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Staying with Mrs. Wentworth, Day 01

By: softspokenstephen



This is my first story and it develops a little slowly. Some people don't like that but I like a slow development. I hope you do to. It is obviously meant to be continued so if you have suggestions about things, I'd be happy to hear them and maybe make changes to make the story or characters better. I hope you enjoy this situation. 

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I'm 18 years old and should be old enough to stay by myself for a week when my single mom is off somewhere. I don't know why she can't see that. I heard my mom talking to her friend, an old teacher of mine.

"Doris, I know he's 18 but I can't leave him alone. I don't think he's prepared. He's sort of a young 18, really. I really appreciate you taking him in while I go away. I'll drop him off tomorrow afternoon on my way to the airport."

I fought with my mom over this but she was always over protective. I might not be the most experienced guy and she didn't exactly encourage independence but when a guy's 18, he doesn't want a babysitter, right? But my mom insisted. "You'll stay with Mrs. Wentworth and I won't worry about you while I'm off on my business trip. This is not open for discussion."

Not that Doris was a babysitter. Mrs. Doris Wentworth was the old lady who had been my teacher in fourth grade. There wasn't a Mr. Wentworth. In fact, I don't know if there ever had been. Maybe that's why she and my mom got along. Neither had a husband. She was an old lady who was always nice. Now I say old lady but really she just seemed old when I was in fourth grade. That was nine years ago and she was probably in her later 30s. She was in her forties and actually looked pretty good for her age. She was in good shape, dressed nice and was always nice to me even when she tutored me in high school. She might be kind of old, I thought, but she was nice.

When Mom dropped me off, Mrs. Wentworth lived more than an hour away but on the way to the nearest big airport. I took in a suitcase with some clothes and Mom talked to Doris. Doris teased her about her trip and told her to be a good girl and try not to get in trouble. Then they both laughed in a way that made me uncomfortable. I think they were probably talking about sex or drinking. I knew my mom probably had a sex life but I didn't think about it much. I did think about sex itself a lot. I was 18 and as horny as any 18 year old you'd meet. I thought about sex day and night. I didn't have much experience at all first hand but it didn't stop me from having a fantasy life.

Then mom got serious and gave me a kiss but it was like when she was going out and I was 12. I was an adult now and she didn't treat me like one. "Now, Stephen, you be a good boy and listen to Mrs. Wentworth. While I'm gone, she's in charge of you. I will be very angry if you're a bad boy. You listen to her, help her out, do anything she tells you to, and show her how nice and obedient you are. Make mommy proud and be a nice young man." I felt like she didn't notice I was a grown man. I was an adult not 12.

"Aw, mom, c'mon. You're embarrassing me. I'll be fine. I would have been fine at home and we're not even near any of my friends...."

"Stephen!"

"All right, okay, I'll be fine. This will be fine. Everything's fine. Don't worry. Have a good time."

Mom smiled. "That's better, but it's not to have a good time, I'm just going because I have to go for work"

Doris smirked and Mom gave her a dirty look.

But Mrs. Wentworth put her arm around mine and said "Don't worry, Stevie and I are old friends and we'll be great. Run along or you'll miss your plane." I didn't like being called "Stevie" but I liked her attitude and we watched mom go.

Then Mrs. Wentworth told me to grab my suitcase and led me up the stairs to my room for the week. Following her, I realized she wasn't that old really and actually had a nice ass at least how her skirt which was a little tight cupped it. I kind of liked following her even if it was weird to like looking at the surprisingly tight ass of the "old" lady who was my ex-teacher. We walked past a big bedroom which was hers, really nice with a giant bed with posts and then down the hall to the room for me. It wasn't exactly masculine, like no sports pictures or anything definitely manly but at least it wasn't pink or girly, just kind of blue. I put my suitcase on the bed and she told me she cleared out half the dresser for me. But it isn't like I had a lot of clothes so I just put the suitcase on the floor when she said "come down to the kitchen when you're settled."

I walked out maybe 60 seconds behind her, pretty much "settled." She smiled in the kitchen and had me sit at the table while she gave me lunch. 

While she cooked some soup and made a sandwich, she talked about how nice it was to have me and how it was like playing house. Then she laughed. I laughed too but mostly I stared at her ass the whole time. I liked it and I noticed every time she bent down (and she bent down a whole lot of times, a lot more than I hoped for) I could see the lines of her panties bumping out. I liked that. When she gave me lunch, she put a plate in front of me bent over and I noticed from my angle her blouse wasn't real closed. I mean I could see in and saw a pretty good look at a black lace bra. I didn't expect that. I was surprised and tried real hard not to react even though it made me hard. She didn't notice me staring down her blouse and I thought it was probably an accident. But we had a nice late lunch and just talked about how things were going with me. I hadn't started college and didn't know what I wanted so we mostly talked about that.

Then she grabbed my hand across the table and held it (which I liked) and said "now, sweetie, I hate to do this and run off on you just as we've started our little time together but I have to go out to a charity dinner as a favor to a friend. I didn't know you were coming yet when I made this date but I won't be late I promise." Then she laughed at me, I guess I looked funny. "Oh sweetheart," she patted my hand. "Are you jealous? It's not a real date, I'm just going with friends."

I don't know why she said that so I said "What? No, of course not. What do you mean jealous? Oh you're kidding. No, I don't care what you do. I'll just hang out and do whatever." She smiled and said "that's a good boy. I promise I won't be late. I'll be home by 9:00. You can hold me to that. I don't want to be spanked for being bad so I won't be late." Then she laughed again. "Now I have to go get ready so you make yourself at home. Think of this as our house for the week." And she went upstairs.

It was really weird. I didn't think I looked jealous. That would be stupid. What do I care what some old lady I'm staying with does? And what the hell did she mean getting spanked? That was weird. Probably some older person joke. It wasn't like I'd let her spank me if I was late. And did she think I would bend her over and spank that gorgeous ass of hers? Ridiculous. I sat there thinking about it for ten minutes, though. That was weird but thinking about it was at least a little sexy.

I heard her up taking a shower so I guess she was going to change to go out. I wandered around downstairs realizing I couldn't call anyone and have them come over or anything. We were way far away. Not that I did a lot socially on a normal week but I was feeling sorry for myself. I looked around the backyard, couldn't see any neighbors or anything, just a lot of land. I was turning on the TV when she came down stairs and called out that she was going to go. I turned and was speechless. She stood there smiling. 

She was wearing a really red tight satin dress. It was shiny and it hugged her. You could tell she had a nice ass and I saw she had a nice figure everywhere too and nice breasts. I couldn't believe I was noticing this about a lady who was even older than my mom. But she was very hot and the dress made her super hot. I just stared and found myself wondering what was under it and how come I never noticed how hot she was. I mean maybe in fourth grade I sort of liked her like a kid likes his teacher but wow! She asked me if it looked OK? It did but I just nodded not able to speak. "Oh, are you sure Stevie dear? You look surprised. Is it the wrong style for an old lady? Do you hate it?"

"Gosh no, Mrs. Wentworth, it looks amazing and you're not old or anything. You look awesome." She smiled and said, "aren't you the sweetest little guy?" Again I liked the attention but both she and my mom had a way of making me feel 12. I mean what adult 18 year old wants to be called a sweet little guy?

I was kind of hard and horny because I was 18 and always horny actually and I had just realized that whatever else happened she was totally hot for a woman her age. Hell, in that dress she was hot for anyone. I didn't want to just sit on the couch and play with myself so when she left I decided to explore. So I walked around. It was a pretty big house. But very orderly and not messy at all. There were a lot of books but whatever I felt like doing, reading wasn't it. I walked into her room. I felt kind of weird, sort of forbidden like it was a private place I shouldn't be. Which it probably was. She was very neat and nothing out of place with her bed completely made. I did open a drawer or two and even one with her panties in them. I looked them like they were a basket of jewels. And there were lots of colors and they weren't boring. But I was afraid to touch because everything was so neat.

So I wandered in the bathroom. This was a little messier. But not a lot. A hairdryer was out and the tub was wet still but it was a hell of lot cleaner than mine at home. Then I saw the black bra I had stared at earlier laying on the floor. I picked it up and stared like it was magic. I have a total thing for women's lingerie. It's so erotic and mysterious. It was very feminine and it was black which made me hard. Lingerie always turns me on so since I was alone I actually unzipped and let out my cock. I didn't have much real experience with women but I masturbated lots of times. 

I pulled the bra and back and forth across me to feel it against my skin but was about to leave when I saw the panties. They matched. I picked them up and smelled them. I could smell a hint of perfume and her on them. I tried not to but I grabbed them and started jacking off even though I knew I shouldn't. In a few minutes, more like 45 seconds, I grunted and shot a load, catching it with the panties. Oops. I looked at the pool of white cum caught in black silk panties. I liked it and liked doing her panties like that but afterward kind of thought maybe I shouldn't have done that. So I wadded them up and found the dirty clothes hamper and pushed them down under stuff. I threw the bra in too and figured she wouldn't notice.

I knew I was a perv but I felt better because I came. She wouldn't know and I'd be more relaxed. But quickly I left her room after rinsing my dick off in her sink. I went back downstairs and watched TV. I just watched ESPN for a while to get my mind somewhere else. I figured she'd actually be pretty late. No way you go out looking like that and get home at 9. But I was wrong. I heard a car outside at 8:45 and then the garage door and hear her come in. In the family room, I was in a chair and hear her heels making clicking noises slowly across the floor as she walked through the kitchen and dining area and finally came into the living room, leaning against the doorway and looking just as awesome as when she left.

I sat in a chair with my feet in front of me on a stool and looked at her and just stared. I didn't say anything for like a minute and then I just said, "uh, hi." She was standing there leaning against the doorway with one hip out. Her legs looked awesome between the heels and some white stockings. I hadn't notice every detail before she left but wow she looked like some fantasy woman in shiny satin. It was only a couple hours since I had used her panties to get off but I was instantly really hard in my pants.

She looked at the clock and said "not even 9 yet and I'm home, that was the rule and I followed the rules. It's good to the follow the rules isn't it Stevie?" Then she walked into the room slowly and stood at the edge of the chair looking down on me, smiling, and making me a little self-conscious. "Um, yeah, I like rules. Of course. So did you have...."

But she interrupted and told me to sit up, reaching down and tapping the bulge I wasn't hiding. "Sit up and cross your legs sweetie-pie. You need to be more discreet about some things."

I turned super red and sat up and crossed my legs to hide myself. I was more embarrassed than I'd ever been but I didn't know what to say. "I'm sorry," I mumbled.

She sat on the stool I had just been using and patted my hand again. It made me feel little. "Don't be sad my little sweetie. Mrs. Wentworth is just trying to teach you like I always do. You were always a good little student and I know you'll be a good boy if someone just shows you what to do. I know you'll be a good for me won't you? Are you my good little student, sweetie?" She smiled at me and I nodded. But she kept looking. "Say it Stevie dear. Tell me"

I wasn't sure what was going on but I said what I thought she wanted. "Yes. Sorry. Yes, ma'am. I'm your good little student." She smiled.

I looked down kind of embarrassed. She was turned with her legs crossed so I just stared at her legs. I watched them from her heels and all the way up noticing that her legs the way they were pointed sideways made her skirt high. I could see all the way up her thigh and to some white lace band at the top of a stocking. She didn't notice how much she was showing I guess. It made me harder to see it and to know that it was an accident but I kept my bulge hidden.

