My first cross dressing experience

Posted in: TvTs

My story goes back to just after I was married, age 21. Shortly after the honeymoon, my wife and I were making whoopee in our new bed. She was wearing the satin nightie I bought her, I was naked. As we rolled around I became really aroused by the soft satin on my body. I knew she felt great through the softness of the material, and after we had come to a complete standstill in our love making, we ended up like two spoons, with me behind her. The feel of the satin on my prick was starting to make me come hard again. I gently moved the nightie around my prick and my balls and between my legs, getting harder still. My wife was asleep; I could tell by the slow quiet breaths.
Some time later she had to go to her mother’s house to assist with dad, as he had a fall. I was all alone for a few days and had to make my own meals, even washing my smalls. As her dainty panties slips and bras were in the laundry basket, I washed them too. When it came to ironing them, I was getting aroused holding her satin underwear. I stripped off and put on her panties and slip although they were still wet. The feeling was fantastic. My erection was massive, I began to think it had never been bigger.
I finished the rest of the ironing and then stood naked as I ironed the underwear I had had on.
I went to our bedroom and started to look though her wardrobe and underwear drawers, to see what else I might wear. There was so much, it was hard to decide. Before we were married I used to buy her sexy stuff and she too used to get more, from an Anne Summers type shop. I chose some nice tan Cuban heel stockings, a lime green satin garter belt with matching lime green panties, bra, half slip and chemise. After dressing I began to rub myself all over, feeling the delight of soft satin around my privates. In the drwaer were some Tampax tampons. My heart started racing. I took one from its packet, deciding whether I should stick it up my arse. Using some self warming lubricant, I smeared the cardboard tube, laid down on the floor with my feet on the bed and gently slipped the tube into my anus. It felt wonderful. I removed the tube leaving the tampon in place with the little string hanging out. I looked throught he wardrobe and saw a dress that my wife rarely wore these days. It was a polyester shiny dress. I put it on, and found a pair of sandals that I could wear with the sling left down. I went downstairs and got myself a drink. I thought I would watch one of the porno movies we would watch before we made love, but just as I was settling down, I heard a noise at the back door. As I stood up, my wife walked in with her suitcase. “What on earth are you doing? Your wearing all my clothes.” She shouted. I crumpled onto the sofa, my head in my hands.
After a few moments, I felt her sit down next to me. She took my hands from my face, and said, “I understand. I have wondered about your satin fetish since you keep rubbing yourself with my nightie. Does dressing in my clothes make you feel good?” I said it made me feel great, that this was the first time I had dressed up. I said, “I won’t ever do it again, I am so ashamed; ashamed you found out like this”. “Shush”, she said, “I quite like the thought of you like this. Come to bed now and see if you can be a man still dressd like this”. She took my hands and we went upstairs. She asked me to take the dress of, leaving me standing there in her underwear. She dropped her dress to the floor, slipped off her shoes and pulled me towards the bed. We lay side by side as she whispered endearments to me. I still felt foolish, but she was warming me to the idea of staying dressed as I fucked her. I grew bigger as she handled my prick. “Come on, big boy!” I moved over the top of her as she opened her legs to allow my inside her warm moist cunt. She must have been thinking sexy thoughts too, because her cunt lips were swollen and tiny trickles of love juice were running towards the crack in her arse cheeks. I entered her and the feelings were immense, mind blowing. She was stroking me over the satin underwear, and suddenly she lifted her legs and positioned herself so that she could place a leg over each of my shoulders. When she had done theat she reached under us and fondled my balls; Wow! What a feeling. “What’s this?”, she said. I felt her tugging on the tampon string, I immediately grew harder as she toggled it about, moving the tampon indie me, touching somekind of nerve endings that sent shiver through me. “You cheeky boy. You’ve got a Tampax in, Haven’t you!” She kept pulling and releasing it as I continued to pump my merry organ inside her soft wet swollen cunt. I could fee she was near to a climax, and I wanted so much to shoot my cum load into her at the same time she came, but mangaed to hold off. I could feel her cum around my prick and running onto my balls and put my hand down there. There were gallons of the stuff; no wonder I was slipping in and out so easily.I leaned back and started to move slowly in and out, and with my thumb I massaged her clit. It didn’t seem long before she was shuddering again, and as she climaxed, I was looking at her cunt when I saw a jet of clearish soft gel shoot out of her clit all over my scrotum. I took some on my fingers and tasted it. It was nothing like I had tasted from there before; it was sweet as soft. I wanted to lap it up so I took my prick away and began to suck all the juices out of her. She climaxed again, though there was not so much cum this time, I did drink it all up though. When she stopped shuddering, we went to the spoons position with me behind and I fucked her till I came along with her climax. We fell asleep like this and woke to a bright sunny morning. I realised I was still dressed in women’s clothing and felt a little foolish. My wife was ever so charming. She told me she was more than happy for me to dress up for her, and perhaps we should shop for some clothes that might fir me better.
We did, and I shall regale you with the results next time.

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My first cross dressing experience, 9.4 out of 10 based on 5 ratings

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  1. sounders1961

    wow…outstanding…got me nice and hard….mmmm

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