Cherry 22

This is a story about an aggressive transsexual and a submissive man so if that's not your thing then there's no point in reading any further. That's why this story is in non consent not transsexual. You would hope there isn't anyone like her in the real world but it's always possible. You just wouldn't want to meet her.

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The doorbell rang and Cherry took her time answering, letting him stand at the front door waiting, knowing he would be wanting to get inside quickly. He wouldn't want someone to walk by who knew him and enjoyed the thought of his discomfort. She opened the door and, with a gesture, invited him in. "Hello Walter. I'm Cherry. Let me take your coat," she said, in a voice that would get his already eager cock twitching even more.

She looked him over with a practiced eye. About five foot seven; about forty pounds overweight; almost completely bald; very short sighted judging by the lenses in his glasses; total lack of confidence; and probably a little cock to go with it.

He looked at her and saw a very attractive lady who stood about three inches taller than him in her four inch heels; cropped blonde hair, slim body and wearing a short leather skirt with a white tank top.

Taking his hand she led him into the bedroom. "Would you like me to undress you or will you do it yourself?" she said, in a soft sweet voice.

He stuttered and, in a whisper, said, "no thank you. I'll undress myself."

"Okay, Walter. You just take your time. Do you have something for me?" He looked surprised and then, as it dawned on him what she meant, he removed the envelope from his jacket and handed it to her. "Thank you Walter. Whenever you're ready we can begin."

He undressed and she saw that she had been correct about the size of his cock. It was already erect with anticipation and three inches long, thin, and with balls the size of dried prunes. He couldn't even see it because of his overhanging belly. To get that inside me, she thought, I'd have to be on my back with my knees touching my shoulders. She put her arms around him and, although the thought made her feel sick, gave him a warm lingering kiss. Leading him to the bed she sat him down next to her. "How about we begin with tie and tease, Walter? When we spoke on the phone you said you liked tie and tease."

"That would be perfect. I must say you are very beautiful, Miss Cherry."

"Thank you, Walter. It's always nice for a girl to get compliments."

She laid him on his back and, lifting his hands above his head, pulled them apart and handcuffed them to the bedhead with velcro cuffs.

"Has a blindfold been used before when you've had a lady do a tie and tease?" He nodded and she continued, "then we'll use a blindfold this time, Walter." She quickly put the blindfold on him and then produced some earphones. "I'm going to have you listen to some music while I get everything ready."

Leaving him lying on the bed, unable to see or hear, she started going through his pockets and wallet. She took her phone and photographed his driving licence; a letter with his full name and address; details of where he worked; an in-case-of-emergency card showing his wife's name; and then replaced everything. Picking up a feather duster, tickled his feet, and he immediately began to giggle. She removed his earphones. "Did you enjoy that Walter?" she asked still keeping the same sweet tone to her voice.

"Yes, Miss Cherry. You took me by surprise. I expected you to remove the earphones before we began."

"Well, we've done the tie and we mustn't forget the tease must we, Walter?"

She tickled him under the arms and then moved down to tickle his cock. Putting the feather duster down she licked the end of his cock, sliding down to his balls, and then swallowed his cock whole. With such a small cock it wasn't a problem. She'd deep throated cocks three times the length and much thicker. Walter moaned with pleasure as she sank all the way down his little shaft and grazed it with her teeth as she came back up. She put some ice cubes in her mouth and then took his cock in her mouth again. Boy did he react!! His arse jumped off the bed as if he'd been poked with a cattle prod.

"Did you enjoy the ice, Walter?"

"Yes, Miss Cherry. No one has done that before. It was a surprise, but very enjoyable."

She looked down at his tiny shrivelled pathetic cock and, with difficulty, stopped herself from laughing. "The fun has only just begun. Just lay there. I'll be back shortly. I'm going to replace the blindfold, just for a moment, while I get ready for what comes next." When she returned she was completely naked, eager, and ready for action, adrenalin pumping in anticipation. "I'm just going to tie your feet. It'll make the next part even more enjoyable."

More enjoyable for me, she thought, but not for you. You pathetic fat little excuse for a man. She pulled down the ropes from above the bed and secured the cuffs around his ankles. As she pulled on the ropes his legs were raised and pulled apart and she tied off the ropes when his feet were above his head.

"Nearly there."

