Poor Christopher. At 23-years-old he still lived with his mother. But she was away for the week, so he thought he would indulge his very secret cross-dressing fetish. He had kept it a very closely guarded secret ever since he was young. Anyway, as his mother was away, he decided to dress up in some secretly bought underwear he had purchased for this very week, and even a special collar and cuffs set and gag. He foolishly locked his wrists in the cuffs that were attached to the collar, confident he could get himself out of them. He was planning to spend an afternoon mincing around the house, and end the day with a long slow pillow hump. But his afternoon interruptedby the sould of car wheels pullingonto the gravel driveway. It was his Auntie Janice. And he knew she would just let herself in. He started panicking, but thought if the cuffs off he could run upstairs before she saw him and get changed. But all too predictably, he couldn't release himself. Instead of running upstairs to his room where he could take his time he remained in the living room, not thinking straight. Then to his horror she rounded the corner and entered the room.
Initially Janice was shocked and stood there in stunned silence with her hand to her mouth. Christopher just stood there like a rabbit in the headlights. On one hand it was a disaster for him, his shameful secret now exposed. On the other, it was a dream come true. He had long fantasized about being a sissy maid for his auntie, and even his mother, but the all too familiar shame of such naughty fantasies would always have him feeling bad about thinking such things, and what his auntie and mother would think of him if they knew. But when he saw her hand lower from her mouth, and saw the growing smirk on her lips he instantly felt an electric jolt of excitement flash through him. And almost instantly, he was erect again. She laughed as she noticed his embarrassingly small 'manhood' barley stretched his knickers. She circled around him like she was circling prey, until finally she spoke. 'Well, well, well. Did I interrupt something?' She said, her voice dripping mocking glee.
'Mmmmph' was all Christopher could manage from behind his gag. Causing more laughter from Janice.
'Tell me, does your mum know about your little hobby?' She asked with a beaming smile. Christopher slowly shook his head.
She giggled and said, 'I didn't think so'. She paused for a second then took out her phone. 'Why don't we change that?' She laughed, then started taking pictures of him, lots of pictures. She spent an inordinate amount of time taking photos after photo, from angles, and close ups of his excited clitty underneath his knickers. Christopher moaned his desperate pleas for her to stop through his gag, which she simply laughed at and teased him further by saying, 'Awww, I'm nearly done sweetie, just a few more'.
After drawing out every bit of humiliation she could from the pictures, Janice moved in close to Christopher, who although was still moaning his pleas through the gag, but at the same time was maddeningly aroused, and was on the verge of squirting his cream in knickers. As she brushed up beside him he looked down at her phone, and to his utter despair she was on the messenger app and was uploading photos ready to send. She then started typing and cheerfully read aloud what she'd written, 'Hey sis, I found Christopher indulging in a little hobby I think you'd be interested in. The poor thing is all a fluster, and I think he is about to have a little accident if he's not careful. What do think I should do? Love Jan'. Christopher was now shaking his head desperately now, trying in vain to get her stop, and desperately hoping she was just teasing him. But of course, she wasn't. And with the most soul crushing of little grins, she held up her phone and so very slowly tapped the send button. This time it was a horrified squeal that Christopher produced from behind his gag, to the absolute delight of Janice, who clapped with glee as real tears of frustration and humiliation ran down his cheeks.
Janice then turned her attention to his less than impressive erection. She moved to the side of of hom and and looked down at slightly stretched knickers, and asked, amid many giggles, 'tell me darling, have you ever been with a woman. Come on be honest'. Christopher looked down and slowly shook his head. Although he had a very strong cross-dressing and sissy fetish, he still held paradoxical strong male desires and hated his underwhelming organ. She laughed as he shook his head in answer to her embarrassing question, and replied amidst many giggles, 'It's probably for the best sweetheart, I mean, we'll, I'm sorry Christopher, it's pathetic!'. She almost fell over laughing, and by this point Christopher was just standing there absorbing the humiliation like a sponge, and trying to process his genuine anger at his auntie's non-stop and very successful attempts at humiliating him. But at the same time he'd never been turned on, and dangerously close now to a full orgasm into his sensual satin knickers. She knew that too, as she could see the spot of pre-cum coming through the glossy surface. And slowly she started moving her hand to his now desperate clitty.
He screamed a muffled 'no please' through his gag, but she simply giggled as her fingers gently touched his panties and through them his stiff little sausage. He was squealing and shaking his head, trying to get her to stop. But it was futile. She had the bit between her teeth, so to speak, and was determined to humiliate him as much as was possible. She ever so gently stroked his peenie through the smooth satin and said in sweet toned whisper, 'what's the matter sweetheart, don't you like your auntie stroking your cocklette?'.
But this was her misunderstanding, she thought he was so desperate for to stop humiliating him as she was his auntie, what she didn't understand was just how close he was to spurting his cream. She had seen how aroused he was and ashamed he was, and was just starting to question to herself how far she had taken things and was just about to stop her cruel teasing of his clitty. It was then it happened. After only 30 seconds or so of her gently stroking and tickling his lollipop, he stated bucking and spasming and all of a sudden she felt the warmth of his cream the the satin. Jet after jet until it started seeping through the satin and dripping from her hand. She could only look in shock at his sissy juice, now dripping onto the floor.
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