First Transsexual

Note from Bookbuddy: This series of tails filed under Novel follows a group of like mind people who join forces to create a world where sex and love are separate worlds. They build a community focused on bringing all forms of sexual activity to those pursuing it for pleasure without shame.

New readers, I recommend starting at chapter 1 to understand the characters and background. Everyone else, thanks for continuing to support this tale.

------------------------------------------------------------------------------------------------------------------------

First there was the text, frightening in itself. June had passed on Dave's contact details to Dennis's mum. Great, he was going to wear the wrath of their voyeur's mum. She would probably make a deal of them messing with his phone and stealing his porn, especially him and his mum, going at it.

The phone vibrated on the desk, unknown caller. His stomach knotted, his throat dried. He knew who it was alright. Should he answer this call? He finally flicked the green handset icon to answer.

The voice responding to his bland greeting surprised him with a deep, warm feminine tone, soft and mildly sexy. No sound of the rage he'd expected.

"Is this David Stapleton." she asked

"Yes, who's asking."

"This is Madeleine Palinski. I think we need to talk; we have a sensitive matter we need to discuss."

"Do we need to talk about it now I'm kinda busy at work?" He replied, looking at an empty desk with a blank screen.

Madeleine suggested they meet at a Coffee Club just down the road, she would see him there at twelve-fifteen. She has red hair, wearing a red top and is carrying a red handbag. Screwed she's power dressing, he described his clothes before hanging up.

Two days ago Dave and his friends had been disturbed in their apartment by a Voyeur, peering in the window watching them have sex, while filming it in one hand and pulling his dick in the other hand. A rumble had occurred as a result and Dennis the Voyeur had been punished by the flatmates and we had lifted all his homemade porn from his phone. June had left a video message for Dennis's mum Madeleine Palinski saying they need to talk, and now Dave faced that ugly prospect.

Queuing to order behind Madeleine, a creeping sickness filled David's stomach, pushing his appetite away, gurgling like a spar and producing more and more gas sitting uncomfortably in his bowel. How to release without noise, fear of their conversation taking over his insides. Just a little release and test if it would make a noise. Ah it didn't great, oh no rotten eggs. Dave looked behind, blaming the rest of the queue. Madeleine didn't seem to notice. At least that's a blessing.

He fiddled with his chicken wrap as if poisoned. Certain a tirade of abuse would engulf him, he struggled to start the conversation. Dave needn't have worried. It started in a way that floored him.

Madeleine's warm, smiling voice eased his mind. "Was that you? What a stink, I nearly puked."

Dave grinned at her and responded. "Yes, sorry, it was a ripper, wasn't."

Her demeanour changed, her voice shaking as if her confidence was draining. "It's me who has to apologise for my son's intrusion into your privacy with his fucking smartphone. Honestly, I don't know where he gets his ideas from sometimes."

Dave thought carefully before replying and tried to answer in a stern schoolmaster's voice. God knows he had heard plenty of them in his high school days, and what a cheek she had been the one to introduce him to most things. "His behaviour was upsetting to my flatmate and her friend. Still, it's over now and I hope he learnt a lesson."

Some of her playfulness returned as she took in what Dave said. "Thanks for not calling the cops. It embarrassed him to lose the videos of your neighbours playing up. He thought I would be furious. I had warned him time and time again that he'd be in serious trouble if ever caught filming like that. He just didn't listen."

"No harm done. Actually June, my girlfriend, would like him to return. He has a fantastic eye with the camera and well other benefits."

Madeleines' full playfulness returned. "I understand what she is saying. I don't know where that monster came from. He certainly didn't get it from his dad. He's the opposite. Did she have to beat his nuts so hard; he is still bruised and swollen, I can't do anything......."

She trailed off as she realised she had overstepped the mark with a stranger.

"Madeleine..." Dave started.

"Call me Maddie. It's like being back at a school when you call me Madeleine."

"Maddie, we know what you and your son do. We have no problem with that. Having sex for the sheer pleasure of it is what we all do in our world. It's separate from our emotional bonds. If they coincide from time to time, then that's even better, but you should not avoid one, because you don't have the other."

