licking my pussy and eating out my ass, finger-fuck both my holes while bucking his cock into my face, until I positively begged him to crack my ass open.

I loved how hard he would bugger me, almost violently, until he either shot his load deep in my rectum or pull out to ejaculate between my ass cheeks and then press his warm semen back into my ass with his cock. Stuffing the cream back into the pie, if you will. He was a real artist that way.

Alas, dear husband passed away suddenly, leaving me with a trust fund, a closet full of beautiful sexy underthings, and a valise full of sex toys. At first, I thought I would find someone after the mourning period, but over time and after a few unsatisfactory experiences, I realized I much more enjoyed pleasuring myself and would rather spend my energy facilitating the adornment of the female body for others' benefit.

It seemed a natural step to open a shop offering high-end lingerie, since I was already so familiar with all the makes and with what pleases the eye and feeds the libido. Everything I sell is curated and hand-picked. There is nothing in my shop that you can buy at Bloomingdales. If you are looking for a 3-pack of bikini bottoms or a workout top, you won't find them at my shop, sorry!

If, however, you are looking to thrill your man or lady love, come visit me. People are comfortable with me as a lingerie salesperson. I have somewhat of a soigné librarian look -- early 40s, still slim figure with a full bust, hair usually done up in a twist, stylish glasses, classic heels. They don't need to know I'm representing underneath my clothing and am usually wearing thigh-highs, see-through panty and bra, and -- if I'm in the mood -- a butt plug. Gotta keep life interesting.

+ + +

I take pride in helping bona fide customers get fitted for the perfect undergarment whatever their life stage, but observing new lovers shop for lingerie is one of my favorite pastimes. I make a game of seeming self-effacing, almost dowdy and blending into the surroundings, leaving lovers to shop and, if I'm lucky, pleasure themselves in my shop. I have nothing against it. In fact, pleasure was the catalyst for opening this shop.

Case in point, the other day a man and a woman came in. They entered the shop separately, the woman first, then 5 minutes later the man. They studiously avoided each other's eyes, which can either mean they were hoping to shop alone and were self-conscious, or they were together and pretending not to know each other. She was carrying a Christian Louboutin shopping bag that somehow smacked of a gentleman's gift, so I got the feeling it's the latter.

The woman was in her early 30s, reddish-brown hair below her shoulders, very fair, slight long-limbed figure with perky breasts and a pretty tush (perfect for backdoor action, I immediately think). She was wearing a vintage DVF wrap dress with wedge heels, discreet diamond studs in her ear lobes, and a Cartier tank watch. A little bohemian, and a lot of good taste. I liked her right away.

The man was older, mid-late 40s, on the tall side, lanky cat-like swimmer's build. He looked like a lawyer or a hedge funder (my husband was a banker) with his dark-framed eyeglasses and perfectly tailored English-cut suit that he wears with ease. As he was fingering the delicate merchandise, I noticed his beautiful hands, tastefully accessorized with a vintage Omega watch on one wrist and an old-school ID bracelet on the other -- a look that is stylish yet rakish at the same time. Very appealing, actually. Even made my pussy stir, and I'm usually immune.

After greeting them (separately) and offering my assistance if needed, I busied myself with the oh-so-many daily tasks of running a lingerie store -- you know... folding, adjusting the display, checking inventory against the computer, etc. It was all an act because I know where everything is, and anyway not like I care about keeping inventory, or even about making money.

Anyway, I was enjoying surreptitiously watching these two uptown hotties dance around each other. He flicked through some sheer bodysuits and boned corsets, occasionally pulling one off the rack and turning it this way and that. I had decided they were together so I wondered if he was sending her clues as to what he wanted her to try on.

Meanwhile, she intently perused my bra collection, focusing on the balconette style -- half-cup bras that either leave the nipples exposed or barely covered. She examined them one by one with her well-manicured index finger, like browsing album covers (I know, very Gen X of me). She, too, would pull one out every now and then, turning it this way and that. She also lingered over assorted knickers and thongs. I love all my inventory, but I must commend her on her taste, focusing on items that would look amazing on her. Well, on her tight body, most things would look good.

