• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • The Contract Ch. 02

The Contract Ch. 02

Jade walked away in triumph, her stomach fluttering with butterflies. Darren paced in awe behind her, himself also quivering with excitement.

She turned and smiled at him, and he returned her joy. It was a match made in heaven.

The long walk ended in her bedroom which was at the end of a long hallway off the living room. She stopped him just inside the door. Ahead of him were floor to ceiling windows framing the mountains in the west, the sun just setting and the blue, orange and yellow hues fading fast. The scenic feast was suddenly obliterated by the drawing of the curtains. It seemed like the very reality of the room was snuffed out by that action, as the view not only disappeared, but the sound changed. In fact, it changed the acoustics so that there was no sound as Jade stared at her new possession.

"Welcome," Jade said finally, as she sat thoughtfully on the end of the bed. She began to disrobe, revealing what he already knew was there, the corset and the attached hose, both of which were black.

Darren stood awkwardly, uncertain as to what to say or do. He answered, "Thank-you ma'am."

"Darren, I have some boots in the closet, the black ones, knee-high. Go and get them and put them on my feet please. Anything worth signing your life away for is worth an initiation ritual, don't you think?"

"Umm, I suppose so ma'am." When he entered her closet and turned on the light, he was astonished to discover rows of fetish-like boots and shoes lying underneath hangers draped with dozens of corsets and bustiers. She could have opened a shop with them. There were three pairs of boots that were black, but he chose the ones that laced up from the ankles to the knees and brought them to her.

Jade was still seated but there was an item on the bed that was unfamiliar to him. It was like two aluminum rods, one extended from the other in a "T" formation, the other end fitted with a rubber or silicone phallic device. The cross of the "T" had straps at each end which were intended to buckle closed onto something. His observations were interrupted by a firm but gentle order.

"Don't be slow now. Get on your knees and massage my feet before you fit the boots on my legs. You love them don't you?" she said, her voice smooth as honey.

"What? Oh yes, the boots are lovely ma'am."

"It figures you'd say that. I was talking about my legs, you idiot!"

Darren's face turned an even more intense shade of red as he floundered around with a reply. "Oh yeah, that's what I meant, the...your legs...oh my God, you are beautiful ma'am," he groveled.

He knelt down, being careful to keep his knees together as he had already been trained to do. His own hose and undergarments shifted slightly on his now hairless body, intensifying his arousal. She was so stunningly beautiful with her waist pulled in so tightly in the corset. He wished he had a corset like that.

He rubbed her legs slowly, adoringly, gradually shifting his touch to her feet where he began to slowly and expertly massage through the arch, over the instep, between her toes. He listened to her breathing in order to modify his touch as he hit the spots that she most desired. He was meant for this. He was meant to serve.

After several minutes, Jade was purring, leaning back on her elbows with her head back and eyes closed. Several minutes after that she reluctantly sat up and said, "Okay, good job. Now get my boots on. Lace them up carefully and nice and tight, Darlene. Is that clear?"

"Yes ma'am," he said, and then with trepidation and hesitation, he added, "Umm, ma'am? Can I make a request?"

He was shocked by her answer, "Well, actually, no, no, you can't. Because I don't want anything from you right now but service. Ownership makes the rules and I own you. It's in the contract. You signed it."

"But ma'am, I need, I want to...umm..." He was going to say that he wanted to make love to her.

She cut him off, "You? You need and want? That's all very sweet and all that, but I decide what you need and want now, okay sweetie? Now put my boots on. Come on, I have plans for you."

"What? You mean I can't even ask...?"

Again, she cut him off, "Please, Darlene, stop this. I made a simple request of you. Now do it!"

He was stunned by his own reaction, as he was almost orgasmic in the ecstasy of humiliation and degradation of her domination. Suddenly he was overwhelmed by comprehension of what he had done. His jaw went slightly slack and he stared at her in the realization of where his sexual addiction had led him.

"Oh my God! I, I...oh jeez, I... Look, I don't know about this, umm..."

Jade looked down at him with mock sadness and said, "Oh, you're having second thoughts I see. That's really too bad. I had big plans for you tonight, and forever actually. Do you want to leave me? You can you know. Even go to the police if you want. Too bad about that signed contract though. Your assets are still mine. But you can leave. Do you want to leave Darlene? Hmm? Oh my, you're pouting. Here, let me fix your lipstick, DARLENE." She took some lipstick out of her purse on the bed and applied it carefully, stoking his fantasies. The color did not match what he already had on, but in this demonstration of power, that didn't matter.

When she finished, she looked him squarely in the eyes and said, "Boots please."

Darren's breathing was ragged as he looked away, anywhere but at her confident face. But the room was getting darker by the second. He needed time to think. But his mind told him that there was no time for that. Not that he was rushed; it was just that the time for that had passed. He had indeed signed all his assets away.

For now, he thought it best to continue the scene. Groveling at her feet, he fitted the boots to her, lacing them up with perfect precision and care. When she stood up, she towered over him in the six inch stilettos.

