The Moulding of a Transvestite

The Moulding of a Transvestite

Preface.

We have a mature bisexual cross-dresser with a very submissive side, by day he is David, post office worker. By night and weekends, he turns into 'Jak' a classy T-Gurl, she has arranged to meet a mature bisexual assertive male.

This is a full account by Jak, a mature bisexual male transvestite of the first meeting with a mature bisexual assertive male she met online via Skype video chat. The meeting is set for Friday evening, it is now Thursday evening.

Geoff is coolly excited and is already mulling over how the date will go. Jak, of course is very excited at the prospect of the meeting, but full of trepidation at her impending fate.

It all starts in Geoff's living room, where they are both chatting to each other via the Skype chat program.

Chapter One: The First Meeting.

Jak, a classy mature bisexual male transvestite, sat in the Hotel bar awaiting her date she was a little early, but that was Jak to a tee. As she sat on the bar stool sipping her glass of wine, a party of males in the bar sat transfixed at her long shapely legs that run from her short black skirt down into the very stylish four-inch black high heels, her whole aura oozed, class 'A' T-Gurl, that knew how to dress to please but also how to attract attention.

At 8 o'clock that evening, precisely, Geoff entered the bar, a tall, suave, sophisticated person, they had chatted many times on an internet chat room message service and Jak had impressed him so much he wanted to meet at the earliest opportunity. Jak had sent many pictures of herself but refused to see any of him, as she liked the air of excitement not knowing what to expect.

He could tell it was Jak at the bar from her pictures, he walked up behind her then with her concentration on the wine glass he bent slightly forward and whispered close to her ear

'Hi Jak' Geoff said 'You look even more stunning than your pictures'

She knew it was Geoff and whispered back,

'Thank you' and nervously smiled.

Geoff placed his hands on her waist and kissed the right side of her neck it was as if they were lovers just meeting in a bar. Geoff ordered a bottle of champagne and they moved to a quiet secluded booth in the bar just far enough away from everyone and inquisitive eyes, so they could get to know each other better.

Geoff handed her a wrapped gift box that he had in his suit pocket, as she opened it he pulled her close to him. Inside was a gold anklet with an inscribed name on it, it just said SLAVE. She lifted her leg as he took it from the box and attached it around her right ankle Jak kissed him passionately on the lips, it was her turn to give him a gift, she opened her handbag and removed a small wrapped box and Geoff took it with a grin on his face.

'Is it what I think it is Jak', Geoff asked

'Yes' she whispered softly 'and it's ready to go'. Geoff removed the small remote control from the box and smiled as he gently pushed the small slider up and watched as Jak's face changed expression and her hands grasped his thigh

'Oh, baby not too high please, please' she pleaded, what she had handed Geoff was the remote control to the electronic balls she had placed deep inside her girly pussy earlier in her room.

Geoff rose and went to the bar to collect the champagne and glasses, upon his return he sat opposite her so that he could watch her more closely as he played with the control he had placed in his pocket. She never knew when it was going to go high or low, she just had to sit there as he played with her, but for her part, she also knew he had sat in that position for a reason. She kicked off the shoe where Geoff had just placed her new anklet and run her foot against his leg, then up to his knee and then along the inside of his thigh until she could feel his swelling cock beneath his trouser crotch. She pushed her toes deeper into him as he turned up the power of the remote, it was just a question of who would cum first, and Geoff caressed her foot and knew that he needed to have this woman and have her soon, not even bothering to finish their drinks he said it was time to leave. She pulled on her heel and rose straightening her little black mini skirt, as she did. Geoff could see her curves and thought how fortunate he had been to happen upon such a sexy looking girl.

Geoff, instantly attracted by her smile, it was a look that would make you melt, such a happy go lucky face, so sweet and innocent but Geoff had learned more about Jak of the following weeks that told him otherwise. Jak picked up her bag and coat and walked towards the exit as she did so Geoff placed his hand on her lower back just on the edge of her cute bum and guided her to through the doors.

