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Sherry and the Stripper

Sherry took a deep breath. She wasn’t ready for this. How could she be? Nothing she had experienced before had prepared her. Why was she doing this? Would she regret it? Would Harry? Every last minute doubt possible was confusing her, frightening her.

Another deep breath. It was time to go. One more glance in the full-length mirror in her bedroom. She looked just as Michael had asked. Pink blouse, low, low cut. Charcoal skirt not tight around her ass and legs, 4 inches above the knee. Garter belt holding hose high, high up her thighs. Hose as tan as her shapely legs, almost invisible, so erotic, so seductive.

On her right leg, Sherry wore a gold anklet purchased at her request by her husband Harry. It was a symbol to those in the know of a “hot wife.” Under her skirt, pink thong panties to match her pink bra. Never had she considered wearing a thong, but as she slid them up her silky, waxed smooth legs, she felt a slow throb in her clittoral region.

Michael would never see the underwear, but Sherry felt obligated to wear it just the same. The knowing it was there, knowing he knew it was there made it soooo erotic. Her only concern was whether it would hold back the building flood.

Harry was already in the car as she walked out of the house. The short skirt rustled against her legs as she walked, caressing them. It felt good, really good. As she slid onto the leather passenger’s seat, Harry watched her legs as they spread apart when she entered, watched the skirt ride high when she sat down, then lower again when she brushed the hem down.

Sherry’s husband moved his hand to her thigh and tried to stroke upward. She caught it and said, “Not for you.” She smiled, but her grip was firm and Harry removed his hand.

“Well,” said Harry, “this guy really knows how to establish an exciting scene. Then they rode to the hotel in silence, listening to radio, lost in thoughts of their own. Each re-living a private fantasy for the last time before it finally collided with reality.

Five years ago Sherry turned forty and a confluence of events began leading to her journey to the hotel, and farther. Her only child, Jason had left for the Navy, she took her first job outside the home since she was nineteen, and her husband Harold, Harry, received the promotion he’d worked his entire career for.

Perhaps the promotion was too much for him; perhaps he’d reached his level of incompetence. Before that could be established conclusively though, Harry launched himself into a workaholic’s schedule to prove himself.

All this left Sherry with new friends and far fewer family commitments. The first seed was planted about eighteen months after she began work. One of the women she’d become friends with suggested a girls’ night out – to a strip club.

Sherry was mortified. She only agreed to go because she was determined not be thought a prude. The show proved more an embarrassment to her than anything else. She was simply uncomfortable in that blatantly sexual environment with people she knew.

What she observed in the other women attending the show was an eye opener. Many were shy, but others definitely were not, grabbing forbidden fruit, stuffing money into tiny costumes. She heard two strangers next to her discussing one dancer.

“Mmmmm, he could do me anytime.”

“Yeah, but I heard they charge you $100 just to blow them.”

“God no! Who’d ever pay to do that?”

“You’d be surprised, I guess. I heard they get more offers than they can handle.”

“To pay them to suck their cocks? You can’t be serious! Would you ever do that?”

“Who knows, some of them look so damn hot, I really want rip off that little g-string.”

“Jesus, Lillian, now you’ve got me thinking about it.”

At one point, a blond stud moved in front of Sherry and rotated his sequined sack just inches from her face. She was so embarrassed, she covered her eyes with her hand. The crowd hooted and the dancer moved to the women next to her where he was much more welcome.

Sherry relived the night at the strip club often in the months following the event. The night out took on a different dimension as Sherry went over it in great detail in her mind.

She wasn’t nearly the shy embarrassed housewife in her fantasies as she was at the club. At first the fantasies stayed close to the events of the night as she masturbated to orgasm after orgasm. When her need grew, the dancer did more than the club permitted.

He pulled his g-string aside and showed Sherry a lovely semi-erect cock. Already bigger than Harry’s, it grew impressively as he stroked himself while looking directly into Sherry’s eyes. Eventually, her imagination required that he stroke himself to an explosive climax as part of her self-pleasure ritual.

As the dancer’s cum arced high into the air, Sherry would also shudder and thrash about with her finger on her clit and her thighs clamped tightly around her hand. The conversation of the two unknown women was sometimes playing in the background of her fantasy, but was never required to reach the draining relief she needed.

Sherry had told Harry about the night at the club and he seemed far more interested than she thought he’d be. He asked about the dancers, which ones she liked, what they did, did it excite her? Her answers were honest, but she kept them low key. Harry often proved more ardent if they discussed that night of near naked men before they engaged in sex, but overall, the stresses of his job were preventing him from adequately seeing to her needs.

About a year after the night at the club, Sherry had the occasion to be at a bachelorette party where the bridesmaids had secured a male stripper. He was not as attractive or talented as the touring professionals at the club, but several drinks caused both his dancing and his looks to improve significantly.

Despite her moderate inebriation, Sherry maintained a demure posture even as the dancer provided added fuel for future fantasy sessions. Indeed, he stripped completely, removing his g-string to reveal a fully erect penis. He was not as large as her fantasy man, but he was very real, and imagination could make the necessary adjustments when the time came.

The highlight of the party came when a pretty bridesmaid who’d had one too many, wobbled over and knelt before that naked dancer, engulfing his organ and fellating him till everyone present knew he delivered his load. When he stopped twitching, the young woman let his cock slip from her mouth, grabbed a glass of Champaign from one of the onlookers, and washed down her reward.

The image of that oral session proved a potent one for Sherry. Her orgasms became more intense and her need more frequent. In her free time, she’d taken to reading some of the personal ads in the city paper. She had no intent of answering one, but found that sometimes one would hint at something that would fuel a fantasy.

About this time, Sherry discovered the Internet. At first, she browsed on-line merchandise, researched some recipes, her family name, things like that. At some point, her surfing brought her to a personals web site. After a few sessions in the personals, she discovered the adult ads. At first she resisted spending time there, but her curiosity kept drawing her back. It was a few months later that she discovered Michael’s ad.

Handsome personal fitness instructor, 26, 6 feet, 190 pounds, 9 inches. Graduate degree in nutrition and health. Interested in stripping for voluptuous women, 40-55. Masturbating to climax will be part of the show. Will deliver facial or tit shot if desired. Husband may not watch. Intercourse is not available. Fellatio considered if exceptionally pretty. Michael

Sherry returned again and again to the ad. Soon, she knew it by heart. Why did it speak to her on such a personal level? She dissected every line, every nuance. Fitness instructor equals hunk. Graduate degree equals smart. Nine inches equals stud. He wants older women, voluptuous women, not someone scrawny or malnourished.

Masturbate to climax. At first she always lost it at that point. He’d jerk himself off while she watched? The thought caused an immediate orgasm in her. If she thought about it at work, she’d have to go to the ladies room to relieve herself. Nine-inch cock, his hand stroking, body stiffens, a moan, oh god, here it comes, great spurts arcing through the air, splattering onto her face, her tits. She could continue no further.

Sherry had told her husband all about the bachelorette party stripper. She’d noticed how interested he was in what happened and particularly in how that made her feel.

She’d begun to tease Harry to get him to perform, telling him how watching the stripper caused her to become wet, hot. How she sometimes masturbated when she thought about him jerking himself off. She saw how it aroused Harry. She began to wonder if she might go further. Could she actually act on her fantasies?

After about a month, Sherry sent a reply to Michael’s ad. They corresponded via email and Sherry asked him about himself. Michael sent several pictures. A couple of him clothed. Yes, he was exceptionally handsome. One of a large, hard cock with a hand around it, but no face to verify its owner. Several others of himself posing in a Speedo bikini that showed an incredible body and a very significant bulge.

Later he sent a series of shots showing a man lowering his trousers, stroking from base to tip, and finally, five different large spurts as each left the end of his cock. In several pictures in this series a woman can be seen from behind as she knelt close to the masturbator. The final shot is of her hand as it caresses the spent, but still erect organ and its residual jism.

These pictures sent Sherry into a whole new orbit. One in which she knew she must initiate the next step, an actual meeting with Michael.

One Saturday, after some wine, Sherry began to tease her husband. She spoke of how horny the strippers had gotten her, how she would have really liked to touch their cocks.

Harry played right into her game, becoming excited, asking if she’d actually touched them and had been afraid to tell him. How he’d be ok with it if she had. Actually, it kind of turned him on to think Sherry might touch another cock and get excited. Sherry knew it was time to move in for the kill.

“Actually, I’ve been thinking about having a private session with a stripper. Just me, nobody else. I’d like to do some things like touch him and I couldn’t have friends watching me do that. What do you think?”

The truth was all this really excited Harry. Having his wife speak openly of strong sexual desires had rekindled something of his fading libido. He was all ears, but he started slowly.

“No way you’d ever do that.” Harry didn’t believe his wife was actually capable of doing something like she’d described but, if he put things in the form of a dare, maybe Sherry would rise to his challenge.

