The family that lays together, stays together…by Naomi Matthews

sissy lingerieAlan and Annabelle were twins, born within minutes of each other and virtually identical. Even from a very early age, people struggled to tell the two apart and as soon as they were old enough, both siblings would often exchange clothes and dress up as each other just to confuse people. Alan was always very convincing as a girl and when he adopted a falsetto voice, often it was very hard to tell the two apart.

Although neither sibling was ever short of friends, they were both so close as brother and sister that most of their preferred time was spent hanging out with each other. But Alan especially was always happier when he was around his sister’s girlfriends than he ever was with any of his male friends, and because he was a lot more effeminate and in touch with his girly side than most other boys the girls knew, they didn’t particularly mind either.

It wasn’t that Alan was gay, or attracted to guys – not that there was anything wrong with people who were – he just had more in common with girls. He didn’t play, or have any particular interest in sports, and was just more into fashion and make-up.

His ideal time to have lived, he often thought, would have been way back in the eighties at the time of the New Romantic period, when no-one turned a blind eye at a boy dressing up as a girl, but he had just been born a few decades too late for all of that.

By the time they reached their teens, most of Annabelle’s girlfriends were convinced he was gay, and still in the closet – despite his protestations that he was not – and barely paid him any mind, or saw him as much of a threat, and so he could often be found hanging out in his sister’s bedroom while the girls all got changed for a night on the town in front of him.

And Alan was convinced that was where his love of high heels, stockings and suspenders, and all things silky and satin was first born.

He became obsessed with women’s lingerie and so, when he cane across a pair of discarded panties in his sister’s bedroom that one of her girlfriends must have misplaced while getting ready, they soon became one of his most treasured possessions.

That first night, as he lay there in his bed, he brought them to his face to breathe in their womanly scent, and soon it became his regular habit to wear them, and pleasure himself in, whenever he went to bed.

Soon he was also borrowing his sister’s and his mum’s dirty panties so he could breathe in their heavenly scent as well while he played with himself, and even began borrowing one of his sister’s bras whenever he was alone, but to begin with that was as far as it went.

At least, that is, until he got caught…

***

Halloween was Alan’s favourite time of the year – because then he could always dress up as a gurl without fear of being ridiculed.

His mum and dad were dead against the idea the first time he and his sister suggested it, but after he won first prize in the local annual fancy dress competition two years in a row, it soon became a regular thing and just something everyone who knew him accepted.

It had been his sister’s idea to begin with.

She had come home early from college one afternoon, and had caught him parading and mincing around in her bedroom dressed in her bra and his stolen panties. They had been struggling to come up with an idea for this years costume for the annual Halloween competition, but seeing her bother dressed so had given her an idea.

In the past, when they were very little, they had often entered dressed as a Raggedy Anne and Andy – with Alan all dressed up as Raggedy Anne – and growing up, one of Annabelle’s favourite games had always been to dress him up in her clothes and make up his face; essentially using him as her own living, little dressing up doll – but only when their parents were out of the genius’s, or they were confident they would not be disturbed. But then as they had grown older, both twins had started to realise just how weird that was and so had eventually stopped, much to Alan’s secret and bitter disappointment.

That day, seeing her brother with his hair all grown out – as was the current style – and all dressed up in naughty underwear, suddenly all the old feelings she had used to feel dressing him up had started to re-emerge.

“Are…are those Beth’s panties?” She had asked him, embarrassing poor Alan and making him blush. “She thought she had lost them, left them round her boyfriend’s or something while he was feeling her up. I had no idea you might have taken them…but I tell you what, little brother, you look a lot cuter in them than she ever did!”

She had taken photos of him on her phone, and had then insisted he dress up as a girl for the upcoming Halloween fancy dress competition, or else she would show all the pictures she had taken to their mum, and had been both shocked and delighted in equal measures when he had agreed.

That had been the first year and the tradition had carried on ever since…

***

Now it was 2020.

A global pandemic had struck all across the world and here in England, strict quarantine measures were about to be out in place.

Knowing that at any time they could be made to stay inside, and the whole country put under lockdown, one of their neighbours had decided to throw one last, big shindig – a costume party – before the P.M could decide to implement regulations and restrictions on all social gatherings.

A move everyone knew was no more than a few days away.

