The Birthday Surprise

Teddy nervously looked around as his friends laughed loudly and pushed him past the shabby nondescript door and into the darkened corridor beyond where a woman was waiting. They had all been out celebrating Teddy's 25th birthday, an event which Teddy if he was truly being listened to would have said he hadn't really wanted to happen, but his friends had insisted and as always Teddy meekly went along with whatever the group wanted to do. On the rambling walk home after having spent the evening bouncing from one salubrious pub to another and then to an Indian restaurant for a boozy meal they had sprung on Teddy the revelation of his surprise present.

It was no secret amongst them that Teddy had not yet lost his virginity, a result of an admission made after drinking too many tequila shots at a strip club, when the subject inevitably came up again and again and the question was asked as to why he was still a virgin Teddy had always given a rote response, he had not met the right person, he wanted it to be special and that no, he wasn't gay despite their constant innuendo.

Teddy was of course telling the truth, but not the whole truth, there was also two other reasons that he simply couldn't mention, the first was that Teddy really struggled to even talk to women, especially ones he felt were attractive or were very confident in themselves, whenever he tried to talk to them he always ended up getting all tongue tied and embarrassed. He had never really got past a first date with a woman let alone get into a position where sex was even on the cards. But he couldn't tell his friends that, even if they had been an understanding bunch, which they weren't and if even if they were he just wasn't even sure how to even tell somebody about it. The other reason, the second and probably biggest thing was that Teddy was a crossdresser and very firmly in the closet about it.

Since an early age he'd been secretly wearing his sister's and then his mother's clothes and ever since he'd moved out and started living alone he'd been buying his own feminine clothes and lingerie, but he still acted as though he was hiding that part of himself as if he were still living with other people. So he would only dress late at night and only in his bedroom and all his clothes were stashed in a locked suitcase kept on top of the wardrobe under boxes full of odds and ends. He'd watched porn that often involved crossdressers having sex with other men but whilst he found it titillating and exciting to watch he'd never really thought of himself in a woman's role, he was in his mind very firmly straight and only attracted to woman, not of course that he had any joy in that area.

Thinking back as he was pushed towards the door Teddy recalled that as the night of his birthday approached his friends would laugh and joke together and not tell him what was so funny, now as the stood outside the door the thing they were laughing about had finally been shared. They had arranged and paid for a prostitute to take his cherry, not any prostitute one friend drunkenly announced, but an expensive, high class one who had come highly recommended, he didn't say who it was that had recommended her, bur Teddy was fairly certain at least one of his friends was already well aware of her.

Despite Teddy's weak protestations his friends told him it was time and as everything had been arranged, the woman would be eagerly waiting for him and the final piece of information was that they were now standing right outside her place at that exact moment. One friend walked to a nearby door and pressed the buzzer, announced that Teddy the birthday boy had arrived and after a few seconds the door opened.

Pushed through the door with the voices of his friends calling out crude words of encouragement and telling him that they'd expect a blow by blow account in the morning Teddy saw a slightly stern looking woman staring at him in the dimly lit hallway.

'Shut the door Teddy' she ordered.

Obeying Teddy turned and pushed the door shut on his friends who he could see were already walking away laughing and joking with each other.

The locks on the door clicked shut automatically locking him in with the woman.

'Good, now come with me.'

Teddy turned to see her moving away down the corridor, a door opened and she was bathed in light as she stepped in to the room.

Teddy followed after her and entered the small room, it was sparsely furnished with just an armchair, a settee and a large television which was switched off. There were a couple of landscapes on the white walls but other than that the room was empty.

The woman was sitting in the armchair and Teddy could now see her clearly. She had dark brown hair tied up in a ponytail, bright green eyes and her mouth was a tight slash of red lipstick. She had a frown on her face as she looked at Teddy as though she didn't much like what she saw. She was wearing a black silk robe that was secured tightly and only revealed the fact that she was wearing either black stockings or tights with a pair of strappy black stilettoes.

'My name is Cassandra and you Teddy I gather, are a virgin and you don't want to be one anymore.'

Teddy stuttered at her bluntness, unable to speak.

'Well what is it?' Cassandra snapped.

Teddy shrugged 'My friends, they.. uh, they organised this, I..'

She nodded her head 'I see.'

'So why are you a virgin, are you not attracted to women or is it that you are attracted to men perhaps or is it something else that has stopped you?'

