Mum & Sister Dress Him Up

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Dumped sissy returns to mum and sister who enslave him.
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Quietoldie
Quietoldie
1,007 Followers

"This is my rented flat you know Michelle. It's not fair you being like this with me. I've always been good to you haven't I?" Peter says. He often seems to get into situations like this. He was never very good about sticking up for himself. Now his girlfriend is chucking him out just because she found him dressing up in her things.

"I just don't want to live with you anymore." Michelle replies. "So pack up your things like a good boy and go back to live with your mummy. If you don't go I'll tell all your friends about your little secret. Listen, you can still come around sometimes but phone me first okay? Perhaps you're a bit young for me. I know you're twenty-one now but you act a bit younger than that. You're kind and thoughtful and you allow me to boss you around but I suppose I prefer a more macho man. You're also a bit on the small side aren't you?"

"Small? What do you mean?" Peter doesn't need to have it spelled out. He's blushing crimson and the blood is rushing to his genitals. Michelle had never said anything but he'd often noticed her looking at his equipment and smiling broadly. He'd known exactly what she was smiling about and thinking how inadequate he was had helped him to "stand proud".

"I think you know what I mean. I had a few boyfriends before we met, some bigger than others but I never went with anybody whose willy was the size yours is." Michelle holds up her index finger and thumb three or four inches apart in demonstration. She notices the slight bulge in his trousers and has an idea.

"Well, Pete, or should I call you little Petey, ha, ha. Why don't you take your little chipolata out and stroke it whilst I watch. That's it, get it out, that's my boy. Now I want to see you wank for me. You like to wear panties like a girl don't you Petey? That little willy is tiny isn't it dear? I could hardly feel it when you fucked me, did you know that? That's why you always had to lick me before I'd come. You're a good cunt licker aren't you darling. You're a little cunt licker sissy wanker." Michelle smiles to see him spurt down the front of his trousers as expected.

Peter doesn't answer her questions. He'd be quite happy to stay with Michelle and wank for her whilst she abuses him but realises it wouldn't work. Embarrassed and defeated he gathers up his belongings in a few black plastic bags and leaves the flat. He phones his mum and she says it's okay for him to move back in to his old bedroom.

"Helen's moved in with a girlfriend to be nearer her work. She comes home weekends so you'll be company for me during the week." His mum says. Helen is his older sister, there's about seven years between them. His dad left his mum ten years ago and he never sees him.

Peter enjoys the company of women. He sometimes feels things would be different if he had had a male role model as he was growing up. He's always been fascinated with what women wear and thinks men's clothing is rather boring. He'd been trying on some of Michelle's things quite a lot whilst she was out so moving back home presents him with problems. He knows it's a fetish but he can't give it up.

Taking his courage in both hands he goes into clothes shops to either steal or buy some lingerie of his own but finds he just can't bring himself to do it. It's just too embarrassing for him. It's inevitable that he eventually goes into Helen's bedroom and tries on some of her panties and other clothes. The feel of the silky smooth material on his body is heaven and he becomes aroused. He often masturbates wearing them remembering Michelle's words just before he moved out.

About three months after Peter's mum Marge took him back she bumps into Michelle in a pub. It's late in the evening and they've both been drinking.

"Hello Marge, is Peter still staying at yours? I've not seen him for a week or two." Michelle says, slurring her words a little.

"Yeah, Peter's the quiet type as you know. Give him a ring if you want to see him again. He still thinks a lot about you." Marge says. She feels no animosity to Michelle for kicking him out. She likes to live and let live.

"Peter's okay but I didn't want to get tied down with one bloke. You know what I mean?" Michelle winks at Marge who smiles back.

"Yeah, I heard you'd been putting it about a bit." Marge has had a lot to drink but realises what she's just said. "Sorry Michelle I didn't mean any offence."

"None taken. By the way, you do know about Peter's little fetish don't you?" Michelle says mischievously.

"No, what's that?" Marge says

"He's into crossdressing. I found him wearing a pair of my panties."

It's the weekend and the next day Marge can't wait to tell Helen what she'd heard the night before.

