The Transformation of Simon

The Transformation of Simon

Chapter 1

As Simon stepped into the airport departure lounge he felt himself flush with embarrassment and a little fear. He thought to himself about what he was carrying in his bag, swallowed hard and went to the check in desk.

The check in lady was an attractive enough young slim girl, one who obviously expected that most men would find her attractive. Simon wasn’t really think of that at that time but even if he had he would simply have dismissed the idea. This was the sort of happy young girl that Simon found simply boring to consider as a sexual partner. A girl to take to dinner a few times, then a prefunctionary missionary style copulation, an encounter where the most sexually exciting thing would be if he had her suck his cock. Simon found this sort of vanilla sex, if not actually unpleasant, at least pretty boring. Simon wanted more, much much more and that explained both why he was at the airport and why he was carrying checked luggage he was nervous of.

Simon traveled a great deal and really the idea of flying meant nothing to him. He flew far more miles than he drove and treated it as a low travel quarter if he wasn’t an a plane at least 5-6 times. He also never traveled with luggage. He was always highly dismissive of those poor souls going through those roped off sections carrying big bags. On this occasion though he found himself snaking through those barriers before being confronted with the attractive check in girl.

“So Sir, do you have any dangerous items in your carry on bag Sir?” asked the check in girl. Simon thought through for what felt like the thousandth time in his head, all the items he had packed. 

“No, no I don’t” He smiled rather unconvincingly back. “Just samples for work, and errr my clothes and stuff, you know” He tried to sound confident and calm, and he certainly didn’t look like a terrorist in his Hugo Bose suit and black patent leather shoes. His well manicured hands, were though shaking just slightly as the smile on the check in girls face slipped just for a second as she sensed the disquiet in his voice.

Looking him up and down again, she thought to herself. Oh don’t be silly, his an English businessman, his not any kind of threat. Perhaps his simply nervous of me. Those English can be so very reserved. Laughing to herself about the thought, she took his bag, placed it on the conveyer and handed Simon his tickets.

With a huge sense of relief Simon took the tickets and moved toward the VIP lane at the airport and his flight. So the first hurdle had been passed. Now for the second. He had followed the instructions well and had been as commanded practicing at home. He knew the airports systems well and knew that he wouldn’t be detected unless given a hand search, something that very very rarely happened. Still as he placed his computer, bag, shoes and others bits and pieces on the Xray conveyer his heart did miss a beat thinking of what might happen next.

He stood as he always did just in front of the scanner, it was one of the older metal detector ones and he knew he had nothing metal on him so was going to be safe. He was also grateful that it wasn’t one of the modern body scanners. That after all would have been  much much harder to explain.

Walking through the machine no noises went off and Simon was pleased that there was no pat down. He retrieved his items from the conveyer, packed his laptop away, put the shoes on the floor, slipped them on, bend down to lace them and felt suddenly felt the huge pain of the big butt plug surge through him. He stiffened but knew he couldn’t display anything, so gingerly bent over and tied his laces, the thick black rubber cock in his ass grinding against his asshole and his prostate. The cock was really thick, just as mistress had commanded he wear for the journey, and it certainly was doing a good job of stretching him out. He just knew that being open for his mistress was going to be very important. From what she had said he could expect no mercy once he arrived and from the pictures he’d seen and the conversations they had had he knew he was going to be taking a severe pounding in his cunt this weekend.

The flight was ok, and just like hundreds of others. The only difference was that this was the first time he’d had a big plug in his ass, and there was no room for him to open his legs so the CB-6000 male chastity device was pushing on his inner thighs. He kept having to move to different positions and this of course drive the dildo deeper into his ass.

With 20 minutes to go in the flight Simon decided he better check that everything was right for his first meeting with mistress. After all she had been very specific how he should look when she picked him up at the airport and he didn’t want to get anything wrong.

Proceeding to the rest room Simon locked the door and took a look at himself in the mirror. His hair looked ok. It was greying at the temples but at 43 that was hardly surprising and he was still pretty happy to note that he still had a very full head of hair with no sign of male pattern baldness. His glasses were clean and straight although he had to smile to himself as he suspected that wasn’t going to last long once he arrived.

His teeth were very clean and white and although not advertising perfect were not the standard mess that British peoples teeth always seemed to Americans.

The size 42 jacket fitted well and he thought to himself that getting down to 180lbs with all the cycling he’d recently being doing had been worth the effort. It has also toned up his ass and legs very considerably and he hoped that mistress was going to like that.

His pin stripe suit looked clean and fresh and unrumpelled. . He thought he better check everything so he dropped his pants and undid the buttons of his white shirt after taking his tie off, to check everything was ok underneath. The black stockings looked good, and showed off his legs pretty well. The black G-string covered the CB-6000 completely and the pink lacy basque felt nice under the shirt but thankfully didn’t show under his shirt. He was so pleased mistress hadn’t insisted on a corset or something black. Hiding that would have been far more difficult. 

