Undercover Angel Ch. 03

"Yes?" she called hoping she wouldn't have to go to the door.

"Conductor ma'am; I just need she your ticket please," she recognised the voice of the conductor who had helped her to her sleeping compartment.

She pushed her slowly deflating penis one side of her crotch, holding it there with the tight gusset of her pantyhose so that the bulge was not so obvious and stood up and opened the door.

The conductor smiled his cheeky smile.

"I just need to punch your ticket," he grinned at the double entendre.

Michele smiled back and then turned her back to the conductor and rummaged in the side pocket of her briefcase. Again she felt the conductor's eyes sliding over her legs and arse. This time she found the attention arousing and forced herself to stop fantasising so that her slowly deflating erection would not harden again.

She turned around quickly and caught the conductor looking wantonly at her body as she thrust the tickets out to him. He quickly snapped his eyes back to hers but then glanced down quickly to the front of her skirt. He smiled again and when he took the tickets from her he slid one of his fingers along hers. He was openly flirting with her now.

He checked her ticket against some papers on his clipboard and eventually gave them back to her. He looked at the recently opened bottle of scotch on the small table.

"Having a party hey?" he grinned.

"Party for one," Michele replied abruptly; she realised that flirting with this man was the last thing she needed to do.

"Well if you need anything at all just press the service button," he smiled again and his eyes flicked down to her groin and then back to her eyes.

"Just think of me as the man who will service you should you need it."

He was being blatantly sexually suggestive now and Michele frowned at him and then slammed the door shut and locked it. She leaned back against it and sighed. Then she looked down and saw the faint outline of her penis though the material of her tight skirt. Had the conductor seen it? If he had, why had still continued to flirt with her?

She sat down and poured herself another scotch and wished that smoking was still permitted in railway carriages.

By ten o'clock that night she had drunk half a bottle of the scotch and had finished reading the newspapers. She was too far under the influence to concentrate on reading the novel she had bought. She sat on the bench seat with her feet curled under her having kicked off her heels hours ago, smoking an illicit cigarette. She had smoked a half a dozen so far; puffing the smoke out of an air vent as the compartment window would not open. She was considering taking a shower and going to bed when she heard a light tapping on the door to her compartment. She got up and walked to the door in her stockinged feet.

"Who is it?" she whispered; the train was darkened and her sleeper was only illuminated by a reading lamp.

"It's me," hissed the conductor on the other side of the door.

"What do you want?" she asked tersely.

"I know you're smoking in there. It's against completely against company policy," he hissed.

"So?" Michele hissed back defiantly.

"So let me in and we can talk about it; otherwise I will have to call my supervisor!" he hissed back insistently.

"Shit!!!" Michele whispered and opened the door.

The conductor slid past the door and closed it behind him, locking it.

"It's ok luv; I'm not going to turn you in. I'm on a break and I smelt the smoke walking down the passageway and I thought you might give me one, and maybe a glass of that scotch," he smiled that cheeky smile again.

"Cheek," Michele answered, but offered him her packet of cigarettes and poured him a drink.

"Mind if I sit; I've got two hours off until I have to go to work again?" he asked, but plonked himself down on the seat without waiting for a reply.

Michele turned her back to the conductor to pick up her drink when she suddenly felt him slap her on the buttocks. She was stunned and turned quickly to face him, an angry look on her face.

"Don't worry love; your secret's safe with me," he smirked.

"What secret!" Michele hissed.

How could this man know anything about the money she had stolen?

"Well; the secret that you keep locked away in you tight pretty panties," the conductor glared openly at the front of her skirt.

"I've been around enough trannies to know one when I see one luv; and that telltale bulge you had in your skirt when I checked your ticket only confirmed my initial thoughts."

Michele was astounded and confused. What was she going to do now? What did this man want? There was only one way to find out.

"Well what do you want?" Michele asked tentatively.

"Just a little company, a couple of drinks and a smoke; that ain't asking too much is it?" the conductor gave her his cheekiest smile yet.

Michele thought it over. The man knew she was a transvestite but he seemed friendly enough and it wouldn't hurt to have a little company for a while. She was less likely to be accosted by one of Tony's henchmen, as unlikely as that might seem, if she had another person she could trust in the sleeper with her.

"Ok; you can share my booze and smokes but there are a few conditions," she said.

"Sure," he answered

"No questions about who I am, where I'm going to, or where I'm from!"

"Sure," the conductor smirked again.

"And you keep your hands to yourself," she finished.

"Definitely," the conductor answered.

They chatted for about half an hour and Michele admitted that she has been a part time transvestite for most of her life but this was the first time she had undertaken a journey whilst in drag. She did not reveal anything else of significance to the conductor. The conductor, it turned out, had been a long time transvestite admirer from Sydney. He had clocked Michele as a transvestite as soon as he saw her trying to get on the train with all of her baggage. He was a nice enough guy and they whiled away some time drinking, smoking and laughing.

