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The Chaperone

Category: BDMS
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“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.

Inside was packed. Despite trying her best not to lose Gwen, the young girl slipped easily into the throng of young drunks in the house.

Want to dance?” Lisa asked. “Want a drink?”

“No,” Rebecca said moving through the crowd to find Rebecca. She was looking forward to a chance to ditch the young woman.

“What do you want to do?” Lisa asked.

“I need to find Gwen.” Rebecca said. She was determined to chaperone and she wasn’t going to get sidetracked again.

“Why don’t you leave Gwen alone. Besides, she has her hands full with Brad,” Lisa said, taking Rebecca and pushing her against the wall. “And you have all you need right here.”

Then she kissed her again. Her tongue dancing against the older woman’s tightly clenched lips. But soon they parted, allowing the young paramore to kiss her as she wished. Lisa’s knee moving between slim thighs and against Rebecca’s hot sex.

“No,” Rebecca said trying to pull away and escape the knee wedged between her thighs.

“What’s the problem?” Lisa asked. “Do you have a crush on Gwen or something? I mean because I can feel you like it. With me.”

“It isn’t that,” Rebecca said. She couldn’t tell this girl that she was engaged. Couldn’t tell her that she was too old for her. Not now. After all this. But the girl was right. She was hot. She could feel her juices on Lisa’s soft knee. “I’ve just go to find her.”

Rebecca pushed Lisa away and then fled before something bad happened. A good thing she did to. She found Gwen in the living room dancing. One boy in front of her and one behind her. Humping against her. Brad nowhere to be seen.

“Stop that,” Rebecca said, pulling Gwen from between the two boys. “I swear I’ll tell your mom.”

“Hey boys,” Gwen said ignoring Rebecca. “She said she wants to take my place.”

And then the were on her. Humping from the front. Humping from the rear. She felt like she was in a sandwich she couldn’t escape. Then the one in the back started smacking her ass. She tried to pull away but every time she tried to pull away he pulled her back with her gown. It was all she could do to keep from being exposed. Thankfully, she saw Lisa and waved. “Help.” she mouthed.

An angry look crossed Lisa’s face. She hurried over to the helpless woman and pulled her away from the guys.

“She’s with me,” she said and pulled Rebecca in close.

Rebecca was grateful. She was even okay with being held so closely. She glanced toward the boys. They looked reluctant to let her go. And then Lisa pulled her tighter and kissed her. Her tongue dancing inside her mouth. This time Rebecca let her. Melted in her warm embrace. Hopefully, the boys would get the message. It looked like they had.

“Dance with me,” Lisa said.

Body to body. Lisa’s knee between Rebecca’s and Rebecca’s likewise. They moved in time to the beat with Lisa leading. Sensual movements. Sex quivering with pleasure. She could feel her juices leaking. Could feel Lisa’s on her knee. Back and forth. And around and down. Could feel Lisa’s hands on her ass. Kneeding her firm cheeks. Rebecca reached back, took the pawing fingers and placed them at the small of her back. They danced more and the hands moved back down. Squeezing her. Owning her. And the knee. Back and forth. Rubbing her. Bumping against her. For a minute Rebecca didn’t think about what she was doing. Who she was doing it with. Her fiancee. Her job. Nothing but the feelings running like electricity through her body.

When the song ended, so did the moment.

“Sorry, I’ve got to go.” Rebecca said. “I need to find Gwen.” It wasn’t easy to escape the knee wedged between her thighs or the hands pawing her ass. But soon she was free, and then she left Lisa on the dance floor by herself.

She found Gwen in the bedroom. On the bed. Her gown pulled down from her shoulders. He held her hair from her face. Lips parted. A hard prick filled her mouth. Her head bobbing up and down on Brad’s lap. Slurping noises escaped her young lips. Brad moaning “Fuck yeah, fuck yeah. Suck my cock babe.”