Teddy just stood there gazing at Cassandra, there was no she was beautiful and definitely very confident and in control, and as happened with every woman he met once again he was struggling to put together a coherent sentence.

Cassandra took his silence as an admittance of some deeper reason behind his virginity 'So it's some kink you have that has been stopping you, well lucky for you I am just the sort of person willing and able to explore that kink with.'

Teddy continued to just stand there in utter silence, his mouth slightly open in shock.

Cassandra continued 'So, is it spanking, being tied up, tying someone up, domination, pet play, pee play, sounding, pegging, enforced chastity, infantilism, crossdressing, sissification?'

Teddy just listened as she listed off all the kinks, some he had heard of and some he hadn't, but as soon as she mentioned crossdressing he couldn't help but blush and look at the floor.

Cassandra leapt on the immediate clue 'Ah, so crossdressing, so is that it? are you a girly boy, do you like to wear pretty lingerie and pretend to be a woman?'

Teddy, desperate to keep his secret stuttered 'I, no, it's.'

Sighing Cassandra softened her voice 'It's ok Teddy, this is a safe place to experiment with your little kink and I have just the thing for you here and I know you are just going to love it.'

Cassandra stood up and smoothed down her robe, brushing past Teddy she walked out of the room. 'Follow me Teddy bear.'

Without really thinking Teddy followed Cassandra out of the room and as he reached the corridor he could see her walking up the stairs at the far end, her hips swaying hypnotically.

Teddy followed up the stairs, through an open door and into a brightly lit room. The room was dominated by a large double bed covered with a red velvet bedspread and he could see his reflection in the mirrored doors the covered the far wall.

Cassandra waiting for him to enter walked behind him and shut the door.

'Right my Teddy bear' she said 'first things first, take off your clothes and while you're doing that I'll find something sexy for you to wear.'

Teddy opened his mouth in an O and was about to say something when Cassandra tutted and reached out a finger and put it over his lips.

'No talking for now, just doing.'

Teddy had no real choice but to obey, his lack of confidence and experience with women just wouldn't allow him to protest and try to lie himself out of this situation.

Slowly he took off his clothes and lay them on the bed.

As he did so Cassandra bustled around in the wardrobes behind the mirrored doors and laid items of clothing on the bed.

After undressing Teddy stood in just his underpants and watched nervously, hands clasped in front of his groin.

With her back to him Cassandra asked his shoe size.

'Eight' Teddy mumbled in reply.

Cassandra turned around holding a pair of chunky black heels 'These'll do then.'

Seeing he was still wearing his underpants Cassandra shook her head 'Everything dear, that means those horrid panties as well. Then we can get you into something much sexier and befitting of my newest girl toy.'

She smiled at Teddy and motioned with her hand at his groin 'off they pop'

Teddy gulped and slowly shimmied his underpants down, stepped out of them and put them on top of his clothes, turning he caught Cassandra's gaze at his groin and he immediately held his hands over his crotch.

Cassandra grinned 'There's not that much there to hide is there?'

Teddy blushed and bowed his head.

'Aw so sweet, my little girl is embarrassed by her tiny clitty.' Cassandra laughed.

'Well you can cover it up now.' Cassandra picked up a pair of silky black panties and held them out towards Teddy.

Stretching out a hand Teddy took the panties from her outstretched hand. They were soft and cool to the touch, he could see that whilst the front was soft black silk the rear panels were made of stretchy lace which would leave his bottom visible beneath the pattern.

'Don't just look at them, put them on.' Cassandra prodded.

Teddy nodded and lowering them down to his ankles he stepped into them.

As he pulled them up his legs the material brushed against his skin in a manner that Teddy had always found arousing.

As he settled the panties around his slightly stiffening penis Cassandra sighed.

'Very pretty, it's lucky you're blonde so your body hair is almost invisible, you really should shave everywhere though, before the next time.'

Teddy looked at the woman quizzically at that comment.

Cassandra saw his look and smiled, seemingly to Teddy just a little menacingly.

'Oh I can promise you that after tonight you will be changed forever and will be back as often as I need you.'

As though a switch went off suddenly Cassandra's face was all lightness and smiles 'stockings next, sit on the bed and roll them up into a ball and then over your legs, you know what to do.'

Cassandra handed Teddy two red hold up stockings, he sat on the bed and followed her instructions, rolling the so familiar silky smooth material up and over each leg.