"This is hurting me, Miss Cherry. Please untie me. I've had enough of this tie and tease."

"I'm going to put a pillow under you to make it easier." Easier for me you fat pig! She swung a leg across him, sat on his chest, and removed the blindfold. Walter's mouth dropped open when he saw a cock hanging over him which, although flaccid, was still five inches long. "Surprise, surprise. Not quite what you expected? Someone is going to get fucked but not the way you expected." His face had gone as white as a sheet.

"What are you going to do?"

She smiled down at him and then her lovely lips twisted into an evil grin as she snarled,"you're going to find out why my name is so apt. Because Cherry is going to take your cherry. I'm going to fuck your arse, Walter. When I said the next part would be even more enjoyable I meant enjoyable for me not for you."

"No! No! No! Please don't do this to me, Miss Cherry!"

The tears started rolling down his cheeks as he began to cry. She stroked her cock and within a few seconds he was staring at eight inches of solid meat. Without thinking his jaw dropped and his mouth opened which gave her the perfect opportunity to slide between his lips. His automatic reaction was to clench his teeth around her cock but when she immediately slapped him in the face he quickly released her. She backhanded him hard! Very hard!

"If you do that again you'll be going home minus your teeth and without something else as well! Now take a deep breath and open your mouth." He was so frightened he opened his mouth as wide as it would go. She rammed all eight inches down his throat, bypassing his gag reflex completely, with one thrust. Pulled halfway out and then rammed it all the way in again. After holding steady for a few seconds, but for what must have seemed like an hour to him, she withdrew.

"Breathe, and breathe again, at every opportunity. Next time I go in I'm not stopping." With that she began to relentlessly fuck his throat with a savagery Walter would never have thought possible. His breathing became more and more ragged, tears cascading down his cheeks, and he started sobbing. She removed her cock, and stuffed a pair of panties into his mouth. "Suck on my panties. They are a pair I wore earlier and pissed in. I also had a shit and didn't wipe my arse properly. Wine and chocolate just for you. Enjoy the taste my little piggy boy."

She knelt down, snapped on a latex glove, and opened a bottle of lube. Pouring some onto his balls, she watched it slide down to his fuck hole. She pushed it in with a finger, poured on some more, inserted a second finger and worked it inside him. A third finger worked more lube in. She listened to his muffled moans. Is it pain she thought? She laughed to herself and thought, I damn well know it's not ecstasy! Standing up, she lubed her cock, all the time staring at him and taking delight at seeing the terror in his eyes. Kneeling down between his legs, she held the head of her cock ready.

"Just relax and it will be easier for you. Admittedly this is going to hurt you a lot more than it will hurt me! Actually I'm lying because it's not going to hurt me at all. Push out as if you want a shit. It'll open your sphincter and make it easier for me to enter." As she pushed he automatically resisted. She felt his resistance and lost her temper.

"Relax and make it easy on yourself." But because of his fear he was unable to relax. "Okay, you useless cunt, you asked for it," she hissed as she threw all her weight onto her cock and rammed in the first three inches. With the next thrust it all went in and her balls slapped against his skin. She slowly withdrew until only the head of her cock was inside him. "Do you know what I'm going to do next?"

He shook his head.

"I'm going to fuck you really hard," she snarled, "I'm going to ram my fucking cock into your arse until your insides are raw. I'm going to fuck you until you're unconscious, wake you up, and then fuck you again. I'm not going to stop until I'm the one who is too exhausted to continue." With that she slammed into him again. The sweat ran down her face and her body glistened as she held his ankles up, pushed her body down, slamming her cock in and out of his hole.

"My cock and your cunt bitch! A real good combination." With that she hammered his arse with her cock again and again. It wasn't until she came to a shuddering halt, hanging on to his legs for support, she realised he was unconscious. How long he had been unconscious she had no idea. Nor did she care. He was just the provider of a man cunt for her to fuck.

She felt the wetness beneath her, and looking down, watched her cum drip out of his fuck hole. But there was more. On his chest was an unexpectedly large puddle of cum. Sometime during the time she'd been fucking him he'd come which was very surprising, considering the size of his cock and balls, and he'd shot a decent load. Collecting some cum on the tip of her finger, and after removing her panties from his mouth, she smeared it across his lips. When she got no reaction she collected some more, and this time pushed her finger inside his mouth, smearing it on his tongue. He opened his eyes, wondering for a moment where he was, and why he had that awful pain in his arse. As his mind came back to the present, he looked at her with a mixture of hate and fear.

