Shemale Dating Stories

35,053 results
Orientation
Length
Source
Infinite Scroll

Ice Cream

by ilovebananas on Mar 31, 2020
Erotic Couplings

*This story has its origins in an email sent to me by an acquaintance. It turns out we had been hot for one another for a long time* * The dream came to me again, but this time it felt different. It felt different because I could see the face of my would-be lover. The dream always began with us naked in bed in the pre-dawn light, silently enjoying each oth...

Meeting My Trucker

by misstrust on Mar 31, 2020
Exhibitionist & Voyeur

****Introduction**** This story is based on a couple in a long distance relationship. He is a dominate male and over the road trucker. She is a submissive sub with traits of a little. The two characters in this story have been dating for a few months. They have met before and have agreed to meet this time using the dom/sub roles. Thank you for reading my...

Winter Soldier's Soulmate Ch. 12

by Her11 on Apr 13, 2020
Celebrities & Fan Fiction

It was two boring days of thinking and hoping before a letter arrived in the mail addressed to Lucy. She knew who it was from. When Jarvis told her about it she raced to the mailroom, picked it up from a very frazzled looking intern named Jamie. He seemed nice enough if a little all over the place. But looking at the state of the mailroom it wasn't surpris...

The First Days of COVID Quarantine

by xeriscapartist on May 11, 2020
Mature

The Coronavirus has had us under a state mandated, shelter-in-place order for several days now. The stress and uncertainty of it all had us both wound up very tightly. A nervous, uptight and grouchy couple is no fun. Cabin Fever was definitely kicking in at our house. He had reason to go see a client a couple hours from home on Thursday. I decided to ride a...

Elevator Ride to Slut Wife

by monkeykinglives on May 13, 2020
Loving Wives

Compliment leads to elevator group sex with strangers. Tags: cunnilingus, submission, dress, hotwife, slut, elevator, spank, stranger, blowjob * After a year of marriage, my wife and I decided we wanted to go to a fancy New Year's Eve party at a nice hotel. Every large metro area has several to choose from, and by coincidence, they are all on the same nig...

Stacey's Boyfriend won't Pee on Her

by usuallywellred on Jun 9, 2020
Fetish

Every year on the first day of summer a group of us rent a lake house in Michigan. Stacey, Darren, Jacob, Alyssa, Tiffany, Mark, Rachel, and myself all carpool out there. It's a four-day weekend where we sit in inner tubes, drink beer and float on the lake. At night we light a campfire and drink a little more. It's a pretty chill weekend. The first day was...

May Flowers

by HopelessPragmatic on Jun 9, 2020
Fetish

(Warning: This story contains frank description of menstruation and menstrual sex.) * All she wanted was some fucking M&M's. It had been three days, into the warmest day in May, so far. She had masturbated thirteen times, hoping an orgasm would diminish her pain. It didn't seem fair that the week she had off, be spent in agony. She had tried everything to...

Erica's Hot Summer

by Tomhansom on Jun 9, 2020
First Time

Erica's Hot Summer This is the follow up story to "Erica, My College Virgin". You do not have to read it for this story, but if you want context as to this story, please do. This story happened the summer before we met. This story is true according to what Erica has told me. I did add some "embellishment" for the details she left out. It was a beautiful su...

The Mystery Box Pt. 01

by Brander on Jun 9, 2020
BDSM

A new life with a new wife and the acquisition of a sealed box, the contents of which were destined to change our lives and teach me more about Susan and myself than we thought possible. Susan was the intuitive one in our partnership, meticulous in attention to detail and extremely sensitive to emotions and feelings, while I represented a more happy go luck...

I'm a Hotwife Now

by alisafrench on Jul 6, 2020
Loving Wives

My name is Alisa French and I'm a Hotwife from Boise Idaho. It turns my husband on seeing how much of a whore I can be. The crazier I get, the more he loves it. About 10 years ago we started trying new things to spice up our sex life. We found several "dare" and wife sharing websites and made profiles on them. The first post we put up on the dare site I was...