tagBDSMThe Chaperone

The Chaperone


"I've got an important project for you Rebecca," Mrs. Stone said.

Finally, a real project, Rebecca thought. She had accepted a job as Mrs. Stone's PA after becoming unemployed. The pay was good. The hours were horrible. And Mrs. Stone was very demanding. Most managers didn't expect to work personal assistants like they did in the old day. But, Mrs. Stone did. She wanted coffee. She wanted her dry cleaning picked up. Lunch picked up. And on and on. Rebecca was a college graduate. She made 60K per year at her last job...before she was laid off. She wanted a challenge, not to be some sort of glorified go-for.

"Yes, ma'am," Rebecca said eagerly. She had her blackberry in hand and was ready for something a but more challenging. An actual project. Wow. Maybe she could do some editing or even write an article.

"It's homecoming week," Mrs. Stone said. "And my daughter is going. I don't trust kids these days. You should see what they were showing on 20/20 last week. Anyway...I'm putting her in your hands. I want you to chaperone."

Oh no. No no. "I'm sorry Mrs. Stone, but I already have plans for Friday night. I'm going out of town with my fiancee Mark this weekend."

"Well, you'll just have to cancel." Mrs. Stone said. "Besides, I'll pay a rosy bonus. There are no no's here. You will chaperone. If you don't want to work for me, you can find someone else to do the job, but you will be doing this on Friday night."

Rebecca wanted to tell the old bat to go to hell. To fuck herself. She also knew all about Mrs. Stone's idea of a rosy bonus....ten or twenty dollars. But she needed the job. And the insurance. She swallowed her pride once again. "I-I'll do it."


On Friday night, Rebecca pulled up to the expensive house in her blue Corolla. She felt sorry for Mrs. Stone's daughter. The poor girl going with a chaperone. She could only imagine what it might be like living with a controlling battle ax like Mrs. Stone. She walked up to the expensive house and rang the doorbell.

A few moments later it was opened by a balding man with darting fearful eyes.

"You must be the chaperone," he said. "Please come in."

Even before Rebecca entered, she could hear the screaming.

"I will not have a chaperone! You can go to hell!" screamed a shrill voice.

"Yes you will," said Mrs. Stone's familiar voice. "Or you'll be staying here. No game. No parties. And no trouble."

"Fuck you!"

"You will not use that type of language young lady," Mrs. Stone said.

"Fuck you fuck you fuck you!" she screamed louder. "And fuck your chaperone too."

"You better go." Mr. Stone whispered. "It will just get worse if you keep them waiting."

Rebecca noticed he stayed hidden in the foyer while she walked in to the living room.

"Oh Jesus!" said the young blonde, pointing at her with an accusing finger. "Is that her? Look at her. She's fucking old! What is everyone going to say?"

I'm only 29 Rebecca thought, but kept her mouth shut.

"She's a young thing," Mrs. Stone said. "She's 23 or 24 I think. Anyway, she's going to be your chaperone and that's final."

"I'm eighteen mom!" the young girl said. "I don't need a fucking babysitter!"

"Yes you do. Just tell people she's your cousin from the East Coast," Sharon suggested.

"And she just happened to want to go to a dance," the young girl said. "Without wearing a party dress...she'll look like a retard. And I'll look like someone who hangs out with retards!"

Mrs. Stone cast Rebecca an accusing glance. "I told you it was a party. Where is your dress?"

Rebecca shrugged her shoulders. "I did dress." And truly she did. It was suitable for the sort of occasions she would go to.

The young girl seized her her weakness. "She can't go like that mom. She can't. She looks like an old bag. An old office bag."

Mrs. Stone looked from one to the other. Then back to the one who didn't fight back. She took out $100 from her purse and handed it to Rebecca. "Make it happen." she said.

Gwen snatched the bill from her fingers. "$100?" she demanded. "What the fuck can she buy for $100 mom? Your purse costs 5 times that."

"Never mind my purse young lady," Mrs. Stone said. "Digging into her purse she fished out 3 more bills."

Gwen shook her head and kept out her hand until it was joined by two more fifties.

"Okay," Gwen said. "That'll have to do. And I guess you will to." Rebecca glanced up and down the young PA, and then she put the money that was destined for Rebecca in her tiny Coach purse and walked outside.

"And you," Mrs. Stone said to Rebecca. "You better make sure nothing happens tonight as far as my daughter is concerned. Or being fired will be the least of your worries." She went outside to meet Gwen, who was now on the phone.