“Gwen,” Rebecca said. Jesus, look what she had allowed to happen. Mrs. Stone’s daughter had performed oral sex on a boy while she was in her charge. “Stop that right now. We are going home this minute. Get your things.”

“Oh that’s it,” Gwen said. “It’s on now.” She moved in a flash. Struck like a rattlesnake. Not even bothering to pull up the top to her gown she grabbed her purse and Rebecca’s ear. Pulling the older woman down, hunched her over, and then led her by her ear to the attached bathroom. Once in, she surveyed the bathroom, looking for something, then her eyes narrowed in certainty as they spied a hairbrush left on the counter.

“Perfect.” She picked up the brush and pulled Rebecca down to the toilet. Flipped the short gown up and leveled a blow, the flat of the brush landing with a resounding smack. Then she landed a blow to the other cheek. Two red marks left in her wake.

“Stop. What are you doing?” Rebecca cried. “Ouch! Jesus! Ouch!”

But Gwen was just getting started. Whap. Whap. Whap. “I told you not to fuck with me, didn’t I? Didn’t I?” she said. Whap. Whap. Whap.

Rebecca was appalled. How could this have happened? She was helpless. Totally at the whim of this young eighteen year old girl. She tried a new tact.

“Stop it. Or. Ow. Shit. Stop, or I’ll tell your mother.” she said.

“What will you tell her?” Gwen said. “That I sucked Brad off? That I spanked your ass? That you played touchy feely with Lisa? Oh please do. I’m sure that’ll go over really well.” Whap. Whap. Whap.

“I’ll-I’ll-Ouch!” Rebecca cried. What would she do? What could she do? Gwen was right, the truth wouldn’t do at all. And soon the pain became too much. “Ouch. Please stop. Please.”

Rebecca’s legs splayed kicking helplessly. Her high heeled pumps uselessly trying to find purchase on the tile floor. She reached her hands back to deflect the blows.

“Get those hands out of the way,” Gwen warned. “Or I’ll use the bristle side.” Then she did. Just to let Rebecca know how it would feel.

“Please Gwen,” Rebecca whined. Those bristles hurt. Shit they hurt. Tears now flowing from her eyes. “I won’t bother you anymore. Just stop.”

“It’s too late,” Gwen said. “Besides, I’m enjoying this too goddamn much. Now get your hands down. Get them down and I won’t spank you so hard.”

Reluctantly, Rebecca moved her hands from her ass and put them on the stool. She was thankful to be able to get her body off of it. Who knew who had been on it? Or how clean it was?

“Now stick your ass out for me.” Gwen said.

The older woman had curled under to escape the blows….she slowly moved her ass back up.

“Get it out there,” Gwen warned.

Biting her lip, Rebecca arched her back, bringing her bottom up and out. Into the perfect position.

“That’s a good girl,” Gwen said. “Now I’m going to let go of your ear. Don’t try anything or I’ll burn that ass up – bristles and all.”

The urge was compelling when Gwen let go. Almost overpowering. Rebecca wanted to jump up and run. But she had a good feeling she would end up in the position again. And as bad as her ass was stinging – she couldn’t bear the thought of another blow from the bristle end again.

Thwack. Gwen landed a light blow on Rebecca’s firm lean ass. And though it wasn’t hard as before, it wasn’t exactly soft either. Thwack. Thwack. Thwack. She made sure to cover each and every inch of the ivory moons with red welts. While each blow wasn’t as painful as before, they began to add up to a whole much more than the sum. A whole lot of pain. Rebecca’s chin began to tremble. Tears began to well. It wasn’t just the pain – it was that this was being done by a girl 11 years her junior. A girl who had been placed in her charge.

“For the rest of the night, if I want to dance, what are you going to do about it?” Gwen said.

“Ouch. Nothing.” Rebecca whimpered.

“What if I want to drink some beer?”

“Ouch. Nothing.”

