We both felt like we were coming off a high for the few days immediately following our first adult club night, such was the extreme emotions and excitement we’d experienced. The evening had been fantastic and we agreed that there would be many more. We were now keeping in touch with Carol and Trevor as well as a few other couples we’d met, through the club’s web chat. We decided to try to go once a month and had already started discussing what we’d like to try next time, booking ourselves in for another evening which would be in just over 5 weeks time.
If anything, George’s libido had increased since our club experience. This meant my focus on setting up my web design and development business was being regularly redirected to sex whenever George was home. I of course I loved the attention and liked to surprise him by occasionally wearing my cage and plug under a smart office girl dress. I knew that over breakfast his roaming hands would soon discover my secret and that this would lead to a prolonged session of morning sex before he left for work. I loved sitting at my home office desk, feeling his cum seeping from me into my panties and the often a cum soaked silk slip sticking to me under my dress. To be fair, neither helped my concentration but the feeling was so good.
As I came down to a Friday morning breakfast, after the usual kisses and George giving my bottom a playful slap through my thin nightie, he raised the topic of our mutual desire to go dogging. He said that after seeing me used by Trevor at the club, the thought us being out with strangers wouldn’t leave his mind. There was a particular scenario we had discussed and of course we would play safe. I discovered George had already been asking for recommended locations on the club web chat and had found what seemed to be a safe and transgender friendly spot about 40 minutes away. Friday nights were supposed to be popular so impulsively we decided to go that evening.
In keeping with the scenario we had in mind, I tried to dress like a slutty cross dressing prostitute. I wore a small metal chastity cage and metal butt butt plug. Then I put on my expensive breast forms along with a black lace bra and black lace suspender belt attached to seamed, small mesh, fishnet stockings. Over the top, I wore a completely see through black micro mini dress that finished just above my stocking tops and, of course, I wore my highest black ankle strap heels. I put my hair up, attached long false eyelashes and applied heavy make-up with bright red lipstick and matching nail varnish. Looking at my appearance in the mirror, I could really picture myself as a hooker on a street corner. This, and thinking about what was in store later this evening, had my girly cock swelling to the full extent the small cage would allow.
George, going along with the theme, dressed how we would imagine my pimp to be. He had on a skin-tight plain black, short sleeved gym top and a pair of baggy grey sweat pant style trousers with white training shoes. The top really accentuated the muscular torso he’d been working so hard on at the gym. He’d slicked his hair back, and from the look of it, applied a little black dye. On seeing me, he gasped and just said, “Wow!”, before pulling me into him and letting his hands roam over my bottom cheeks. I could feel a bulge forming in his sweat pants and as it was now about 9:30pm suggested we leave before we both got too excited. George drove my old Audi A4 rather than taking his expensive Mercedes.
We pulled into the secluded car park around 10:20pm and we could see a few cars parked up by a wooded area with their interior lights on. There were some men, with their cocks in hand, looking through a car’s open windows and occasionally reaching inside. We stopped nearby at the edge of the car park, opposite a picnic table. We looked at each other to check we were still up for this, kissed, squeezed hands and stepped out into the evening air. George helped me walk the short distance across the grass to the picnic table before sitting me on the edge and laying me back. With my legs apart and my feet up on the table he gently removed my plug before applying plenty of lube. He drop the front of his sweat pants and started pushing his now fully erect cock into my bum hole. I was holding my ankles with my hands as he started slowly easing his cock in and out getting deeper with each thrust.
We soon had a few men gathering around us and George’s cock had started firmly pushing against my prostrate on each stroke. The tingles from my prostrate and excitement of being fucked in public while dressed as a tart soon became too much and I was having lots of small orgasms into my cage. George must have been turned on too as I could feel him pulse a couple of large jets inside me before pulling out and shooting the rest over my dress and belly. The men around us now had hard cocks in their hands and George invited any who wanted to fuck me to put on one of the condoms he supplied. He also said any who wanted, could just wank over me.
Soon I felt a cock push into my bum and start fucking me and could also see few men lined up behind waiting their turn. Clearly a few had also decided to wank over me as I started to feel cum splashing onto my body, going straight through the sheer dress I was wearing. When one finished in my bum George had them empty their full condom onto me while another took their place. I think many of the men fucked me a more than once. A couple of the lads were big, bigger than George, and I could feel my bum being stretched wider than usual as they pushed inside me. The almost continual fucking and the feeling of being soaked in strangers cum gave me more orgasms than I could count and my chastity cage ensured they became prolonged waves of pleasure rather than one big release.
Soon the lads were spent and moved away, a few asking George when we’d be back. As George helped me off the picnic table and sat me on the bench, I was still immensely aroused from the experience. He obviously was too. His cock was almost fully erect in his sweat pants. Making eye contact with me we both gave a knowing smile and he pulled the waistband of his pants down to release his cock. I eagerly took it between my lipstick covered lips, working my tongue around the head before sliding my mouth up and down his shaft and holding him in my throat for a few seconds each time. I was soon rewarded by another huge load from George which I struggled to swallow, leaving more cum to fall onto my dress. Thankfully we had put some disposable seat covers in my car as I was quite literally dripping with cum as we left the car park.
On the drive home we were both still excited by the experience and I had to keep reminding George to take his hand off my stocking tops and put it back on the steering wheel. Once home I of course had a very thorough shower, sanitised and then showered again. It was gone 2am when I snuggled into bed next to George, wearing just a little silk nightie. As he spooned me I could feel he was still firm and his cock was pushing the thin fabric of my nightie into my bum crease. I rolled him on to his back and carefully straddled him with my legs. Using a little lube from the bedside table, I eased his cock into me. I bent forward to give him a long deep kiss before riding him cow girl style until we both came and finally collapsed into a deep sleep.
