Double Trouble

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Tomsparty
Tomsparty
647 Followers

'Please no,' I cry. 'She will be so angry if she has to come home early.'

Carmilla grinned. 'And I wondered what your mum would say if she saw you wearing my girls make-up, their baby-doll and...' she pointed at my groin, 'that mess!.'

I saw a horrific mental picture of mum telling her new muscle bound boyfriend.

'I'll be very good,' I say my lip trembling. 'I'm so sorry I couldn't help it.'

'I'm just not sure,' she said stroking her cheek thoughtfully, 'the girls have a party this afternoon and I can't risk you going off like some sex starved volatile cannon.'

I stare at my feet depressed as my tiny cock twitched.

'Let me think and in the meantime let's clean you up. Stand in the bath,' she said sternly.

I did as instructed and as I stood before them I felt their eyes peering into me as Carmilla washed me down with the shower attachment. I dare not move and stood stock still as she rubbed my stiffing cock with soap. She cleaned me thoroughly rubbing my shaft, cleaning my foreskin and ball sack. Soon I was sparkling clean and very aroused. She again rubbed me down like an infant and couldn't avoid seeing my stiffening cock. Tina came into the bathroom and handed Carmilla some talc which she sprinkled on my cock like salt on a dinner.

The dusty white powder had a transforming effect on my swollen member defusing its active look making it look more subdued, almost feminine. This gave Carmilla an idea.

'Perhaps you could still stay with us,' she smiles as she bends me over and talc's my bottom like a baby.

I wasn't sure what she meant but pleaded with her not to tell my mum.

I felt my relationship with mum was already under pressure as she tried to get her life back into gear. The last thing she wanted was a wayward son causing problems.

'Have you another clean pair of boxers,' she asked. She knew I hadn't.

I shook my head sadly and wanted the world to swallow me up. But this had a surprising effect on Carmilla and instead of being cross she smiled understandably. Opening the airing cupboard door she rummaged amongst the fresh laundry. She quickly found a pair of pretty panties and held them out for me invitingly.

'Hey they're mine,' Tina screams as she watched me handle the skimpy lingerie and slowly her scream becomes a giggle.

'You'll have to wear these,' Carmilla said crossly. 'Now hurry up I haven't all day.'

Scared and humiliated I meekly held up a trembling foot so that she could slip them up my leg. They felt gorgeous. I immediately noticed how soft and comfy they felt as I placed a hand on Carmilla's shoulder for balance.

I looked up to see Tina and Amy smiling.

Carmilla left the pretty panties at half mast just above my shaking knees the lace tickling my thighs. 'For safety,' she said, 'you better wear one of these,' and from out the bathroom cabinet she pulled a cotton pad similar to the brand that I'd seen in Mums bedroom.

I stood transfixed as she expertly slipped the cotton pad into my gusset and yanked the panties further up my leg. Now my filled, padded panties had a transforming effect on my groin completely masking my tiny cock . I had a feminine mound and as if to make maters worse my cock stiffened with excitement but this time under all the cotton pads my pleasure went unnoticed.

Tina pushed her way forward for a better view. She had an evil grin on her face and she waved something soft and plasticy in her hands. 'We don't want her leaking do we, mum.'

Carmilla looked at the plastic pants and nodded her head in agreement. 'Good idea. We can't be too careful he looks as if might blow.'

They all laughed heatedly

I wanted to object but all I was capable of was a tiny stamp of my foot as once again she held them open for me to step into. They weren't as bad as predicted, they only rustled slightly as I moved and where quite comfortable.

'Well done,' Carmilla said standing back slightly to admire her handiwork.

'I was right,' she said turning to the girls, 'he has got lovely, shapely legs.'

Both girls nod excitedly and I cower backwards worried what they might do next. Seconds seemed to last minutes as they all stared at me with stupid grins on their faces. The silence was eventually shattered by Amy giggling. 'Let us dress him, mum. I'm sure I've got something that would make him look pretty. Jeans just don't suit him.'

Carmilla laughed and opened her mouth to reply then thought better of it. 'You're right I'm sure you've got something that would suit him and dressed in your clothes he may calm down in that department.' she points at my cock that was barely visible under the plastic panties, feminine pads and lace panties.

I shake my head. 'No,' I say, 'I'll be fine I don't know what came of me. You're girls are quite safe I don't feel ... you know?'