These two were already turning me on, and I could feel my pussy start to cream. I discreetly observed as she took half a dozen items into a dressing room -- a few things she had looked closely at, as well as some of the items he had pulled out and cleverly put back on the display in an offset way for her to pick up. She stepped into the spacious changing stall -- there are only two, since this being such an exclusive shop, it would be unusual to have more than one or two shoppers at a time. The stall has a bench, wall hooks, a high stool, mirrors on 3 sides, and closes with a draw drape.

I smiled to myself as I noticed she didn't close the drape all the way. From where I'm standing at the register, I couldn't see in, but there's another mirror on the other side of the shop that happened to reflect her perfectly. Like I said, I like to watch. Of course, from where the man was standing, he could see her in the foot-wide space between drape and wall divider. I settled in on my own high stool and waited for the show to begin. For a moment, I considered going to the back room to insert my butt plug, but I didn't want to miss Act One...

+ + +

The woman made a show of undoing the sash to her wrap dress, slowly shrugging it off, and placing it on a hanger on one of the hooks. The bra and panties she had on were quite pretty, actually. Looked like La Perla. Made me wonder if her lover buys her a lot of lingerie and made me wistful for my generous, loving, pervy husband...

She slipped off the wedge sandals she was wearing and pulled out the first item, a boned corset in jet black with matching knickers--a classic. I mentally applauded his choice. Almost like she was lost in thought, she took off her bra, draped it on the hook, then very slowly drew down her panty exposing her Hollywood bare pussy mound, stepped out of it, and hung it on top of the bra. My eyes flicked over to the man. He was watching her from behind a display, his face devoid of expression.

Turning my gaze back to the woman, I watched her pull on the knickers. Most people try on underwear wearing a thong. All the lingerie bottoms have hygiene panels, so I don't mind either way. Obviously, it was sexier that she's trying on the knickers without underwear underneath. Then she donned the corset and slowly, almost dreamily, did up the hooks. Her tits were small and perky, and she looked quite fetching in this corset meant for petite figures. As a full-busted woman myself, I find small-breasted women with sassy nipples incredibly appealing.

Then she rummaged in her shopping bag, took out the shoe box, and pulled out the shoes. They were the legendary black Louboutin peep-toe pumps with spike 5-inch heels and the trademark red-soled bottoms. I was thoroughly impressed. She steadied herself with one hand on the stool to slip them on and drew back up to standing. The knickers set off her ass beautifully, and with the heels on, she was a vision.

I glanced over at the man, and while his face still betrayed no emotion, his eyes looked a little glazed and his lips were slightly parted. I couldn't see his crotch from here, but for sure he was starting to get a hard-on. I certainly was getting turned on!

The woman turned this way and that, checking herself in the mirrors, adjusting the knickers so they offset her pert buttocks better. She would rub a finger on her lips as if checking her lipstick, rearranged her hair, all the classic boudoir poses and gestures. These two were not new to this charade.

Once she seemed satisfied, she started to undo the corset, hook by hook, then put it aside. Then, very slowly, she slid the knickers down her hips and legs, gingerly stepping out of them in her sky-high heels. She offered him a side view of her figure as she does so, showing off the profile her pretty tits and perky ass. A small smile played on his lips.

Then she prepared to test the next outfit. She chose a pair of light blue boy briefs, very low riding and high-cut in the seat, so that one could see the very top of her ass crack and the bottom of her ass cheeks, not to mention her camel toe in front. Beautiful. She had the perfect body for this cut.

She slipped on the matching underwire balconette bra, so low-cut that her perky nipples were showing just above the top rim of the fabric. Stupendous. Again, she swayed a little in front of the mirrors, lightly pinching her nipples to perk them up, adjusting the briefs in the back, etc. The black pumps looked a little heavy with the light-colored ensemble, making her look like a girl trying on her mom's heels. Yet very sexy.