She smiled, half stood, leaned over and kissed my forehead. Then she stood and said "OK, now it's bedtime. We have a busy day tomorrow." As she walked away, she stopped and looked at me and it was clear she meant bedtime for me too. It wasn't even 10:00 yet. But I followed her. She walked slowly which I enjoyed from behind. She took the steps real slow I guess because she was still wearing heels which she really should have taken off to climb the stairs but I loved it. I'm surprised I didn't cum in my shorts. 

She went into her room and stopped me before I could keep going. "Stevie, dear, remember about helping me like mommy said...." 

"Uh ok, sure." What now? I thought. And I wish she didnt say "mommy" like I was some kid.

She stood in front of the dresser looking in the mirror and said to me "Mrs. Wentworth can't reach her dress's zipper. Be a good little dear and help unzip me. I'm sure you help your mommy that way too."

That seemed really really weird to me but I wanted to be helpful so I reached and carefully pulled the zipper down. I realized that I could see some skin and her bra straps from the back and I was going a little lower. But then she dropped something I think because she suddenly bent over and down to the floor. I lost my grip on the zipper and her backside pushed out so that her beautiful satin covered ass pushed back into me and against my rock hard bulge. Just for a minute and then she stood back up. I finished unzipping a few more inches down. But I could see the top of red panties and also what I figured out was a white garter belt. I had only read about those and never seen them in person but it was hot. It was funny that her bra and her panties were both red like the dress even though no one was going to see them. Well, almost nobody because I saw the back of them at least. It was a lot more erotic to me than it would have sounded.

She turned around, her dress still up but loose, and kissed me very softly near my ear. "Thank you for being my good little helper, now run off and put on your jammies and get into bed." I was confused. It was sort of seductive and sort of belittling. And it's not like I wore "jammies" like some kid. I wore shorts and a T shirt and I got into bed. A lot of nights I jerk off thinking of someone my age named Julie but tonight Julie was replaced by Mrs. Wentworth. It was weird but I came pretty fast and fell asleep and slept great wondering what tomorrow would be like. 

Staying with Mrs. Wentworth, Day 02



This is the second part of staying with Mrs. Wentworth. A lot of people gave me great feedback and made suggestions I tried to use including more details on the clothes which I tried to look into more, doing some research and using some suggestions. Thanks to all of them for making this better than it would without the advice. I can see keeping going with this story but I'm also trying to think of new ideas for new stories too so if you have suggestions like that I'd love to have them. Hope you enjoy. Just a reminder, this is a kind of slow story more than a quick action thing.

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The next morning I woke up pretty early from the sun coming in the window and just from being in a strange place. I'd almost forgotten that my mom forced me to go stay with her friend Mrs. Wentworth while she was gone on a trip for her work. Mrs. Wentworth was a teacher of mine a long time ago but now that I was 18, almost 19 actually, I thought of myself as an adult and found it pretty insulting to stay with some old lady friend of mom's. OK, maybe she wasn't completely an old lady. She wasn't really old, maybe in her forties. And she seems mostly cool so far and it isn't like I had anything else going on so I shouldn't complain. Plus it turned out she was actually pretty hot for her age. Actually for any age. I tried to be subtle about it though. I wasn't going to run around just staring at her. 

Anyway, I woke up and she poked her head in the spare room I was sleeping in. "Hey, sleepyhead, come on down for breakfast as quick as you can."

I'm always hungry in the morning so you didn't have to ask me twice. I got up. No reason to get dressed for the day yet so I went downstairs in my shorts and T shirt. She was busy getting stuff together and just said over her shoulder, "have a seat, Stevie dear. I've got some food for you." I liked that she was real friendly but "Stevie dear" always seemed kind of belittling. Not that she meant it that way and I didn't really mind it that much.

I watched her because, well, why wouldn't I? She wasn't dressed completely yet either. I'm not saying she was undressed but she still in her pajamas. At least, I assumed she had on her pajamas or nightgown or something but all I could see was a satiny bathrobe which came down to her knees but not over them. It was a light purple in color and had lace cuffs on the sleeves. It wasn't revealing or anything but it was real elegant and more formal if a bathrobe can be that way. It was also tied pretty tight so it didn't hide her figure but showed it off. 

In fact, it showed it off real well. While she was talking she was bending down and doing something on the floor or in the cupboard I think. Anyway, when she bent it cupped her ass real nice. I figured out the night before what a fantastic butt she had and this was really showing it off for me. It was an accident but I enjoyed it since it happened three or four times. I was almost disappointed when she brought me a glass of orange juice and put down a plate of eggs for me. I smiled and said thank you. I also looked at her and even though she wasn't giving me a look down her robe, the tightness reminded of how nice the top half of her shape was too.

I think I might eat too fast because I ate the eggs and three bacon pieces in about two minutes. The orange juice didn't make it long either. So I got up and took my plate out to the sink and tried not to stare at Mrs. Wentworth anymore. I didn't try real hard not to stare but at least I wasn't obvious about it. She finished messing with the coffee machine and stretched as she turned around. I have to say that I don't mind when a woman wearing a tight satin robe arches her back and stretches. I might have stared then but who wouldn't?

I'm not used to being around people in the morning I guess because I didn't think about things. Suddenly, she looked real seriously at me. "Stevie, honey, we need to teach you a few things." Then she grabbed the big tent in my shorts. My hardon was sticking up and real obvious. I didn't know what was going on though because I don't really get a lot of women grabbing me by my hardon like it was a handle. It's not like she was making a move or anything (of course). Instead she was humiliating me just a little bit. She said, "I understand how you young men are but little Stevie here needs to behave in front of company so I want you to take him upstairs and put on a pair of underpants to keep him under control." Then she let go of me and slapped me on the ass to push me along. "Now hurry up so you can wait on me."

I was totally humiliated. I mean it was cool that she touched me even through my shorts but it was humiliating the way it happened. It was exciting though. So I hurried up, threw on a pair of tighty whities under everything and came back down. She looked carefully at my crotch as I came into the kitchen. Like she was examining me. I was sort of aroused by being examined so carefully but really it was more like a walk of shame. But then she smiled and said "now be a good boy and bring me a bagel and cream cheese and coffee. I'll take my breakfast on the deck."I guess I looked surprised so she said, "remember what your mommy said about behaving like a good boy. Now, get to it." And she smiled and went to the deck.

It annoyed me for some reason when she talked about "what mommy said" like I cared what my mother said. And I never called her mommy. But she was right. I did want to be cooperative. Not because my mom wanted me to but because I liked Mrs. Wentworth. I kind of wanted to take care of her After all, she made me breakfast so I would repay the favor. She had a bagel out on the counter so I just toasted it and got a tub of cream cheese out of the fridge and spread it on a plate. Simple. The coffee was in the coffee maker already dripping. I was about to ask her if she wanted a big mug or what when I saw she put out a whole tray with pot and creamer and cups and stuff. There was sugar in the bowl so I put some cream in the creamer and poured the coffee into the china pot. I put the plate on the tray and carried the whole thing out like a waiter. I was actually pretty proud of how I was taking care of her. Then I put it down on the little table by her and said "your breakfast, Mrs. Wentworth." Like I was a waiter.

She smiled and had me pour her a cup with cream and one sugar while she ate part of the bagel. I sat down too and she told me to have coffee. I don't really drink it but it seemed very polite so I did it. I had a cup the same way and sipped it. I liked it a little but what I liked more was 

looking at her legs the way they came out of her bathrobe. She was laying back on a chair with her legs spread out and crossed at the ankles. Nice legs. Awesome legs. I think I like them better in stockings but whatever. Her legs were great anyway you looked. I guess I never thought about it before but I was definitely a leg man.

After a few minutes, she reached her hand out to pat my hand and said "thank you for being a good waiter. I think the week is off to a good start." I was going to say "it would be if you wear that awesome dress from last night everyday" but of 

course I didn't. I just enjoyed sitting there with her appreciating me and staring at me a little bit.

The she let go of my hand and sat up a little bit. She said "Stevie, dear, I want to ask you something." She looked at me and said, "are you a virgin?"

I almost freaked. I mean who the hell just asks that? Especially someone I hardly know. I almost got up and walked out. I was angry, mostly angry, maybe a little embarrassed. Like I'm going to talk about this with some lady who used to be my teacher. "No. What? I mean of course not. Why would you think that? Why are we even talking about this? I'm not, you know, I get around and all that."

She smiled but didn't laugh. "Stevie, don't be mad or embarrassed. You know sweetie that you can tell Mrs. Wentworth anything and it will be just between us." She smiled but I didn't say anything, I was almost unable to talk. She patted my hand again and said, "But you haven't actually had intercourse have you? Mrs. Wentworth knows these things." I didn't say anything and I was just red and pissed. I mean I'd done stuff, maybe not a lot of stuff and maybe she was technically right but why were talking about it? It was like she could hear my thoughts though. "It's okay, darling. I don't think boys should have sex when they are 15 or 16 or 17. I think it's good to wait you turn 18. It's important to wait and we wouldn't even be talking if you weren't an adult."

"I'm almost 19 actually and whatever I do or not is because I decide to and want to and I don't need anyone's permission. I don't know what my mom put you up to but I'm my own man."

Then she patted my hand again. "Of course, my sweet Stevie. Of course. You know your mommy and I didn't even talk about this. I would never want to get you in trouble with your mommy. But I know you trust Mrs. Wentworth and I know I can help. Wasn't I a good teacher all those years ago and you learned to read? You know you can trust Mrs. Wentworth don't you, honey?" She looked eager and 

I couldn't really be mad so I just shrugged. 

Actually I kind of did trust her anyway.

She smiled and looked real happy. "Oh goodie. I know this would work out! Mrs. Wentworth will help you be comfortable with women. I know. I know you are but I'll help some more. Just little things. Nothing too personal or intimate of course. How about you and Mrs. Wentworth have a nice little date tonight?" She looked at me again and I didn't say no or run off anyway.

"That's the spirit. That's my good boy. And we won't even tell mommy about it. Now, we'll go somewhere nice and have a nice dinner. That's all we'll do but it will be fun, won't it? Of course it will. Did you bring some nice clothes for your special date with me?"

I didn't know what to say and I had to humor her anyway so I just went along and thought I might get a few tips on small talk at dinner and stuff like that. "But I only have like shorts and stuff so maybe somewhere kind of casual."

She frowned and said, "No, no. That won't do. I know. We will go to your mommy's house. It's only an hour and you can pick up a suit or whatever you have. I'll change and we can eat at a nice restaurant near there. I don't get over that way much since I stopped teaching. We'll have a long drive home to our house but that's fine. No, it's settled. We'll leave in a little while."

We skipped lunch so we'd be hungry, she said. Then she packed a small bag so she didn't have to be completely ready for all day and we left.

Mrs. Wentworth had a nice car, a Mercedes, and she let me drive so already she was getting more awesome in my book. When we got into my town, she wanted coffee so we stopped at a Starbucks. I ordered hers and I got a mocha drink for me because I only like coffee a little. While I got the drinks, she went to the ladies room and I ran into a girl I knew in high school. Julie was hot mostly and I liked to dream about her but she was not exactly super friendly. I guess she was actually kind of rude to me most of the time. She asked me what I was doing there like she owned the place and laughed when I said I was just getting a drink and I had a date later. I guess I was trying to sound important but she was just being bitchy. Something she was good at. "Sure you do Steve. You going to take your hand out to dinner and show it a good time? I'm working tonight so if your hand gets hungry bring it to Anthony's." And then she laughed and walked out. 

I suddenly noticed Mrs. Wentworth behind me and she was watching Julie leave. "Stevie, honey, what's the bitch's name? Is she always like that?" She looked kind of angry too.

