Sissy Cheerleader Stories

12,762 results
Orientation
Length
Source
Infinite Scroll

Restructuring Pt. 03

by cathynylons on Jan 29, 2020
Transgender & Crossdressers

My wife said, "Well now it's just us girls. Leland is going to a bar to watch the football game with some pals. But it's only 4 pm." Looking at Diane she continued, "It's so great to have you here, Diane, after so much time. It's great that we are re-connecting...and that our husbands get along so well. Ha Ha." "Yes," Diane agreed. "There is some good chem...

Cheerleader Humiliation Ch. 01

by ButtPlugBitchBoy on Sep 17, 2017
BDSM

Shivering, cold, feeling weaker than ever before, I look up at them with my heart beating a million miles per hour. From my vantage point... the dim wet tile floor of the girls locker room at my high school, they seem to tower over me like strange Satanic titans. I'll capitalize the letters in titans that were most obvious; TITanS; TITS. I can see their pa...

Just Like My Friend

by purekink on Sep 12, 2017
Transsexuals & Crossdressers

I suppose it all started after my friend told me his girlfriend liked to dress him in her clothes before sex. I couldn't quite believe it - he was masculine and muscular, a real man's man. He'd confided in me and I teased him about it unmercifully. I mean, really? Being dressed in women's clothes? That was supposed to be a turn-on? He seemed to think so, bu...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

Haven the Sissy Slut Ch. 01

by CSK on Sep 11, 2017
Transsexuals & Crossdressers

He was sitting on his couch, naked, remote in his hand watching the pre-game show for the 12:15 start time for the football game. It was the first of three blocks of games for the day. I was on my knees in front of him, dressed like a slutty maid or something with white thigh highs that were topped with little white bows, an extremely short black, frilly ski...

How Friday Got A Reputation

by alice247 on May 11, 2020
Erotic Couplings

How Friday got a reputation "Oh, my fucking God!" Sissy McDowell gasped as she reached into my boxer shorts. "That's all you?" I pulled my face back from her neck and straightened up. "Yes. What's the matter?" I responded defensively, certainly unsure of myself and her reaction now that I had my hand on first base. "You're fucking huge!" She exclaimed wit...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...

Summer 1974

by stevessv on Sep 23, 2019
Erotic Couplings

A week before my last day of high school in mid June of 1974, I had my first date with Kin. When I say "date," it wasn't something we planned because that was when I first told Kin I had a thing for her and we kissed. We kissed in a wooded area, behind the rec center, a converted white church built in the late 1800s, near the center of town, where we often a...

Sissification 101: Ch. 02

by silkstockingslover on May 18, 2020
Toys & Masturbation

Summary: Both Eric(a) and Joan discover the joys of toys. Thanks to the real Eric who requested and helped plot this lengthy story. Thanks to Tex Beethoven and Robert for editing this story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose wat...