Of course Alan and Annabelle asked if they could go, but both their parents flatly refused them.

“It won’t be your type of party anyway,” their mother told them.

“No,” said their father. “It’ll just be us and a few stuffy old farts getting posed drinking beer and wine, and eating cheese on sticks while we all take turns to moan about Boris and the state of the country.

“Not your kind of thing at all.”

But Alan and Annabelle were not so easily dissuaded.

It wasn’t without precedent, and wasn’t the first time their parents had gone round to the neighbours for a party without them.

In the past, Annabelle had often made a joke if it, and suggested that their parents might be swingers, but Alan had always said that he didn’t think either of their parents were that exciting.

That was up until recently.

Annabelle had shown him the Sissy-hypno videos she had found buried on their father’s computer, along with all the pictures of prissy Sissy boys all dressed up in silk and satin he had saved – and that had triggered all sorts of naughty fantasies in Alan when he was alone in bed at night – and had shown him their mother’s secret stash of sex toys she had stumbled across when she was snooping around, and suddenly the two of them had slowly started to realise that both their parents were perhaps not so straight-laced and vanilla as they had once thought they were.

Now, back in his sister’s bedroom, Annabelle asked her brother if she thought their parents might be going to another of their ‘sex parties’ the twins were both convinced their parents were involved in.

“I don’t know,” Alan replied. “But it might be fun to find out…”

And right there and then, both twins resolved themselves to go, by hook or by crook, no matter what else happened in between.

***

It was Annabelle’s idea for Alan to go dressed as a gurl.

“If we’re going, we need to disguise ourselves so our parents don’t recognise us at the party,” she said. “And what better way to disguise you than to dress you up like a gurl. It’ll be just like old times, and I promise to make you look convincing, and not just a boi in drag.

“I already have a couple of costumes that mum and dad haven’t seen yet – remember when I ordered my fancy dress outfit for Beth’s Sweet Sixteen party that now doesn’t look like it was going to happen? Well, it was buy one, get them free and as we’re both nearly the same size…”

She left her statement open, but Alan knew exactly what she was thinking and where she was going with this conversation.

“You’re thinking, I could wear the other outfit,” he said.

“Precisely,” his twin said, clapping her hands together in excitement.

“So long as you don’t make me look stupid,” Alan said.

Annabelle grinned.

“By the time I’m finished with you, little brother, you’ll be beating all the boys off – pun intended – and no-one will ever guess that it’s you. Who knows? You might even get a little action…”

Alan blushed.

“I’m just teasing you,” his twin sister said. “We’ll show up, have a good time, see what’s going on, and if it is what we think it is and things start getting out of hand and people start copping off all around us, we’ll just leave.

“What could possibly go wrong?”

Alan didn’t know but he had to admit, the thought of dressing up as a gurl and going to one of his parent’s ‘parties’ did kind of excite him.

What could possibly go wrong indeed?

***

It was the night of the party – the countdown to lockdown party.

Annabelle had asked her best friend, Beth, about the party because it was being held at her parents house, to see if it was going to be what both twins thought it was, but Beth had said she knew nothing, and that had not been invited either and had been told she had to stay at another friends of theirs for the night.

As soon as their parents left, both twins got themselves ready.

Annabelle was going dressed in a sexy Little Red Riding Hood costume – all silk and satin, with matching red stockings and high heeled Mary-Jane shoes.

Alan was going as a naughty St.Trinians school girl – with black fishnets, high heels, and a sexy school girl uniform that left very little to the imagination.

His sheer silk blouse showed off the lacy black bra he was wearing underneath, and Annabelle had given him a pair of breast forms to make it appear like he had cleavage.

By the time she had fitted false eyelashes to them both, and made up both their faces, complete with semi-permanent lip gloss so it wouldn’t smudge, Alan could barely recognise either of them in the mirror.

The two twins looked like a pair of very sexy, slutty sisters, all dressed up to kill, and ready to go out on the prowl.

“Are you ready, Sis?” She asked him, and Alan nodded. “We need to give you a girly name for this evening,” she said. “I can’t call you Alan when you’re all dressed up like this. For tonight, I’m going to call you Alannah, and I’ll be Anna, okay?”

Alan…now Alannah…nodded again, her pigtails bouncing as she did so. His sister had even drawn freckles on him, he noticed in the mirror, and the whole thing made him look like a cute teenage gurl, rather than the boy that he was.

