Linda Jones was in the grocery store picking up a few things when she saw her friend Lisa Miller and her son Tommy. Lisa was supposed to come over later in the afternoon with a few friends for bridge club. “Hi Linda,” Lisa called out, waving at her in the produce aisle. “Tommy, you remember Mrs. Jones don’t you? Be a good boy and say hello.”
Linda Jones remembered the nice young man and was pleased to see he had grown up. The Millers were had been friends for years. “Hi, Tommy. How nice to see you again. I guess you graduated high school didn’t you. What are you up to now?”
It turned out that Tommy, although he was 19, was still living at home and hadn’t figured out what to do with himself. Lisa sent him to get a loaf of bread and then confided to Mrs. Jones, “it’s so nice having him around the house but I worry sometimes about him because he’s so shy and quiet. But I guess we all find ourselves at our own pace.”
As Tommy came back, Linda was saying, “You’re so lucky to have him around though. I always miss George when he’s away on a business trip and I have so much to do. I notice it when I’m getting ready for things like this afternoon without George around.”
Lisa’s face lit up and she insisted that Linda borrow Tommy for the afternoon. “Tommy would be happy to help, wouldn’t you dear? Mrs. Jones would be so grateful and I could just pick you up when I come over with the girls. No, no one say anything. That’s settled.”
Tommy was fine and didn’t say much. Helping some boring friend of his mom’s or helping him mom was all the same to him. Linda Jones laughed and said “I’m so grateful he’ll help an old lady out and I promise not to work him too hard. Just a few things I need help carrying and reaching and I’ll even find us lunch before everyone gets there later.”
They parted in the parking lot and Tommy helped load groceries and get into Mrs. Jones car. Linda Jones wasn’t exactly an old lady. She was in her late fifties but in good shape for her age, well dressed, very nice, and easy to talk to. Tommy didn’t think she was that old, just another boring woman like his mom and all her friends. But he was too shy to say much to her so she did most of the talking on the way home.
When they got to the house, they both carried groceries in and she put them away. She told Tommy to follow her upstairs and they’d get a few things done before lunch. Tommy was shy but when he followed her up he noticed that he enjoyed the view in front of him. Mrs. Jones was wearing a longer dress but it cupped her nicely as they climbed the stairs. He was embarrassed a little to be staring at her that way but it’s not like she could see.
They went into the spare room and Linda Jones surveyed Tommy. He was a good looking man and very polite, a little smaller than average but very sweet. “Tommy, are you ready to get to work?”
“Yes, Mrs. Jones, just tell me what to do,” Tommy said. Linda Jones liked it when a young man was nice and polite and maybe just a little intimidated by her. Tommy was perfect.
“All right, Tommy. Would you start by pulling my zipper down?” She turned and indicated the zipper on the back of her dress. Tommy looked startled and didn’t move. He didn’t know what to say. Mrs. Jones quickly added, “don’t be alarmed dear. We’re going to get a little dusty and I want to protect my dress. I’m sure you’ve helped your mommy with her zipper before. Now you must help me. Be a dear.”
She felt his hands fumble but eventually pull down the zipper past her waist. As she turned and shrugged out of it, she then bent and out it on a hanger. Tommy looked surprised. “See, honey, I’m wearing a slip. It doesn’t show anything and it’s perfectly fine. I think you were nervous, weren’t you?” She was very playful and he stammered, afraid he offended her.
“I’m sure your girlfriends wear skimpy little undies so this wouldn’t be appropriate but a proper woman wears a slip. Don’t any of your girlfriends wear slips or do they all dress like little sluts?”
Tommy wasn’t expecting this. He wasn’t used to slips but he wasn’t very experienced and Mrs. Jones made him very nervous. “No, I don’t have a girlfriend so I don’t know how they dress. I mean, it’s fine. I’m sure I don’t mean to be nervous. I hope I didn’t offend you.” He felt terrible but she was right that it didn’t show anything. It was like a dress just silky. It shouldn’t make him hard but he couldn’t help it so he tried not to think of it.
