Disable your Ad Blocker! Thanks :)
Chapter 105
by
Sinburn
What's next?
Office fun
The following morning an enthusiastic Tilly burst into Tom's bedroom. "I want you to wear women's panties today" she announced throwing herself onto the bed "I brought you a few pairs to pick from."
"What?" said Tom a bit disorientated from just waking up and then after processing what she had said "Ugh, Tilly, no. It was kind of kinky fun last night but I'd rather just wear my own clothes."
Tilly pouted "I was worried you'd say that Mr no fun. How about this?" She crawled into bed with him and pressed herself against him "If you wear the panties I'll let you lick my pussy" she said with her face close to his.
"I'm not sure how much that benefits me" said Tom getting excited by the close proximity of the beautiful young woman.
Tilly smiled softly her eyes exploring his face as she snaked her hand over his body "It benefits you because you love licking my pussy and having access to my body. I'm talking completely nude and you can touch me wherever you like." She kissed him and her tongue darted into his mouth "You want to pleasure me, don't you?"
She had him. He lusted after Tilly hard and he had a massive crush on her. The idea of spending any sexual time with her was always a draw and all he had to do was wear some panties "Okay" he relented."
Tilly leapt out of bed "Yes! Go and have a shower and shave I'll lay out your clothes." She danced out of the room humming to herself.
He did as he was told. He couldn't find his usual shower gel so just used the one that was there which was flowery but he didn't much care, he would just have to buy some more. Tilly bust in carrying a cup of coffee "Come on I'm waiting. I'll leave this here" she said and disappeared back to the master bedroom.
He drank the coffee and finished his morning routine before wandering into the master bedroom nude. He had lost any sense of shame with Tilly now, she had seen him nude so many times and in many more embarrassing positions. He halted when he saw what was on the bed "I thought it was just going to be panties?" On the bed was a white blouse, a skirt and a full set of lingerie including bra, stockings and suspender belt. He was about to walk back out when he caught sight of Tilly in a similar but much naughtier version of the outfit she had laid out.
She saw him staring and did a little spin "I thought I could be your personal assistant today. I'll help you out with all your work and if a little sexual harassment happens to occur then I'm okay with that." Images of office fantasies flooded Tom's imagination and he figured a little cross dressing would be worth it.
Tilly helped him into the underwear and they found a suitable padding for the bra which, whilst being one of Sarah's older ones still gave him an ample chest. Before they put on the rest Tilly sat him down and applied a layer of slightly too thick to be professional makeup and then got him into the blouse and skirt. It was a good thing that Sarah had been tall or he wouldn't have stood a chance of fitting in anything and even now they didn't fit comfortably and the skirt couldn't be fastened all the way. Tilly admired her handiwork and agreed that he looked like an incompetent cross dresser but declared that it would do and they got on with the day.
Tilly was actually pretty helpful in the office and he got her to do many of the more menial jobs he'd been meaning to get to like reorganising the filing cabinet. However when she had mentioned sexual harassment he had assumed she would be the one getting harassed. He certainly got a couple of firm pats on her behind during the day but more often than not he was the one getting groped or commented on. "Mmm baby, I love the way you wiggle" she'd call or "Look at those dick sucking lips. I bet you could suck a golf ball through a hosepipe." They were pretty funny but Tom couldn't help but feel a little humiliated. Even so he played along. Tilly had such a bright enthusiasm it was hard not to get swept into her game.
By the end of the work day Tilly was so eager to get Tom in bed she pulled him into the bedroom and started stripping off "Lick my pussy bitch." she said as she pushed Tom's head against her dripping snatch. Tom willingly obliged and indulged in running his hands over her body as he lapped at her. Tilly insisted on several orgasms before she let him go. She threw on a gown and told Tom to strip to his underwear. He had been hoping for a little stimulation but instead she announced that she was hungry and wanted to watch Tom cook.
He was mortified. The kitchen window looked out into the front garden and while it was extremely unlikely that anyone would look in at the few moments he was stood in the right position to be seen he made sure he spent as little time as possible visible. The rest of the night he stayed in the lingerie at Tilly's insistence and at bed time she used her body to tempt him into a comfortable pair of cotton panties and a girly, strappy top to sleep in.
Tom lay in bed that night. He was desperately aroused, Tilly had been teasing him all day and never given him the relief he craved. In desperation he tried to finger himself but couldn't get the angle right and just got more worked up. He felt like going in and asking her to help but she would be asleep by now and he didn't want to make her mad by waking her up. Eventually sleep took him as he fondled his sexless crotch.
What's next?
Disable your Ad Blocker! Thanks :)
Wishes for my Wife
A tale of transformation
A man receives a wishing coin but can only make wishes that affect his wife.
Updated on May 17, 2026
by Sinburn
Created on May 17, 2019
by Sinburn
You can customize this story. Simply enter the following details about the main characters.
- 39,694 Likes
- 16,074,625 Views
- 4,192 Favorites
- 6,829 Bookmarks
- 1,195 Chapters
- 125 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments