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Undercover Angel Ch. 03
Undercover Angel Ch. 03 – Transvestite in hiding forced to fuck.
Steve Marshall rolled into Wodonga and met with his contact; the manager of the Best Western Motel. The manager had spotted Michele’s blue Ford and checked the guest register and discovered that the driver of the Ford, a ‘Ms Mary Smith’, was currently occupying room 113. The night clerk had described the woman to the manager; and then the manager had contacted Steve. By the time Steve Marshall arrived, things had taken an eventful turn.
“Tell mister Marshall what you saw,” the manger told the night clerk.
“Dude, that chick bolted out of town like her arse was on fire. And, oh yeah, she had like, changed her hair from brown to blonde. Freaky huh?” the night clerk said, withholding most of the truth.
Steve could see that the clerk was nervous and scared. He was also blatantly lying.
“Let me talk to this guy on my own for a while will you?” Steve said to the manager.
The manager left the office and Steve pulled his chair up close to the clerk.
“Let me tell you something son; I’m a pretty generous person and if you help me, I’ll help you.”
“But if you continue with this line of bullshit you’re going to get hurt,” he said menacingly.
“Ohhh dude,” the clerk was about to further embellish his lies when Steve took a small pistol out of his pocket and put it on the desk within easy reach.
“No; let me tell you something ‘dude’; and then reconsider the answer you’re about to give me. This pistol is only a twenty two and it won’t make much noise if I use it. Also, it’s not much of a gun if I really wanted to kill someone. But if I was to say, shoot you in the kneecap, it would really hurt,” Steve said.
The clerk paled, and realising that Steve was not a man to be fucked with; he told him of the scam he had running with his friend, robbing selected hotel guests. He explained that he had thought the woman was out of her room for the day so his friend had broken in to the room to rob her. But the woman must have returned to her room unseen and so his accomplice had entered the room to find her still there. He also told Steve about the briefcase that the woman refused to let go of.
“Call your mate and get him here right now!” Steve ordered.
A few minutes later the clerk’s accomplice sat beside him in the office, and having received the same threats, told Steve his own version of what had happened in the motel room and then looked expectantly at Steve.
“So you expect me to believe that a well dressed, mature, attractive woman in her forties offered to fuck a decrepit petty thief like you rather than hand over a briefcase?” Steve said in response the tissue of lies he had just heard.
“I told you dude, we wrestled, I got on top of her and cut away her panties, and when I fingered her cunt she got hot all hot for me man. She said she would fuck and suck me if I left her with the briefcase. So what’s a dude to do dude!” the young thief laughed.
Steve looked him squarely in the eyes; reached for the twenty two, and shot the clerk in the foot. The unkempt youth jumped and the clerk started to scream.
“Shut the fuck up!” Steve ordered.
“Now; you lie to me again and I’ll shoot out his kneecap next time.” Steve said to the thief.
“I can see you’re all banged up from a fight, so I believe that you struggled with her, but not that she let you fuck her. So, this time the truth please.”
“Ohhh dude; I had a knife and I did cut up her panties, but then I decided to get her to suck me off first. I made her do it; but she bit me on the dick and squeezed my balls. That chick is fucking vicious; she fucking kicked me while I was down dude,” the thief whined.
“So you two fuck-heads decide to steal a briefcase from a middle aged woman and then you decide to **** her and she kicks your arse and escapes with her money,” he chuckled.
Steve stood up and dropped an envelope on the desk.
“Hopefully this will cover your hospital bills,” he said and shot the thief in the foot.
Both of the youths were now grimacing in agony, holding on to their feet, and suppressing cries of pain.
“Don’t try and **** and rob any more women; you’re no good at it; ‘dude’,” Steve growled sarcastically and left the managers office.
He paid the manager enough money to cover the mess and to keep him quiet.
“Tell those two shit-heads to tell the police they shot themselves in the foot whilst climbing over a fence while they were out rabbit shooting,” Steve said, “they’re fucking stupid enough to have done it.”
He got back into his car and as he drove out of Wodonga he smiled to himself and thought, ‘I’m beginning to like this woman; I can see what Mike Harris sees in her.’