'No,' Carmilla says, 'Amy has a good point, I want you to wear whatever she suggests. I'm sure they fill find something most fitting for a sissy boy like you.' She grins at Tina foolishly. 'You'll help your sister, won't you?'

Tina nods.

'You decide but I can't make up my mind as to whether a short skirt or a flowy dress is more appropriate.'

'No please', I cry. 'I'll be fine. Just let me wear my jeans and a T-shirt.'

'Nonsense I've made up my mind. Wearing your own clothes again will be a privilege that has to be earned. I want you to do exactly what Amy and Tina say. I don't want to hear any complaining or I will ring your mother and tell her how you've misbehaved. She will collect you from the station and you'll have a lot of explaining to do. Especially if still wearing my daughters panties and make-up'

I feel tears filing my eyes.

'Come now, don't be so pathetic. you've bought this on yourself. I don't want to hear you complaining. You must make the decision and then accept the consequences. You have precisely one minute to decide. What's it to be dresses or straight home?' She held out her wrist and studied her watch. 'Shall I call your mum or will you let the girls dress you?'

The minute seemed to last an hour as I considered the situation. Despite the obvious humiliation the choice was easy. I didn't want to upset my mum and her new boyfriend.

'I'll let Tina and Amy dress me.' I groan.

'Wise choice now go into Tina's bedroom and do everything they say. I will inspect you in half an hour and I don't want to see any masculinity and that includes that ...' She taps my cock with a finger.

'but... I... Err,' I stammered.

She snapped loudly. 'Do what your told... At once.'

With that she disappeared to change herself.

Alone with the two girls I looked at them sorrowfully. I felt like a condemned man going to his execution. 'You won't make me wear a skirt will you? Haven't you got some jeans I could wear?

The two girls giggled and before they had chance to reply I knew my fate.

'You heard our mother. Nothing masculine. If we don't get you looking pretty we will be in as much trouble as you. Remember what she said, no moaning.

I groan and reside to my fate. 'Lets get it over then,' I say.

Amy looked thoughtful.

'I'm thinking more along the lines of short rara skirt, tights, ankle boots and a white blouse. What do you think sis?'

Tina walked around me studying my form. 'Nice choice but I see him more in a figure flattering dress. Whatever we do he simply must show off those amazing legs.'

What followed next was a comical session of being forcibly dressed in skirts and dresses. I felt like one of their Barbie dolls as I was dressed in outfit after outfit stripped and then dressed, stripped and then dressed. I wasn't sure if they enjoyed the experience or struggled to find something that they both could agree on. There was no mistaking the girls had tremendous fun all at my humiliating expense.

Carmilla popped in a few times and was totally unfazed with the mess the Tina and Amy where creating and the length of time they took. Eventually they jointly agreed on a sexy red mini dress, black high heels and black tights. They even insisted I wore one of Tina's bras which they stuffed with some old nylons. Soon after that I was dragged downstairs to be marched in front of Carmilla. She was very delighted with my transformation inspecting every item of my outfit.

'Doesn't he look pretty?' Tina says proudly.

Carmilla nods knowingly. 'Yes the transformation from naughty boy to sweet girl is instantaneous. It's a amazing what a pretty dress and lace panties can do.'

She lifted my skirt with a finger so she could check I was still wearing the panties, plastics and pads.

'Very good indeed,' she says, '.... but I don't want you getting any delusions of grandeur. Your still a young lad in a dress until you prove me otherwise.'

I wasn't sure what she meant. What did I have to prove?

The girls grinned proudly took my trembling hand and marched me back into their bedroom the mesh of my underskirt causing the dress to sway like a church bell.

'Run along dear,' Camilla shouts, 'Be good and play but do be careful of your dress. '

I surprisingly soon became accustomed to my heels and short skirt. But rather than dull my cock it had stiffened and was protruding as a unfeminine bulge at the front of my dress. Carmilla noticed what she called my indiscretion when she checked on us and offered to remedy the problem. Her solution was straightforward. In the kitchen downstairs she made me stand before her and hold aloft my dress. She called Amy and Tina to join us so they could observe. Then in full view of the giggling sisters she pulled down my tights, plastics and panties. It was all incredibly humiliating. Wearing the flamboyant dress was one think but having my panties pulled down by this matronly woman in front of her daughters was a weird experience I didn't relish. She parked my pretty lingerie just above my knee then gently took my cock in her hand. She crouched to one side so the girls could easily see. 'Look how excited he is,' she explained slowly massaging my throbbing cock. Our sissy guest obviously likes to dress as a little girl. He obviously enjoys the soft feel of Lycra and lace. The caress of sexy panties and the pull of a bra. Do you think he likes the attention and enjoys being pretty? The girls nod excitedly. 'Now I'm going to reproduce what happened last night while we were all asleep.' She grinned and I felt like a lab rat about to be dissected and yet there was no mistaking how excited I felt. Carmilla took a small tub of cream from her pocket and her nimble hands soon worked their magic and I was spasaming in her hand on the brink of a massive orgasm.

