From Saint to Slut

Eventually, she felt Jack's hand working steadily in her pussy, fingering her hole and rubbing her clit. Gail felt sizzling feelings climb up her back as Jack expertly manipulated her cunt. Suddenly, she felt a finger at her asshole, and she gave a quick gasp and tensed up.

"Relax, Gail," Jack said softly. "It's going to happen, you know that. Don't fight it. Relax, and it will go so much easier."

Gail took a deep breath and nodded her head. Just then, Ron slid up the bed, turned her onto her side and offered her his cock to suck. She took his long shaft in hand and bent her head to his lap, opened her mouth and slid the still-wet member into her mouth. As she did, she felt Jack's fingers beginning to work purposefully in her butt. He squeezed a dollop of lubricant onto his finger and lightly rimmed the hole, getting it slick and loose, then slowly slipped his finger in. Gail tensed up for just a second, then willed herself to relax, and, sure enough, once she did, entry was much easier.

Jack fucked Gail's ass with his middle finger as he watched her suck and slobber all over Ron's cock. The longer he did it, the better it began to feel for Gail. Jack soon added a second finger in her butt, while also using two fingers on her cunt, getting all four fingers working in rhythm to her sucking motion.

Abruptly, Jack pulled his fingers away, and grabbed a pillow from the head of the bed and moved Gail around, so that she was on her stomach, with the pillow under her abdomen, elevating her hips slightly. With Gail in that position, Ron also moved, so that he was leaning back on the headboard, his legs open, his cock aimed at the ceiling.

Gail looked up at Ron with a smoky look of lust as she fed his cock back past her lips. In this position, she could get more of his cock in her mouth than before, and she worked her head up and down slowly, as Ron groaned in appreciation. When Gail had a good steady rhythm going on Ron's cock, Jack resumed fingering her ass, getting her ready for her first-ever ass fuck. With his other hand, he stroked his own ballistic cock, getting it all slick and ready.

Jack pumped and rolled his two fingers with increasing vigor in Gail's ass, and despite her fears and reservations, she had to admit that it was starting to feel pleasurable. When Jack felt like his cock was at maximum strength, and Gail's hole was ready, he pulled his hands away, and pulled himself up on his knees. He felt a rush as he saw his ex-wife's virgin asshole, wet, gleaming and ready for him to fuck.

"OK, honey, just relax," Jack said in as soothing a voice as he could muster under the circumstances. Gail pulled her mouth off Ron's cock and took a deep breath. She closed her eyes and gripped Ron's arms as Jack pressed the head of his fat cock to her anus. She held her breath and squeezed her eyes shut as Jack slowly pushed the head past her sphincter, until suddenly the head popped past the tight ring and into her rectum.

Gail couldn't help it. As much as she tried to relax, as well as she'd been lubricated and opened up digitally, she still screamed in pain as Jack's fat cock passed into her ass. She had a death grip on Ron's upper arms as Jack slowly pushed more of his cock into her rectum. After he had about a third of his cock in, Jack stopped and held it still, to give her ass a chance to get used to the intrusion. But it was hard, because Gail's ass was about the tightest thing he'd ever put his dick in.

And, as she slowly adjusted to the fat dick in her butt, Gail began to feel, not pain, but pleasure. She couldn't believe it, but it was true. She was starting to get little tingles of pleasure from Jack's cock in her ass. She had always thought of anal sex as dirty, degrading and not the least bit pleasurable. But as Jack resumed pushing his cock in, Gail realized that it felt good. It was much different from having a man in her vagina. There was an indescribable fullness to the feeling.

"Ahhhhhhhhh, God, Jack, that almost feels good," Gail said.

"Wait until I really start going, and you really start getting the feeling," Jack said. "It's like nothing you've ever experienced."

"Mmmmmmmmmm, wow!" Gail exclaimed, as Jack finally got all of his cock in her ass and began to fuck her with slow, steady strokes. Just then, Ron tapped her on the head and she looked up to see him grinning and holding his cock up for her to resume sucking, which she did with gusto.

Unbelievably, Gail felt herself pushing her butt back on Jack's pistoning cock, as she got into the rhythm. Sparks of pleasure coursed through her body as she began to lose herself to lust again, her passion boiling over.

