Way Back When

I was having my first sex with a couple. It became bisexual, me having sex with the husband and the wife. I was always small framed, long haired, and no body hair, didn't even have to shave. Just body hair on my pubes. She got me crossdressing in lingerie, stockings, garters, bought me heels, and I made it with her and with him like that. I was not enamored with doing that at first, but I got used to it and eventually liked it. Long story short I was on my own at 18 and having trouble making ends meet. I had fucked a couple of girls outside of that relationship and 4 other guys, friends of the couple.

The wife had to go to her mothers to help her out and was going to be gone at least a month if not more. I was asked to move into the house and be his substitute wife for the time she was gone. It gave me a place to live plus some side money on my own. I was to do the cooking, cleaning, laundry, shopping, and of course be his sex mate, to be the wife. It was nothing I hadn't done only this would be done totally dressed and acting like a woman. It was that or move back home and that wasn't a good option. So before she left, she took me shopping and bought me all kinds of women's clothes, shoes, and more sexy undies and lingerie. For the next month I was his full time wife. I found the sex, much more satisfying, he was actually making love to me, not just fucking. Yeah, sure sometimes we just wanted to fuck and we did, but it was different. I was his wife, not just a piece on the side.

The month turned into 2 months, then three. The only time I wasn't made up and dressed up as a gurl was if I had to go visit my family. Eventually the wife came back, she stayed in the spare room, I had sex with her but it was more like a lesbian affair. They separated, not divorced, and I stayed with him as his wife. This went on for two years. Two years and 3 months I was a crossdressing, feminine, gurl. I cooked, cleaned, shopped, decorated, and of course had sex with my husband. Eventually; she came back into the picture, and I was out.

I don't tell anyone about this time in my life, I have a wife, and 2 kids. My wife is very adventurous sexually. I don't think she'd like to know that I was a crossdressing wifey for over 2 years though. The couple still lives close to my parents house, I see them occasionally when we go visit my parents, but we don't talk. I do play back the memories of being under him, my husband, with him between my thighs my legs wrapped around his back and him gently pumping in and out of me, sucking on my nipples, then jamming it in and feeling the warmth of his cum pouring into me. I miss it, but don't want to repeat it.

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Anonymous

by Anonymous on Apr 18, 2021 at 12:22 PM

I was a school kid and hadn't had sex with a girl as of yet but had been the recieving end of a few cute older boys intentions. The train was late getting in the station and I missed the bus for the last eighty miles to my grandparents house. I was going for Thanksgiving and to help my grandpa out who recently had a heart attack. An older farm couple in their 50's picked me up on terrible weather and offered me a place to stay and would drive me to my grandparents when the roads were cleared in the morning.
It was peculiar because she was every bit of 50 with a real short pink mini skirt on and nice legs too. She began fondling me till I embarrassingly shot my boyish load in my tighty whitey underpants. Her husband was closer to 60 drank beer and drove to a nearby chicken place and picked up a bucket of chicken for supper. My underpants full of my own gooey mess caused me to squirm a bit and she said "don't worry I'll get you cleaned up.
Lem her husband drank beer and ate chicken across the table from me as Cass said she was gonna draw me my bathwater.
It was quite embarrassing that me 15 almost 16 in six months was being given a bath by Cass and it was like a forever boner too. She washed my underpants in the bathwater, rinsed them in the sink and hung them over the shower curtain then dried me off. Putting one of Lem's flannel shirts on as a nightshirt she brought me to bed and pulled me immediately on top of her pantyless small frame. Her bathing me was foreplay for her and I guess me too, she guided my smallish boycock in her for my first time fucking. She gripped my buttcheeks tightly as I came and said aloud " Lem you're gonna like this boy's pussy, younger and tighter than anything we got before, it's perfect. " I didn't hear Lem come in the room but he watched the whole thing and feel of his weathered and calloused hands caressing the smooth skin of my butt was scary and strangely exciting. Cass alongside the bed held my hand as Lem pushed himself all inside of me as I whimpered "its too big, it's too big, stop, stop it..." Cass said "Shhhhh, it's gonna be okay, use gonna like it by the time Lem's through fuck'n that pretty boy's pussy you got. It'll be better than an hour so just relax..." As Lem continued wheezing and slowly fucking me Cass asked Lem excitingly "It's good ain't it Lem, he's just so pretty

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