Mrs Steward Chaperones Chess Team

If you think Loving Wives doesn't include Cucking or cheating wives then bypass this story. This story is about Barbara's friend Ann that ended the school year stressed and in need of the D. She relies on Barbara to help her get laid and they go to the bar and things devolve from there. All characters are over 18

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"Oh My God!" I need a fucking drink babe!" A woman said to Barbara down the hall of the school she worked at. As she turned to find the source of the voice, she saw the smiling face of her best friend Ann. It was the last day of the school year and the two women were some of the final people still in the school. Barbara knew she needed to wrap up a few last-minute tasks before the break and Ann enjoyed the solitude that an empty school offered before she went back home to the chaos of a small child.

"Was the year really that bad?" She asked her as they now walked towards each other. When they met, they embraced in an intimate embrace. Not one that was common of lovers but as long-term friends which is what they were. Ann and Barbara understood each other as sisters, and both held love for each other. As the two women hugged there heard the sound of soft footsteps approaching from the opposite direction from where Ann came from. The women broke apart from their hug and looked down towards the sound. They saw Jerry and Mike from the Chess Club.

"Ahh, did we miss the hug invitation Mrs., B and Ms. Ann?' Mike asked as he was passing them. Jerry elbowed Mike in the ribs because of what they had done to Barbara when she chaperoned their trip earlier in the year. Mike looked at Jerry for a moment and saw the pleading in his eyes. "Well would you mind if I got a picture of the two prettiest teachers in school since we are off to the real world come next year?" He asked and held up his phone to them. The phone he held up still had evidence of the night they covered Barbara in loads of cum and each night he still looked at it while he stroked his cock.

"What are you both still doing here?" Barbara asked them.

"Well Mrs. B, Can I tell you a secret?" He asked before continuing and not waiting for a reply. "Every outgoing class on the Chess Team sets up a small harmless prank for the incoming class as a sort of going away present for us and a welcome to the club for the new kids next year." He told both teachers in the empty hallway. "So, How about that picture ladies?" He asked.

Barbara looked unsure of his request because she always worried about the optics of what people saw when they were in the school. She had already made the mistake of visiting a former students home and was thankful that nobody there had spread any information about what happened there and she knew something happened on her chaperone trip but since she slept through it she couldn't be sure but the way that Mike looked at her now and the other boys would look at her as she passed them in the hallway she had her suspicions.

While Barbara was busy trying to think of a way to tell him no, Ann was wrapping her arms around her. At her touch she realized that the decision was made and wrapped her arms back around Ann. The entire time that she knew Ann she was at a loss for anything that she decided. Once Ann made a decision; right or wrong; she dedicated herself to it 100%. Mike Pulled his phone up in front of him and snapped multiple shots of the two older women in their friendly embrace. "How about a small kiss now?" Mike asked as innocently as he could. Ann laughed genuinely and her mouth opened which caused her voice to echo down the hall.

Ann began to approach Barbara's face before she held up a hand and pressed the palm of her hand into her friend's face. Mike for his part continue taking silent pictures of what was happening. "I'm not kissing you Ann. It wouldn't be appropriate here." She told her.

"Like we've never kissed hello or goodbye to each other." She said as her face was still pressed against her friends' hand. As she pulled back Barbara lowered her hand. They were still in a soft embrace facing each other. The three of them stood watching as Barbara thought about the possible implications of this happening then finally came to a decision.

"Mike!" Barbara said. "This is not to end up anywhere. Do you understand?" She continued and looked at him with intensity. Her eyes seemed to burn him, and her hair seemed to become a more vibrant red. After he nodded at her she looked to Jerry and he also nodded at her with wide eyes before looking at Ann and quickly leaning forward and pecking her friend on the lips. The sheer number of pictures that Mike took was astonishing. He knew when he went through his pictures later that he could make this kiss look nothing like a friendly kiss and more like a sensual kiss between lovers.

