Sissy Jess, Cuckolded by Mum Pt. 01

This is a short story about Jess. Jess is a sissy who likes to dress in her Mum's clothes. Things go along well until until Jess's Mum, Evelyn, hires a man to do some work in the garden. The man turns out to be Curtis......

"Jess, Jess, I need you to help me carry in the shopping."

Jess groaned and guiltily he wished his mum would get someone else to help. He just wanted to look at all the other sissy girls on Twitter and get his little "excitement" hard. He grudgingly went downstairs and helped his Mum. It was the least he could do as he had been dressing in her clothes for the last six months or so. Taking pictures of himself and posting them on his Twitter account. He was embarrassed that he had even stolen one of her lipsticks and used it on his lips and nipples, and to write things on his girly belly, hardly the thing for a twenty three year old man to be doing but there it was.

When they had finished she said "Now Jess I need you to mow the grass, and take off that heavy jumper, it's too warm to be wearing that."

"Muuuuum."

But he really wanted to hide his chest. His "sissy titties" as his Twitter followers called them. Whenever he got a chance he would borrow one of Evelyn's lacy bras and then he would oil up his "titties" putting lipstick on the nipples and pose for the camera. His Mum had a lot of nice clothes and really beautiful underwear, despite his feelings of guilt he returned to her wardrobe again and again, posing in her dresses and sending pictures to the internet.

He got the lawnmower out of the shed and started cutting the grass. His Mum was right and soon he had to shed his heavy jumper. He caught sight of his neighbour George watching him from over the fence. 'Blast it." He thought.

George was an old perv. Always watching Jess when he was in the garden, ogling his chest. Once when Evelyn had send him around to help George pick his apples he had pounced on Jess. Grabbing his ample chest with one hand and trying to kiss him. Jess had to use all his strength to fight him off. Still the thought of old George finally cornering him and using his superior manly strength brought out strange feelings in Jess.

His Mum brought him out a cold drink when he was about half way through his work and he stood for a break. She took out the garden hose and started altering her plants and flowers. When his back was to he she turned the hose full on him.

"That will cool you down a bit Jess." She said laughing.

The white tee shirt clung to him as he could see George out of the corner of his eye watching on. Finally he finished the grass and crept into the house before his Mum gave him other chores. She banged on the door of the shower telling him to hurry up. Ten minutes later she came into his room with a red dress in her hands asking for his help to dress. She had a matching set of lingerie, red half cup bra and full cut panties, red corselette with suspenders attached to red fishnet stockings. Any other red blooded son would have been excited to SEE her, but Jess just wanted to BE her. He fastened her into the dress as she swept out of the room in a cloud of perfume. She said something about meeting the girls, but Jess thought that she might be having an affair. His Dad worked away a lot and he knew their sex life was not what it should be. The sounds of their lovemaking, which had woken him on weekend nights had stopped over two years ago.

"Still," he thought, "it's an ill wind," scurrying off to find her still moist panties and select an outfit for the evenings dressing show on the internet.

He selected an outfit to mimic his Mum's going out clothes but in black not red. He dressed in her still warm black panties, pulling a pair of sheer tights on over them carefully. He put two crosses of electrical tape on over his nipples, this was a new fetish he had recently turned onto, sometimes he even slept with them taped up. It made him so horny, and judging by activity in his profile he was not alone. He then wrote his unique call sign on his girly belly and started taking pictures, slowly removing his Mum's clothes as he went. The photo session went well and he made little sissy cummies twice. He was careful to hang her dress in her wardrobe and put all the other clothes in the washing machine on a gentle wash, leaving her a note saying he had put on a wash and would dry and put away in the morning.

He was fast asleep dressed in his own girly boy shorts with his nipples still taped when she burst into his bedroom, telling him drunkenly to help her undress. He unzipped and removed her dress, unclasped her corsellette and stockings. Removed her bra letting her heavy breasts sag slightly and finally skinned her panties down her sweet thighs. She mumbled about getting a nightie for her and no sooner had he put it on her. She was fast asleep, her drunken breath starting to fill the room. He couldn't resist putting her panties to his face inhaling her scent and that of what he was sure was male cumjuice. He lay down beside her, feeling her leg drape over him as she pulled him into a warm drunken embrace.

He barely heard her say,

"Love the panties and the tittie tape Jess, oh and I met a friend of yours tonight. He is coming over to do some work for me next Saturday."

But before he got an answer to his questions she was fast asleep again.

Thank you for the courtesy of reading this. If you have any comments or questions please leave your welcome feedback.