“You’d be surprised,” she mocked. “I’d be a little nervous, but if you really want me to, I would do it.”

“Well how would we…who would…”

“I’ve already located the man.”

Harry was completely taken aback. “What?” was all he could stammer.

“Let me explain.” Sherry told him about Michael and how she’d like to meet him and that she believed he’d meet with her. She explained her plan to meet Michael at the bar of a nearby hotel where she’d also have taken a room. If everything checked out, they’d go to the room where the strip would take place.

“But what would I be doing while you were in the room with him?”

“You could stay at the bar till I return, then we could go back to the room together.”

“What if he tried something in the room? Something more than stripping, you know. What if he wanted more than just jerking himself off? Maybe I should be in the room with you.”

“He’s said he won’t go for that. Maybe you could hide in the closet.”

“Well, I don’t know about that.”

“Then you’d have to stay in the bar. I’m not even sure I should introduce you to him. He might not like that. It could spoil everything.” Sherry knew full well what she was implying. That her husband would have to be subservient, that he would have to accept the conditions of another man whom his wife intended to have a sexual liaison with.

Harry backpedaled. “Well, let’s wait and see the room first. Maybe the closet will be all right, or I could stay at the bar

My, aren’t you docile? thought Sherry.

* * * *

Now, as they waited in the hotel bar, Sherry thought about the things she hadn’t told Harry. One she knew he’d discover under any circumstances, and another one she wasn’t sure about. However, after their trip to the room and Harry’s declaration that he would hide in the closet and watch, both would become known.

Sherry was not deliberately withholding the information, it was just that she didn’t know what Harry’s reaction would be, and since she was sure she wanted to go through with this, she decided to just let things happen rather than risk blowing up the deal ahead of time. As she looked across the room, Sherry knew the first discovery was upon them.

The young man striding across the bar looked just like his photographs, lithe and handsome. His clothing covered a body to die for. Sherry started juicing badly and worried again about her skimpy thong panties. She wanted to get to the room as quickly as possible. As she rose, Harry’s jaw dropped.

“You must be Michael,” Sherry said, holding out her hand like she was meeting a business professional.

“You must be Sherry,” Michael replied, leaning forward and kissing Sherry on the cheek. “And you must be Harry. From the look on your face, I assume Sherry didn’t mention I was black.”

Harry was speechless. Sherry told Michael they’d be right back. She led Harry several steps away and asked if everything was okay.

“Jesus, Sherry, this is a shock. You could have said something.”

“Look, I’m going through with this and you can deal with it later, but right now, I’m going to see what I came to see. Are you going up to the room or not?”


Harry left for his hiding place in the closet while his wife walked back to the young black man alone. She told Michael she needed a drink first before they went up to the room. She told him Harry had come to ensure her safety, and now that things looked fine, he’d rejoin her later.

Sherry and Michael enjoyed a drink while Harry carefully ensconced himself in the darkened closet. The door was only open a crack, and he couldn’t see the whole room.

Several minutes later, Sherry and Michael entered the room. Michael asked Sherry to sit in the chair Harry had positioned so he could observe his wife’s reaction even if he couldn’t watch Michael.

Sherry sat down and crossed her legs. She deliberately hiked up her hem, just the opposite of when she’d sat in the car with Harry. Sherry’s husband could hear some low, slow music.

Michael was dressed in a navy blue sport jacket, white shirt and charcoal slacks. He really didn’t do much of a strip tease. First he took off the jacket and laid it across the bed. Then he deliberately unbuttoned his shirt and pulled the tails out of his pants.

Sherry became agitated and excited as she watched Michael remove his shirt just two feet from her. She crossed and re-crossed her legs, finally leaving them uncrossed and slightly parted. She rubbed her hands along her thighs. She swallowed, and again.

Michael laid his shirt atop the jacket. The muscles of his arms rippled, his abdomen a washboard. He moved closer, lifted a finger to Sherry’s face, and traced it across her cheek to her mouth, then exquisitely softly across her lips.

Electricity ran down Sherry’s body from her lips directly to her pussy. Her clit throbbed, the walls of her vagina oozed. She raised her own hand from her skirt, which was now exposing her stocking tops, and ran it down his chest across the rippled abs to the waistband of his slacks.

Michael stepped back again, undid his belt, and unzipped his pants. Rather than removing them, he opened the front and moved them halfway down his thighs. Sherry was a bit surprised that he wore white silk boxers; she was expecting bikini briefs.