“If I tell you to get me a beer.”

“I’ll – I’ll get it.”

“What if I want to fuck? What will you say?”


“Damn right. And what about Lisa?” Gwen said. “You are supposed to be her date. Where is she?”

“I don’t know,” Rebecca sniffled.

“Well that is going to change,” Gwen said. “If I see you tonight, I want to see Lisa too. If I see Lisa, I sure as hell better see you. Understood.”


“I mean attached to her, understood?”

“Yes. Please stop. Ouch.”

“I don’t think you do understand,” Gwen said. “I told her she might get lucky tonight. I want you to make sure she is.”

Rebecca didn’t understand. How would she make sure that happened? She couldn’t very well find a guy for her and stand there while they did it. And then so much of tonight made sense. She would be the one showing Lisa the way. They would do it. Dear Lord no!

“I can’t.” Rebecca said. “I’m engaged.”

“Don’t worry I won’t tell,” Gwen said. “-if you do it. But if you don’t. There’s a lot I could tell.”

“Please…” Rebecca pleaded. “I’m not that way. I don’t even think I could.”

“I guess I will have to teach you then,” Gwen said hiking up her skirt and taking seat on the toilet. “The things I do for my friends….”

Rebecca looked up at the blonde haired girl , her legs spread, her eyes stern.

“Get to it.”

“I don’t know how…” Rebecca said. She didn’t get to finish. Gwen was back up and had the brush again. Thwack. Thwack. Thwack. Thwack.

“Tell me when you are ready,” Gwen said and proceeded with the spanking. It didn’t take long.

“Okay, I-I-I’ll do it.” Rebecca said.

“That’s my girl,” Gwen said. “Are you sure?” And continued to spank. Thwack. Thwack. Thwack.

“I’m sure.”


“Yes. Ouch.”

“With sugar and Lisa’s cherry on top?”


“Are you ready to put out for me?”


“You ready to show me what you will do for my friend Lisa?”


Gwen sat back down on the stool. “Get to it.”

Rebecca looked at it once more. I triangle of damp dirty blonde hair and a slit. She stuck out her tongue and licked.

“Mmmmmmm….” Gwen said. She was already horny even before dragging Rebecca to the bathroom, and after the spanking, her desire had only increased. The tongue grew more persistent. Licking her lips. Stroking her clit. “Lick my pussy. Oh lick it you old bitch.”

Rebecca licked it. She sucked it. Had her pretty face rubbed in it. There in the cramped bathroom. On her knees. Her ass throbbing. Her own sex wet and lusting. She didn’t know what was worse, doing this, or her own body’s betrayal.

“Faster little queer,” Gwen said. “Don’t make me spank you again. You know I will.” Part of her was incredibly turned on by dominating this older woman. However, another part couldn’t help thinking that this was a woman between her legs. Not a man. Not Brad. She began to grow frustrated. “Faster. Faster. Lick it right.”

Rebecca obeyed. But it was no use. It wasn’t working for Gwen.

“You’re useless,” Gwen said as she stood. “I have half a mind not to give you to Lisa at all. She’s too good for you.”

Rebecca’s heart soared. Maybe this would be the end of her ordeal.

“Maybe I should give you to the basketball team instead.” Gwen said smiling. “Hope you are on the pill.”

“No please,” Rebecca was horrified at the thought.

“Please what?”

“I want Lisa,” Rebecca pleaded. “Only Lisa.”

“You’ll do like she says?”

“Yes. Oh yes.”

“Good girl. Now, I want you to pretend I am Lisa,” Gwen said, pulling her gown back into place “What do you say to me?”

“I want to – I want to make love to you.”

“I think you need to work on your delivery,” Gwen said fluffing her hair in the mirror. “Try again. Talk dirty to her. Say you want to taste her pussy.”

“You’re so pretty,” Rebecca said. “Please let me kiss your pussy. Let me make love to you.”

