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I was just wondering the age most guys get into crossdressing. I am a 56 bi married man and have thought about it a few times. Like a lot of guys, I would get dressed up while wife was out or if you were gone away on business. It would be a private, lights dimmed adventure. Get all horny, jack off then watch tv. I had been very horny lately because wife is in menopause and has no interest in sex with me. I was going through the closet looking for some papers. There was a bag of clothes that she gathered to donate. I went through it seeing if she was donating any of her lingerie items. I found a small bra in a package. It struck me odd because she is bbw with 42DD tits and her daughter is H cup. This bra was rather small and padded. I figured she was out so I tried it on. It actually fit very well and to add to it I put on a T shirt and the little bumps actually made me feel kind of sexy. I wanted a bit more so I put a pair of balled up socks in each cup. I was turning myself of and to feel them was erotic. I had been talking to a man online and we had talked about meeting for some fun. We met for some car fun. I was in the back seat waiting for him. I had on the bra without the socks. He immediately noticed and fondled me through the shirt. We kissed passionately and I was on fire as he fondled me through the shirt. I figured this is what a woman must feel like. It was very very hot and erotic. Eventually he did flip up the bra and sucked my now hard nipples. I suddenly felt very feminine and did everything a woman would. I sucked him long and passionately before he laid me down and entered me. He came twice before we had finished. I put the bra back on as we necked some more. Now I want more. The bra felt so sexy I was actually thinking of wearing a woman's bikini or a pair of bikini panties and a B or C cup padded bra. I've always been a sub but now feel more womanly than ever. I would appreciate any advice or stories you have as to how it started for you. I will private email too if you want to continue a long term chat. I live in Nova Scotia Canada
'This is what a woman must feel like.'
That's what I think every time I meet a man. I am a closet CD in a marriage with a wife that's not that bothered anymore.
That phrase went round and round in my head the first time I took a cock into my mouth. I was working out how would a woman do this, how would she make him feel good. I stroked his thighs and buttocks as he thrust in and out. I made sure to look up and make eye contact.
I hadn't be sure about it before, but I accepted that when he came in my mouth, however I felt about it, I was going to swallow and make sure he saw me swallow. I was so pleased with myself when I did it.
From then on I set about practising female mannerism, walking in heels, developed a feminine tone in my voice. I wanted to be the complete woman for the next hookup.
Although I had use dildos I was determined to find out what it felt like to have a penis inside me, not just physically, but emotionally too. What was it like to carry a man's semen inside.
Now I know and it's Fabulous!
My wife was the one that got me started wearing women's clothes. I was 23 and she wanted me to dress up as a woman for a Halloween party and she went all out for this she even shaved my legs and under arms I had to practice with walking around with 4 inch high heels for a week before I put on a pair of cheeky panties and black fish net thigh high stockings she helped me put on a black bra and she put the fake tits in the cups then I put on the skin tight red dress that she bought for me and a blonde wig then she did my makeup and after she finished I looked in the mirror and I looked just like a girl I couldn't believe how I looked. I was walking around the house so she could see what I looked like she said dam your ass looks good in that dress. When we went to the party no one knew that I was a man guys were smiling and looking me up and down. I found myself getting turned on by this. Long story short she continued to dress me up and we would go out and have fun and one night I went out to the parking lot and sucked a guy off when I came back into the club my wife asked if I liked sucking cock and how was it. I told her that it was not that bad and I kinda enjoyed it. I have been a bi bottom ever since then.
So lucky
Can we email?
Yes, I would like that. gruberron@yahoo.ca