Michael rubbed himself outside the shorts. His hand stretched the material tight so Sherry could detect the outline of his cock without seeing the flesh. His unconventional strip was really causing her to wet herself between her thighs.

He ran his hand up his shorts and slowly raised the leg so the tip of his cock peeked out. Sherry swallowed hard. He moved the bottom of the shorts higher exposing more and more of the beautiful black organ. When his pubic hair began to appear, he stopped, and let Sherry feast her eyes.

From the closet, Harry was amazed. Flaccid, the black cock was easily several inches larger than his own organ when erect.

Without removing his boxers or slacks, Michael began to deliberately stimulate himself to erection. Sherry squirmed in the chair as she became almost uncontrollably aroused. Finally, Michael stood still with his huge angry phallus clenched in his fist. Sherry knew that Harry was in for the other big shock of the evening.

What Sherry had trouble telling Harry was now arousing her beyond reason. She slid down the seat of the chair onto her stockinged knees facing Michael. This was the part of Michael’s ad that she had so steadfastly refused to allow herself to think about. It consumer her and she felt a complete loss of control when she even approached it mentally.

Her consumption began at the first stripper show when an unknown woman had said, “Yeah, but I heard they charge you $100 just to blow them.”

It continued at the party when a pretty bridesmaid who’d had one too many, wobbled over and knelt before that naked dancer, engulfing his organ and fellating him till everyone present knew he delivered his load.

Fellatio considered if exceptionally pretty Michael’s ad said.

It all came rushing into Sherry’s mind, only quite clearly now, not to be fought off. The women talking about blowing the stripper; the bridesmaid actually doing it. Michael’s soft implication he might, as a favor to the woman paying him to take off his clothes, allow her to suck him off. rather than the other way around. That somehow the act delivers more pleasure for the woman than for him.

Sherry had hesitated telling her husband. The thought of giving a man a complete, swallowing blowjob had always turned her stomach. She had denied Harry. He wasn’t even allowed to cum in her mouth, let alone have her swallow.

But the strippers and Michael appealed to her in a new and unexpected way. The act was now something she wanted to do, needed to do, something so sluttish, so utterly debased and submissive that it brought her to thunderous orgasms as she imagined performing one.

Sherry had asked Michael about the possibility of her performing oral sex for him in one of her emails. She learned that he preferred older women because a teacher had seduced him when he was a teenager. The teacher liked to watch him stroke himself, then suck him to climax. They never did anything else. She was married and afraid of becoming pregnant.

Michael told Sherry the teacher was very pretty and all the boys were hot for her. He said fellatio would depend on how pretty Sherry was, and he needed to see her first. He explained, he reserved it for women who looked like his teacher.

He also said, that although his teacher would never let him fuck or even touch her, she masturbated herself to orgasm every time she fellated him, trying to bring both off together. Michael said if he did let Sherry suck him she’d have to finger herself to an orgasm as well.

Sherry readily agreed. She knew that if Michael permitted her the favor of orally servicing him, she’d easily bring herself off with him.

Now, here she was, on her knees, her eyes pleading with this young black stallion to let her bring him to sexual completion with her lips, her tongue, her mouth. Michael stepped forward in answer to her eyes. He placed his cock head against her lips. Sherry opened her mouth and slid it in.

As she bobbed her head back and forth, Michael said, “Your hand.” She understood the command, and Sherry let her hand move down and push her skirt up as her fingers brushed the front of the thong.

Sherry wanted it to last much longer, but Michael moaned and she felt the throb of his vein against her lips. The first spurt hit the back of her throat and triggered a massive spasm in her clitoris. Her body was rocked as Michael shot six more big shots and a series of smaller ones while Sherry danced on the end of her finger.

Finally, she sagged against Michael’s leg, unable to remain upright without support. Her mouth was still attached to his cock as it now deflated, draining the remainder of his load onto her tongue.

Michael helped Sherry into the chair and began dressing. As he slid his jacket on, Michael extended his hand. “The panties.” Sherry raised her skirt and hooked her thumbs into the thong she wore. Lifting her hips from the chair, she slid it off and handed it to Michael. He slipped it into his jacket pocket and departed, just as he said he would.

Sherry sat in the chair with her eyes closed. She wasn’t even sure if Harry was there until she heard the closet door open. She opened her eyes to see what her husband’s reaction would be. A sheepish grin covered his face and a large wet spot stained the front of his trousers. Harry had cum in his pants.