Mrs Steward Chaperones Chess Team

Editor's note: this story contains scenes of non-consensual or reluctant sex.

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All participants in this story are over 18. This story is about Barbara Steward chaperoning a High School Chess Team of 5 boys on an out of town Chess competition. There is no sex but builds up to a Bukkake. If that's your fetish then this may tickle your fancy. Enjoy. Also, I am very open to constructive criticism and comments both good and bad as that helps me get better. Barbara's husband has already read and approved this story as being accurate to how she would act.

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Barbara Steward sat in her classroom waiting for the bell to ring. She knew what this weekend was supposed to be, and she was a little depressed at what it turned into. She was supposed to have a getaway with her husband Jan for a local getaway. He was going to treat her like they were newlyweds. But what happened was that Mr. Garret suddenly got sick and she was asked to sub in for the chess teams' overnight trip.

When she volunteered as the alternate, she did it because then she wouldn't need to be on another club and there was no way she would ever be asked to do something like this. But now here she was about to have to take five high school boys across the state for a tournament that screamed I'm a virgin to anyone listening.

Barbara looked down at her freshly shaved legs encased in her tan stockinged feet. Then slyly pulled the collar of her loose top open to look down. '$55 on a sexy bra and no one's even going to see it. What a shame.' She thought to herself. The last bell rang for the end of school and she stood from her desk. She looked in the mirror she hung by the door to give the kids a chance to give themselves the once over before diving back into the fray that is High School. "Alright Barb, you can handle five geeky boys, right?" She asked herself in the mirror. Then without giving an answer she wondered about the woman reflected before her.

This woman in her tight navy-blue skirt and gray patterned top with three-quarter sleeves was supposed to be treated like an upscale whore for the weekend by the man she loved and now she's going to look like a soccer mom taking her crew to practice. She shook her head in disbelief and her red hair swayed gently right to left and back. It was cut in a way that frame her delicate face and ended just above her shoulders. "Head up Barb, you've got work to do.

She grabbed her overnight bag and headed out of her class and down the Hall.

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"JERRY, JERRY!" Darrel shouted through the emptying halls.

"WHAT! WHAT!" Jerry mocked back.

"Dude, you'll never guess who's replacing Mr. Garret on the trip this weekend!"

"I don't know, Mr. Bash?" Jerry asked earnestly.

"Mrs. Steward! Can you fucking believe it man? How great is that? I've been fantasizing about her body forever and now it's just gonna be us together on a small trip." Darrel said as he wistfully thought of what this weekend could bring.

"Boys, since it's just five of you and myself we are going to be taking the school's van. Don't be late! And get Mike, Rod and Rick as well. I don't know where they are, but we need to get going." Barbara said as she rounded the corner. She had heard what they said but dismissed it as the empty talk of horny kids. She passed them in the hall and headed for the parking lot where the van was parked. It had the schools name plastered on the side in red letters and the white was now looking beige from how dirty the outside was.

Barbara opened the doors and put her bag in the back of the van then closed the door. As it swung closed, she felt her skirt snag on the door. She looked down horrified to see that her skirt was ripped high up on her thigh. She thought that it was a small rip and as she looked down, she didn't see that it was that noticeable, so she left it alone.

The five boys all arrived at the same time. Barbara saw them joking and horsing around. They were talking in English but to Barbara they were speaking about things she had no idea about. Her husband was a geek and she loved him but like these boys she was bored of what they were talking about and just phased them out. "Alright, load up team. We gotta get there before the sun goes down. I hate driving at night and I really don't want to get pulled over to explain why and old woman is transporting a van of high school kids at night on a Friday night." She said in an exhausted manner.

"Don't worry Mrs. S, all of us are 18 now. Hell, we could go to a titty bar and no one would know or find out. What do ya say? Mr. G would take us." Mike said as he put his bag in the back of the van. Barbara looked Mike over and noticed that he was still a geek but that he had some muscle tone and wasn't bad looking. She felt that he would grow into his looks and be a handsome adult. Possibly even hot. Mike for his part also looked over his teacher and chaperone for this trip.