Simon felt around behind himself and felt the end of the but plug between his buttocks. He thought about taking it out just for a moment of relief but thought about what he would do if he couldn’t get the thickness back inside himself. What to do? The fullness was both good but also uncomfortable. He reached behind himself and started to gently tug on the base of the plug. The much thicker part of the plug began to emerge from his anus and he felt the pain begin to build. He knew it was going to be a real pleasure pain to remove it, but thought it would only be extremely for a few short seconds and oh the relief. 

Just as the plug was approaching it’s thickest, there was a loud rap on the door.

“Please sir, can you return to your seat, we’re coming into land shortly” Said the disembodied voice of the stewardess.

Quickly Simon pushed the big plug back into his protesting anus ,pulled up his pants, washed his hands and buttoned up his shirt and went and sat down.

As he retied his tie, standing by the aisle, the lady he’d been sitting next to looked up and smiled. “Been getting changed have you? You look flushed. There’s never enough room in those things is there.”

Simon mumbled something about it being a very tight fit, sat down in the window seat, and looked at the clouds scudding by as they came into land.

This airport was new to him. He often traveled around the country and had been to many of the major airports and a fair few of the second tier ones, but this was new. As he approached the luggage carousel, he pulled his phone from his pocket and as commanded send mistress the one word text message. LANDED. She had demanded he do nothing other than announce that he had arrived.

As the bags came around on the conveyer, Simon keep looking for the reply while occasionally looking up for his bag. Finally his bag emerged from behind the curtain. He expertly moved through the crowd, slipped a hand out, picked up the heavy bag by the handle, pulled out the extender with a single motion and started toward the exit, just like dozens of other business people do at airports across the world.

Just as he got within 30 feet of the exit to the arrival lounge, his phone beeped with an incoming message. It was mistress, the message read ...........

Simon looked down at his phone. He already knew what to do. He’d been told before on one of his numerous on-line training sessions how things would go from here. Whatever the text message stated was what he had to write on the card he had already brought with him on the plane. He was then to stand at the end of the car pick up point so that everyone leaving would see him, displaying that card.

He’d never really thought how this bit could be humiliating but as he passed through the security doors into the arrivals area his heart pound in his ears as the read the words Sissy Whore on the screen of his phone. Instantly his face reddened. He knew there could be no backing out now this was his destiny. THe thing he’d been working toward for months since first finding or was it being found on all those months ago.

He thought back to the initial conversations, how the lady had seen his profile, responded intelligently and with interest to his on-line advances. At first the relationship had been one of tease. she had enjoyed his photos, even the filthy videos he has made for her. Simon did after all have some very extreme desires and was so pleased to meet a lady prepared to not only discuss them but to even enjoy many of his deepest desires. Simon had spend much of his life being the alpha male, being the brash, type A personality. In the day today world he enjoyed that and was successful professionally because of that. However deep down he had deep deep suppressed wants, needs even to be a wanton whore. To be taken, fucked, totally abused by huge cocked strap-on ladies, to have his holes filled, his own genitals mocked and punished.

All of this flitted through his mind as he wrote the sign. His cocklet, which hadn’t been out of its cage for months pushed urgently against his CB-6000. He was relieved to notice it didn’t show on the outside of his suit, but it was certainly painful having his cock f***ed into such a tight restricting device. Over the months he’d grown used to it, and the pain was in some way also a pleasure.

Walking to the end of the pickup point Simon gingerly lifted the sign, and stood and waited. THe next 15 minutes were acutely embarrassing. Cars honked, people pointed and laughed as he stood waiting for the car. He didn’t know what vehicle the lady had and so needed to present the sign to every vehicle. A number of times the Police drove past and gave Simon a very long hard stare. They didn’t know what he was up to, but didn’t like it anyway. Trouble was it wasn’t i*****l.

Finally after 15 minutes of standing there a stretched limousine rolled to a halt. The window wound down in the back and a voice stated in a deep but female voice. Put your bag in the trunk and get in. Simon saw the trunk pop and he lifted his heavy bag into the trunk, closed it with a thunk, opened the side door and climbed in.

Sitting there looking even more erotic than the webcam could possibly convey was Sir. She had insisted on it from the first time they had communicated. Simon looked are up and down his hands, and in fact his whole body shaking a little as he took her in. She wore a suit, a pin stripe suit something Simon had always loved on a woman. The crisp white shirt bulged over her ample bust, the red tie tucked into the suit jacket that was button with a single button. sir’s bust made a beautiful triangle of the shirt. It should of course have been called a blouse with a lady wearing it, but Simon simply could imagine this being anything other than a shirt.

Sir’s legs looked thick, long and powerful in the pinstripe pants. Th e most feminine part of Sir being the slight view of shear black stocking before her black, patent leather shoes started. The heels were high. Simon guessed 4 inches, but they might be more.

Sir’s beautiful dark skin set off the white shirt beautifully, and Simon was intrigued to notice that Sir was even wearing cufflinks. Sir’s hair was worn up and gave her the look of a powerful business person.

Sir looked over at Simon. “Well cunt. Show me”

“What here now in the car?” Simon stammered back

“Do it now, you fucking whore” Sir replied menacingly

Simon slide of the chair into the large footwell of the Limousine. Kneeling facing Sir he began to undo his belt.

