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This story was inspired by a conversation with someone about two years ago. If she reads it, she’ll know.
“C’mon, Will. It’ll be a great weekend and you’ll love my mom. She’s super nice and a great cook.”
Will’s girlfriend Sheri had arranged a long weekend away at her Mom’s house. Will was happy to get away from college for the weekend but would have liked some alone time with Sheri instead. No matter what though he was happy to be getting away and spending some time with her even if her Mom was in the picture. That and Sheri’s best friend Maureen was tagging along as a third wheel. He and Maureen got along great, though. Sheri always talked about he was more understanding that a lot of boyfriends would be about doing things she wanted if what she wanted was just hanging out with Maureen and drinking and telling stories.
Sheri always made her mom sound so maternal — she told Will what a good cook her mom was and how nice she was. He was half expecting some grandmotherly woman making apple pies all weekend.
Sheri only lived an hour away but Will had never up before. He knew Sheri’s mom had gotten divorced almost a year ago and Sheri was an only child so her mom lived alone. That was okay because it meant there was room for all of them in the house.
He crashed in the backseat on the way up because Sheri wanted to drive and she and Maureen talked the whole way. Part of the reason Will was a good boyfriend is that he was okay with being semi-invisible when they talked or he went shopping with them or the three of them hung out together.
Sheri’s mom lived in a small house at the end of a street, a little isolated but in a neighborhood. They went in with three small bags of luggage which Will carried – he joked about just being there as the bag handler.
They got inside and Sheri’s mom hugged both Sheri and Maureen, who she had met before. Then Sheri introduced Will. He was surprised. Sheri’s mom wasn’t an older lady in an apron making pies not that he really expected that. Instead he was surprised to see a stunning woman with kinky red hair and deep, warm green eyes. She looked so much younger than he expected and the combination of red hair, pretty white skin, and those eyes was amazing. He found it hard to believe she was Sheri’s mom and had to work hard not to stare at her. She seemed so young that he thought she could easily have been Sheri’s sister even though they had different looks.
He almost forgot to say hi and for a second Will was afraid he was too obvious. But Sheri’s mom gave him a quick hug and insisted he should call her Teri not anything else. “After all, we’re all adults, aren’t we Will?”
Will came back to reality enough to listen to Sheri telling her mom “I hope you haven’t made any plans at all because we’re going to do nothing except enjoy ourselves and have a girls weekend. Nothing to do but fun.”
Her mom laughed and said, “well, how does Will fit into a girls weekend? He certainly looks like a man to me.” The way her eyes rested on him after she said it made Will blush but no one else noticed.
Maureen just laughed and said, “our darling Willie is always one of the girls. He fits right in, isn’t that right, Sheri?”
Will hated it when Maureen teased him like that but Sheri stood up for him. “Don’t be a bitch, Maureen. She’s kidding. What she means is Will is easy to hang out with and we can relax around him so it’s the same thing.”
Teri immediately acted to make Will comfortable. She walked over, smiling, and gave him a big hug. Maybe it was a motherly hug but being squeezed tight and smelling her perfume and feeling her close made him excited. “Will, I’m sure we will all have fun with you and I’m so glad you came.”
Will felt welcome. “Thanks, Mrs. uh, I mean, thanks Teri. I’m glad to be here. let me know if there’s anything I can do to help.”
Each of them had a room so they went and stashed their stuff before they had to hurry off to dinner, all four of them. Will and Sheri rode in the back while Maureen talked to Sheri’s mom.
It wasn’t a long trip to the restaurant but long enough for Sheri to tease her boyfriend and nibble on his ear. Before they got out at the restaurant, she patted him on his by now very hard bulge and giggled.
They went to the Murphy’s Pub and Grill that was attached to the mall. It was a chain but they had good nachos and Friday night drinks.
Sheri announced that Will had volunteered to drive so he’d just have one beer so they could all drink. “It works out well for all of us since it’s ladies night,” she added.
Teri and the girls had a few drinks. On about their third, Teri realized how happy she was and how well they were all getting along. She and Sheri and Maureen felt like three girlfriends not anything else. She was listening to Maureen tell some story and found herself looking at Will across from her. He wasn’t built like a football player but he was in good shape and boyishly cute. She figured illegal bahis out that he was a little shy but very polite and helpful. The kind of man who would natural volunteer to be designated driver. The kind of man who didn’t seem to mind at all being third wheel to his girlfriend and her best friend.
