Three or four weeks had passed since my meeting with George and I was now longing for another meet. I’d not fully dressed since that evening either so I was getting a little desperate to once again transform into Rebecca. George and I had kept in touch, initially by text and now we were emailing several times a week. We discussed our likes dislikes, hobbies and of course meeting again.
George kept suggesting I come over for dinner however up until now had struggled to commit. I could see I had a time-in-lieu day booked off work for the coming Friday, so suggested to George we meet up that evening, which would give me plenty of time to get ready. He was delighted. He said I should come over about 8pm and park on his drive. He’d cook us a light supper and we could have a glass of wine and see where things went. Typical of George he went on to stress I mustn’t ever feel uncomfortable and could leave at anytime.
It was Tuesday now but, excitedly and looking forward, I started to plan what I was going to wear. I selected a sleeveless grey pinafore dress with a fitted top and pleated skirt which finished mid thigh. It had a large fine check stitching detail with black velvet trim around the collar, waist and hemline. There was a matching jacket too. Underneath I’d decided to wear a scarlet chemise with spaghetti straps, low cut back and black lace trim on the bodice and hemline. I quickly realised that none of my bras looked good with the chemise so I would have to go without. I had a set of good quality breast forms, a B cup, that fitted nicely and would be largely hidden under the chemise. These came with some prosthetic glue, although it would be the first time I’ve worn them this way.
Friday quickly arrived so I took my time to get ready, a long soak in a scented bath and a close shave of my face, armpits, chest and legs. As I’ve mentioned before I was blessed with virtually no body hair and have always had a girly smooth bottom. I also gave my self a good douche down below, in anticipation that things may go further with George this time.
While drying in a large fluffy dressing gown I carefully painting my finger and toe nails in a deep red varnish that would match my lipstick. I then carefully attached the breast forms and held these in place until fully secured. Wow, they felt wonderful and gave a nice weight and pull on my chest that made me feel really feminine. Next I put on a pair of seamed 15 denier black stockings, being sure to keep the seams straight and the straps nicely positioned around my bottom cheeks. I pulled up a pair of tight black panties with lace trim and a narrow back that left my bottom cheeks on full display. A pair of 10cm heels with ankle straps were next, followed my the chemise.
Standing back to admire my work in the full length mirror I was amazed with how I looked. My heart started to race and I was getting an unwelcome bulge in my panties. Careful not to get too aroused just yet, I took my time to do my makeup. I’d spent a lot of time practicing and could now get a feminine, pretty, but not overdone, look most of the time. I finished off with deep red lipstick. Next, I put on my brown wig with blond highlights, clipping it on firmly and putting it up in a pony tail so my neck was exposed. Then came the dress, matching jacket and some jewellery including some dangling silver clip on ear rings.
Once again in front of the mirror, wow, this was my best look yet. I was struggling not to touch myself, the braless yet weighted chest feeling was new and extremely pleasant. As usual, I took a few pictures of Rebecca before her date night, some demure and some flashing those seamed stockings.
It was now 7:30pm so I grabbed my handbag, already containing my makeup repair kit, mobile phone, spare panties and new some new additions of lube and condoms. I headed out to my car, got in the drivers seat and then the nerves hit me. What was I doing? What if someone I knew saw me? What if I broke down? etc etc. After a few minutes of controlled breathing I got myself together, texted George that I was on my way and set off. 30 minutes later I pulled into his drive, checked my makeup in the vanity mirror and carefully got out, smoothing my dress down and grabbing my handbag before heading to his front door.
The door opened just as I approached, George was there with his big friendly smile welcoming me in. After quick peck on the cheek and telling me I looked absolutely gorgeous, he led me back into the kitchen diner with his hand on my waist, slipping down to my bottom as we went along. Floss the dog came and greeted me like a long lost friend before retiring to another room. I removed my jacket and like a gentleman George carefully took it from me and into the front room where he lay it over the sofa.
The table was laid for two and he beckoned me to be seated before filling a champagne glass for each of us. We chatted over a light dinner, carbonara and salad, and I complimented on his obvious efforts to get fitter since our last meeting. He said he’d hoped we’d meet again and wanted to look his best for me. I helped him clear the plates away and stack the dishwasher. Standing in his kitchen he topped up our champagne glasses and then putting his down on the counter he moved in to kiss my neck, hands on my hips pulling me closer. I put my glass down too and put my arms around him, our kisses moved to our mouths and became more and more passionate. I was in heaven, very aroused, he made me fell so feminine and sexy.
He pulled his lips away and asked if I was OK. “Of course, this is delightful” I replied. I was loving his attention and said that he should continue. He turned me round and slowly unzipped my dress while kissing my neck and back which was exposed by my pony tail, backless chemise and braless outfit. He held my dress while I stepped out of it and folded it over a chair. I was once again standing there in his kitchen wearing just my stockings, heels, panties and a chemise. I gave him a twirl, while he commented on how sexy he found my legs in the seamed stockings. He pulled me in for more kissing and started using his hands to caress my bottom, lower back and hips.
Each time our mouths were not locked together he would tell me how lovely I was. I was getting a firm bulge in my panties and was now very turned on. I could tell he was too.. Whispering in his ear I suggested he remove his clothes and we should take things further.