"Let's see if we can catch him out. You're more his size so he's probably going in your room." Marge says.

Helen has her suspicions so they keep a very close eye on her panty drawer until, sure enough, it's obvious he's been taking her knickers and replacing them later. Both Helen and Marge find it quite amusing. They don't take any action immediately but decide to plan a surprise for him. They are both excited about what is to come and masturbate privately thinking about it.

Marge buys an expensive pair of pink satin panties, the sort she suspects that Peter would like and places them prominently in her daughter's knicker drawer. The next morning the two women tell him they are going into town shopping. He is still in bed upstairs but awake. Instead of going out they hide downstairs. They are managing to keep an eye out for any movement upstairs without being seen. They hear him moving about and see him walk into Helen's bedroom. They wait for a few minutes then creep upstairs. Peter is completely surprised as they enter Helen's room to find him naked apart from the new panties.

"Some cocks were made for panties." Marge tells him with a grin. "As you can see we set a trap for you."

"We've been aware of your little secret for a while now." Helen says grinning. "That slut of an ex girlfriend of yours put us in the picture. We bought them for you to wear. Please don't take them off. He makes a pretty picture doesn't he mum? I think I'll take a photo."

Whilst Helen is clicking away with her camera Marge starts looking through Helen's wardrobe and drawers.

"You wouldn't want our pictures to be posted on our Facebook pages would you Petey? Let's get you dressed up properly like the sissy you are. We've got plans for you, big plans. You will be doing as we say from now on won't you dear?" Marge says looking at Peter's startled face. He seems unable to speak. "By the looks of that little prick of yours you might even enjoy it."

Peter is already extremely embarrassed to be caught in his sister's panties but he can't hide the fact that his willy is sticking up like a piece of wood. He tries to say something but it is as if he is wearing a gag. What can he say? Would it make any difference if he did speak? Part of him is thinking it could be quite exciting to submit. He'd read stories on the internet about men being forced into frillies.

"Give us a hand Helen. He'll need a bra to make him into a proper girlie. Here stuff these panties into the cups. That's it. Now let's see what he looks like in this dress. It's nice and short, showing plenty of those gorgeous legs he has. Have you been shaving them you naughty girl?" Marge says.

"No mummy." He's never had much hair on his legs and what he has is almost invisible. For some reason Peter has reverted to childhood, he always calls her "mum" these days.

"Mummy eh? Quite right. You'd better call me that from now on. It's more respectful. And Helen will be Mistress Helen from now on or just Mistress. Is that understood?" Marge says sternly.

"Yes mummy." Peter says allowing the two women to dress him. He loves the feeling of the hold up stockings, so silky and smooth. The two women watch as he touches his knee and draws his hand up to the point where he reaches bare skin.

"Don't go any higher. Your little willy is strictly off limits. You're not saying much are you? Repeat what I've just said." Helen says grinning broadly.

"I've got to keep my hands off my cock Mistress Helen." Peter says respectfully.

Both women are feeling quite squishy down below. Power is such a strong aphrodisiac. Helen removes her dress and sits down on her bed. She opens her legs wide showing Peter a clear damp patch at the crotch of her pale blue panties.

"Get down on your knees young lady. Help me off with these panties, then, you know what to do don't you?"

Peter kneels down immediately and crawls over to Helen. He can't wait to get his head between his sister's legs. He's always imagined this in fantasy. It's such a bad thing to do. She hitches up her bottom to make it easy for him as he reverently draws her panties down her legs. Then Helen opens her legs wide for him.

"That's it little Petey, put your tongue to work. Ooooh! You are good at this aren't you? Must have had plenty of practice with Michelle eh? Well you'll be on your knees a lot now you've moved back home. Won't he mum?" Helen says wriggling a little as she holds his head closer.

"Oh yes, you're a little sissy cunt licker from now on, that's for sure. I met your Michelle down the pub and we had a long chat about what turns you on. It may be a bit weird to some but we can put you to good use. I'll bet you'd love to do the housework for us in a pretty French maid's costume wouldn't you little Petey?"

Peter pauses for a moment, looks up and says, "Yes mummy."