Mike then tried to push his luck a little further. "Can I get one more picture between you two?" He asked as he handed off his phone to Jerry who stood mutely to the side and was so still, he was almost an invisible person in the deserted hallway that held just the four of them. Barbara couldn't think of a reason that a picture with them could be bad. She had taken many pictures with her students over the years and her favorites always seemed to ask for this at the end of the year like Mike did now. Ann and Barbara spread apart enough to create a space between them for Mike to squeeze between.

Mike felt like a kid in a candy store being sandwiched between them. On his right was his most common jerk off fantasy Ms. Ann and to the right was Mrs. B. He knew that Ms. Ann wasn't married but that she had a kid and he was still young. Her body was tight in all the right places. While her breasts were on the small side, her ass made up for it. In fact, Mike had spent many times in the halls trying to catch Ms. Ann and Mrs. B walking away together and he liked that visual the best.

Today Ms. Ann was in a gingham patterned dress with the pattern turned at a 45-degree angle. It was blue with black hatching on it. The neckline was modest and seemed to hug around her neck then flare slightly at the sides. He knew from looking at it that there would be no down blouse shots for him. She was always conservative with how she dressed at school and it made him wonder how she would dress outside these school walls. Her dress had sleeves that squeezed her arms tightly and ended at the crook of her elbow. It wasn't a tight garment, but it fit her perfectly. It seemed to hug the contours of her body as it made its way to the end of the material which was about four inches above her knee.

On Mrs. B he thought that a dress that stopped this high would afford him quite the view but alas Ms. Ann's legs were a bit longer than Mrs. B's. While Mike always loved the idea of a woman in a dress without anything on beneath it, he thought that the dark black stockings that she wore with her dress only accentuated the look. He desperately wanted a reason to run his hands over the soft material and then up between her legs. Ms. Ann was a natural beauty and from Mikes recollection she always wore light makeup and a lipstick that was a muted red or pink color and light eyeshadow. Her pixie cut brown hair seemed to fit her more than any other haircut would.

The only thing that Mike didn't like about how Ann looked was that when he jerked off imagining her sucking him off he always wanted to be able to grip hair in both hands on either side of her head and with her short hair he didn't think he could pull that off. That didn't mean he would let the opportunity pass where he would think of him choking her with his cock deep in her throat.

Mrs. B still looked as radiant as she did on their chaperone trip. Her straight red hair draped her face and ended just below her shoulders. Her hair seemed to shine and hold a soft volume that just dared you to run your hands through and Mike nearly fell into that trap as he moved comfortably between the two women. She wore a black and white blouse that looked like the snowy screen you see on a TV channel that you didn't get permission to watch. Paired with that was an Army green colored skirt that ended below her knees.

Her calves poked out below the skirt and Mike did the right thing and undressed her with his mind. He thought about her bare pussy and remembered how wet she'd get. He saw through her shirt and straight at her larger breasts with their pale nipple on top.

As Mike could feel himself harden, he wrapped an arm around the waist of each woman. While Mrs. Ann looked like she was having a wonderful time, Mrs. B still looked worried and kept casting glances down the hallways. The others couldn't tell if she was looking for a reason to stop what they were doing or hoping they didn't get caught. Either way, all three of them knew they were working on borrowed time.

Mike felt the curve of both women's bodies as he curled his fingertips gently around their waists. Jerry lifted the camera and began taking pictures of the three of them. Slowly; as Jerry was taking pictures Mike lowered both of his hands closer to the ladies asses. He then winked at Jerry as a sign and moved both hands until they spanned and then gripped the butts of both women at the same time. Jerry caught the moment they both felt and processed this new violation.

The picture that he captured and would look at later when they were alone caught completely opposed expressions. Barbara's face flew open in an exaggerated 'O', her face instantly flushed a bright pink and there was an instantaneous anger in her eyes. Ann had an opposite expression. Her expression was that of pure bliss. She had a mischievous smile and seemed to press back into Mikes hand as it squeezed her cheeks.

"What the fuck Mike?" Barbara screamed at him. "You can't do that! I'm your fucking teacher and I'm married." She berated him as she pushed away from his hand and stared at him with disbelief.

"Sorry Mrs. B but like I said, we are never coming back so I figured I didn't have anything to lose at this point and I spent years wanting to do that." Mike told her.