She also realized as she stared at him out of the corner of her eye, trying not to be caught, that he kept looking at her. It didn’t take her long to realize why. She was leaning forward. Still dressed from work, her white business-like blouse would sag a little as she leaned and she was pretty sure he could see the lace top of her bra from his angle.
She was secretly flattered. She was surprised at how it made her feel. Instead of leaning back she just stayed there, very subtly displaying herself. Instead of thinking he was just some pervert or being offended that her daughter’s boyfriend was trying to look down her blouse, she was excited. Her first thought was that she was glad she wore a pretty bra. It was ivory colored with lace and pretty. Another part of her was happy that he noticed. She didn’t much since her husband had left her and she was pleased to be looked at .
Twice she shifted in her seat and moved a little to improve the angle. It made her happy and he was so cute trying to be subtle and not be caught by either her or his girlfriend. She’d had three drinks which was a lot for her but she felt better than she had in years.
She was always glad to see her daughter home from school but this was going to be a nice weekend she felt sure. She felt younger with her daughter and Maureen and now Sheri’s new boyfriend made Teri feel even better.
Before long they were leaving the restaurant and Teri was feeling no pain. She wasn’t drunk but maybe a little tipsy. Instead of immediately heading back to their car, they walked into the mall the restaurant was attached to.
The three women were giggling like old friends. It made Will happy to see his girlfriend like that and he knew that it made her happy to see her mom in a good mood. When they originally decided to come up, Sheri made it clear to Will that she was worried her mom didn’t do enough and was depressed a little in the year since her divorce. So Will knew that this was a success so far.
Maureen linked her arms with her two friends as they walked around the mall. She would not have brought Will but she didn’t really mind him. She intended to have a fun and crazy weekend with her best friend and her mom. She wasn’t seeing anyone right then and decided she would have fun with someone. If that included some time in a bed that was fine too. Just not with Will. She wasn’t completely off men but definitely preferred women. No matter what, the weekend called for a lot of alcohol.
Maureen did appreciate how helpful and obedient Will was. He was like Sheri’s puppy dog, she thought. Followed them everywhere and was happy to follow them into one store after another and carry their bags. No one really bought much but Maureen found a pair of shoes and Sheri got a sweater. And of course Maureen enjoyed embarrassing him in the first lingerie shop they stopped at. Maureen enjoyed teasing and tormenting Will but really she liked him. he was nice to her best friend, not jealous of any time anyone else spent with Sheri and they actually got along well. That didn’t stop her from asking the sales lady right in front of Will if he thought panties were more comfortable or a thong fit him better.
After some more teasing and some more stores, they decided to split up. Sheri sent Will back to get the car and meet them at the other entrance while Maureen had one more shop to go to. Will was always happy to do things like that. So he went and got the car since he had to drive and eventually got back around to the other door. It wasn’t long before the women came out, loaded the bags in the back and piled in.
Maureen insisted on a quick detour to the liquor store and she ran in with Sheri while Will waited in the car with Teri. Teri was having fun. She had already decided she liked Will. She was pleased by her daughter’s good taste. Also she was having a great time. The girls made her feel young and she was doing her best to keep up with them and have a great weekend.
Will was looking at her again which she liked. It really made her night that he might try to peek at her. He asked her, “I hope we aren’t ruining a quiet weekend for you. I wasn’t sure if we should all come.”
She turned in the front seat and looked at him. She brushed the red hair back from her face and her warm green eyes held him in her gaze, almost frozen. She grabbed a hand and held it in hers and said, “Will, please. I am so very happy that Sheri came and that she brought you. I am very happy to meet you and find how very sweet you are. And very handsome.” With that she winked and Will couldn’t help blushing. “I haven’t had this much fun at any time since my divorce and the night is just starting. I’m looking illegal bahis siteleri forward to a wonderful weekend with wonderful people.”
