Sissy Blowjob Stories

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Jessica Ch. 02 - Vanessa

by Floydman1 on Dec 16, 2019
Transgender & Crossdressers

Her name was Vanessa. She was very cute, about 5'4", slim, with big brown eyes and skin that was very clear and smooth. We had met online, of course. She had reached out to me for advice and friendship, as I was an experienced transwoman. After talking online first and then over the phone, we met in person. It was at her place, since she wasn't all the way...

Holly's New Start

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

I love Jamie so much it hurts. I mean there's a lot of things that would have people freaking out over this relationship of ours especially how I am and how we started. Jamie loves me despite my past. And like he really, really only has a sort of little picture of just how bad I was as Holt. Only he found reasons why Holt ended up so broken. No, no excu...

Neighbourhood Terror to Sissy Pt. 22

by Fibaro on Jul 6, 2020
Transgender & Crossdressers

Chapter 24 "Okay Marcy, now get back up and Minthe back to the vanity table. Jutht like it'th important to know how to apply makeup, it'th important to know how to remove it ath well. After all we don't want you developing a bad thkin cauthe of all the makeup you're uthing." Stephanie ordered not even giving Marcy a few minutes to deal with what had just ha...

The Entertainment Ch. 02

by econut on Sep 16, 2017
Fetish

I had just finished cleaning up after dinner when the doorbell rang. Master and Mistress's guests were here. I had been instructed to let them in when they arrived. I was nervous as I walked to the front door. Gary and Lana, my Master and Mistress, had never had guests over while I was here. And until today, they had never made me dress in drag, and now I wa...

Hung like a Grape Ch. 03

by sissysherry2 on Apr 10, 2018
Transsexuals & Crossdressers

The story of our sissy heroine concludes... this is the third chapter. Lisa had pegged and tagged Sissy Sherry in the last chapter and took her shopping for new lingerie for the evening's festivities. She opened the door in a sexy pink nightie with full makeup. I plan on concluding the tale here but that will depend in how well it is received. Thanks to th...

Femboy Autocracy

by Azaylia on Mar 1, 2021
Science Fiction

In 2027, a mad horny scientist unleashed her diabolical weapons in an attempt to turn the world into her sexual paradise. She released two custom-made viruses. one that would affect men, and one women. They rapidly spread to the entire population, brining their effects with them to all but 0.00001% of the population. For women, the effects caused futaficatio...

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Connie Goes to College Ch. 06

by cmorehead on Sep 25, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * My freshman year in college became quite a year for me in terms of defining my f...

Taken Too Far Pt. 02

by SwitchSissy on Mar 10, 2020
Transgender & Crossdressers

"Good girl" He smiled in approval. "Now, I noticed something earlier, when I was clicking that new, secure padlock onto your clitty" he reminded me, pulling me up so I was now sat on the bed, my arms bound behind my back with duct tape. "You've written something there, and on your thighs. And I think I can also see something on your belly button too, you lit...

From a Husband to a Dutiful Sissy Ch. 04

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers. ***** Chapter Four: Moving on to reinforcing my new lifestyle Satu...

Black Sissy For White Goddess

by Samuelx on Sep 16, 2017
Interracial Love

Finally, I feel like I am where I belong. Picture this, if you will. A big and tall, muscular Black man clad in a pink tutu and frilly White panties, my face fully made up and my lips properly rouged. I am kneeling before a six-foot-tall, slender red-haired White chick and sucking her strap-on dildo. My Mistress Amelia Heinrich smiles at me as I suck her dil...