Jack got a firm grip on Gail's hips and began to work her ass back and forth on his cock. He was grinning as he realized that his once-prudish ex-wife was enjoying having her ass fucked. And indeed she was. Gail felt a kaliedescope of sexual feelings tumble through her mind and body as she let Jack fuck, yes fuck, her ass and let Ron push his cock harder and faster in her mouth. She still couldn't take all of him, but she could take more than she had earlier, to the point where the head of his cock was pushing at the entrance to her throat.

Together, the two men worked their rock-hard cocks back and forth in Gail's sweaty body, as their frenzy mounted. Gail was having trouble concentrating on Ron's cock, as the feelings swelled. She pulled her mouth off his cock and let out a series of pre-orgasmic moans and cries, while tossing her head around trying unsuccessfully to get a handle on herself. She dimly felt Ron forcefully rubbing the wet head of his cock all over her face, then felt him push it back in her mouth, where she resumed sucking him with hard, deep strokes.

Jack was working his cock harder in Gail's ass, as she rolled her hips back in rhythm with his thrusts. She was getting more and more frenzied as the climax built to a crescendo. Finally, she couldn't keep Ron in her mouth any longer.

"Unnnnnnnnnh! Ooooooooh! Ahhhhhhhhhhh!" she wailed. "Oh God, fuck meeee, fuck meeee, make... me... cummmmmmmmmmm!"

At that, she felt everything explode like a nuclear bomb. Her orgasm was like nothing she'd ever experienced. It started like an earthquake, her whole body shaking and shuddering as the waves of sensation crashed over her.

Jack couldn't hold on any longer. Gail's orgasm caused her rectal muscles to twitch and clench, all but forcing his cum from his dick. He gave a strangled yell and erupted with a fountain of cum, bathing Gail's bowels with hot, wet semen. He just kept pumping, shooting burst after burst of cum in her butt.

Ron had been jacking his cock hard as he watched Gail, then Jack tumble over the cliff in breathtaking orgasms, and now it was his turn. His hands flew up and down on his cock as the tingle in his scrotum triggered a stony climax. Gasping, he aimed his cock at Gail's face, and she squealed in shock as he planted four powerful ropes of cum on her face. He sent the first shot over her forehead and into her tousled hair, then he covered her eyes, her cheeks and finally her chin with cum before pushing his cock back in her mouth to get the last oozing drops of cum. He squeezed his cock tight to make sure he got every drop before he finally pulled his cock free and let her slump onto the bed.

Slowly, the trio came back to earth. Jack pulled his cock free of Gail's ass, and felt a shiver of excitement race through him as he saw her reddened asshole stay open for a few seconds and discharge a small river of cum before it slowly closed back up. He fell back on his haunches, sweaty and his chest heaving. He was pleased with himself. He'd done what he'd set out to do, begin the process of making his ex-wife into his kind of woman, one who could and would fuck at the drop of a hat. And just the thought put some starch back in his cock.

There was one more thing he wanted to do this night, however, to get Gail fully in the fuck mode. He fixed Gail yet another glass of wine, and she accepted with more eagerness than she'd ever shown before. Gail sat up and drank, fully aware that she was beginning to get drunk, but welcoming the feeling, because it loosened her up to where she could enjoy what was being done to her, and numbed her mind so she didn't have to think about it.

After resting for awhile, and getting Gail two more glasses of wine, the trio found themselves on the bed again. Gail was lying on her stomach, with Jack on her right and Ron on her left. She was idly stroking both cocks, lost in a semi-drunken haze. Both men were getting plenty hard from her slow manipulation, and she giggled as she watched pre-cum ooze out the tip of both cocks.

"So, what're you guys gonna do to me now?" Gail asked in a slightly slurred voice.

"Something special," Jack answered. "Something that will make you cum like a rocket."

"Mmmmmmm, sounds nice," Gail said. "What is it?"

"You'll see," Ron said, as he began to slide his fingers between Gail's legs. He alternated between her cunt and her ass, both of which were wet and open. Her ass still had remnants of Jack's earlier cum, and her pussy was flooding with renewed arousal. Gail's eyes were closed in reverie as she felt the sensations begin to mount, just from Ron's expert fingering. While he manipulated Gail's crotch with his right hand, his left hand was steadily stroking his cock, getting it up to full hardness.

Taking his hand away from Gail's body, he maneuvered her onto her left side, so that her back was to him. He lifted her leg with one hand and fitted the head of his cock to the entrance of her ass. With a subtle push, the head plopped past her anal ring and into her ass.

Gail gasped as Ron's cock invaded her ass, then moaned in lust as the hard shaft filled her rectum with his quivering meat. As soon as Ron began to get into a fucking rhythm, Jack began to work his fingers briskly in her pussy. Gail left herself getting lost in lust as Ron's cock sent waves of sensation from her ass to her pussy and up to her brain.

Ron looked over Gail's shoulder at Jack, and they both nodded to each other. Keeping his cock firmly embedded in her ass, Ron grabbed the petite blonde and rolled her over Jack's hips onto her knees. Until that moment, Gail had been oblivious to what they had planned, but when she felt Jack's cock at the entrance of her pussy, she suddenly realized what they were about to do.

"What are you..." Gail began, but Jack just shushed her.

"Relax and enjoy," he whispered as he fit the head of his cock in her hole. Then he and Ron pushed her hips down on Jack's cock, impaling her on his rod.

Gail felt the air leave her lungs when Jack's cock filled her pussy at the same time that Ron's cock was deep in her ass. This was something she'd never even heard of, but as the two men began to work their cocks back and forth, she could feel a climax of gargantuan proportions building up. She had never felt this full of cock before in her life, and it was like lighting a string of firecrackers. Gail's body went into overdrive, working with the two cocks in her body.

They hadn't gotten going good before Gail's orgasm swept over her, but incredibly, she seemed to stay at a height of sexual sensation. As Jack and Ron slowly, but steadily fucked their cocks in her pussy and her ass, Gail began firing off hard orgasms, one after another, her sweat-covered body twitching and shuddering with each hard explosion. Her mind was blown to the point where she couldn't think of anything but pleasure, of sheer wanton sexual pleasure. She moaned, groaned, cried, panted, gasped, and begged for more.

Over and over, Gail's body was wracked with climactic spasms until her mind was shrouded in a white haze. Jack and Ron, too, were working their cocks harder and faster, their bodies also covered with sweat. Jack periodically reached up and squeezed Gail's tits, which danced delightfully on her chest, the fat nipples stiff and swollen.

As they picked up steam, Gail's orgasmic cries became more pronounced. From some dim recess of her mind, she knew they were about to explode, and she wanted to explode with them. She wanted - needed - to finish off this night of pure lust with a three-way orgasm of volcanic proportions.

Jack and Ron had done this so many times with Debra and others that they knew instinctively when they were ready to blow. On cue, they each grabbed some Gail's sweat-slick hips and worked her hard on their pistoning cocks.

As cries of, "I'm cumming!" filled the room from all three of them. Jack and Ron felt their cocks explode almost simultaneously, firing hot, wet loads of cum deep in Gail's spastic holes. Almost at the same time, Gail felt her whole body quiver, as if she'd been electrocuted. It felt almost like the two cocks that were spitting out semen were going to break through the membrane that seperated her pussy from her rectum. She gave out deep, gut-wrenching sobs as the climax swept through her like a tidal wave. Then, as the waves of feeling subsided, she gave a deep sigh and collapsed onto Jack's heaving chest, out cold.

Ron gingerly extracted his red, wilted cock from Gail's gaping asshole, and he too got a charge out of the way it stayed open for a few seconds and the way the cum slid out of her hole, where it mingled with the equally heavy flow of cum dribbling out of her pussy onto Jack's balls. The two men grinned at each other as Jack rolled Gail's limp body onto the bed.

Then they got up and began to get dressed. They still had some work to do before Gail woke up, which probably wouldn't be until morning.

Sure enough, Gail awoke the next morning to a foggy mind and an aching body. At first, she didn't know where she was, but quickly everything flooded back to her memory. It was only when she got up to use the bathroom that she saw the printout on the dresser. She gasped when she realized that it was the previous night. It was a clear print of them engaged in the double-penetration, the climax of the night. Gail felt a sense of shame as she recalled how she had acted at that point in the night, like some 10-dollar hooker who couldn't get enough sex. Yet she also recalled just how good it had all felt, how intense her orgasms had been.

There was another print taped on the bathroom mirror, only this one had a written message at the top.

"You were sensational, my dear," it read. "I'll be in touch. Love, JM"

Gail knew now that she was truly trapped, that Jack had her completely under his control. And she couldn't decide whether she hated it, or liked it.

Jack didn't contact Gail until the following Thursday, when he told her to meet him in the city that evening. He had something he wanted to show his ex-wife.

Gail was on her period, and she told Jack that, but he said that was OK, for what he had in mind, sex wasn't necessary. So they met for dinner and drinks, where Jack outlined two things she needed to do as soon as possible.

