Sissified by My Mother-in-Law:
Humiliation, Deflowering, and Feminization for the Sissy Girl

by J.S. Lee

Copyright © 2018. All rights reserved.

 

This is a work of fiction. All characters are 18 or older. No characters are related by blood.

 

Smashwords Edition

Chapter 1

 

David hadn't had any alone time lately, not since she had moved in. His mother-in-law, Helen, or Mount Saint Helens as David referred to her in his head and never out loud, had taken over, just as David had warned his wife that she would.

 

Helen had asked to move in but as usual, it wasn't really asking. She had decided that it would be the best thing for all of them and before Christie had a chance to tell her step-mother no, she had arrived on the doorstep. David had kept his opinion to himself, as he did with almost everything else that happened recently around the house. Christie seemed to be enough of a wreck without starting a fight but if he had dared, he could have told her that Helen would ruin everything.

 

Of course, David had his own private thoughts about Helen that made the whole thing much worse and if he had started down the road toward confession, there was no telling where it all might lead. That was what he told himself anyway, after closing the bedroom door and taking a deep breath. If he started telling Christie his secrets, he was afraid that something inside him would just click and it would all spill out, uncontrollably.

 

He had at least thirty minutes to himself, the kids would storm through the house then along with his wife and then the whole, predictable process of the evening would commence and David had a need that he couldn't deny another moment, let alone a whole night. When he had spied his mother-in-law's red, satin and lace panties and the matching bra on the top of the pile of laundry, David felt the temperature rise around him. His body quivered and flushed, the sudden heat inside was a flame and his fingers twitched to get at them. He had waited like a predator, slinking down in the shadow, every muscle tensed, ready to spring. David had gone for this long without casting any suspicion, he wouldn't get caught now.

 

When all of their eyes were on the television, he had stolen her red underwear and in his mind, he told himself that they were whore panties, sufficiently slutty for all of the dirty daydreams that played out in his head and absolutely no where else.

 

He had hidden them in his drawer and now, alone in his bedroom, half undressed already, he was more than ready. David's cock was knocking in his boy underwear, straining for the touch of the slinky panties on his shaft, the intoxicating feel of the material, so smooth and cool on his body. It had been so long, far too long since he'd put on panties and David could swear that it had become a physical need.

 

Feet through the holes, he gently guided the satin material up his bare legs. The feel of it, brushing his body on the way to his hips, made every hair stand at attention. This was exactly what he had been aching for and once the panties were in place, it was almost as if they had been meant for him. The satin hugged his body and his manhood was thumping at the front of the lacy crotch. All that was needed now was the bra, the lace rubbing against David's hard, swollen nipples was an exquisite torture that made him moan when he thought about it. The touch of women's underwear, the smell of it, the silk on his fingers, rubbing the lace on his face, it had all been tantalizing from the very beginning.

 

David knew that this wasn't all there was to it though and his cheeks burned once the bra was hooked into place. The underwire dug into his chest and the cups were too large, considering that he had no real breasts, but his nipples responded and fluttered when he pressed the fabric against the pink tips. One or two tugs at the right moment and he would burst all over in creamy waves.

 

Even without the stolen, red whore underwear, thinking of Helen did that to David.

 

He'd never wanted it to be this way and when he met Christie, he swore that he was the luckiest man in the world to get a date and then a second and so it went until he proposed. David only had eyes for her and it wasn't until the week of the wedding that he crossed paths with Mount Saint Helens and he felt the ground rumble beneath his feet.

 

She was a siren, she should have been a goddess on the silver screen. Helen still commanded every man's gaze when she entered a room and she must have known that her son-in-law would follow suit. Christie swore that her platinum hair came from a bottle and David didn't care. If he closed one eye, her walk, her shimmy was more like it, Helen looked like Marilyn Monroe and the thought traveled straight to his crotch. It was almost as if her hand were there, opening his zipper and reaching inside. His mother-in-law's red nails trailing along his sensitive skin, he lost all control once she came into view.

 

Unfortunately, the fact that Helen was an awful bitch made absolutely no difference. Sometimes David thought that the fact that she was such a slave driver and regarded him as something not quite human made it even more tempting. Whatever she thought of him, David was obsessed with her. He bit his bottom lip as he stared at his reflection in the mirror, the red underwear that had graced her perfect curves, now wrapped around his body. When was the last time that he had thought of Christie when he had an erection? David couldn't remember but he knew precisely the last time that he'd masturbated to Helen.

 

It had been this morning, in the shower.