Michele was now quite drunk and was sitting with her back to the darkened window, lounging sideways on the seat with her feet resting in the conductor's lap as he slowly massaged her nylon encased toes.

"Oh; that feels good," she muttered, now almost half asleep.

The effects of the alcohol and the excitement of the last two days were taking their toll.

"You really are quite passable you know? And if you don't mind me saying; quite attractive," the conductor smiled.

"I bet that's what you say to all the trannies," Michele giggled.

The conductor was now stroking Michele's legs, letting his fingers softly massage them from the tips of her toes to just above her knees. Michele frowned and pulled down the hem of her skirt.

"I thought I told you to keep your hands to yourself," she said sternly; but then giggled again.

"I've had enough of men taking liberties with me over the last couple of days," she hiccupped.

The conductor made no effort to stop what he was doing and now moved his hands over Michele's knees, still softly stroking and massaging her nylon encased legs. Michele made a half-hearted effort to shoo his hands away but she was now so drowsy that she was almost asleep.

"Don't be naughty," Michele whispered and drifted off into a heavy doze.

Michele woke up about ten minutes later and through her drunken fugue realised that something was dreadfully wrong. She was lying down on the bench seat on her back with her arms stretched out above her head, her wrists tied to the armrest. Her buttocks were propped up off the seat, lifted up by pillows that had been stuffed underneath her. The conductor was holding her legs up in the air, her thighs parted and her pantyhose and panties had been pulled down.

The conductor was kneeling on the seat holding her legs up, ankles together, with one hand, whilst with the other he was trying to guide his penis into Michele's anus.

Michele screamed.

"No!!!!!!!!!!!!!"

"Sssshhh! Michele; do you want someone to come to the door?" the conductor grinned, his face visible to her between her upraised legs.

"What are you going to do? You're a trannie travelling undercover for some reason; do you want to have to deal with the railway police or the state police?"

"I think you've wanted this for a long time but you just never knew it!" he hissed.

Michele was not going to let this man abuse her; she had been sexually abused twice in the last two days and this time enough was enough! She was going to fight! She was just about to scream again and was struggling against her bonds when the head of the conductor's penis pierced her sphincter.

The conductor was wearing a lubricated condom which eased his entry but the pain was incredible. Michele moaned and bucked in agony as the conductor rode with her, not trying to push himself any further inside her but not letting her eject his cock.

"Ohhh!!! Hurts! Hurts! Hurts! Hurts! Hurts! Hurts!" Michele whimpered now fully awake but in shock.

"Shhh Honey; relax and it will be ok," the conductor whispered, trying to sooth her.

"No! No! No! No! No! No! Take it out!!!" Michele moaned.

Michele was feeling a constant deep burning sensation combined with spasmodic twinges of intense pain that shooting from her sphincter. She whimpered and wriggled trying to expel the intruder from her back passage but the conductor held on matching her movements.

"Michele!!!" he hissed; and she stopped struggling and listened to him.

"Look honey, the worst is over I promise, if you lie still and let me; I can make this experience special for you. Or you can keep struggling and I'm going to fuck you anyway but it's going to hurt."

Michele realised that once again she had been beaten and she would do anything to stop the excruciating pain that was coming from her sphincter. She sighed and lay still; her wrists tied to the armrest, legs pushed up in the air; her anus pierced by the conductor's penis. She was miserably uncomfortable and she was only just bearing the pain of the penetration. But she was smart enough to know that fighting was only going to make the pain worse. She tried to relax her sphincter but her instinct was to try to push against the object invading her anus; not to accept it.

"That's it honey," said the conductor as he felt Michele's sphincter spasm as she tried to relax it.

"It will be ok I promise."

Michele was quietly sobbing but at the same time she forced her inner muscles to relax. Amazingly the twinges of intense pain began to subside; she still felt the burning sensation around the entrance to her anus but that was tolerable.

"Ok honey; keep relax, I really don't was to hurt you," the conductor soothed.

Millimetre by millimetre the conductor slowly pushed himself inside Michele; he took his time and whenever Michele flinched he stopped and soothed her. He had a tube of KY jelly which he liberally smeared on his shaft as it slowly disappeared inside Michele's rectum. Michele felt full and intensely uncomfortable, the urge to expel the conductor's penis was immense and she had to physically and mentally prevent her internal muscles from contracting.

After ten minutes the conductor had about half of his girth buried inside Michele's anus and he had lowered her legs so that they now rested over his shoulders. He looked down at her tear stained face and smiled.

"It's ok Michele; you're doing fine."

Michele's only response was a another silent tear. She had stopped sobbing and now and only mewed softly when she felt a twinge of pain, but now that she had learned to relax her sphincter she really didn't feel any pain. Even the burning sensation had subsided; she just felt full.

