Jes

She wanted to play 😈

I’m friends with an older man irl. He’s been into me for a few years and admits to jerking it to my pics every once in a while (I think it’s hot but i’d never admit that). He’s a dominant and has tried / begged quite a few times for us to get together even though I’ve friendzoned him HARD time and time again. He also sends me money, and wants me to start and OF just for him. One time we were talking about spanking and I was saying that it gets me absolutely dripping wet. he asked, if even if we didn’t fuck, if I’d let him spank me… I legitimately considered it…. What’s a little spanking between friends?

Now here’s where the fantasy starts-

I let him spank me, over the clothes of course. He’s estatic, and proposes a game. Being competitive, I oblige. If I can get through 10 spanks over the clothes followed by a count and then “thank you, sir” he’d send me 50$. However if HE won, he got to tie my wrists together behind my back. That’s all.

The only rules are that

1. If you mess up you have to start from the beginning.

2. Words have to be coherent and clear

3. Crying is an instant failure.

Easy. Easy money. Of course I’m all for it. He gropes my ass a little through my skirt and tights and proceeds to spank me. I don’t mess up but I laugh a little due to the awkwardness.

Then, he challenges me to round two. This time he pulls out a flogger and makes me flip my skirt up, so I’d barely have any protection. This time the prize is 65$ for 15 lashes. I’m feeling alright and the sting is nice and pleasant so I agree. The flogger catches me off guard and I mess up around number 7. As agreed, he binds my wrists together and ask if I want to try again. This time the prize for him winning is to fit me with a pair of nipple clamps. The thought of it did make my heart race a little. Knowing I was this depraved to let this man do this to me for money. Knowing the image of my red ass and clamped tits and lewd expressions were going to go straight to this man’s spank bank.

I smile and agree. This time I make it to 13 and fumble on my words. I was so close, I’m frustrated and pouting as he pulls my shirt down and gropes my tits. He fits them with nipple clamps and admired his handiwork before giving them a sharp tug. He asks if I’d like to play again, only this time the stakes are higher than ever.

If I can successfully complete ten lashes on my bare ass with a paddle, he’ll send me $120 and give me an ice pack- however if he won he gets to gag me and take pictures of me he can save for later.

I’m in a lot of pain at this point, but 10 lashes? It’s only ten, and I’m in this deep already. The punishment isn’t horrible either, he already jerks it to my Facebook pics.

He pulls down my tights and panties and sees how I’ve completely soaked through both. He slides a finger down my warm cunt and I shiver.

He takes his time with these ten lashes, it almost feels worse. Not knowing when he’s going to strike. He’s holding my bound wrists to my back and throws me an occasional “good girl” my way as I begin to shake. I make it to 9, and just before the tenth strike I start to cry. He tuts and tells me he’s sorry that I lost. He fits me with a ball gag and I feel so humiliated for loosing this much, letting it get this bad. Letting a total creep of a friend do this to me. He tells me he’s gonna tie my ankles together for the photos to get the full effect. I don’t really protest, I’m in this deep already. He pulls out his camera and snaps pictures of my tear stained face. My red ass. He spreads my pussy and ass, making me feel embarrassed and ashamed. Like a hunter showing off his prize game. Then he pulls out his leaking cock and positions of over my face. Snapping photos of him slapping me in the face with his cock. I recoil, since this was never part of the deal. His puts his balls on my face and rubs his precum into my skin. I try to move away but he just calls me a loser and forces me back. He roughs up my hair and what’s left of my makeup. “look at you. Never thought you’d stoop so low, huh?” He says mockingly. “I knew bitches like you weren’t so hard to break down. I know this is what your greedy fucking cunt wanted all along right? That’s why you’re so wet isn’t it?” I meet his cocky gaze with a scowl and a huff.

He begins to masturbate himself using the side of my face.

“C’mon. You can’t be that mad at me, right? I won fair and square. You trust me. I’ll take good care of you, that’s what friends are for aren’t they?”

He proceeds to bend me over again and slide himself inside of me and I struggle in my binds and panic. “Shhhhh, hey? Shhhh shhhhh. You fucking lost, okay. Now let me have what’s mine.”

bc gets a little messy.

His fingers brush my cunt.

‘It’s a lube dispenser.’

‘That’s right. And it’s doing such a good job’ he says, as he slides his cock into my asshole.

‘- and what’s this?’

‘My new pussy’ I whisper.

‘Good girl. You like Daddy stretching your little pussy?’ He mocks.