I told her not to worry. Some people just like to tease. We let it go and went to the house. Anyway, we went to my room. I really only have one suit (and even that I never wear almost ever). My mom likes it and it's basic gray with a red tie. She says it goes with anything. Mrs. Wentworth said "it'll do. Let me do a few things about reservations. I decided I want Italian and maybe we'll go to Anthony's tonight."

I thought I didn't want to see Julie. But then again maybe I did if I had Mrs. Wentworth with me. Maybe. But probably I just hoped we didn't see anyone. Anyway, she left my room and got ready in my mom's room and I got ready. I checked myself out in the mirror. I don't know fashion exactly but I think I looked good. I was like a banker or a CEO. I probably looked ten years older. At least I thought so. I sat in the living room downstairs waiting for Mrs. Wentworth because she took a little longer than me.  

When she came downstairs, I can hardly describe it but I could see why she took a lot longer than me. Let me try to describe it. She almost floated down the steps, not wearing shoes yet but she paused to put on her high heels. Putting on heels while standing up really forces the guy watching with his jaw open to stare at your legs and try not to drool. The shoes were great too. I think I really like high heels. Hers had long pointy heels. The heels were black not metal or anything and the shoe wasn't shiny it was dull, like it was fabric not leather. The toe area was covered by a sort of wrapped fabric, not quite a bow but gathered together, and it left the toes open to show a little. I saw because she waved her feet at me after she put them on and asked "do you like new shoes, Stevie, darling? I bought these special for you." I knew she hadn't because it wasn't like we stopped at the store but that's OK.

I smiled and nodded. She was great looking and when she got closer I just said "holy shit!" She looked mad but a fake mad and said "now, now, you watch that mouth darling. Don't be a naughty boy!" And then she laughed and told me to go outside. "You need to knock on the door and pick me up silly." 

So I went out and knocked and said "good evening, may I escort you to dinner?" She liked me getting in the spirit as we walked out to the car. She was holding my arm and said "walk slow for your date, sweetheart. Stop trying to look down my blouse. A woman appreciates subtlety." I was going to say I wasn't trying to look but I was. She gave me pointers though. "Stephen, instead, let your arm drift to my waist. There, hold me lightly and don't go too low to be obscene. Are you ready for a secret?"

I stopped walking not sure what she meant. She said "Move your fingers a little and tell me what you feel."

"Uh, nothing really, just a skirt I think."

"Silly Stevie. No, dear, feel there? That's the top of my panties. Feel the strap along here?" She moved my hand. "That's a garter. They're not comfortable or practical so if your date is wearing them she probably went all out to dress up for you. Now pretend to be subtle like I didn't notice anything and just help me into the car."

I opened her door and she smiled as I helped her into her seat. Her dress wasn't short exactly. It was very expensive looking. It didn't have sleeves and it was a little low in front but not too low to show off a lot. The top was very form fitting which works when you have an upper body like Mrs. Wentworth but makes it hard not to stare. The skirt had lacey stuff over the top of an almost shiny black material. Like I said it wasn't high but when she got into the car, it went up a lot and I saw her legs almost completely up her thigh including lace at the top of her stockings. But I didn't see all the way up.

She adjusted like showing me so much leg was an accident. Maybe. I drove to the restaurant and we parked. Immediately, she ran off to the bathroom while I went and got the table. She made the reservation under Stephen so I felt good. But while I was talking to the hostess getting ready to sit, that Julie came by. I really was hoping to avoid her and she was even more bitchy if that was possible. She gave me a real bad time about being alone and about what kind of person goes out to eat by himself. Finally, the hostess glared at her and told her to stop. She was about to go do her job when Mrs. Wentworth suddenly swept into the area all energetic and asked loudly "did you get a nice private table honey?' She took me by the shoulders and whispered, "don't ask just put your hand on my ass and squeeze it right now." I was shocked but did as I was told (and why the hell not!) and she kissed me. Not softly either. She grabbed and pulled me and kissed me long and hard the most erotic kiss I ever had even without any tongue.

The she let go and turned like it was something she did everyday. My hand fell off her gorgeous ass and she smiled at Julie as if she was our servant. "We'll need a private table if you can." Julie was dumbfounded (which was awesome!) and just said "uh, do I know you?" Before I could explain, Mrs. Wentworth just said "I'm sure we don't. I'm Lana. Stephen's lover." Then the hostess took us, glared again at Julie and led us to a table. The whole time I'm all casual and trying to look like this is just the way I am on the outside but inside I'm screaming "what just happened? Did she really have me grope her and that kiss was incredible. And why did she say I was her lover? Lover? And since when did she become Lana, I thought she was Doris Wentworth?"

Julie wasn't our waitress but she would look over when she could and Mrs. Wentworth got real close to me. We were in a corner booth type table so she could slide pretty close. I was about to explode when "Lana" leaned over like we were whispering like lovers do. But she said, "now don't panic, Stevie dear. I had to do that. Your little friend is a bitch and I wasn't about to stand by and let her treat you like she tried to do. We watch out for each other don't we, darling? And it wasn't so awfully terrible to be kissed by Mrs. Wentworth was it, sweetie?" Then she giggled 

I smiled and felt more at ease and so grateful for her caring enough to hate Julie. She was right. Julie was a bitch. But I had to ask, "I mean, wow, it was hot. I mean you're hot. It was amazing. But who's Lana? I don't understand."

She playfully grabbed my knee and said "oh, I never come into this area anymore but it's possible she was a student a long time ago. So to be careful I decided I want her to think I'm your somewhat older girlfriend not your old teacher. I think it worked. Did you see how she looked when I kissed you and when I said I was your lover." I laughed but to be honest I didn't look at anyone else or notice anything. 

I know Julie was staring at us the whole time we were eating and I didn't care. Finally she found a way to come over to our table even though she wasn't our waitress. I could tell Mrs. Wentworth was pissed though. Her eyes looked very very angry. Julie ignored her and tried to start talking to me. So Mrs. Wentworth leaned over and started licking the side of my face. She whispered in my ear "trust me and act calm and natural." 

I was distrated by her tongue in my ear but almost immediately, she reached down and unzipped me and reached in and pulled out my cock. I was still perpetually hard from earlier and I knew Julie couldn't actually see but she knew. For some reason it made Julie really mad. I didn't know what to do until I felt Mrs. Wentworth not just stroking me but start to massage my balls and whisper "let it go, don't hold back." I tried not to be completely obvious but I came into her hand and she stopped sucking on my ear.

She smiled at Julie, wiped her hand with the napkin below the table and then handed it to Julie. "Run along and take care of this for us." and with that Julie was dismissed and speechless. Mrs. Wentworth suggested we leave without dessert and quietly slipped me cash under the table to pay for the meal. I was speechless and just zipped up before the waitress came back. 




Staying with Mrs. Wentworth, Day 02



As we were leaving, Julie came over not quite able to be bitchy anymore but still looking curious and a little dazed. "Aren't you guys having dessert?" she asked. Mrs. W. was totally into the Lana character when she leaned over and whispered but not too softly "I need something sweet with a nice gooey cream filling so Stephen is going to fulfill me which he's so good at." Julie completely froze. We walked out, got in the car and drove off. It was incredible!

I was feeling awesome as I drove. "Stevie, honey, head back to our house, no need to go back to your mommy's place." She looked into my eyes while I was driving and looked worried. She didn't say anything for a long time and I felt weird. I wasn't sure if I should say something or apologize or what she expected. Then she reached over and grabbed my hand and squeezed it. 

"Stevie, darling. I feel terrible. That shouldn't have happened. I didn't mean for anything to happen. Are you mad at me?"

I just stared at her. But I was driving so I couldn't stare long. And I said, "Mad? Why would I be mad? hat was awesome. I mean Julie was totally put in her place and you were amazing. I didn't know that anything, well, you know, in public and all."

She looked sad suddenly and I guessed I said the wrong thing. "Oh, Stephen, dear sweet, Stephen. I knew I shouldn't have done that but that silly little bitch got to me. Sweetheart, please understand that was just protecting my Stevie dear. I know it was wrong of me to let you squeeze my ass tonight, and you know it too? It was probably naughty of us and we just did it to teach that little bitch a lesson. I don't want you to get the wrong idea about Mrs. Wentworth, sweetie-pie." She didn't mention making me cum in a napkin but I was guessing it wasn't the time to bring it up.

"No, Stevie. I must apologize to you. It was wrong of me to get carried away. Mrs. Wentworth was a naughty girl and broke the rules. And after I warned you the other day. I feel terrible. I apologize completely for teaching wrong and setting bad example." And then she looked sad like she thought I'd really be mad.

Talk about hot then cold. My head was almost spinning so I didn't know what was going on. But I guess I always knew it was not a real thing so I said, "Yeah, no, sure of course. I know it was just a thing we were doing. Like roleplaying or something, right? A play or something like a trick. I didn't get the wrong idea at all. No, you weren't naughty or anything. Don't even think about it." Not that I wouldn't be remebering it for a real long time but I really sensed she wanted me to say what I said.

She squeezed my thigh and said "I knew you understood. Such a smart young man. Roleplaying is exactly what it is like. Roleplaying." She paused before continuing and looked thoughtful. "Oh, and of course as part of your lesson you know that on a first date you would never kiss that intensely in public or grab a woman's ass in front of other people that way. I haven't forgotten that I'm teaching you still. But it doesn't change that I was naughty. Terrible." She smiled though and it wasn't long before we got back to her house or our house as she kept saying. 

When I got out, she stayed in the car until I realized I was supposed to open her door first. So I opened her door like the gentleman I am (I was wearing a suit after all) and let her out. I was very polite and tried to be subtle as she wasn't careful with her dress and I got a huge look at her thighs. I walked her to the door and she stopped and said very formally "thank you for a lovely evening, sir." I'm thinking I get the game now and say "my pleasure, Ma'am" Then she leans in and kisses me. It was a lot softer and maybe less erotic than the restaurant but it was slow and soft with wet lips. In some ways it was even better than the one inside the restaurant.

The she giggled and said "lesson over" and grabbed me and we went inside. The date was over.

"Honey, be a dear and get me a glass of wine. There's an open bottle in the fridge." Now we were just people hanging out. Me visiting Mrs. Wentworth and waiting on her a little bit. She went and spread out on the couch and waited for me to bring the bottle and a glass. I poured her a glass and then went and sat down and loosened my tie. She drank the one glass pretty fast though and then stood up and said, "well, I guess we should get this over with."

I have to confess I had no idea what she was talking about. She stood in front of me and said, "Stephen, I was a naughty girl and I am truly sorry and want to formally apologize to you. I know what I did was wrong and this is only what I deserve." Then she pointed to a different chair and told me to sit in it. I was confused. Very confused actually. So I said, "what's going on?" 

She looked at me like I was dense and said "my spanking obviously."

I didn't see that coming. I had no idea what to say but I just moved slowly and waited. I nodded my head as if to say, "oh yeah, that." But inside I thought "what the hell, does she really think, how strange is this?" 

She started to bend down and then thought for a second and said "I can't ruin this dress that way." So before I knew what was happening (not that I would have tried to stop her), she reached behind her and unzipped and took off her dress, folding it neatly on a chair. I stared. Maybe I was subtle in my stare but probably not. I was just going along at this point. She stood there in some really pretty underwear. Her stockings that I had seen most of were black and they hooked by garters to a black garter belt. I think garters and garter belts and stockings were my new all-time favorite clothes. her bra and panties were mostly black with some white silk on them too. I think the black was sort of sheer and over the white. But whan a gorgous woman in her underwear stands in front of you ready to be spanked, the world moves in slow motion.

