Shemale Dating Stories

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CFNM with My Wife's Friends Ch. 01

by CFNMatt on Aug 21, 2018
Exhibitionist & Voyeur

The old adage goes that hot girls seem to travel in packs. I found this to be true when I started dating my now wife, Jen. She is a gorgeous woman with a nice tight body. This description could easily describe 5 or 6 of her best friends. To follow is the first of a few stories where I found myself naked with her sexy friends. Names have been changed. First...

Woman of Her Dreams

by mistyfdfa on Feb 7, 2018
Transsexuals & Crossdressers

  (Story No. 180) It had been nearly six months and he still had no idea about the secret she was concealing. It is time to tell him, to show him, just what kind of woman he was dating...   This story is rated NSFW for explicit sex and nudity. It also contains sex changes, sexsomnia, a guy sucking dick, bukkake, stamina enhancement, penis expansio...

Friendly Examination

by writingdirty on Feb 7, 2018
BDSM

It started in such a simple and silly way. A bunch of us were out, in a crowded bar, huddled in small groups so we could hear each other, and the topic of grooming came up. Kimberly tended to be the quiet one in our group and because of that I always tended to gravitate to her, to try and include her in conversations, to try and pull her out of her shell. P...

Rough Love

by MivannaRai on Mar 7, 2018
Erotic Couplings

I ring the doorbell before rocking on the heels of my shoes. He picked a good place to live. My gaze moves around as I graze over the cute little neighborhood. My phone buzzes in my back pocket causing my brows to furrow. Using my thumbprint, it unlocks to a text message. Doors unlocked. I sigh, putting my phone away. He's something else. After adjus...

D***, My Friday Night Date

by Aimlessness on Mar 7, 2018
Erotic Couplings

So, I was asked for a follow up on how my date went. Before I begin, a little further backstory. You should probably understand what has led me to this point in my life that I'm about to strip naked for you. D*** has been a persistent itch in the back of my brain for weeks. We met on a dating site and he contradicts himself in his very first correspondence...

Desperate Need

by Turbidus on Feb 6, 2018
Erotic Couplings

I need his cock, perhaps more than I've needed anything recently. My fingers fumble at his belt. I don't waste time on cursing the delay. I force myself to take a deep breath and focus on slowing the pounding of my heart. I press my mouth to the front of his pants and blow my hot breath through the thin linen to distract him. When I reach for his belt again...

Welcome Wagon

by doctoryes48 on Feb 6, 2018
Loving Wives

"HI, Honey. I'm home," I called out. "HI, I'm in here," my wife answered, calling from the bedroom. As I climbed the stairs to our bedroom, I told her that it had been a tough week and that she should get dressed because I was taking her out to dinner. "Oh, sorry Honey, but I have a date tonight." I stopped dead in my tracks, speechless. What, a married...

Blast from the Past

by VictorCharlie on Feb 6, 2018
Loving Wives

Katie's close friend Anthony was staying with us for the weekend. Katie and Anthony grew up a block from one another, and their families were close. A perusing of family photos shows the two families present for a litany of BBQs, birthdays, family vacations, and the like. It is safe to say they are the best of friends. I'd wager Anthony is closer to Katie th...

Mom & Me Ch. 06

by Yechesem on Mar 20, 2018
Erotic Couplings

Am I Ever Going To Get Myself Out Of This Mess? I left the counseling office and headed back to class with the image of Mrs. Wilson's lavender panties illuminating my mind. Not just any lavender panties, but Mrs. Wilson's lavender panties. I kept thinking about her and all that had happened while I was in her company last period. I saw her sweet ass as she...

My Friend's Wife

by JeanGenet on Sep 12, 2018
Fetish

It was a rainy Friday evening. My friend, Matt, and I had been drinking at the downtown pub where we have met every Monday and Friday for the past six years or so. Somehow, the conversation steered towards sex. The subject of sex doesn't come up too often, and, in the past, Matt has been pretty tight-lipped about his bedroom sessions with his wife, Tracie....