He knew her from her classes and the reputation that the boys had given her as one of the only teachers that are worth wanking over. He looked down at her skirt and noticed the rip going lengthwise and while it wasn't much, he knew that he would be sitting shotgun with her, just in case it turned out to benefit him and his fantasies.

"Did you think that had a flying chance in hell there Mike?" She asked him sarcastically.

"No, but can't blame a guy for trying to see some tits. I am after all very deprived." He said to her as he glanced down at her breasts. She saw his gaze faltered and felt a little embarrassed by his gaze. She instinctively pulled her shirt up and turned to see if Rod and Rick needed help. They were twin brothers, and both were small in stature and build. They wore glasses and she had often seen them be the butt of jokes from the football team. They seemed to struggle with the size of their bags but both managed to get them in the van. Finally, were Jerry and Darrel. They were best friends from a young age, and this was just another trip for them. Jerry though, did fantasize about Mrs. Steward and how she looked naked.

"Alright, you 18-year-old not adults. Let's get going." She said as she watched the last of the bags get loaded then slammed the back door closed. She then walked to the left of the van and climbed in the driver's seat while the boys walked to the passenger side. They opened the side door, and all climbed in except for Mike. He closed the door then climbed up front with his teacher. "Not sitting in the back with your friends?" She asked him.

"Sit with a bunch of idiot boys or sit with a hot woman ion the front seat? Tough decisions. Plus, you may need an extra set of eyes for navigating." He told her. He looked down at the rip in her skirt while she was busy adjusting the mirrors on the van. He was happy to see that the rip had already begun to slide toward the hem of the skirt and up towards her hip. She seemed to not notice it and started the van and drove away from the school. The van was noisy as the guys in the back were comparing different things and talking openly about the girls in school without regard for Barbara in the driver's seat.

"Guys, do you think a girl wants to hear you talk about how pretty other girls are in front of them? It makes a girl feel ignored and unattractive." She told them as she looked in the rearview mirror.

"Sorry Mrs. S. You're way hotter than the girls in school anyway. Hey, you wanna go out on a date with me?" Jerry said as he leaned over the front bench seat on the van.

"Hahahaha. I think that the school, your parents and the police would have a problem with that. Not to mention my husband as well" She told him as she looked at him in the rearview mirror.

"But you'd be okay with it besides?" He asked her.

She smiled broadly and simply said, "Sure, you're cute enough." Then she laughed loudly. "Except you're too young for me." She finished as she looked at him in the mirror.

"Shame, I have something your husband doesn't have." He said as he sat back in his chair.

"And what's that?" She asked genuinely interested in his answer.

"Stamina and a big dick." He told her frankly.

"Watch your mouth. I'm still your teacher and you can't talk to me like that. Are you looking for detention?" She scolded him and turned her body as she drove to be able to make eye contact with him. This movement caused her skirt to rip further down and she felt the release of the fabric this time. Mike sat calmly in the front seat with his phone directed right in her lap. He was recording her and the way her thigh came more and more into view as her skirt ripped open. Now she looked down and saw the tops of the thigh-high stockings and then tried to hold the parts of the skirt together.

"Mrs. S you're fighting a losing battle. You might as well leave it. I promise not to look until we get there. Your leg looks very sexy though. Your husband is a lucky man." Mike told her as he looked at her exposed thigh.

"It's unacceptable for me to be so exposed in front of you kids." She told him and it got the attention of the others sitting behind them. They began to sit forward in the seats until Barbara told them to sit back and that there was nothing to see, "Mike, could I have your flannel please? I feel so exposed right now." She asked him with pleading eyes. How could he refuse. He would soon have a piece of his clothing smell like his teacher and be rubbing on her thigh for the entire trip. Mark took off his flannel shirt and handed it over to her.

She grabbed it with a shy smile then laid it across her lap until she looked like she was wearing a flannel skirt. As they drove the shirt began to slide and shift and Barbara had to tuck it between her legs and under her ass to keep it in place. Mark couldn't be sure, but he thought the chances were good that it was placed securely next to her panties.

