Sissy Boyfriend Stories

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Kim's New Life Ch. 02

by JanetMon on Feb 12, 2019
First Time

"Whoa, Kim! I'm sorry. I didn't mean to make you so upset. Please forgive me. Since you have, or rather recently had, a serious relationship with your boyfriend, I know you couldn't be a lesbian. That's why I said you answered my question. Therefore, I assumed you must be bisexual." I think the alcohol was helping me to be more than a little pissed at her i...

The House with Blue Shutters Pt. 02 Ch. 01

by BenGarland on Sep 24, 2019
Erotic Couplings

PART 2 - TET HOLIDAY 1. MORE SHENANIGANS It was January now, and the Lunar New Year holiday was nearing. Tuyet would come back home for about three weeks, and we had already talked about seeing each other. She suggested going to my fantasy coffee shop first, the one where I had wanted to take her after our Tuesday lunches, back last summer. There would be...

The Trade Show

by gangbanger69 on Oct 10, 2018
Group Sex

Story of a hot single mom who works as a food broker in a male dominated field. Donna woke early, she needed to be at the Marriot hotel at Newark/Liberty Airport by 7 am for her first food show. She had worked as a food broker for AD Garvis for five months, her job was to get food products into businesses around the tri-state area. In a short time Donna had...

First Time Anal

by pollyplummer on Mar 18, 2020
Anal

(For clarification. All events in this story occurred when both parties were 18 years old). My first real boyfriend was Kevin. He was on swim team and had the kind of body I like-- thin and strong but not bulky. He had strong Germanic features, curly dark blond hair. He treated me well, too, never cheated and always showed caring about me and my feelings. I...

The Awakening of Polly Pinnick Pt. 02

by UpstairsInterest on Mar 17, 2020
Erotic Couplings

In the end I did two rather bad things following sleeping with Nick's brother Ryan. The first was I didn't say a word to my boyfriend, keeping it to myself in the hope I could salvage the relationship while dealing with my guilt. The second was based partly around the first, and that was that I accepted the offer from the other university in the city we woul...

The Peeper and the Bitch Ch. 11

by SaviorSamurai on Jan 29, 2019
Erotic Couplings

Time passed. "Seriously, woman?!" Forty-three Sora said in a roar, holding his wife's cellphone, which displayed messages between Sora's wife and a police officer Sora was friends with in high school. "You want to suck him off today?! It's already bad enough I just found out he paid to have sex with you. How many other guys are you prostituting yourself to?...

Peach Picking

by MemberX on Sep 14, 2020
First Time

This all happened back when four teenagers could wander through an orchard on a warm summer afternoon without wearing masks and maintaining a social distance. More than sixty years before, in fact. 1959. Don't worry, though: age hasn't dimmed my memories of that day. My boyfriend Dan's uncle owned a pretty big stretch of land upstate: a farm, actually. He...

Revelations of Amanda Ch. 01

by Alkino on Sep 28, 2020
Exhibitionist & Voyeur

It was half past two in the morning. Since it was a Tuesday, most of the city was asleep, as always, with the usual exceptions - hotels and gas stations, night shift workers, insomniacs and lonely souls of all kinds. Gusts of wind brought promise of rain after several intolerably hot days, blowing scraps of discarded newspapers down the sleepy alley beneath...

My Last Night of Freedom Ch. 03

by Sungmehetu on May 4, 2020
BDSM

Lindy The cussing from the basement was loud enough to reach the kitchen. Domina was upstairs, recently fed, and I spent an hour at church. Johanna came down stairs after her turn at church and relieving Domina's bladder. Two plates were on the floor with eggs and sausage on them. "Honey I need you. She filled me up." Johanna said. So I lay on the floor a...

ENF Dot Com - A Wandaverse Spinoff Ch. 07

by Pugzilla on Apr 22, 2020
Exhibitionist & Voyeur

The happiest day of Josh Fields' life was the day he and his friends ambushed their classmate on the beach. Wanda was a beautiful black girl with huge round tits that looked like half watermelons that sat on her chest. Most of the school had shown up to watch them pull Wanda's bikini top off. Wanda squealed in embarrassment and Josh almost came in his shorts...