She looked real sorry at me and then got down and bent over my lap. The panties were mostly black in back when they covered her ass. If I thought she had a beautiful ass when I was following her up the stars, this was even better. I was harder then I'd been the whole time and that's saying something. The front of her panties pressed against my leg, My hardon was in an OK spot but when she squirmed, it pressed her stomach a little. Her breasts were over the other leg and she turned her head to look up and say, "I'm ready to be punished Stephen."

I wasn't sure exactly how hard to spank so I smacked down on her ass once a little hard but not real hard. I liked the way it felt when I sort of slapped her beautiful butt. She gave and I heard her say "OWW" or maybe more like"ohhh." Like she was surprised and squirmed to get comfortable. I probably should have told her to stop squirming but I didn't mind. I smacked her three more times each time getting a slightly slower "Ohhhhh." I was going to stop but she didn't move or get up at all. She was breathing heavy too. So I smacked a little more. Not harder and I might have let me hand rest for a minute between smacks.

After about twelve smacks, her "Ohhhs" were very long and coming from in her throat so I knew she wasn't really hurt. She also wiggled a lot between smacks. But after twelve, she got up quickly, very out of breath and said quickly "Thank you, Stevi, I deserved that. I'm going up. Say goodnight when you walk by my room." and she ran quickly up the stars.

I sat there for a long time. I wasn't sure what happened. But I wasn't complaining. After fifteen minutes, I went up to bed myself. her door was open so I looked in to say goodnight. She was already in bed under the sheets and blanket. I didn't know what to say so I just said "Ok, good night Mrs Wentworth." She smiled and said "thank you for coming to say good night, sweetie. I had a very nice date tonight with a nice gentleman." I smiled and said thanks. I wasn't sure what else to say.

"Stephen, honey, when someone is naughty that person is punished and everything is forgotten. It's erased and we never think of it again. Now do Mrs. Wentworth a favor and take her clothes and put them in the hamper inside the bathroom over there." I looked and found her underwear all in a heap right next to the bed so I picked them and walked them to the bathroom. I paused and thought a little when I noticed how wet her panties were. The ones that were in a pile on the floor of her otherwise spotless room. Out of sight, I took a secret sniff of them before throwing them in the hamper.

I walked about of the bathroom and said good night. She said "night night sweetie, go put your jammies on." Then as I was closing the door, she stopped me. "No, no, honey. At our house, we don't close the door on each other. My door is always open for you because I told you that you can trust Mrs. Wentworth. My open door and your open door and symbols of that." Then she blew me a kiss and I went into my room and slept. I'm pretty sure I had the best dreams I've ever had and it was only my second night there.



Staying with Mrs. Wentworth, Day 03



This is part three of the scenario. I'm enjoying crafting Mrs. Wentworth and I hope you do too. The story and its development are very slow. I should say I have benefitted from a lot of advice from commenters even if the story doesn't always go exactly like some suggestions. This is my first story and it's a learning process. I hope you enjoy.

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The sun woke me up again and it took me a few seconds to remember where I was. I remembered that my mom had forced me to go stay with her friend Mrs. Wentworth while she was gone for a week. I resented it. I was almost 19 and old enough to live on my own if I wanted but I humored my mom. Mrs. Wentworth was my teacher in fifth grade and that made it more humiliating. I should be on my own not staying with some old lady who used to teach me. Actually, she wasn't that old really. A lot older than me but probably around 40. And she turned out to be very nice. I wouldn't admit it to my mom of course but I didn't mind staying with Mrs. Wentworth. I was starting to like it really.

As the sleepiness wore off, I remembered the events of the night before (see Day Two). I started thinking about everything but mostly about Mrs. Wentworth taking off her dress and laying over my lap in her very nice lingerie and having me spank her for supposedly being naughty. I started thinking and doing what I usually do in the morning which is jerking off. I slipped off my shorts and used them while I stroked to keep from making a mess. I was living in my head the night before and not really noticing anything else so it wasn't very long before I came and emptied myself. I sopped it up with my shorts and was catching my breath when I thought I saw some movement by the door. 

I forgot about Mrs. Wentworth's open door policy. Her door was always open symbolically she said so our doors shouldn't be closed to each other. Maybe she walked by or something. I hadn't noticed anyone but then again I was in another place so would I have noticed if anyone watched? I bet she'd have said something if she saw me there doing my thing. A few seconds later though, I heard her call out "Stevie, honey, are you up?" I had only a split second to toss the sticky shorts on the floor next to the bed and pull up the covers to cover myself.

She came in with an arm full of laundry looking rested and energetic. "Hi, sweetie. I'm just doing a load of necessities so I thought I'd grab a few things from you. Let's see." She looked around and I said I was okay but she grabbed a shirt and shorts from the chair and put them in her arm pile and then before I could think of anything to say she bent over and grabbed my fresh shorts off the floor. Her hand must have squished and felt the pretty big load I had sopped up. But she just squeezed it in her hand, looked at me, smiled and kept a tight grip on the shorts. Then she said "come down when you're ready, dear." 

I waited until I heard her going down then I got up, took a quick shower and got ready. When I got downstairs, she had breakfast going and was pouring me a cup of coffee. "There's a bagel in the toaster if you want it, I just finished and am enjoying my coffee." So I got my bagel, sat down and put stuff in my coffee and started sipping it. It wasn't great because I still was not really used to coffee but it made me feel sophisticated.

I was chewing a bagel when I noticed her looking at me. "Stevie, honey, I know you're a virgin right now but have you experienced other things like oral pleasures?" My mouth was full so I couldn't yell at her and say, "what the hell are you talking about?" But I thought when she was pushing the whole virgin thing yesterday, my reaction meant it wouldn't come up again. But here she was with a total invasion of privacy. When I finally finished chewing, I said "why are we talking about this? You don't know me and what I do and stuff like that. I do lots of things with lots of people but, you know, it's private. I mean c'mon!"

I was steamed but also puzzled. I mean this woman was like a completely different person from one minute to the next. In the morning she was one way and at night another and I never knew what was coming my way. Plus I didn't really like talking too much about how many things I had done or not done. She reached over and smiled, though, not offended at all. She patted my hand and said, "It's okay honey. I don't want to embarrass you. I am just trying to help. I know that right now, as of today, you haven't had intercourse with a real woman yet and that's fine. It's a good thing actually. I just didn't know how far along you were. I'm sure a nice gentleman like you doesn't like to kiss and tell and you shouldn't. But sometimes a teacher likes to know her students. Remember you're my pupil, honey, and Mrs. Wentworth can help. It's okay though. A lot of boys haven't tasted a woman yet." She smiled in a very reassuring way and I didn't have to reply. I even stopped turning red.

Fortunately, she stood up and walked over to the sink so I didn't have to feel awkward. I stared after her thinking of what to say but instead found myself just staring at her ass pressing against another silk robe as she bent down at the sink. I took my dishes over and was trying to walk around when she backed up without seeing me and her tight silky butt made direct contact with my bulge. She said "oops" and giggled but managed to collide two more times as we tried to get our signals right.

Finally, she walked away and headed upstairs. She called down "I'll be ready to go in ten minutes." What? Go where? I didn't know what she meant. She was going out I guess. But I was wrong. It wasn't just her.

She came down, dressed like a very nice lawyer or something in a blue business suit which fitted her tightly and whose skirt was over her knee but not much over. She looked great. Not as good as the silk dress but I guess in the daytime you can't go all out. I was admiring her when she opened the door to the garage and said "I'll drive today. Let's go."

I was going to ask where but I thought she told me before and I forgot or something because she didn't say. She talked about other things. "Stevie, darling, I'm having the girls over for a late lunch or early dinner." I must have looked surprised because she said, "Oh I didn't mention it did I? Three of my closest friends are coming over for tea and light meal late this afternoon. I don't have anyone to help serve so I thought you could be the waiter. I'll train you of course but it will be fun. Like having a butler." I didn't have any response but I thought, what the hell it's better than mowing the lawn or doing something else. I said, "oh yeah, okay."

We pulled into the parking lot behind a store and got out. I followed her in. It was big store but sort of private. Mostly clothes but no prices or signs of cash registers or anything. A tall woman, even taller in heels, with pulled back dark hair came over and kissed Mrs. Wentworth on both cheeks. "Good morning, Mrs. Wentworth, we're so happy to see you again. Lisa has the items you ordered." The woman almost completely ignored me. Her assistant Lisa came over with three stacked boxes tied together. Lisa was younger than the owner ( at least I think she was the owner, she never talked to me so I wasn't sure). She was much shorter and wearing a short dress. She smiled and even winked at me. Mrs. Wentworth thanked her and said "I need a few things for Stephen here. We're having company and I think some shorts or something to hold everything would be a good idea." The owner said, "well, Lisa can help get one of the things we have in stock but we're shorthanded today Mrs. Wentworth so you'll have to help with the sizing." I had no idea what was going on or anything so I didn't even talk. I wasn't sure why I needed shorts but Mrs. Wentworth was doing this without having talked to me first.

Mrs. Wentworth looked uncomfortable and like she was going to protest but she didn't. Lisa smiled at me again and the owner took my shoulders and pushed me in front of a chair like the stools you try on shoes with. I went to sit but Lisa pushed Mrs. Wentworth into it instead of me and whispered "go ahead." The owner measured my waist and said "30" to Lisa and then waited while she looked at Mrs. Wentworth.

Mrs. Wentworth looked at me and said "Now, Stephen, dear, this is fine. It's just a measurement. It is all very clinical." The way she looked, it was like she was trying to reassure herself more than talking to me. Then she undid my belt and pulled my shorts to me ankles and looked at the owner nervously. I couldn't speak and had no idea what was happening. The owner looked at Mrs. Wentworth with just a hint of a smile and said "not good enough. They are fitted and we need a better sizing or they won't hold right. Take it out."

Mrs. Wentworth then pulled my underwear down and held my cock in her hand like she had before. I started to get hard right away remembering things. The owner whispered to me while looking at Mrs. Wentworth "let's see if you get larger, Stephen, while your teacher helps out. I need to find out if it's bigger than average or average or small when you're as big as you get. Now don't get him too excited Mrs. W. I don't want a mess just a size." It was humiliating and also very exciting. Mrs. Wentworth was stroking me and had her spare hand massaging my balls underneath which had me pretty close to exploding. She was very serious while she was doing it and staring very hard at my cock as it throbbed so close to her face except that she would look up at me every minute or so which made me very close to cumming right there. Then the owner handed a ruler to Mrs. Wentworth who had to let go of my balls and press the ruler against me for a few seconds and say "seven." The owner laughed, which made me feel bad, and called out "seven, Lisa." Then she smirked and said to Mrs. Wentworth "you're a natural at that." Then she said to me "according to research the average male penis is 5.5 - 6 inches erect so congratulations." She was a little condescending so I was embarrassed but happy to learn I was bigger than average.

Lisa came back with tight shorts that were almost like biking pants. Then she explained to Mrs. Wentworth not to me that "when he wears them he needs to hang it on the right side. See, it's looser there but just a little. It will hold him but not cut anything off." They handed them to me and I put them on. Tight everywhere but there was a little looseness for my now semi-hard cock to be tucked into. I didn't know what to say so I just got dressed. Lisa handed Mrs. Wentworth two more boxes "for the waiter." I took the two boxes and her three and we went to the car without paying anyone.