"Calm down Barbara, they're technically not even our students anymore and they are legal after all." She said laughing and not moving from where she was. Mike didn't say anything else but also didn't move closer to them again either. Ann looked at Mike and asked, "How about just one more picture Mike?"

Mike was a bit surprised by her question after his groping and silently nodded his head as he was quite dumbfounded. He was absolutely sure that he would be slapped by both men but neither of them did anything and instead Mrs. Ann was offering another shot. Ann turned so that the front of her body faced the side of Mike and pressed her body and breasts into his shoulder.

He felt the tenderness as she added more pressure then leaned into him and whispered in his ear, "You're going to jerk off to these later and you'll wonder if you could have gone further when you get home had you taken a chance. The answer to that is yes, yes you could have."

She then moved his hand where it had retreated back to her hip and lowered it, so it was clearly on her ass again and then with her other hand she hitched her skirt up a little bit and then lifted her leg and crossed it around Mikes body. She then reached over and grabbed his other hand and placed it on her upper thigh then looked at the camera as Jerry looked on uncertainly. "Jerry, you can take the picture now dear." She said and Jerry took the picture.

"Alright Ann, that's enough. Boys you need to leave now thank you. Mike, those better not show up anywhere. Do you hear me?" Barbara asked in a serious tone.

"You got it Mrs. B." Mike answered as he quickly lowered Ann's leg to the ground, pushed his growing erection back down and moved out from next to Ann before racing away with Jerry.

"What the fuck was that Ann, we can't let them get away with that! What if they tell someone or show someone those pictures?" Barbara asked her.

"Oh, come on, don't act like you didn't enjoy the attention. I bet you got so hot from that. You were always a secret slut. I bet Jan doesn't know about that time when you were younger when you let your professor fuck you in college. What grade did you earn in that class again?" Ann asked laughing.

She didn't wait for a response because she didn't need one. Instead she reached over and grabbed her friends' hand then walked to their cars holding hands. "Come on, let's go to your house and get ready. We're going drinking to celebrate tonight and your husband can't come. He'll scare away all the guys I want to fuck." She told her.

They drove separately to Barbara's house and they walked in together. Jan came out and greeted them in the living room as they walked in. "How are my two favorite ladies?" He asked them.

"Stop flirting with me when your wife is right here!" Ann jokingly said as they walked in. Ann knew about the crush that Jan had on her because whenever Barbara got drunk, she would mention it. Ever since then she makes it a point to torture him with what she wears or little glimpses she gives him without ever letting him see anything. To her it's a game and for her part, Barbara knows but isn't worried because she knows that her friend wouldn't try and ruin her relationship and Jan isn't her type.

Where Jan is gentle and sensitive, she thrived with men that were aggressive and treated her like a thing rather than a queen. "Stop distracting us Jan, we have things to do and booze to drink and mommas gotta get the D tonight." She says jokingly. Even though he has a crush on Ann he doesn't like how much wilder she is than his own wife. Jan is certain that she is a bad influence on Barbara.

"Maybe I should come tonight just as a designated driver. I promise not to get in the way." He said to Barbara because he felt that she would agree where Ann would decline.

"No way!" Ann said as she looped her arm through Barbara's and pulled her down the hall to their master bedroom then closed the door. Jan was left outside the door and when he tried the knob it was locked. When he knocked on the door and asked to be let in, he was answered almost right away by Ann. "We have to get ready in private. Go make us a drink!" She said,

Jan wanted to please them and so he turned around and made his way back to the kitchen. While they didn't drink often in their house, he always made sure they had something to enjoy when they wanted to wind down. He opened the refrigerator and pulled out a blue bottle with a wide base tapered to a small neck named Risata Moscato d'Asti. It was a dessert wine and was often on the verge of being overly sweet, but it was an enjoyable drink. He filled two glasses entirely full as he didn't want to be sent back for getting too little.

He stood at their bedrooms door and knocked on the door with his left hand while holding both glasses of Moscato in his right hand. They were so filled that as he stood trying to seem like he was in control the slight shake in his hand caused the wine inside to dribble of over the tops of the glasses. When Ann opened the door, she saw him standing there with the wine and also noticed the dribbling of the wine down the glass, through his fingers and dripping down onto the floor. She took the glasses from him and walked back into the room.

