Sissy Denial Pt. 02

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Tom gets his first lesson.
1.1k words
4.7
7.6k
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Part 2 of the 4 part series

Updated 06/11/2023
Created 09/15/2022
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Tom moved into his bedroom and stood, shivering slightly with anticipation, as his boss came in and closed the door behind him.

His boss stared at Tom. Tom stared back. One was hungry with the thrill and the other hungry with the promise of a lifetime of dreams coming true.

"Stand in front of your chest of drawers," his boss told him. As Tom faced the wrong way, his boss corrected him "No, face the drawers. And lean on it with your arms. Good. Shuffle your feet back a little. There, yes."

Tom did what he was told, thrilling at being ordered. He hung his head down further as he felt a hand on his thigh, sliding up and down his leg. He stuck his bottom out a little more and waited.

The hand rose to his buttock and squeezed it. "Nice," said his boss who seemed to be sizing up a lump of meat. Tom didn't care.

Another hand stroked up Tom's spine, moving to his neck and held him there as the first hand slid from one buttock to the other, finally sliding a finger between his thighs and caressing him through his knickers. Tom groaned at the touch and gyrated his hips around slightly.

"That's it, sissy," said his boss. "Move around on my finger, like a good sissy."

Tom moved on the finger between his legs, rubbing himself on it, displaying himself for his boss in any way he could: he no longer cared. He was enjoying the role.

His boss moved his hands onto Tom's hips and held him there, pulling Tom closer and then pushing him away, simulating sex. Tom groaned more and hissed as his bottom began to slap into his boss's crotch. He felt the penis there, swollen and ready.

"You feel it, don't you sissy?" his boss asked.

"Hmmm, yes. I feel it. It feels large." Tom panted.

"Do you like it?"

Tom hesitated. Of course he did but he wasn't going to give in that easily. "I guess so." he said noncommittedly.

His boss laughed, squeezing his hips as he pulled Tom back onto his crotch harder, in a slapping motion. "Yes, you do, you dirty bitch. I can tell."

His boss let go suddenly, moving away. Tom stayed as he was, swaying slightly.

"Turn round and get on the floor on all fours."

Tom turned, paused and then got onto all fours, facing his boss. He looked at him, having to look upwards.

"Good, now come here and stop just in front of me" ordered his boss. Tom did what he was told.

"Now is time, sissy, to show me what you are really like."

With that, he unzipped his trousers and they dropped to the floor. Tom watched with fear, excitement and loathing... what a heady mix. His pupils must be so wide, he was staring so intently in front of him, fearing the moment but wanting it so badly at the same time.

His boss pushed his shorts down and his swollen cock popped out and up, standing at attention in front of Tom's face.

Tom looked at it and knew everything that was going to happen. He was straight. He was wearing lingerie and craving cock: this was the moment that he always thought about and masturbated to. He wanted to please his boss so much, it hurt at that moment.

"Now then sissy, lean over and lick everything in front of you. Just your tongue."

Tom melted inside and he groaned as he leant forwards, sticking his tongue out. It touched his boss's cock. The world carried on. No fanfare, no police, no laughter.

He moved his head around and began to slide his tongue along the side of the cock, then over the top of it, to slide back to the head. He licked the head. He smelt the muskiness of the cock and he tasted the precum that oozed from the tip.

He was licking it properly. All over. He worked hard to lick it. He moved lower and dipped and licked both balls as much as he could, even with the odd hair in his mouth. He licked to please his boss. That was the overriding desire... to please. He felt no attraction to his boss at all - he wasn't actually there in Tom's head. It was all about the cock.

Hands were placed in Tom's hair and guided Tom's head. Tom moved with the pressure, licking. Saliva was dripping onto the floor and Tom was revelling in the moment.

His boss held his head and began to move it forwards and backwards slightly, pressing Tom's lips against the head of the cock. Tom was preparing himself for that moment and it happened simply: his lips yielded and the cock slipped into his mouth, then out again.

He had had a cock in his mouth!

There it was again. And again. Again, again. Getting deeper, more urgent, faster. All driven by the hands on his head. His mouth was being fucked.

His boss was moaning but Tom had his eyes closed by now, trying to accomodate the cock in his mouth.

His boss stopped moving Tom's head and held it, with his cock still buried in Tom's mouth, his lips pursed around the shaft. His tongue rested against the underside of it.

His boss began to thrust into Tom's mouth. Now he was being fucked. Tom gagged a little as his gag reflex was touched. Once, twice. Again. He gagged and baulked, fighting the feeling of it. He pressed his head back at those moments but his boss's hands held his head firmly in place. He was fucking Tom's mouth quickly now. In and out. In and out. Mostly Tom coped, occasionally he gagged and fought.

Then, the cock changed slightly and Tom know the moment had arrived. He cringed and psyched himself for it.

His boss thrust roughly a few times, pushing himself deeper into Tom's mouth and then grunted and thrust twice.

Tom felt the cock erupt in his mouth - the wetness, the warmth, the saltiness, that weird metallic feeling as the semen flooded his mouth and he couldn't do anything but collect it in his mouth, finally letting it slip down his throat. He swallowed it all then in two gulps, reflexively and sucked on the cock more, eager for the rest. Anything more.

He worked his tongue, cleaning the cock. He sucked on it, drawing out every drop he could and he swallowed it all, eagerly. He surprised himself - he had never managed to swallow his own cum but this was different. He was so horny still. He wanted more. He would do anything for more at that moment.

This is what Tom had craved all his life. This realisation that he was a cocksucker. He knew he would never fancy the man but it wasn't the man who was important. It was all about the cock.

Tom had metamorphosised in that moment into a sissy cocksucker. He knew it and he craved it.

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4 Comments
awyldsideawyldsideover 1 year ago

There you go! Please continue

KatiwantsKatiwantsover 1 year ago

Mmmmmmmmm mmmmmmmmm sweetness!!!

dianefritz30dianefritz30over 1 year ago

Well written and i enjoyed it Yes the journey has begun and it never ends does it?

JgsexyJgsexyover 1 year ago

The journey has begun! Yummy!!!

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