Jennifer's New Adventure Ch. 01

Author's note: This can be read as a stand alone tale but it perhaps better enjoyed after reading Dan's Dreams Come True. Thanks too for the wonderful feedback. It makes working on these stories so rewarding. Jenniferxxx

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Dan was woken from his deep sleep by a loud knocking on the door. He stumbled out of bed, grabbing his dressing gown and pulling it tightly around him. It had been three weeks since he encountered Caroline and Suzanna, who forced him to dress as a woman and made him pose in all sorts of embarrassing ways for a cross dressing magazine. They'd given him the black teddy he wore in his final photo spread and he wore it every night since.

He really didn't need the postman to see him in all his glory, so he covered up.

"Hi there, got a special delivery for a Jennifer Taylor at this address. Can you sign?" The colour drained from Dan's face. Jennifer Taylor was the name he'd been given during the photo session. He swallowed hard, but was still surprised when his voice lifted a few octaves before settling back down.

"Yeah, she lives here. I'll take it for her." He signed and took the brown envelope.

"How the f..." His mind trailed off. He ripped open the package and found a copy of "Forced Femininity" and his, or rather Jennifer's face on the cover and a tag line trailing her appearance "The Sexy Secretary Sucks! Inside". Dan flicked it open and across twelve pages, including the centre spread was part of her night at the hands of Caroline captured in the magazine. There she was in the gorgeous skirt and jacket, the rather obvious bulge poking out in front. The appearance of Suzanna in men's clothes. The brief interaction. Jennifer's strip. Suzanne doing likewise to reveal she was dressed in identical undies. Then the horny secretary sucking off her boss, who as it turns out was a gorgeous shemale. And there, in glorious colour, Jennifer giving her first blowjob and her face and hair being splattered when Suzanna came in floods. The final picture had Jennifer's gorgeously made up face covered in cum and she was smiling. She didn't remember smiling.

It was a horny photoset and Dan couldn't help get hard. He had to admit he looked amazing and he stroked his cock through the silky material of the teddy over the memory of the night and the full colour reminder in front of him. Not unexpectedly, he suddenly blasted his cum over the front of the gorgeous, flimsy outfit.

Then he noticed the white envelope tucked at the back of the magazine where someone called Carla, a particularly rough looking tranny, was bound and gagged on the bed. The one thing that literally stood out was her pussy pole. Easily 12 inches and poking out of the side of her white French knickers. Jennifer couldn't help notice the look in her eyes and a cold flush swept through her body as she remembered how she felt when she was blackmailed into the pictures.

He ripped open the envelope. "Dear Jennifer, I hope you are well darling. I know you are currently trying to work out how I know where you live, but are you really surprised? You know this is not beyond my resources. I have a task for you which could make a good photo shoot. I could make threats and warn you how the pictures we took of you could find their way to your boss, David or your parents Rob and Sarah. But we know how much you enjoyed your little stint even though you started out fighting against it and we feel certain you'll want to do this. Call me at the number below before ten and I'll give you all the details. I KNOW I'll be hearing from you. Love Caroline xxx."

Dan felt his stomach flip. How did she know so much? He was appalled at the idea, so he scrunched up the letter and threw it in the bin. "Why would she even think I'd be interested?" he said out loud to no-one in particular. "I'm not going to do it. Why would I?" Dan sat down, breathing hard, knowing the feeling in his tummy well. This was fear and excitement. "I'm not going to do it." But he was intrigued. As Caroline knew he would be. He walked over to the table and looked again at the magazine. There was Jennifer on the cover in her sexy undies looking wonderful and pretty and vulnerable and available and horny. It had been an awful, exhilarating, tortuous, wonderful night.

"There'd be no harm in finding out what it was she wanted I suppose?" said Dan. As he dipped down to pull the letter out of the bin and began smoothing it out. He picked up his mobile and started punching in the number. It rang twice.

"Hi Jennifer, I knew you couldn't resist."

"Hi Caroline. I'm so busy with work and I have so many other commitments I was really just calling to say thanks but no thanks."