Behind her she kicked the door closed again. Jan could hear her laughing then heard mumbled talk between them until he could distinctively hear Barbara's voice. She then swung open the door to show Jan still standing at the door dumbfounded. "You need to clean this up now or it's going to stain." She told him as she pointed at the small drops of wine on the floor. She scolded him like he was a dog that had just peed in the house instead of outside. Jan felt the defeat and retreated to get paper towels and the cleaner to clean up his mess.

When he returned the door was once again closed but the girls were talking louder. Ann could be distinctively be heard when she was speaking, "You're not gonna get me laid dressed like that. Don't you care about me?" Ann asked. To his ear Jan could only make out a mumbled response from Barbara. He tried to get closer to the door until he was pressed up against it. Long ago he gave up on cleaning up the mess he had made, and he knew that no one would be able to tell the difference anyway.

He wasn't sure how long he leaned against the door, but the door suddenly opened and at first, he saw Barbara's patent leather red high heels. The last time she wore those she looked stunning in a matching red blouse with a large scoop front that gave plenty of views of her ample chest and a black frilly skirt. As he raised his head this time what he saw was a tight black skirt that ended mid-thigh over bare legs.

His eyes continued to travel north where he found that she was wearing the top that he had seen her pass out in more than once. It was a light material with a black background and a floral design aver it all. Like the red shirt he had recalled earlier this shirt also had an open neck that ended where her breasts were pushed together by her bra. The view even from below her would have stopped a heart of a weaker man. The sleeveless arms scooped precariously low under her arms and he could see her black bra peeking out from under the shirt.

After finally being able to digest her entire outfit he tried to conspicuously check out Ann as well. She was wearing a dress that left nothing she had to the imagination. While it didn't expose anything, it was so tight that the shape of her breasts stood out before anything else. She smiled down at him as he rose, and he let his eyes catch on her legs which were still clad in her black pantyhose.

The length of the skirt landed mid-thigh like Barbara's and as he looked at her waist, he couldn't see the line of her panties through the material. He desperately wanted to reach out and feel it, but his better judgement prevailed, and he stood to the side as the women walked by him.

"Don't wait up Jan, she won't be back until mama gets some." Ann told him playfully as they walked out of the door. Once outside Ann leaned down and folded the bottom of her dress up another two inches causing the already short skirt to nearly become a micro-skirt. She then tried to do the same thing to Barbara's dress which elicited a slap from her. "Now we just wait for our Uber." Ann said as they stood on the corner.

They soon saw a car pulling up next to them. They quickly opened the door and climbed in. The driver turned in his seat and happily watched the show as both women climbed in and got themselves comfortable. "I was apprehensive to stop to be honest. At first blush I took you both to be whores. I thought better of it given the neighborhood, but I wanted to make you aware of how it looks in case you were looking for a different kind of attention." He told them then turned in his seat and drove to the destination they provided.

"What am I doing her dressed like this?" Barbara asked Ann as they stepped out of the cab in front of the bar. It was a dingy place and the street looked wet even though the weather was clear all day. It was littered with cups and cigarette butts and smelled like vomit. It was still early in the night and already Barbara knew that this was a bad idea.

"You're dressed like that because I haven't had sex in three months and after a year like that in school I need to unwind with a nice glass of wine and a fat cock. You wouldn't want me to come out here all by myself, would you? What if I was raped?" She asked then gave her a pouty face with her lower lip pushed out past her upper lip and she tried to make her eyes look sad enough for her friend to give up and continue into the bar with her.

When she didn't sense her pulling away from the bar Ann pulled toward the door. As they reached the single hung door that was a sheet of metal with a bar as a handle. As Ann was reaching for it, the door swung out towards them and caught them off guard. Three men tumbled out past them into the street and as they gathered themselves from the startle they began to walk through the now open door. When Barbara looked back to ensure the three men were alright, she noticed that two of them were looking back at her and seemed to look her up and down. She suddenly felt naked and alone and hurried to catch back up to her friend who didn't make it very far in front of her.