Unsureness about Trousers

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"Does that worry me? I meant not a lot of point because he isn't going to come again until long after Anne and I've got off the train and found our hotel. I can't leave Anne behind can I? So that won't do as a marker. No, let's think of something else."

"You could suck me."

The presumption seemed to leave Anne's friend speechless for a moment. "I really don't think I would want to do that." She said slowly and sniffed.

The middle-aged woman was still in her seat, looking furious but not saying a word. Anne's friend stepped up the carriage and sat down beside her and put her arm around her, "Sorry I have been neglecting you haven't I?"

The woman shook her head violently from side to side.

"You are kind, but I have been busy with Anne, she can be so bad you see, and forgetting your needs. Now let us see, what was it you wanted to do? Did you want to suck Robert? Did you want to taste his cum as it dribbles into your mouth?"

The woman kept shaking her head.

"Did you want then to feel his, well rather small cock fucking you? I am sure if I ask him to tickle your clit as well you will come despite it all, don't you?" She smiled.

The woman looked horrified and shook her head the more.

"Well, what do you want from Robert if you don't want to suck him and don't want to fuck him? Oh surely not! You don't really, do you? Well I'd never have thought it. I should think it hurts, though..." she paused and began rummaging in her handbag, "I think I do have in here—yes here it is." She drew out a tin of Vaseline. "I use it on my lips to keep them shiny but I am sure it will do just as well on your bottom."

The woman's head shaking stopped and she just gaped at the girl who was smiling so sweetly and offering the tin.

"Yes, I thought so. A funny thing to want on a train. Still there is no accounting for tastes. Certainly I... but, well we'd better get your bottom ready hadn't we?" Without asking she began to undo the woman's blouse buttons.

The woman slapped her hands away.

"I am sorry. You want to undo them yourself? Carry on then."

Despite her wild-eyed look the woman began undoing the buttons, her fingers seemed to be working of their own accord, and she slipped the blouse from her shoulders. No longer hidden in her blouse her deep cleavage showed in her ample bra.

"You'll want to let them out so Robert can hold onto and squeeze them."

The woman reached behind her and she lent forward and pulled her bra from her.

"Oh, wow," said Anne's friend.

They were certainly substantial and topped with large pink areolae.

"What we see is good, aren't they Robert?"

"Yes, yes certainly, yes good."

"I expect you'll need to restrain them when she starts thrashing around with your cock in her arse. Can you do that do you think? Can you satisfy her desire? Can you fuck her in the bottom?"

"Yes, I can do that but I don't want..."

"Of course you do."

Robert suddenly looked more enthusiastic at the prospect of anal intercourse.

Skirt dropped to the floor and the woman slipped out of her panties. Her bottom was round and generous—not in a saggy, over-fed way, but ample and soft.

Anne's friend opened the tin of Vaseline, "Robert could you prepare the lady?" She paused and spoke to the woman, " I think you will need to bend over a bit dear, Robert is going to take you sort of doggy style, only in your bottom."

She complied but with her head shaking and her mouth mouthing a very clear 'NO'.

Robert picked up the tin.

The middle-aged woman was now leaning forward right over where Anne's friend was sitting, her impressive breasts hanging forward.

"These are really nice, such a good handful." She reached up and juggled them in her hands as if weighing one against the other, before pulling on the nipples and rubbing them between her fingers, "I wonder how wet you are, may I feel?"

The woman shook her head.

"Don't be silly, of course you want to be felt there. You will love it. In fact I think you will find having a man in your bottom and a woman stroking your wetness will prove to be the best sex you've ever had." She winked, "actually I know it will be because when I say 'come' you are to have the best orgasm you've ever had."

The woman kept shaking her head but when Anne's friend's hand slipped between her legs and a finger touched her there her eyes opened really wide as if something new and rather wonderful was happening.

"Robert have you greased her up yet?"

Robert's finger scooped Vaseline from the tin and poked between the woman's bottom cheeks and began to rub the Vaseline around the rubbery ring of her anus. He began to slide his finger in as he applied more ointment.

"Come on Robert you know what to do."

Robert took himself in hand applying yet more Vaseline, and as the carriage watched in stunned silence, lined himself up and pushed. The Vaseline did the trick and as he pushed the ring opened and the shiny, but small, head of his penis slipped into the woman's bottom.