"No you weren't. You're sitting there in your sad little flat, your black teddy on, your cock stiffening with every word I say knowing that no matter what it is I ask, you'll sign up pretending you don't want to do it and loving every moment. Look let me make this simple. I named your parents to scare you because I like to do stuff like that. It makes me laugh. We got some good photo sets of you and we thought you'd like to do some more. You don't have to. You can walk away now with no consequence and we're done for ever. But you were very popular and you know you want to play. You are aching to find out what outfits I have lined up for you. You know you want to pose and be photographed and you'll carry with you the hope you'll see Suzanna because you're love that gorgeous shemale and her big cock. So, tell me right now. Are you in?"

Jennifer said nothing. "In or out. I need to know now because I have another tart lined up who is fucking desperate to take part and she'll actually pay me to do it. Now. Answer me."

Jennifer said something but it was hardly audible even to her. "What did you say?" asked Caroline.

"I'm in" she repeated.

Right. I want you shaved and ready at Liverpool Street station at 1pm. Don't bother with a bag. I'll provide everything. Someone will give you the details there and I'll see you later. Oh, two other things".

"Mmhmm" responded Jennifer.

"Bring that gorgeous pout of yours with your gorgeous eyes". Jennifer smiled feeling deeply flattered. "And from now on you call me Mistress until I tell you otherwise, got it bitch?"

"I have work today?"

"Not any more - and don't you ever address me again without calling me Mistress , got it?" Caroline sounded angry.

"Yes Mistress."

"Repeat it!"

"Yes Mistress."

Caroline hung up. Jennifer breathed heavily. She wondered what the hell she had gotten herself into. But her rampant cock poking through her silky teddy betrayed how excited she was by the idea.

Dan stood in the station, watching the clock countdown to one. He was in his usual "boy attire" of black jeans, black t-shirt and black trainers. His hands pushed deep into the pockets of his black leather jacket. He checked his watch for what was probably the tenth time in a matter of minutes.

12:57. He was told to be here by 1 and had arrived in plenty of time even though the station was clear across the city.

12:58. Dan wondered who would give him the details of where he had to go, would it be Suzanne or Caroline herself? If it wasn't, how would they recognize him? Was he getting on a train or staying in London? And the most important question, what was the interesting offer that Caroline rightly thought he'd be keen to get involved in? The tension simply added to Dan's excitement and he loved the feeling of doing something dangerous and exotic again.

12:59. Dan scanned the crowd, hoping to find a familiar face wondering if anyone knew he was there to head off somewhere and spend some time as a very sexy and incredible horny young woman. He looked around, spinning slowly wondering if he should have brought the letter with Caroline's mobile number. He suddenly realised he had called her from his phone and as he began fishing for his handset, he felt a hand on his shoulder. He spun around to see a beautiful dark-haired woman. Small and elegantly featured, she had her hair in a pony tail but she was expertly made up. As he quickly scanned her up and down, he couldn't help wondering if this was another one of Caroline's gorgeous shemale friends. She was wearing a tight black skirt, thick tights and sexy high heeled boots. Her top was covered by a light green raincoat.

She leant forward and whispered in Dan's ear. "Were you expecting to meet Caroline?" Dan swallowed hard and nodded. "I'm Evie, she asked me to hand this to you" and put a white envelope into his hand. "Good luck...oh and by the way to answer the question pinging round your head, yes I am." She flashed a devastating smile and disappeared into the crowd, turning heads and she sashayed towards the entrance.

Dan followed her with her eyes until the green raincoat was no longer visible. "Fuck, she was beautiful. Was she really a guy or was she just toying with me?" wondered Dan. He suddenly remembered the envelope and ripped it open to find two railway tickets and his second letter of the day from Caroline.

"Hello my gorgeous Jennifer, I knew you would turn up. You are in for a very sexy time. I'm so glad you didn't disappoint me. Your train leaves in fifteen minutes from platform four. You will get off at a very small station called Wilson Heath and there you will get into the black Mercedes waiting for you by the front door. It will take you to where you need to be. The journey takes about an hour so grab a newspaper and some water. Or you could even flick through the "Forced Femininity" magazine you have in the inside pocket of your coat. See you soon darling, Mistress Caroline."

Dan was a little weirded out. How she knew about the magazine was really spooky, or was he just so predictable that she could guess and scare him like that? Hadn't she said on the phone this morning she liked to do that.

