Sissy Son-In-Law
Art and story by Prim

  Marion sat down opposite her son-in-law's play-mat and settled back to watch him playing with his row of dolls as he changed their lingerie. Yes she thought, he loves the doll's lingerie, but only because they represent her own bras, panties and slips. It was them that he loved with a passion. He sat with his legs demurely together and to one side, the lacy legs of her own panties peeping above his stockings. She suppressed a giggle at the wig she had bought for him, dripping with little-girl blond ringlets. He looked so girlish with his delicate arms and legs, wearing his A-line girl's dress in apricot silk-satin, and a smile settled on her ruby lips.

The young husband looked up at his Mother-In-Law and smiled back. What a blissful Saturday morning he was enjoying with his beautiful Momsy. How feminine he felt, with all the lovely feelings that girls enjoy in their panties and petticoats and dresses. "Change Jemima for Momsy, my darling," she said. "Put her into her white nylon panties and bra with her matching slip."

It wasn't every mother who had a new little girl aged three, happy to play with his dolls in front of her and actually wanting her to look down on him as a sissy and a weakling. But it was what he had asked her for, so it was what he was getting. A flush of pleasure filled her own breast as she recalled the day just four weeks earlier when she had challenged him for always complimenting her on what she was wearing.

"You always notice what I am wearing, Patrick. You are so attentive to my appearance. I can only guess that women's clothes interest you."

He went quiet; strangely coy and almost submissive. "I like the way you dress, Marion. You've got," and he paused to pick his words, "wonderful dress sense - and I find it attractive."

"Oh, you find me attractive?" Marion saw the chance to suck him into a difficult corner, and turned her better side towards him while allowing a supposedly nervous smile to linger on her lips.

"Er no - Marion - I like your clothes," but instead of stopping there he went on: "I like you in your silk blouses and wide skirts."

Marion let this confession linger a moment on the sitting room air, then called him close to her. She was wearing a blouse in rose pink shuddered silk scattered with tiny sprays of rose buds, and her A-line skirt in bronze taffeta, worn over three sizzling underskirts. "Kiss the sleeve of my blouse, Patrick," she told him, "here at the shoulder."

It wasn't clear to her whether his hesitation sprang from shame at having confessed such a weakness to Zara's mother, or whether he was so thrilled at the idea that he could barely put one foot ahead of the other. But he did. He strode across to her armchair, averting his eyes, and bent at the waist to plant a kiss on the puff of silk above her shoulder.

"That wasn't a kiss, it was a peck."

He bent again, his arms by his sides, and kissed her shoulder with more meaning as she watched him, his hair an inch from her nose. She reached under him and lifted his chin with a single finger. Had he done wrong? Was he now guilty of overstepping the mark in his Mother-In-Law's house?

"Kneel down," said Marion, "and kiss my sleeve." She had her forearm laid along the arm of her chair. He was silent, barely breathing, and sank to his knees in his slacks and white polo shirt. As his lips descended onto her sleeve, she used her other hand to hold his head. "Hold my sleeve in your fingers," she said; "both hands." He did, and she held him kissing her blouse for five full minutes. He wasn't going to stop. His pleasure ached in the flies of his trousers, aching because Marion was granting him such familiarity, such indulgence of his weakness. Her finger lifted his face again and she got to her feet. "Sit in my chair," she said, "and don't move."

She left him alone in her sitting room, pondering what kind of defenceless situation he had managed to get himself into. She returned two minutes later with an armful of her things and laid them over the back of the settee. Patrick felt a lump in his throat. He saw her bright red blouse and wondered what she was going to do. He tried to be polite by sitting bolt upright on the edge of his chair and watching with wrapt attention.

"Now," she said, "are you going to kiss them, or am I going to dress you in them?"

Her son-in-law's mouth trembled as he parted his lips. "I-I-I'd like you to d-dress me in your clothes, Marion - please."

Marion lifted her brows, without a smile, and a minute later he stood naked in front of her for her to dress him in her bra and panties in white silk, with a matching full slip that slid coldly down his body, followed by her magenta satin blouse - plain with a large pointed collar and revers and a narrow skirt in dove grey silk polyester. It showed the full extent of his arousal, to his agony.

"Put your hands by your side," she said, "and turn slowly round for me." He cringed with embarrassment at the urgency of his erection, all the worse because of the whitish skirt that he wore showing the upward, rounded point. Her skirt, slip and panties tugged deliciously at his cock.

"Mmm, you do like my clothes, don't you?" she said.

"I-It's because your clothes are just about the ideal ones for my - er - to make me interested." Marion sat looking at him as he stood in front of her, her nose lifted high as if she were a superior woman, and her face to one side as if waiting for more. "You see - Marion - I shouldn't really be telling you this but - I have dreams. Fetish dreams, where I am dressed by older women. Attractive older women, like yourself. They dress me as a little girl, because little girls wear such pretty clothes. And the women who dress me would wear your clothes."

"But little girls' dresses wouldn't fit you."

"Ah but you can buy them on the internet - full adult size little-girl dresses." He felt he was getting himself into deeper and deeper water, and Marion's face had changed. Her lower lip was sucked in as if in serious thought, then her eyes brightened.

"I don't know about little girls' dresses, but I can dress you in some of my things, like today. On Saturdays." Her son-in-law's heart gave a skip. "You can tell Zara that I want you to do my housework and shopping - she'll be delighted."

Yes, that was how it started. So her weak and effeminate son-in-law began coming to her house each Saturday at 9 o'clock. Marion put him into her clothes, from the skin outwards. On that first Saturday of September she had him in stockings and a girdle, then in her lingerie, topped with a pleated brown skirt and her evening blouse in mint green satin. He was going to do her housework, so over her clothes she put him into her frilly, bibbed floral apron. He was the picture of a Stepford Wife.

The following weekend, however, she informed him he would wear either an apron or a shiny nylon housecoat - either the crisp lemon one or her checked housecoat in two shades of pink. "But I don't want you doing housework, my boy. I would make a better job of it myself. I want you doing my ironing. Come with me to the kitchen."

There he found the ironing board and iron awaiting him, along with a rack of Marion's full cut pairs of panties, her slips, her blouses and her skirts. "Put your arms in here," she ordered, and his blouse slid with a hiss of coffee silk into the sleeves of her crisp pink nylon housecoat. When he was nicely buttoned up, she sat on a high stool to watch his efforts at ironing the clothes that he adored.

But all that was weeks before. Yes, he loved doing Marion's ironing in her dreamy rustling clothes, but his Mother-In-Law had been quite taken with his dreams of being dressed by a firm 'matron' in clothes that would suit a little girl. And that was why Patrick Guildford sat in front of her now, changing his dolls' lingerie while dressed in a cute A-line dress and a pair of her own voluminous panties. His name was now Poppy, and he would show his darling 'Momsy' how good a girl he could be while wearing his little girl dresses for the remainder of his 7 hours at her house. She had even arranged a visit to add to his sissy-girl excitement.

"I have a surprise for you, Poppy," she said.

Poppy looked up. Delighted. Did Momsy want to sit him in her lap and change his panties already?

"I know that you feel a kind of sissy boy thrill while you are dressed as little Poppy in front of me. It makes you feel rosy and pink, doesn't it, with me seeing how girly you are in your dress and petticoat?

Patrick hung his head and didn't reply.

"Well I am going to add to that thrill, because I am expecting a visitor this afternoon. Miss Jones will be calling at 2 o'clock, and she will see you wearing the new little girl dress I have got for you.

Her sissy little girl's heart almost stopped. "Is that Miss Jones who taught me in tenth grade?" He pictured the middle-aged woman whose greying hair was always set perfectly - a large-breasted woman, all blouses and beads with widely pleated skirts that he used to long to lie across while she spanked his naughty bare buttocks.