Mrs. Jones loved making a young man so nervous he stuttered. She was enjoying herself. She leaned forward and kissed him on the cheek, almost motherly. “That’s all right dear. I think the slip is pretty anyway even if it isn’t revealing. I think some men find the silk attractive and all the lace.” She took his hand. “see how it feels? it’s very soft, isn’t it? I like the way it feels but had to take my dress off to keep it clean.” She was moving his hand up and down her side and her hip with her own hand firmly directing him. She knew a young man like him would notice the bump as they crossed her panty line and not be able to stop thinking about it.
She could tell he was thinking and trying not to get hard but she also noticed he couldn’t help looking. It helped that her slip was thin and white and she wore very dark blue panties underneath it which were obvious. It was almost like she planned it to look seductive if a young man saw her dressed that way. But Tommy didn’t think that. He thought it was an accident. After all, there was no reason for him to think she might have known Tommy’s mom was going shopping and that Linda might have timed her visit to the store the same time and manipulated the discussion in such a way that Tommy would be sent home with her. No one would think that.
She let go of Tommy’s hand and asked him to get the ladder from behind the door and set it up by the attic access. “I need to stand down here and hold the latter Tommy because it isn’t steady. You go up and hand me down the extra folding chairs and I think I have a big red box with things in it.” Tommy gave her the chairs one after the other and she set them down but he couldn’t find a box. “There are no red boxes anywhere I can see, Ma’am.”
Mrs. Jones looked disappointed and told Tommy to come down. “Let me go look, I thought for sure that was up there. But please hold the latter tight so I’m not nervous.” She climbed up and kept asking him if he was holding it. Then she stood there shifting from one foot to the other looking into the crawl space. She was also looking down discreetly. She knew Tommy’s head was at her ankles and that the way she kept moving he could see a lot. She could tell he was looking up her slip so she smiled and kept shifting her feet and teasing him.
Finally she said “I don’t see a red box either. I don’t know. Maybe it’s in here. Oh yes, that’s the problem, it wasn’t a red box at all. How lucky I came up and found it. See Tommy, it’s blue.” She held the box out as she turned a little and then slipped and dropped the box clumsily in the wrong direction. “Leave it Tommy. Don’t leave the ladder. I don’t feel steady.” He gripped the ladder tight but didn’t dare look up so he wasn’t caught. As she descended, she accidentally made her slip catch for a moment on his head. She chuckled to herself but knew he was throbbing in his pants as she fixed it.
On the floor again, she said “Thanks Tommy. I’m sorry I forgot about the box being blue not red. Here hand me the dustcloth and you take the other one to wipe off the layers of dust on these chairs.” They dusted the chairs and Tommy didn’t even notice that the blue box didn’t seem to have any dust on it. Mrs. Jones noticed that every time she turned her back, Tommy was staring at her and trying not to get noticed. Things were working perfectly. She loved teasing shy younger men.
She told Tommy, “It looks like the box broke open when I dropped it. I’m sure it’s mostly junk in it but put it up on the bed and we’ll go through it.” As Tommy set it down it was more of a pile of clothes, odds and ends and cardboard than a box. Mrs. Jones tossed the lid aside and went through things. She moved aside three glasses, a small box of poker chips, some smaller boxes and a pile of clothing. Then she held up two boxes of playing cards. “Here are they are. I was afraid I was going to have to run out and buy new ones. Now let’s get rid of the rest of this junk.”
She tucked the glasses into an end table next to the bed along with the poker chips and small boxes. Then she told Tommy to sort the clothing while she ran the cards downstairs to the table where they were going to play bridge later. Tommy looked at the clothes and then looked nervous. She took his hand “Now, Tommy, don’t be silly. There are some underthings in there but itsn’t like they’re attached to anyone. I’m sure you’ve folded your mommy’s panties and things before. We’re just sorting clothes here. Honestly, you’re so nervous all the time.” Then she went away for a moment.