"....I heard about your troubles. Listen, you will not believe what my mom has done. It's horrible, I'll tell you all about it when we get there. Yes, we. I've not only got you a date, but I've got money for anything you might need. Are you up for it? Yes, she's pretty. We'll swing by and pick you up. And we'll be early. I owe you a big one. But I think you'll like this in the end. Ciao."

Gwen put the phone in her purse and then tossed Rebecca her keys. "We are not driving that piece of shit." she said.

Rebecca took the keys. Her car wasn't a piece of shit. It was a perfectly serviceable vehicle. Sure it wasn't nice like Gwen's car, but Rebecca didn't have Gwen's rich mom to rely on either.

"I'm not sure about this date business I heard you talking ab out on the phone," Rebecca said. "I'm supposed to be your chaparone, not your friend."

"Look," Gwen said. "You can forget all about ruining my homecoming night. I mean forget it bitch....I will fuck you so bad you want be able to walk for a week. Now, you are going to be my cousin from Boston. And I'm setting you up on a date."

"I can't go with a date," Rebecca said. "See - I'm engaged."

"Sush," Gwen said. "Everything is under control. It won't be anything like that. I've got you a girl date to hang out with. Now give me that ring."

"Well...." Rebecca said. "I guess that will have to do." It wasn't a real date at all. Just someone to hang out with. And it was a girl, so she wouldn't get the wrong idea. Actually, things were looking up. But the ring. No, she couldn't just hand it over. Not to someone so irresponsible and crude. She took it off and put it in her purse. They picked up Gwen friend, Lisa and then went to the mall to shop for homecoming dresses for Lisa and Rebecca. Gwen ushered the two girls into a dressing room, and said. "Go ahead and get undressed, I'll bring over some gowns for you to try on."

"I'd rather look for myself if you don't mind," Rebecca said.

"Oh come on," Lisa said, already shrugging out of her shirt and unbuttoning her pants. "It'll be fun!"

It could be fun trying stuff on that she didn't pick out. And she had such a hard time finding things that matched. But, she had a nagging thought that finding a homecoming dress for a 29 year old might be much different than finding one for an 18 year old. Soon she had shed her clothes and stood in her panties and bra.

Lisa, however, was completely naked. It made Rebecca feel a little uncomfortable being cooped up with such a very young and naked girl in the small confines of the dressing room only designed for one person.

"What are you doing?" Lisa asked. "You can't wear a party dress with bra straps and panty lines. Everyone knows that."

Apparently everyone didn't know that. Rebecca had worn a strapless bra and panties for her homecoming game.

"Are you shy or something?" Lisa asked, and she was already behind Rebecca undoing the clasp of her bra. "It's okay. Don't be afraid, I won't laugh."

"I'm not afraid of..." Rebeccca began and then her bra was off.

"Awww...they're so cute," Lisa said. "See, I told you there was nothing to be afraid of. Anyway, I always feel like mine are in the way...and it makes me feel weird when it's all the boys can seem to look at."

Rebecca's cheeks bloomed a rosy red. This was exactly the sort of reaction she had feared the most. She hated being simply cute. It brought back all her terrible memories from highschool. Being judged by boys...and girls. She couldn't help her size. And worse, now she was 29 and here was this eighteen year old. Already more developed. And patronizing her because of her cup size. She moved her hands up to hide them.

But left herself more exposed down below, the precocious girl had hold of her panties and was pulling them down!

"Wow!" Lisa said, her hand lingering on Rebecca's abdomen. "I'd kill for your stomach. How do you do it?"

Rebecca wasn't only lean up top, but lean in the middle and narrow of hip. She had always been proud of her figure in that respect.

"I work out some," she said, but the truth was she was that way naturally.

"I like your butt too," Lisa said her hands moving over Rebecca's tight buns.

Why did the infernal girl need to touch every part of her. She was so touchy touchy that Rebecca was becoming uncomfortable. She wished Lisa would hurry back. What was taking so long?

"Do you think I'm pretty?" Lisa asked.

Rebecca looked at the young girl jealously. She had full breasts that managed to defy gravity. Her stomach wasn't lean, yet she managed to be round in all the right places. And her skin was soft and smooth the way only an eighteen year old's could be.

"Yes." Rebecca admitted.

"Do you really think so?" Lisa asked, moving even closer. So close her nipples grazed Rebecca's.

"Yes." Rebecca said backing into the corner. She could go no futher and Lisa didn't seem in any hurry to move away. Thankfully, Gwen came back and tossed Lisa a gown. And one for you too," she said, tossing another Rebecca's way. "Hurry up girls, we don't have all day."