"Interesting philosophy, so you're in a swingers' club, is that what you are saying?"

"No, you miss the point. We see it as a lifestyle choice. We live together, love together and play together. We at the same time are building a small internet porn presence. It won't make much money, but it gives us a commercial focus."

Maddie studied Dave as he spoke, responding with. "If you are making films and stuff, I assume you need a beautician, then?"

"Um, not sure I would have to consult with June."

"You need to consult her for everything then?" She was quick to follow up.

"We make joint decisions, and she would understand what a beautician does better than I, and therefore know if it's something useful for our group."

She smiled at Dave and reached across the table for his hand and said to him. "Why don't I take you to my studio and show you what we do. I have some spare time for an hour."

Dave couldn't believe this exciting but scary invitation. "I love to take you up on that. I need to contact the office to make an excuse. "He said with little further thought.

"Good, that's settled. Finish your wrap and let's go."

His stomach was doing its thing again, as they entered the short arcade that held Maddie's studio, but this time with an exciting gurgle, rather than one of fear. She unlocked and unbolted the enormous glass sliding door. Dave noticed she didn't change the sign that right now read Open on the inside and "Away for 30 minutes" on the outside.

Amongst the shelves of product were mirrors showing them walking through the variety of chairs and trays towards the back of the saloon, his nostrils enjoying the aromas of a hair studio. To the left cubicles created with the curtains, the gaps revealing ambulance style gurney beds. They passed three before coming to a more substantial looking closed room and then into an alcove end the end of the shop. This space acted as a kitchen and a makeshift office, a fridge, sink and two desks occupied the small room.

Maddie hadn't stopped talking since entering the shop. He barely took any notice of her, his focus on the services list, the bottom line - Brazilian Waxing. The conversation with June came back to him. He told her and Poppy needed a waxing to tidy up their pubic region. Dave could do with something like that if he was to be in the movies.

".......and then of course there is the waxing studio." She finished looking at Dave.

Curiosity caught him. Those last words "Waxing studio, where do you do that?"

"Through that door, there's a private soundproof room, it's obvious if you're getting your bits waxed you're going to be naked and make noise, some clients are quite vocal." Madeline spoke as someone who knew her business very well.

"How much?" Waxing would be gold for Dave's group, but it could be pricey.

"Why? Do you want one? For you it would be free." She smiled, looking him straight in the eyes.

"Yeah thanks, I was thinking you know for June and stuff."

"If I join you guys, I'd do it as my contribution, you know." She was still smiling at me.

Dave scratched my head out of nervousness, not from any itch or anything, his mind turning over at a rapid rate, trying to take this in.

"Why don't you do me now, I can talk to June tonight and show her the result." Then, as an afterthought. "It won't take long, will it?"

"About an hour, get in here, get your gear off and have a shower, I'll find Tranny, she's free for a while she can help."

"Who's Tranny."

Maddie opened the door to the private room, inside eating a lunch wrap a woman sat her in the back of her straight black page boy cut facing us, she turned removing a chicken wrap from her long olive face, putting her thin fingers and small palm over her mouth to cover her chewing.

"Sorry Tranny, this is Dave, he's a friend of mine and we're going to wax his bits."

Pointing to the shower in the back right-hand corner, Tranny fluttered her perfect lashes, her brown eyes glinted, she parted her bright red lips to speak. "Fantastic, Mr Dave, why don't get your gear off and pop into the shower while I finish this, and get the room organised."

"Dave, I assume you want the experience filmed for June and the crew to watch?" Maddie asked with an impish grin on her face.

"I suppose so. Do I have a choice?" I replied.

"Well, you do, but it'll give her a good idea of what I can do. Perhaps how it might work at your place?"

Maddie slide open a door at the side of the table to reveal a camera and then walked to down by the shower and did the same to a shelf over a sink. Two fixed cameras were now on the bed, with one on the ceiling. She turned on a monitor and colour pictures of the room lit up broken into three of the screen four quadrants.

"Come on, gear off, into the shower." Maddie urged. "Don't be shy we'll know those bits as well as your most rampant lover soon."

A mixture of fear and arousal washed through his body as he climbed naked into the shower, leaving Tranny folding and stacking his clothes like an attendant mother with her ten your old boy. Once finished, Dave dried his front with Tranny drying his back.