"Stand up!" she ordered. There was something different about her voice. It had more timber to it. There was no honey.

"Remove your panties." She meant business.

"Yes ma'am." He was hoping this meant something good for him, and his cock leaped from the confines of the lycra garment, making a tent in the front of his skirt.

Jade now locked leather cuffs to each of his wrists and in turn locked them to his steel neck collar with two 6-inch lengths of chain. His hands now hung like a begging puppy, useless and helpless.

"Perfect!" she exclaimed, "Now spread your legs. Keep your heels on. I want this to be awkward and painful."

Then she reached for the contraption on the bed, first taking it apart, so that only the bar with the leather straps came with her as she bent down to attach each end of the bar to one of his ankles. When she was done, his legs were bound together but his feet were forced to stay about three feet apart by the spreader bar.

"Oh shit," he said with apprehension.

Jade giggled at his moment of despair and gave another order, "Move to the bed and lean over with your bum in the air."

"What? What for?" He was slightly alarmed at where this was going, but he did as he was told, actually losing his balance when his elbows hit the bed. He would not easily be able to get back up because he could not use his arms to push, bound as they were. He stared ahead and waited for the next commands. He thought maybe she wanted him to perform oral sex on her, expecting to see her spread-eagled before him on the bed. But instead, she lifted his skirt and caressed him softly on his smooth hairless ass, and reached around to gently stroke his penis.

He sighed in heavenly bliss until the cold lubricant splatted against his anal opening.

"What are you doing?" he asked in alarm, "Don't touch me there."

Jade took offence to this and slapped him hard on the buttocks causing him to recoil helplessly on the end of the bed. "I decide when and where I touch you. Remember?"

"Oh shit...oh shit, yes ma'am, but...oh shit..."

As he lay there waiting for more surprises, he could feel his legs being jiggled by the spreader bar behind him as she attached the other part of the device. Suddenly she grabbed him by the steel collar and helped him to a standing position. The movement created a flow of air over his lubricated ass and it felt cool and extremely vulnerable.

"Stand still and relax. It's better if you relax. Pretend you are about to fart, but don't. That's how to relax the opening. I'll be gentle and use all the lubricant I need."

"Ma'am, what's going on? Look, you know I'm not gay, right?" He felt the first pressure at his anus and the narrow tip slipped in slightly causing him to gasp.

"Of course you're not gay. That's why I'm doing it, lady boy. As far as I'm concerned, this is your vagina from now on. Is that clear?"

She pushed harder on the pole. "And your penis is your clit. Is that clear?"

The perfect model of a penis was now inside him by about two inches and he gasped, "Oh Jesus, that hurts, oh Christ, oww, oww..." Then his mood changed. It was sudden and it shocked him.

"Oh my God, oh fuck, oh fuck..."

Now the devious nature of the device became apparent. The rod was telescopic, originating from his spreader bar, and she pushed and pushed it up, up until he stood on his toes trying to reduce the penetrative thrust. She waited for him to relax and then pushed some more. After several minutes he was fully extended and the anal phallix was fully inserted. She locked it in place with the set screw. He was impaled. And there was no way out of it.

"Jade, please..." His hands writhed in futility underneath his chin. He could reach nothing. He tried to bend over and felt the artificial cock inside him move, but it was so far inside him that he could not push it out. Not only that, but he could neither sit down nor lie down.

Jade laughed and said, "I've been dying to try this anal impaler for weeks now, and finally I have a slave I can experiment on. Finally! Now walk around a bit. Be careful, because if you fall, you only have your hands and elbows to protect your head. You have to go slow."

"Jade, really? This is embarrassing. I feel like an idiot." He awkwardly swung his legs in roundhouse movements to advance himself across the floor. Each movement caused the anal plug to move deeper within him, creating a feeling that he had never felt before. His breath started to come in short puffs as his prostate swelled to the occasion.

"You think THIS is embarrassing? Ha, just wait then! You're going to have quite a night."

Without her even telling him to do so, Darren was walking about as best he could. Jade interrupted his erotic haze and said enticingly, "For being such a good sport, I'm going to jack you off. Then I want you to go to the kitchen and get us a bottle of wine so we can celebrate our union. Sound good to you?"

"Oh my God yes. Would you do that? Oh God, thank-you, but what can I do for you? I can't really respond for you."

"Lots of time for that. Lots of time."

Within seconds she drained him of his juices and cleaned up his mess. It was business like, almost like there was a higher purpose to it, one that he could not fathom at this time. In fact, it was disappointing, like he had just been milked like a cow.

"Now go get the wine."

"Well, aren't you going to release me?" Darren asked.

Jade smiled and answered, "Now why would I do that? Wine please."

Nothing exposes a person's psyche as much as revealing your most bizarre fantasies and then having an orgasm to the tune of them. Once one opens his eyes after orgasm, the fantasies that got you there burst like bubbles, and the reality of your exposure hits you like a two-by-four to the head.

"Well, I, I just assumed, umm..."

