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Found 1,072 results on 494 sites by 494 authors for rubber sissy, page 5
Bright
 
Confessions
February 26, 2011 - 11,600 words

The twins hated church for the same reason Sissy loved it. · I waited for Sissy to emerge from the shower so I could yank her towel and see if she had grown anymore cunt hairs since I last yanked her towel. Looked the same but her tits seemed to have grown bigger in one day. I offered the twins a buck apiece to suck my dick. · After the first confession, Jeff, John, and I saw a full frontal when she came into the kitchen looking for a rubber band for her hair as we ate breakfast. · You would think the rubber band could wait, though we were glad it couldn't. What a sexy pussy. I became a big fan of bald pussy that day. Sissy would look great with a bald pussy. ·

By: Phil Phantom
The Ba (part 1)See all parts
December 20, 1994 - 15,000 words

She would say things to me like, "Little boys who wet their pants need to wear diapers and panties." I was wearing the diapers at night and on weekends, but she also insisted that since I was such a sissy, that I should wear panties of her choice, when I wasn't diapered. This threw me a little, I was always into diapers, but women's panties, never really entered into my mind much. · I got out of bed, and headed out towards the bathroom, I was getting aroused by the feeling of the diapers and the noise the rubber pants were making. I just turned down the hall when I heard Judy calling me. "Oh diaper boy's awake. Come here honey", I turned and headed towards the kitchen. ·

By: adietrech@aol.com
The Nerd Bisexual
July 1, 2005 - 4,100 words

He had caught him peeking at his sister Sissy one evening as she dried off after her shower,he was pumping his cock like mad as his eyes remained glued to her naked body. Toni was thirteen at the time and his sister was was almost eleven with the a sexy little body. · Toni and Sissy had went in to change and as he stood naked in the bedroom Sissy had went in to shower.He watched as his dad walked by and stood at the bathroom door removing his trunks,his big cock hard and still,then went inside where Sissy was putting a rubber band in her hair. He heard her gasp as she said,"daddy!" If his dad said anything he was not able to hear what it was before the ·

By: Ham Barker
The Debutante Maid
March 29, 2009 - 4,400 words

Taking one last swallow, the guest entered, walking into the foyer as his host closed the door, shutting out the outside world with a soft but final sound of wood and rubber. "Put your bag down and stand there," he ordered, forgoing the pleasantries in a way that set the tone immediately. · The sissy put his hands back down. He grabbed the shirt and raised it above his head and off. · "Very nice." The sissy stood there, completely on display, knees trembling form the unfamiliarity of it all. "You are a real sissy aren't you." "Sir," he nearly whispered, "yes Sir." "Nice bra. Where'd you get it? "Sir, it was my ex-girlfriend's, Sir. ·

By: Maid Rebekka
 
Master's Sissy Ba
December 27, 2011 - 4,200 words

Master's Sissy Baby Boi Provided By: BDSM Library www.bdsmlibrary.com Synopsis: A man enslaves another man into a baby slave to live along with his other male · He picked me up and laid me on the table, placing a new diaper on me. He covered this with pink rubber panties and frilly pink satin panties. He dressed me in a red skipper dress with a huge white square collar that had roses on each corner. · 15 long minutes later, he came inside me, then he unleashed a gusher of piss in side me. Then he diapered me and put rubber panties on me. We lay in bed and he frequently kissed me, telling me I was His forever. We fell asleep with me in his arms. In the afternoon, a taxi ·

By: Verna Benson
Darla (part 5)See all parts
June 18, 2010 - 3,300 words

It was quite erotic to see them gobbling up the rubber cock and wiggling and grunting on the floor until they were "bumping muffs", as Mrs. Peterson, sissy Betty's mother, so cutely said. When the rubber cocks were entirely inserted into sissy pussy Mrs. Peterson had each girl slowly pull off the dildo to see who had done the better job of cock gobbling! Since the dildoes were a good 2 feet long it's safe to say that some of those sissies are really talented! The owner of the local sex shop, Lefty as he wanted ·

By: Victoria
Sons Into Daughters (part 2)See all parts
October 18, 2008 - 12,800 words -

As they are forced, on pain of a further intervention from the crop to slip their long, silky smooth legs into the tight, surprisingly soft pink rubber panties, a feeling of undeniable and deeply feminine pleasure grips their sissy bodies and their rubber imprisoned cocks twitch with excitement. This strange arousal is made much worse once the long, tight panty girdle · So Chrissy stares at Prissy, at this rather lovely vision now sealed from chest to ankles in pink rubber, this pretty, sexy sissy doll and feels his sex, so effectively imprisoned, fight a little harder against its restraint. Briefly he remembers writhing in the playpen and struggling in the cot, of the ·

By: ChristinaShelly
Tags: crossdressing, erotic, erotic encounters, taboo
Kissing Kousins (part 1)See all parts
January 3, 2004 - 5,600 words

I was now made to don a pair of pink rubber pants. · It's a good thing that I was such a skinny little shit; my bony ass, which was upholstered with the diaper and rubber pants just fit into the seat. The tray was fastened around me, thus securing my arms snuggly in the · "If you don't, we'll show the pictures to everybody, and they'll see what a big sissy baby you turned into. · If you're not good, we'll take off your pants and diaper, and spank your naked bottom right here on the street in front of everyone and they'll see your little dick hanging down between the legs of the little sissy baby!" I stopped talking and sassing the girls for the rest of the walk around th ·

By: Wendi
 
Dani's Story (part 4)See all parts
December 7, 2008 - 8,800 words -

Next to him was a beautiful frilly sissy named Daphne. She wore the puffiest, frilliest dress I had ever seen. Her petticoats formed a virtual sea of frills and lace about her. · She was just the perfect sissy sitting dutifully next to her Lord and Master ; a picture of pure sissy contentment and acceptance of her position. She must have been one of the "blurs" in the receiving line when things were just moving too rapidly for me to fully appreciate. · A small wire and rubber tube ending in a small palm pump extended from each wimp's bum. The wire attached to a little box, similar to the one used for my tittie treatments. "Was that an inflatable plug?" I wondered. ·

By: Sissystevie
Tags: crossdressing, erotic, erotic encounters
A Look Into My Mind: Uncle Sissyboy (part 4)See all parts
March 13, 2011 - 3,700 words

"Oh no you don't uncle sissy boy!" shouted my sister in law, Arlene. She rammed a strap-on up my ass in one hard shove. · "What's with the rubber panties, sissboy?" asked Arlene "Mistress, I was really beginning to smell, so I figured this would solve some of the odor problems. · Lauren entered the room and she was dressed in a Domme's outfit of black rubber. She had a short black rubber skirt, black rubber top and very high heeled black patent leather shoes. Her hair was pulled back into a pony tail. · Take them out, panty sissy uncle" barked Lauren. I did as I was ordered, standing in front of the two of them with my shrinking limp clittie. Lauren and Arlene walked aroun ·

By: Unknown