Crossdressing Strapon Stories

2,832 results
Orientation
Length
Source
Infinite Scroll

Raped by My Goddess

by subsman on Sep 14, 2017
BDSM

We have been doing strapon play since we met, but I have always been limited to a small dildo. We had found one with a small head that vibrated and it has brought great pleasure to both of us. My Goddess, however has been wanting to use larger dildo's on me, both for her pleasure and to get me prepared to be fucked by a BBC which is one of her fantasies. We...

Emmy's Games Ch. 02

by hummmph on Sep 13, 2017
Fetish

"Well? Did Suzie help you fill the condom some more?" says the text from Emmy. I had just pulled my trousers back on after being jerked off by Suzie into a condom, which I had filled for the second time today whilst wearing panties Emmy had instructed me to wear. The stockings Suzie helped me put on feel amazing underneath my jeans. I can feel their tight g...

Sometime Things Change

by hottiehunter on Sep 14, 2017
Transsexuals & Crossdressers

I enjoy wearing womens clothing, my wife, Lori is aware of my fetish and doesn't object in fact she occasionally buys me clothes much to my delight. After several years I had accumulated quite a large collection of panties, bras, slips, dresses, shoes and other assorted apparel and accessories. This created the need for a wardrobe reduction due to limited st...

Strapon Sally

by fethishboy on Nov 30, 2002
BDSM

Pete was a scientist in a Lab. He was on top of his field. He had taking in a helper name Sally who was a cute flirt. It turn out bad when Sally turn out to have a dominant personality. She would push him around He was now paying this woman for doing nothing. She was 18 years old and dressed in skimpy clothing. She would use his house and push him around. Sh...

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Julia Takes Over Ch. 03

by bisubhubby on Sep 26, 2017
Fetish

Well, if you have read the first two installments of my story, you know what happened to me last weekend. If you haven't read them, here is briefly what happened. I went from a normal, relatively modest man to a cum licking, cum swallowing, cum slut slave to my wife. In one day I went from basic intercourse and oral sex to me eating my cum from my wife's mou...

Fantasy Night

by Ilovetoeatsperm on Aug 18, 2017
Fetish

One night while my wife and I were sitting on the couch she asks me what my kinkiest fantasy is. I asked if she was kidding? We do some pretty kinky things, a lot more than I'm sure most people ever even dream of. She keeps working on me and I finally give in and tell her one of my secret fantasies. I tell her how she knows I have an exhibitionist streak i...

Erika's Story

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame a...

Jenna & Stephen Ch. 01

by Naf_Noparts on Sep 12, 2017
Fetish

(Author's Note: This is a true story, one that tells of my hot experience with a friend who fucked me with a strapon. If you are bothered by the idea of women ass-fucking men with toys, then this story will not be to your liking. Thanks in advance for all constructive feedback!) * Jenna and I have been friends for nearly 15 years. We dated ever so briefly...

The Accident Ch. 02

by surferjake on Sep 12, 2017
Fetish

Jake's phone buzzed. New text message. Opening it, he saw it was from Sarah, and said "Did you just get into an accident? I'm so sorry. You should come over." It had been over a week since that day. Two girls had rear-ended him and brought him back to their place for an 'apology.' even thinking about it now, it sounded absurd. His phone buzzed again. "Well...

Blonde Fucks Blacks Ch. 15

by Samuelx on Sep 11, 2017
Interracial Love

There is nothing I love doing more than ramming my dildo deep into a black man's ass. I don't know why. I guess I'm simply addicted to it. Which explains why I've got my boyfriend Jackson Hall on all fours right now, face down and ass up. I gleefully slam my dildo deep into his ass. He squeals. I laugh heartily. I simply love that sound. Fucking black men in...