Roleplaying Babysitter
By: Date: 2022.02.06. Categories: Sex Stories Tags: , , , , ,

Fantasies are meant to be exactly that… a fantasy! By sheer definition, they are unlikely to ever come true as they often possess the most outrageous series of events. This is one that remains firmly ensconced in mind; destined to remain a mere fantasy… for now!

“That’s the door. I hope you’re ready for bed sweety,” called Ian, as he finished laying the table.

Tonight was poker night. Ian was my babysitter; a 20 something guy who agreed to look after me all night! He was 5’11 and muscular, a hairy chest and rough hands. He was also a good friend. I didn’t exactly need a babysitter – I was nearly 30 after all!

“If you’re in bed in the next five minutes I’ll come and read you a story before I turn out the lights,” Ian called again, as he opened the door to his waiting friends.

I was dressed in a little nightgown, a long robe with a cord tying it at the front. I might have been nearly 30 but I was soft skinned and hairless, having made sure to shave ‘everywhere’. I could hear Ian’s friends filter in to the house, dropping their beers onto the poker table and dividing out the poker chips. I wanted a quick look; I didn’t know who Ian had invited over!

Five other guys aged between 20 and 45 milled about the table, already swigging from opened bottles and cans and flicking money onto the table to buy the chips. Ian saw me standing at the doorway and excused himself from the group.

He came over to me with a scowl on his face; his hands on his hips and one foot tapping irritably on the floor.

“That’s not being ready for bed now is it?” he mocked. “Naughty girls don’t get bed time stories do they?” he went on. Despite being a guy myself the illusion was kept up as much as possible! Ian was so convincing I had to remind myself that I was a man!

Ian walked me back to the bedroom and slipped me into bed. He pulled the covers up before moving to turn out the light. As he made to leave the room he turned and stood in the open doorway. His face was largely silhouetted but I could make out the look he gave me – a wicked glare that would likely terrify any normal person!

I knew what was going to come from this evening – that alone meant I was far from normal!

About an hour into their game of poker I decided I needed a glass of water. I shuffled out of bed and corrected my nightgown. Trembling slightly with a mix of anticipation and the cool air flowing breezily up under my robe I made my way to the room Ian and his mates occupied.
“Ian, looks like your charge is breaking the rules,” said one of the guys; the oldest man there. He looked a bit like Ian, with rugged hands and a rugged face, a greying head of hair and greying chest hair poking up under his chequered shirt.

Ian turned and saw me. He stood up and glared at me.

“What have I told you about coming out of your room?”

Ian unbuckled his leather belt and rasped it over his palm. I could see his mates’ faces; each one of them leering at me with pure lust in their eyes. I knew that any one of them would welcome the chance to take Ian’s belt and ‘punish’ me.

This game between Ian and me had been toyed with previously. We’d never gone through with it though, despite playing it over in our heads a dozen times! We were mates and both curious but neither had actually ever been with another man before! The exhilaration for me was not knowing which of Ian’s mates was going to be the one to ‘put me back to bed’. For all I knew, it might be Ian himself. I certainly wouldn’t have minded. If I was ever going to ‘be’ with another man I could easily imagine it being him. I’d seen him naked at the changing rooms to the gym a bunch of times and frankly I liked what I saw! He had a toned body, hairy and butch. His cock looked enormous when flaccid; I could only imagine what it would be like rigid and wanton.

“Go back to bed sweety,” Ian said coldly. The tone in his voice was unlike anything I was used to.

I retreated to my bedroom and slipped back under the covers. I was nervous and excited at the same time! I had often imagined being with another man and would regular wank off at the prospect. Usually, however, once I finished wanking the feeling would subside and I would lose interest. That was why we went to such lengths with this elaborate game – once the ball was set in motion, so to speak, there was no stopping it! I knew that I wouldn’t be able to allow the sudden change in feelings to subside and that no matter what I was going to experience sex with another man tonight. I just didn’t know which one!

Of all Ian’s mates I fancied the idea of being with two of them, as well as Ian himself. Dave and Simon were both in their late 20’s and were more like me in shape and size. They appeared as one might imagine the stereotypical nerd to appear; only I suspected they were a little more adventurous than others! The older man I had never seen before nor knew his name. The other two guys were in their 30’s, one was short and stocky, the other taller and more gangly.

I could hear the derisive laughter and lewd comments muffled through the thin walls of my bedroom. Apparently they were deciding who would be the one to ‘break me in’.

Suddenly a figure appeared in the doorway. With the hallway light on I could make out his outline but seconds later the light went out plunging me in total darkness. Now I had no idea who it was – which is exactly what we had planned.

“You’ve been a very naughty girl,” said the familiar voice. It was Ian!