After leaving the service station and throwing her sliced up panties out of the car window as gesture of defiance, Michele realised that she needed to ditch the car. She had left the young thief u*********s on the floor of her hotel room but if he had an accomplice he might have seen her leave. It wasn’t worth the risk. She turned her car around and skirting around the city of Wodonga, drove into the twin city of Albury and parked the Ford at the railway station in the long term parking area.
She collected a trolley and took her bags to the ticket office. The XPT train to Sydney left at 3:05pm and there was a double sleeper compartment available. Michele paid for both of the berths in the double sleeper so that she had the compartment to herself. She took a change of clothes out of one of her suitcases and put them in a suit-carrier and she then she unpacked her cosmetics case. She checked the two suitcases at the luggage check.
She had just enough time to smoke a cigarette and buy some snacks and drinks before the train arrived. She had no intention of leaving her sleeper during the eleven hour train ride. She purchased today’s newspapers and a novel to keep her entertained and then she waited down at the far end of the platform away from the crowd waiting for the train to arrive.
Michele boarded the train with some difficulty loaded with her briefcase, suit-carrier and her cosmetics case and the bags of drinks and snacks. A conductor in his late forties with a pleasant face and greying hair assisted Michele with her belongings getting them into the small double sleeper. Michele noticed him looking at her legs and buttocks as she reached up to put her cosmetics case onto an overhead storage rack. He noticed that she noticed and blushed slightly.
“Here; let me do that,” he said, guilty at being caught out.
Michele allowed the conductor to pack the rest of her things onto the overhead shelf for the long train ride ahead. He looked at her ticket and smiled.
“I see you have the sleeper to yourself; nice and private. If I can do anything to assist you further during the journey let me know,” he smiled and winked cheekily at her.
It was cramped in the sleeping compartment and she felt him push his groin against her buttocks as he eased himself around her. She thought he really didn’t need to get quite as close as he did and that he was just taking the opportunity to get a quick feel.
When the guard left her compartment she locked the door, and taking a water glass from the tiny ensuite bathroom she poured herself a scotch. She sat down and again pondered the effect she had on some men. Yes she did dress attractively she thought, and she had a reasonably good figure for a well built woman. She liked to show a bit of leg and wear plenty of makeup, but none of this was done intentionally to attract the attention of men.
Despite having been a part time transvestite for most of her life, she had never been out of her house dressed as a woman until the day before yesterday. She was obviously a reasonably convincing woman and the years perfecting feminine mannerisms and speech were paying off, but the sexual attraction she was generating was totally unintentional. Although she did have to admit that it was becoming enjoyable and empowering, and, subconsciously at least, she was finding it sexually arousing.
As the train pulled out of the station she re-lived the events that had happened in her car with the policeman and then the events that had taken place in her hotel room in Wodonga. As she slipped into her reverie she realised that her penis was slowly becoming erect and was throbbing uncomfortably trapped between her legs. She smiled to herself and slid a hand under her skirt and inside her panties and pantyhose and released the throbbing organ. She adjusted it and slowly stroked it with her fingertips through the front panel of her panties and the gusset of her pantyhose; and as it tented her skirt, she ruminated about her recent sexual misadventures.
Steve drove out of Wodonga but he had no idea in which direction the woman had gone after she left town, he mentally tossed a coin, and pulled on to the highway heading north. A few kilometres out of town he came to a full service petrol station and pulled in to fill the tank. On a whim he asked the attendant about the attractive mature woman driving the blue Ford and was quite surprised when he got lucky and the attendant remembered a woman matching the description. He said she’d filled up, used the rest room in the restaurant and then continued her journey. He noticed her because she was well built and attractive but there was something not quite right about her.
Steve asked if there was video surveillance at the service station and sure enough there was. He showed his fake police ID and got one of the attendants to run through the security video. There were a couple of minutes of footage of a woman sitting behind the wheel of a blue Ford parked at a petrol pump. That had to be her! It was hard to get a good look at the woman because she was obscured by the attendant moving past the driver’s window and reflections from the car’s windscreen.