"Mr Dave face down, bum up." Tranny spoke softly. She had taken off her blue strapped dress, replacing it with a white coat, unbuttoned at the neck to nearly the middle of the breasts, leaving very little to the imagination.

He moved into position. She lightly powdered his backside, crack, and the top of my ball sack. She surprised him by applying a lubricant to his anus., before he could ask, she told him.

"Mr Dave, I am going to slip a small appliance into your anus with a bevel at the top. This will protect you from getting wax on it, which would hurt a lot." and then, as an afterthought, in an impish tone. "Hopefully you might even like this part."

She slipped the device partly in, withdrawing it and then pushing it back several times. Oddly, his dick expressed pleasure from this action. Mr Stiffy is coming back, June would say. Where was this taking him? Maddie's two rubber-gloved fingers lightly pushed his foreskin, uncovering his knob and hiding beneath the hood. She dabbed a little lube on the tip, continuing to move the foreskin back and forth. With a dildo in his arse, Maddie stroking his knob. He had never had this kind of strange feeling before, waxing his cock is turning out to be fun.

Tranny applied some other liquid to the backside and around the crack, then took out an oblong shape bottle like a square roll-on. One bum cheek covered with the contents, she then pressed a light cotton strip over the patch before ripping it off.

"Oh, fuck." involuntary utterance.

Maddie leaned over his ear with her hand still working his cock, the lack of bra covering her breasts obvious as they warmly caressed his back. "If you're lucky, that might come later. This big boy is definitely ready for action."

Dave's mind was in overdrive, waxing now, going on rhythmically, Tranny working the crack and top of the balls. She asked him to roll over and repeated the process on his front, around the thighs, across the top of the penis. Dave was stinging all over, except for Mr Stiffy, who was doing him proud today. Tranny came to the cock. Maddie bent down, took the knob in her mouth, and swirled her tongue around it before withdrawing and leaving Tranny to complete her work.

The phone rang in the shop. Maddie quickly left the room, leaving Dave to Tranny and the last perhaps most, painful part of the exercise. His eyes closed. He didn't want to know when the pain would come. He had no reason to fear she was good at her job and although he had lots of stings; the job completed quickly.

She clearing her stuff away; she came back to him, swallowing his dick and working the plug in his arse; fantastic. Eyes closed in pleasure, the softness of her mouth and unusual movements in his anus. He knew fulfilling June's requirement for him to be buggered before she allowed him to do the same to others was going to be no problem. She had said he should be fully bisexual if they honestly intended to continue. He had this thought as Tranny lifted her mouth to his penis, while continuing to work the plug.

"Mr Dave, I have not been entirely honest with you." Tranny's voice wavering a little as she looked down. "Mr Dave, I don't want you to panic some people do when they find out."

"Tranny what's the matter." Concerned for her, he thought she was going to tell him she was married, had Aids or something. He had really wanted to fuck this lady, and she was showing all the signs of wanting it to.

"Mr Dave, I'm Lady Boy, you understand, titties up top and man bits down below."

"Fuck, I'm sorry" Mr Stiffy was shrinking to Mr Floppy Dave felt awkward. The smells and noises in the room became more prominent. It suddenly occurred to him that this would meet June's edict, that he and other males needed to be bisexual. He thought to himself, why don't I at least try it. "Show us your bits then, bring them here so I can touch."

"Mr Dave, you sure you want to see? I'm ashamed you might laugh at Tranny."

"Of course, don't be afraid this could be educational and fun." He realised why she or he was called Tranny, of course, transsexual.

Tranny moved around the bed, positioning his face at her crotch level. She started unbuttoning her white coat, letting it fall to the floor, underneath a perfect pair of breasts, and a pair of white panties, which seemed rather full of something. As the underwear slipped down, she revealed a small but very definite penis strapped up backwards, pushing her testicles to the side and disappearing into her crack. She pulled on something while reaching around to reveal a device that looked like a butt plug with a rope on. It appeared between her legs, attached to her now engorging penis. It wasn't the smallest dick he had seen, but it was on the smallish size. Dave reached and held it in his hand, stroking it as Maddie had his, moving the foreskin backwards and forwards over the head. The silky smoothness of the skin surprised him, as did the ease of rubbing him or her, watching Tranny reach for his mimicking Dave's actions.