'Look closely girls, he's almost ready.' she looked me in the eye. 'Would you like me to take you shopping and buy you your own pretty outfit. We could choose you some sexy high heels, tights, pretty dress and a beautiful bra. I should make you wear it when we meet your mum at the station so she can see what a sissy you really are. Just think you'd have to travel all the way home as her beautiful daughter.' Her words got me incredibly excited and I couldn't help but shut my eyes and moan. Quick as a flash she grabbed a tea cup that Amy past her and pumped my cock for all its worth. It didn't take long as I soon ejected a torrent of thick creamy cum into the cup. Carmilla gasped and the girls clapped as if applauding a circus act. Camilla continued to pump as if milking a farmyard cow and she slowly squeezed me dry.

'There,' she said inspecting my flaccid cock, disarmed and safe. Tina would you like to put his cock away?' Tina grinned and shuffled forward and as I held my dress high she pulled my panties back and holding my cock gently guided it into my panties followed by my plastics and tights. I dropped my skirt down and stood there motionless.

'Now look what we have here girls,' she said studying the sticky contents of the tea cup. 'This is our young mans excitement. Many men want their girlfriends to swallow this. They often do what I just did with their mouths.' The two girls shrieked then smiled at each other knowingly. Carmilla passed the cup round as if sacred wine. 'Smell it.'

One by one each girl took a sniff and wrinkled their nose. 'Who wants to try some?' She dipped a manicured finger into the cup and gave it a stir. The girls shrieked and backed off as she held aloft a dripping finger. 'No takers there's a surprise,' and so as quick as a flash drew it across my lips. I jerked backwards in surprise but I was too slow and after moistening my lips she slipped her sopping finger into my mouth.

'Good girl,' she said. 'Many people think it has medicinal properties. Now Suck it all off,' she commands.

I stand there sucking her finger watching the girls close to tears.

'Now before we do anything else I think our little sissy girl should drink all her medicine. What do you think girls?'

Both nodded their heads and so I was ceremoniously given the cup. I refused to move, my painted lips clamped shut, the salty taste of my own cum still in my mouth.

'I will count to 10 and within that time I want that cup completely empty. Otherwise I'm taking you to that station dressed as you are. One.' She snapped loudly.

Terrified I imagined the look on my mums face as she saw me standing at the platform in the pretty dress.

'Two.'

I felt my legs tremble and I stepped awkwardly in my heels rubbing my nylon covered legs together.

'Three.'

The girls looked at each other.

I lifted the cup to my lips as more tears welled up in my eye. I sipped and let my cum slid into my mouth until gone.

'Show me,' she snapped.

I showed her the tea cup. She wasn't satisfied. 'Every last drop,' she said mockingly. 'I want it completely dry.'

I upturned the cup and sucked.

'Good girl,' she said as I drained every bit, 'now go back to play as your friends will be round soon.'

I had forgotten about the supposed party but as it turned out I actually enjoyed myself. Both Any and Tina never let on as to who I really was and I got away with being one of the girls. I had a great time and after I had accepted my new role they accepted me.

Throughout the afternoon her daughters seemed fascinated with my cock. They supposedly had never seen one before and where virgins. But at their age I personally I wasn't so sure. Nevertheless Camilla decided that they may as well learn something while I stayed so on the last night I was dressed like a cheap tart in a tight leather skirt, black fishnet stockings, black high heels and a semi transparent blouse that was far too small and stretched over my padded bra. This time I was told not to wear a pad in my panties or the plastic knickers. But I didn't mind as the silky panties felt sensational.

'I thought we would sit in and watch another DVD,' Carmilla said but to my horror Carmilla had invited a young friend round. Bob seemed a nice guy a few years older than me. I thought he was a boyfriend of Tina's but it became pretty clear this wasn't the case. By now I'd worn girls clothes for two days and had become accustomed to them so I behaved quite naturally. I was even able to sit and walk without showing my panties and had even adopted lots of feminine mannerisms. I enjoyed it all.