“Well, what are we waiting for?” Annabelle, now Anna, asked her new sister. “Let’s go have some fun!”

***

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Alannah felt weird being out of the house, all dressed up as a gurl.

It was one thing on Halloween, when everyone knew it was her and kind of expected her to be in costume, but to be doing it on a normal weekday – and not quite knowing what to expect at the party they were going to – was making her nervous.

Anna, formally Annabelle, sensed her ‘sister’s’ discomfort and took her by the hand. “Relax, it’ll all be fine – and like I told you, if things start getting too uncomfortable in there, we can both leave, okay? I promise,” she said, and Alannah nodded.

The party was already in full swing when they got there.

Anna and Alannah slipped in a side door, and instantly began mingling with the guests. It looked very much as if most of the adults in the neighbourhood were already here. Anna could tell her ‘sister’ was nervous from the furtive glances she kept casting around her.

“Just stick close to me and everything will be fine,” Annabelle told her, reassuring her, and took her by the hand.

There was a big bowl of punch in the living room, and Anna headed straight for it and ladled them both out a large glass. Whatever was in the punch, it was seriously alcoholic, Annabelle thought, for as soon as it passed her lips, she felt it going straight to her head.

Alannah had already downed hers and was already reaching for another.

“Just take it easy, that shit is strong,” Annabelle tried to warn her ‘sister’, but no words came out. Already she felt like her head was spinning.

She let go of her ‘sister’s’ hand, and headed towards the kitchen looking for something softer to drink. She was halfway there before she realised Alannah wasn’t with her, but then it was already too late and a thick crowd separated them both.

Never mind, she thought. I’m sure Alannah will be fine. It’s not like it’s the first time she’s been out of the house dressed before after all.

She staggered into the kitchen and almost got the shock of her life.

Her best friend, Beth, was in the kitchen, sprawled across the island, dressed in a princess costume, her legs spread and her high heels in the air, while someone in a Zorro costume pumped his big, hard cock deep inside of her.

Someone else was standing by her head, and pumping his cock in and out of her heavily painted lips as she proceeded to suck him off.

She was moaning, obviously enjoying herself getting taken from both ends, and between her moans, Annabelle could hear her best friend saying, “Daddy’s little princess…I’m daddy’s little princess.”

The guy at her mouth pulled out and thick, white hot streams of cum exploded all over her face and down her tits, practically exposed by the low cut of the dress she was wearing – obviously designed for someone much younger than her from the way she was quite literally squeezed into it.

As Annabelle watched, the other guy between her legs also spasmed and pulled out, spurting his hot cum all over the creamy white stockings she was wearing.

“Happy Sweet Sixteenth, baby,” the guy she had been giving a blowjob to said, and as Beth replied with, “thank-you, Daddy,” with a shock Annabelle realised her best friend had just blown her own father, while another man took her maidenhood directly in front of him.

She held her hands up to her face, as her best friend, Beth, started scooping the cum up with her fingers and then licking them clean.

Before she could think to say anything, she felt a big, strong arm slip around her shoulders.

“Looking for me?” A voice in her ear whispered and turning, Anna saw she was being accosted by someone dressed up as the Big Bad Wolf.

Her head still buzzing from the alcohol, and whatever had been in the punch, Anna sunk into his arms as he started to nuzzle her neck. Glancing down, she could see he was packing and suddenly realised just how horny seeing her best friend get fucked in front of her had made her.

Her little silk panties between her thighs were already soaking wet.

She slipped one hand down and fondled his obvious bulge.

“Hmmm…” she moaned, not sure quite what was cumming over her. “Is that for me? Oh, what a great big cock you have. What say you and me take this upstairs?”

“What’s wrong with right here?” The Big Bad wolf asked her, and lowered his face to her tits while one hand slipped between her thighs and gently opened her legs.

Behind her, Annabelle could already hear her friend, Beth, moaning again as someone bent her over and took from her behind, but Anna right then was too consumed in satisfying her own suddenly awoken carnal desires to care.

***

Alannah, meanwhile, had barely noticed her sister was gone.

She was too busy being pawed by a couple of horny guys herself and to be honest, she was actually starting to enjoy it.

