Jans Wife has to Chaperone a school trip for the Ches club, The boys are 18 and anything could happen. I hope that nothing untoward happens on this trip. Barbara is another one of the wives whose husbands reached out to me to write about. I hope it hits your masturbation bone. No sex but drugging, masturbating and groping


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 ***** 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.


“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 ******* thigh.

“It’s unacceptable for me to be so ******* 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 ******* 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 ***** 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 ****** 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. He could see the moisture around her lips and knew that she was turned on or at least she was pretty recently. As he was about to push into her Mike stopped him. “No! We don’t fuck her. I say that we play and take our pictures and videos, but we stop short of actually fucking someone.” He said while holding Jerry’s shoulder.

Jerry climbed out from between her legs and went into the bathroom to take a breath. When he came out, he was holding a small jar. “What’s Coconut Oil?” He asked as he read the label.

“My mom uses that. It’s supposed to help moisturize the skin. Bring it here.” Mike said. Jerry handed over the jar as the other guys just looked down at their teacher and took pictures of her and videoed her from every angle. “Watch!” He told all of them as he dipped his finger into the small jar and pulled out a small amount of a white semi-hard substance then laid it on Barbara’s right breast and began to massage it around. All of them saw her skin begin to glisten and shine and each of them reached for some of this coconut oil and found different places to rub it into her skin. They paid special attention to her breasts, her inner thighs and the lips of her pussy. Rod and Rick put their faces directly in front of her pussy and smelled in her aroma. They continued to return to the jar until they found it to be empty. Then they looked down at her and Darrel had an idea.

He walked to the side of Barbara and lifted her arm and placed her loose hand around his rock-hard cock then he wrapped his own hand around hers and began jerking off with her hand. While he jerked off with her hand, he used his other hand to play with her slick breast and soon he felt himself about to explode. Before he erupted, he released her hand and aimed his cock at her face, and they all watched as ropes of cum splashed over her face and breasts. Jerry saw what he did and decided that he would do something different. He straddled Mrs. S chest and placed his cock between her breasts. He then squeezed them together and began humping her hard and fast. “Fuck, I didn’t think this would feel great but holy shit, I’m not gonna last at alllllll…” Jerry said and as he was finishing his sentence he was shooting cum across her face and under her chin. The boys saw dribbles of cum slowly sliding down her body in trails. Rod and Rick each decided to stand at her midsection and took turns playing with her breasts or pushing their fingers around her pussy as they jerked off. They both were able to climax at the same time and aimed their loads over her bare mound and watched in amazement as their cum slowly slid down her lips.

The only one not to cum was Mike and he told the boys with limp dicks to turn her over. They did what he said and the cum that had slid back now began sliding back towards her front again and Mike kneeled between her legs. “You said no fucking!” Jerry said angrily.

“I’m not gonna fuck her but I am going to coat her back.” He said and placed the head of his thick cock between her large ass cheeks. Mike then pushed her cheeks together and began sliding back and forth like Jerry had done with her breasts. He also didn’t last long and shot his load over her back. He then stood up and stepped back.

“I’m out of storage on my phone dude!” Darrel said to everyone.

“Me too!” Jerry said.

“Me too!” Rod and Rick said together.

“I don’t have any room either.” Said Darrel.

“I have just a little more room. Sit her up against the headboard and open her legs then get next to her. It’s time for a chess team picture.” Mike told them then set the phone on the table and set a timer. He climbed into the picture and each of them grabbed her breasts, pussy or kissed her lips. After the camera flash went off, they stood up from the bed.

“What do we do now?” Darrel asked. Even as he was asking, he saw that Jerry was hard again and using Darrel’s trick of having Mrs. S jerk him off before he shot a lot almost directly at her lips. The other guys saw this and also returned for seconds then thirds until they were all flaccid and unable to get an erection again. By this time, it was 3AM and they had a call time of 6AM.

“We need to clean her up. Jerry get a washcloth. Darrel make sure her clothes are un marred. Rod and Rick find her nightgown in her bag.” Mike said and each person did their respective jobs. Jerry returned with two washcloths and Mike and he went about the business of wiping the cum from her shimmering body. Once they felt they got as much as they could they called Rod and Rick over with her night clothes.

“All we found was a gray shirt and some white panties.” They said and Mike watched as Rick held her white panties to his nose and inhaling deeply before handing them over.

“Jerry and I are going to stand her up and I want you guys to take off the bedspread and toss it in the closet there.” Then he pointed to the only closet in the room. Jerry and Mike leveraged her to the edge of the bed then stood her up and the three others gathered the cum covered bedspread and shoved it in the closet. While she was standing Rod and Rick were able to put her gray tee-shirt on and then as they laid her back down jerry placed her feet in the panties then lifted her heels on his shoulders and slid them up her legs then jerked them under her butt until they were in place. The boys then covered her in the sheets and walked out of the room with their clothes in their arms.

They high-fived as they went back to their room naked with their clothes in front of them. As they got to their rooms, they all quickly fell asleep and it seemed that right away there was a knock on the door. “Time to get up sleepy-heads. We have a competition!” The cheery voice of Mrs. S came bolting into their rooms.

The boys looked at each other and they all felt the same. They were completely drained of energy and they slowly moved to dress and gather their things for check out. Once they gathered, they went to the lobby to find Mrs. S at the check-out desk talking to the manager. Then she turned and walked to the boys. “Apparently they aren’t charging us because someone slipped something in my drink? But they showed me the tape and it looks like Mike came to my rescue. Thank you, Mike.” She said as she hugged him. Mike noticed that she was again wearing the green dress and wondered if she had the sexy bra on. He knew she didn’t have the panties because Jerry kept those. He showed them off like a trophy.

They made it to the van and to the competition which they lost and then they began their travels back to the school. On the way back Barbara Steward looked in the rearview mirror then over at Mike in the Passenger seat. “The only thing I can’t figure out is how did I end up losing a pair of my panties but that I gained a pair of boxers? You know what. Let’s forget this ever happened. Please!” She said then returned to driving. The boys all looked at each other and nodded. They would keep their treasure trove of pictures and videos in the chess club and the chess club alone. As they pulled into the school, they all went their separate ways and Barbara drove home happy that it was now over.
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