Two minutes later, she called out to him, “Be a dear and bring the whole pile of things in here, sweetie.” He grabbed the pile of silk and satin and carried them down the hall to the sound of her voice. It was coming from her bedroom it turned out. “Set them on the bed and we’ll put them away. Is everything sorted?” Tommy worked to make sure the piles hadn’t gotten mixed. He was a little nervous being in a lady’s bedroom but Mrs. Jones seemed relaxed. In fact the bed wasn’t even completely made up. One side was puled down where she must have slept without her husband. On that side was a long beautiful black nightgown, silky and beautiful. Next to it, just a few feet away were the panties she must have worn with it. They were red so he couldn’t miss them and just a few feet away from him. He tried not to stare but the red was like a magnet for his eyes.
He took his eyes away long enough to listen to Mrs. Jones. She was amused at how distracted he was able to turn just because a pair of panties she had forgotten to put away were lying around. Or maybe they were there because she had run down the hall to her room and carefully laid out the nightgown and panties but Tommy didn’t think that. He was just distracted. She paused and asked him again “why don’t we start with the bras? You hand them to me and I’ll put them away.” Tommy composed himself and took the two bras which he had lumped together and handed them to her. She put them in a drawer and said “panties too. I keep panties here in this drawer and those look like mine.”
Tommy handed her the five brightly colored panties, all satin and silk. Mrs. Jones took them and noticed his hands were already trembling. She held them with both his and her hands on them at the same time, pausing. “They are pretty, aren’t they? Don’t you think they’re pretty Tommy? A lot of men like looking at and touching women’s panties because they’re so pretty. I think mine really are, aren’t they?” Tommy just nodded his head. At that minute he was having a little trouble talking out loud. Mrs. Jones smiled and put them in her drawer.
“Now, what’s left? Oh my black slip. I’m so glad. I’ll put that here. Now what else?”
Tommy didn’t know what to say. He wasn’t sure what the rest was called. He held them up and looked unsure.
Mrs. Jones smiled at how well this was working out. “Don’t you know what that is, Tommy? Have you seen a garter belt and a pair of stockings before? Oh dear. I guess I will have to explain it to you. See the two things that feel like pantyhose but they are black and have only one leg? Yes, those are stockings and the other thing is used to hold them up. Now do you understand?”
As Tommy, looked too confused, Mrs. Jones continued. “Right now, I’m wearing pantyhose. I’m sure you know what those are, don’t you? Oh my goodness, I’m going to have to show you.”
Tommy looked almost scared now but she continued. Mrs. Jones lifted her slip until it was above her waist. Tommy’s eyes got real large as he saw her sheer pantyhose and a pair of blue panties, full covering but obviously silk and very sexy even though they weren’t skimpy. He just stared and got a little lost in what was happening. He didn’t think not to stare and he didn’t really think about if his erection could be noticed in his pants.
It could. Inside, Mrs. Jones was very pleased with the reaction she caused. She knew wearing the nice dark silky panties under sheer hose would have the right affect. Her set up of the situation couldn’t be going better. She was happy she had picked them and that she managed to be able to show off this early in Tommy’s visit. Everything was going better than she even hoped it would.
It also made her very pleased to see the rock hard bulge in Tommy’s pants. Her teasing was working and she loved it when young men reacted that way. So she kept going. She used one hand to rub the front of her panties and pantyhose to demonstrate. “See, Tommy, notice how these are like pants. They are thin and that’s why you can see my panties still, right here. Can you see that?” Tommy wasn’t responding very fast which pleased her more.
She kept rubbing the front in slow circles. “But stockings, Tommy, are like socks not pants. Like knee socks but even taller. If I had them on they would come all the way up almost to my panties but not quite. Haven’t you ever seen a woman wearing them, dear? Doesn’t your mommy ever wear them?”
Tommy finally regained his speech. “No, ma’am. This is the first I ever saw them. I mean I didn’t even know what they were at all. I’m sorry.”
Mrs. Jones pushed on. “Can you picture them, dear? I don’t know how else to describe them. I think maybe I will have to put these on for you so you have an idea what they are. That might be the best thing. Of course I don’t want to dress in front of you. That wouldn’t be appropriate. Wait here on the bed while I slip these on in the bathroom.” With that, she let the slip drop and took the items into the bathroom attached to her bedroom leaving Tommy on the bed with her nightgown and panties.