She didn’t know whether it was just the drink, or the fact that she was here at what was supposed to be some kind of ‘sex party’, all dressed up in a naughty school uniform, but she was starting to love, and even crave, all the attention she was getting.

Over to her right, the party was obviously just getting started, as what looked like Beth’s mum had just got down on her knees and was currently devouring a big black cock, while someone behind her spread her legs and slipped his head under her skirt to eat her out.

Lucky gurl, Alannah thought, as the guy directly behind her slipped his hand under her pleated skirt and started fondling her arse while he slipped his tongue deep in her mouth.

Another guy in front of her was feeling her false tits, had ahold of her hand, and was using it to massage his already hard cock through his tight leather trousers.

“You want this, don’t you?” He was saying, and Alannah found herself nodding almost before she realised what she was doing. “You want my big, hard cock between your lips, don’t you, you little cocksucker?”

Alannah had never sucked cock before – though she had often found herself fantasising about it lately after Annabelle had shown her the porn she had found on their daddy’s computer – and allowed herself now to be pushed to her knees while the man in front of her presented himself to her in all his full glory.

Remembering the videos she had seen, Alannah parted her lips and took his cock full in her mouth, almost making herself gag.

After a couple of minutes though, she soon found herself developing a rhythm and from the moans coming from above, she must obviously be doing something right, she thought.

The man behind her started unbuckling his belt as he lifted her skirt.

Alannah knew what was coming next and knowing she should probably warn him, took her mouth away from the first man’s cock.

“I…I’m not a real gurl,” she moaned, blinking back tears at being found out so soon.

“That’s okay, Sweetie,” the man stood behind her said, pushing her back onto the first man’s cock, and with a shock Alannah recognised the voice of her own father. “Because I’ve always wanted to fuck a sexy sissy slut.”

He pulled up her skirt out of the way, pushed her lacy black panties to one side and after lubricating her up, slid his massive, great tool deep inside her.

For a moment there was pain as it felt like her boi-pussy was being split apart, but then the pleasure took over. She began thrusting back on the big cock inside of her, as the man in front of her continued to face-fuck her until he came.

His hot spunk spilling out over her lips, and all down her heavily made-up face,

behind her, she felt her Daddy grunt, and then suddenly he was cumming inside her too as Alannah experienced her first ever sissygasm and creamed herself in her sexy black panties.

***

When she had cleaned herself up a little bit, her Daddy’s cum still leaking from her boi-pussy, Alannah went looking for Annabelle – wondering what might have happened to her sister.

She found her in one of the other rooms, lying on her back, her legs spread and her knickers discarded, while a mature woman licked out her by now well-fucked pussy.

Another guy was feeding her his cock and sliding it between her ruby red lips, as her own hands reached up and played with her exposed tits.

She was moaning, and groaning, and obviously very close to cumming.

With a shock, Alannah recognised the woman between his sister’s thighs and realised Annabelle was being eaten out by their own mother!

Their mum had her hand between her thighs, and was shamelessly fingering her clit as she ate out her own daughter.

Alannah felt her own little bitty clitty starting to harden in her panties.

“Look’s like someone wants to join in,” someone said, and Alannah felt herself being pushed towards the scene playing out in front of her before she could even think of trying to stop what was happening.

Someone fished out her cock, slipped a condom on it, and forced her between her mum’s open thighs. Alannah felt her cock, brushing against her mother’s hot, wet pussy, and then suddenly she was up deep inside of her.

Her mother let out a loud moan as she felt herself being penetrated from behind, and Alannah was soon moaning in unison as she felt her mother’s hot wetness engulfing her slick cock. Consumed by the moment, Alannah began thrusting herself in and out of her mother’s wet snatch, even as she felt her panties being lowered and her boi-pussy being entered again from behind.

“Oh yes…yes…fuck me…fuck me harder…fuck me like the filthy little slut that I am…” Alannah moaned, and saw her sister looking up as she recognised her brother’s falsetto cry just above her.

As Alannah came inside her mother’s pussy, so too did she feel the man behind her exploding deep inside her own, gripping her hips as he filled her with his hot, wet spunk. Alannah groaned with pleasure, and looked down on her sister just as the man fucking Annabelle’s mouth pulled out and came as well – spraying his creamy spunk all over Annabelle’s lips, as well as all over their mother’s face and hair.

