Wedgie Dare Stories

42,476 results
Orientation
Length
Source
Infinite Scroll

Kim's Shop Adventure

by blondefungirl on Sep 17, 2017
BDSM

I read the other adventures of Kim and I couldn't resist re-telling my own encounter with this little lady. From the sounds of her exploits I take a small amount of pride in starting her on her "pleasure path". My name is Tommy and I went to high school with Kim. She was a very popular girl and hung with the "in crowd". I, on the other hand, while popular i...

Letter From Palo Alto

by justincbenedict on Sep 17, 2017
BDSM

LETTER FROM PALO ALTO Dear Shoeblossom, My wife Lillian is also the keyholder to my Prince Albert piercing. Much of our time together my cock is struggling to erect against the cruel way it is locked in a bow shape against the piercing in my testicles... Lillian teases me a lot, and spends hours walking around in front of me wearing very little...demibras...

Barking at the Right Tree

by blue_kiti on Sep 17, 2017
BDSM

Sarah stares upwards at the leafy, green tree. She can still make out its beautiful colours even in the diminishing light. It is dusk and the sun is setting; the birds are singing their good-night songs. They may be going home safe to their little nests, but Sarah wonders how much longer she will be out tonight. A sudden gust of wind begins to stir the leav...

Being Prey to the Night

by chloedeboncourt on Sep 17, 2017
BDSM

It is the lonely hours that get to me. I can deal with nearly everything. But when the night is dark and long, boredom and some primal longing for adventure overcome me. To play the game of the unprotected prey, to throw the dice and let fate decide the night. This is the moment when I leave my apartment against my better judgement in the middle of the night...

Breaking Him

by Bruno1027 on Sep 13, 2017
BDSM

I was 20 and had just moved to Boston. I didn't know many people and had yet to find a place to live. I was still living with my brother. On a trip to the supermarket I noticed an older woman in the checkout line giving me the eye and a wide smile. Being the shy type I didn't reciprocate but managed a weak smile and nod. I paid for my groceries and left. I n...

Building the Perfect Slut

by kitten1964 on Sep 15, 2017
BDSM

Kori walks past the desks of the members of the office, loving the fact that their eyes are all on her. She especially hopes one of the pairs of eyes is watching her and watching very closely. She even dressed specially for this – no bra and a silk blouse, so that her nipples would be in a constant state of arousal, no panties and thigh-high stockings held u...

Gratitude

by gentlyhardly on Sep 12, 2017
BDSM

After a lovely evening out on the town, we head back to your place. Once you close the door behind us, you step behind me, sweep my hair aside, and kiss my neck gently. Then you say, "You know, I had a nice time tonight, but there were a few things that could be improved." "Oh?" I say. "What do you mean?" "Why don't you go back to the bedroom and wait for...

Mistress Jamie Return: She Does

by gomez8 on Sep 17, 2017
BDSM

Mistress Jamie has been keeping watch over me. She read my story and has responded. This is her message to me. ------------------------------------------------ "I can't believe the new levels of boring these conferences have reached." You think to yourself as you take a vacant stool at the bar. "What can I get ya?" asks a female voice. "Damn! She is mighty...

A New Week

by GlaciersGold on Sep 17, 2017
BDSM

She remembered the first time they had met, how shy he had been, how uncomfortable she had been. The city bus was silent, and sitting several seats behind him she felt this uncontrollable need to confront him. Only after weeks of tension had she dared speak to him. Now here he was forcing guttural moans out of her as he towered above her. It was only a wee...

Amy Becomes A Sub

by 4realwomen on Sep 12, 2017
BDSM

Hi! My name is Amy and this is the story of how became submissive. In high school and college I had boyfriends and did a lot of partying with them, but they never seemed to turn me on as much as I wanted. They all seemed kind of wimpy and always did what I wanted to do, even if they didn't want to. That made be put them down and treat them bad; I just wanted...