Magic Dress - Michelle Pt. 04

I was working for a charity as Michael during the day, while in the evenings and weekends I wore dresses and was Michelle. I lived with Anne, the love of my life, and we frequently fucked, as I was not gay.

One day Anne said "You remember how I said I would tell you if I wanted something in the way of sex? Well there is something, but I don't know if you would be willing."

"Of course I will, Darling. Anything at all," I rashly promised.

"OK, then would you please do me up the bum?"

"How do you mean?" I said, somewhat startled and a bit unsure.

"Would you please fuck my arse, bugger me, shove it up the sh..."

"All right, all right! No need to get coarse."

Actually I had never been one for swearing as a man, and as Michelle I was positively ladylike. I accepted cock and cunt in their proper place (in language, as well as in use) though I preferred the term 'pussy'.

"What I mean is: why on earth would you want that?"

"Because I might like it. Many women do, and I've sort of fancied it. I tried it with a couple of guys, but they were too big and too keen so it hurt. I think with you it might be better. Of course you will have to wear protection to keep yourself clean. I've actually prepared myself, so I think I'm empty if you're willing to try."

This was something new. Not just the action, but the fact that it was being done in such a deliberate way. Up till now it had always seemed that we did what we wanted when we wanted. But I loved her, and if it was another way to give her pleasure, why not?

Her mouth had me hard enough quite quickly, then for the first time I had a condom put on me. I sagged a little, but she got some lube and rubbed it firm again, and applied plenty to her little bumhole, which looked very tight. She put her own finger in and rubbed around, then showed me it was clean. She stood by the bed and bent over with both holes exposed.

I pressed my knob against her, but was afraid to push too hard until she encouraged me. I could also feel her tightening and untightening as she tried to help, then slowly all the knob was through. "Wait a minute," she said. "Let me get used to this." Then after a while, "Try some more."

I pressed and started to slide my shaft in. She gasped, but said "Keep going!" which I did till I was all the way in. I sensed I should wait a little, then started moving in and out. "Oh yes!" she said in a way which I thought meant approval, then "More jelly, then carry on." I complied and soon I was 'fucking her arse' as requested. After a while, she stopped me for more lube, then we carried on. To be honest, physically it was not a lot different from fucking her cunt from behind, but of course the emotions were not the same.

I came, which was physically nice, but did I enjoy it? I couldn't really say yes or no.

She told me to please stay in for a moment, then after short while pushed me away. Her little hole was open and I had a bag of sperm on the end of my drooping cock. I took off the rubber and got a flannel to clean myself, and another for her.

"Well that was interesting," were her first words. "Thank you so much for being willing to do it. I do love you!" and she kissed me. "You didn't hurt me at all, and it was really nice when we got going. It was stimulating me in different places and in different ways. I think I would really enjoy this for a change sometimes. I've always wondered -- now I know."

That was the beginning of what I might describe as our sex life. In her pussy or mouth, that was our love life, and the best, but people can enjoy sex just for itself, and I was more than happy to be the provider of any pleasure for her. I learned to please her with my fingers and mouth, and was in awe and wonder at the female orgasm. She was so more complicated than my simple little cock. But I didn't mind. I had never wanted to be a girl in that way, only in the everyday life and the free appreciation of clothes and other things. I also learned to fuck her up the bum in way she really enjoyed. It was OK as sex, and I was glad to do it, but it was not part of my love life.

One day I licked her to orgasm, and sensed I should go on with my fingers as she was really wet. She came again and again, then said "Stop!" and started crying. I wanted to know what was wrong, but every time she started to explain she could hardly begin a sentence without sobbing uncontrollably.

"It's so unfair!" she eventually gasped. "You give me so much pleasure and I can't do the same. You're better than any man or woman and you do it with so much love, I'm not sure I can take it. I feel so guilty but I want it so much!" She held onto me and buried her face in my chest.

Suddenly I understood my mistake and hers. It wasn't just sex, it was love. It wasn't about being fair and equal: it was taking joy in the pleasure of your true love.

"It's totally fair," I eventually said. "Every time you come, that is a gift to me. So far as I am concerned it is all lovemaking. I know that you love feeling me come in your mouth. Accept that I feel at least the same when you come with my mouth. And if you like my cock in your mouth, think how much more I have to explore and enjoy with your dear pussy. I so much love feeling it with my fingers and mouth. To tell you the truth, I've been wishing you would let me do it more often, but didn't like to ask. I was thinking I was greedy to want more." I paused.

"I'm begging you: please let me love me as much as you can manage and I we will both live happily ever after!"

We hugged and kissed and argued who was the more wonderful, and agreed to share the joy as often as possible.

For my next birthday of course we went to my parents, but I went as Michelle. I was surprised how many people were there. Both my uncles and aunties, both sets of next door neighbours and some of the staff from work. I guess they wouldn't be there if they had a problem. I was wearing the magic dress, of course. There was cake with 22 candles, drinks, and a rather limited buffet as people had been asked to bring food contributions and had mainly brought sausage rolls. It was suggested we took some home with us. I was kissed a lot and had to dance with all the men, starting with Dad. What was really good was than nobody said how brave or remarkable I was. It was just Happy Birthday, Michelle.

When we came back to the flat, Anne excused herself and came back in a different outfit with a small package. "I don't know if you're going to like it, but at least it's the thought that counts."

Inside was a rubber cock, quite similar to mine. I didn't understand. She lifted her dress to reveal a sort of harness into which she fitted it. "I thought you should see what it feels like to have a cock up your bum!"

I went to the toilet and reported I was not messy. Anne had some lubricating jelly and two butt plugs: tapered rubber objects with a bar so they could not go in all the way; one quite small and one about the same as the dildo but very tapered. She said it should be easier than it was with her now we had the equipment.

The first one went in quite easily, and I walked around getting used to it. An unusual sensation, but not unpleasant. I got on my hands and knees on the bed. She moved the plug in and out for a while, then got the next one. The taper helped, but I could feel myself being stretched, so we took it slowly. Gradually I relaxed and it all went in. Because it had a narrow neck, it hurt a bit when she pulled it back, but after a while of going back and forth I had stretched enough to take it with no trouble. I admitted it was a bit pleasant.

Then came the cock. It didn't have a taper like the plug but a proper knob which was more difficult to get in, but strangely satisfying when I managed it. Then slowly the whole cock.

Anne was gleeful. "How do you like that, Michelle? Being filled up?" I said so far so good, and she started sliding in and out, pausing at one point to apply more jelly. My own cock was half hard, and I began to appreciate the sensation. "Michelle's getting fucked! The naughty girl! Fuck, fuck, fuck, with a nice cock!" said Anne, giggling. I think more than anything I felt a sense of achievement, and was happy with that.

Then there was another sensation, which was of course my prostate being stimulated. Strange but pleasant. My cock was now stiff and started to drip. Anne noticed and laughed "I think I've found Michelle's G-spot!"

We went on till Anne was tired, and had to stop. We wiped ourselves and she sucked me off.

Of course we practised until she could make me come, but I quite liked the sensation for itself without coming. We eventually settled on a routine where I licked and fingered her to orgasm, then fucked her bum till I came, and then she fucked mine for a while. We did this about once a week, as I didn't want more and that was enough to satisfy her. She got some sense of being fair, as she did like receiving anal sex, but it was best if she was really excited beforehand.

I usually fucked her pussy at least twice a week and was sucked off at least once. However, it gave me the greatest of delight to give her at least one orgasm with my mouth and fingers, which was pretty much every day. This was all lovemaking. Naturally we kissed and cuddled a lot, but we were very happy just being together.