Mark knew the show was over for now and ended his video then emailed it to his friends in the back who all let out exclamations of joy as their phones binged and they watched her thick thigh slowly come into view and her thigh-highs become visible.

The rest of the trip went by without any issues. They stopped a few times, but they were quick, and she protected her virtue with his flannel tied tightly around her which hid the long rip.

When they got to the hotel, they parked the Van and walked into the reception to check-in. They had three rooms and Barbara decided that the rooms would be split up with three boys in one room with two queen-sized beds and two boys in another room with two more queen-sized beds and she would get the single king-sized bed. The rooms were all side by side and after they got the keys they shuffled to the elevator. It was already late, and Jerry asked Barbara if she wanted to get a bite to eat or if they should order take-out. She elected for take-out and told them that she was going to change and head down to the bar for a drink.

Their rooms were on the 12th floor and they walked down the long hall until they stood outside their rooms. Before Barbara entered her room, she untied the flannel around her waist and handed it to Mark that was standing near her. She then looked down at the rip and regarded the severity of it. "It doesn't seem so bad when I'm standing huh?" She asked as she turned her body so he could see it

"Looks downright pedestrian Mrs. S." He told her. Then he watched as she turned back to her door, inserted the key card and entered her room leaving him behind in the hall watching her ass move under the loose skirt.

In her room she placed the bag on the king-sized bed. And took a moment to look around the room. She saw that the room was fairly spacious with a small table for eating or playing cards with three chairs around it. There was a small cushioned chair for reading and the bed that had a side table on each side of the bed. She opened her small bag and pulled out her toiletries bag and brought it to the bathroom where she opened it and organized it for the night.

She saw the coconut oil that she brought in hopes of having Jan rub it all over her with a massage but now she saw it as just additional weight that she was carrying and left it sitting on the bathroom counter by the sink. She then returned to her bag and pulled out a green dress. She also brought the necklace that she thought went well with the dress. The necklace was a choker style with rocks that resembled different colors of sea glass mixed with metal pieces to seem fashionable.

She unbuttoned the skirt she was wearing and unzipped the zipper and let it fall to the floor then pulled the bottom of her shirt until it rose above her head. She then picked both of the garments up and shoved them into her bag. She lifted the dark green dress and pulled it over her head then adjusted it into place and put on the necklace. She knew that she was just get a few drinks, but she wanted to wear the cute outfit she planned on wearing for Jan because she deserved to feel sexy.

Once she felt it was adjusted, she walked into the bathroom and looked at herself in the mirror. She noticed the deep cleavage in the front where it dove between her breasts. 'Jan would have loved seeing me in this. He would want to cum all over my tits. He always does.' She thought as she pulled the neckline out. She then grabbed her phone and took a picture of the cleavage with a message. "Going down to the bar. Hope no handsome men want to cover me in cum!" Then pressed send and before she had time to turn and walk out of the bathroom came a reply.

"I could only wish my dear." Was his response. She simply shook her head and grabbed her keycard then walked out. As she left her room, she saw Mike going into his room.

"Heading to the bar?" He asked her.

"Yep. If I'm not back in an hour wait longer. "She told him and laughed as she passed him.

"Pizzas here guys!" He said as he was entering the room and took one last look at Barbara walking away. The guys all ate pizza and talked about Mrs. S's thigh and those sexy thigh-highs and how they would do anything to see more of her. They watched TV and finished the pizza.

Mike noticed that he hadn't heard a door in the hallway in quite some time and it had already been a few hours. He became a little worried about his teacher and he excused himself from the gaggle of boys and left the room. "I'll be back in a couple minutes fellas." He told them and none of them seemed to notice or care.

Mark walked to the elevator then once inside the car he pressed the lobby button. He hoped that she was alright, but he also hoped that she was drunk enough to accidentally have her tits fall out. When the door opened, he could see directly into the bar area and he saw her right away. She was sitting at a high chair at the bar.

Next to her was a slick looking guy. If he had a spirit animal, it would have been a bottom-feeding snake. As Mike walked towards them, he saw the guy distract his teacher and slip something in her drink. Before Mike could stop her, she drank the entire drink. The guy at the bar smiled a lascivious grin and watched her for the right signs for his next move.