Lying there on the floor, fucked within an inch of her life, Annabelle looked up at her new ‘sister’ and smiled as she saw the pure ecstasy written all over her former brother’s face as he continued to fuck their motherland from behind to yet another orgasm.

All in all, Annabelle thought, so far it had been one hell of a party…and the night was only just getting started…

***

The next morning, Alan woke up with only a hazy memory of all that had happened the night before, mainly because of whatever it was that had been in that punch.

He remembered he and her sister leaving the party, after getting fucked several more times more, in a bid to try and beat their parents home; and he remembered them both getting changed and having a shower together to try and wash off some of the smell of sex on them both, but not much than that.

He guessed he must have just passed out after that.

After the events of last night, he felt weird being in boy-mode again, and doubted it would be long before he dressed up again if sex felt that good as a gurl – albeit one with something a little extra than most other girls.

Already he missed the long false eyelashes, the pigtails, and the breast forms he had grown so comfortable with last night, and though he still felt a little sore from all the action he’d seen, still there was almost an empty feeling inside of him too like he had always been born to be fucked like a gurl.

As he made his way downstairs, the taste of cum still on his breath, he could hear the moans of someone making love in the hallway as he headed towards the stairs.

Mum and dad are at it again already? He thought. Lucky dad…

He went downstairs and entered the kitchen hoping to get a drink.

As he stood there by the sink, drinking a glass of water to try and rehydrate himself, he felt his mum come up behind him, dressed in a silk robe, and wrap her arms around his torso; pressing her already erect nipples into his back.

“Did you have fun last night, Sweetie?” She asked. “You know…at the party?”

Fuck, Alan thought.

“You knew that was me and Annabelle?” He asked, spinning round to face her. She was dressed in a slinky black satin nightie under the robe, he noted, and nothing else.

She smiled at him sweetly.

“Of course we both did,” she said. “Me and your father both. It was supposed to be Beth’s cumming out party, but neither of us thought you were ready. Looks like we were wring about you both. Very wrong…”

She licked her lips seductively.

“Actually, I was kind of hoping for a repeat performance…” She started to sink to her knees, fishing out his already hardening cock from his boxer shorts as she did so. “Your father is already upstairs taking care of your sister…”

For the first time, Alan suddenly realised the sounds of two people having loud, passionate sex were still coming from upstairs, even though his mother was down here with him.

Up in her bedroom, his sister began moaning louder – obviously knowing her brother could hear her downstairs.

“Oh yes, yes, fuck me Daddy. Fuck me Daddy so hard. Oh yes, oh yes, oh yessss…”

“You should know, I think you made a very sexy gurl, and I do hope you’re going to continue to dress up as Alannah more often from now on,” his mother said, continuing as though nothing was wrong, and her husband wasn’t upstairs fucking the brains out of her daughter. “I think I almost prefer you as a gurl…”

She took his cock deep in her mouth and began sucking on it, teasing it, licking the tip like it was a lollipop. “Hmmm, I can’t wait to dress you up like a sexy little Sissy slut again…”

“Mum, please, no…this is wrong,” he said, though he didn’t really mean it. “We shouldn’t be doing this…”

She paused, and looked up at him.

“I didn’t hear you complaining last night,” she said. “Besides, sounds like your father and your sister are having fun.”

Alan could still hear his sister’s moans, even over the sound of her headboard violently pounding into the wall as her daddy continued to fuck her.

“They announced the lockdown last night,” his mum said. “As of now, we’re all confined to the same house for the foreseeable future, so we might as well all have fun with each other. And you know what they say – the family that plays together, stays together.”

She took his cock back in her mouth, just as Alan exploded his creamy load all over his mother’s face.

She was right, he thought. Might as well try and enjoy lockdown while it lasted, and if that meant him getting dressed up as a girl again…

He brought her back up from her knees, and kissed her hard on the mouth, savouring the taste of his own cum.

Maybe he could even become a gurl permanently he thought…

Author bio

Naomi Matthews is the pen name for an erotic author who has several books published on Amazon. She has a blog here: https://naomimatthews551913481.wordpress.com where she publishes stories too hot for Amazon, and can be commissioned to write a personalised story here: https://ko-fi.com/naomimatthews

She can also be found on Twitter under the username, @eroticnaomi.

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