Naughty Boy Spanking Stories

143,747 results
Orientation
Length
Source
Infinite Scroll

Vina's Salon of Spanking

by Blackz_Sidez on Sep 14, 2017
BDSM

When Arnold first saw the ad, a small display in the back pages of City magazine, he couldn't believe his eyes. A middle-aged man, with his pants pulled down to his ankles, was stretched across the lap of a buxom young woman. She was in the act of delivering an apparently sound slap to his buttocks, which were discretely covered by his underwear. Both the ma...

Man Disciplines Sissy Ch. 01

by LanaBehave on Sep 14, 2017
Transsexuals & Crossdressers

I enjoy nice undies, sexy undies, soft and pretty lingerie, and delicate and dainty clothes whenever possible. I put on these things, and feel feminine and aroused, eroticized....the pretty dress, the wig, the nylons, panties and bra, heels... I also feel the misbehavior aspect. A boy/male like me, even if it looks sexy or feminine on me...dressing girly is...

A Clearing of the Mind

by MNBobKatt on Sep 19, 2017
BDSM

Tom was not having a good day. Things at work had reached a boiling point, and although he hadn't meant to, he had lost his temper yet again. His co-worker's feelings were hurt and he felt like a jerk. His mind kept spinning on the following three questions, "Why does he do this? Why can't he just control his temper like his does everything else in his life?...

"I'm a Naughty Girl!"

by Back2egg on Jul 11, 2018
BDSM

The thought of spanking a girl over my lap was the pinnacle of my sexual desires. The trouble was that this was before the internet and spanking was rarely mentioned. There were drips and drabs gently alluded to on TV, in books and now and then in the newspapers. I was also aware of certain specialist publications but I was far too repressed to buy them. T...

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...

The Bet Ch. 04

by MutableMalachi on Dec 23, 2017
BDSM

Author's note: This is a continuation of "The Bet" chapters 1-3. The plot will make a lot more sense if you go back and read the whole thing. Also, this story features a female-to-male transgender character with a gay man. If that's going to bother you, this story isn't for you. * I took his hand in mine and held it where he had it pressed up against my fa...

Three Days...with a Spanking Virgin

by naughtychanteusez on Sep 17, 2017
Fetish

Three Days At times caution can keep you alive, but it can also prevent you from taking chances beyond a reasonable comfort zone. That's exactly what I did recently, threw caution to the wind and stepped out of my comfort zone to meet a woman I got to know on Literotica, an internet web site. From the start, one of the things that made this different was ou...

New Female Boss Asserts Herself

by Orchid56 on Sep 17, 2017
BDSM

I have worked in the same office for a few months now doing general secretarial duties. My former boss was often absent and staff took advantage of this to come in late and spend time emailing friends rather than complete work on time and eventually he left the company under a cloud to be replaced by a much older, mature woman. One Friday, at the end of the...

Days of the Raj Ch. 01

by aaronburr on Sep 17, 2017
Exhibitionist & Voyeur

(Let me lead you through the sepia-toned, historic setting for this tale - colonial India - where you will experience some of the most delicious Clothed Female Naked Male fun you have ever come across. On the banks of the Ganges the senior boys' college was filled with aristocratic 18 year olds, thrillingly subject to the discipline of female English teacher...

Joan Takes Charge Ch. 12

by cynthiablaine7 on Dec 2, 2019
Fetish

With much affection and thanks to Ralph. [This is a chapter in a series; it will make more sense if you read the earlier chapters first but you need not do that to enjoy it. This story does involve bodily functions and some significant disciplining, so if any of that bothers you, please read no further. All characters are 18 or over.] ***** For some time...