In the car, I tried to talk not knowing what to say but Mrs. Wentworth interrupted. "Stevie, sweetie-pie, you know how we talked about making sure little Stevie doesn't surprise people? This is going to help us. I go see Mrs. Jones for a lot of things. She has quite a nice collection so I knew she could fix this. I bet you feel much better with little Stevie in a proper spot, don't you?" With that, she reached over and patted my leg right there. The whole thing seemed weird so I just said "Yes, Mrs. Wentworth. Thank you for thinking of it."

She pulled in the driveway and said, "Back at our house. Now we need to get ready for our little lunch party." We went inside and she started right away showing me what to do. How to answer the door and act very official. How to show a lady into the dining room. How to serve plates and a pot of tea. We worked hard for a couple hours then she talked to me more about having the right attitude. 

While we talked, she had me follow her and we went into a laundry room where a bunch of clothes had been drying on air drying racks since before breakfast I think. The first thing I saw was my underwear that she had picked up earlier sitting there, now washed and dry. Almost everything else was her clothes. Actually mostly underwear. She picked up a few blouses and folded them while we talked. Then she told me to "be a dear and help me get these things folded. We don't want all our undies out when we have our guests at our house do we? I'm sure your mommy makes you clean up too when friends are coming over."

I started folding things but I wasn't sure where to start. The things hanging closest to me seemed to be only her panties and the other places had more underwear. I started folding her panties because I knew how to fold them anyway unlike some other kinds of underwear. It was interesting because they were all different colors but they were all silk or lace or things like that. I folded slow because I kept holding them too long. I tried to pay attention to what she was saying but when I was folding a pair of black lace-all-over panties I was distracted. It was the first time I was glad I had the new underwear because it made sure I wasn't just pointing up and out but was held together.

Mrs. Wentworth didn't seem to mind. She seemed really happy actually. I didn't ask if she only had sexy underwear but I did wonder. I mean my mom had some things but most of what I saw in the laundry anyway was cotton and regular. Maybe Mrs. Wentworth was just a lot sexier. I was pretty sure I remembered seeing other things in her room when I was snooping but maybe she washed them separately or something.

She put the laundry in a basket and told me to leave it on her bed. She then took out one of my boxes and put it on top and told me to wear my uniform and get ready quickly, guests would be here any minute. I went up and changed. I was a little nervous at first about what might be in the box but it was just a nice white shirt, tight even though I'm pretty skinny. And also a pair of black pants. You know, like a waiter. The pants were dressy but a little tight in the legs and much tighter on my ass than I wear anything. But that's the way uniforms are.

I heard a car in the driveway as I came down the stairs. Mrs. Wentworth looked out of the kitchen and I saw she had changed again. Gone was the cool sensual lawyer. Now she was wearing a flowery dress that came down halfway to her ankle and was buttoned up on top pretty high with maybe a little neck exposed. She looked less like a lawyer and more like a schoolteacher. It was very different, I thought, from the red satin tight dress that I dreamed of the first night I stayed over.

She went back in the kitchen and let me get the door as soon as the doorbell rang. I opened the door on three women. They all looked different but also all looked sort of like Mrs. Wentworth the way she was dressed now. They were surprised to see me, I think. I said "good afternoon, ladies. Mrs. Wentworth is expecting you. Would you care to follow me and I'll lead you to the dining room." I was so good I could have played a butler in a movie or something. I turned and walked and they followed, whispering to themselves.

I held the chair for the first one and let her sit before following and doing the same for each in turn. Then I carefully unfolded each napkin and placed it on their laps. I knew my actions perfectly just like I was shown. The ladies were almost speechless when Mrs. Wentworth breezed into the room. She walked around and kissed each on the cheek but they were all obviously old friends.

She nodded at me and said "please bring in lunch now, Stephen." That was my cue to serve the food. They giggled when I left and I heard one say, "Doris, did you buy him or are you just renting him for the day?" Then Mrs. Wentworth's voice, "Janine, please, he's a former student and the son of a friend." Then another voice saying, "I'd like to teach him a few things" followed by a nervous giggle and the person named Janine saying "can I have my lunch off his cute butt?" And Mrs. Wentworth more authoritatively, "stop it, he'll hear you and get the wrong idea. Stop it now."

I came back into the room with two platters with small sandwiches and cold salads to help themselves to. As I leaned and placed them in the center of the table, I felt a finger poke my ass like it was testing its firmness. The lady next to me was smiling. It turned out she was Janine. With her other hand she was gently touching the skin under her neck and above her cleavage. She wasn't low cut but lower than Mrs. Wentworth and had a teasing smile. I didn't say anything but I went quickly back to where I left a teapot and started pouring for everyone like I had been taught. Mrs. Wentworth was beaming with approval, Janine was looking hungry and directly at me. Another woman, a brunette, just looked nervous but happy. She was the one that giggled and was a little shorter and about fifty, dressed more businesslike but it didn't come off quite as sexy as Mrs. Wentworth had done it earlier.

The fourth twirled a string of pearls in her fingers as I poured. She had dark hair, a silk blouse and just stared at me without speaking. Janine on the other hand was talkative. When I poured for her last, she kept finding reasons to touch my arm or bump me. "Stephen, is it?" I nodded. "Stephen, I'm not your grandmother. I'm going to need more than a cup of tea. I notice the wine glass you set out for us. Are you pouring wine soon? Janine's day out needs more than tea." Her grin was like a predator surveying birds to eat. The other ladies all smiled or giggled. I guess Janine was known for being the bold one of their group. Mrs. Wentworth interrupted and said "You may serve the wine that's chilling in the fridge. The bottle on the left please." So I went to get it too.

In the few seconds I was gone, I could hear the giggler tell Janine "you're saucy today, Janine!" and Janine respond "and we just got started."

Everyone had wine except the giggler who said something about driving. I had started with Janine but by the time I got around she was almost empty and holding out for more. Mrs. Wentworth suggested I place the second bottle from the fridge on the side table and then join them. I sat with Janine on one side and the giggling woman on the other. They talked a little. I guess they all went to school together in the past but soon the quieter third woman named Anita asked about me. "Stephen, Doris tells us you're a student of hers." Mrs. Wentworth corrected "former student from my last year in the last school I taught at. Now he's just staying here while his mommy is away." I just looked at her and thought it was a weird way to say that. The giggler, Kim, asked in a half whisper if I had a girlfriend and giggled. I was trying to sound more sophisticated so I just said "not a specific one right now, you know how it is." At the same time, I felt someone's foot rubbing my leg and Mrs. Wentworth said "oh but he had a date with a pretty girl last night, didn't you dear?" I didn't know where she was going with this and wasn't sure how to respond. I mean the pretty girl was her and obviously she knew that. 

While I was deciding what to say, she quickled added, "Her name was Lana I think you said, wasn't it?" I nodded, feeling better about it. "Yes, Lana it was and she was very nice. I had a great time." With that, I smiled at Mrs. Wentworth who blushed even though no one else noticed or would have understood. Then I felt Janine's hand on my thigh when she leaned over and asked suggestively "did you get lucky, Stephen?" I didn't know how to respond when Mrs. Wentworth interrupted almost angrily "Of course not, Janine, stop that. Stephen isn't going to kiss and tell. He's a very sweet boy and knows better than that." Then, almost like she was changing the subject, she said, "Stephen can we start the other bottle?" The ladies had finished the first bottle of wine and I started pouring another while Janine said "you always were a prude, Doris." But she laughed and so did the others so it wasn't mean-spirited.




Staying with Mrs. Wentworth, Day 03



Janine rubbed my ass while I poured and reached over and squeezed my thigh again when I sat back down. Mrs. Wentworth looked annoyed at Janine and then got nervous when Anita asked if Lana and I were serious. I said, truthfully, "It was our first date, really so it's hard to say."

Mrs. Wentworth becamse more at ease and said to Anita "but they made a very cute couple so I hope they go out again." I smiled and thought about what that meant. 

The second bottle was soon gone even though only three of them were drinking it and Mrs. Wentworth sent me for a third which she had also put in the fridge. I was surprised because it seemed like a lot of wine but maybe she was expecting to drink that much. 

Janine didn't know I could hear everything when I was in the kitchen and I heard her ask Mrs. Wentworth the minute I left, "Doris, he's adorable. Can I take him upstairs and fuck him in your bed?" Kim giggled, Anita said "I don't think your husband would approve," and Mrs. Wentworth said "you're such a bitch, Janine." But then they all laughed. 

Of course it made me hard as a rock. I was contained but my bulge while not poking out was outlined by shorts and I realized the waiter pants weren't loose enough and so they showed it off instead of hiding it. I realized this when Kim was staring at my leg while I was serving Mrs. Wentworth and kept staring. Janine touched my ass again while I was serving and then told me she thought Kim wanted more tea. While I gave it to her, she didn't giggle but just stared. 

Mrs. Wentworth didn't seem to notice her one friend touching me and the other less bold one staring openly at my bulge. I sort of resented that the pants and shorts that Mrs. Wentworth decided on actually showed me off like that. But I guess she didn't think about that and she didn't seem to notice anyway. We stayed there talking for a while. Mrs. Wentworth and Janine had most of the third bottle. In fact, Mrs. Wentworth had a lot, Janine not quite as much and Anita very little. 

When they finally left it was getting dark. I held the door. Kim gave me a hug and Janine accidentally pushed her into me so my bulge pressed into her. She giggled and left. Anita also hugged me but more normally. Janine grabbed both of my ass cheeks, pulled me close and kissed me passionately before whispering "I wish I could take you home. I could teach you a lot more than your old teacher could." Then she walked past and slapped my ass, leaving me staring.

Mrs. Wentworth came back in after seeing them off and I followed her into the other room where she turned around and said "Stephen, my darling, you were just wonderful. I was so proud of you and so grateful!" And then she put both arms around me and hugged me very tight. I was so surprised and actually very happy to have helped that I didn't pay any attention to how I was positioned and where my bulge was. I was still pretty hard from Janine's good bye but Mrs. Wentworth didn't seem to notice it pressing into her. At least that's my guess because of how long the hug lasted. 

She pulled me next to her on the couch. Then said "wait a minute." And got up and brought back a new bottle of wine and two clean glasses and poured us each a glass. I don't usually have any but it made me feel pretty sophisticated to be sharing with her. She'd had a lot of the first three bottles so she was maybe a little bit drunk. Not stupid drunk like your friends in college might get but happy.

She stretched out her legs on the coffee table and then tuned and said "help me off with my heels you helpful man." I helped take both of them off. I think women's high heels are rel sexy so I kind of enjoyed it. Also I made her turn a little to get at them which is actually a pretty good angle if you were trying to peek up a very long skirt. I wasn't trying, at least not on purpose, but since I could see I thought I would at least look a little. Between seeing up her skirt and the fact that the first foot I had let out of the shoe was resting on the spot where my hardon and leg were held tight together, I couldn't help staying pretty hard.

Then I noticed she was talking. I heard "...so I don't usually wear this dress but with them I feel a need to keep up a look. After all, Janine is the one who...well it doesn't matter. Does the dress look OK, Stephen, or is it boring?" She stood up and stared at me.

I decided to be honest. "It looks fine. You look good, I mean. It is a little boring though but it isn't like you could wear that red dress you wore the other night here, right?" She playfully kicked me, still standing up. "I thought so. I knew you liked that dress. Oh well, help me change now." I must have looked funny because she said "it's OK, silly boy. I'm sure you help your mommy all the time dressing and changing and finding things. I just need that kind of help now. After all, you've been so very helpful to me and my friends today."

