Having returned home I still felt so aroused by the evening with George and of course still wearing the chastity cage and butt plug, with no panties, under my now cum soaked and very short dress. While I had planned to get home and tidy away all Rebecca’s things before the boiler man arrived at 9am, I had a new idea. I would instead be dressed as Rebecca and pretend to be my girlfriend. This had two benefits; one, it would save me a lot of time cleaning stuff away and; two, it was making me increasingly turned on by the thought. I stripped off my clothes removed and cleaned the butt plug but left my cage on, even though I had a spare key. It just felt so good. I had a shower before bed and managed to do a good job cleaning down there, despite being caged. I slipped into bed wearing just a short satin nightie and the chastity cage.
My alarm went off at 6am. I got myself ready, a white corset with beige 15 denier lace top stockings that had a black seam. I was still wearing my cage so skipped the panties. Over this I wore a blue, just below the knee, long sleeve dress with fitted bodice and flared A line skirt. I applied a very light and subtle makeup look. However, as I was still wearing the bright red false nails from last night I wore matching red lipstick. I put my hair up in a loose, scruffy ponytail and fastened on a matching blue lace choker. Instead of my usual ankle strap heels I slipped on a pair of kitten heeled ankle boots. I was trying for the ‘girl next door’ everyday, but sexy at home look. I think I managed to pull it off. As I looked at myself in the full length mirror I could feel my girly cock swelling against the restraints of my cage and the nervous, excitement and arousal of being about to meet a stranger as Rebecca building up inside me.
I made sure I left my makeup out in the bathroom and some of my lingerie scattered around the master bedroom. I draped some fully fashioned black seamed stockings over the bedroom radiator and left my cum stained black dress from last night on the bedroom chair to one side, the cum stains clearly visible. Finally I left my nightie on a pillow of the double bed. I was hoping it would look like I was the girlfriend staying here.
The boiler man arrived just before 9am and apologised for being a little early. He looked a little surprised seeing me so I gave a pleasant smile and said “Hi, Matt had to pop out and asked me to let you in. Hope that’s OK?”. He of course said it was no problem, trying not to stare but giving me a good look up and down. He said he hadn’t serviced Matt’s boiler before so could I show him where it was. I led him through to the kitchen and pointed to the boiler on the wall in the corner. He set his tool bag down and started to remove the boiler covers. Taking sneaky looks at my legs when he could. I offered him some coffee which he accepted and let me give him a good view of the back of my legs and my stocking seams as I put the filter machine on. I could feel my girly cock now swollen to the full extent my cage would allow and my arousal building.
He didn’t talk much but at one point he asked my relationship to Matt and I just said I was a friend. I don’t think he’d clocked that I was anything other than a real girl and hopefully he was thinking that Matt was a lucky man. He said he’d finished with the boiler and needed to check the radiators for air. I was expecting this, but fiend a little surprise before showing him into each of the downstairs rooms. I then led him upstairs, deliberately walking in front, knowing he’d get a good view of my stockings but not quite see my naked bottom and the cage. I made sure to keep my legs close together and give a good hip wiggle as I climbed the stairs. When we got to the top of the stairs I could tell by the bulge in his trousers that he’d had a good look at my legs and liked what he’d seen.
I showed him around the upstairs rooms, leaving the master bedroom until last. I apologised for my makeup being scattered about the bathroom. As I led him into the master bedroom I could see him clocking the lingerie. I could feel my cheeks were flushed from my arousal although I suspect he thought it was due to him seeing my discarded lingerie on full display. Of course, I’d placed the cum stained dress at the end of the radiator nearest to the bleed valve so he couldn’t help notice. He was clearly unsure if I was flirting or not, but while looking directly at the stockings on the radiator he said how much he loved seeing ladies in stockings. I told him that Matt did too and that I always wore stockings when I was with him. The poor man was definitely turned on, as was I. I could now feel a steady stream of pre cum leaking from my cage down my thigh and into my stocking tops.
Feeling really naughty I picked my skimpy satin nightie off the bed, holding it on display by the straps, and with a coy smile told him I’d be happy to pull him off into it before Matt got home, as long as he was quick. He didn’t need any further encouragement or discussion. By the time I had crossed the bedroom, his trousers and pants were round his ankles and his cock was standing to attention. I told him to put his hands behind his back and that he mustn’t touch me. I knelt down in front of him and wrapped the nightie around his cock making sure it was covered by several layers that would slip easily over each other as I was it to massage his stiff cock. It was less than 30 seconds before he had filled the nightie with cum while groaning loudly on each ejaculation. I carefully pulled every drop from him and cleaned him off with the few dry pieces of the fabric that remained.