I wanted to say something to him, to get his assurance that he was alright with this. I wanted to ask him if he was as excited as me or as nervous! I heard him stride into the room and up towards my bed.

“On your knees,” he demanded.

I slipped back the covers and got onto my knees. I closed my eyes and gasped eagerly as I felt his hand rub over my front. My silken robe made my skin tingle as his forced touch caused the material to rub my naked body.

I trembled with utter exhilaration and an equal measure of desperation. I so wanted to do this. I had dreamt of nothing else for years! Despite all the girlfriend’s and one night stands I would always revert back to this fantasy – to be with another man!

Before I had a chance to dwell on it further a hardened cock touched my closed lips. I stiffened as I felt it and slowly, and apprehensively, opened my mouth. It was like an explosive release; a sense of ‘at last’. I had a cock in my mouth for the first time.

It was hard and soft at the same time. It felt almost rubbery, like a dildo, yet was unmistakably the real thing. I clenched my eyes tightly shut; a futile effort considering the lights were still out. Eventually I allowed myself to relax! I began to actively bob my head back and forth, taking Ian’s hard cock into my mouth. It felt exquisite as his hardened muscle filled my mouth.

I had already lost track of time; hungrily taking his massive cock. I tentatively reached out my hand and cupped his heavy balls. I circled them in my palm and stroked them whilst still swallowing his member. At that moment, despite never having had a man before, I desperately wanted him to throw me onto my back and slide into my virgin rear. I wanted to feel his hot semen all over me, devouring me and completing the sense of naughtiness that overwhelmed me.

I couldn’t have known what was to follow!

I continued slurping happily on Ian’s large cock, imaging newer greater sensations when I suddenly felt my nightgown lift up at the back. I was on my knees but bending forward, as I was kneeling on the edge of the bed. Suddenly I felt a finger penetrate my anus, sliding deeply into me! I nearly choked on Ian’s cock with the surprise! It was physically impossible for Ian to be able to reach me and insert an entire finger as I sucked on him – I would have felt his torso contort with the effort. It had to be one of the other guys!

The finger began sliding in and out of me rapidly, my ass tensing with the pumping sensation. I began sucking at the same speed, matching the rhythm as best as possible. The finger fucked me so fast I lost control of Ian’s cock and had to grope about in the dark to put it back into my mouth.

Suddenly the finger was pulled out of my ass! In its place my ass was stretched by a hard cock. Mercilessly the cock rammed into me, filling my hole and causing me to grimace. Again I lost control of the dick in my mouth using both hands to support myself under the weight of the guy behind me. My whole body tensed as I felt Ian’s mate slide his member in an out of me. It was slow at first but sped up when he was satisfied I was comfortable enough to receive him.

This went on for many minutes; me trying to keep my balance on the edge of the bed whilst being roughly taken from behind. The sensation was amazing; overwhelming and completely fantastic! I desperately searched with my mouth for Ian’s cock and when that failed I dared lift one hand to find it. His dick was moist with my saliva but still weirdly rubbery. Before I had a chance to slide Ian back into my mouth I felt another cock slam into my face. A third one?

I panted with the effort of sucking this third guy whilst still being fucked and gripping tightly to Ian’s cock in my hand! I managed to support my weight on my knees alone and used both hands to alternate the dicks in my mouth. I wanted them both and wanted the guys behind them to know it too!

Another pair of hands, possibly belonging to the other guy I was sucking suddenly pulled on the cord holding my robe together. My robe was pulled apart revealing my erect cock! The second cock suddenly exploded, hot jizz splashing over my exposed torso. I could hear his grunts as he milked his cock on me, every last drop tingling my skin.
And then, almost simultaneously, the cock in my ass fired its hot load as the cock in my mouth unleashed its own arsenal of manly milk. I almost gagged on it. I balked at the idea of tasting cum, never even daring to try my own as old mates used to suggest jokingly. But here I didn’t have a chance. Here I was forced to keep sucking as the heavy cock unloaded its round into my busy mouth.

My ass burned at the same time. I could feel the guy fucking me tense up and grunt repeatedly as he fired his load. In the same manner, the cock in my mouth was accompanied by similarly grateful grunts of relief; grateful for being able to release so messily.

All three cocks moved away from me. I was left lying on the edge of the bed, my robe pulled apart and left dishevelled. Hot cum dripped from my ass and trickled over my torso. I had little choice but to swallow the load in my mouth and could only lay still puffing and panting for air.

“That’s what happens to naughty girls,” said Ian as he closed the door behind him.

Second later the door opened again.

“Don’t make me show you what happens to ‘really’ naughty girls,” he said evilly.

If that was anything to go by, I thought, I was going to be the naughtiest ‘girl’ alive! Or at least I would, I conceded, once I was fully recovered.

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