Tommy was very nervous. This wasn’t what he expected. Mrs. Jones was acting very matter of fact, it wasn’t like she was doing any of it on purpose he thought. But he couldn’t help being turned on. He stared down at the red panties next to him. They were her panties. Silk panties that had been on her body and right next to her most private areas. It was almost more than he could take. He moved his hand slightly and let his finger touch them. It was all he dared to do.
Just then, he heard a noise and turned. Mrs. Jones had come out of the bathroom. She didn’t show any sign of having noticed that Tommy had let his fingers touch the panties she had carelessly left on the bed. He figured she probably hadn’t noticed. She was looking down and talking while walking closer. “So you can see, Tommy, that I don’t look any different if you see me in my slip. They stockings on my legs look like pantyhose sticking out just black in this case. But look carefully, right here.” She rubbed her hand over bumps on her thighs and Tommy’s eyes stared.
“Tommy, that’s the spot where the garter is. The thing that hold the stocking up. If I didn’t have those they would fall down..” She was loving it. His eyes were drawn to where she pointed. It was almost like hypnotizing him. He was also clearly very turned on so she went further. “Now let me just lift my slip and show you. I’ll slide it past my waist and you can see the top of the stocking down here.” She traced the lace top with her finger stopping on the garter where it attached. “that’s what’s holding them up. Some ladies and their men like the way the gap looks, this area of skin between the top and the panties that is crossed by the garter. And the garter is attached up here to the satiny belt which matches the top of the stocking. Isn’t that nice?”
She stood there with her fingers holding his attention as they traced the garters and the skin and the edges of her panties even. His eyes were stuck on her as she stood just a foot away modeling for him. Mrs. Jones knew he was excited because she could see the lump in his pants. It made her very excited to but she hid it in her face. She tried to stay calm. That was one of the best parts of the tease for her. She knew what she was doing and how he was reacting but he had no idea.
“Tommy, some women like to wear these because they make they feel more dressed up and sometimes sexier. They are more work but sometimes our men appreciate the work and we like that. But you can be honest with me. Do you think they’re pretty? Or did you like the pantyhose more.”
Tommy’s voice wasn’t working well but he managed to get out that he liked them.
Mrs. Jones let her slip fall back down as her phone started ringing. She answered the phone still smiling at Tommy. “Oh, hi Lisa, how are you? Yes, Tommy and I are working very hard. He’s been very helpful and very polite. What’s that? Well if you’re passing by of course you should stop, we’re breaking for lunch anyway. When? Oh good, see you in five minutes.”
“Tommy, isn’t it nice that your mom is going to join us for lunch? I think she was worried you might not be helpful but I set her straight. Now, I better leave our garters on but it’ll be our little secret. Can you just help me find my dress again? It should okay while we eat.”
Tommy helped her into her dress, zipped her up, went downstairs with her, helped in the kitchen and stood by quietly while Mrs. Jones let his mom in and they talked. Soon all three were seated at a table eating sandwiches.
Mrs. Jones talked to Tommy’s mother while he just listened. They didn’t ignore him but they were talking about things that didn’t interest him or people he didn’t know. Tommy did look up suddenly when he felt a foot rubbing his leg. It was probably Mrs. Jones but he didn’t know she’d taken her shoes off and wasn’t sure why her foot was rubbing his ankle and snaking under his cuff. But he liked it and it made him very hard. She never looked at him though so he was nervous.
Very soon his mom left saying “I’ll let you too finish everything you’re doing and be back with the rest of the girls in a couple hours. Bye honey, you be a good boy for Mrs. Jones.” Tommy loved his mom but it annoyed him when she said weird things like be a good boy.
Mrs. Jones came back and grabbed a few plates. There weren’t many dishes to clear. As she finished with them, she turned and accidentally spilled a whole glass of water all over Tommy. It ended up soaking his pants.
She apologized over and over. “I’m so sorry, dear. We have to fix that before everyone gets here. Now quick, give me your pants. Don’t look so shocked. We have to get them in the dryer so they have time to dry before everyone gets here. Now, don’t be shy. It isn’t like I’ve never seen a man in his underpants before.”