"Open up baby. Clean up the rest of the cum you've spilt."

He suddenly realised what the taste was in his mouth, shook his head, and clamped his lips shut.

"Well if you won't eat it there's only one thing to do." She collected what was left of his cum and smeared it over his face. She smiled and said, in the sweet voice she'd used initially, "my little fuck baby, you should always clean up your mess for mommy. Have you had enough of Miss Cherry fucking your arse?" He nodded hesitantly, unsure of what was going to happen.

She leaned down and looked into his eyes, "too fucking bad, you little cunt, because I haven't finished yet!" She screamed and spat in his face! "I haven't finished fucking you and you have no say in what's going to happen! It isn't if you have had enough. It's if I've had enough! You're just a piece of meat to be fucked until I don't want to fuck you anymore!"

She removed the handcuffs, flipped him on to his stomach, pulling him back towards her until the tip of her cock was touching his rosebud. Leaning forward, she slid smoothly in and lay down on his still body, letting him feel her warmth and the softness of her skin. She lay inside him for a few seconds and then pulled almost all the way out before sliding every inch back in.

She felt him start to move under her but he wasn't struggling. It was more that he was making himself comfortable. She fucked him so tenderly that she might have been a different person from the one who, a few minutes before, had taken his virginity so savagely. All her aggressiveness had washed away. He began moving with her and she heard a quiet moan escape his lips. Then another. Every time she entered him there was a moan of happiness, and she couldn't prevent herself from letting him enjoy the moment.

The pain had gone and, like so many before him, he was experiencing the pleasure that can only be achieved by being taken by a beautiful and sexy shemale. He had entered her domain as a victim but now he was her submissive. He had gone from fighting her to loving the feel of a shemale cock inside him. He was hers now, and he would remain hers, for as long as she wanted.

Cherry released Walter from the handcuffs, slid off the bed, leaving him lying there while she went for shower. When she returned he was sitting, still naked, on the edge of the bed. His head was in his hands and he was softly sobbing. She retreated to an armchair and sat watching him whilst lovingly stroking her cock. Just enough to get it hard and tingling. She felt sorry for him, in her own way, which was unusual. The norm was for her to take their money, fuck them, and throw them out the door. Many times she kicked them off the bed, if she was in that frame of mind.

There was something about Walter, but what it was she couldn't say. He still looked pathetic, but not in the same way as he had when he arrived. In a strange way, and for some reason, she felt a little remorse for how she had treated him. Unlike many others who had gone before him. But she couldn't bring herself to express it verbally. She never would. Never!

"Walter," she said, and when he looked up at her, "you'll have to go because I'm expecting another client shortly. Do you want to shower before you leave?"

"It's okay. The house will be empty when I get home and I'll have a long soak in the bath."

She watched, as he slowly followed what was obviously his usual ritual for getting dressed. First the underwear. Then the left sock. Followed by his right sock. Slipped his arms into the sleeves of his shirt, left then right, and after buttoning it up he did his tie. Next came the trousers, into which he tucked his shirt. The left shoe went on and then the right. He stood up and slipped on his jacket. He was slow. Ever so slow. It must have taken him five times the amount of time it would normally have taken him.

She sat there in silence as he stumbled towards the door. He reached for the handle and then turned. "Could I come back and see you again sometime please?"

She was stuck for words as this was totally unexpected. Many clients always asked if they could come back to see her a second time. That did occur. Often. But with men more experienced and considerably more "manly" than Walter. But even looking at the abject figure he presented, she still couldn't bring herself to show any remorse, or appear apologetic, for what had happened.

"Yes." Just the one word that echoed round the room and then he opened the door, quietly shutting it as he left, and she heard the irregular footsteps dragging on the path as he walked away.

She looked up at the wall behind her, and there sat the camera with which she usually recorded all her sessions, because you could never be too careful. When she saw a client for the first time you never knew how they would behave, when they found out what she had hidden in her panties. She had also on occasion used the tape for blackmail. But for Walter the camera hadn't been switched on. She knew from when he had phoned, to arrange the appointment, it wouldn't be needed. After all, she had all the photos if she needed them for blackmail.