At that point, the other women got back from their liquor run and piled in and Will drove back. They hadn’t decided what to do but Teri started making nachos while the other girls got all the drinks together. They made a big pitcher of margaritas and had already started drinking. Sheri made sure that Will had a glass because they weren’t going out anymore and Maureen made sure Teri had some while she got the nachos in the oven.
They took the nachos and drinks to a big coffee table in the living room and just sat around. Will didn’t say much but that was usual. Sheri and Teri were both telling stories about when Sheri was younger. Maureen asked a lot of questions but made sure everyone’s glasses stayed filled. Maureen wasn’t sure what she wanted yet out of the weekend but having everyone start the weekend happily drunk seemed like a really good idea.
Will didn’t say a lot but he would ask a question now and then to keep things moving. While they were talking about some story about the mall years ago, Will asked “so what did you guys buy?”
Maureen laughed and said, “Willie dear, one of the features of any girls weekend is matching outfits like a T shirt or something. But we only got something for the girls. I thought you should be included but your dear girlfriend didn’t want to. Oh don’t look disappointed, I’m teasing you. We all got the same underwear. It was my idea. I wasn’t sure they had panties in the right size for you.” She couldn’t help herself, she enjoyed teasing Will because he was such a good sport and it made Sheri annoyed.
Sheri intervened. “Maureen stop teasing him. He’s being so good and helpful and stuff, be nice. I’m sure we don’t need to talk about this now. We need to be nice”
Maureen wasn’t the kind of person to let things drop though. She had a wicked grin on her face. “You know, Sheri, you really are the only one who can do anything about this. If you want to be so nice to Will then just show him. Teri and I don’t care and I’m sure your lover boy has seen you in your undies before. Go ahead, after all none of us have them on yet so it will give me and your… me and Teri a chance to see if we like the look. Go ahead, we need a model and Willie won’t complain. Come on. Do it. Right now.”
Maureen was drunk and poking. Teri was just giggling. And Sheri, as drunk as anyone else, just told Maureen to shut up and winked at Will. She went away and came back five minutes later. She was wearing a short white satin robe and had a big smile on. She walked past Maureen and stuck out her tongue. With her back to her mom and Maureen, she leaned in and opened her robe for Will and leaned over a bit. “Just for you honey.” Then she tied her robe and went back to the couch.
Will had a big smile on his face and so did Sheri. She just sat down, crossed her beautiful legs and picked up her drink. Maureen pretended to be mad. “That’s no fair. Teri and I didn’t get to see. You didn’t model for us. How are we supposed to know if we like them too? Teri, tell her she has to be good and model for us too.”
All three women were laughing. Sheri got a wicked look in her eyes and stood up. She faced Maureen and said, “it’s up to you, Maureen. You can take the robe off me if you wish but then you have to go put yours on too. If you show me off, we all get to see more of you too. So make your choice.”
Maureen, drank the rest of her glass, stood up and took the robe off Sheri with a wicked grin. “I’ll be right back. Don’t go putting anything else on, sweet thing.”
Maureen came back in just a few minutes with the robe barely covering her. She stood in front of Sheri and made her stand up and remove the robe, letting it fall to the floor. Then Sheri slowly turned her and she slowly turned Sheri. The two of them were comfortably drunk and having fun. Teri was uncomfortable but looking at them both with nervous interest.
Maureen rubbed herself against Sheri as a playful joke and then lightly smacked her on her panty covered butt and grinned at Will. “You got a hot girlfriend Willie baby. I think I’m going to have to borrow her.” With that she grabbed Sheri’s breasts and broke up laughing.
She was being playful but she was also very lusty. She remembered how much she always liked Sheri. This second all she wanted to do was kiss her and didn’t care about boyfriends or moms but didn’t think it was possible.
Sheri was laughing too and licking her lips at Will. She was comfortable and having fun surrounded by people she cared about and always felt like herself around. She realized that part of her liked it when Maureen spanked her lightly and she liked being paraded around for her boyfriend like she was being shown off. Alcohol and happy feelings made her a tiny bit wet.
Will wanted to do nothing to stop anything so he just smiled and went along and tried not to be canlı bahis siteleri obvious or a big deal. Two good looking women hanging around with him wearing matching underwear sets was like a weird dream. He also liked checking out Sheri’s mom who was probably having fun but seemed a little more nervous. But it was hard to notice anything except the two women in matching lingerie. He was hard and having a great night.