"Hey honey. Sorry I'm late. I got caught up with the boys upstairs." Mike said as he leaned close to her face then whispered in her ear. "Play along, this creep slipped something in your drink." Then he leaned up and called the bartender over to the side and told him the same.

He didn't want the guy to have a chance of getting away and the bartender called security over and allowed Mike to take an already intoxicated Barbara to her room for safety. He told them that if they needed anything that they would get a hold of them later but that they would give the security tapes to the police and they thought that's all they would need.

Mike helped Barbara off the stool, and she wobbled as he balanced her. He placed his hand low on her hip and guided her to the bank of elevators. "You're so cute. If I was your age, I would pin you against the wall and do awful things to you." She told him. Once they were in the elevator she leaned against the wall of the lift. She leaned down far and struggled to remove her heels.

As she was bent over Mike took the chance to get his camera out and take pictures down her gaping dress. Her black lace bra came into view and her breasts seemed ready to escape. Then she looked up and saw what he was doing. "Naughty boy. Tsk tsk tsk. What would my husband say?" She asked but didn't stand up yet. "Did you know I got this bra and the panties for my husband to see? But noooo, that stupid old man had to get sick and here I am with you kids. I should be getting fucked right now." She pouted as she told him things she shouldn't say. "And they came with matching panties, but you can't see them because you're not my husband." She told him as she wagged a finger at him and tried to stand up.

When she tried to stand up, it seemed that the drug took it's affects, and she slid down the elevator. Her legs spread out in front of her and the dress she wore gathered around her waist. Mike took more pictures of the lace see through panties she was showing him. "Not gonna see them huh? You certainly showed them pretty quickly Teach." He said to her unconscious body. He then called his friends and they were standing by the doors on their floor when they opened.

They all say Mike standing over Barbara in the theatre and his hands were inside the top of her dress. "Someone spiked her drink. It looks like it was a knockout drug of some kind. Help me get her to her room." He told them and with all of them working together they were able to pick her up off the floor and get her safely to her room.

Rod went through her small clutch and pulled out her keycard and inserted it then removed it and waited for the green light to enter. Once they made it through the door, they let it close heavily behind them. Barbara was placed on the bed and as they tried to rest her on the edge she fell back, and her legs spread slightly.

Her dress draped enough over her legs to protect her modesty, but her breasts were escaping through the loose neck. The lace of her black bra was showing, and the boys took more pictures. Rick started recording as he lifted her dress up her legs and ran his hand along her thigh. Then he curled his finger inside her panties and pulled them to the side. "She's shaved bald guys!" Rick told them of his discovery.

Jerry looked and saw what Rick did then pushed her dress up to her hips and then grabbed her panties with both hands and began pulling them off of her body. Getting them out from under her butt was tricky but they eventually came free. "Open her legs." Mike told them and Rod and Rick each took a leg and opened her up. Darrel was busy with her top and pulled the neck of her dress further down to expose her right breasts and sucked in his breath as he looked down at her pale nipple with a hard nipple pointing back at him looking for attention.

Darrel slid his finger over her nipple unwatched as her whole breast followed the direction of his finger then jiggled back to where it originally was. "This is the best day ever guys. Let's fuck her. I want to lose my virginity, and this is gonna be great." Jerry said as he quickly took his pants off. His dick stuck out from beneath his shirt and the other guys followed suit except for Mike.

Mike instead pulled Barbara into a seated position and lifted her dress over her head and tossed it into the chair in the corner of the room. Then he unfastened her bra and put that next to her dress. He didn't see her panties, but he suspected that one of the guys would have them as a trophy in his pocket.

Mike then let her fall back on the bed with her legs still hanging over the edge of the bed. "Let's get her more on the bed so she's comfortable." He told the others. They all tried to pull her arms and legs and body up into the center of the bed. Once there, they opened her legs wide and Jerry climbed between her legs and held his cock in his hand as he lined it up with her opened pink pussy.