Dan found the platform and settled down in the train. His mind was racing almost as fast as the train as it shot through the outskirts of London and on into the green fields beyond. He'd never heard of Wilson Heath even though his geography was pretty good. Half way through the journey, a woman walked through the train and smiled at Dan on her way to the buffet. Normally he would be flattered but now paranoia gripped him, wondering if this was another "friend" of Caroline's. Was she really a woman, was she watching him? He pushed himself back into his chair and tried to breathe deeply.

He thought back to the final scenario of the photo shoot three weeks ago. Strapped to the bed in his gorgeous black liquid silk teddy, with false boobs glued to his chest and four inch patent black leather pumps, he was allowed to pleasure himself to a climax, helped along the way by Caroline threatening to turn him into a maid, a cock hungry slut or even a bride. It made him hard he wondered if that's what lay in store. But then why drag him all the way to the countryside when she could have easily set up the dressing and the shoot at her place in London?

The train pulled in to Wilson Heath. It was a small station, no more than a platform and a walkway across the line to the line heading back to London. Dan pulled up the collar on his jacket against the light rain and made his way to the front door. Three other people got off the train but as he walked out onto the road in front of the station, a black Mercedes flashed its lights and Dan made his way over, getting into the back of the car.

"You a friend of Caroline's?" asked the driver.

Dan nodded. "How did you know what I looked like?" he asked, wondering again about the power of his very odd controller.

"Didn't. Just flashed the lights. I was told you knew there was a black Merc at the station so I guessed the right person would make their way over."

"How far do we have to go?"

"Ten minutes." Dan sat back and watched the small village quickly become countryside with only the odd, but very large and expensive house, to puncture the horizon. Soon the car indicated right and pulled into a driveway, which snaked its way through the trees for about a quarter of a mile before coming to a grand house at the top of a small hill.

"You're here" said the driver. Dan got out the car and looked at the house.

To the side sat an expensive Lexus, two Mercs, a Volkswagen 4x4 and a BMW sports car.

He let out a long low whistle. "There's some money here" he said to himself. He walked to the door and rang the bell.

Inside he heard the click of high heels on a stone floor and his chest tightened and his stomach flipped. The door opened and there stood Caroline, looking wonderful. He was surprised. In a house this size he was expecting a real life maid.

Caroline was wearing a low-cut white blouse, a tight satin skirt, black stockings and four-inch black patent leather high heel court shoes. Dan caught a whiff of her perfume and found himself stiffening. "Fuck", he thought, "why must she always dress like a fantasy?"

"Jennifer darling, so glad you made it, come in." Dan stepped in to the brightly lit but classically styled hall. Caroline kissed Dan on both cheeks. He felt her firm breasts pushed against his chest and he couldn't resist a glimpse at her cleavage. "Naughty girl" said Caroline playfully smacking Dan's bottom. He blushed furiously.

"So gorgeous, I guess you want to know what this is all about." Dan nodded. "Well I'll tell you later but you're here until tomorrow when I decide when you can go. Tonight, I need your help and I guess you'll be rewarded in some fashion. Are you smooth?" Dan nodded. Since the events of three weeks ago, there wasn't a hair on his body below the neck. It felt too lovely to go back to the hairy gorilla look.

"I want you upstairs in your room. I need you to shower and put on the outfit laid out on the bed. That'll give you some idea of the role you'll play tonight and also the tone of the shoot. I did mention pictures, so don't go all coy on me now. Do you remember how to address me?"

"Yes Mistress" said Dan throwing in a little bob which could almost pass as a curtsey.

"Oh how cute and so very sweet. You're going to love tonight. Any questions?"

"Is Suzanne here?" Caroline smiled and moved forward seductively. She ran her fingers across Dan's crotch bringing him to almost instant hardness. He closed his eyes, enjoying the sensation and the moment. Suddenly Caroline grabbed him hard by the balls.

"Listen bitch, while you are in this house, this garden, this outhouse, you call me Mistress, got it?" Dan nodded furiously. Caroline twisted, bringing tears to his eyes and a grimace to his face. "Who is here, who does what is no concern of yours you little sissy bitch, because I control you and you do what I tell you. Got it?" Dan nodded. Caroline twisted harder. "Got it bitch?"

"Yes Mistress" gasped Dan as Caroline released his cock and balls from her strong and painful grip.

"Now upstairs, shower and dress. Someone will be along to help you with your make-up."