One was to see about contraceptive action, either the pill or an operation to tie her tubes. He didn't want there to be any chance of pregnancy. The other was long-term child care. She was going to be going out at his behest almost every weekend, sometimes both Friday and Saturday nights, and occasional week nights as well, and he wanted to make sure their children were in good hands. Jack suggested they hire a live-in caretaker. Jack offered to increase what he planned to pay in child support, to $1,500 a month, to pay for it.

"Do I have a choice?" Gail asked, with a trace of sarcasm in her voice.

"Yeah, you could pay for it yourself," Jack said tersely. "Gail, never forget that I own you now, so it would be in your best interests for you to keep me happy. You won't like what you have to do if you piss me off any more than you already have."

After dinner, Jack told Gail to get in with him for a little drive. Gail was curious, but said nothing. She was appalled when they pulled in at the city's most popular strip club.

"Why are we stopping here?" Gail said, as Jack parked the car and they headed for the entrance.

"I just want you to see something," Jack said, an evil twinkle in his eyes. Gail shuddered at the implication in his look. He was up to something more than just another sexual encounter.

They got a seat in the busy club, and they watched the sexy, exotic women dancing on the stage, proudly parading their bodies. Gail had several glasses of wine, and that feeling she'd had the previous Saturday at the Hilton returned. She had that nervous feeling in her stomach, and she was astonished to feel her pussy getting moist from the pure sex that was radiating from the stage.

Throughout the night, Jack showed Gail some things the strippers were doing, as if he was trying to give her pointers, which, in fact, he was.

On the way back to the restaurant where Gail's car was parked, Jack fished out his hard cock and told Gail to suck him off, which she did, swallowing his rocky load just as they pulled into the deserted parking lot.

The next Friday, Jack came to the house to get the children for the weekend, and at that time, he introduced Gail to Lita, whom he had hired as Gail's live-in nanny. Lita was his secretary's niece who was starting graduate school at a nearby college and needed an inexpensive place to live for the duration of the school year. Lita was told, as were her children, that Gail had gotten a part-time job that involved working some nights, especially on weekends. Lita suspected there was more to it than that, but she kept her mouth shut. She would move in the week following the Fourth of July holiday, which was the weekend upcoming.

On the following Monday, Jack called Gail and asked if she could find a sitter for the kids the next day.

"I have to attend a party Friday night, a work-related deal, and I'd like you to go with me," Jack said.

"Why me, and not Marie?" Gail asked, referring to Jack's fiancee.

"She has family coming in for the holiday Friday and can't get away," Jack said. "I thought we might get some lunch, then do some shopping. I'd like to buy you a new dress for the party to kind of make up for the way I've treated you the past few weeks. I know it's been hard for you."

This was Jack at his most charming, the Jack that Gail had fallen for all those years ago, so she accepted. Truth was, she had wrestled in her conscience with what she had done at the hotel, and how she had reacted, and it hadn't been easy. Many of her moral assumptions had been dashed by her participation in those activities, and by her enjoyment of them. Furthermore, she was startled to find that she was actually looking forward to her next encounter with Jack. It had been over two weeks, and, unbelievably, she was horny. So much so, that she had willfully resorted to masturbation on a number of occasions.

Jack took her to a nice restaurant for lunch, where he insisted that she have a couple of glasses of wine, then took her shopping. He bought Gail a new pair of high heels, and a couple of fairly conventional dresses, then bought her the one he really wanted to see her in. It was at a Fredericks of Hollywood boutique, and he said it was perfect for her new, more liberated personna. It was an Asian-style suit, with a button-up jacket with three-quarter sleeves as the top and a mini-skirt, red with an Oriental floral design. It was made from a polyester/spandex material that fit snug on her curves with just a hint of cleavage. Gail had to admit that it looked exquisite. He also bought her several items of very skimpy underwear, including a red bra and thong set that matched her new red dress.

When they got back to the house, they still had two hours to kill before Gail had to pick the kids up from day camp at the Y, where she'd taken them earlier. So they spent a good bit of that time in bed. There was no coercion this time. She was a willing and enthusiastic participant, and Jack was at his most loving, bringing her to a sharp climax with his lips and tongue, then slipping his cock in her and fucking her leisurely until she had another powerful orgasm. When he finally came, Gail pulled him up and cleaned his cock, just the way she had for Ron that night at the Hilton.