Sissy Shopping Stories

44,561 results
Orientation
Length
Source
Infinite Scroll

Preoccupied

by jouet on Sep 17, 2017
BDSM

The smell of autumn was in the air, as the gentle breeze kissed my cheeks. Strolling through the farmer's market on an early Saturday morning, the sun was just starting to emerge. The rays of light dancing around me, I couldn't think of a better place I'd rather be. Strong, fresh brewed coffee in hand, I passed the vendors, who were still putting out the new...

New Suit

by DaveAgarmanStond on Sep 2, 2017
Erotic Couplings

I'm standing in my walk-in closet wearing just my boxer briefs staring at my clothes. All neatly organized and arranged, but today they seem to be unappetizing. I feel I need something fresh something new, something that suites my mood. I throw on a pair of my favorite jeans and a nice shirt, I am going to go shopping for a new suite and I know just the plac...

Fun in Blue Ch. 1

by bhambabygirl on Sep 16, 2017
Interracial Love

"Great, just fucking great!" I thought as I pulled to the side of the road in recognition of the blue lights behind me. The last thing I needed right now was a fucking ticket. After the third 12-hour day this week, all I wanted to do was get home and rest before the one tomorrow. I couldn't tell you how fast I was going because I was too busy masturbating to...

The Good Will Goddess

by freakofnurture on Sep 16, 2017
Mature

I dig through an anemic assortment of cassettes, hoping vaguely for a Neil Young or Leonard Cohen gem. Good Will shopping is like any garage sale; fishing in shit for a priceless prize. "Can I squeeze in?" asks a woman in her mid-to-late forties, smiling widely. "Sure," I say, sounding apologetic and moving an inch or two to the side. "I have one of thes...

One Fine Massage Ch. 5

by magichands on Sep 16, 2017
Exhibitionist & Voyeur

Please see my earlier stories to help make sense of this one. * * * * * After I finished my massage session with Lynn, I left her to relax on the massage table, and collect her thoughts. As I stepped out into the living room, my wife Lee smiled up at me, I saw the look in her eyes, she has obviously heard Lynn in the throes of her orgasm. Lee is a fine w...

My Grandchild Ch. 04

by Joseki Ko on Sep 16, 2017
Novels and Novellas

When I was all cried out Gram gave me a little pat on the head and finished getting ready. I sat on the couch with my back straight and my hands folded together. I had to admit this was an effective approach with me. I had never felt so humiliated or out of control in my entire life. I was also really dreading the trip to the mall. Buying, clothes or shoes,...

The Orgasmatron

by mrsdozer on Sep 13, 2017
Toys & Masturbation

My Husband was surfing porn on the Internet, and came across a site that had homemade Fucking Machines. It was really wild. Women were getting fucked with dildos that were attached to all kinds of contraptions. Being the inventive person that he is, he decided to build a Fucking Machine for me. During the process of building it, he stopped to contemplate wha...

Dead Battery Ch. 02

by MungoParkIII on Aug 29, 2017
Humor & Satire

  After jumping the battery for the stranded lady in her Beemer, Dan started heading home but was unable to ignore the image of the woman running that wand thing up and down her pussy in the strange purple glow. The way she reacted to that thing was something Dan had never seen before. Yeah, he had been married a while, but in their day he and his wife...

Her Stud Lover

by Bad2Bone on Sep 17, 2017
Loving Wives

This is a true story. It demonstrates how much I have grown to appreciate her flexibility in responding to my kinkier side in our lovemaking. There are times when she truly amazes me with how I get her to agree to some of this stuff. Well, here's one of those times, so read and enjoy. (I sure did!) My wife (Jill) seems willing to please and has given me so...

A Little Bit Looser Now Ch. 2

by Gonzo099 on Sep 15, 2017
Loving Wives

Its been a few months since Jim's last visit, and Hellen has decided to tone down her new persona. She stopped wearing clothes that were too revealing, but enough to get other men's attention on the street, she toned down her flirting with other people and out public sex acts were limited to a blowjob in the theater and in public bathrooms. Jim was coming b...