“That’s better.” Gwen said. “And say that you will do anything she wants. Anything.”

She took out her cell phone and called Lisa.

“Hey Lisa.” Gwen said. “Where are you? I have Becky here in the bathroom. There’s something she wants to say to you.” And then she handed the phone to Rebecca.

“Hi Lisa,” she said. ” I wanted to tell you. I wanted to tell you that – that you’re pretty and I want to – to make love to you. I want to taste – taste your pussy. And that I’ll – I’ll do anything – I’ll do anything you want.”

“Anything?” Lisa said seizing on the word.

“Anything.” Rebecca repeated.

Seconds later Lisa knocked at the bathroom door. Gwen let her in. Lisa’s eyes widened in shock. This wasn’t quite what she expected. Rebecca was on her hands and knees. Her ass was a blaze of red welts. Her face wet and damp with sex.

“What the hell?” Lisa exclaimed. “What have you been doing? Tell me?”

“Nothing.” Rebecca lied.

Lisa seized the brush. Whap. Whap. Whap. These were hard blows. Hard blows on a sore tight ass.

“I can smell it.” Lisa said. Furious. Her date had cheated on her. Teased her. And then played her for a fool. Promised her anything, but then given it to someone else.”Tell the goddamn truth.”

Spanked again. Hard. Her already sore ass exploding in pain. Dominated by Gwen. And now again by this girl who had been so sweet – who thought she had cheated on her. It was too much. The dam broke and the truth spilled.

“She made me do it.” Rebecca said. Why hadn’t Lisa stepped in. She had obeyed. And now she was being punished again. It was too much. “I swear. This wasn’t supposed to happen. I’m not her cousin. I work for – I work for Gwen’s mother.” And she kept going. Telling Lisa about Gwen’s mother. Her job. Being forced to chaperone her young charge. Playing along at being her cousin. Even of her engagement. It all came out.

Lisa was dumbstruck. Now so much made sense. She looked at Gwen. Then down to the whimpering woman kneeling on the stool.

“Why didn’t you tell me earlier?” she asked Lisa.

Lisa shrugged her shoulders. “I was embarrassed that my mom sent me with a chaperone. And then – well…I know you haven’t been able to find anyone at school and I practically handed her to you on a silver platter. You’re too nice sometimes…” she accused.

“Maybe I am too nice,” Lisa said reaching into her bag and handing Gwen a digital camera. “But I’m just mad you didn’t tell the truth. You almost made me miss this chance.”

“What chance?” Gwen asked.

“You’re being too shortsighted.” Lisa said. “Lock the door.”

They say that the truth will set you free. But at those words a bolt of fear stabbed through Rebecca’s soul. She had told the truth, but she wasn’t free.

Lisa wiggled out of her gown. Her eyes were as hungry as a predator’s. “You said you wanted to taste my pussy.”

It was Lisa’s first time with another girl. While Gwen wasn’t into girls, Lisa was. And it showed. Rebecca found it much different with someone who enjoyed it. Who got off on it. Putting her through her paces.

First Lisa sat on the toilet like Gwen had. Relaxing. Enjoying. Then she pushed Rebecca down to her back and sat on her face until the poor woman gasped for air. Then she crouched down a little under a foot separated her sex from Rebecca’s tongue. She stuck out her tongue, thinking Lisa would move back down. When she didn’t she tried to bring her head up crunching. Her stomach trembling…she was almost there. Lisa smiling down at her.

“What are you waiting for?” Lisa said. “Lick me. You’ve got me so hot.”

Rebecca struggled up. Finally she made it. Licking. Sucking. Flash. Flash – more pictures were taken. Then Rebecca moved once again. She turned around making Rebecca lick her from behind. Flash. A picture. And then three. Made her lick her from the bottom. From the top. Made her lean against the toilet, her head hanging up over the bowl and lick her. “Oh like that. Like that. Faster.” Lisa said.

