Plenty has been said about Jessica and her excellent massage plus services. I have visited her several times and always enjoyed her enthusiasm and willingness… especially as she seems to thoroughly enjoy exploring my receptive ass.
My ambition for a while now has been to see if we could progress from her just rimming and fingering my bum, to getting her to use my favourite strap-on on me. And at last we got there.
It was a Friday evening, and I had booked an hour and a half. I prefer the longer sessions as it gives both of us enough time to relax into things. The usual collection of the great unwashed hanging around outside, but Im old enough now not to let this bother me. Inside Jessica was warm and charming as always. After several visits she knew what I liked and seemed to enjoy our time together. Money paid, and up into her massage room, and onto her table, but before I lay down I placed my beautiful strap-on onto the chair, where I knew she could see it. She did notice, but said nothing and the massage began. She remained clothed at first, but we both knew that that would change soon. As usual the massage focussed on cc swipes and gentle rimming - as I said she knows what I like - and I was arching my back and raising my bum and making the usual (genuine) appreciative sounds as she gently probed and explored my ass.
A good 20 minutes of this followed, and then without needing to say anything she squeezed out of her leggings and dress leaving just her panties on - she also knows I am a total panty fetishist! As she did this I took the opportunity to get off the table and pick up the strap-on. She has a cute little giggle, and looked curious and slightly confused at first, as I showed it to her. “Please - can you put this on?”. I could tell that she knew what I was after, and seemed to be unsure for a moment, but after a brief pause I got the answer I wanted… “Ok! I be your boy - you want to be my girlfriend?” and then she was giggling and making appreciative noises as we fastened the belt around her waist and tightened the straps between her legs over her panties. It is a particularly attractive strap-on with a brocade material and a wide support on the waist and I knew from previous use that the straps that passed between her legs would rub in just the right way if they were fixed well. When it was finally fitted on her, she stood back and I could see she was admiring her new appendage in the mirror. She twisted and viewed it from a different angle. “Mmmm… Im a boy now!” She seemed to be enjoying the experience, and her lovely little giggle was a joy to hear.
I had brought 2 dildos, one a small but beautifully realistic cock, and the other a slim, curved probe, about 5 inches long. Just perfect for the initial opening up of my ass. It was this one that we started with. I had made sure that I was clean and prepared beforehand, with a healthy dollop of vaseline inside me. I had had a butt plug in earlier as I drove to Doncaster, so I was ready, willing and open for business!
The next hour or so were exactly as I had fantisied they would be. Like many woman in my experience, she genuinely seemed to enjoy the sensation of doing the fucking rather than being fucked, and although at first she was a bit unsure how to actually build up the right consistent rhythm, she was enthusiastic and keen. We started with me face down, and as we progressed she become more confident and bolder in her new dominant role. At one point she was using her full weight to hold me down while she thrust into me, and I really felt that she taken control and was going to fuck her bitch for as much as she wanted to. We switched into several different positions… face up with my legs on her shoulders… bent over the massage table… back to face down and bum up in a doggy pose (she seemed to particularly enjoy that - I think the straps that were pulled tight between her legs were rubbing her in just the right way). It was a wonderful experience for me, especially when after a short break we switched to the larger dildo cock, and after applying another good gloop of vaseline she began to penetrate me deeper and harder as her confidence grew. I have been fucked by quite a few woman, in quite a few different ways, and although this was not the best strap-on play I have ever had, it was still good. I become a complete slut when Im being fucked, and the only limit comes when I dry out or it just feels enough.
When she had finished with me… (it really did feel that she was the one who was controlling the experience) we just lay there kissing gently with her still inside me, but still and silent. She had built up a slight sweat, and when I slipped a hand between her hands I could feel the dampness in her panties. “You like that?” I hardly needed to ask the question. “Your boyfriend fuck you good yes!” she replied, and then that sweet infectious giggle again.
The final minutes passed in the way that we always finished. She sat on my face and I made sure to lick her to an orgasm, as I finished myself off by hand.
So - another tick on the bucket list… and hopefully to be repeated. I paid her the £70 for the 90 minutes, plus an extra 60, which she seemed happy with. I genuinely think she enjoyed her brief role reversal - I know I certainly did, and I drove home to Lincoln with that content satisfied feeling of having been well and truly fucked and used. Maybe next time we will explore even more of my feminine side… there is so much more to explore!
