A Chance Encounter in the Park at Night
So back in CL day I meant a str8 guy and we first started emailing and them decided to meet. First time I put on my maxi dress and heels he came over I pulled out his 10+ bbc deep throated the hell
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A Surprising Connection at the Bar
I'm a mature crossdresser was out looking for a masculine older man. Been moving around the bar looking. Was getting late, sat down and had last drink of the night. Then I was surprised to have
An Adventurous Night While House Sitting
I was house sitting for a relative and felt a little adventurous, so decided to create an ad for myself. I don’t normally have intimate experiences, so this was my chance since I’d be
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An Unexpected Connection with a Younger Man
I am a passable crossdresser. I am 100% bottom. I LOVE pleasing top daddys. I prefer older, more sophisticated men. I have a tendency to hook up with top daddys that are 55 yrs and older. (I am 48).
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An Evening with Friends and a Sissy Submissive
I'm a 30 year old sissy CD, behind closed doors. I'm 5'11 220 light brown hair and smooth all over. Masculine acting at work. I've been serving a Dominant man for about six months
Reconnecting with a High School Bully After Years
I have always been somewhat flamboyant. Always had a feminine side to me. In high school, i was the only boy that took home ec. I was called all sorts of names:flamer, fag, queer, gay, fruity, etc..
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A Night of Surprises at My Sister's Party
I'm 25 5'6 about 150. Totally passable when I dress. I was visiting my sister for a few weeks last summer. She had known about my other life since college and supported me all along. She
An Unexpected Connection at the Bar
I'm a 27 year old CD, extremely passable when I go out. At my job I dress as a man. I have a runners build, stay smooth all over. I'm 5'9, brown eyes and short brown hair. My curse or
An Unexpected Visit from an Older Man
So i am a total bottom sissy. I love pleasing top men. I am semi passable when dressed in my fem clothes. I am bisexual, although i prefer men 99% of the time. Havent been with a real woman in a few
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Unexpected Connection at the Gym
I guess you could say i live a double life. I have been crossdressing my entire adult life. When dressed, i am very passable. I wear wigs, makeup, fake breasts, and womens clothes. When im not
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An Unexpected Night at the Country Party
I am a semi sissi gurl who loves men. I have several suga daddies that live out of town, who when in town, i take care of.
I had a daddy that was supposed to come in town a few weeks ago. He
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By Deleted User
A Day Off Turns Into an Unexpected Encounter
So my wife was away on a business trip and I had one PTO day to take for the year so I took it when she was away. I went on CL to look for some fun. At that point for W4M section was filled with
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A Journey of Self-Discovery and Connection
When I was younger I used to crossdress on my moms clothes when she was away. I phased out of it as I got older. Now years later and married I for some reason just got the urge to dress. I took a
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By Deleted User
A Weekend Surprise with Friends and Secrets
I'm 28. A masculine husky guy at work. When I'm off at home with my girlfriend I CD as BBW. She's very supportive. She's attractive and totally into it. Our sex life great . She
An Unexpected Encounter in Brooklyn
Had a work day that ended early in the afternoon and thought, why not put an ad up and see what happens? I'm a 31 year old CD in Brooklyn that has been dressing for a very long time. My legs
A Night of Unexpected Connections with Older Men
I'm a young beautiful 27 year old TS. I'm not a CD. Long Blonde hair, perky 34C tits, a nice round ass and small 5 inch penis that tucks nicely in my bathing suit. Extremely passable, no
An Unexpected Encounter at Ohayocon
Ok so this one happened back in Janurary pre Covid I'm a bi sissy and a cosplayer attending Ohayocon in Columbus when I'm in full make up wig I can pull off a female character it was
A Weekend Visit with Sibling Turns Surprising
I'm 27, fit 6'. Masculine at work. Stay smooth from the waist down. I enjoy CD behind closed doors or when with other men. My older sister always knew I was a femme in school. She suspected
An Unexpected Encounter in Indianapolis
I was in Indy, post a had wanting to train my throat. I still can’t do it all the way though would love to learn.
He walks in, I’m in lingerie, heels and make up. Sets down on the edge
Unexpected Roommate in a Golfing Friendship
Earlier I had shared with you my story about my golf buddy and roommate. We had been sharing a home to help with expenses and things. I finally lost in a golf match and I had to be his bitch. It
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