Outside it was just getting dusk and Geoff directed Jak over to his car in the car park, he unlocked the car remotely, opened the passenger door for Jak, as she crouched forwards, and backed in towards the seat. Geoff moved the slider up a touch and a bolt shot through Jak as she lost control and slumped back into the sports car seat gripping the sides as she did, the feeling was indescribable and Geoff laughed as he said

'I so wanted to do that inside but knew it would be to the public' he informed her 'you are mine tonight Jak and I intend to play with you how I like'.

Jak's facial expression changed to the 'knowing smile' that he had fallen for, climbing into the driving seat he half turned and reached between her legs for the seat adjuster and moved her seat back as far as it would go. Reclining her seat so far that all she could see was the roof lining, her whole body was tingling with expectation as Geoff opened the glove box and removed some items she pulled her hands forwards and attached a pair of handcuffs to each wrist. As he did so, he leant over her, planted his lips upon hers, and with his probing tongue explored her soft lips and mouth. Jak loved this attention and kissed him back very deeply their tongues playing games with each other, whilst his mouth was playing one game his hands were playing another. He put his right arm under Jak's knees, lifted her legs up high exposing her soft smooth thighs to the cool night air, and with a break from her mouth lubricated a small buttplug he had removed from the glove box.

Jak knew what was expected and made her pussy more accessible as he pulled her thong to one side and put the tip on her outer lips.

Geoff smiled and mouth the words 'I love you' and she smiled back. He pushed the plug straight in and Jak winced and bucked slightly until her pussy had adjusted to the new plug. Which forced the balls still inside her deep up her tubes; Geoff lowered her legs and helped her adjust then attached the seat belt making her safe, gunning the engine he pulled out of the car park and onto the dark country road.

He had well-laid plans for that exploration.

***

It had only been just over two hours since Jak had arrived at the Hotel and checked in, once inside the room she runs a bath and opened her suitcase to examine the dilemma, what to wear. She carefully placed her choice on the bed and climbed into the bath. She needed to make sure her skin was soft and smooth for Geoff and although having just waxed days before she didn't want to make a mistake so run the razor over her legs and body for good measure. She climbed from the bath and dried her delicate skin applying just enough body lotion to soften even more but not too much as to make her body slippery besides she wanted Geoff to be able to hold onto her. Having painted her toe and fingernails Jak made up her face and hoped that he would like what he saw pulling on her wig and making that famous smile into the mirror.

Jak hoped he would be very pleased, with pearl earrings and necklace, she started to dress first putting on her white suspender belt and then rolling on tan seamed stockings, the stockings followed the contours of her leg and made her calves stand out. Teamed with a white bra, panties and a pair of falsies, Jak pulled on her white blouse and black mini skirt, to finish with, her black four-inch peep toed sling backs lifted her to almost 6 feet in height. A match for any tall guy, and the final touch being a spray of Hermes perfume around her neck and on her wrists, she was just about to put the bottle down and thought, yes, a spray under her skirt and on her thighs, just in case.

Having finished her dressing and jewelry there was just one more thing to do before going down to the bar to await her date and that was to push her present deep into her pussy, and then wait for Geoff's reaction at his present.

Maybe life would never be the same.

***

The dark country road passed easily the sleek bonnet of the car gliding through the night, Jak's gasps continued as he controlled the electrical impulse and he knew what he had to do. On the way to their meet, he had passed a busy woodland layby; he wondered how busy this would be now. Jak expected a dash to the hotel and was surprised when the car indicated and pulled into the graveled parking lot, her mind raced remembering much they had talked about, after 2 months, she wanted his dominance but perplexed by this distraction.

As the car drew to a halt, questions in her mind were about to reach her lips when the car stopped. Geoff leant across and gently caressed her lips with his, her questions disappeared as his hand slid over her leg and under her skirt, her response was immediate and she parted her legs for him. She was hoping her clitty would not divert his hands he as slowly touched the top of her thigh and moving her thong aside, slid out her plug. She awaited his fingers, but they did not come, questions in her mind grew again, this made no sense, he must know she was his, but why was he getting out of the car, the engine ran, what was happening?