Then she turned around and held up her hair. I helped lower the zipper on her dress because that's what she wanted obviously. With her back to me, she wiggled her arms out and it fell first to her waist and then to the floor. She stepped out of it with her back to me still. She was wearing a white bra and her panties were visible through sheer pantyhose. She bent down to pick up the dress at her legs causing once again her ass to collide with me. I wasn't complaining though. Then she walked away and started going up the stairs and asked "are you coming?" I didn't know what was going on again but I followed. 

In her room, she started going through the closet and drawers like she was looking for something. I just stayed in the doorway and enjoyed the view. After a few minutes she bent down with her back to me and took down her pantyhose and took them off and laughed a little like we were sharing a joke. I was confused of course but maybe her being a little bit drunk explained everything.

But I wondered what was next. It wasn't that late and the dinner was more like a late lunch but it was after 7:00. It wasn't bedtime but she was looking at pajamas and nightgowns. She had me hold a few short satin nightgowns and robes while she looked. Then she took the black lace pair of panties I liked out of the laundry basket that was still on her bed and set them down. Turning to me, she looked up and down like she was evaluating me. "Hmmm, I think we'll watch a movie before bed or something so I should probably be careful. I think shorts and a top are the right thing. OK set the pile on the bed." I turned to go but she called out "Wait!"

She reached out and held both my hands and looked at me. "Darling, You look so much like a waiter and I just know that our guests appreciated your service and how perfect you looked." And then she hugged me again. This time her beautiful body just in her underwear pressing warm and tight against me. It's amazing I didn't explode. But I might have throbbed a little.

After a few seconds she looked concerned and pulled back and stared at my leg. Then she touched the lump in my pants. "Oh dear, he's been cooped up all day hidden away nice and proper so no one notices him. That's fine but I'm sure you shouldn't wear the shorts all day. Why don't you change too?" Then she patted my bulge and sent me along. It was weirdly erotic but at the same time in a manner that wasn't exactly seducing. It was a weird combination of motherly or something like that and also sort of bold because she touched what obviously hard even though not in a date kind of way.

I almost closed her door but she wagged her finger and said "open doors, always." 

It felt good to let everything hang out. I liked being held in but my cock and balls needed some breathing space. I just changed into some loose shorts and boxers and a not tight shirt and went downstairs. She had gone first and was sitting on the couch with two glasses of wine again and a tray with crackers and cheese. I noticed she was wearing green shorts and a matching long top that almost hid the shorts.

The whole thing seemed really very elegant and sophisticated and grown up. That was really nice. It was like she knew we were adults, equals sort of. And she was treating me just like it. I sat down where she patted a spot on the short couch. I liked the way she looked. The pajamas were sexy in a way even though they were shorts not a skirt and I couldn't look up them. Not that I spend my life trying to look up skirts. I'm not a total pervert all the time. But they were nice. Green satin was sexy and we were close on the couch like old friends.

I could kind of tell from the way her upper body was that she wasn't wearing a bra under her nightshirt because even though she was in good shape there was a sagging sometimes in her upper body that made it clear her breasts weren't held up. I did notice once when I got up and was about to sit down that her legs were stretched out on the coffee table and propped up. She was less careful I guess because she was wearing shorts so I could see the loose patch of satin that went between her legs not completely covering the layer underneath. That's how I could tell she had the black lace panties I had folded and looked at on underneath everything. The first time I noticed, it made me pretty hard. I managed to stay pretty hard for a long time because she kept doing things like reaching across and touching me on the leg when something was funny in the movie or turning and smiling and I would see almost a little cleavage. Or she would stand up to reach across the table for the wine bottle or other things and the way she bent made her gorgeous ass very noticeable and just a few inches from me. I wanted to reach out and grab it but of course I didn't.

Because the whole time was like a sort of long tease and I was just sitting there enjoying it, I didn't pay much attention to the movie. It was an old movie. Black and white with people I didn't know and I'm glad there wasn't a test because I wasn't watching the TV at all. At one point I completely stopped looking at the TV because I noticed something. Mrs. Wentworth's pajama shirt was long but it was a little tight in the chest. I could see bumps that told me she had hard nipples. Maybe because it was cold a little or I was hoping it was from just being with me or something like that.

A few minutes later, there was a commercial in the movie and she stood up and told me, "You know, my nightshirt is long enough that I don't have to have these shorts on. I think I'd be more comfortable without them." And she carefully removed them in a way I couldn't see anything. She was correct that when standing up her shirt covered her panties. But it wasn't by much and when she sat I saw a lot of leg because we weren't very far apart. Then she asked me to go get the remaining little bit of wine in the kitchen that was almost empty even though her glass was pretty full. When I came back, she still wasn't careful how she sat, forgetting she took her shorts off I guess, and I could see a lot. I tried hard not to stare but I saw all her panties and they were almost completely in the open. You have no idea how hard that made me. I almost wished I wasn't just wearing loose shorts with just boxers under them because I was really exposed.

I sat back down and continued staring at Mrs. Wentworth's breasts while she watched the TV. I couldn't exactly cover up myself but as long as she looked at the TV, I was OK. She stood up again and bent over causing her shirt to rise in back and expose the panties. They had a black lace back almost like netting. They looked better tightly covering her ass than when I folded them. If this was a movie I'd have jacked off and cum in about 10 seconds. But I tried to stay cool. She sat down again but closer. Our legs almost touched and she smiled at me and drank more wine. I'd had about one full glass but she had had over the last five hours a whole bunch more. 

She looked directly at the pressing bulge in my pants and sighed and patted it. "Oh, my sweet Stephen, I feel so bad. The whole day must have been hard for you with that awful Janine just teasing you and you're still under pressure from it now! I feel terrible. You need some room. Now don't worry, sweetheart. Mrs. Wentworth understands how men and their parts work. Stand up and take off your shorts so you aren't pressed so much. Don't be shy. We're alone in our house and it's perfectly fine and natural. Right now, please."

What could I say? I sort of agreed. And I couldn't protest so I stood up and did it while she leaned forward a little like she was watching and almost staring. When I dropped the shorts, I only had on boxers and my cock was poking straight out. Dropping the shorts almost made it bounce. Fortunately, it was away from the fly opening so I didn't spring out. Mrs. Wentworth reached a finger out and poked the tip which was hidden but made a wet spot with pre-cum. "Oh, look. Poor thing is actually leaking. I'm glad we let him have some room." Then she leaned back and watched the movie.

Talk about mixed signals. Oh well, I sat back down, more comfortable even though I was sitting next to this older woman with a practically throbbing hardon almost visible. I was sure it would calm down with fewer peeks at her and a slower evening. It started to go down a lot pretty soon and she never looked directly at it. But when she stood again and bent, the tease of her panties was too much. It was worse when she twisted as she sat. Her shirt rose more than she probably thought and it was twisted so it was tight enough on her breast and facing me that I almost had to stare. And then she leaned and put her head against me like she was tired. I had to close my eyes for a second not to explode.

She was sort of whispering with her head against my neck, "it's terrible what they did to you and made you so frustrated all day long. I'm glad I was a perfect lady at dinner and didn't contribute to that!" I couldn't tell her that it wasn't just her friend at dinner but it more her and her awesome look all day that did this so I didn't say anything.

Then she looked down and poked my hard on and giggled. She actually giggled. It was weird. "Hmmm. It isn't healthy is it, darling? It's not good for a virile, handsome, fit young man to be so frustrated and backed up. And it was my friends so it's sort of my fault." I just kept quiet because her hand went down and reached in and pulled me out of my shorts. It was all happening in slow motion like a dream. I mean her hand actually had just pulled my throbbing cock out of my shorts. Then her head moved down and suddenly her tongue licked the tip and then I was in her mouth. I was almost shocked.

I looked down and only saw the back of her head but I could feel her warm and wet mouth all around it until I felt her head pop off with a smacking noise. "Yes," she whispered very roughly like she was suddenly hoarse, "the only proper thing to do is release the pressure." It was like she was talking to herself though.

I'd love to say I lasted for like a half an hour. But I didn't. This was the first time a woman, a real woman, had even thought about sucking on me. It was amazing and I had been so close to cumming off and on all day. I didn't know at the time if she was good or bad because it was my first blowjob ever but she was actually really good. It was less than five minutes before I was tense and started to spurt. Her hand encouraged it all out even when she popped off. When I was done, I sat there catching my breath but she stayed there with her head down. 

After a minute or two, I heard her say very quietly, "I have to go to bed." The she stood up and turned around and said "good night dear, thank you for all your help today." It was as if nothing had happened except she had a few spots on her nightshirt and something on her chin. I didn't get a chance to say anything, she just hurried away and up to bed.

After a few minutes, I got up and started cleaning up things before going up. I was still in shock that it happened. Mrs. Wentworth had just given me a blowjob. I had no idea what I was going to say to her on the way to bed or in the morning. 

It was about twenty minutes later when I went up. I went to her room to say good night but she was under her covers and obviously asleep so I just looked for a minute and finally went on to my room. For the first time there, I didn't masturbate before going to sleep. I just tried to think of what to say in the morning and how different everything was going to be tomorrow.



Mrs. Wentworth and a Useful Lesson



This story comes immediately after "Mrs. Wentworth and a Night the Opera" which followed the three chapters of the "Staying with Mrs. Wentworth" series. I really appreciate all the comments people made both publicly and privately on those stories. I benefit a lot from the comments and thoughts that help me understand how some characters are feeling (especially the female ones) and some of the details like fashion and things I have less experience with. And I try to always reply to feedback. I hope you enjoy reading as much I'm enjoying writing. 

*

The morning after the opera, I woke up in the hotel next to Mrs. Wentworth (see Mrs. Wentworth and a Day at the Opera). This was only the fifth day I'd been with her since the start but it already seemed like a long time. When my mom had first made me go stay with Mrs. Wentworth, I was angry (see "Staying with Mrs. Wentworth"). After all, I'm an adult. I was 19 and grown up but my mom was making me stay with an old teacher of mine. Actually Mrs. Wentworth wasn't really super old, she just had seemed that way to me when I was in fifth grade so many years ago. But still, I was an adult and just because I still lived with my mom, she thought she could make me stay somewhere when she went on a business trip. I had to admit though, I was enjoying it now and really liked Mrs. Wentworth. It wasn't just a crush, I didn't think. I felt like I really cared about her and liked being with her.

The night at the opera was a lot of fun even though it was opera. I felt like she was treating me mostly like a grown up. And now I was next to her. It was sort of an accident. After all, it was a coincidence she had thought to pack an overnight bag and put it in the car. And we were lucky she thought to rent a room in the hotel just in case we had a few drinks. And even though she was a little drunk, she told me she had asked for two beds. It was a mistake the hotel gave us just one. I was lucky she had packed new silk pajamas for me. It was thoughtful. Still, all those coincidences led to me sleeping next to her even if it was mostly innocent.

I had been surprised how fast she fell asleep and how tight she held my arm in her sleep. I felt guilty about playing with her nipple. My fingers ended up against that part of her nightgown by accident of her sleep movements. And when I came in my new pajamas while pressed against her I would have cleaned up if her sleep grip wasn't holding me there.

Anyway, when I woke up it was from feeling the covers pulled back and watching her slink out of bed, trying not to wake me up. I enjoyed the view of her getting up and didn't say a word. But when she returned from the bathroom, I pretended to be waking up. She didn't notice until she had climbed back in bed and squished next to me.