I looked over at the man: His eyes were by then a bit hooded from lust as he licked his lips. I could tell he was fondling his cock, not taking his eyes off her lithe, fuckable body. Myself, I reached for my ultra-quiet vibrator, handily tucked behind the register for occasions such as these. I pulled up my skirt and lazily started to work my clit with the vibe. I was undecided whether to make myself come, but I felt like joining the game.

Moving on, the woman reached behind her back to undo the bra and put it on the bench, then slowly peeled off the booty-hugging briefs, turning her back to his view as she did so. I could almost hear him hiss in his breath as he took in the reveal of her bare ass, slightly up-tilted since she was in in her stilettos. He blinked his eyes slowly one time, like a lizard. I know that look well. It was clear he's an ass man.

She reached for the last ensemble she will try on today, a pair of peekaboo panties in deep scarlet, and matching cut-out bra. Very slutty, yet very beautiful. A superb choice. These items are very cleverly cut and belie their main feature. Each of the bra cups are made of two panels of lace that to provide ostensible coverage. But with just two fingertips, one can separate the panels of each to enjoy nipple play. The same concept applies to the panty in the front, while the back has a large keyhole opening for easy access.

Feeling like the man may finally make a move, I made sure to be looking down -- as it happened, at my own pretty crotch as I was playing with it. As I expected, the man quickly flicked his eyes my way and seeing me otherwise occupied, made his way into the stall. He neglected to draw the curtain.

I watched in the far mirror as he grabbed her hair and kissed her deeply, his hips pressing her pelvis onto his. In her heels, she was a good match for his height. She reached down with one hand and massaged his crotch, her other arm wrapped tightly behind his neck, returning the fervor of his kiss.

He pulled away from her lips and with the two fingers of one hand, he parted the panels of a bra cup to find her nipple with his tongue. His other hand was on her ass, no doubt caressing her bum cleft through the keyhole opening. She arched her body against his, reveling in the attention. He made sure to lavish his tonguing on her other nipple as well.

She leaned one hand on the high stool right next to her as he traveled down her body, went on one knee, and worked his tongue between the two fabric panels of the panty front, licking her bare mound and cunt.

He doffed his suit jacket and threw it carelessly on the bench as he went to town on her pussy. Conveniently he was wearing suspenders, making it easy for him to unzip and draw out his cock without dropping his pants. He rolled up his sleeves and commenced pulling on his cock as he voraciously dove into her crotch. I could see from here that he's impressively hung. She had her fingers intertwined in his hair as she pulled his face into her mound. Her legs looked like they might buckle, and I fleetingly worried she would topple over.

He stood back up, steadying her, and gave her another deep kiss. I envied them that they could both savor her aroma. Reminded me of when I would share the taste of my own juices with my husband.

Then, the moment of truth, he motioned for her to turn around. She did so and propped her elbows on the high stool. How thoughtful of me to have placed it there!

He kissed her gently down her back as his fingers stroked her love box from the back. He then crouched back down and started to lick out her ass through the keyhole opening. How I wished I could see them up close. I love the act of anal rimming -- receiving it and also looking at girls receiving it in porn. I'd bet her fully waxed ass hole would be very pretty and very tasty. He was pulling hard on his cock again. I prayed he wouldn't do it too hard and orgasm by accident. I definitely wanted to see these two fuck.

The woman reached into her bag for something, found it, and brought it to her pussy mound. I smiled, recognizing a kindred spirit, a woman who travels with her vibrator. She worked her clit as he ate out her ass. I can tell he is rimming her with purpose now, just as she was working her clit with purpose. She shimmied her hips up and down as she rode her vibe with his tongue on her ass. She must have been very turned on because I could see her already starting to move faster, apparently ready to cum.

She had one forearm on the high stool now, and bowing her head on her arm, her orgasm arrived. From where I am, I could hear her moan. "Oh god, Marc, oh my god, I'm coming... I love when you tongue my ass, fuck!" She bucked hard, and I could just imagine her little pucker quivering around the man's tongue.