“ No whore. I don’t want to see your face. Turn around. I want to see my new cunt” snapped Sir.

Simon shuffled around. It wasn’t easy the Limousine had by this point got out of the traffic near the airport and was on the freeway, going who knew where.

Simon bent over unbutton his pants, and slowly slide them down to his knees.

Sir had a view of Simon’s white ass, all shaved and ready. The butt plug firmly stuffed into his ass, the pipe to the pump sticking out. She could also see his shaved balls bulging from his CB-6000 and his semi hard cocklet stuffed inside the clear tube.

He appeared to have done everything Sir had wanted. She smiled, but of course was conscious of not letting this maggot know it.

“Ok whore, hand me the pump” Sir stated calmly.

Simon reached into his pocket. Took out the bulb of the inflatable butt plug and handed it to Sir.

The moment Sir had it in her hand she started to pump it, all the time looking Simon in the eyes as he looked over his shoulder back at her. His ass sticking up in the air.

One, two, three, four, five, six pumps. The feeling went from feeling full to feeling very very full almost instantly. Seven, eight, nine, ten. Now Simon was really squirming with pain and with how big that cock felt in his ass. Simon had, for many months been practicing, often on webcam sessions with Sir, taking bigger and bigger cocks. She had only agreed to meet him after she knew he could take big cocks. Sir loved big cocks, and had no interest at all in virgins. She wanted to blunder her whores, fill them completely, give them the fucking of their lives. Hurt them, humiliate them, f***e them to be the most basic cock taking bitch in the world. From the first time they had met on line Sir knew Simon was one of those whores she could take all the way.

Simon cried out with the pain on pump twelve and Sir stopped.

“Good work whore. You have been doing well. I think you truly are ready to take the fucking you so sorely want”

With that Sir, deflated the butt plug suddenly, and gave it a firm yank. It popped out of Simon’s stretched ass. Simon stay in the position he was in before breathing heavily as Sir looked down. Simon’s ass was gapping wide open, twitching. She could have thrust her fist straight in there but she thought. No, that can come later.

“Ok whore. You’ve done well. Now let’s see how good you are with the other thing I hope you’ve been practising. turn around and try my cock” With that Sir lay back in the seat, put her hands behind her head and smiled down at him.

Simon knew what he was to do. turning around to face her, he slowly put his hands to the fly of her pants, unbuttoned the top of of pants, and slowly unzipped the fly. Looking up he could see her continuing to smile down at him.

“That’s it, take it out”

Simon slowly reached in down the leg of Sir’s pants. felt the heavy thick rubber of her cock and slowly pulled it out. Once it was free of her pants Simon could see the black 12 inch cock in all it’s glory. Sir really did look like one of those Big Black Cocked slut fuckers from the porno movies who get to fuck the shit out of little white girls. The irony and symmetry of this wasn’t lost on him.

“Go on whore, suck my cock”

Simon moved his mouth, taking as much of the head as he could into his mouth. It wasn’t as thick as some he had seen and he could take the cock head into his mouth. As soon as he did Sir begun to buck her hips, slowly at first but with increased rhythm into his mouth. Simon tried to raised his head to stop choking but instantly Simon felt both Sir’s hands on the back of his head forcing him down onto her big black cock.

“That’s it cunt, take my fucking cock” Sir barked “You fucking sissy faggot. You fly up here, after months of on line training. I bet you thought it would never be that extreme. you’d get up here. Meet me. I’d be nice to you, You’d get the key back to your little fucking CB-6000, perhaps I’d let you fuck me and then you’d get to go home. Was that it? Was it?”

Simon tried to respond but with some much of Sir’s cock in his mouth he could barely say more than a mumble. It was obvious Sir wasn’t listening anyway.

“Well cunt. I’ve got new for you” Continued Sir. “Not only am I going to **** the shit out of you, but I’ve got a bunch of people I’ve shared all your photos, your movies, your little stories with, who want to meet you. And boy are they going to have some fun with you.

We all agreed, you’re nothing but a cum dump whore and we’re all going to take advantage of you. After all what you going to do. Go to the police? Really with all the emails, pictures, movies and other things you’ve sent me?

I also bet your bag is full of pervert things as well isn’t it bitch. So there’s no getting away. This is going to be a long week, and a profitable one for me too. you see I’m not just sharing you with my friends. I’m going to be selling you. We did the auction last week at the club. your movies and photos were most helpful for that, and so I have you booked solid for the next 5 days. I’ve made over $1000 pimping you out. Right now I’m taking you to the hotel you’re going to be working from. It’s much cheaper than the Marriott you were booked in. But these Extended Stay hotels are cheaper, and many of the people you are going to meet prefer not to go through the reception of a big hotel. I’m sure you understand.

We’ll be at the hotel in 10 minutes, so you can get change into your female whore gear. Then the fun begins. Now don’t stop sucking now cunt.”


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Posted by simon66_99again2
3 years ago    Views: 1,007
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1 year ago
Fantastic. Great start. I want more!
2 years ago
Hi, great story! I was hoping fro more chapters!! thanks again for the great read. paull