Exit Strategy

"What?" Jacob asked in dull confusion.

"Business first," Jade said, "Now, what do you have for us today Mr. Finning, the installment, or the whole thing?"

"Briefcase," he mumbled, while staring with interest at the two transsexuals.

Jade looked around and found it. Then she took the time to count all the hundred dollar bills, while the two trannies helped themselves to drinks from the fridge. When she was done counting, she thanked Jacob for the gift.

"Jackie, you kept your word. I've decided that these two girls can have as much of this as they need to continue with hormone treatment and/or breast augmentation and new clothing. And they'd like to thank you for your generosity, wouldn't you girls?"

They just giggled and sipped on their wine, but their penises were already showing signs of erotic interest.

Jacob noticed and found that he was aroused as well. He didn't know what about, but it seemed to be just the general scene. They were going to use him for sex, he guessed, and that seemed right to him.

"You're turned on by this, aren't you Jackie? I know it and you know it. You're going to do everything we ask, aren't you? Because you want this, don't you Jackie?"

"Oh yes. Yes, yes. What?" He briefly forgot what he wanted. "Yes, I want this. Just tell me what I have to do..."

Jade came to him and reached under his dress, grasped his girdle and laboriously pulled it down so that he could step out of it. His penis gave it all away, tenting the tight dress as much as it was possible to do so. She turned him toward the camera, then sideways to it to get both angles of his arousal.

"Perfect," Jade said, "Now, bend over the bed please and spread your legs."

She guided him over and pushed him and held him down face first while she lubricated a large butt plug and gradually inserted it while he squirmed and moaned with the initial pain. Once it popped in, he squealed once and then he was quiet.

"Sit up and let that settle in place," she ordered, "In a little while your vagina will be stretched out so we can all use it. You have a vagina, don't you Jackie?"

Jacob, as if in an excited trance, rolled over and sat up, instantly gasping with the intensity of the penetration and pressure against his prostate. The black girl giggled and got on her knees in front of him. This was the best dream ever.

"You're so hard," she whispered, "Let me make you more comfortable."

She took him into her mouth and he closed his eyes, totally helpless to her fondling. He had no defences; he was that easy. He was immediately in erotic sub-space.

"Look at the camera Jackie. Maybe this will be on YouTube someday, so smile."

"What?" he gasped breathlessly, "No, oh no, no, no..." But it was really a yes, and a weak protest, as he stared at the blinking video light and closed his eyes in bliss. He wanted this to go on forever, but it was not to be, at least not this way.

"Marcie, we have him for the whole day, so don't let him come yet. You and Jen and I are going to use him as much as we can. Don't think of him as a person, just sexual meat, like he used to think of me. He's a slut and a whore. We get to use him for whatever we want, for as long as we want. And the amazing part is that this is what he wants too, isn't that right Jackie? That's the slutty part."

"No...oh God...fuck...YES! Fuck!" He was so angry that he wanted this...angry at himself to be needing this.

Marcie let his penis flop out of her mouth and she smiled deviously while teasing with her hand and tongue on the outside, up and down his shaft, but never enough to satisfy to climax. Jade decided to take the lead on the scene and pushed Jackie down on the bed on his back while she mounted his face. He instinctively started to lick and suck at her vaginal lips and clitoris, sometimes having all his air removed from him by her convulsions. His arms flailed about searching out her body above him, grasping her breasts and caressing the erotic tightness of her corset at her tiny waist. He couldn't coordinate any resistance due to his mental fog, and the resultant helplessness caused him to let go of whatever remained of reality, to drift in a mist of erotic awareness. He felt like he was drifting down a river of lust. He had never been on such a large river, never had a dream like this, and he never wanted to wake up.

Marcie continued to fondle him, and he felt other hands caressing his corset and bra. He stroked his own breasts, surprised that he was a woman in this dream. His mind arced and short circuited, and despite Marcie's remote teasing, he ejaculated, jetting arcs of semen up at a surprised Marcie who licked him clean and swallowed it all with clear joy. Even though Jackie's passion had been sated, Jade continued in her motions on his face, and he could hear her passion rising and was now able to concentrate on her pleasure, not his. It felt good to be free from the expectations of his maleness, to be just a useful pleasure slave. He was a woman loving another woman in this state.