Poor Rebecca. It was a terribly uncomfortable position to be in. The bowl cut into her back. She was forced to hold her head up with her neck muscles because the seat was up. Her hair dangled into the water below. She flicked her tongue faster. Faster. Eager for this to be over. And there was Gwen, always with the infernal camera in her face. Flash. Flash. Jesus. God.

“Fuck. Fuck.” Lisa gasped, hips pumping, coming, her fingers pinching the older woman’s nipples like a vice.

Finally over. Or so Rebecca thought.

But then Lisa made her get up and pose for more pictures.

“Show me those little perkies,” Lisa ordered.

Blushing Rebecca lifted up her pert plums. Flash flash. More pictures.

Then Lisa took her glasses from her bag, put them on and made a show of looking for Rebecca’s breasts. “Where are they?” Flash. Another humiliating picture.

Rebecca wanted to crawl into a hole. At least until Lisa bent down and suckled on Rebecca’s hard nipples, sending bolts of electricity through her body.

“Now, let’s see that pussy.” Lisa ordered.

And Rebecca was made to get on the floor and spread her legs. Like a whore. Flash. Flash. The camera recording her every humiliation.

“Let’s see inside.” Lisa said.

Rebecca was made to part her lips.

“One finger from each hand.” Lisa said. “I want you to stick them in and pull that little cherry apart. I want to see inside.”

“Please….no” Rebecca begged. This was too much.

“You want me to show these pictures to Mrs. Stone?” Lisa said. “Or your fiancee?”

God no. An index finger was inserted into her dripping pussy. And then another. She rocked back as she spread her legs. Then she pulled apart.

Flash. Flash.

“This is disgusting.” Gwen said, taking another picture and wrinkling her nose in distaste.

“I like disgusting,” Lisa said. “Get a picture of her insides.”

Flash. Flash.

“Now turn over.” Lisa said. “On your hands and knees.”

“Good girl.”

“Kiss my feet.”

“Put my toe in your mouth.”

When would it end? Rebecca took the big toe in her mouth and sucked.

“You’ve been a good girl, haven’t you.”


“You’ve done everything I’ve asked.”


“Would you like a reward?”


“Would you like me to fuck you with this handle?” Lisa held up the brush. The handle had ridges to grip. It was quite big around.

“Yes please,” Rebecca said. Despite her mistreatment. She was hot as a firecracker. She needed it.

“Spread your legs like a good slut.”

Rebecca spread her legs and arched her back. She needed it now. Wanted it. She had endured so much. She deserved this.

Lisa was happy to oblige.

“Damn you’re tight.” Lisa said, working the handle into Rebecca’s hot pussy. “Your fiancee – he do this to you?”

“No.” God no. But Rebecca had to admit each and every ridge of that handle was delightful. Opening her over and over again with each ridge. So big. So hard.

“Thanks. Gwen.” Lisa said. “Hand me my camera back.”

Gwen looked at it reluctantly. She owed Lisa a favor, but with this evidence she could not only have Rebecca on a string, but Lisa as well.

“Don’t worry,” Lisa said. “I’ll be sure she will be your chaperone anytime you need her. Anytime. Anywhere. A pet chaperone.”

Gwen wasn’t interested in women sexually. But it would be nice to have a chaperone – a pet chaperone. She handed the camera over and left the bathroom. It was thick with musk and she was ready to get out. More than ready to find Brad again.

“And now you,” Lisa said, turning her attention to Rebecca. “I’ll have a little pet too, now won’t I?”

Lisa pulled the handle from Rebecca’s sex and pushed only and inch in. In and out. Teasing her.

“Yes.” Rebecca admitted.

“These pictures, they could ruin you couldn’t they?”

“Yes.”: God yes.

“How old did you say you were?”


“God this is so hot.” Lisa said. “I want you to dump your boyfriend.”