"Good morning sleepyhead," She said. Did my sweet Stevie have a good night's sleep in his darling new jammies?" She kept the covers down and looked at me. I don't think she noticed the staining which had dried but she must have noticed my morning hardness. I wake up most morning with an erection. And I knew my morning wood was making a tent.

I didn't want to call attention if she didn't and I also felt weird, like usual, when she said things like jammies. I'm a grown up and she sometimes treated me like a kid. So all I did was smile and say "Good Morning."

she reached over and started rubbing my pajama shirt and said, "I just love the way silk feels against skin. These are so soft of slippery and wonderful feeling, don't you agree? Don't you love the way this feels?" She kept rubbing my shirt softly on shoulders and chest and even stomach.

This was killing me, I loved it. I could feel my cock twitch in my pajamas and I wanted to hide it but I didn't want to call attention to it. She just lay there rubbing my pajamas shirt and smiling without realizing what she was causing I guess. All I could say was "Yes, I agree. It feels great Mrs. Wentworth." She didn't need to know what I meant.

Then she stopped and looked past me at the night stand on the other side. "Wait," She said. "Let me grab the program." She meant the program from the opera the night before. She moved to reach over me or crawl over me. I was pushed onto my back and she was on top of me leaning over. It was awkward. Her breasts were hanging partly in my face really but that wasn't the worst of it. Or best of it. Because she was stretching, trying to grab the program and having trouble, her body was sort of squishing my hardon. Her hips pushed on it and her reaching and stretching made her sort of wiggle around on me. I groaned silently and tried to pretend nothing was happening but really I wanted to just grab her and do something right there. I think if I had been more experienced in the sex department I might have.

I concentrated and tried hard not to explode and embarrass myself. Finally she found it and slid slowly off me. She showed me the program and I didn't hear what she said because I was staring at her nipples making bulges in her nightgown and trying not to be obvious.

Finally, she said something about a shower and she got out of bed and went to take a quick shower. Eventually, we both had showers. Mine was a little cold to calm me down. But we got dressed. She had packed clothes for me for today too. Not a suit but not jeans either. My pants were dressier and it seemed kind of adult. But by the time I got ready, she had packed everything and we headed downstairs. In the lobby she had me give the suitcase to a worker there who took it to the car and we went to have breakfast. While we ate, she said we were going to spend the day together in the city and have a nice time together. I was happy knowing that I would be happy just being with her. It was different but I really didn't care at all what we did. I just liked spending time with her.

After breakfast, we were walking to the car but she wanted to cross back over to the opera house first. Obviously I came too. It wasn't very early because we hadn't made it out of bed and down to breakfast very early. But it was around 11 in the morning so the information window was open. While she talked to them, I looked around. I didn't know what she lost but I just wanted to look at the impressive building. 

Anyway, she came back with a big smile and put her arm in mine and walked around with me. In fact, she pushed us out of the main hall and into the area where the boxes were. I still think the boxes were one of the coolest parts of the whole thing. We went into the one we sat in before. We stood there looking at the empty theater and she said, "here it is sweetheart: our box, our special place to watch the opera and all the people." 

I have to admit I liked it. Here I was with this person I was getting to know better all the time and feel happier to be with all the time. And we were in this luxury kind of place, a private opera box. She had her arm in mine and was squeezing me close to her and I loved it. She really did something to my insides in a way I would not have predicted when I first came over to her house and was annoyed at having to stay with her.

I also liked when she called me sweetheart instead of some other things that were more demeaning. Sometimes she seemed to treat me like I was less mature than her even though I was absolutely an adult, just a younger adult than she was. But sometimes women talk that way about jammies for example. Sometimes though, we had a much more mature relationship. After all, a couple very sexual things had happened between us. The circumstances were always a little odd but they were still very erotic. Sweetheart was one of the words that could be taken different ways but I took it like a word she might say on a date with a guy she liked. 

It may seem weird but feeling her pressing close to me and moving her arm around my waist as we stared at the empty theater made me a little bit horny. Actually, something about her always seemed to make me horny. It didn't hurt that her hand wasn't exactly on my waist but had slipped down a little and she was using my back pocket for her fingers. It sounds perfectly innocent and I'm sure it was for her but her fingers in my pocket right there actually made me a little bit hard. It didn't last because some security guard poked his head in and told us they were closed and we shouldn't be there.

That was okay, though. We walked away and back out of the building. She had her arm in mine all the way to the car which was waiting for us. I wasn't sure what was next but we drove a few miles away and went shopping. Obviously I didn't need anything but Mrs. Wentworth was looking in a lot of different shops. She didn't buy anything at first. We walked arm in arm like she needed support but I think she was just keeping me close. 

We ended up in a shop that sold a lot of dresses after visiting five or six others. A very nice woman helped her out and showed her dresses while I waited. After what seemed like forever, she looked at me and said "I don't buy a thing unless Stephen approves of it. Honey, will you tell which of these three you like best? It's what I'm going to wear tomorrow night." Of course I had no idea what tomorrow night was but I went along and thought I'd figure it out.

The saleslady smiled and everyone seemed happy. The two of them went into a dressing area and finally came back out with Mrs. Wentworth wearing a long dress. It was some kind of plaid and had a high neck and was kind of boring. They both looked at me and I just shrugged and said "it's nice I guess." They went back.

Then they came out with a very different dress. It was a lot shorter and pink and very tight. It may have even been too tight. Mrs. Wentworth said "I know you can see my underwear lines and tell what I'm wearing underneath but ignore that and pretend I'm not wearing anything under it." I didn't say anything because I was imagining what she just said about wearing nothing under it. 

She frowned and said "I can tell he doesn't like it." And then she turned and went back and the other lady followed. 

They came out a third time and I liked it much better. She could tell by my smile but I said, "wow! That's nice."

She smiled and so did the other lady. "I knew he'd like it better," Mrs. Wentworth said. It was a nice blue dress. Not slutty or anything but it had a lower neck and sort of hung down looser. The skirt was not tight at all. It was actually longer and real loose but it just seemed better on her. 

While the other lady went to get some shoes or something, Mrs. Wentworth bent over to the chair I was sitting in and kissed me on the cheek. "I'm glad you like what you see," she said. I did like what I saw because when she bent down, the dress hung loose and I could see down her neckline and see her whole bra practically. It really did look good on her but that definitely sealed the deal for me. 

She went back and changed back to her other clothes and we left after paying. It was nice although she made me carry the box they put her dress in and then another box from a shoe store we went to next and then a smaller box with cookies and then a fourth box with a purse in it. I felt like a servant at that point.

We had shopped for hours and skipped lunch. But I really didn't mind. I had fun. But now my hands were very fell and so we went back to the car. The car was in a parking garage because street parking is almost impossible in the city. We loaded the trunk with the boxes and then I held the door so she could get in. She likes it a lot when I hold the door. But I think she brushed against something and she asked me to help brush her off.

I didn't see much but I brushed some lint or something off the back of the blouse she was wearing. I was gentle of course but when you brush you can feel everything. I kind of liked brushing and feeling her bra through her blouse. It was the back of it but it was fun. 

She said, "No, Stephen," and I worried I was too forward. But then she added "the blouse isn't so bad. I need you to do the skirt, dear. Be a good boy and help me out." When she said it, she put her hands on the side of the car and bent so her butt side stuck out and the skirt was tight against it.

I wanted to be helpful to Mrs. Wentworth and I didn't mind the opportunity to place my hand on her butt too. So I brushed a little slowly. She didn't notice or she didn't mind. I didn't want to go too long so I stopped pretty soon. But then she told me, "please be very thorough. Make sure you get everything." Then she bent a little more to give me a better angle I guess. I liked that. He skirt got tight from stretching and I could see and feel her panty lines while I brushed her off. It was pretty sexy and I got pretty hard. I think I brushed a little slow and cupped my hand a little so it was a lot like feeling her. Finally I stopped. I loved doing it but I didn't want to push my luck or make her think I was taking advantage of her.

When I stopped she almost seemed disappointed. "Oh, did you finish? Thank you, dear Stephen."

Then we got in the car and I started driving. She told me where to go and I realized we were done with the city. On the way back to where we lived, I mean where Mrs. Wentworth's house was, she directed me a small shop in a quiet shopping plaza. When we parked, I went in with her. It was a little embarrassing because it was a store for ladies underwear and lingerie. I was allowed in because I was with her and no one seemed to mind but Mrs. Wentworth was looking for something special. The sales helpers were all well dressed women. I guess I didn't know what to expect. It's not like they'd all just be wearing underwear or nightgowns. But the mannequins were all very sexy. I even found myself staring at one and thinking how cool it would be to take the mannequin home and do whatever I wanted.

But when I stopped daydreaming, I found an older lady talking to me. "Please sir, if you would follow this way while Madame tries on some clothing." I followed her and realized I wasn't paying attention and hadn't seen Mrs. Wentworth wander into a helping area. The older lady found me a chair and placed it right near the door to the dressing room.

I tried not to look but then couldn't help it. The room had a curtain and it was open a crack so I couldn't help look through. I kept leaning forward to tie my shoe because when I was bent forward like that I could subtly look through the curtain's narrow opening. Unfortunately, Mrs. Wentworth was in another room inside that area. The sales helper was talking to her and holding clothes and helping her decide. Then, suddenly, I heard her say "oh that's a good one to keep too. Come look at it in this mirror by me." And then Mrs. Wentworth came out of the inner room and into the outer area. My eyes almost popped out. She was wearing the greatest underwear. It was black with white dots but everything matched and it included panties and a bra and stockings and even a garter belt. 

I only got a short look because the older lady came back right then and saw me bent down and asked, "is everything okay?" I sat up real fast and sat back in my chair and tried to act natural and just be relaxed. She smiled and almost laughed. I think maybe I was busted. But she sat down and asked me if I liked to go shopping. "I don't think I've seen you in my store before. Is this your first time or is she buying something for you?"

I got red a little from being angry but also a little embarrassed. "No, of course it isn't for me. I mean I never come here at least I didn't before and I'm just helping."

I'm sure I was a little hyper but it was good that Mrs. Wentworth came out right at that second. She hadn't gotten dressed again and didn't notice me when she went by to bend down and look at some shoes on the next shelf over. She stayed bent for a while so I really had no choice but to have a very close up view of her gorgeous full butt in flimsy, very sheer, but with a full back piece silk panties. 

She slipped the shoes on and admired her feet in a low mirror before walking back into the dressing area. She noticed me just at the end and added as an afterthought, "oh hi there sweetie-pie, almost done and we can pack up my purchases and go." The she disappeared.

The older lady gave a soft laugh, kissed me on my cheek, and said "see you later, sweetie-pie." Then she left giggling.

Minutes later, Mrs. Wentworth came out and walked quickly past so I had to get up to follow her and her helper. We went up to the front and the older lady checked us out, taking the money from Mrs. Wentworth, handing me the bags, and winking at me. To Mrs. Wentworth she just said, "I hope we get to see a lot more of you in the future. We want to thank you for your business and look forward to fulfilling all your needs." Then we left.

I put everything in the trunk. We'd bought a lot that day. As I started driving away, Mrs. Wentworth was returning a phone call. I didn't know who she was calling or why then I realized we hadn't talked to my mom. I mean I hadn't. I didn't want to really and fortunately that isn't who she was calling. I heard her say, "Hi Janine. Of course I didn't forget. We aren't late are we? Why, I'm with Stephen of course. Now, stop that. You really are very wicked. He's very helpful. No. No. Stop it. I know you're kidding. Yes, we were just about to head your way. Great. We'll see you soon."

