Sissy Shopping Stories

44,561 results
Orientation
Length
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Infinite Scroll

Lily Ch. 01

by EliasRotica on Aug 31, 2017
Fetish

I started seriously traveling for business several years ago. After you get the Platinum status and free upgrades to first class, you realize you're spending a lot of time away from home. I also realized that I felt like my time away from home was like a second life... I had different friends, ate different places, did different things. I also began to indu...

Punishing My Tits Ch. 03

by RedHawke on Sep 14, 2017
Fetish

*NOTE* For maximum enjoyment, read chapters 1 and 2 first! All through the next day, I pretty much stayed wet, remembering the varied pleasures of the night before. I had a hard time paying attention to anything in front of me, remembering instead the pretty pink welts left by the clothespins on the soft, pale skin of my large tits, and the sensation of my...

Online Lover

by JJ on Sep 13, 2017
Erotic Couplings

I went shopping today. I thought about finally seeing you, and I walked into the Victoria's Secret store. They have this pretty new bra called "Desire". Apt name I think... since I wanted to wear it for you. It's lace, and low cut, and when I tried it on, it cupped my breasts like I imagine your hands will. Thank goodness it comes with thongs. Did I ever tel...

Taylor-Made for This

by TheRealSixGod on Sep 19, 2017
Celebrities & Fan Fiction

I found my way backstage at a Taylor Swift concert. No, I didn't go and listen to the music. I snuck in. I just had to do something. I had this whole elaborate plan where I got past security and somehow it worked out perfectly. I knocked on her door and she was alone, just chilling out with headphones in after taking a shower, getting her bags ready. She w...

Wardrobe Disagreement

by MissSusanAnn on Oct 15, 2017
Exhibitionist & Voyeur

To begin, this is a true story, so yes it really happened. That said, the names, locations and dates have been changed. A little information to get started, I was raised in Bangor Washington. I am 38 years old at the time, 5 feet 4 inches tall, I have large breasts for my size, and I am fairly athletic. A devout christian, I lived with a loving set of parent...

The Perfect Butt Plug

by TheBiProf on Feb 6, 2018
Anal

Walking through the aisles of the grocery store I must have a grin on my facing knowing I have a secret that no one could possibly guess. I pass all of the mothers doing their weekly shopping and I just want to stop one and tell her, "I have finally found the perfect butt plug and I'm wearing it right now!" I've always read that butt plugs give you a great...

The Dressing Room

by NikkiTrakz on Aug 19, 2017
Exhibitionist & Voyeur

I've dropped one dress size and none of my clothes fit so today I'm doing a little shopping. You've agreed to come along so I better make it worth your while. I can't wait to show off my new body as well as live out a reoccurring fantasy of mine. Our first stop is picking out new bras and panties. I've selected four bras and ten pairs of panties to try on f...

Down the Gangplank

by naked4all on Sep 17, 2017
BDSM

3hole stood naked, humiliated and horny at the top of the gangplank. Her hands were still bound behind her. Her mouth hole had been uncovered and a ball gag inserted. She could see the crowd gawking and nudging each other, pointing and taking pictures. Many were giggling. She saw who might be the wives lined up to the left looking grim. The training butt plu...

As You Wish, My Mistress

by GreaserBob on Sep 13, 2017
BDSM

This is the voice of your Mistress. Can you hear me? My words are in your eyes and in your vision, in your head. You are so in my control that I really am there, aren't I? In truth, if I'm in your head, then I'm about as present as I can possibly be. You are going to demonstrate that in two ways: First, by doing whatever I command you to do for the next few...

A Boy's First Time

by yourslavegirl on Sep 14, 2017
Erotic Couplings

He and I had been best friends since senior year of high school. I'd had a crush on him since we'd met then, and still had it even after he came out to me. Since we were both in college, we couldn't see each other as often as we would have liked to, but we got together as often as possible during winter and summer breaks. One winter break, about a week afte...