I had no idea of Carmilla's intention when we all sat down in the lounge. Bob sat next to me. A bit too close for comfort and immediately started chatting me up. I wasn't sure if he knew who I really was but I didn't want to say anything in case he didn't. As the evening wore on he began to be quite suggestive and his hand touched my knee on more than one occasion. He talked to me as if a girl and he made me feel pretty and special. Carmilla didn't seem to worry and the girls watched the process like a show. I looked at Carmilla expecting help but she just winked and I saw a sparkle in her eyes that I'd never seen before. I tried to shuffle away and sit as demurely as possible crossing my legs away from him.

Then Carmilla said something that left me flabbergasted. 'I hope you're watching Tina and Amy. Have you seen how Bob is chatting our guest up?

They both nod enthusiastically.

'Have you seen how our guest has been flirting too. How she's been touching his arm, fingering her dress, tossing her hair and fluttering her eyes at him. This is common practice and is all part of flirting. Bob is trying to impress and our guest is trying to attract by being as feminine a possible.' They nod again and I wonder what game they're playing.

'Have you seen too how she's crossed her sexy legs away from him and her tiny toes are pointing away? They nod as if in a lesson. 'That isn't good.' She turns to me. 'For goodness sake show some enthusiasm we haven't got all night. Bobs a great guy enjoy the moment. You can be incredibly ungrateful.'

The girls laugh and Bob grins proudly.

'But, but,' I stammer. 'I don't know Bob and besides this isn't right.'

Carmilla glared at me angrily. 'Just remember your seeing your mum tomorrow and we both want her to be pleased.' A shiver ran down my spine as I imagined yet again what she and her new boyfriend would say if they could see me dressed as I was with Bob all over me.

So I do as Carmilla wants, I cross my legs and angle my body towards Bob. I let him smell my perfume, toss my hair, touch him gently on the arm and flutter my long eyelashes. I laugh at his jokes and look into his eyes as if he's the only man in the world. This has an incredible effect on him. And he's over me like a rash, his hands sliding over my body like a ravenous octopus. His arms curled round my waist and the back of my neck. I felt trapped as he pulled me towards his lips. I felt the growth on his chin prickle my soft skin, then his dry lips press against mine. He gave me a kiss and I remained motionless.

Carmilla wasn't pleased. 'Show some response, Bobs a nice guy but he's not renown for his patience.'

So I kiss him back and before I know it his tongue is deep inside my mouth probing the back of the throat. Then in horror I feel my cock jerk and stiffen. I'm concerned that my arousal will be noticed but Carmilla was more interested in the huge bulge in Bobs trousers.

Tina got off the sofa and sat so Bob could spread out. Carmilla dims the lights and Amy puts on some sensual music on the CD player.

Bob took total control, he roughly pushed me on to the cushions.

'l'm going to fuck you like the sissy slut you are.' he growls.

This surprises me. I see a change in his character and panic. I try to get up but Bob seems impossibly strong and dressed in my feminine attire I feel incredibly weak and vulnerable as his hands slid up my slender legs.

'Help,' I mumble but neither Carmilla or the girls say anything.

In the background I could just make out Carmilla excitedly giving a running commentary to her girls as if watching a horse race.

Carmilla was giving sex education lessons via a live demonstration.

Bob enthusiastically ran his hands all over my soft body paying attention to my padded bra and my silky covered buttocks. His breathing quickened and he began to get very excited. Now I found my whole body tingle as a desire swept through me too. I loved wearing the dress, I loved being a woman and wanted to take it further. I offered little resistance as he expertly flipped me over like a pancake so my head was buried in the cushions and my butt stuck upward proudly. He ran his hands over my skirt feeling my stockings and suspenders under the tightly stretched material.

'I'm going to fuck you until you're eyes water,' he groans and I hear the sound of his trouser zipper rasp downwards.

Up until this moment I believed that this was all a game and Bob would never carry out his threats but as his hands slid my skirt up over my peachy backside I began to have my doubts. I wanted to shout and scream but I was paralysed. I heard excited gasps from the girls as he roughly pulled my panties down and ran his tongue all over my arse. Frantically he tore my skimpy panties off my legs and held them to his nose before stuffing them in my mouth like a gag. They where slightly damp. My cock was dribbling with excitement.

Tomsparty
Tomsparty
647 Followers