"Good girl. Now get back to work. Give your sister's bum hole a good licking. When she's had a couple of orgasms you can give your mum's cunt a turn. I've been missing out lately. Michelle says you're not much cop when it comes to fucking but I'm not too fussy. I've not had a cock up me for over two years now." Marge sighs with pleasure as she strokes herself through her panties enjoying the spectacle before her and anticipating what is to come.

Peter is reluctant to move to Helen's other hole but realises he has to do as he is told. Helen moves to give him access and, as his tongue probes her little rosebud he senses that her first orgasm is building. He realises that licking this forbidden area is turning him on too and worries that he might spurt without anything touching his penis. He desperately wants to hold back knowing that, if he does, he will be unable to give his mum what she wants. He doesn't know why he is so keen to earn the title "motherfucker" but realises that is exactly what he craves. Helen begins to moan and wriggle around as her orgasm explodes. But as her mum predicted she still wants more and orders Peter to, "Suck my nipples whilst you finger my cunt, sissy, there's a good girl."

Peter is happy to comply. His sister's tits are medium sized but her nipples are huge. She'd removed her bra for him whilst he was busy with her cunt. He relishes her naked body. After a few minutes Helen sighs and pushes his head back down to its original position.

Helen is having the time of her life. She could never get any of her boyfriends to spend all this time sexing her. "Suck on my clit sweetie, gently now, ah, that's the way. Oh. Oh. Oh." She cries, feeling her second orgasm coming. Her moaning continues louder and louder until Marge is fearful of complaints from the neighbours. She smiles; "Fuck the neighbours", she thinks to herself.

"Now it's my turn little Petey. I want you to lick me with my panties on first." Marge says standing before him holding her dress high above her waist. Do you like what you see?"

Peter looks up at her from where he is kneeling.

"Yes mummy", he says.

Marge opens her legs wide. "Crawl over here".

She remains standing whilst he enthusiastically licks her panties which are already wet with her juices. She allows her dress to fall onto his head then grips his head tightly forcing him hard up against her cunt. His nose pushes the panties into her slit. He's unable to breath but at first this doesn't faze him, he licks for all he's worth.

"You're my little sissy now, aren't you darling? Now be a good girl and move the crotch to one side. That's my girl, keep licking". Marge says, pulling him hard against her again. She enjoys the feeling of power as she towers above him, gradually easing him forwards as she moves backwards until she is against the wall. She loves his subjugation.

"I'm going to enjoy training you to be our slave. I'm sure it's what you want isn't it darling", she says.

Once again Marge is pulling Peter against her crotch making it difficult for him to breath. His nose is buried deep inside her cunt. He enjoys the feeling of suffocation strangely revelling in his mother's cruelty. Marge is now ready to feel his cock inside her. She pushes him off her.

"Come on Helen. Let's tie her onto the bed. I bet she'll enjoy that. I want to ride her cock."

They quickly find a few ties and belts and make a pretty good job of fastening him down spread-eagled on his back still wearing the panties. With his wrists and ankles secured to the four legs of the bed Peter's cock is twitching with excitement. He's delighted that he's managed to avoid spurting although he notices a mark on his panties from a small amount of precum.

Marge strips off all her clothes and climbs on top of him. She's a large woman with big tits. She moves the crotch of the panties to one side. She lowers herself onto him, kneeling, facing him.

"Helen, love, do me a favour and check I'm in. She's small isn't she? This isn't a cock it's more like a clit don't you think?" Marge says.

"Yes, you are in. I agree she is tiny. It's no wonder Michelle gave her the push. All she's really good for is licking cunts." Helen says. Peter is just an object for their pleasure. They've stopped talking to him now, just talking about him.

Marge begins moving up and down her tits bouncing as she moves. Peter can't help himself, he spurts far too soon for Marge. She cries loudly in disappointment as his cock subsides, angrily moving forward and sitting down hard on his face. Soon she's rocking back and forward denying him the chance to breath for a third time. He has no chance to move his head away trapped by Marge's lower legs. She's clearly punishing him for his premature orgasm.