Maureen smiled because she had a plan or at least part of one. She waited and sat down on Sheri’s lap, continuing the mood. “Hey, Will, I thought you were a gentleman?”
Will was surprised and confused. “What? Yes I am, what’s wrong?”
Maureen smiled as she wiggled in Sheri’s lap. “Will, your girlfriend and her very best friend in all the entire world — that’s me — are forced to sit here in their underwear. Delicious, new underwear that makes both of them look hot as hell of course but underwear. And you sit there wearing lots and lots of clothes. They wouldn’t let me buy you panties but I think it is only fair that you strip down to your undies too. Don’t you agree, Sheri, that a gentleman would make an effort to make you feel comfortable?”
Sheri was giggling and nodding her head. “Oh yes, Will. She’s right.”
So, Will, always willing to do anything he was told, stood up. He noticed that Teri hadn’t said anything at all but sat up a little and was staring. He didn’t look directly at her but it turned him on a little to know that he was exposing himself a little bit anyway to someone who was a stranger until a few hours ago and that she was watching.
He took off his shirt and stripped until he was wearing just a pair of white briefs. He wasn’t real muscular but was in good shape. He also realized that the shape of his erection was obvious if anyone stared and getting harder.
If it wasn’t obvious it became obvious when Maureen said in a loud pretend whisper, “Sheri I think he likes your undies. I can see his cock hard under his shorts but don’t stare.” Then she just laughed.
“Thank you, Will, for making us all more comfortable. You really must be a gentleman. I would give you a kiss for being so helpful and cooperative but I don’t think your girlfriend would appreciate her super hot awesome looking best friend in the whole world frenching her guy. So you’re out of luck!” She laughed again. Maureen got silly when she was drunk even when she was working on a plan.
“Wait,” she suddenly shouted. “Sheri can kiss you later so instead of giving you one directly, I can give her one to give you.” And she leaned over and kissed Sheri on the cheek and they both laughed.
Then Maureen said, “I bet he’d want a better kiss.” So she put a hand behind Sheri’s head and pulled it in and kissed her for more than a couple seconds, softly and passionately. Will and Teri just stared, frozen.
They stopped and smiled. Maureen really liked it. She was feeling a little crazy and just wanted to stir everything up. She and Sheri had never gone out but it wasn’t the only time they ever had kissed or that their friendship was close to crossing the line. Plus, in the mood she was in there was almost nothing she wouldn’t think about. Sheri liked it too and was just having fun.
Sheri didn’t comment on the kiss or anything else. She just said, “my glass is empty.”
Maureen jumped up, grabbed a few glasses and ran back to the kitchen and started making drinks. In a minute she called, “hey Will get in here and be a waiter!”
Will took some dishes out and grabbed two drinks from Maureen. The first one he took to his girlfriend who took her glass from him and then kissed him just once while cupping his erection and squeezing. “I like the waiters at this bar.”
He took the other one and turned and gave it to Teri. Teri said thank you quietly but didn’t make eye contact. Her eyes were staring at the bulge in his shorts close to her eye level. They didn’t linger long but Will was a little embarrassed and a little excited.
Maureen strutted back in and circled around making sure everyone had a drink and making a big show of deciding where to sit. She wiggled her but enough in front of Sheri that she reached out and snapped the waistband of her panties from behind and said “you going to put that ass somewhere or just wiggle it?”
Maureen sat down on her best friend’s lap again for more fun. She noticed with satisfaction that Teri was making good progress on her latest drink.
“Teri, aren’t you happing we’re having a fun girls weekend together, all of us?”
Maureen continued, “I have to complain though. I bought us all matching outfits on my dad’s credit card and I have one and sexy Sheri has one and even our Willie is down to his shorts. But I don’t think you have even tried yours on. That doesn’t seem fair.”
Teri had trouble talking and was feeling unsure but also a little daring. She knew she needed a push but something inside her wanted a push.
Maureen sensed something so she stood up, grabbed the silk robe, told Will to wait and took Sheri and Teri and disappeared. Out of sight there were all business-like as if they were in a dressing room. Will couldn’t hear anything but he wondered.
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