When she came, it was announced initially as a sharp shriek, and then it settled into a long deep moan as she let herself relax and settle on his face, sealing his nose and mouth in a vacuum of sexual juices. In her excitement, she had pinned his hands to the bed by his side as she leaned on them. At first he was happy she had come, and he waited for her to roll off. Instead she just kept him pinned and shuddered over and over again, with no apparent end.

He couldn't move. He couldn't breathe. He began to panic. His black world started to have color in swirls and blazes of bright intensity. He tried to remove himself, but was only able to buck his hips. Oddly the lack of oxygen gave him an erection again and Marcie engulfed it gleefully in her mouth. The confusion of erotic bliss mixed with a lack of air started a scream as he tried to move his head back and forth to get air.

With a final shudder, Jade rolled off. As she did, Jackie sucked in the air at the same time that he came for a second time, once again in Marcie's mouth. But instead of swallowing it, she filled her mouth with as much as possible and leaned forward, depositing it in his. He looked at the camera sheepishly and submissively, and swallowed, licking his lips, with his breasts heaving, wanting more.

"You're a lesbian, aren't you Jackie?" Jade said, "You like making me come, don't you? You're a woman, and you're a lesbian. That fits you perfectly for now. But you're more than that. You're a trannie that likes cock too, aren't you Jackie?"

Jackie stared at her as she went in and out of focus in his dream. Yes, that was it. Lesbian...

"Yes, I don't know...maybe..." he said.

"Do you like cock Jackie?"

"I...I'm a...I like..." His face showed confusion and it was clear his psyche needed more guidance.

"You feel like a woman, don't you? You are a woman, aren't you Jackie?"

"Yes. Oh...fuck!" he said as he squeezed his own breasts, lost in the moment and the suggestion.

"You're a woman, and women like cock don't they Jackie?"

"Yes, that's right...oh my God," he whispered, in awe at what this meant.

"So you like cock, don't you Jackie?"

"I...uh, I guess so, I don't know..."

"Well, you're about to get what you want. Get on your hands and knees sideways on the bed Jackie so you can see yourself in the video later."

In his dream state he felt Marcie touch the tip of her penis to his lips repeatedly. Then he felt his anal plug being removed and a cold jet of lubricant being forced into him, followed by Jen's hot and thick penis. It was impulsive; without any further hesitation he took Marcie's penis in his mouth and started to suck while Jen hammered him from behind.

Jacob was desperately needy, abandoning himself to the joys of this assault. He grunted and moaned with every thrust into both his male vagina and his mouth. Fluid was dripping and sometimes squirting out of his impossibly erect penis as the prostate was being forcibly drained. Miraculously he felt yet another orgasm approaching. He had never had three orgasms in a whole day, let alone the hour he had been subjected to this. He attributed it to the wonders of a dream, and he waited for that inevitable fullness of pre-ejaculation with stunned ecstasy.

Jade was beside his head and she knew what was about to happen. She needed to drive the knife in a little further so she gently grasped his penis and talked huskily into his ear, "Humiliating, isn't it Jackie, being taken like this? You're just two orifices to be filled. But you like that, don't you? You're a slutty woman, aren't you? This is your new position in life; you might as well get used to it. Normal sex won't cut it any more, will it? Your poor wife Carol; she won't have a husband any more. She won't ever know that she's married to a woman, will she? Unless I tell her."

She timed it right. Both Marcie and Jen were starting their convulsive orgasms. Jackie's mouth filled with jet after jet of salty semen overflowing out and down his chin, and for the first time ever he felt the warm tickling squirts of fluid from Jen filling him with her seed in his vagina. Just then Jade started to rub his penis and he came with a shattering violence that shocked everyone.

He sounded like he was crying, but it was dry, with no tears to mess his makeup. It was like he was wrestling with pain, trying to make sense of it, to deal with it and overcome it. In a way, he was.

He looked at the camera for a long time, breathless, with occasional slight whimpers as he licked traces of semen from his lips and chin. For these post-orgasmic moments, the drug had briefly released him to have rational thought.

With a dead, beaten look in his eyes, he smiled with resignation, sighed, and said, "Holy fuck...holy sweet fuck!"

Jade spoke more loudly now. "We've only just begun Jackie. Your work to service us has just started. So much to do, so little time. You've had your orgasms. No more for you today."

