Written by Trainer

29 Dec 2017

It took over 30 minutes of chatting to Olive to convince her we should go to Diane’s room. Olive put up some real serious arguments as to why she didn’t want to and how she’d be seen by the women she worked with if they found out she had. I told her that as with any situation, no one could force her to do something she didn’t want to and with me there I certainly wouldn’t either try to get her to do something or let someone else do something she didn’t want to, finally I told her that if we went and she decided she didn’t want to stay then we would come straight out.

I knocked on the room door, we waited a while for it to be answered, but Diane’s ‘friend’ opened it by hiding behind it. Olive and I were greeted by one real interesting sight. Diane minus all of her top clothes was tied to the bed face up, on the bed beside her was a vast, like nearly 20 sex toys, spread on the bed. She had already had nipple clamps fitted through the slits in her bra. She gave us a little wave, then told Jade, her gf, to get us some drinks. Jade got two glasses from the bathroom and poured red wine for us, I told Olive to sit down. Diane now invited me to give her another of my tongue tickles, so I lay down between her legs and started over. I could hear Diane moaning but I could also hear Jade trying to entice Olive, who was having none of it. I lifted my head and told Jade that she should concentrate on Diane and forget Olive. Jade joined us on the bed, I was between Diane’s legs and Jade began on her breasts, chewing around the nipple clamps. I then heard the buzz of a toy, Jade had moved down the bed, I felt the vibration on my ankle as she started to work up my leg, slowly as I chewed on Diane’s sex, so Jade worked up my legs, I felt my dress moved and the plastic was moved around the tops of my stockings, now my dress was pulled right up over my ass. Jade let out a mighty yelp as she moved my panties, of course she was expecting to find two holes, instead she found out my secret. Diane asked what was wrong with her and Jade, somewhat drunk from the earlier party, stammered out that I had a cock. Diane couldn’t move from under me so I stuck two fingers in her and flicked my tongue over her clit at speed, at this point she sighed and told Jade and I to carry on, I moved up my cock now hard and hanging out of the side of my panties.

Jade restarted her rabbit, she was now running it around my ass. I pushed into Diane and not long after I felt a liquid dropped into my ass crack. The rabbit was being worked around my hole Jade was slowly inching it in. It wasn’t that comfortable, as I was still a virgin behind me, but I worked my way into this so I felt it would be wrong to pull out of this situation so I carried on chewing Diane and thought only about giving her her pleasure. I knew that Jade had worked the toy deep into me, but now I was aware of Olive standing beside the bed watching us. I then heard Diane tell her she should get a strap-on and give me what I deserved. I really wanted to look up and encourage Olive, but out of the corner of my eye I saw her dress lifting up she must have then picked a strap-on off the bed, Jade stopped working on me, to help Olive secure it in place and I heard her say she would put some more lube on it before I felt nylon rubbing my nylons and the toy was now being pushed into me. I stopped fucking and kissing Diane, not that she missed out, as I was still hard and Diane was moving under me enough for both of us

I had lost all sense of time and I’m not sure how long Olive fucked me I was actually in heaven a twenty something beautiful woman was shafting her cross-dressing client, I could feel myself beginning to climax and started to moan as she carried on. Afterwards she collapsed on top of me as I’d emptied into Diane’s sexpot. Olive slipped the rubber out of me and climbed off the bed I sat up and pulled her back towards me and kissed her passionately. After a while she said she wanted to go home and carry on in private. Diane told her as she dressed that she had a great future in her business and she didn’t see her as a target, but she would like another session at some point in the future.

We dressed, re-did our make-up, we both kissed Diane and Jade, then left to walk the short distance to get a taxi to get back to Olive’s flat, via my car to get my overnight bag.