They played with some of the other footage and then they got her! The footage showed her coming out of the restaurant wearing a white A-line skirt with kick pleats and a blue silk blouse, her sleek pantyhosed legs ended in white high heels. She had blonde hair and was wearing heavy makeup. She was a big girl but well proportioned with a nice arse and good legs. As she got into her car her legs parted and the camera showed a brief up-skirt flash of her panties and the tops of her silken thighs.
Steve downloaded the video onto a memory stick and flipped the suspicious attendant a fifty dollar note.
“No need to tell anyone I was here,” Steve said gravely and walked back to his car.
Figuring that the woman was about three hours ahead of him now, and could be heading anywhere, he decided it was time to refine his plan. He drove on until he found a reasonable motel with in-room high-speed internet access and pulled over and took a room. He fired up his laptop and started making calls on his mobile. There was still no word about Mike Harris from any of his contacts; it was like he had disappeared off the planet. He hadn’t used a credit card, accessed his bank account or made any calls on his cell.
He updated his contacts with the latest information he had, including a better description of the woman and her car. The car would have to show up somewhere he thought. He wondered if the woman was leading him on a wild goose chase, acting as a decoy for Mike, or even if they had arranged a rendezvous. Maybe she was just some dumb cunt Mike had paid to lead him further away from him.
Nah! The woman was too smart; he was beginning to like her tenacity. Rather than get a ticket and get caught so early on in her escape she had let the copper fuck her and she’d blown the stupid young thief before biting his cock and kicking the shit out him. She might not have morals but she had determination, he smiled to himself.
He opened his email and found a message in the inbox from his geek. The geek had rebuilt the hard drive on Mike Harris’s computer but had found nothing in his emails or computer files that were not work related. He had found something interesting in Mike’s web browser though and he wanted Steve to call him. Steve called him and listened with interest to what his geek had to tell him.
Apparently Mike Harris had visited a number of transgender sites, not porno, the geek explained, but transgender resource and support sites. He hadn’t visited them frequently but he’d visited them consistently since purchasing the computer. Steve considered this information for a while as he smoked a cigarette and drank a beer from the minibar.
Was Mike some king of weirdo who liked crossdressers? But his geek said there was no porn on the computer. This could just be a dead end or it might lead somewhere; he would need to think about it. He thought about it for a while and drank another beer. He took out a pad and pen and started drawing boxes and bubbles with arrows and lines connecting them all. He liked to visualise his thoughts.
He started writing on the pad: Mike Harris had not been seen since the day before he cleaned out Tony Leonardo’s safe — Did not take his clothes with him — Pantyhose wrapper and cosmetics residue found in bedroom — Well built woman seen driving away from Mike’s house on evening of robbery — Attractive, mature, well built woman uses sexual guile to persuade policeman and delude a thief — Intent on keeping briefcase at all costs — Changes hair colour overnight – Cop claims to have fucked woman and thief claims to have fingered her; could they both be lying?
Steve looked at the diagram he had drawn; his detective work lay out before him in a series of boxes, joined by lines and arrows. He opened his briefcase and pulled the out the papers he had taken from Mike Harris’s study. He found what he was looking for; a faded document with the address and phone numbers of St Joseph’s Orphanage on the letterhead. He reached for his phone and made a couple of calls to officials in the state government who cleared the way for him to call the orphanage and so that he could ask his questions.
He picked up the house phone and ordered a steak and a good bottle of red wine from room service while he waited to be finally connected to a nurse who remembered Mike Harris from when he had been in the orphanage. After some time spent explaining that Mike had gone missing and that he was the detective charged with finding him she finally loosened up and started answering his questions.
“Yes, Mike had always been a loner and a little different to the other boys. Unusual occurrences? Yes Mike had never remained long in foster care and some of the foster mothers had complained that he had ‘interfered’ with their clothes while they were out of the house.” She said.
“And of course there was the time she found him dressed in a pair of snagged pantyhose and nylon panties that he had found discarded in the female staff dressing room. He wore a sarong and a t-shirt with rolled up socks pushed under the t-shirt to imitate breasts. He’d combed out his shoulder length hair and painted his lips with red crayon and lined his eyes with a fine tipped black marking pen.” She told Steve.