"I know," he said, "I know." His mind created a quick snapshot of his future. These people could do anything they wanted to him, because he had too much to lose by defying them. And he had so much to gain by submitting to them.

Strange how things worked out sometimes, he thought. Fantasies that propelled him in this direction in the first place would now bind him and hold him forever, a bondage of need and necessity.

As the drug fog closed in on him once again, he felt the cuffs close on his wrists behind his back and he found his mouth filled with a penis gag that was strapped tightly behind his head. When he tried to get up, he realized that his ankles had been cuffed together as well.

He knew they would use him for whatever they wanted for the rest of the day. There was no way out. But there was no memory of these thoughts, nor was there any cognisance of how they used his mouth and vagina over next few hours in between their breaks while they had room service and glasses of wine and occasional smokes of weed.

Jacob woke up the same way he did the previous week, still dressed as a woman, and his butt plugged with a vibrator that was still going, held in by an extremely tight girdle. He was alone.

He was hungry, his penis, mouth, jaw and anus were sore, and even though he had no memory of the events, he knew he had been used quite thoroughly. He looked at his watch. It was 5:30 and he had a headache, so he called Carol and told her he would be having supper at the office and would be home very late.

"Okay," she said, "You sound weird. Are you okay?"

"Oh Carol, it's been a wild and rough day. I can't tell you about it...I really can't, you know how that is...but I have a splitting headache and I need something to eat before I start working again." All of this was the truth, and it felt good not to be lying for once.

He washed up in the bathroom after the call ended, removing all the makeup and taking off his wig and earrings. He started to remove the girdle to free the buzzing vibrator, but then he stopped and made a quick decision. He padded back to the hotel room door and without hesitation put on his suit clothes over top of the corset, bra, and stockings. He left, stopping in the hotel lounge for a glass of wine and a plate of prime rib, and as he regained energy, the erotic feel of the corset made him want her again. He ordered a second glass of wine, drank it and went back to his office where he knew he could think.

When he arrived, he checked all the offices before entering his, locked the door and removed his male clothes to reveal the dress which was pulled up above his waist. He pulled it down, opened his suit case and filled his bra cups and put on his high heels as well as his wig. Now he could think.

It was obvious what he had to do; he had to find a way to stop this, but as he mulled the various thoughts in his head, nothing became clear. He was where he was, and there appeared to be no way out. To distract himself he turned on his computer and as the emails loaded up, an inkling of what to do whispered to his unconscious mind. That was interrupted by a particular email and his heart sped up instantly as he sat bolt upright at his desk.

Jackie,

Thank-you so much. We all had fun with you and took lots of pictures. You really seemed like you enjoyed it too. Here are the pictures and the video so you can add them to your scrapbook.

Same time, same place next week. Oh, and book October 16-22 week off for a "business" trip in Toronto. It's during the fetish convention, and your attendance and off-hour usage will be compulsory.

Love,

Your owner, Jade

Video? He had already seen the video. Then it struck him, and he said, "Oh no...oh my God, no, not another one!"

He watched it with horror as this happy and lustful transvestite serviced the three woman, none of whom (other than the transvestite), was identifiable, and there was one part that sealed his fate: "Your poor wife Carol; she won't have a husband any more. She won't ever know that she's married to a woman, will she? Unless I tell her." He had had an orgasm at exactly the time when she had told him that, as if it had been the trigger.

In his mind, he knew it WAS the trigger, and now it was the glue which would keep him in this trap forever. She would take him for everything he had if she found out. He collapsed back into the large leather chair and looked down at his breasts and his nylon-clad legs stretching exotically from out of his clingy dress and closed his eyes with the confirmation of his earlier inkling of a solution.

He quickly typed an email to Melanie, his receptionist, asking her to clear his timetable for next Tuesday and also for October 16-22. He had no solution other than to enjoy this without destroying his vanilla life.

Jackie suddenly felt a weight being lifted off his back, and he went to the bar fridge, poured himself a glass of white wine, and stood sipping it from his seventh storey window, in full bright light, fully visible to any that chose to look. He had been foolish to think that he could contain and hide this.

He held out his glass, a toast to the world, and said, "Okay, fuck it, here I am. My name is Jackie. Here's to Jackie!"

He drank it slowly, smiling as he did, then went to the washroom and applied his makeup for another few precious hours before he had to become Jacob again and go home to his wife and two children.

And all the rest of it.

The End