The woman blinked rapidly. Anne's friend's fingers played with her sex.

"Nice isn't it, feeling Robert's thing sliding slowly into your bottom. I bet you've never had that done to you before, have you?"

The woman shook her head.

"But you like it don't you? Robert's cock in your bottom and my fingers filling you here." Her hand pushed forwards and up.

The woman nodded vigorously.

"Come on Robert, I can feel you. Impale a little further and yes, you are all in. None of your cock left outside at all, just your hairy balls. Now how does that feel Robert, your cock buried in this lady's bottom and the special treat of me stroking your balls? I don't often do something like that but as you have been very good—it is a special treat just for you. Feel all her wetness I am rubbing into your balls, isn't she just so sopping, Robert—but that wetness is not for you. I want you right there in her bottom. Start moving Robert—let the whole carriage see how you fuck a bottom."

Robert worked hard, with long very visible strokes—it was just as if he was playing to the audience. His hips slapped against the middle-aged woman's bottom, his oiled penis shaft slid backwards and forwards and all the time Anne's friend's fingers were busy, very busy. The woman was gasping, perspiring freely and clearly utterly absorbed in the carnal experience she was undergoing.

"I think you can COME now," said Anne's friend and the woman very, very obviously did have a shattering orgasm—a prolonged climax which seemed to the carriage to go on and on for a quite remarkable time. But her experience wasn't over. Anne's fingers did not stop and nor did Robert.

"Very good dear, but you are going to come again and this time we all want to hear how good it is. You are going to come just as Robert squirts his stuff up your bottom. Think of that, a man right in your bottom!"

"Robert, are you ready?"

Robert came but what was more evident to the carriage was the woman's second orgasm. Her cries of "No," mingled with the most surprising obscenities from such an upright and prim and proper woman - sound that must surely have been heard by the other carriages on the train. Still spasming she fell off Robert's cock and lay quivering and whimpering on the seat. Anne's friend patted her shoulder.

"There, there a good orgasm or two does a girl a power of good. I am going to have three or so later tonight and I know that will be good for me." She glanced at Anne.

Anne looked a little worried as if there was something bothering her.

"Now what are we going to do with you?" Anne's friend turned to the boy who had not come in Anne's mouth. "You were presumptuous and must be punished. Oh, I know," she clapped her hands," that will be fun. Stand up, take your clothes off—all of them, let everyone see. Come on, you need to be standing."

No one in the carriage was now surprised that he did just that. What Anne's friend said seemed to happen. It was most peculiar and a little scary.

"Turn around, let everyone see."

The boy was obviously and redly embarrassed but it was going to get worse.

"I'm sorry I said something wrong," he said, "can I get dressed now?"

"Oh no! Punishment's not over," Anne's friend laughed. "You haven't let everyone see you naked yet. Walk up and down the carriage."

The poor boy found he had to do that despite his embarrassment at seeing everyone watching him, the eyes of the passengers automatically flicking down to look at his penis. Anne's friend let him parade several times before saying slowly, "I think I said standing..."

The import sank in.

"Come on, just walk up and down wanking—that will do the trick - you will be nice and hard so everyone can see what a big boy you really are and then your punishment will be over. See I am quite generous really."

So the boy found he had no option but to walk up the carriage, his hand pulling at his foreskin, and whilst what he just wanted to do was crawl away and hide with embarrassment he found, incredibly, as he walked his penis got hard in his hand. He was actually getting erect as he walked up the aisle past all sorts of people staring at him. He walked back with his cock as hard as it had ever been sticking out to the front of him. Anne's friend let him parade.

"You're missing seeing another cock," she said to the middle-aged woman pulling her upright on the seat. The strange look of confusion, contentment, disbelief and panic on the woman's face was remarkable as her eyes searched for her clothes.

"I really am quite surprisingly generous, you know," said Anne's friend to the boy. "I'm going to give you a treat for accepting your punishment so well. You have quite a nice little cock, as those things go, and it looks like it needs to come. Of all the people in the carriage, except me of course, whose tits would you most like to come over? There—a free choice—what an offer!"