"You're getting a caning later, young lady." Marge says. This thought seems to excite her and she soon orgasms on his face moaning loudly. She rolls off him and Peter, red faced, takes a deep breath at last.

Next morning Peter is all ready for work when Marge decides to carry out her threat. She hands Helen a springy cane and makes him bend over with his pants around his ankles. She notices, with a smile that he is wearing a pink pair of Helen's panties under his grey slacks.

"Give him twenty across his bare bottom Helen dear," she says. "He needs to learn some discipline whilst he's in our house. Two more for every time he moves."

Marge enjoys a cigarette as she sits and watches Helen's arm rise and fall. Both women take great pleasure in the caning, especially Helen. Their cunts are flushing as the cane does it's work. Helen realises that she will need to change her panties before leaving the house. She may need to masturbate too. The cane hurts like hell and Peter moves twice earning 24 strokes in all. He works in an office and the pain continues throughout the day, stronger each time he sits down.

Following on from the caning Peter knows he has to obey his mum and sister if he is to avoid a repeat. They use and abuse him but knowing his liking for dressing up and humiliation they are relatively kind about it.

One weekend Helen invites a few of her female friends round and Peter is there to serve them dressed as a maid. They all find Peter's outfit hilarious and become quite horny teasing him. Their clothes are soon discarded and one woman places her panties on his head and pushes another smelly pair under his nose to sniff. He does enjoy their attention.

Helen is away working during the week so Marge has him all to herself. They have been out shopping together for his sissy clothing and she makes sure the shop assistant is fully aware of who the clothes are for. Peter is embarrassed but also aroused by this state of affairs. She makes sure he is in full sissy gear whenever he is at home and that he wears a nightie in bed.

"I don't want you entering my bedroom under any circumstances. If I'm feeling randy in the night I'll come into your bedroom. Make sure you have your nightie on. Is that quite clear?"

"Yes mummy." Peter knows his mother is a light sleeper. She sometimes wakes up in the night. On the first few nights that they are alone in the house he struggles to sleep. At first his bottom is sore from the caning, later on he finds he can't settle, waking up if he hears his mum walking about. Usually she is just getting up to pee.

Then one night she comes into his room as he is getting undressed. She is wearing stockings and a strap on dildo, nothing else. "Lie on the bed near the bottom. Let your legs dangle over the edge there's a good girl. Take those panties off, I want to take your virginity, then you'll be a proper sissy. Peter steps out of his panties and lays back on the bed. Marge grabs his legs and eases the dildo into his bum hole.

The pain is indescribable at first but she fucks him gently and soon he begins to enjoy it. He notices his penis becoming hard.

"There, there, dear, no need to cry, you'll soon get to like it. Sissies love to get their pussies filled. I want you to keep your pussy nice and clean for me. I'll be paying you regular visits in the night from now on. Now show your gratitude like a good slut."

"Thank you, mummy. I'll look forward to your visits."

Quietoldie
Quietoldie
1,007 Followers
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AnonymousAnonymous8 months ago

His mother and Sister should not degrade him but help him he has a tendency to like women's undergarments that's women's clothes that's OK but they shouldn't degrade them and take his virginity it's not right but that's a story so it was a good story but all the best

AnonymousAnonymousalmost 2 years ago

Why in the hell would anyone treat there child or brother like that? Discussing!!!

cdCindy1cdCindy1over 4 years ago
Turned me on so much

Licking my mom's and sister's cunt is my dream. I hope to one day .ake it happen, with me dressed up just like In your story. Please tell more like this.

AnonymousAnonymousalmost 6 years ago
Enjoyable!

I slipped into the hot water tub with all good intentions of masturbating with a good story. This one is HOT. Yet I couldn't help smiling all along because this is something I clearly visualize my sister doing! LOL In any event, yes it was a nice orgasm and your story just as enjoyable.

lingerie65lingerie65over 6 years ago
Caught in delight & humiliated to her delicious deli

A short yet fun read, still I myself truly enjoy slipping into femininity, her punishment needed more lingerie so she could wear. Truly her dressing up would been a beautiful female experience she would've loved....

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