As the electronic roof glided open, the night air surrounded her, the darkness engulfed her fear of blackness began to build up in her mind, surely Geoff remembered her anxiety in the dark, did he care so little for her that he wished only to scare her.

The disappointment in someone she had grown to feel so fond of drifted into her mind as the passenger door opened, she could see him crouched before her, He lifted her legs out of the foot well, her heels crunching the gravel, his hand took a long time guiding her legs out and she knew he enjoyed the touch. She heard him whisper but over the idle of the engine and the buzz of the roof struggled for clarity, as she was about to ask a question. Her ankles, opened as she, pulled roughly forward, her skirt had risen at the move, perched on the side of the seat she suddenly became aware of how exposed she was. Geoff Pushed back, his hand entered her, a fist so soon, his inexperience in this concerned her. A fist and balls? had he no respect for her limitations, but as his fingers gently entered her and removed the balls, slowly one by one, she felt his ring against her inside, shuddered at what that meant, at how he had disregarded everything, in order to spend time with her.

With the balls moist in his hand, he quickly grabbed her by the handcuff chain and stood her erect, her beauty that had engulfed him from the start was clear and his desire for her grew with every second, his hardness was unlike anything he could recall for a long time. These feelings of wanton desire had been in him for several months and he wanted her so badly.

The purr of the engine and the sound of gravel beneath their feet seemed to add to the excitement of the scenario that had played out earlier in his mind. He pushed her against the car door and pressed his hardness and his tongue against her, her cuffed hands made for his zipper, as she quickly found his release he had quickly leant forward and produced a dog lead from the car, which looked worn and seemed much more than it should be. Holding him in her hand, she felt his wetness on her palm, she so wanted Geoff's cock as much as he so clearly wanted her.

As she thought ahead, she knew he longed to feel her mouth on him, so as she began to crouch down, she quickly felt cold metal being pulled over her head, she looked up puzzled as he said 'collared and leashed'.

The rough, cold choker chain was about her neck and she could feel him pull on her, why so cruel? When it was clear he so wanted her, but a thrill of excitement raced through her, she knew that cruelty and passion lay within him, but felt so close to him, her trust was total. However, this in her mind seemed a pointless distraction. His pace was at least one ahead of her before the choker bit and she had to walk.

He walked her slowly around the purring car and the thrill of being on a dog leash in such a public way began to take over her, the balls, the plug, his fingers seemed so recent, she could still feel their imprint in her. He walked her round and round, the choker had settled nicely, she had his pace and as the night air engulfed them, she enjoyed the front, the headlamps were lovely to her eyes, the side was dark but thrilling, and she had lost herself in the situation and was happy to let Geoff take her wherever this went.

Geoff knew using his own dog collar and the lead would add to her excitement, the power he felt from parading this beautiful creature was unsurpassed and he wondered at what stage to take the bitch. When to own this T-Girl Jak, who had so captured his mind, his cock stood to erect her touch still there, leaving a lasting impression, three, four times they circled the car.

Until on the fifth passing, he pushed her quickly onto the long sleek, warm hood of the car, he heard her gasp as he pulled the dog lead over the windshield and tied it to the wooden steering wheel.

Her body, as a result, of his actions lay straight on the hood, her neck and head back against the wipers. He stood back and watched the sexiest bonnet mascot ever; he noted her toes struggling to touch the ground, her moans of pleasure and anticipation echoing across the quiet parkland he slackened the chain and her body slid slightly down the hood.

He stood between her legs and looked at this beautiful creature before him, he noticed her clitty had become exposed, with his warm hands he covered her dignity, and lifted her calves in his hands, his rough manly hands, the warmth of her stockinged legs excited him. Her legs straightened against his shoulders, his cock was hard and entered her with ease, she gasped at this, the first feel of his cock, she so wanted him as she knew he wanted her, but he stopped and they both looked at one another before his slow rhythm started. The collar cold around her neck made it difficult for her to look down and see what he was doing. Her cuffed hands, because of his body's closeness against her, meant she could not slide her hands between them; all she could feel was his cock.