"Well," Jade said, slapping him gently on his cheek, "don't assume anything. You're a big girl and you're going to serve me the rest of the evening as you are. Wine please."

"I see," he said, "Well, this is not exactly what I expected I guess."

Jade turned to him, incredulous, saying, "What? Are you serious? Really? Did you think all this was for YOUR fantasies? Get that out of your mind right now. I want you to serve MY fantasies. Yours are secondary. It just so happens that many of our fantasies are common to us both, but not all. There will be some that you have that I will never fulfill for you."

Then she smiled and squeezed his cheeks together and added, "But believe me, ALL my fantasies will be fulfilled by you for me. You can count on that. Now for Christ's sake, get the wine and stop moaning!"

So, now that the fantasy bubble had burst, Darren finally got it. So this was to be his future reality. His jaw went slightly slack and he lowered his head. In the only gait he could manage, he slowly made his way out of the bedroom and entered the living room. It was dark, but the light switch was on the far side of the room, so he continued carefully. By the time he entered the family room, the anal device had already inflamed his desires once again and the fantasy returned.

Suddenly the lights went on and he blinked in astonishment as several women jumped up from behind the sofa and yelled, "Surprise!"

Within seconds they were swarming him, inspecting his skirt and blouse, and in particular, the bondage device he was locked into. Jade entered from behind and said, "It's very secure. He can't escape."

The brunette said, "Wow! I had no idea how helpless this made a slave. Amazing!"

Darren turned to Jade, his face the color of the forgotten sunset, and said, "Jade? Please...I...umm...Fuck!"

"Darren, you signed the contract. For God's sake, lighten up. These ladies are my friends from the club. And they're thirsty. Get the wine like I asked."

He teetered on his high heels, his legs wobbling in their spread. His hands useless hands hung from their chains. He quickly added things up and realized he was screwed, so he said, "But, how? I can't use my hands very well can I?"

"Well, I suppose..." she said and unlocked his wrists from his neck. Now off you go. Careful sweetie. Stay healthy. We want to use you later, so all this'll be worth your while."

They all laughed as the tent was building in his skirt. He turned and left in an agonizingly slow retreat, cameras flashing behind him. Arriving in the kitchen, he noticed several bottles of wine on the counter, a platter, and wine glasses. He returned to the family room to mock cheers, as they lifted his skirt and felt his cock or grabbed his ass as they pleased, a piece of sexual meat for them to play with.

And he was okay with that. Confusion reigned in his brain, humiliation, shame, lust, and ruling all from above was the contract. Yes he could leave, but with what? And the pictures they were taking...what would become of those?

The enormity of his contract decision made him breathe in short breaths.

Later, standing in the kitchen, exhausted after several trips with drinks, he was thinking to himself, so, this is it then. This is really it then. All the ways out of this were bad news. He was clothed in a skirt and blouse, impaled, and penniless, like the lawyer had warned. Yes, he could leave. But he could not leave tonight. They had him tonight.

Then he bent over and felt the anal plug find a new position. It pressed and rubbed relentlessly on his prostate now, creating want and need that only Jade could fulfill for him. He needed her. Oh God, he needed her. He needed her to feed his addiction. The fix was in, and there was no resistance left. This one hit of morphine had him. There was no going back. Not tonight.

Not ever. The echo was faint but clear.

He loaded his tray one more time. It had become strangely quiet in the other room. When he entered, there were only two women left, and they were naked and waiting for him.

"Come here baby," cooed the brunette, "We're going to lay you down on the floor and fuck your brains out, but according to Jade, you're not allowed to cum. We need you to stay hard for us. Is that clear?"

"Yes ma'am," he said in submission. It was better to seek forgiveness for cumming than permission.

He lasted as long as he could, two mounts by each of them. Then the brunette mounted him again while the sandy haired one mounted his face. He looked up at her breasts bouncing as she rode his mouth and tongue.

Sometimes it works this way. The brunette grasped the other's breasts. She in turn rolled her head back as Darren found her spot with his tongue. Darren, watching her, thrust his hips and pounded into the brunette. It was too much. They all came at once, screaming and moaning, bucking and writhing, eventually calming to rocking motions and low moans.

The silence was broken as the brunette whispered breathlessly into the nameless sandy haired girl, "Get off. I need him."

Darren was glad this was happening as he was being deprived of breath by her vagina sealing his mouth. But it was soon replaced by the other vagina dripping with his own juices, as she ground it into him. He had no choice but to taste it and lick it and swallow it as she gave orders above him, "That's it. Oh yes, clean it all up baby. Yes, clean it...up, yes, yes, oh, oh..."

She came again and he broke, he broke like a dam, but mentally, as he wept openly and uncontrollably in realization of his new status in life. It was not sadness; it was not happiness; it was something else: a sense of purpose, of being, of being useful as a sexual object. He didn't care how perverted that was, how perverted he was. This was what he wanted. This was what Jade wanted. He wasn't hiding any longer.

He was out.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • The Contract Ch. 02

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 637 milliseconds