Sissy Girlfriend Stories

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Humiliated Sissy Slut

by Allice on Sep 16, 2017
Transsexuals & Crossdressers

I have been dressing as a woman at home in private for many years. No one has ever seen me dressed as a sissy slut before but I do it to feel sexy. I know I would never pass as a woman for I am 6 feet tall, 170 lbs and at the age of 45 not a real trim body. My girlfriend Rachel who lives with me is must younger at the age of 35 with a young trim body that h...

Lulu's Lockdown Diary

by lululuvsblack on Jul 6, 2020
Transgender & Crossdressers

Day 1 So, with this virus we've all been told to stay home and not have any physical contact with people outside, not get together in groups at all, and not even step out of the house if not completely essential. We're locked down. I guess it wasn't a great time to move in with a couple of guys I barely know, but there you go. There's nothing I can do about...

My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

The Blackmailed Sissy

by jmanrules on Sep 13, 2017
Transsexuals & Crossdressers

Jon walked into his roommates bedroom looking for the phone charger he loaned Eric the night before. As Jon was looking around he saw several pairs of panties, bras, and pantyhose. Not thinking anything of it Jon just grabbed his charger and left with it in hand. After he sat down it dawned on him that Eric has never brought a girl over and even if he did th...

Making a Cuckold

by jessijazz66 on Sep 19, 2017
BDSM

Brandi spoke nervously to her friend Jessica before she hung up the phone, "you're sure this will work?" Jessica understood her friend's fears, ever since they had begun discussing this plan of action. Jessica knew that Brandi was just starting to explore the depths of female dominance, and she knew that Brandi was worried about how her boyfriend, Brian, wo...

Teased, Denied and Sissified Ch. 01

by subbieman on Sep 11, 2017
BDSM

My girlfriend and I had been dating for nearly nine months when we decided to move in together. Her lease was expiring so it made sense as we had grown closer and she really seemed like "the one." We got along great and I loved her, but, to be honest, our sex lives had recently been lagging. I hoped that moving in together might rejuvenate it, but, based on...

How To Be A Boi Bitch Lesson 03

by gothicboibitch on Sep 13, 2017
Fetish

Did you enjoy our first fuck together, my darling bois? I know I did. I'm still thinking about it. Are you? Of course you are. And with that excitement, still, such shame. Making your cheeks burn. Making it difficult to look into your wife's eyes. To meet your girlfriend's gaze. You are no longer afraid. You are ashamed. Of what you are becoming. Of her fi...

Sissy's First

by CDJessie on Mar 7, 2018
Transsexuals & Crossdressers

This is a work of fantasy. (I wish my gf would do something like this to me.) *** I'm woken up to the blinding sun after Sarah rips open the curtains to our hotel room window. We were up half the night fucking our brains out, and I was pretty hangover "Fuck, you couldn't wake me up like a normal person instead of blinding me?" I ask. "Don't take that fuck...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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