Sissy Denial Pt. 03

Tom woke up the morning after the night he had partook of his first cock.

His boss had left once the afterglow of fucking Tom's mouth had waned. Tom had been in shock and a state of heightened sexual tension. He had had a cock in his mouth. It had been lovely. It had shot cum all down his throat and he had swallowed... not that he could have done much else, to be honest/ But still...

Tom giggled at the thought.

He had slept in his knickers. His cock was shrivelled and limp. He liked it like that... very clitoris-like. Or at least that is how he fantasised it.

His boss had told him that he would be back today, so get some sleep and wash.

Tom got up. Well, he leapt out of bed to be fair and skipped to the bathroom to get a shower.

About 2 hours later, Tom was sitting on his sofa, still wrapped in a large towel, listening to music when there was a knock at the door. Tom shook his head clear, stood and padded to the door. He opened it and there was his boss with a bag.

Tom stepped to one side as his boss walked in and shut the door behind him. He followed his boss into his own living room.

"Good sleep?" asked his boss.

"Yes. Thank you." replied Tom, suddenly a bit shy.

"Good. Hope you have been thinking about what happened last night?" His boss stared at him as he spoke.

Tom got more nervous and simply nodded, quickly.

"That's my sissy" said his boss, smiling.

There was silence for a few seconds, just long enough to be noticed. "I have some things for you. In here" and his boss indicated the bag.

"Oh?"

His boss placed the bag on the table, by the side of the sofa and unzipped it. He rummaged around until he found the electric clippers.

"Go into the bedroom and use this on your body. Get rid of all your body hair. Use a razor afterwards to get smooth."

Tom stared at the clippers for a moment. He reached out and took it and walked to his bedroom. As he opened the door his boss shouted "and don't be too long at it."

About 40 minutes later, Tom walked out of his bedroom and his whole body from the neck down was smooth. Everywhere was clipped and then shaved. He had never done his whole body before. This was the first time for his arms. He had done his legs and torso before, a few times but had stopped as no-one got to see the result and he couldn't be bothered to shave every day or so. Now he had a reason.

His boss had set out some more stuff on the table. He handed Tom some red nail polish. "Use this on your fingers and toes." Tom returned to his bedroom.

Next was a pair of fishnet stockings and a black garter together with an ankle bracelet.

Next was a metal cock cage: a rather small one that his boss put on him as Tom stood there, in silence. He had never purchased a cock ring. He had thought about them but again, he had no-one to wear it for.

The ring opened and closed around his smooth balls and the cage compressed his cock, so it pushed into his belly and clicked shut, keeping his cock a short length. Tom took a breath and looked down at it. He loved the idea of it: he could feel himself stirring already and the cage was constraining it well.

His boss gave him a new thong and bra, which he put on. Then came the item that drew an intake of breathe from Tom: a new corset. It was boned properly and soft to the touch and black.

"Turn around, sissy" ordered his boss and Tom swivelled. His boss stretched open the corset and wrapped it around Tom, stretching it a bit further until the fasteners could close at the front. His boss began to pull the lacing through the eyelets and Tom felt his stomach pushed and pulled into an hourglass figure. His boss pulled further until he was satisfied with the shape and fastened it with a double knot.

Tom found it hard to move properly and his breathing was shallower but he loved the feeling of the constriction on him.

"There. Now that is a sight" said his boss, looking him up and down. "What a transformation".

Tom felt himself blush and he ran his hands over his newly created waist line. He hoped that his hips and bottom were enticing for they felt enticing, at least.

His boss suddenly jumped and went to the bag again. "I nearly forgot these..." and he pulled a pair of open toes sandals out. They had a 3 inch heel and ankle straps.

By the time his boss had helped Tom put them on his feet - he couldn't bend down to do it himself - he stood there, taller than usual feeling very sexy and turned on. His thoughts went back to last night and then wondering how much would happen now.

His boss sat down on an upright chair and motioned for Tom, who approached. "Come and straddle me, facing me" said his boss.

Tom did so, sitting across his boss's lap and placed his arms around his boss's neck.

"Now, enjoy." said his boss.

And so began the following...

His boss began to caress Tom's body with gentle fingers, up and down his shaved arms first - which brought shivers from Tom - which gradually moved to his neck and head, massaging his scalp and squeezing his scalp. Fingers ran down Tom's back and over his buttocks. His boss squeezed his buttocks and then hands moved back up his body.

His boss began to kiss Tom - on his neck and shoulders, bringing more shivers from Tom. As he held Tom, his boss again moved his hands down Tom's body. This time they played around his thong, sliding a finger inside the material, running a finger along his crack and then around to rest on his belly before sliding down to rub him on his smooth perineum simulating rubbing and fingering a pussy. Tom moaned and groaned and moved his hips in sync with his boss. Tom was lost in the moment, resting his head on his boss's shoulder and holding him tightly.

His boss was very skilled with his fingers and soon one was being pressed ever so slightly over Tom's anus, to which his boss whispered "this is your cunt, sissy" in Tom's ear. The delicate pressure brought intense feelings from Tom who was moving madly about in response. He gritted his teeth at the intensity of the feelings drawn from the touches around the spot. He had never had such powerful reactions to anyone touching him anywhere on his body before. He was in shock.

All the pressing and rubbing around his cunt, as his boss called it, was spectacular. The delicate touches made Tom light-headed with the building pressure in his body.

His boss withdrew his finger to spit onto the fingers. They returned to the same spot, this time wetting his anus enough for a finger to slip into the sphincter. His boss began to finger the entrance in little thrusts, always teasing and going a little further inside occasionally, bringing still further gasps from Tom whose bottom was moving freely now in response to the workings of the fingers of his boss.

Throughout all of this, his boss kept talking softly into Tom's ear, whilst nibbling it. Words of encouragement. Words to cajole Tom. Words to make Tom respond in the way his boss wanted. Tom loved it all and was eager to please his boss. Nothing was too much for him now.

All in all, Tom was being taught how much his body could be switched on by a touch, a word, a kiss and Tom absolutely loved it. He couldn't believe his body was capable of this. And the most surprising thing - throughout all of the working on his body, he realised that his cock was still limp behind the confines of the cage. He also knew that he wasn't bothered that his cock had not been touched - he much preferred the finger in his bottom, any day.

Tom was prone in his boss's arm, resting heavily upon his shoulder and chest. Tom's hips were moving as his newly-named cunt was being fingered and caressed. Tom's eyes were heavy, his breathing deep and he was moaning and whimpering without knowing it. That finger was driving all sense from him. God, it was a powerful feeling.

His boss was still talking to Tom, telling him what a good sissy he was; how sexy he looked and how hard his own cock was now. Tom could feel it pressed against him and it made his mouth water in anticipation: he wanted it so badly, more than anything else, ever. Was this how women felt, he wondered, as he redoubled his hip movements on the finger buried inside his cunt.