I needed release but wanted to stay, at least somewhat, faithful to George, so closed down further conversations and told him to him finish up quickly before Matt got home. A short while later he was ready to leave. He handed me the invoice for Matt to pay and cheekily pointed out his mobile number telling me that if there was anything I needed, I should give him a call. I gave him a cheeky smile and closed the door. I quickly went upstairs, released myself from the cage, and with the lightest of touches of my hand up under my dress I found myself streaming cum with lots of micro ejaculations onto the bathroom floor. One long amazing orgasm.
A few seconds later George called and I was still breathless when answering my mobile phone. He said he was calling from the office and had been struggling to concentrate this morning as he was still turned on from our session last night. I explained that it had definitely left me feeling the same way and I recounted the detail of my late night garage stocking tops flashing and this mornings wanking of the boiler man. He said that he was so pleased that I was getting my confidence at being Rebecca and found it thrilling that I was so open with him about my exploits. He said he wished he’d been my boiler man this morning.
We giggled at that. He said we should talk more when we were together as he now realised that he’d spent 25 years leading a boring and perfunctory sex life with his ex wife and wanted to explore more, much more. He said he loved me very much and hoped we could expand our horizons together. We both professed our love for each other and then when asking me what my plans were for the coming days I reminded him that I had no work at the moment, so other than searching for contracts, not much. He suggested I pack up some things and come and stay with him while I looked for work. I hesitated, a little too long, and he quickly reminded me that I had the use of the spare room and en suite so I could keep my Cinderella moment secrets from him. I reassured him that my hesitation was not because I didn’t desperately want to be with him, I just needed to do some washing, packing and tidy up here first. I agreed to come over the following afternoon, Sunday, and stay for a while.
I arrived at George’s late afternoon with several suitcases. As always when I was with George, I tried to look both passable and sexy. He immediately kissed me full on the lips as we were standing on the drive, his hands caressing my bottom. As we separated, I said, “George, what will your neighbours think?”. He told me he didn’t care, and said it would just looked like he had a beautiful lady moving in with him. We laughed and he carried my bags into the house.
He opened some champagne and we took our glasses into the front room, sitting snuggled together on the sofa. He seemed a little nervous and said he wanted us to be together more than anything however we should talk openly about what we wanted from our sex lives. He said he didn’t want to constrain me and that on reading some of the erotic books I’d left around his house he would like to expand his sexual experiences too. “No more boring George!”, he stated firmly. I started by saying I was so happy being with him and that the last few months had truly been the best of my life. I certainly didn’t feel he was constraining me and that I had not experienced any ‘boring George’. I also said that it would be wonderful to explore our sexual appetites together.
Over the next half hour or so we discussed our desires and fantasises, at some length. There was some giggling and kissing too. We encouraged each other to really open up on where our boundaries would be. By and large, we found the same things were turning us on and soon realised that we would both like nothing more than exploring our fantasises together. We toasted to the Sexual Adventure List we’d just created! Both now incredible turned on by our conversation, George removed my dress and we made love on the sofa. He started with me on my back, waiting until he felt my release between our flat bellies, before having me kneel on the sofa, legs apart, head towards the back. He then fucked me slowly and deeply, while intermittently slapping my bottom cheeks. I was in heaven, once again wearing just a skimpy chemise, stockings and heels while being fucked by this beautiful man. He cried out as he came inside me, leaving cum pouring out of my anus as he withdrew. We fell back on the sofa lying together and kissing while we got out breath back.
I cleaned up, changed into some clean panties and a short satin nightie. We drank a lot more champagne while chatting and kissing on the sofa. When we finally retired to his bedroom, I slipped down the bed between his legs and used my hands and lips to get him nice and hard once more. Looking lustfully into his eyes I proceeded to take him in and out of my throat until he came once more. I cuddled up in his spoon, his arms around me, a very happy girl.