Not boyfriend. Fiancee. The scene went through her mind. The dinner. Then ring in the champagne glass. He asked. She said yes. She had even booked a church and minister. Was looking at dresses just last week. But last week felt like ages ago.

“Please don’t.” Rebecca begged.

“Should I send him some pictures?” Lisa asked.

“Okay. I’ll – I’ll do it.” Rebecca had no choice. She should feel like crying. Yet all she felt was hotter and hotter.

“Besides, you’re going to be too busy being my girlfriend.” Lisa continued. “But we can’t see each other if people find out you are so old. Oh, I know we’ll do. You’ll tell people you are my little college girl, won’t you?”

God, Rebecca remembering high school. Remembered being jealous of one of her friends who dates a mature college freshman. Now she was the freshman. Only she had graduated college years ago.

“And you are going to have to start dressing different,” Lisa said. “No more business clothes … if you are going to be my college girl, you are going to have to start dressing like one.”

“I think you can imagine what I like.” Lisa said. “Short tight. So very tight.”

And by then she had the whole handle in. Fucking her. In and out. Long smooth strokes. Wet sounds echoed from the tile walls.

“You going to cum for me? Cuming little slut. My little college tease.”

Rebecca thrust back. Taking it all the way. Coming so hard. Quaking in her soul.

Afterwards Lisa took Rebecca back out to the party and introduced her to her friends. She was much more in control.

“Hi everyone,” Rebecca said to a group of girls. “Have you met my girlfriend Becky? Isn’t she a doll?”

“Hi Becky!” the girls introduced themselves.

It was awkward for Rebecca. She hated being called Becky, always had, and now she was not able to do anything about it. She could feel their eyes judging her. Wondering why she was with this young highschool girl.

“She goes to college.” Lisa volunteered. “Don’t you pet?”

“Yes.” Rebecca blushed. Especially at being called pet. These girls must surely be wondering who was in control in this relationship.

Lisa picked up an empty cup and dropped it on the floor.

“Oops!” Rebecca said. “Pick that up for me, will you pet?”

Rebecca wanted to tell her no. Wanted to have the choice. But the pictures. Cheeks blushing, she bent down and picked up the cup and handed it back to Lisa. She could feel the other girls staring. She could feel her own stock dropping while Lisa’s was rising.

“Thank you pet,” Lisa said, then pulled the older woman in for a smoldering kiss. Then she took her by the hand and led her to the dance floor.

“I think you ran off the last time we danced,” Lisa said. “That wasn’t very nice, was it pet?”

“No,” Rebecca whispered.

“I want you to do it over again.” Lisa said. “Now where were we?”

“Standing right here,” Rebecca said. “Your knee was between my thighs.”

“Then put it back.”

Before Lisa had instigated. Had pushed her knee in between Rebecca’s thighs. Had rocked against her. Gyrated with her. This time, she made Rebecca do the work and she didn’t make it easy.

Rebecca moved in close, her hand on the back of Lisa’s thigh. She extended it, then waddled forward, mounting it. Rocked on it. Back and forth. Oh God. She was growing wet. So wet. And Lisa moved her leg back, turned to the side, snapping her fingers, her eyes in another direction. Not even making eye contact.

But her leg was still out. Lisa moved back in front of her. Snapping her fingers. Trying not to be quite so obvious as she mounted Lisa’s thigh. Rocking on it. Working it. Getting worked by it. Her breathing grew labored. Lisa smiled. And then moved again.

This time Rebecca gave a groan of dismay and growing frustration. She was having a hard time not being obvious. She wanted Lisa. Wanted to dance with her. Needed it. People were beginning to notice. She moved back in front of Lisa again. Moved in close. Put her arms around her. She took Lisa’s hand within her own. Then reached back. Earlier she had taken those hands and moved them. Tried to control them. This time she placed them on her ass. Moved the knee between her thighs. Rubbed against it. Moved her own between Lisa’s. Felt the girl’s hot sex.