Geoff did not want Jak to take his entire length of cock that was for another time, but he wanted her to know what it felt like and he wanted to feel the silky warmth of her pussy before he would totally abuse it. The warm soft silky eel was too engrossing and Geoff was lost for a second in heaven, but he must stick to his plan, a plan that had taken careful organising and preparation.

Geoff leaned forwards over Jak, her legs high in the air, the cold air against her thighs and he whispered very gently 'Jak my darling you will not be receiving me cum now; that is for later I have other plans for you and any form of disapproval will be dealt with severely' she nodded I knowingly,

She relaxed as Geoff pulled his cock out of her pussy slowly and affectionately, releasing the leash he helped her stand but turned her to face the car bonnet then pushed the small of her back towards the car, she knew what he wanted and obeyed immediately lying face down on the car.

Geoff reached into the rear of the car and pulled out a small holdall, which he unzipped; he pulled out a ball gag and proceeded to attach it to her mouth and head. He undid the cuffs that held her hands at the front and re-snapped then so her arms were around the back. The dog lead was arranged so the leash trailed down the back and tied to the cuffs keeping her in complete trust of him, any weight in her hands was felt around her neck so she had to concentrate on holding her arms up,

Geoff then snapped a leg cuff around each of her slim ankles careful not to damage the anklet he had given her earlier. The chair between was about two and a half feet long which was good for him as he put a foot on the inside of each of her feet and then spread her legs wide. She wondered what else could she be in for, she did not have to wait long as Geoff lifted her skirt up and over her pert bottom cheeks then he pulled the tiny thong strip that run over her pussy out and over the side of her left cheek.

Was he going to fuck her again? no, he put a small amount of lube on his fingers and then pushed in his index finger working it slowly back and forth and rotating as he did, with this motion going so well he slide another alongside and for a few moments stretched her pussy a bit more.

She knew that it would not stop there and she was not disappointed as the third then fourth fingers pushed her soft pussy lips farther and farther apart, but was he going to complete the feat and push his whole fist in just as she had asked him to do so many times when they chatted on-line.

Geoff kept up the rhythmic motion of pushing in and out, as he applied a little more lube and as he did, her body moved with his hand, she wanted him to be inside her. She wanted to be his toy to use; she needed him to have his pleasure.

Geoff took the small bottle of poppers from his pocket and with one hand undid the lid then held it forwards to her nose, had he made her take a very, very large hit. Her mind started to rush as the poppers hit the spot her heart started to race faster her mind whizzing along she felt her pussy relaxing as the force and motion became so much easier, it was time.

Geoff placed his thumb alongside his four fingers and with one good push stretched her pussy lips nice and wide enough to get Geoff's fist inside her wonderful warm silky pussy. He had done it.

His excitement was beyond any he had had before and he almost missed the whimpers and sighs that she let out from behind the ball gag in her mouth, he gave her another hit of poppers and waited the few seconds to let them take hold then pushed in even deeper up and past his wrist he had made it. Weeks earlier in an online chat, Geoff had told her that his first fisting of her was to be a deep one that he wanted her on his hand up and past the wrist and that's what he had accomplished.

Jak's head was rolling her body trembling and riding his hand as he pushed deeper in then withdrew almost to the knuckles then ploughed back in she was his and he knew it. Geoff fucked Jak's pussy for a few minutes but knew he had to pull out as he had much more pressing engagements with her and needed to move his location

Geoff pushed the bottle of poppers under her nose once again and whispered for her to take a long hit as he was going to pull out of her pussy. She used her teeth to grip the ball gag as she took down one last hit of poppers and readied herself for him. She was there; Geoff knew it was time to slide his hand out. As he withdrew from her, her pussy lips run along his wrist until they reached his widest point this was going to be the part that she loved, the sensation of her pussy stretched to its maximum. His knuckles past the outer ring and then his slender fingers slipped from her tight hole, it was as though her pussy almost winked at him as the fingers left her and with a very slight glisson of lube on his hand, he knew he had released from her.

No time to reflect on his triumph, he wiped his hands over her bum cheeks and straightened her panties then pulling her skirt hem down he pulled her from her position on the bonnet and around to the passenger door. Opening it, he turned her, helped her into the seat, and attached the seat belt.