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Chapter 5
by
ChloBlo1218
How do you start the night?
Kaylie models her new lingerie
Taking longer than expected to return from her bedroom, my mind began to think about what positions I wanted to fuck Kaylie and what kind of toys she'd bought for us to play with. Of course I knew about the leather cuffs, but everything beyond that was a mystery. I prayed that she had purchased a butt plug, something deserved to be stuffed in her ass after repeatedly rejection my pleas for anal.
The distinct crinkle of paper bags and soft thumps of Kaylie's bare feet coming down the stairs caused me to turn around just as she entered the kitchen, understanding now what was taking so long. Kaylie hadn't just bought toys on her escapades to sex shops, she also bought lingerie and modeled it for me at the kitchen entrance. Her heavy tits caught my attention, completely visible in the lacy dark blue basque. The intricate floral embroidery hugged the bottom of Kaylie's breasts, leading my eyes to her dark brown nipples, hard-as-steel and about ready to break through the thin fabric.
Around her waist Kaylie was sporting a velvet suspender belt, thin lace triangles ending in a pair of clasps to hold up the matching fishnet stockings, sewn with elegant roses all the way throughout the material. The finishing touch to the ensemble was the tiny thong, doing little to cover Kaylie's pussy and even less to conceal her round ass. Rounding the final turn of her 360 degree presentation, I realized just how tight her panties were, pulled tight into her crotch and forming a cute cameltoe with her plump lips. The 19 year-old was wrapped in such a sexy package I wanted to tear it off of her and tie her up with it, but I knew Kaylie would kill me if I did since she just purchased the set today. I had to be delicate with the way I removed her lingerie, or I would be going home with the biggest set of blue balls I'd ever received.
When she was done giving her presentation, Kaylie waltzed over to me, placing her bags of toys on the counter and wrapping her arms around my neck, enveloping me into a long, deep kiss. "Me too. I was about to cum when I was trying it on, thinking about wearing it for you tonight. And if I could hold it, so can you." Kaylie rubbed her satin-covered cunt back and forth on the top of my cock, twisting in small circles when she touched the head, moaning lightly as tiny spurts of precum shot from my piss slit.
Remembering the main focus of tonight, Kaylie reluctantly parted her pussy from my cock so she could show me the collection she had amassed today. "As you know I bought a lot of things today and I intend to use them all at least once before I let you go home. But I was doing some thinking, and I want to try this one first." Turning back around and reaching into one of the three brown paper bags she brought down, Kaylie pulled out a small blue butt plug, matching the color of her luscious locks. The flared base was adorned with a fake blue gem, sparkling as it caught the light from overhead. It was thinner than most other butt plugs I'd seen, and the confused look on my face had caught Kaylie's attention when she turned to see my reaction. "What, you don't think it's big enough? You're lucky I like you, cause I also got this..."
Kaylie rummaged through the second brown bag and pulled out a standard sized anal plug, chromed out from top to bottom giving it a rainbow shine. "You have to earn this one, I'm new to having things shoved up my butt and I'm gonna need time adjusting to it. But believe me, by the end of the night..." Kaylie's voice trailed off as her mouth curled into a devious smile, knowing how much it turned me on when she teased me with assplay.
Do you insert the plug now or let her finish showing you the toys?
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Sexual Privilege
Freeuse for One
These branching stories are going to have 3 very simple premises: 1) You exist in a world where your character AND ONLY your character gets to have sex with whatever group or groups of people you choose wherever and whenever he or she desires. 2) The circumstances under which he or she can have sex with that group can be specified generally or specifically. 3) The response of the people you have sex with and/or the general public can be chosen.
Updated on Jun 11, 2026
by Cross C
Created on Aug 31, 2017
by SanctifiedVillified
You can customize this story. Simply enter the following details about the main characters.
With every decision at the end of a chapter your game state can change. Here are your current variables.
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