“Please,” Rebecca begged.

“The shoe’s on the other foot now, isn’t it pet?” Lisa smiled, her hands taking a firm grip of the smooth round bottom.

“Yes.” Rebecca whispered. A small moan escaped her lips. She kissed Lisa. Sucked on the girl’s plump lower lip.

She knew people were watching. Watching her ride Lisa’s knee. Watching this young girl maul her firm ass through the thin material of her gown. Watching even as she moved her hands beneath the silken material and cupped bare naked cheeks.

“Oh God,” Rebecca moaned.

She rode the knee wedged up between her thighs. Working herself on it. It was slick now. Making it easier to slide on. Back and forth. Lisa was moving against her to. It was hard to stand. Her knees grew weak. A tingling started at her feet and moved up her legs. Higher and higher until it centered there between her thighs. A hot burst of pleasure shooting through her sex. Holding Lisa tight. Groaning and moaning in time to the music. It was one of the best orgasms of her life and Lisa’s too.

After the party, they dropped Lisa off. Rebecca changed clothes in the car and she drove Gwen back to Mrs. Stone’s.

“Did you have fun cousin?” Gwen asked as they walked back to the house.

“Yes.” Rebecca admitted.

“Good.” Gwen said. “I sure had fun. Brad fucked me crazy. And I think Lisa gave you a run for your money, didn’t she?”


And then they were inside the large house. Gwen slammed the door shut.

“Mom,” Gwen screamed. “I hope you are happy Mom! Your little bitch fucked up my Homecoming night!”

“Did you have a nice night,” Mrs. Stone asked pleasantly…ignoring her daughter’s outburst.

“It was horrible!” Gwen shouted, taking off her pumps and throwing them at the wall. “She wouldn’t leave me alone. She wouldn’t even give me enough privacy to talk to Brad in the car! She said I fucking shouldn’t be alone with him.”

“Oh you poor thing,” Mrs. Stone said. “Rebecca, you were supposed to chaperone my daughter. Not stalk the poor thing. I have half a mind to fire you right now.”

“Come her dear and give mommie a hug,” Mrs. Stone opened up her arms and hugged her daughter. Patting the girls back. “There there…”

Gwen shortly went upstairs. Rebecca couldn’t believe her ears. Why wasn’t Mrs. Stone supporting her. Then she was ushered out the front door.

“You did good tonight Rebecca. Matter of fact, I may use you again.” Mrs. Stone said. “Here’s a little bonus for you.”

She handed the younger woman twenty bucks. Rebecca took the money. Twenty dollars. She had lost her fiancee tonight. Had been spanked. Humiliated. Blackmailed. Fucked. Make to suck. Enslaved by an eighteen year old high school girl. All for twenty dollars. Her hands trembled and so did her knees.

“See you Monday morning,” Mrs. Stone said.

She would be a little surprised at what she saw on Monday. Lisa had made plans for Rebecca already. She was coming over this weekend and taking her shopping. Out with the old and in with the new. Good bye professional business clothes and hello short tight college pet clothes. Even for work. God, what would she do?

Rebecca sat down in her car and turned it on. She undid her the top button of her professional pants and the zipper. She worked them down and tossed them in the passenger floorboard. She wasn’t wearing panties. She put the car in gear and pulled away. She took her phone from her purse and hit speed-dial.

“I’ve taken off my pants. Just like you said.” Rebecca said.

“That’s my pet,” Lisa said. “From now on you’re either in short skirts nothing. Is that clear?”

“Yes Lisa.”

“Rub it.” Lisa said. “But don’t get in an accident.”

Moving her hand down , eager fingers quickly found her waiting button. She began to stroke it.

“And no coming without permission,” Lisa said. “Is that clear pet?”

“Mmmmm- yes Lisa.”

“Good night pet,” Lisa said.

“Good night Lisa.” And Rebecca drove to her new life.

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