Once he had finished smoothing the stockings down, something Teddy had always enjoyed doing in the privacy of his own room Cassandra moved around the bed and stood in front of him.

'Arms behind your back please.'

Teddy obeyed and she sprayed his chest with an aerosol can. Tossing the can onto the bed Cassandra reached behind Teddy and pulled a small box into view. She took out a flesh coloured lump of plastic and pushed it firmly against his chest.

'Put your left hand over it Teddy and push down.'

As Teddy did so she repeated the action on the other side of his chest and then told him to hold it with his right hand.

She walked out of sight and Teddy sat there holding what he realised were breast forms to his chest, something he had always promised himself to buy but had never got around to, satisfying his need for false breasts by filling his bras with a couple of rolled up socks.

After a few moments Cassandra told him to let go and as he did Teddy felt the weight of the boobs pulling at the skin on his chest the glue holding them firmly in place.

Reappearing in front of him Cassandra told him to hold his arms out straight forwards and when he did so she slipped a black bra over his arms and leaned in close to secure the strap on his back. As she did so Teddy could smell her heavy flowery perfume, closing his eyes Teddy sighed and he heard Cassandra chuckle.

'You're loving this aren't you' she whispered and Teddy couldn't help but whisper 'yes' back.

Stepping back Cassandra looked him up and down.

'Not a bad base to work from, it's lucky you have a slightly girly figure and feminine face. I'd put you in a corset but I don't think we need to go that far tonight, but maybe some other time.'

She motioned for Teddy to stand up.

'Next step, make up and lots of it for your debut tonight.'

Cassandra walked over to the make-up table and made Teddy sit on the stool with his back to the mirror, facing the door where he wasn't able to see himself in the mirrored wardrobes without having to turn his head either. The only thing he could really look at was hanging from the door, a pink silk robe with little red and white flowers embroidered on it that he thought was very cute that made him want to buy something similar for himself.

Teddy was broken from his little reverie by Cassandra 'no trying to peek in mirrors until I say, ok?'

Teddy nodded his head unable at that moment to say anything, he then sat in silence as Cassandra opened a procession of jars and began to apply make-up to his face. He closed his eyes when ordered so she could apply eyeshadow, fluttered his false eyelashes after she stuck them to his eyelids and winced as she plucked errant hairs from his eyebrows with a pair of tweezers. Teddy worried that might be going a bit too far but just couldn't muster the courage to say anything to Cassandra, he was finding her far too intimidating to be anything other than passive and compliant in her presence.

Leaving Teddy to sit on the stool to allow his second coating of lip gloss to dry Cassandra moved back to the mirrored wardrobes and after a few moments returned holding a wig with long auburn hair. She carefully positioned it on his head then took a small bottle from the table, unscrewed the lid and withdrew the dropper. Lifting the edge of the wig with her free hand she ran the dropper along it and then pressed it down onto Teddy's scalp.

'We don't want your hair falling off at an inopportune moment now do we?'

Teddy looked at Cassandra but didn't reply, he didn't think she even wanted him to.

'Stand up and remember, no peeking so look straight ahead.'

Teddy stood up and looked at the door with the silk robe hanging off it.

He felt Cassandra's hands holding something up to his midriff and when he looked down he could see she had slipped a skimpy red bustier around him, he could feel her pulling it tight, causing Teddy to pull his stomach in. Then she started to close the fasteners at his back and Teddy struggled to breathe out fully. Looking down he could see it barely covered his black bra and the breast forms were very visible and apparent.

The next thing Teddy knew was Cassandra telling him to lift up his feet and he stepped into the black leather skirt which she pulled up his legs and settled over his hips. The skirt was incredibly short and only just covered his groin, Teddy could imagine that if he bent over nothing would be left to anyone's imagination.

Cassandra walked back in front of him and smiled.

'Hold out your left hand.'

Teddy obeyed and Cassandra fastened a bracelet around his wrist, it was made of black leather but had the word Slut picked out in rhinestones on it. She then put her hand in the pocket of her robe and pulled out a chain. Holding it out if front of him Teddy could see that hanging in the middle of the silver links was again the word Slut, but on either side the links to the chain were shaped like erect penises.

Cassandra held it to his neck and fastened it. Teddy could feel it tight against the flesh of his neck.

Cassandra smiled as she looked Teddy up and down 'you need just one more thing to be perfect, a name and a slutty one at that.'