He was soon standing naked before me and I felt like the luckiest girl in the world. He had a strong frame that was now showing obvious signs of gym work, and of course that lovely cut cock, thick and around 8 inches with a bulbous head. I moved closer, knelt down in front of him and wrapped my lipstick covered lips around the very tip of his cock. Using lots of saliva I slowly began to take more and more of him into my mouth, moving back and forth over his shaft. It felt so good, so much better than my dildo. I tried to keep eye contact and looked up adoringly at him while working his cock. He was now very hard and leaking pre-cum into my mouth.
Slowly he pulled away from me and guided me up to my feet before kissing me deeply and caressing my body with his hands. Whispering in my ear he asked if I’d like him inside me. I whispered back that I really wanted that more than anything. He led me to the table, turned me around and gently bent me over so my bottom was now up in the air. I parted my legs and could feel my now very aroused girly cock pressed between me, my thin panties, chemise and the table top. I could hear him squeeze some lube from a tube as he pulled the back of my panties to one side. I felt the cold lube flow on to my sphincter which sent waves of excitement through me. He started to open a condom and not knowing what came over me I said “No you don’t need that”. I felt I’d got to know him, trusted him and wanted to feel everything. He asked if I was sure, I said “Yes, I’m yours, please take me”.
I felt his bulbous head pushing on my sphincter, and then a little firmer. My muscles relaxed and I felt his head enter me. He took things very slowly, moving further inside me just a little at a time, pulling back after each new penetration. After a little while he was deep inside me, the feeling was intense, with each push I could feel the head of his cock touching my prostrate sending waves of pleasure through my body. That coupled with my own cock now being firmly rubbed between the table and my chemise with each of his thrusts, was rapidly sending me over the edge.
He picked up the pace a little, then suddenly slowed, continuing with paced deliberate and more forceful thrusts. Then I felt it, he was ejaculating inside me. I could fell my cavity being filled with jets of his cum. The feeling was too much and I felt my own orgasm hit, filling my own panties. We were both breathless, he lent forward once again kissing my back and neck telling me how wonderful I was. I told him it was he who was wonderful. I stood up and we embraced once again before he led me upstairs to the bedroom.
Soon our caressing and kissing had him aroused once more and he made love to me again on the bed, I was face down with some pillows under my hips. I still had my high heels on and felt a real slut lying there with cum already leaking from my arse hole as he entered me a second time. My mind was a blur, my senses were electrified as I felt him fill me once again. I just wanted to make him happy. After he gently pulled out of me for the final time we lay together on the bed exhausted, his arm around me. It was now late so he suggested I stay the night. Hesitant and not wanting him to see me as a man I said it would be better if I went as I’d have to get up early. He said he’d set the alarm for 6am and I could leave before my Cinderella moment wore off. Really not wanting our night to end, I accepted.
He found me a tooth brush and a clean towel and said I could use the en suite to clean up. I retrieved my dress, jacket and handbag from downstairs and went into the en suite. The makers of the lipstick that had promised smudge free kissing had obviously not tested it with George. I cleaned my teeth, tidied my lipstick up and removed stockings and heels. I laid my neatly folded clothes on a little stool in the en suite. I then realised I had to do something with my cum soaked panties so I had a quick clean up down there and swapped them with the clean pair I’d brought in my handbag. Finally I tidied my hair up, although admittedly it wasn’t too bad. It was still firmly in place and as long as I was careful in bed it should survive the night.
Now wearing just my chemise and panties, with smooth bare legs and body I slipped into bed next to George. I could feel the breast forms pleasantly tugging at my skin, still firmly attached. George pulled me into a spoon, arms lovingly around me and we both soon dozed off.
The alarm went off at 6am, although I had been awake for awhile enjoying the feeling of lying in Georges arms. He reached over and turned the alarm off before gently kissing me. I rolled to face him and returned his kisses, lowering my hand to his now firming cock. I felt I missed out a little last night so slipped down the sheets and once again took his bulbous head into my mouth, moving up and down rhythmically. It was not long before he was fully hard.
Gradually I managed to slip his firm cock all the way into my throat and hold it there for a few seconds. I did this a couple of times before I felt him start to pull away from me and say “Careful, I’m going to cum”. I pulled him back and told him I really wanted him to fill my mouth with his cum. I took him back inside my mouth, bobbing up and down while being sure to glance up adoringly from time to time. Once more I took him into my throat. As I was easing him back out I felt him unload in my mouth, jets and jets of pulsing warm cum, I had to swallow quickly as there was so much. He tasted fantastic so I carried on sucking and licking his cock until ever drop was gone as he gently moaned in ecstasy. I felt such a girly slut and loved it. I was very aroused myself, with the taste of cum still in my mouth, a wonderful feeling.
He pulled me back up the bed and said how wonderful I was again and again, followed by more kissing and caressing. Slowly pulling away, I gave my apologies and said that I must really leave now. He got up and said he’d make me a coffee while I got dressed. He left me to use the en suite and pulling on a dressing gown went downstairs. I tidied myself up, reapplied a little makeup, just enough to look the part and slipped on my dress, jacket and heels. I balled the stockings into my handbag and then went downstairs.
After a quick coffee, some more kissing I left George and made my way home. I was on cloud nine. When I got in, I just sat at my kitchen table in absolute heaven, replaying everything that had happened in my mind. I felt so amazing and aroused. I went upstairs removed my jacket and dress and used my dildo in my still slippery bottom to bring myself to orgasm and once again fill my already damp panties.
More to follow ...