Tommy was in a daze so he just did it. He took down his pants and handed them to her then followed her into the laundry room. He stood there while she touched the pants with a towel and then put them in the dryer. “Good, they’ll take a while in there but should be ready before anyone gets here. Now let’s go upstairs and see where we were.” She grabbed his hand and led him up the stairs.
He didn’t know what to do so he didn’t do anything. He just followed along, wearing just his underwear and socks (he took his shoes off to remove the pants) and his shirt which wasn’t long enough that it even covered things. “Now, before we start, let’s get my dress out of the way again. That worked well last time. The zipper, please.” With that she turned around. It wasn’t a request but more like a command not that he even thought about doing anything other than what she told him to.
He took the zipper and pulled it down like some kind of weird dream. As she stepped out, he remembered her garter belt and stockings because he could see the bumps. With her back to him he stared. It made him hard which he forgot he couldn’t hide well since he wasn’t wearing pants. Mrs. Jones noticed when she turned around and was pleased but didn’t say a word. Tommy was confused a little. He should have felt very weird being in his underwear but Mrs. Jones was so matter of fact that he sort of forgot that it was even unusual. He didn’t even think about his erection being noticeable.
Mrs. Jones loved how things were going. She felt very protective of this shy young man but she had a wonderful sense of power of her own attractiveness. She could go on teasing all day but they did have to get some things done before everyone else got there. She made sure not to stare at his erection and instead she walked toward a closet and asked him to bring the clothes on the bed. He grabbed the nightgown and started over until she called back “can you grab my panties too, dear?”
With the nightgown in one hand and the red panties in his other trembling hand Tommy followed her into the closet. When he got there, she was bent over doing something with shoes at the back of the walk in closet. He stood there staring. The thin slip tight across her backside showed every line of garter and panty. The blue panties and black garter belt and stockings were not really hidden by the tightly pulled thin slip. The sight was so erotic and arousing that Tommy stopped and was almost frozen for a minute even when Mrs. Jones stood up and turned around.
She smiled because she felt his tension and excitement. She reached out and said “Let me hang up my nightie while you hang on to my panties.” While she fiddled with hangers she kept talking partly because Tommy was not quite able to talk. “I always liked this nightgown because it makes me feel special and elegant. It’s like a special dress for a special night. Since I was all alone last night, it made sense to wear special panties too. Nice red ones, don’t you think that was a nice idea? To make me feel special I mean.”
Suddenly Tommy realized he needed to talk and not just stare at Mrs. Jones and her panties. “Oh, yes. I think so. I mean I guess so, Ma’am.”
“Tommy, dear, I suppose I should put the panties in the hamper here. You’re holding them though, are they dry or are still, well, you know.” She smiled knowing Tommy would have trouble with this not so innocent question.
Tommy looked confused but said “um dry.” He looked down at them and then back at her.
She took his one free hand in hers and smiled. “Sweetheart, I want to help you understand things better. I want to teach you. Maybe you don’t know that sometimes a woman gets excited and it might make her panties a little wet. For example, if a woman was in bed and thinking sexy thoughts and then maybe touched herself there, just like I’m sure you do sometimes, her feminine moisture would make her panties all wet and scented. Go ahead and smell them and you probably can still smell a little.”
She smiled and watched as he did as he was told and lifted the panties and smelled them, his face buried in the red silk. He then looked back at her and clearly couldn’t speak. So she just smiled and took the panties from him but quickly, accidentally dropped them. “Oops.”
She bent down and picked them up again but when she stood back up her head accidentally bumped him and his bulge on the way up. “I’m sorry,” she said and pretending to notice it for the first time. “Oh, Tommy, I’m so sorry. Did I cause that? Me and all my talk about panties and sexy thoughts. I feel terrible that I am making you uncomfortable.” Then she reached out and patted the top of the bulge like it was a pet and smiled at him.
Tommy had some self-control or he would have exploded right there. He was shocked but trying hard to behave the way he thought he should. But he had no idea what to do. He was in a woman’s closet talking about her panties and his erection but she wasn’t acting unusual or anything.