Marion nodded. "She is longing to see what a good little girl you can be for her. That is why I have bought a special new outfit for you, my darling: a new silk dress with bonnet and bloomers to match."

Patrick's body tingled in every part, a mixture of fright and yet desire for Miss Jones to look down on him in his shame and his sissy weakness.

"Come and sit on Momsy's knee, Poppy," said Marion. She straightened her pleated skirt for him and he lowered himself reverently into her lap. A warm flush of pleasure ran through him as her primrose silk blouse closed round him and her long fingers clasped his face into her blouse bow where it cascaded over her breasts. She gave him a tight hug, then relaxed her arms and frolled her fingertips over his blushing cheek.

"Well, my cute little kitten, do you want to be my little girl every single Saturday of your life?"

Patrick curled himself into an even tighter ball in her arms. "Yes please, Momsy."

"Hmm, well to tell you the truth, my dear, I am satisfied that you will remain as my sissy girlie. The last thing I want is a macho man trying to be the equal of my daughter, and maybe even having affairs with other women. I am quite happy to build your pleasure and thereby consolidate your dependence on your Mother-In-Law."

"Oh thank you, Momsy. I'll be a very good little girl for you."

"Good. I'm pleased to hear it. Now sit up, darling, I want to see if your lovely hair will fit inside the new bonnet I've had made for you."

The bonnet was in apricot silk-satin, the same as his dress. She undid his hair ribbon and slipped off his flowered head band, then pulled the bonnet onto his hair from the back of his head, feeding his ample blond ringlets into its expanding hood. The stiffened wings gathered into his cheeks as she did the ribbons under his chin and made them into a pretty bow. Then she settled him back on her arm so that his bonneted face was against her left breast and she could gaze down into his eyes with her own face almost inside his bonnet. She caught his hand and presented it to his mouth.

"Suck your thumb for Momsy, pet. There's a good girlie. Isn't it nice to be Momsy's little girl?"

The apricot bonnet nodded vigorously.

"I can see how lovely you feel, curling into a snuggly girly ball for Momsy. Say after me: I love lying in Momsy's lap."

He spoke with his thumb still in his opened mouth. "I love lying in your lap, Momsy."

"Say - I love Momsy holding me into her satin blouse."

"Oh yes, Momsy, I love you holding me into your satin blouse." His bonnet tried to slide even deeper into Marion's bust.

"And say Momsy makes me feel lovely and feminine."

His face blushed a deeper red for her. "Momsy, you make me feel lovely. I feel so feminine."

Marion's lips beamed a wide smile. She slipped the end of her forefinger into her mouth and sucked on it, then took it out, glistening with mommy saliva, and slid it up and down her little girl's nose. "Now," she said, "it's time for Momsy to put her little pet into another pair of Momsy's panties, so that she becomes even more of a little girl. She reached down to the floor beside her chair and lifted into his view a pair of oyster pink satin panties, prettied across each leg with pink and white lace inserts.

Patrick gasped with pleasure. They were Marion's panties, and they were so full and so glossy. "Oh yeth pweathe, Momthy," he bleated as she sat him up on her lap. She held the panty waist elastic down to the knees of her skirt and threaded them over the stocking feet that he presented to them. Ooooh, the blissful sweetness as they slid up his stockings, onto his suspenders, and over her white panties which he was already wearing. He mewled with pleasure in her hands as Marion adjusted the panties until they were just right. But a niggling worry was working at the back of his mind.

"But Momsy," and his heart began to patter beneath his dress, "what if Miss Jones gives me away to Zara? I would be in terrible trouble, and I wouldn't be able to come and do your ironing on Saturday's."

He looked up into Marion's eyes as she shook her head from side to side. "No need to worry, darling. Miss Jones knows this is our secret between little Poppy and her Momsy-In-Law, and she tells me she would like to come and help me look after my little girl on Saturdays."

Patrick gave a long, blissful sigh, feeling the tug of two pairs of panties on his sissy clitoris and knowing he was going to feel terribly ashamed in front of Miss Jones, his former schoolmistress.


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