"Mr Dave, you want to fuck me or me fuck you." Tranny's brown eyes looking into mine.

Dave swallowed. This was it, the moment June wanted for him. It's a pity she wasn't here. "Tranny you must go first, be gentle I'm a virgin you know."

"Mr Dave, thank you I am very gentle for your first time." She moved away to a side bench, opened a drawer and took out some condoms, expertly opened it and popped it over her dick, covering it in a lubricant. She removed the plug from Dave's anus again, put a generous amount of lubricant around the entrance. Asking him to push back, she forced her stiff into the anus.

The sensation different to the plug, wider and more giving. She just pushed the head slightly in, then withdrew, repeating the action over and over, each time penetrating a little more. It wasn't unpleasant, but it also didn't seem that erogenous either. His bowels screaming to take an enormous shit, Tranny kept all of that at bay by constantly stroking Dave's cock with well-lubed fingers. The penetrating strokes went deeper with each thrust until the point of her testicles were slapping his arse, the experience thrilling. She stepped up the pace, her waste thrusting faster and harder, her attention to his cock lapsing, sweat dripping down her face between her furiously bouncing breasts, her face contorting in concentration before and enormous thrust followed by a gentle more rhythmic follow-up stroke. With a sigh, she reached over, sucking his cock into her lips to arouse it.

The door open, and Maddie was standing in it, the outside world in sight for a second, everything suddenly exposed and wrong.

"What the fuck Tranny, no need to answer that I can see what you're fucking." Maddie appeared disappointed and angry at the scene before her.

"Sorry Miss Maddie, we got carried away and I..." Tranny tried to explain.

"Get your Thai arse back into the studio, you have a nails appointment in a couple of minutes, take off the rubber and put those dirty butt plugs in the sink, lab coat on and out of here."

"Sorry Miss Maddie, can I have my panties back." Implored Tranny.

"No, you don't need knickers. You got it out, you can leave it out, I'll consider them later. Now go."

Tranny left the room, still buttoning up her lab coat. Maddie stepped in and closed the door, and looked at the still naked Dave on the bed. Dave hung his head and looked at his feet. This was like being a small child, having being caught doing something very wrong. She had taken command.

"I'm sorry about this Dave, this was not my plan. I was coming back in to give you the rogering of a lifetime. Now I just feel flat. Whatever made you let Tranny fuck your arse; I never saw that coming." She was searching for some understanding.

"June said for our little group to survive and grow, we had to experience everything without prejudices. I had never had sex with a man, and it just seemed like an ideal opportunity. "

She smiled at him. He could see her relaxing again. "Well, you certainly did June proud, and I have it all on tape. I'll shut that down now and grab the files. You hop in the shower, wipe your bum well, who knows where that nasty little Thai's bits have been. We can then talk about when I get you to myself and I can visit your group, or should I say June's group."

Maddy went to the laptop on the bench. Reaching in the drawer, she pulled out a USB stick and started the copying process while Dave showered, washing his now hairless reproductive area.

"When are you free and can get away from your hubby?"

"Oh Jason, he's a truckie, drives the long haul, goes away days at a time, often weeks. He left this morning and won't be back 'til Tuesday next week. I've plenty of time."

Dave climbed out of the shower. Maddie grabbed a towel and dried him down, taking time and care around his newly clean bits. She handed him his clothes one at a time and when dressed; she put her arms around him, grabbed his face, put her tongue in his mouth and kissed him long and hard. She felt down his trousers to where Mr Stiffy had made a reappearance.

"You, my boy, are going to get fucked 'til it hurts in the next four days, so get out of here. I have a studio to run. Take your USB for June, and I'll see you after closing tonight. We work a couple hours later on Friday night. I'll be there around seven thirty and I'll bring my toothbrush and not much else."

"Look forward to it."

"I hope this June is as liberal as you say, hey and take these, a souvenir from your first anal." She chucked me Tranny's white panties as he left the room.