Over a late breakfast the following morning I told George that I had been giving a lot of thought to how being Rebecca 24/7, and of course being his girlfriend, felt so wonderful. I said I would like to take things a little further and become a bit more ‘girly’. He was clearly confused, so I replayed some of my conversation with Carol about her hormone therapy, Adams apple reduction and laser hair removal. Like Carol, I said that I did not want to undertake full gender reassignment and loved having my girly cock. George was very understanding and repeatedly pointed out he loved me for being me and that I didn’t need to do anything if it was just to please him. After I assured him that it would be to please me, he said he would of course support me with whatever I decided to do. After some kissing and cuddling while I sat in his lap, we both agreed I should at least make an appointment with the doctor Carol had used for her transition procedures, the same doctor I had met for the club’s sexual health check.
After breakfast on the Monday morning I phoned the doctor and surprisingly managed to get an appointment that Wednesday. The secretary explained that I was incredibly lucky as a cancellation had literally just come through and the consultants waiting list was usually 4 to 6 weeks. I gratefully took the appointment. The doctor, technically a consultant, was called Gloria. She seemed to be in her mid 50’s, a similar age to George, and was an attractive lady. After a very long consultation, where I quickly realised that this was not actually about what I wanted, it was about her being comfortable that it was right for my circumstances, we agreed a course of action. She would prescribe hormone treatment and arrange for the Adams apple reduction and nasal reshaping surgery to be undertaken at the clinic. I would arrange for laser hair removal separately and she gave me a list of recommended clinicians for this.
It wasn’t until right at the end of the consultation, as we were discussing the expected time line of physical and emotional changes that the hormones would cause that I discovered she was a biological male. She let slip into the conversation that doctors now had a much better understanding of hormone treatment and that it had been a little bit hit and miss when she had started on them. Of course we chatted more about her experiences and I felt huge reassurance that she was the best person to look after my transition over the next few years. As I exited through her packed waiting room, I felt a little guilty because I had clearly overrun my allocated time.
On the way home I realised that making the decision on treatment was like having a weight lifted off my shoulders. I was really looking forward to the changes that I hoped the procedures would bring. My nose and Adams apple surgery was scheduled for a couple of days after our next club night and that due to the expected recovery time, I agreed with George that we would need to leave at least 2 months before the club night after that. I started the facial hair removal sessions and hormone treatment straight away.
Our dogging experience had left us both incredibly horny. This and feeling elated after my trip to the consultant’s, made me decide to surprise George when he came home from work on Thursday night. I changed into one of my new office girl outfits. A just above the knee tight black skirt with a slit up the back, a sheer cream, high lace necked long sleeved blouse and a black jacket. I wore one of the sexy silk lingerie sets George had bought me along with fully fashioned seamed stockings and heels that would be far too high for an office. I went with a subtle make-up but bright red lipstick and nail polish which really popped. I finished the look by putting my hair up in a bun leaving long curls down to my shoulders on each side and finally a pair of librarian style glasses to really portrait the sexy secretary look.
I was still getting ready so missed George coming home, shouting “Hi, darling” down the stairs as he came in. He had gone straight to the kitchen to put some shopping away. I quickly finished off and headed down. When he looked up as I walked across the kitchen, I knew my plan had worked. He immediately stopped what he was doing, stood up and pulled me in towards him, his hands going around my bottom while he planted kisses on my neck and mouth. He then led me upstairs where he had me remove my jacket, bend over the bed head and brace myself so he could paddle my bottom. The feeling of a tight skirt over my swelling, reddening, bottom cheeks as they were being paddled felt so good, it wasn’t long before I was getting desperate for him to be inside me.
He stood me up and unzipped my skirt letting it fall to the floor so I could step out of it. I spread my legs while still bent over the bed end. He pulled my thong to one side and started pushing his hard cock against my pre-lubed hole, using his hands on my hips to pull my sore cheeks hard against him on each thrust. It wasn’t long before he started pumping jets of his cum against my prostrate which almost immediately cause me to fill my small silk panties. As he pulled out, I felt the usual pleasant stream of cum running down my upper thigh and onto my stockings.
He undid my blouse and we moved onto the bed where had me lying face up with a pillow under the small of my back. After some more kissing he pushed his rapidly re-hardening cock inside me again, fucking me hard while keeping my legs and ankles wedged up high over his shoulders. I could feel myself orgasm several times before he filled me once more. Putting my arms around him we lay together exhausted before he eventually rolled off me. I cleaned myself up before putting on little silk nightie joining him down stairs to cuddle on the sofa and see what was happening on the club’s web chat.
We had been in regular contact with Carol and Trevor over the chat and through this we decided that on our next visit, now in just over 2 weeks time, the four of us should get together. I exchanged mobile numbers with Carol and over then next few days we discussed various scenarios we thought George and Trevor may enjoy. Carol also shared more about her procedures and recovery which I found very reassuring.
My hair was now growing out nicely, although still a too short to put in a feminine style without a wig. George could see my frustrations and suggested I go to a local, but upmarket hair saloon for advice. He knew the head stylist there from some fundraising he’d helped with and said he would be happy to have a word with her if I wanted. I really did. It was the first time I’d visited a stylist as Rebecca and was amazed at the result. With a combination of careful trimming, styling and a variety of colour matched hair pieces I came away with shoulder length and very natural looking hair. I booked in again for the morning of our next club night, wanting to look my best for Carol and Trevor.
More to follow …