Steve thanked her and hung up. Now there were just a couple of anomalies that he needed to resolve and the theory that was gnawing away inside of him would hold water. He contacted his connection at the ACT police who gave him the cell phone number for the cop who claimed to have fucked the woman at the rest stop. Steve punched in into his cell.
“You didn’t fuck her did you?” he growled.
“Well we did have sex,” the policeman answered indignantly.
“Ok; simple question; if you lie to me, you will regret it for as long as you live.”
“Did you put your penis inside the woman’s vagina; yes of no?” he snarled.
The policeman hesitated; his breathing heavy through the phone.
“No,” he answered.
“You didn’t even see or touch her cunt did you?”
Steve hung up and called the Best Western in Wodonga.
Thirty minutes later he had the answer to his next question; the young thief hadn’t seen or touched the woman’s vagina either. Neither of them had; fucking men always had to lie about their sexual prowess!
And he thought he had a pretty good idea why neither of them could ever have seen or touched the woman’s vagina. She didn’t have one!
This woman wasn’t some bimbo accomplice assisting Mike’s escape. The woman WAS Mike Harris! Mike Harris was dressed as a woman fleeing the clutches of Tony Leonardo with two point seven million dollars of his money! You almost had to admire the audacity of it.
Steve’s dinner arrived and as he savoured his steak and the wine he ruminated what he should do next. He decided that Tony Leonardo didn’t need this little gem of information just yet; besides he could be wrong. He’d keep looking for the woman, telling Tony that she would eventually lead him to Mike Harris; which she would, whether his theory was right or wrong.
He chuckled to himself and then started to laugh out loud as he poured himself another glass of wine. Then he thought about how the woman had looked in the service station surveillance video and imagined the cop humping at her and the youth getting some head; he began to stiffen. My; what a strange reaction, he thought.
On a whim he opened his laptop, inserted the memory stick and bought up the video of Michele getting into her car, flashing her panties and legs. He zoomed in so that he could see her body, heavily made up face and blonde hair and the flash of panty and thigh. He set his Windows Media Player on ‘Repeat’ so he could view the video in a continuous loop and opened his flies. His long thick cock sprang free and he stroked it as he watched Michele climbing into her car over and over.
Suddenly he remembered; he had her pantyhose in his jacket pocket; he had picked them up after she had discarded them after the incident with the policeman at the rest stop just outside of Canberra. He walked over to where his jacket was arranged on the back a chair, his rampant penis proudly at attention, and took the pantyhose out of the pocket. He kicked off his pants and lay down on the bed and looked intently at the computer screen.
He didn’t think of the woman on the screen as Mike Harris; he thought of her as a sexy woman with a great arse and lovely legs, unintentionally flashing her assets as she got into her car. He stroked his cock and bought the pantyhose gusset to his face. The fragrance of her perfume clung to the diaphanous garment and there was also an underlying odour of semen. His cock throbbed, now fully erect; almost painful.
He lowered the flimsy garment to his groin and slid one on the legs of the pantyhose over his straining member. He groaned and slowly slid the gossamer hosiery up and down his cock. He tried to hold back but he couldn’t; his cock convulsed and he wrapped the pantyhose tightly around his shaft and squeezed the bulbous glans of his penis as he flooded the gauzy material with his semen, darkening the flesh-toned nylon. As he shook in the throes of his orgasm he watched Michele flashing her legs and panties as her skirt rode up as she continually got into her car.
At 6am the next day he was hungover and testy when his cell phone rang. He soon got over the hangover when he was advised that the blue Falcon had been found at Wodonga railway station in the long term parking lot. He shaved and showered and drove back to Wodonga. He checked the time stamp on the parking pass displayed on the dash of the Falcon and went to look at the train timetable. She’d taken the XPT to Sydney; he’d bet his life on it! He looked at his watch; she’d arrived in Sydney four hours ago.
Michele was wakened out of her reverie by a sudden knock at the door. She quickly pulled her hand from beneath her skirt and realised that her erection was tenting the front of her white A-line skirt.
“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.
“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.
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