Roleplaying Babysitter

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.

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