Dan gingerly climbed the stairs, slowly cursing himself. Yes, he remembered enjoying some of the dressing and how nice Caroline had been at the end of the shoot. He'd somehow pushed to the back of his mind that she was a slightly psycho bitch who could change mood quicker than the weather.

"Why the fuck am I doing this to myself?" he asked himself. At the top of the stairs, there were about seven doors, all paneled, all closed. Dan walked down the hall, until at the very end; there was a bright pink sign which said simply "Sissy Bitch."

"This'll be me" thought Dan. He walked into the room which was bright and lovely if a little small. There was a dresser and two wardrobes. There was a door slightly ajar leading to an ensuite shower room and of course, there was a bed.

Dan's eyes opened wide when he saw what was laid out for him to wear. Sheer black tights, a tight black corset and three-inch black high heeled pumps but it was what lay beside the basics that brought a combination of fear and excitement.

"Fucking hell, she can't be serious," said Dan to no-one in particular. But she was and Dan's latest adventure was about to kick into high gear.

Dan walked out of the bathroom, his hair still damp, a towel wrapped around his chest, to be met by the sight of a gorgeous bum in tight black jeans. The owner of the bum stood up, turned and smiled. She offered her hand "Hi I'm Beth, you must be Jennifer." Dan shook her hand and nodded. "I've come to help you with your preparations for tonight. It's all very exciting isn't it?"

Beth was very young. She looked it and acted it. Dan thought she could be no more than seventeen and was slightly embarrassed to be almost naked in front of her. "I've never been to a party like the one we're having tonight. I've asked to come to one for ages but I was told I had to wait until I was older. But now I've turned 19 I can be there. It's all very exciting. My, you have very pretty eyes. You're going to look wonderful by the time I've finished with you. You have such a lovely figure too. The outfit is gorgeous. I think you'll look amazing. God this is going to be so much fun."

Dan stood amazed by this stream of consciousness from this gorgeous young woman. Beth was about five foot five with flashing dark eyes and long dark hair. She had a tight white t-shirt which showed off her tight young figure and she was barefoot, suggesting she was very comfortable in the house. Who could she be? Dan thought if he waited she would soon tell him.

"Ok sweetie, let's get you started. Want to pop up on the bed and lie on your back. Flip your towel down around your waist; we don't need to see your nasty man bits. I was told you've worn these before during your last photoshoot. I saw the one in the magazine. You looked beautiful. Isn't Suzanne gorgeous? Hard to tell she is a man with nasty man bits like you!" Beth giggled and continued. "So we'll just put on the adhesive and then pop on your new boobs. They want you to have big ones, so I want to give it ten minutes before we get you up, but you can just lie there and we can have a little girly chat."

Jennifer smiled to herself. She wasn't involved in too much chatting as this little force of nature dominated the conversation and the room. "Do you know what's going to happen tonight?" asked Beth.

Jennifer shook her head hoping she was about to find out some more.

"Me neither only I know there are a few people coming and it's going to be so much fun. Oh sweetie, are you a bit worried? You suddenly look a little bit scared."

"Well you see I've only ever been dressed in front Caroline and Suzanne and so this is a little bit awkward and being there dressed in front of others is a little bit scary. Will there be others there who are dressed?" asked Jennifer.

"On no silly, you're the star of the show! Your little photo shoot excited a lot of people and they wanted to see Jennifer in the flesh. Mum had this idea of the party and a few people have paid to be there. It's all very interesting."

"Mum?" asked Jennifer.

"Oh my god!! I rattle on too much. Please don't tell her I told you she's my mum? She'll get very upset. Promise me you won't say a word, Please Jennifer?"

Jennifer smiled "You mean Caroline is you're Mum. Wow! She doesn't look old enough to have an eighteen-year-old daughter."

"I'm nineteen" said Beth indignantly "but please don't say a word. She'd be flattered you think she looks so young but she'll get angry with me if she knows you know our family connection." Jennifer lay quietly for a moment, the breasts weighing heavy on her chest. They were easily 38" DD.

Beth traced her finger over the front of Jennifer's towel. "Tonight, is going to be a lot of fun. I'll take care of you. I'll look after you but please don't tell."

Jennifer paused long enough to make Beth sweat, the smiled. "Deal!"