 

Now, not quite ten hours later, his cock wiggled in the front of the red underwear and he wet the fabric with precum and began to rub his hand up and down, over the whore panties. It was divine, the feel of her panties on him. He had always liked to cross dress in secret, but this was much worse. David had a crush on his wife's mother, if Christie knew that, he was sure that she would leave him and rightfully so. If she knew about the panties and how he had rooted his face in the crotch, disappointed that there wasn't a trace of Helen's scent left in the clean material, David didn't have to guess.

 

He'd lose her for good and it wouldn't really come as a surprise. David stroked himself with two fingers through the panties, pressing the liquid and the satin against the back of his aching dick, how could a panty-wearing faggot like him keep a wife anyway?

 

David groaned and spilled a hot droplet of his need into the panties again. They would be soaked through before he was done and with his left hand he pinched his nipple, grinding the lace into his body, it hurt and he couldn't get enough. If Helen knew, that would be even worse. Helen, the woman who would burn through his life, given the chance... and if she had any idea that he was a pansy on top of all his other failures. David shuddered and whispered her name, his mother-in-law would make him pay for his sins but for some sick, twisted reason, he couldn't wait for her to dole out his penance.

 

David thrust his hips forward and squeezed his cock, just under the head, tugging his nipple at the same time, just a bit, he wanted to make it last but the thought of the blonde's delectable pussy in these panties was too much to hold back. His mouth was open, his tongue was out, the pleasure coursed through his body and he said her name again, just above a whisper. "Helen, oh Jesus Christ, yes, Helen," he had never fucked her in his imagination, he couldn't even dream of being allowed.

 

It was Helen's voice that made him scream and he hoped that it was all in his imagination. "I should have known," she hadn't made a noise when she'd opened the bedroom door and when he opened his eyes, David was frozen in place. One hand stroking his hard-on over her panties, the other hand circling his nipples, the woman who had inspired it all, smirking at him, "you're a little freak, aren't you, David?"

 

She walked right in, without permission and David couldn't imagine that she'd ever ask. Helen presumed that she ruled the house from the beginning and no one had the balls to contradict her. Actually, that wasn't accurate, Helen had always been the undisputed queen wherever she went, Christie's father had never questioned her authority and now, so far, David hadn't either. She'd asked him a question that he didn't have an answer to. "I guess I am," and it was painful that she had interrupted him at precisely the moment when he was on the verge of cumming. The thought of seeing her gloriously naked, his mother-in-law nude and hovering over him while he based in the sensory delights of her damp panties sent a shiver down his spine.

 

David wanted her so badly, yes, a freak, it probably suited him. "So you like to wear my panties, David? Is that it? Or do you wear Christie's too?" she had to know the answer, her big, blue eyes danced with glee. Helen had to know the power that she wielded, all it took was a glance from her.

 

David lowered his eyes, it seemed disrespectful to look at her face and besides, there was so much to study below. Her black dress clung to her large breasts, her decolletage was on display as usual and David fought the urge to kiss his mother-in-law's bountiful curves as he'd done a thousand times before. Helen had always enjoyed flaunting herself and he had always fallen for her seduction routine. Her voluptuous body wasn't the end of her assets and there were so many inches and dips and places that were kept under wraps that David had only imagined. He gulped hard, his fingers clamped into fists, he wouldn't grab her no matter how much he felt the need to. "No, I don't wear Christie's," it had never even been a temptation. It was only his mother-in-law's underwear that brought his secret compulsion to the surface, "just yours. Please don't tell," he suddenly realized that Helen could just wait another fifteen minutes and then throw the bedroom door open. As usual, she had all the power.

 

She stepped in closer, brushing David's hair from his forehead with her long, red nails, her perfume rising from behind her neck, Helen's breath touched David intimately when she murmured to him. "I suppose that you fantasize about me in these panties, don't you? Is that what you're doing?" she glanced down and his face grew even warmer as he watched her look at his cock. It stood and waved at her under the panties, desperate to get at the blonde beauty that haunted his dreams, "are you touching yourself and imagining my pussy, David?"

 

He quivered when she said the word. How well she knew him, it was uncanny, it was almost as if Helen could read his mind actually. David nodded and groaned as his dick pulsed and dripped, there was a puddle in the crotch of the red, whore panties now and if she didn't let him cum, he was afraid that he'd just keep them wet all night long. "Yes, Helen, I do," he shook his head, there was no holding back any longer, "I always think about your pussy when I jag off."