"Help me with this," Lisa said, handing her gown to Rebecca.

The young girl wasn't much help for dressing herself, Rebecca thought. She had to kneel down to get her to step into the sheer fabric. And the more of her she got into the gown, the more it became clear this gown wouldn't do at all. It was much too tight. She had to practically stuff her in it and touch more parts of her than she would have liked.

"Hot or not?" Lisa asked.

"It's too tight," Rebecca said. "If you move the wrong way, you'll bust out."

"So, it's too hot?" Lisa asked.

"Yes." Rebecca said.

"One size up," Lisa told Gwen. "Now let's try yours." Taking hold of Rebecca's gown.

"I can manage." Rebecca said.

"Stop being a pussy and let her help you," Gwen said, taking Lisa's gown out to find another. She also took more than the older woman bargained for, taking her discarded clothes and her purse.

Rebecca was way too concerned with the way Lisa was handling her. Forcing her into the too tight gown.

"It's way too tight." Rebecca gasped.

"Suck it in." Lisa said. "I've almost got it."

And there she was breast to breast, body to body, with this young eighteen year old girl. Hands with a firm grip on her ass. Trying to wedge her in gown much too small. But she got her in it. Shoe horned her right in. Touched her in more places than she cared to remember. But there she was, in front of the mirror. The bottom of her thighs bulging from the gown, already small breasts turned from peaches to grapes.

"God you look ridiculous." Gwen said from the door. "I'll be back with another. Here Lisa. Try this."

Gwen tossed in a new gown and two pairs of heels. Rebecca helped Lisa dress again. The result was much improved. This gown was much better than the last. It was green, but the only problem was the girls breasts. They hung full in the gown and every ridge and bump of the girls half-dollar sized nipples were on display.

"What do you think?" Lisa said.

"It's pretty," Rebecca said, but still her eyes were drawn to the girl's breasts. "But maybe a little too revealing without some sort of padding."

"I like it." Lisa said with finality. "I like the way you look at me when I'm in it."

But it wasn't the way Rebecca was looking at her that she should be worried about. It was how boys would look at her - with hungry eyes and lustful thoughts.

"Nice," said Lisa from the door tossing Lisa a white bit of cloth. "Here, try this one on Becky."

"Wow, this is nice fabric." Lisa said. "Let's get you in it."

"There isn't much to get into," Rebecca noted. Thankfully, that meant that it was easy enough to put on and she didn't have to be handled by the overly touchy Lisa.

When she looked in the mirror, it was clear this dress wouldn't do at all. First of all, it was white and thin. It was more babydoll than gown. There was a circular gold clasp that held it together above her chest. However, her shoulder and back were exposed. And so was the better part of her thighs. And the fabric Lisa liked so much. Were it touched her, it molded itself to her. Small cone shaped breasts and hard nipples were displayed. So short. One false move while sitting, and God, she didn't want to think about it.

"It's beautiful," Lisa said.

"I can't wear this...besides it's too much," Rebecca said after taking one look at the price tag. Way too much.

And it wasn't just the price that concerned her, but on her it looked practically obscene. She told Lisa so. "I can't go in this. It's indecent."

"Really?" Gwen said, listening from the door. "Don't tell me what you will and won't do. That's exactly what you are wearing. Let's go."

"No way," Rebecca said. "Give me my clothes and I'll pick something out myself."

Then she noticed her clothes were gone. Where were they? What had been done? She began to panic. Panic turned to terror when Gwen pinched the hem of her gown and pulled her out of the dressing room.

"Come on Becky," Gwen said. "Or do you want to show all these people that cute little pussy."

"Stop it Gwen. I'm not playing." Rebecca said stumbling along after. "Let me go."

And the further she was drawn from the security of the dressing room, the more imperative it became to keep up with Gwen - pulling her along by the hem of her skirt. Leading her like a dog or some sort of errant child. It was embarrassing. Humiliating. She could feel the silky fabric tickling the swell of her bottom. Good Lord. Forced to walk along obediently in her high heel shoes. Forced towards the door.

"Wait," Rebecca said, with increasing panic. "We haven't paid."

"We aren't going to pay." Gwen said.

"No. Where are my clothes? Where is my pocket book?"

"In the trunk with Lisa's," Gwen said. "Now keep up and keep quiet, or you'll show off that little pussy."

"This is serious," Rebecca said. "Gwen. Stop right now."

But she didn't. She just laughed and kept pulling her by the hem. Pulled her out the door and to the car.

"Hurry up," Lisa said, urging Rebecca in the car. "Let's get out of here."

