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Bi-Sexual Male / 55

I Miss Crossdressing When I Was Younger

...by younger I'm referring to my late 20s.

I had kids and an ex wife and I craved a new experience. Sparing the details, I was a decent looking 'girl'.

Between a redneck bar and prostituting, I got fucked A LOT!!! Swallowed plenty or cocks and cum as well as as ate pussy while getting ass fucked.

Very few bad experiences and only while hooking. Made damn good money, though.

Now in my 50s with grandkids and a wife, I still crave cock. Dildos only do so much.

Anyone else have similar desires and or experiences?

Anyone want details? Just gotta ask questions about something specific.

6
# 76476 - by Scott / January 30, 2025
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Comments

Anonymous

by Anonymous on Jan 30, 2025 at 5:25 AM

I sucked cock in my late teens and early 20’s. I’m married with kids and grandkids and I’m in my 60’s now. I’m back to sucking cock again. Seems like guys in their late 50s early 60s are really into cock. We have a small group of regulars we all get together with each other from time to time to fight the urge. Luckily, we seem to have more tops in group than bottoms.

(5)  (0)
Anonymous

by Anonymous on Jan 30, 2025 at 6:10 AM

My Grandma used to love playing dress up with me. Putting like girl outfits and undies on me. Ribbons in my hair and a little makeup, etc. After I hit puberty and my little pecker got bigger and hairy, it would pop out of my little girl undies when she dressed me. The more she touched it and tried to hide it, the bigger it got. Eventually she would stroke it to make my boner go away. After that I went from being her "little girl" to became her "little man".

(5)  (0)
Anonymous

by Anonymous on Jan 30, 2025 at 6:20 AM

Not to take away from number 2, I grew up in a household with six brothers. My mother always wanted a girl, and she saw me as the girl. As a baby she dressed me as a girl, as a toddler she dressed me as a girl, as a first grader she dressed me as a girl. I was taught early to only sit to pee, and to always, always be a girl. I will tell you that prepuberty I loved being a girl. But puberty hit me like a Mack truck.

I got boners all the time and couldn't tame them, as my mother called them. I continued to dress as a girl. I wore long hair, and makeup and shaved my legs. But my boners kept coming and my mother got angrier and angrier because I couldn't tame them. Then as it happens one night at a party, I was fifteen and it was a house party, I kissed a girl and got a real boner and she was surprised that I was a 'boy'. In my girl clothes I fucked her. And had my first sex. It was addictive, and this girl was embarrassed, but she 'put out' because I had already fucked her.

It was when I went to college that I quit being a girl. Now I got boners for girls, and some girls were so amazed that I knew so much about girl clothing.

(3)  (0)
Anonymous

by Anonymous on Jan 30, 2025 at 7:30 AM

How many loads do you estimate that you took in your asspussy and in your mouth? What was the youngest guy? And the oldest? How big was the biggest cock you took?

(3)  (0)
Anonymous

by Anonymous on Jan 30, 2025 at 8:49 AM

#4...a rough estimation would be 200 loads in my ass from over 100 cocks.

I swallowed around 300 loads from 200 cocks.

Ages are just a guess, but I know I was gangbanged by 5 senior citizens who all had to be over 70.

Youngest was a mother who hired me to suck off her 16 year old son and for him to suck me off. Weird story there.

Biggest cock was a redneck... at least 10 inches long and had to be all of 2½" thick. A close 2nd was one of the Geriatrics...a black guy who was never able to get fully hard and was only a little smaller than the redneck. 9x2¼ or so

(3)  (1)
Anonymous

by Anonymous on Jan 31, 2025 at 6:46 PM

I was always trading my boy's underpants with the girl down the street and my mom and her mom gave up on trying to keep us in our actual underpants. When I started 3rd grade mom got rid of all my girls things and grandma was my only sympathizer. She usually watched me weekends and she bought me really pretty panties, dresses and skirts. My mom's up in the attic were even nicer and I could be totally girl with grandma.

(3)  (0)

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