She tapped a finger against her lip as she pondered 'We can't call you Teddy with an i, that's not really slutty or girly enough.'

'I think, Kari might suit you, yes, you can be Kari, and she spelt it out to Teddy 'K A R I.'

'Turn around Kari, look at yourself in the mirrors.'

Teddy was shocked at his renaming, he had always thought of himself as Maddy when he dressed, but Maddy was quite conservative, he had never dressed in clothes like this before and Kari seemed to fit this feminine version of himself more than Maddy ever would.

Turning Teddy looked across the room. Initially he saw a woman standing next to the smiling Cassandra. She looked like a total slut, her eyes were surrounded by dark black eyeshadow and had long lashes thick with mascara, her lips were fat with bright red glossy lipstick and her clothing seemed to expose more flesh than they hid. The red bustier she was wearing made it obvious she was not a real woman by pushing up the fake looking breasts. Teddy blinked his makeup caked eyelids and when he looked again saw himself, dressed like a slut.

Cassandra stroked a hand on Teddy's shoulder. 'So what do you think Kari, do you like what you see?'

Teddy swallowed and started to reply 'Uhm...' but was interrupted when Cassandra held a hand to his crotch.

'I think you do, judging by your reaction.'

Teddy hadn't noticed but now was well aware of his stiff and erect penis straining at the silk panties and moaned as Cassandra gave it a squeeze.

'Perhaps we should do something about that, would you like me to play with your clitty Kari?'

Teddy moaned again as she rubbed her hand against his now painfully stiff cock.

Moving closer Cassandra backed Teddy up to the bed and pushed him backwards so he flopped onto the bed.

Teddy could only lay there looking up at the gorgeous woman looming above him.

'Wait there a second Kari.' She said and disappeared out of view for a few seconds.

'Now hold your arms up over your head and pull your wrists close together.'

Teddy did as he was told and felt something metal clip around one wrist and then the other. Cassandra then gave him a tug and pulled him slightly higher up the bed, Teddy wriggled his bottom as his body moved across the bed, the satin material of his panties rubbing against his hard cock, Teddy moaned quietly and realised that Cassandra was a lot stronger than she looked.

There was another click and Cassandra reappeared in his eyeline.

'There, now even if you are tempted your hands cannot wander.' Teddy tried to pull his arms down but he had been securely handcuffed to the headboard.

Telling him to raise up his head and shoulders Cassandra pushed a pillow underneath Teddy so he was no longer lying flat.

She then moved down the side of the bed and lifted up Teddy's skirt, pulled his panties down his legs, slipped one hole over his shoe but left the other where it was so they were hanging off one shoe.

'A very slutty image' Cassandra commented.

His penis now freed from the silk panties had sprung upright and Cassandra gave a little snort of what seemed to be derision as she looked at it, then produced a condom from her robe pocket, opened the packet and slipped it over the erect member.

She gave it one gentle stroke and Teddy shuddered.

What happened next shocked Teddy, from out of his sight she pulled a large black dildo, it was at least 8 inches long and had a large flared helmet that glinted in the light of the room. She held it up in front of him.

'Do you like what you see Kari, isn't it beautiful?'

Teddy was speechless at the sight of the dildo, what was happening now was way beyond anything he had ever done in his life before and more like some of the porn he had watched online.

Cassandra smiled at Teddy 'I would like you to kiss it for me.'

She held the tip close to his mouth and the long black shaft filled his vision.

No wanting to kiss it and unable to speak Teddy shook his head.

'I promise Kari, that you'll like it.' As she spoke she gave his penis a couple of strokes, making Teddy groan, then she moved the tip closer and gently brushed it against his lips.

'Kiss it for me Kari, I know you really want to.'

Teddy shook his head again.

Cassandra's hand moved down the shaft of his penis until they enveloped his balls then she squeezed, Teddy squealed at the sudden pain 'Just one little kiss Kari' she said angrily 'and I'll play with your clitty some more, I know that's what you'd prefer.' She gave Teddy's balls another squeeze, not so hard this time but the implication was obvious.

Teddy groaned as the pain receded, he really wanted Cassandra to continue to play with his cock and not to squeeze his balls again and he knew there was only one way to get her to continue with the pleasurable option.

Giving in Teddy pursed his lips, leant forwards and gave the tip a very small peck.