There was a murmur, a murmur of worry in the carriage. The boy looked up and down and to everyone's surprise it wasn't Anne but another girl further up the carriage he pointed to. She had caught his eye in her low blue top earlier in the journey. It had been as she'd lent forward to push her bag under the seat and the hang of her cleavage had drawn his eye and he had not forgotten. Anne's friend drew him up the carriage. The poor selected girl found herself looking up at Anne's friend whilst being acutely aware of the lad's erect cock very near to her face indeed. She wished she had gone to another carriage when all this had started. She had even pulled her bag out from under her seat but had not actually got up and left. She didn't know why.

"Aren't you lucky?" said Anne's friend to the girl. Don't worry I am not going to make you do anything. Just let's see your titties. Undo those buttons; get rid of that silly bra."

"My, oh my, now aren't they pretty. You really are a lucky girl," and she bent and kissed the girl on the lips. "Really a lucky girl. I could quite take you home with me and think what fun we'd have. Now just sit there and this nice boy, I've promised him you see, is going to come all over your sweet little titties. Hey, look everyone, how the cooler air is making her nips grow. I must just touch, just a little, oh you are a lucky girl!"

Anne's friend turned to the boy. "Off you go you lucky thing, wank away, she's all ready for you."

He did just that.

The girl stared, almost cross eyed, at the cock pointing right up at her, its little eye—closed now—but liable to open and not just to wink at her at any moment. The lad stroked, his hand moving up and down, the shiny head appearing and disappearing in his fist, his eyes glued to the pretty round breasts framed by her open shirt

Anne's friend stood watching and smiling at the girl as the boy worked his cock.

"I'm going to..."

"Here we go," said Anne's friend, "Get ready, yes one, two—oh that was a big one—three, four, five—isn't he doing well - six... and a dribble."

The seated girl looked wide-eyed as the boy's cock splattered semen across her breasts. She'd been worried he would aim for her (firmly closed) mouth but he had directed himself downwards. It had fallen warmly across her but she could feel it starting to run—a drip was even hanging off her left nipple.

"Rub it in, rub it into those pretty breasts. Go on."

And the boy, standing there with a shrinking but still dripping cock moulded her breasts in his hands and spread his cum over them in a circular motion as if he was spreading body lotion. It was sticky.

Anne's friend laughed. Good for the skin tone—though, you understand, I don't use it myself.

The train slowed.

Anne's friend glanced out of the window and walked back to Anne. "Perhaps," she said to Anne, "you were wrong, after all, about those trousers. They really are rather sexy and cool. I think you should try them on again. They are just your size."

"Do you think so?"

"Yes Anne, really. I think they are just you. Andy let her have her trousers to try on again.

Andy pulled them off as he was told.

"Put them on, Anne, get dressed—don't bother about panties, this is our station."

She did leaving Andy standing in a pair of white cotton panties with red trim and quite unsure what to do.

The girls picked up their bags and prepared to leave, seemingly oblivious of the sexual chaos strewn around them.

"What rooms did you get us at the hotel?" said Anne to her friend straightening the grey trousers, which had started it all.

"Rooms? Oh, the hotel was full again and all I could get was a double room."

"A double?

"Yes, sorry, that's all they had—but they said it was a nice room with shower and everything."

"That means we will have to sleep together, again."

"Unless you want the floor. You don't mind, Anne?"

"Well, as long as I don't have to, you know. I didn't like that much."

"Yes you do, Anne, you've forgotten. You like it very much." She turned and winked at the carriage—"I certainly do—perhaps three times tonight!"

And they were gone.

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5 Comments
AnonymousAnonymousalmost 2 years ago

as already commented, hilarious. A real gift for making the impossible appear feasible. A close second to your 'Trapped' which is a comic masterpiece.

AnonymousAnonymousalmost 6 years ago
Why was this story so good?!

It was so good.

puncturepuncturealmost 9 years ago

What a fantastic story. Kept me amused and erect

cowboy109cowboy109over 12 years ago
Hilarious!

That was absolutely hilarious. The tone brought everything over the top.

AnonymousAnonymousover 13 years ago
Fantastic

I have now read all your posts, you really have a gift thanks, you keeps me cumming time and time again,

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