I had lost and now I had to pay the forfeit, the four of us never played for money nothing so boring for us. The one who lost his stake first had to carry out the order of the final winner. It was king who won this time,a devious man who played cards well, never yet had he lost first in two years but on the times he won his forfeit was always sexual in some way.
This time was no exception but still it was a surprise when he spelled out to me what I had to do. King told me I had to go to his sister with him and she would dress me and do my hair, I was to go to the jugglers arms at seven and I had to get a man to want me. I could not leave before 10pm and not alone,I had to have one or more men with me.(Sex Stories)
I was not looking forward to this forfeit at all but King and I went to his sisters house in the next street, King told her what he wanted her to do to me and how long she had to do it in which was about three hours if I was to be in the jugglers arms by seven. She took me to her bedroom king had already left the house, she had a nice room with all the frills women liked to have. Clothes were her passion and she had so many I guess she never got to wear them out, she started with her underwear draw picking out a matching bra and panti set in deepest red. She had me undress and I had to put them on,the bra she adjusted and inserted silicon implants, the panties were so small my cock either poked out the top or hung out the bottom. It was more comfortable with it sticking out the top so that's how I left it. She had spent the time searching for an outfit for me, on the bed was a mini skirt and in her hand a pencil skirt and matching jacket. She had me put on the skirt which hardly covered my butt,a white blouse and the bra could be seen quite clearly through it. I had to take it off and put the pencil skirt on but keeping the blouse on, she was happy with the look this time and from the mirror I saw a great figure and from the neck down I looked great. I was handed a pair of silk stockings black to match the skirt,they had a seam in them like in the 1950's. The one thing she didn't have was heals to fit but she knew a friend who would have, she made a call before I was taken into the kitchen for my hairdo.
She had spent the best part of two hours now and i had no idea how I looked with my hair done and makeup on but somehow I knew I looked great,I could feel it and see it in her eyes. She had only spoken to me when she wanted me to do something so the smile she gave me was a clue that the job she had done was good. I stood up and saw my reflection in the window, I did not recognise myself but I looked far better now than before I arrived. I followed her outside and along the road stopping at her friends who had been waiting for us, a pair of heals in her hand I was shown into the front room so I could try them on. The heals were not too high and the fit was about right for me,I stood up and walked about for a few minutes getting a feel for them, I hoped I looked as good as I felt all things considered. It was about time for me to be at the jugglers arms so I thanked the ladies saying I would leave the shoes with the outfit and they both nodded.(Porn Stories)
My nerves where getting the better of me but Kings sister said in a whisper that I looked hot, she must have been right as several pairs of eyes stared at me as we took a seat. I realized that I didn't know her name and she had never volantered it,it turned out to be Caroline. She ordered a wine for herself and coke for me up at the bar and before she could pay a man offered to pay for them,he even brought them over and sat down with us introducing himself as Frank pointing to his left he told us was his brother Roy who he motioned over to us. Frank was a good talker Roy being on the shy side,but he was a looker not a Robert Redgrave but he had something that Frank hadn't magnetism you could call it. Caroline was doing OK with Frank,he seemed to accept that Roy and I had made a connection.
The drinks flowed as we talked and flirted even I was holding my own confident and happy with them, I had started to take notice of the people in the room,all were men apart from two women sat in a group at the far end. It was then that it dawned on me they were men dressed up like I was but not quite as good, stranger still that I was pleased about it. Frank said he had never seen a guy look so good, I was mortified that he knew I was a man. Caroline explained that this was a gay pub and that everyone was gay here including her,I had no idea and was surprised as she carried it off so well. I asked Frank how he knew I was a guy, his answer was that Caroline would only go outdoors with a man never a woman. I was having a swell time not noticing that it was almost 10 O'Clock, I was making leaving noises when Roy asked if he could walk me home. Caroline whispered we could all go back to her place if I liked, I wanted that more than I realized Roy and I had hit it off together and I was happy to be in his company.