'Oh that was a pathetic kiss' Cassandra spat 'kiss it properly Kari.'

Teddy sighed and gave it what he thought was a proper kiss.

He was rewarded by Cassandra's hand returning to his penis and as she began once more to gently stroke it up and down she said.

'Good girl, now give it a lick Kari.'

Teddy knew he couldn't really refuse after kissing it so he stuck out his tongue and licked the head.

'Good, girl, again.'

Teddy licked it again.

'Keep licking Kari.'

As Teddy licked the dildo Cassandra continued to rub his cock up and down, at the same time she moved the dildo about so he was not only licking at the head but also the shaft.

Then as he opened his mouth to lick along the shaft Cassandra moved quickly and pushed the dildo fully into his mouth, Teddy spluttered and tried to force it out with his tongue but Cassandra held it firmly in his mouth, dribble ran down his chin and Cassandra pushed it gently deeper and then slowly pulled it out, dragging the shaft over Teddy's glossy lips.

'Good girl' she laughed 'I knew you'd like sucking on a cock.' Teddy gagged as Cassandra pushed it deep into his mouth again and he swallowed what felt like gallons of saliva.

As her hand moved up and down his penis at a faster pace Teddy moaned, the sound muffled by the dildo moving in and out of his open mouth.

Suddenly Cassandra let go of Teddy's penis and removed the dildo from his mouth, Teddy lay there gasping for air, his cock twitching and on the verge of cumming.

Cassandra leaned in close to Teddy's face as though she was going to kiss him, but at the last moment his head fell back as she ripped the pillow from beneath him.

He felt his lower half being lifted up and then the pillow slipped underneath his bottom, lifting him up. Cassandra threw his legs wide open and Teddy felt something pressing at the opening of his anus, the pressure increased and he gasped as he felt what could only be the spit covered dildo slip inside. There was a brief burning sensation as more and more of thick plastic dildo was pushed inside him. The sensation of being filled by the black dildo was strange at first to Teddy but as Cassandra slowly pulled it back out, living the tip still inside and then pushed it back in again Teddy began to sort of enjoy the sensation of fullness that it brought and he couldn't help but let out a soft moan.

As if that moan was her cue Cassandra began to thrust the dildo in and out at a quicker pace and with each thrust it seemed to get deeper and deeper.

Despite his shock at what was happening Teddy was unable to contain his moans of pleasure as the dildo began to massage his prostrate and automatically he began to move his body in time to her thrusts.

'You like that don't you Kari?' Cassandra asked as she pushed the dildo deep inside Teddy then slid it back out again.

Teddy moaned 'yes' as Cassandra thrust the dildo faster and harder into his body.

'Tell me how much you want it Kari.'

Teddy couldn't help himself; he was so aroused that he was starting to push his body down as Cassandra pushed the dildo into his body 'I want it so much Cassandra.'

Cassandra pulled the dildo all the way out of Teddy 'Beg me Kari, beg me to fuck you with this dildo, tell me how much you want it, how much you want cock.'

Teddy didn't want her to stop.

'Please, fuck me, please, I want your cock so much it hurts, please.'

Teddy groaned in sudden frustration as Cassandra slid the dildo all the way out and then began to gently rub the tip against Teddy's rosebud without entering him.

'Not bad Kari, but I'm not sure I believe you, tell me how badly you want this cock, what will you do for it?'

Teddy looked along down his body at Cassandra positioned between his widely spread legs and begged, more than anything at that moment he wanted the dildo back inside him and with eyes wide open and fixed on Cassandra's he moaned and begged 'please, I want it in me so badly, I'll do anything you ask, please, please, I need it, I need that cock in me.'

'Anything eh, will you suck a real cock for me, will you let a real man fuck you?'

Teddy didn't even think, he just responded 'yes, yes anything, please, anything.'

Cassandra looked at him with a twisted smile on her lips 'Tell me, convince me you want a real man.'

Something at that moment unlocked inside Teddy and he began to say things he had never even dreamt off before 'Please, I want to suck a real cock, be fucked by a real man, please I want it so badly, please.'

Cassandra smiled 'Tell me you want to suck a real man's cock again.'

'Teddy moaned 'Yes I want to; I want to suck a real cock.'

'And swallow his juicy cum?'

Teddy nodded. 'Yes, yes and swallow his juicy cum.'

