senior (old) crossdressers?

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    Hello, I am sixty five and have returned to dressing for a couple of years now. It’s great to have the new tech to create lifelike breasts, gaffs, and the remote machines. I really enjoy viewing mature sissy’s and all your nice equipment. Dressed with my fellow girls during my early teens and developed a taste for the sex. Enjoy your times! Jacie

    Jennifer LoveJennifer Love

    Hi Daniele, thanks for your post I’ll have to see if there are any other pix on your profile. I like more mature experienced girlies in sexy lingerie .

    Jennifer LoveJennifer Love

    Your post about getting into your sitter’s panties at 11 was so hot. I can remember the first time in panties and how erotic itr was for a young boy. My most memorable experience is when I found my young aunt’s party dress and tried it on. Almost instant gratification. I did that as often as I could. I wondered what she thought when she found it with All those cum stains. Maybe she suspected, said nothing, but smiled at me. THAT gave me a other erection, rather embarrassing with others around. I tried to hide it, unsuccessfully.


    I’m 60, rather new to crossdressing. Only have sex with two females I know while dressed up. Never entertained thoughts of doing it with another man. Strictly straight, but love the feel of being in women’s clothes.


    i just had my 70th birthday, been a sissy dresser since i was in my 30s, started sucking cock way back in jr high
    love to trade photos

    Jennifer LoveJennifer Love

    Southeast Virginia. I started when I found my aunt’s party dress. It fu me wonderfully, it was black taffeta and had layer of crinoline so the skirt. Flared out. My penis was instantly rock hard and I think I ejaculated in about 45 sec. I must have emptied a cup of semen. I sneaked back into her house ivery day for a few weeks. It was wonderful and I was hooked.

    Now 75 and loving it more but with wife #4 I have to be careful. y Yes the other 3 we’re because I was caught or found out, ok lus another 6-year relationship. That ended when her daughter (cute, petite, sexy) fought a picture of me in her panties, erect and weeping. Busted. They were both hot and mom was quite the enthusiastic fuck. Multi-orgasmic which was a big turn on.

    More later! Lots of stories to tell.

    Keen GuyKeen Guy

    I believe we get hotter as we age. That little knowing pastime or the way we pose- it all makes for intrigue and fun. I go along with sharing and respect. So vital in what might be a lonely world. So cheer up fellow seniors , we have a trick or two to share with the newbies, and oh , all that experience. Don’t mind if you lean over my back yard ( yes , in the garden,
    !!!!) to reminisce . Be good !!

    Jeffrey Stonejeffrey stone

    Wish I was your neighbor ! Jeffrey here.. a bit older but still a great tall skinny tight fuck ! Sext me anytime at 262.716.9913.. hope you’re in the USA!

Viewing 8 posts - 16 through 23 (of 23 total)
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