He got up well before me. I used the facilities in his spare room to make myself presentable again and came down to sit with him at the kitchen table, wearing a long silk dressing gown and fluffy sliders. He had his laptop out with a credit card next to it. He started to show me a website for an exclusive, very up market, sex club. It promised 100% discretion and a drug and disease free clientele while catering for every sexual fantasy I’d ever heard of, and many I hadn’t. The pictures showed very elegantly dressed ladies and gents enjoying themselves in a luxurious bar area, along with pictures of various playrooms containing all manner of equipment.
I just said, “Wow”. I was thrilled that he was really taking the lead and clearly wanted to embrace the fantasies we’d discussed. “I was so hopping you’d like it, as I’ve already completed the initial registration process for both of us. We have a private sexual health medical booked on Wednesday. This is needed for final membership approval.” he said excitedly. He explained that the club required a mandatory 6 monthly sexual health check at their appointed clinic as well as swabbing and a finger prick blood test on entry. “in this way our clientele are free to explore their wildest fantasies without the worries of avoidable health related consequences.” he said reading from their website.
We spent the next half hour exploring the website together, reading the literature on the sexual activities they catered for and looking at the images of the associated play rooms. Needless to say we were both getting extremely aroused. We made eye contact and yearning for him to be inside me I removed my dressing gown and bent myself over the kitchen table legs apart while he started to fuck me. My girly cock being pressed between my belly, my nightie and the table top was once more being firmly rubbed with each of his thrusts. It wasn’t long before we both came, me slightly before him. As I went upstairs to shower, again, and get dressed, he made us both breakfast.
Wednesday arrived quickly and George had said they would be expecting me as Rebecca. I was a little worried what the medical may involve as my bottom had taken quite a pounding from George over the last few days. We did take it easy the previous evening as I said I didn’t want to turn up with bright red bottom cheeks. The medical was more thorough than I expected, lots of intimate swabbing, taking of blood and general measures of fitness and heart health. I guess they also didn’t want their clientele pegging out from heart attacks caused by too much excitement. They also took lots of personal details, my job, financial status, social media profiles etc. Soon everything was completed.
The lady doctor and clinician looking after me obviously knew to expect a biological male from Georges registration so there was no embarrassment. Before I left, the doctor asked if I’d considered taking any further steps to transition. I said I hadn’t, and she said if I was ever interested in finding out more, I should make an appointment to see her. She said there were far too many examples of both malpractice and unrealistic expectations being set and she felt it extremely important that all the benefits and downsides of the various options were thoroughly understood before anyone considered transition procedures. I thanked her and said I would definitely get in touch if ever I considered going further.
That was it, we just needed to wait to see if we’d passed the medical and would be approved for membership.
As the days passed George would spend some time at the office although at the most it would be 5 or 6 hours and day and 3 or 4 days a week. He usually left early for work, before I’d got up, and was typically back mid afternoon. I was now Rebecca 24/7 and often spent the mornings just wearing my nightie and silk dressing gown, sitting cross legged on the sofa with my laptop on my lap, searching for work. Floss the dog would be curled up next to me, obviously grateful for company while George was away. I’d always make an effort dressing for George when he was due home. Sometimes a pretty girl next door look, sometimes a posh office girl look and sometimes, when I really needed him inside me quickly I’d just be wearing sexy lingerie and high heels. The latter always did the trick and he’d often take me quickly before we moved on to much longer and passionate love making.
On one of my more wanton occasions, I greeted him wearing a little maids outfit, with seamed stockings and high heels, that I’d bought on-line. I wore my chastity cage, no panties and had pre lubed my anus in anticipation. As soon as he’d closed the front door he had me there and then in the hallway. I was stood facing the wall with my legs apart. His trousers were around his feet as he thrust deeply into me, quickly filling me with his cum before we headed upstairs. Here he had me face the bed frame, and bend over while he cuffed my wrists to the bed posts. He then fitted an adjustable spreader bar to my ankles spreading my legs as wide as he could without me falling over in my heels. Now having difficulty standing, he proceeded to soundly whip my bottom cheeks with a ridding crop. It was not long before I was having continuous micro orgasms in my cage, my fluids now mixing with Georges as it leaked from my anus and saturated my stocking tops. After he was satisfied my cheeks were nicely reddened we moved to the bed where he removed my cage and he made passionate love to me. By the end I was thoroughly exhausted, I’d lost count of my orgasms, my throat and bottom had been filled with his cum and I felt the happiest girl in the world. Leaving no time to prepare a meal we ordered a take out and cuddled up on the sofa in front of the television.
More to follow ...
