Spanking Boy Stories

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Infinite Scroll

The Understanding

by PantywaistKen on Sep 16, 2017
Anal

He felt that she understood that this was something he had always needed; but he hadn't known how to get his needs met. As a boy, right through his teens, he never had experienced the special kind of physical intimacy that he had required. From his toddler years when his mother had so completely vanquished him in the 'battle of the potty," he had always fel...

Further Adventures of Susan Adams Ch. 03

by SteveLee1146 on Sep 14, 2017
BDSM

THE FURTHER ADVENTURES OF SUSAN ADAMS 3 (of 7) As it happened, Don was not there, so they went up to the bedroom to rest and wait. They were still on a "high" from their erotic afternoon, with Jean teasing Susan about her indecent behavior. "I think I'll tell Don about you showing yourself off like that, and I'll bet he'll give you a real spanking for being...

Ms. Nelsons New Boy

by Peroxide_ on Sep 16, 2017
BDSM

It was a sticky Friday afternoon in late June. Paul, having just graduated high school, had a lazy summer sprawling out ahead of him before the start of university in the fall. Most everyone else had gotten summer jobs, and so except for the weekends, Paul had to entertain himself until his buddies would get off work. For the first few weeks he made do, gla...

M.I.L.F. vs Stud Ch. 02

by mrsmillwood on Sep 19, 2017
BDSM

July 10: Lord M, I am intrigued. I look forward to your thoughts, although, I'm not sure Derrick will! "Under my thumb", Derrick is...at least the vital part of him is. ;) I'm not sure what the critic expected. It was under the BDSM category.. Mrs. Millwood * My Dear Mrs Millwood, I must say I was delighted to see your name in my inbox this morning....

Chastity Keyholder Sexting

by her_pantyboy on Aug 31, 2017
Fetish

This morning my Keyholder was at work and i was 1200 miles away locked in a CB6000s chastity cage with a plastic numbered lock (485807). i was telling Her how much i missed Her and we were just talking about everyday life, when in the background i heard one of Her male coworkers bring Her a cup of coffee. As he gave it to Her, She said, "thanks bitchboy". i...

An Old Fashioned Southern Whipping

by sarah thorne on Sep 17, 2017
BDSM

You know, people talk about banned implements all the time. Implements that they would never allow used on them or even implements that some say they would never use. For whatever reason. Bad experiences in the past or just an overwhelming fear. I once had that mindset, particularly about a leather strap and also a cane. The strap from the memory of it havin...

Mistress Meets Biker Boy

by glorialamuse on Sep 16, 2017
Transsexuals & Crossdressers

I have been cross-dressing since I was a young teenager trying on my mother's clothing whenever I had the house to myself. I was now out on my own and between relationships. I thought I was a heterosexual male, having only had sex with females. I was not attracted to males at all. All my relationships were with females, several long-term girlfriends included...

Vivian Ch. 04

by scienceguy950 on Nov 16, 2020
Fetish

(Suggest you read one of the earlier Chapter's first; the story will make more sense. Hope you enjoy). I was driving to get takeout Chinese food for three after my modeling show with Vivian and Li. When I returned from picking up our food, the two women sat on the couch in Vivian's living room, both clothed now, chatting and drinking chilled water. Ladies...

How to Spank

by Joseki Ko on Sep 12, 2017
How To

So this is your first time to deliver a spanking, and you need a little help. First and foremost only use your hand for your first few times. If you get a little excited or enthusiastic using an implement (Paddle, tawse, belt, etc.) you might hurt your subject a lot more than you intend. Remember you are responsible for both your subject and yourself. From...

The Facility Ch. 01

by spankmehard1984 on Sep 14, 2017
BDSM

For as long as I could remember, I had always wanted to visit a strong woman who would put me over her knee and give me a long, hard, thorough spanking. I tried to repress these feelings, but this made me miserable. I looked for clues in very person I met, hoping, they would have this shared desire of mine, but I felt totally alone and isolated, like a freak...