'Cassandra smiled at Teddy 'I knew you'd be a good girl Kari and good girls always get their rewards.'

She pushed the dildo all the way up inside Teddy 'Keep begging me for it Kari.'

'Oh please Cassandra, fuck me with your cock, fuck me.'

Cassandra pushed the cock in and out of Teddy with one hand with the other she took hold of his straining penis and began to stroke it slowly increasing the speed until Teddys hips were jerking up and down as Cassandra tugged on his cock.

'Tell me what you would do with a real man's cock Kari.'

Teddy's arousal continued to build and between moans of pleasure he told Cassandra that he would suck the cock, lick it all over and kiss the tip.

'Kari, will you take his cum in your mouth and swill it around your mouth before swallowing it down?'

'Teddy groaned 'Yes, yes I will.'

With one final thrust the damn inside Teddy broke and his cock spasmed beneath Cassandra's hand as he filled the condom with his cum.

Teddy's head slumped back onto the bed and he stared up at the ceiling.

Cassandra let go of the dildo, leaving it wedged up inside Teddy and muttered 'Good girl Kari, good girl.'

She took hold of the tip of the condom and pulled carefully until there was enough slack to pinch off the top filled with Teddy's seed then removed it entirely.

The next thing Teddy knew there was a weight on the bed beside him and Cassandra was looming into view.

'Good girls get rewards.' she said and dangled the full condom over his face.

Teddy's eyes opened wide, shocked at what was expected now.

Cassandra lifted the condom up and held the open end over his mouth.

'Open wide Kari.'

Teddy could see the sperm moving down inside the condom as though in slow motion, without even knowing why he opened his mouth and stuck out his tongue.

'Oh good girl.' Cassandra cooed at his initiative.

'Teddy blushed slightly under the thick make up at her praise and tasted the salty liquid as it dripped onto the tip of his tongue.

It then began to run down the top of his tongue into his mouth, Cassandra took hold of the condom with both hands and squeezed every drop out into his waiting mouth.

For Teddy the taste of the slightly warm cum wasn't particularly pleasant but it wasn't horrible either and he let it slide down his throat.

As he closed his mouth Cassandra screwed up the condom in one hand and gave his lips a quick wipe with a finger, which she then licked.

'Mmm, tastes good doesn't it?'

Teddy simply nodded.

Cassandra stood up and looked down at Teddy 'Stay there Kari, I'll be back in a few minutes.'

Teddy heard the door open, then shut and he was left alone, still handcuffed to the bed.

Teddy lay on the bed, he licked his lips and tasted the remnants of the cum, his cum that Cassandra had forced into his mouth from the condom he had filled as she fucked him with the dildo. He had been laying there now for what felt like at least half an hour and was starting to feel uncomfortable, the handcuffs were biting at his wrists and his shoulders ached. His lower back was starting to complain about the position he was in with his bum up in the air on the pillow and the dildo still wedged in his backside, so he wriggled until he had pushed the pillow away with his buttocks, this had the effect of making the dildo shift and move which sent pulses of pleasure through his body, Teddy moaned and then as the pillow moved free he groaned loudly as the dildo was pushed deeper inside as it connected with the harder mattress, his limp cock sprang back to life and Teddy could not help but start to grind his buttocks against the mattress to prolong the sensations running through his body.

Before he could really get going Teddy heard the door opening and a smiling Cassandra reappeared in his line of sight.

'Hey Kari, sorry I was so long, but I had a couple of things I had to do.'

There was a sudden emptiness in his bottom as he felt the dildo being removed Teddy couldn't help but moan in frustration and then he Cassandra loomed over him as she unlocked the handcuffs so he was finally able to sit up and look at Cassandra, she was now wearing a short black skirt, thigh length boots and he could see a white blouse peeking out from a partially done up black leather jacket.

'Put your knickers on Kari' she ordered 'I know you are a slut, but even sluts should at least have some standards.'

Teddy moved off the bed and bent down to pull up his panties, once they were up he smoothed out his skirt and looked back at Cassandra who was grinning at him oddly.

'I have something I want you to see.'

She held out a tablet and on it he could see a picture of the room he was in and on the bed he could see himself, overlaid was a large white arrow, a play button.

'Press play Kari.'

With great trepidation Teddy reached out and pressed the arrow to make the video play.