Mrs. Jones smiled and squeezed his bulge. Then she freed his erection from his underwear, peeling them down just below his bulge and his balls. “Tommy, I’m sorry I made it so big. It must have been hurting. You’re such a large young man. Do you know that you’re very big?” While she was talking, she used the hand with the panties in it to stroke along his shaft.
Tommy tried to talk. “But, I shouldn’t or I mean we shouldn’t.” Mrs. Jones shushed him and shook her head.
“Honey, all I wanted to do was relieve the pressure on you. Your nice, big penis looked uncomfortable and we’re in the closet here not out in public so don’t worry no one can see.” Tommy looked uncomfortable and nervous and a little embarrassed. “Oh dear, am I making you nervous? Are you upset that I talked about your penis? Should I not say the word penis?”
The whole time she was gently caressing him with her panties and hand and he trembled every time she said penis which made her want to say it more. “Does the word penis bother you, dear? I didn’t know what to say. It is a penis. A nice, big penis that got excited. That happens to a penis. I know some men might like other words. Would it be better if I called it your cock? Do you boys like to call them cocks now? Tommy has a nice big cock. It sounds dirtier than penis, doesn’t it?” She kept caressing and Tommy got more embarrassed. Each time she said cock she said it quietly and squeezed it when she said it.
Mrs. Jones saw that it was leaking on her panties and that Tommy was struggling. He couldn’t speak at all. She loved it. “Tommy, sweetheart, I feel bad that I made you so uncomfortable. I want to fix it and take care of this so we can go back to work before the girls get here. Is that okay? Can we finish our work before your mommy gets back? I think it would be better if your nice big penis calmed down before your mommy gets here.”
Tommy was gasping and Mrs. Jones knew just what she was doing. All the time she talked, she moved the panties to caress his balls and stroked his cock as she looked at him. Every word made him feel more excited, each time she said penis or mommy, he cringed and his manhood throbbed. Suddenly without much warning he exploded. She squeezed and he shot ropes of his cum straight out. they splattered Mrs. Jones neck and the top part of her slip making a sticky mess that dripped into her cleavage and got her slip all wet.
Tommy started to apologize. “I’m so sorry, it just happened.”
But Mrs. Jones again silenced him. “It’s okay, Tommy. I wanted to relieve you. I felt bad and I wanted to make you fit in your shorts again. But you have so much cum. Look at all over my skin and my slip. You’ve drenched me. See how wet the slip is? I can’t wear this when your mom and her friends get here. And do you see the gobs of cum on my neck slowly dripping down?” Mrs. Jones was smiling at him. The more she talked, the more his cock looked the same as before. She loved that his young cock stayed almost as hard after cumming as before and was watching it get bigger again.
She smiled and sat on the floor before pulling her soaked slip off and leaning back. “Darling, use both hands and grab my panties. Quickly. Do it now. Now rip them off me. You heard me. Do it now. They are very wet and I want them torn from me.” Then as Tommy did as he was told she moaned. The first obvious admission of her sexuality today. She then leaned back and puled him closer, his big cock throbbing. She rubbed the tip against her now well lubricated pussy and looked Tommy in the eyes. “Fuck me Tommy. Do it right now. I want you inside me.”
Then she put her arms around him, grabbed both cheeks and fell back pulling him closer as he thrust inside her. Now it was about her. She moved and squirmed and moaned shoving her hips to meet his and almost riding him from below. Her own orgasm was close, the whole day was building toward it and now she was finishing it moaning every step of the way.
Tommy wasn’t skilled but he was energetic and soon she was almost screaming underneath an awestruck Tommy. He was emptying himself again inside her but she was so lost in herself she didn’t notice. Until finally she stopped, out of breath, and satisfied.
Mrs. Jones sat up and subtly encouraged Tommy to move off her. “You get better get dressed quickly dear. I think your mommy wil be here soon and your pants are probably dry now.” Then she found the red panties and stuffed as much of them inside herself as she could before she put another pair of panties over them to replace the ripped blue ones. She smiled as Tommy looked dazed. “These will help keep your nice cum inside me dear. It will be nice to play cards with your mommy while I am filled with your cum.”
She smiled at him. “now hurry up and get dressed before the girls get here. And, Tommy, thank you for letting me have your virginity.”