The talk as we walked was getting a little deeper than it had been in the pub nothing vulgar but it had sexual undertones to it, I was at ease with it and held my own with them though Roy held back somewhat. I thought he was a nice guy and if I was a woman, it hit me then how in the last few hours I had completely changed and was thinking and acting as a woman.Roy knew I was a man but wanted to be with me and I had already admited I would be sexualy attracted to him if I was a woman. Caroline opened the door and we all walked inside,it was a surprise to see King and a young man sat together in the room. King asked Caroline how things where and she said it had all worked out fine and that Roy was proof of the fact. Roy and king looked at each other and king said happy birthday Roy, the smile on his face said it was just that and thanked both king and Caroline but then he came to me saying a spacial thankyou with a kiss.
I have been to Caroline's many times since learning how to make the most of clothes and makeup, I have become quite adept at it much to Roy's delight. I found out that Frank had been steady with Caroline for a few years Roy had always been too scared to date,we have been going together and have been making future plans. I knew it had all been a setup but I wanted to know how King knew I was Gay,Caroline said it was the way I looked and how I distanced myself from female involvement and looking back now I could see she was right. I had a lot to thank king and her for and knew my life had changed for ever.
We had been going out for a few months and after a night out he asked if he could stay, we had kissed and fondled each other but nothing more, who was more nervous was hard to say but the time felt right for me. I had got used to being a woman,Roy always called me Sandy which I liked but then I liked everything about him no hint of cockyness but a strong character happy to be who he was. It was the hurdle I was going to have to get over and I knew it would be right with Roy so I said yes I would like that. There was no need to pan things out with small talk and coffee,we both knew that sex together was the agenda so I led the way to the bedroom. Standing at the bottom of the bed looking at each other I saw the desire in his eyes,I hoped mine was a reflection of his own as he held my hands lightly kissing my ear,I felt his tongue inside lightly running around my body felt as if it had been jolted with electricity my head tilted back and Roy took advantage kissing it just under the jaw sending shivers down my spine. It was so nice with him kissing and slowly unbuttoning my blouse, the bra was not being very cooperative so I gave him a hand as he worked on the zip on my skirt. They dropped to the floor together leaving me in just panties,he was just getting his feet out of his trousers and being as he had no pants on I could see his manhood,smaller than mine but it sent a buzz through me just the same. Neither of us had much idea but I made a move by feeling him,not wanking but exploring by touch alone my eyes watching him so I could see in them any pleasure he was feeling. His fondling made me weak at the knees and I had to kneel before I fell, it put my head just in front of his awakening cock and it was just asking to be eaten. My hand let go of him to be replaced by my lips just rubbing the tip and my tongue flicking on it moistening it making it glisten,it tasted sweet not the nasty taste I expected.Roy was unable to stay still as I moved further down his stiffness, every suck brought a fresh groan from him and the pleasure I was giving him pleased me.
I coaxed him onto the end of the bed and lightly pushed his body backwards, I had gone along his cock as far as I could which was not much I wanted to take more but I kept wanting to be sick.I knew I would have to work on that aspect but for now Roy seemed contented and getting pleasure, I asked him to work his bum up as I sucked him in and soon we had a good motion going I had a mouth full of salive and it was making it hard for me to breath so I swallowed it just as he was thrusting,I felt him go deeper down my throat and the sick feeling didn't come this time. I waited till he was about to thrust once more and swallowed again,I had nearly all of him inside so thought I would try for the last bit but I felt him pumping away his spurn going straight down my throat. I kept him in till he started going limp before withdrawing him tasting the last drops of his cum,I wished I had had more to taste but there would be other times I was sure. He lay there spent and with a satisfied smile on his lovely face,laying on him I worked upwards my head resting on his chest.I felt like the luckiest woman in the world just then and my mind was at peace with who and what I was all thanks to King who planned it all.