+ + +

As he was softly lapping at her rear in her afterglow, I decided that was the moment to nip to the back room and get my butt plug with the built-in vibe. It took a moment for me to retrieve it, lube it, and slip into my ass, enjoying the full feeling of my anal canal hugging around the toy. I didn't turn the vibe on just yet, though. I willed myself to wait for the right moment.

When I regained my perch and returned to watching them in the far mirror, the man was already plowing his cock into the woman's pussy from behind, the red panty pulled half way down her thighs. She was quite a sight to behold, crimped at the waist over the high stool, offering her pale buttocks to him. Delicious.

As he sawed in and out of her pussy, she reached again for her handbag which was right next to her on the bench. She fished out something small and handed it to him. He took it and mimed flipping open a squeeze bottle. I couldn't see from where I was, but it had to be lube.

He slowed down his hips and with his cock still inside her, he slathered a quantity of lube onto her ass crack. Then he pulled out and palmed some more lube all over his pussy-primed cock. If I were a more conscientious shopkeeper, I would have been concerned with them sullying the expensive merchandise, but I was too busy working my own clit with my vibrator.

He lined up his cock with her anus and slowly yet firmly pushed in. She held her ground and pushed back to meet him. Right at that moment, I switched on the vibe in my ass. My pussy was creaming like crazy and I could come anytime, but I decided I will climax when he did.

The man pumped in and out a few times with the woman practically doubled over the high stool, holding on to the legs just below the seat. She was still tottering on her high heels which helped keep her ass at the right height to meet his thrusts.

After several pumps, I observed that he is already completely in, the fabric of his open fly abutting her ass cheeks. Clearly, they are anal experts. His hands were on her side waist, and he was bucking rhythmically, sometimes fucking her tight ring with his cock head, sometimes working the full length of his cock in and out of her tightest hole.

After some minutes, he started speeding up, as was I with the intensity of my vibrator, getting close to his (our) climax. I had reached back and was fucking my ass with the vibrating plug, as my other hand vigorously worked my clit with the vibrator. It didn't take long until my climax arrived and I came hard, just as I heard the man groan:

"Oh fuck, Lizzie, your ass hole feels so fucking good. Fuuccckkk, you're gonna make me blow my load, aaaaahhhhhhh..." He came hard with his face buried in her neck. She tweaked her nipples through the bra cup slits and moaned along, sluttily shimmying her rear onto his cock, engulfing his cock with her ass. He was still gently bucking his hips into hers for a full minute after he came. I'd bet her ass is very snug and difficult to leave.

His cock still inside her, he lovingly stroked her body from behind -- her breasts, rib cage, waist, hips, thighs. He planted lazy kisses on the back of her neck and shoulders. He gazed into the mirror in front of them and caught the reflection of me in the far mirror and gave me a mischievous wink. He was wise to me all along!

I threw my head back and laughed a silent laugh. How delightful! Perverted minds think alike. The woman was still bowed forward, oblivious to our wordless exchange (or who knows, this may be their M.O.) He drew a circle with his finger indicating all the merch she had tried on and motioned the international gesture "Check, please." With a contented smile, I put away my toys, readjusted my clothing, and prepared his invoice.

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4 Comments
BetaCaseyBetaCasey11 months ago

This was such a hot story. As a voyeur and masturbator myself I really connected with the main character

AnonymousAnonymousabout 1 year ago

Beautiful, excellent fantasy tale, my wife and I once had an experience in a small lingerie store, I sat outside the fitting room while my wife was fitted for a bra and "helped" with several pieces of lingerie, the lady of the store finger fucked my straight wife and made her come twice, one of our favourite remeniscenses

MacScott_MacScott_over 4 years ago
So good!!

As always, such great pacing and style and a perfect build up. Love the main character and absolutely adore the set up. Way to reel us in, scribe. Your voice continues to impress and immerse.

WatcherRobWatcherRobalmost 5 years ago
Interesting - butt

This would have been a high rated story without the anal shenanigans.

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