And then Rebecca was in the car. In a stolen dress and pumps. Good Lord! Some job she was doing of being a chaperone. She resolved to do better. To not let herself be compromised again.

"Gwen," Rebecca said. "Stop the car right now. We are calling your mother."

"Relax," Lisa said. "Aren't you looking forward to tonight? Besides we couldn't have afforded these dresses. And yours is so hot."

The touchy girl again. Rebecca felt sorry for her naiveness but not for her touchiness. Her hands touched her dress and even her body where she didn't want to be touched.

"But it's wrong to steal- stop that," she took hold of her hem and covered her crotch where Lisa had accidentally exposed her.

"Sorry," Lisa said. "Did you see the look that man gave you when he saw your bare ass? I thought his eyes were going to bug out of his head."

Rebecca shifted in her seat uncomfortably. She had seen and she shuddered at the thought. But it wasn't her choice. "I didn't show him. Lisa did."

"I was watching from behind," Lisa said and then her hand was on Rebecca's thigh again. Rebecca took hold of her hand to move it down, but the girl's fingers encircled her own and held her fast. "You are so hot."

Rebecca wondered just what was going through Lisa's mind. She didn't want to hurt her feelings, but she didn't like the way she touched her. But she let her hold her hand. It was a better alternative than fending off those groping fingers.

They stopped at the high school and went to the game. It was a cool night and Rebecca was wearing next to nothing. She was cold. And so was Lisa. Gwen was wrapped up in a blanket on the bleacher in front of them with her boyfriend.

"Do you have an extra blanket," Lisa asked Gwen.

"Give them your coat honey," Gwen told her date. A big blonde boy named Brad, with agray lettermen's jacket. He took it off and handed it back to the girls shivering from cold. They took it gratefully and cuddled inside for warmth. For once Rebecca didn't mind being so close to the young girl. Everything was going well for a change, at least until half-time when Lisa and her date began making out.

"I bet if we did that, we could keep warm." Lisa whispered.

"I don't think that's a good idea," Rebecca said.

"Just a little," Lisa said. "Please. I'm so cold. Just tell me if I make you feel weird."

Then she gave Rebecca a peck on the cheek and a reassuring hug. She had been making Rebecca feel weird all night. But this wasn't so bad. It was kind of sweet.

Then she gave her another kiss on the cheek. Then another. Then one on her neck. Then her ear. Rebecca could feel herself begin to get turned on despite the fact she was being kissed by a girl and it scared the devil out of her. She opened her mouth to protest and it was quickly filled by an eager tongue while a hand caressed her breasts and moved between her legs. She finally managed to pull back and gasp for breath.

"That's enough," Rebecca gasped.

"Was it too much?" Lisa asked. "I'm sorry."

Thankfully, Lisa stopped trying to make out with Rebecca. But the respite was short. Lips touched Rebecca's bare shoulder. And then the nape of her neck. Rebecca tried to ignore the sensations. She should have been able to ignore them. This was a girl. A girl 11 years her junior. But somehow she could feel herself responding. Responding as she did for her fiancee. Getting warm. Getting tingly. Getting wet.

By the end of the game Rebecca had to tell Lisa to stop at least five more times. She had even begun to allow the young girl to nuzzle her neck and kiss her on the lips provided there was no tongue involved. Had even allowed her to touch her wherever she wanted as long as it was through her clothes and not beneath it. It was easier than fighting her off. Besides, there was no where to go. She had no purse. No keys. No suitable clothes. And she wasn't going to give up the warmth of the small coat. And it was now considerable warm inside of its confines. It would have been cruel to have kept it all to herself and left Lisa to fend for herself. However, one thing had become very clear. Lisa liked her. LIKED her in THAT way. The way a boy likes a girl. As they walked back to the car to go to the after party, Rebecca was practically staggering in her heels due to the effects of fending off the young paramore's advances.

"You girls have fun?" Gwen asked in the car. This time her boyfriend Brad road in the passenger seat. "I didn't see you watching the game very much."

"It was nice," Rebecca said, not wanting to go into details. She had observed what was going on under Gwen and Brad's banket. Heard Gwen's gasps of pleasure. Nothing much happened, but once again she hadn't done her job. What if something had happened? However, she had her own hands full with Lisa and the crush she appeared to have on her.

"It was nice, wasn't it Brad," Gwen laughed and so did Brad.

Soon, the arrived at their destination. A large brick house in with cars all along the street.

Report Story

byCouture© 8 comments/ 55869 views/ 16 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: