Jack Gets More into Kink with Terry

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"I'm thinking of calling it Strawberry Crudescence," Terry declared. "Please take a sip and give me your assessment."

My mind was reeling. Was I going to ingest something so repulsive--products of every bodily function--or would I set some boundaries with Terry now, no matter how fond of her I was becoming?

I figured I could deal with the pee and Terry's menses. I took a sip, carefully avoiding the "chocolate" and hoping that it hadn't flaked off into the liquid.

The sip was enough to convince me that I'd taste no more of it. I figured I hadn't had enough of it to get me seriously sick.

I smiled at Terry and moved to give her a kiss. She pulled back.

"Oh," I said, "so it's too much for you to sip, eh?"

I don't think she was used to being challenged like I just had done. Indeed, I didn't know anything much about her boyfriend or anyone else she may have dated. It seemed that this had shaken her up. She wasn't used to it, I guess.

She started to cry. "I'm sorry, Jack," she said in a voice broken by her cries, "I went too far. You don't hate me, do you?"

It was amazing to see how this had changed everything between us. Until now, I had been ruminating about how to deal with a dominatrix. Now I saw that she had another side to her.

I took her in my arms, not kissing her, but holding her tight. "I'm so fond of you, Terry," I whispered into her ear, "and this confirms my feelings. But you have been a naughty girl. And you know what happens to naughty girls, don't you?"

"They get spanked," she recited in a blank tone of submission, or maybe it was just love, and not wanting to lose me.

"You're right," I replied. "Before that happens, though, you're going to stick a tampon in your puss."

This seemed to awaken her sense of humor. "Wow, Jack, I never thought you'd be telling me to do that," she giggled as she reached into her nightstand and took out a wrapped Tampax Slender Regular." She unwrapped the tampon and handed it to me!

"All right," she smiled, "I'd like you to perform the insertion."

She sat on the towels at the edge of the bed again and handed me a tissue. I wiped her pussy and saw the red on it. Then I took the tampon and put it right at the opening of her pussy, pushed it into her and then pressed the applicator to push it into the right place in her vadge.

She was stupefied that I knew how to do something that was so totally feminine.

"Thank you, Mr. Jack," she said very respectfully. I think she was more impressed with my knowing how to do what I did than with my calling her on her refusing to drink her vile concoction.

"I'm ready for my spanking now, Sir," she immediately announced to me.

I sat on the chair, and she dutifully clambered across my lap. She was naked but entirely unashamed, maybe because she had a truly fine body.

I rubbed her bottom cheeks a bit, figured I'd better stay away from teasing her pussy, but couldn't resist finding her asshole with my finger and slowly and gently pressing my finger inside her most private hole.

Terry gasped as my finger probed her rectum. I didn't feel anything in there, but she said, in an embarrassed way, "Jack, it would be better for you if you don't probe in that hole. When I get my period, my movements can become very soft. If one is on its way--and I don't feel anything now--you would not want to have your finger in there. It could get messy."

I could see that she was embarrassed enough just by telling me all that, but since she didn't try to make me stop, I removed my finger anyway out of caution even though I figured her overall horniness and the elevated sensitivity brought on by her period meant that she enjoyed this probing. She was just worried that my finger would emerge covered with her soft shit.

I decided I'd teased, or rather, turned her on enough and began spanking her bottom. I showed her I could spank as well as she could. I started slowly and then picked up the pace. She started to moan and then groan. I moved down into the crease between her bottom and her thigh. I knew this was a very sensitive spot and she began to whimper. She was trying not to plead for mercy.

I gave her a few spanks on her lovely thighs and ended with one on each inner thigh, which I knew she wouldn't like.

Then I told her that she had taken her spanking like a good girl and that she was forgiven.

She stood up and leaned into me for a hug. And then she kissed me.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
HottieOlwenHottieOlwen7 months ago

I find any story that involves toilet training very arousing, and this one is no exception. I loved it. 5 stars.

Share this Story

Similar Stories

Our Piss Orgy Pt. 01 It was time to share our piss play with another couple.in Fetish
All Day Piss Session We made a deal to try to swallow all piss that day.in Fetish
A Rimming for Rachel He describes his first time performing analingus.in Anal
Sis Piss Ch. 01 Three sisters make their younger brother drink their piss.in Fetish
The Taste of Ass An appreciation of a woman's most intimate flavor.in Anal
More Stories