What followed was a video of edited highlights of his transformation and then of him writhing on the bed, close up of him sucking on the dildo, being fucked with it and him begging to be suck a real cock and to be fucked as well. When it finished he gazed around the room with a hunted look, but couldn't see the cameras that were obviously there somewhere.

Teddy flopped down onto the bed, utterly shocked and feeling oddly betrayed, tears filled his eyes 'What, what do you want, money?' he asked.

Cassandra laughed 'yes, but also no, not in the way you are thinking Kari.'

'Then, what.'

'I want you to work for me Kari, I'll take you out tonight, you can do what you begged to do and earn me some money while you do it.'

Teddy looked at Cassandra, his mouth open.

She waved the tablet in the air 'I think it goes without saying that if you don't then everybody you know will see this video.'

Teddy started to shake, terrified at what was happening and what might happen if he didn't comply with Cassandra's order.

'Kari?'

Teddy looked up to see Cassandra standing in front of him.

'I know this is what you want, why deny it.'

'I. I. I don't, I'm not, I can't.'

Cassandra slapped Teddy 'For fuck's sake Kari, get a grip of yourself, you know this is what you really want, I'm just opening that door so you can actually do it.'

Teddy held his hand to his cheek and just stared at Cassandra as she stood up, he wondered whether she doing this out of some twisted idea of altruism and actually trying to help him.' Teddy just sat there trying to get his head around the fact that he was being blackmailed but might also sort of being helped by this woman.'

'Get up Kari.' Cassand ordered breaking Teddy out of his thoughts.

Teddy stood up still holding his cheek.

'Right, pay attention.'

'You'll charge twenty for a hand job, thirty for oral, thirty five for oral without a condom and fifty for anal.'

Teddy swallowed, he was sure he could never, would never go so far as to let someone fuck him, even though Cassandra had done just that with her dildo.

'I want you to make me at least two fifty by the end of the night, or else.'

'I can't, I could never.' Teddy began.

'Shut the fuck up, you will do as I say or everyone will know you are a cock worshipping crossdressing whore.' Cassandra shouted at him.

Wincing at her harsh voice Teddy dropped his head, the long auburn hair of his wig falling around his makeup covered face.

'Now come with me Kari, time's wasting.'

Cassandra stormed out of the room and Teddy seemingly unable to muster the will to disobey meekly followed.

Teddy slowly walked down the stairs holding on to the banister for dear life as his feet wobbled in heels that were far higher than anything he had ever worn before.

As he reached the ground floor he looked up from watching his feet to see Cassandra standing by the front door waiting.

There was a tight smile on her lips 'Don't worry you'll soon get used to those heels; you'll get plenty of practice walking in them tonight.'

Teddy walked towards her; each time he took a small tentative step he could feel the erotically charged sensation of the tops of his nylon covered thighs brushing together.

As he reached Cassandra she held out a small clutch bag.

'Here, there's a few things inside you're going to need, condoms, lube, wet wipes and some lipstick.'

Teddy looked at the purse and then took it without saying a word. Cassandra then turned her back to him, opened the door and stepped outside.

As Teddy stood in the doorway, terrified not only of being outside dressed as a woman but also of the slim possibility his friends might still be around. As he waited there unable to move Cassandra turned back to him, tutted, grabbed the top of his bustier and pulled him forwards, Teddy had no choice but to totter out of the house.

Cassandra kept pulling until he was well clear of the door and then pushed past him, pulled the door shut and locked it.

Teddy looked anxiously around, there was no one in sight on the dark street but it didn't make him feel any happier to know that he hadn't been seen.

As he looked around Cassandra walked past.

'Come on Kari, it's not a long walk.'

Cassandra set off down the path and Teddy looking back at the locked door had no real option but to follow her out onto the streets.

The cool night air blew over Teddy's body as he hustled to catch Cassandra up, it made him realise how slightly dressed he was, it wasn't particularly cold but his exposed flesh was getting goose bumps. He looked at Cassandra, certain that although she was wearing a short skirt and stockings, the black leather jacket was keeping her much warmer than he currently was.

As he looked at her enviously Cassandra walked out into the road and crossed the street, Teddy followed. They walked up a few more dimly lit streets, most of the houses on either side had no lights on but one or two were well lit and Teddy hunched his shoulder and put his face down as they passed just in case anyone was looking.

As they passed one particularly large and well-lit house Cassandra hissed at him.

