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Chapter 20
What's next?
Let Tammy list some options and live to regret it
"I don't know!" You snapped at Tammy. You were in a really bad mood right now. Your ass was sore from the short hand spanking, your penis was erected to the point of being painful, you were so close to cumming that a gust of wind would send you over, and you were still butt ass naked in front of a girl with one of the lowest social standing at school. You were not in the mood to play nice right now. "You're the one obsessed with spanking dudes, think of something."
Tammy was too busy staring at your throbbing erection to notice your attitude. You're tempted to cover it but you doubt the nerd would let you and any sort of contact might send you off anyway. "Let's see, how about the wheelbarrow position?"
"Wheelbarrow position?"
"Yup. You'll lay down with both your legs on either side of me with your red butt in the air and your penis on my lap. Your upper body will be laying down vertically to the floor-"
"No!" Your face manages to go redder imagining yourself in an even more exposing position than before. Not to mention it didn't solve your problem of not wanting Tammy to make contact with your dick. "Why would I want to humiliate myself? Think of something else!"
"You're being really mean to me. That's not good business sense to be rude to your partner you know." Tammy crossed both arms in annoyance. She was acting like she was throwing a tantrum, but you know her well enough now that this was some strategy to get you to do what she wanted. "I think I'll just take the slaps I got in already and leave with the mask if you're going to act like that."
"No, don't!" Your voice comes out more like a whiny plea than you intended. But you can't afford to let her take away your only hope in covering yourself at this party. "I'm sorry. Can you please list a few more ideas?"
She smirked, pleased with your change in attitude. "You may be the only cute naked boy to ever come to me asking for a spanking and enjoy it, so you do have some leverage too. Sure!" She thought about it longer. "Well you can bend over the couch I guess. Boring, but it'll give me better leverage to spank harder." Your sore ass tensed at the idea of even more sting. Sure you'd be unlikely to cum in that position, but it really worth it? You're not sure you can handle anything more painful than what you were already given and if you stop the spanking before the agreed upon spanks you might have gotten your bare ass slapped for nothing and then have to do another humiliating deal anyway.
"We can just do it standing too. I'll kneel on the side of you so I can spank your tushie and examine how hard your weiner is at the same time." You cringed at that too. Another one that would save you from cumming, but can you really handle that? Tammy making comments about your twitching cock as she slapped your ass?
"Oh! Or the diaper spanking!"
You frowned. "That better not mean what I think it does."
"I'm not into diaper play if that's what you're thinking. Gross." You rolled your eyes. She apparently fetishized spanking men on the bare ass but that was where she drew the line. "It just means you'll be laying on your back as if you were a baby getting diaper changed. Legs in the air, spread wide open in this case, and butt raised. Then I'd spank you like that." Tammy stopped and thought hard for a second. "I'd be willing to spank lighter if you chose this one. But I'd wanted more spanks to be fair." She must have realized how humiliating this position would be with your penis once again exposed and decided to sweeten the deal a little bit. Admittedly you are nervous getting a spanking as hard as she hit you earlier, maybe taking softer swats would prevent you from emasculating yourself with embarrassing noises and squirming. You can just take the rest silently and get it over with.
That made your choices over the couch, standing up, and the diaper position. All humiliating, but all safe from a humiliating accident. You could also do that wheelbarrow position she mentioned. Tammy did tell you that you had some bargaining power here too since she was **** to spank you. You'd spunk over her lap and humiliate yourself but it'd be worth it if you could convince her to give you even more clothes from it.
What position do you choose?
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Naked and Embarrassed
An enf and enm story
You've experienced embarrassing stories of others getting stripped in third person on this site, but what if you were the one to get naked in front of tons of people? Varying locations from a high school, the beach, or even your work place! Be male or female and decide whether to have bright red cheeks alone or with a friend in this interactive story!
Updated on May 25, 2026
by kingkhan19
Created on Sep 17, 2017
You can customize this story. Simply enter the following details about the main characters.
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