Role Play

Last week I got talking to a young guy through a swingers website, his name is Jordan, he's 23, and like me he's in to sub/dom switch play. He's a CD, a foot and leg fetishist among a host of other things.

We met up last Friday for the first time, nothing happened, we had a drink and agreed to get together on the Saturday at my place. It was a lot of fun and we had a great time playing together and getting to know what we like and don't like. We spent hours playing around, dressing up, and switching roles before having any kind of sex. That's one of the things that I love about role playing, it can go on forever and we just got so caught up in it.

He came back to my place on Sunday afternoon and it turns out that we both have a lot in common when it comes to bondage games and, of course, sex. Again we had a great time together and decided that we will have regular sessions.

I was at a meeting at the bank yesterday and even though I should have been concentrating, my mind was all over the place, I couldn't stop thinking about the fun we'd been having and straight after the meeting, I decided I'd have a mid week half day and call on Jordan to come brighten my day up. For some reason I hate Wednesdays and felt like I needed some fun.

I had already started on a bottle of wine and *********** twice by the time Jordan turned up, so I was in a very good mood by then. There was no rush so we drank and talked for a while. It was decided, through our conversation, that I would play the Dom role first and it was a role I hadn't played for some time. He was very specific about what he wanted to do and it had to be done properly. But basically, he wanted to be sissified and have me **** him with a strap on.

He went off to the bath room to get changed and I went to the bed room to get changed in to his choice of wear. He wanted me in nothing but black tights, my black leather boots and of course the strap on. The strap on belonged to him, it was a quality product, much better than the one I have and it came with a nice glossy black 8 inch *****. Well, I was ready to go in no time and told him to come down stairs when he was ready.

I was stood waiting for another 10 minutes and on another glass of wine when he came into the living room. He'd made quite a transformation while up there. It took a minute to take it all in. It was the makeup that threw me for a second, he could have used my help there, but it was quite well done for a guy. He was wearing a little blue and white bo peep dress, white stockings and flat black shoes. His long hair added to the girly look and he looked quite a convincing girl, a bit over the top with the makeup, but still convincing. Now it was time to have some fun and get into my role.

With some teasing and taunting I hand my little man ***** bend over the side of the chair for a spanking that she admitted she was in need of. At first she'd tried to resist, but I soon had a grip of her hair and had her bend over as instructed. I lifted her dress, pulled her little white panties down and delivered a damn good spanking to her bum. Of course, she squealed and whimpered with every strike, pleading with me to stop, telling me how much it hurt, but I continued to thrash her arse. The pleading went on, I gripped her hair and forced her to suck on my **** and all the while she denied enjoying it.

That's when I decided it was time for this little man ***** to get a *******. The pleading was becoming more and more elaborate as I slipped a lubed finger into her arse hole, telling me to stop and saying that she didn't deserve this kind of treatment. Of course, more spanking followed and by this point her arse was red raw and stinging. So, I lubed the ***** up and told the little ***** to stop her ******* moaning. The moaning and squealing only got worse as I poked the ***** in to her arse hole, her **** was rock hard and ******* about as I went deeper in to her. I fed the whole length in to her and ****** that little man ***** hard, and oh my gosh, she was ******* squealing like a little pig. I had her lay on the floor, on her back, and again ****** her hole hard, her **** ridgid it spewed a lush jet of ***** on to her dress and I made the little ***** eat some of it.

Ha! It was such fun being in that role and I want to do it again this weekend. I'm so happy I found Jordan and I'm enjoying our time together. Time well spent I say. It's my turn to play the sub on Saturday and I can't wait.
deleted deleted
26-30
Jan 17, 2013