 

There, she knew, nothing else even mattered, whatever Helen did now, David didn't even care as long as she let him cum. He was weak in the knees and didn't know how much longer he could stand like this, so close, almost touching her, exposed and vulnerable, so very hard and yet, weaker than he'd ever been before. No one else knew his secret and Helen was the last person on earth that should know. She would make his life miserable, David just knew as he watched the corners of her mouth curl up. "What would a panty-wearing sissy like you do with a real woman, David?" her tone was every bit as sweet as always as she sunk the knife in. "Tell me, David," she pushed his right hand away and covered his erection with her own. His cock thrashed to get at her as she rubbed him in her panties, "what would you do with a woman, you little faggot?"

 

His body was wracked with pleasure and his mother-in-law had his manhood in her small hand, stroking him up and down in her panties, he was trapped and far too close to a release. "Oh, Jesus, Helen," he shuddered, a flood of precum gushed from his cock as she squeezed him from root to tip, "please, you're going to make me cum in your hand."

 

Helen chuckled, it was a low, throaty sound and it sounded wicked. The woman was amused at his predicament and she still wasn't letting go. "That's awful, David, what are you going to do?" she raised her brows and David could have swore that she winked. A spasm ran down the back of his legs as she held him with even more pressure in her palm, "if you cum, David, then I guess that I'll be forced to tell my daughter that her dear, sweet husband is a cross-dressing, little homo. What do you think, David, should I tell?" part of him wanted to choke her, the bitch was having so much fun.

 

David sounded as if he were choking and he almost was. His heart exploded in his chest, each beat faster and stronger than the last, she was stroking him faster, up and down, the satin was drenched on the inside and the material was coaxing him, almost forcing him to burst in her hand. David threw himself on her mercy, hoping that she actually had some. "Please, don't tell, Helen, I'll do anything," he whimpered, no matter what he said, it didn't prevent his body from shaking and his dick from thumping for more. Another stroke and then maybe one more, David would gasp and the ecstasy would shoot through his body, "anything you want," he whispered, "just don't tell Christie."

 

She was almost kissing him when she came in closer, his mother-in-law's perfect mounds touched his chest, the red bra burned his flesh as her fingers continued to torment and delight him. "Well, I might not have to tell, David," Helen would leave him with no choice in a moment and he tried to break free from her hand. All he wanted was for her to finish for him, "I might keep your secret, sissy, if you do something for me."

 

He nodded quickly, "yes, yes, god, you have to stop." David didn't even sound convincing when he begged, the orgasm that he'd had in his own hand this morning, the one that he splattered all over the shower, had been for Helen. His beautiful temptress, the woman whose panties he lusted after as well as what was hidden away under the panties, all he wanted was for his mother-in-law to continue. Exploding in her hand seemed only natural after all of the times that she'd inspired him to do the same.

 

"Do I?" she was only holding his cock now. The wet satin was wrapped tightly around his erection and her soft, small fingers clutched his dick, just under his head, squeezing just enough to keep the rivulet of his precum running, "if you don't cum, then I won't tell. But that means that tomorrow afternoon, you will have to do something for me." She gave him one last pull and David threw his head back, his body belonged to her and a howl of ecstasy would erupt from him, "and you have to keep wearing the panties and bra until I say you can take them off, faggot. Is that understood?"

 

She released him and David reached out for the wall quickly with this left hand to steady himself. He would have fallen at her feet, as it was, his cock thudded for her attention in the front of Helen's sopping, wet panties and he nodded, yes he understood that his mother-in-law now owned him, body and soul. "Yes, I'll wear the underwear," he would be locked in satin and lace and every nerve would call out for relief.

 

The front door opened and David heard Christie call out for him, "David, hey honey, I've got groceries, can you help me?" If his wife headed for the bedroom, the jig was up. It wouldn't matter what deal he had made with Helen the devil, there was no explanation for his cock right now.

 

He called out, "yeah, I'm just changing, I'll be right there."

 

Helen blew him a kiss, "remember, no cumming David and you can only wear those red panties. If you break the rules then Christie will have to know everything. I'd hate to see what happens to you if you break my daughter's heart."

 

His mother-in-law opened the bedroom door and David was torn as she sashayed down the hall. Part of him wanted nothing but to rip off the tainted underwear and get back into his boxers. This was his goddamn house after all, since when did Helen make the fucking rules around here?

 

He'd throw her out on her ass.

 

The other part of David wanted to finish himself as he watched her walk. Ass jiggling with every step, her heels clicking down the hall, her calves were a curve that disappeared under the hem of her dress but his imagination could fill in the rest of the details. His mother-in-law had beautiful thighs and he could almost feel her creamy, soft skin under his fingers. It would only take him seconds.

 

David didn't want to take any chances. Instead, he stuffed his aching dick back into his khakis, threw the polo on and ran to help Christie with the groceries. There was no sense in tempting Helen, or fate as the case might be.