'Stop that Kari, if you want people to look at and wonder about you that's just the way to act. Stand up straight and be confident, no one will give you a second glance, look as if you're meant to be here.'

Teddy straightened up and kept walking, it didn't help his nerves at all, he was still scared of being recognised, by who he couldn't have said but the fear was still there all the same.

Eventually they came to the corner of a long well-lit road, despite the lateness of the hour a few cars still moved up and down it. There were no other people about though.

'Well Kari, here we are, your patch for the night, time to start earning me some money.'

Teddy was like a rat caught in a trap, in the back of his mind he had thought that maybe Cassandra was just going to walk him around and then reveal it was all just a bit of fun. But no she was deadly serious.

Teddy looked around, suddenly finally a small portion of defiance loomed up in him and he shook his head 'I can't do this, I'm, I'm not a prostitute, I'm a man.'

Cassandra stared at Teddy and hissed 'Kari, you don't look or act like one do you?' she took a step closer to Teddy 'you will be whatever I tell you to be and do whatever I tell you to do, after all you did promise to do whatever I wanted' Cassandra grabbed hold of his chin, yanking his face so she could stare straight into his eyes 'Do you understand?'

Teddy blinked and tried to avoid her gaze, he was pretty sure he understood, but he was definitely feeling conflicted, he didn't want to be outside dressed like this but also he didn't want to admit there was a part of himself that was revelling in everything that had happened to him tonight.

Moving even closer Casandra hissed again 'remember Kari, I have all your clothes, your phone, your wallet and your keys, all back at mine, I know your old name, who your friends are and where you live. If you don't want them to see you begging me for a real cock dressed as a whore then you will do this tonight and incidentally any other night I tell you your services are required.'

'Now Kari, do you understand?'

Teddy nodded as the realisation came crashing down on him, he was totally under Cassandra's control unless he wanted the world to know about his crossdressing and everything that had happened this evening.

'Answer me Kari.'

Teddy nodded 'Yes Cassandra, I understand.'

'Good girl Kari, now go make me some money, she waved her hand up the road.

'Walk up to the end of the road and then back, keep doing it till you someone stops.'

Teddy looked up the road and then back at Cassandra.

'Go' Cassandra almost shouted.

Teddy began to quickly walk away from Cassandra his heels clacking on the pavement. The cool night air blew against his legs and up his short skirt where it caused his penis to shrivel even further, shivering now he wrapped his arms about his body beneath his false breasts and kept walking.

As he walked up the road cars sped past, one or two slowed and Teddy's heart began to beat faster at the possibility one might stop, but none did.

Reaching the end of the road he turned, almost losing his balance in the unfamiliar heels and began to walk back towards Cassandra who he could see smoking a cigarette in the distance.

A short toot on a car horn made him jump and he looked to his side to see a car had stopped next to him.

The window rolled down and a voice from inside asked 'How much?'

Teddy walked closer and stuttered '20 for a hand job.'

'Is that it, don't waste my time.' the man responded.

Teddy hesitated, he had no choice in the matter, at only 20 a time he would have to give hand jobs to at least 13 men before the night was done and it didn't seem likely that many men, like this one would be interested in just that. As he looked into the shadowy car Teddy was in utter confusion, if he didn't make the money Cassandra wanted by the end of the night somehow everyone he knew would see him dressed like this, being fucked and sucking on a dildo, begging for the opportunity to be with a real man, like the one sitting in this car right now. Whilst his life would not be ruined, he knew life might get unpleasant and then the light in the car came on. Teddy's eyes caught those of the driver and instinctively he looked down only for his averted gaze to catch sight of the large bulge in the man's beige chinos.

At that moment for the first time this night Teddy finally made a decision for himself, taking a deep breath he placed his hands on the window frame and leaned in close, unable to hide his desire he said in a sultry voice 'I can do more if you want.'

The man looked over from the driver's seat and looked Teddy up and down 'What's your name?'

Teddy no longer cared that he might have been forced into this position, he had decided he wanted to do this, more than anything else he had ever wanted he wanted to try to give this man pleasure and by so doing receive pleasure himself.

'Kari' Teddy said it's Kari.'

Well Kari, so what more will you do and how much will it cost?'

Kari licked her lips and reeled off the prices Cassandra had given her, then as the man pulled cash out of his wallet and proffered him a fifty pound note Kari grinned as she realised that she would be losing her virginity tonight, just not the way her friends had intended.