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..."