The conductor continued to press slowly forward cooing and encouraging Michele to stay calm and relax her anal constrictor muscles. Then, when he had about three quarters of his shaft inside Michele, he sensed her internal muscles respond and she gasped. He knew what it was; it was not pain. His glans had found her prostate gland. Her reaction was pleasure not pain.

The conductor knew better than to rush; he took his time pushing the remaining few centimetres of his shaft inside Michele until eventually he was buried inside her with his scrotum resting snugly against her. He lowered his upper body down and as he slowly wriggled his penis inside her to stimulate her prostate he kissed her. She began to respond and kissed him back.

After the burning sensation ceased Michele just felt full; she wanted to evacuate the object that was invading her back passage but she forced herself to relax. The invading member slowly forced its way deeper inside her but because the conductor was using copious amounts of lubricant there was very little pain. The conductor was cooing and encouraging her and because of this, combined with the effects of the alcohol she had drunk, she began to relax.

She felt the conductor's glans rub against an area inside her that suddenly caused waves of intense pleasure to course through her body. As his penis stimulated her prostate, rings of pleasure ran up and down her insides; her sphincter responded and loosened and began to emit its own tingling ripples of pleasure. Michele gasped.

When the conductor lowered his mouth to hers she kissed him back, deeply, passionately. She drove her tongue into his mouth and lifted her buttocks up off the seat and pushed herself up against him; her legs moved around his waist; she locked her ankles together and held him against her. She felt totally feminine lying here underneath this man; wantonly giving herself to him.

They fucked slowly but passionately taking their time; the conductor easing his penis in and out Michele's anus with long slow thrusts as she raised herself up to meet him. There was no fervent thrashing or pounding; just firm, slow deep thrusts provided the maximum stimulation for both of them. They said little to each other, the fucking was accompanied by one long passionate kiss.

Michele felt him orgasm; his cock was fully embedded in her, his scrotum tickling her buttocks when he shuddered and wriggled his member inside her as it pulsed and throbbed. She couldn't feel his ejaculation of course because he wore a condom, but she could feel the jets of sperm pulsing from his penis into the condom. He was kissing her wildly now, their tongues entwined, lips mashed, their teeth occasionally cracking against each other with the passion of the kiss.

Michele moaned as her own orgasm shook her body and she felt her semi erect penis begin to pulse and expel her issue. The conductor slid a hand between their bodies and milked her as she ejaculated, splashing her skirt and blouse with her hot semen.

The conductor lay on top of her, supporting his weight on his elbows as they both slowly came down from their orgasms. He placed little soft kisses on her lips and kissed her on the eyelids and stroked her hair. Michele felt feminine and fully sated. She felt like she knew what it would be like to be woman who had just been made love to, and her lover, in no hurry to leave, was content to remain in her arms and express his affection.

After a while, they separated and faced the awkward situation that often accompanies a spontaneous sexual encounter with a stranger. The conductor removed the semen filled condom, flushed it and cleaned himself while Michele dabbed at the semen stains on her skirt and blouse, often getting each others way in the confines of the cramped sleeper.

The conductor handed Michele a business card.

"If you're staying around Sydney give me a call," he flashed his best smile at Michele.

"We'll see," Michele replied.

"Gotta go back to work; bye Michele."

Michele leaned forward and they exchanged a long lingering kiss before parting. As the conductor turned to open the compartment door Michele tapped him on the shoulder and he turned around.

"What's your name?" she asked.

"Oh; Gary. It's on the business card." He replied.

Michele unexpectedly lashed out her hand and slapped him across the cheek.

"Next time Gary; ask before you take," Michele said harshly.

Then she smiled up at him and his shocked expression broke into that winning smile. Michele leaned into him and kissed him quickly on the lips and patted him on the buttocks.

"Go to work," she chided, and pushed him out the door.

Michele checked her watch and seeing that it was close to midnight she quickly showered and climbed into her sleeping berth. She was awoken about four hours later; the train was approaching Central Station and she had just enough time to change into clean clothes and fix her makeup. Hungover and tired she collected her suitcases, and pushed her trolley our into the cool early morning air. She caught a taxi to Kings Cross and booked into the Crest hotel in Darlinghurst Road. She stripped off her clothes and fell into bed dressed only in pantyhose and panties without even removing her makeup.

At first Michele had disturbing dreams of being pursued, interspersed with dreams of feminine erotic encounters. Her sleep was fitful and confusing but by the time the sun was rising she was in a deep dreamless slumber.

Steve had caught the first available plane to Sydney and picked up a hire car at the airport. By the time Michele was waking from her deep sleep late in the afternoon, Steve had checked into his hotel and was at Central Station making enquiries about the well built, mature, attractive woman who had arrived on the XPT earlier that day.

To be continued...