She hung up and frowned. "Darling, I have bad news. My dear friend Janine had invited me over for tea and I can't believe I forgot. I'm sure you remember her from our tea party. I'm sorry but we have to go. I hope you don't mind."

I did remember Janine (see Staying with Mrs. Wentworth, Day Three) but I didn't say what I remembered just "yes of course. I don't mind at all. I'm more than happy to go anywhere with you." It was the right thing to say because she smiled real big and kissed me even though I was driving.

When we got to Janine's, she had a nice house but not as big as Mrs. Wentworth's. It was nice though and she let us in. She was alone but told us her husband was at work but Kim was going to stop by in a little while but no one else. Actually, she looked real good. Her dress was lower cut than last time and I could see the line of her cleavage. I liked Mrs. Wentworth a lot more but Janine was distracting. She hugged Mrs. Wentworth and winked at me over her shoulder while she was doing it. Then she grabbed me and said "come here you cute thing." Then she hugged me and grabbed both cheeks of my butt and pulled our hips tightly together.

Mrs. Wentworth looks disapproving, like the teacher she used to be and said, "stop that Janine. You'll set a bad example."

We separated and everyone went into the kitchen with Janine pinching my butt as I walked. We walked through the kitchen where Janine had been cooking and drinking too if the half empty bottle meant anything. We went through to the dining room. I guess these ladies had tea together a lot. While we sat down, Janine rushed off to the door because Kim had apparently arrived. While she was gone, Mrs. Wentworth whispered to me to be careful because Janine was unpredictable and could be "mischievous when she's been drinking. I don't want her to give you the wrong idea."

I was about to sit down when Janine came back with Kim behind her. "Kimmie, you remember the delicious Stephen don't you? Give him a hug." Then she pushed the shy Kim into me and we hugged each other tighter than we might have because Janine was pushing Kim into me.

We sat down and Mrs. Wentworth helped Janine pour the water for tea. The good news is there were little cakes on the table and cookies. In addition to tea, Janine gave each of them a martini. I noticed Mrs. Wentworth drank hers pretty quickly. Janine does that to her I think. I didn't get a martini but I did have some of the tea. I also was the first one to help myself to the cookies. I guess no one wanted to be first but I didn't mind.




Mrs. Wentworth and a Useful Lesson



Janine had arranged things so I was right next to her around a small circle table. She reached next to me and put her hand on my knee. Then she said loudly, "He seems very hungry. I hope he doesn't just eat cookies." Mrs. Wentworth didn't react but she glared at her again.

Janie said, "I'm glad everyone came. I hate to just drink alone. Tea, I mean. Now that everyone is here we can have martinis. Help yourself to the pitcher on the table. No one wants just one do they? Now, dear sweet Doris, please tell us all about how you've been corrupting your delicious young man today." I sort of liked being called delicious and she looked at me almost like I was a steak she was going to eat.

On the other hand, Mrs. Wentworth took things differently. She did help herself to another martini. But she was getting more annoyed with Janine. Or maybe embarrassed. "Janine, please! We're all happy to be here but you give Stephen such a bad idea of how respectable ladies behave. We've done nothing of the kind. I expanded Stephen's cultural education at the opera last night and he accompanied me on some shopping today. Then we joined the two of you for tea. It's all very respectable."

Janine rolled her eyes. "Doris, could you be more boring? Opera and shopping aren't exactly the wild life kids are hoping for. You could have at least stayed out all night at downtown bars or slept in the park. Did you at least buy something fun? I'm surprised our young stud didn't fall asleep last night or today." Then she reached over again and squeezed with a hand in my lap and on my thigh.

I stayed calm and had another cookie but Mrs. Wentworth got defensive. "Stayed out all night indeed! We went home and got a good night's sleep." 

She was lying. Not that it mattered but she tried not to look at me before she continued. "Then this morning we went to a few stores and bought a few things I needed and some groceries." I guess she didn't want to talk about where we went which was okay with me but I didn't know why she didn't want to say.

Janine turned to me. "Stephen, I'm sorry. Opera wouldn't be on my list. I'd take you to a motel and spend the afternoon giving you a completely different education. In fact my husband won't be home for an hour. We could ditch these two and go upstairs so I can give you some private lessons unless you think we should have Kimmie join us for a threesome?" She grinned.

I knew she was teasing but Kimmie just giggled while Mrs. Wentworth yelled at her. "Janine! Honestly, stop it. You're just trying to shock us now." They were sort of mad at each other but not completely. It seemed like it was a kind of teasing they were used to. And they soon started talking about something else as if nothing had happened. But I was daydreaming about what they said and trying not to look like I was picturing the whole thing in my head. 

They kept talking and I stared at each woman one after another. It was fun being there with them even though this was kind of boring. Janine was very flirty and it annoyed Mrs. Wentworth. I think she noticed each time Janine reached over and patted my leg. She did it a lot. I think Janine was teasing me on purpose. And each time she talked to me, which was only a few times, she turned in my direction and did it. The last two times she actually reached over and grabbed the bulge in my pants and squeezed. Mrs. Wentworth glared each time and on the last time actually hissed angrily at her. I guess that stopped it.

Janine was drunk I think. She'd had three martinis which is a lot and I was sure she'd had a drink before we got there. Mrs. Wentworth had three too but she didn't have anything first and she was still a little on the drunk side. 

Janine's dress was the kind that wraps around and ties. It makes great cleavage but also when you sit you can play with and expose lots of leg like Janine did. In fact, she exposed a lot more. She moved a leg outside the chair and pushed the bottom of the dress up pretty high. I know she did it on purpose because she looked at me and smiled and looked down so I could see she was showing me her panties. They were very blue and had lots of lace trim. I had to look.

Mrs. Wentworth was real mad and Janine seemed to be trying to make her madder. Suddenly she grinned and said, "Doris, you said something about shopping. I think I bought more fun things than you did. The new undies I bought are probably better than whatever you are wearing. Let me show you." Then she stood up and untied her dress and unwrapped herself. The bra matched her panties and she was definitely right about looking good. Then she walked over and showed herself to me but talked to Mrs. Wentworth even though she was looking at me. "Doris, maybe we should all open our dresses and see whose underwear your delicious pupil likes best?" Then she leaned in and her breasts were six inches from my head. "Does Stevie want to judge all his lady friends? Hmmmm?"

I think I was smart to be quiet. Mrs. Wentworth was up and over and pushed Janine back. She seemed pretty mad. "Sit down you drunken bitch and stop it. You're just trying to make me angry and it won't work."

Then Janine, who really was trying to make her mad and had succeeded, just giggled and said, "Doris, my love, I don't want you to be mad. I just want Stephen on his knees to eat me. But if you want to lick instead, I don't mind." And then she just started laughing.

Mrs. Wentworth didn't react how I thought. That didn't make her mad anymore. She just turned and said "We should leave, Stephen. I think Janine needs some alone time. Why don't you thank Janine for the tea and we'll be on our way." 

I thought would create another fight but it didn't. We just got up and I said thank you and Mrs. Wentworth said "Thank you Janine. We'll have to do this again soon. Oh, why don't we give Kim a ride, she's had as much as I did." 

With that, we all moved to the door and it was like nothing had happened. Janine had completely removed her dress but hugged both Mrs. Wentworth and Kim like friends. Then she grabbed me and kissed me very hard rubbing her half naked body against me. She let go and whispered in my ear "next time we fuck." Then she smiled and we all left.

We got in the car with me driving. The others had had a few too many. That's why we were driving Kim home. She actually lived nearby and we dropped her at her house. Mrs. Wentworth walked her to her door and they talked for about a minute before she came back. Then Mrs. Wentworth got in and we headed home. I waited a few minutes and nothing was said so I jumped in. "So, what was that all about? It was kind of a weird afternoon, huh?"

Mrs. Wentworth sighed and then looked at me while she thought about what to say. "Stephen, you're such a good sport to put up with all of us. Janine must have been shocking to you." 

I knew I should have been shocked I guess but I wasn't really. In fact, it kind of turned me on but I knew enough not to say that.

"Mrs. Wentworth, I wasn't shocked at all. I mean I have friends who are a lot like that so no big deal. I just wasn't sure how everything went and how we knew when to leave and stuff like that."

Mrs. Wentworth smiled and said "you have friends like Janine? A lot of the girls you know tease you, grab your crotch, invite you to get on your knees and take their dresses off? Maybe you lead a more exciting life than I think Stevie dear."

I knew she was kidding but I couldn't help being embarrassed. "No, I didn't mean that. I don't know a lot of girls who are into anything really. But, you know, some people do stuff and talk certain ways. I just mean I was cool with it."

She reached over and patted me on the knee and laughed a little. "Yes, of course. Actually, sweetie, Janine has always been a little wild and likes to get crazy sometimes. She also likes to drink and that makes her crazier. I could tell you stories about when she and Kim and I were all younger. Never mind though. I was a little worried that she was might have been a little bit serious about trying to seduce you. But most of it was just to try to make me angry. She has always liked to tease me for fun. There was a time in college when, well never mind. I knew it was time to go." 

Then Mrs. Wentworth got less serious and playfully slapped my arm. "Not that you seemed to complain when one of my best friends was almost naked and throwing herself at you. Maybe that's what you like, dear. You like to have all your women strip to their underwear and drape themselves on you." She was laughing but made it sound like a crazy movie script.

I just laughed too and said "no, no. I don't like that. I mean that isn't what I was thinking. I mean it hasn't happened before. She's your friend and I was being polite." She laughed and smiled at me.

By then we were home and she let me hold the door open for her before she got out. It was a little like I was her driver and a little like I was her date. But while she opened the front door, I got most of the bags and the little suitcase from the trunk and brought them in. She took two of the bags and asked me to take the others up to her room.

I took everything up. Since she was downstairs and I had a few seconds, I took a minute or two and looked at the silky bed sheets and then at her dresser. I looked inside it but then decided to just head back down.

She was on the couch and had opened a bottle of wine. "Come to me sweetie. We're going to have a lazy evening and drink too much wine. There's a tray of little appetizers I'm reheating in the oven just to give us something to bite. Now come here."

I went and sat by her. It was awesome. She and I drinking wine, relaxing on the couch and just hanging out with each other like there wasn't anyone else she wanted to be with. Ten minutes later the oven bell went off and I got up and put the appetizers on a plate. There were a lot and I brought them over. 

But as I was setting them down, she asked one of her questions again. "Stevie, darling, I am wondering something. You can tell me honestly, Stevie. Janie said you should eat her and I wondered if you had ever done that before? Now before you fly off the handle, this is just private talk between friends. I know a lot of men don't and I think you probably never have, have you?"

I just stared at her for a really long time. Sometimes, she seemed crazy. Did she want to embarrass me? I mean it was really personal and not the thing you ask. I guess she was a little drunk. Maybe that was it. Of course I hadn't. I wanted to but I didn't ever have a girlfriend where that was possible. I just wasn't experienced so I admitted it. "Yeah, well I haven't exactly done that. I mean I don't really remember every date I ever had but I think I probably didn't get around to that."

She giggled. "You'd remember my cutie. I guess a man never really does that right away. He needs some help." 

But then she was looking thoughtful and sort of far away in thought. "A man learns when someone shows him. A teacher is what a man needs. He needs someone who, for his own good, shows him what to do. A good teacher does that." She didn't seem like she was talking to me. It was more like she was just talking and I happened to be there. She wasn't even looking at me.

I didn't want to keep talking about not being experienced so I dropped it. She kept drinking wine and I was drinking the glass she gave me and eating a lot of the things she made. It wasn't dinner but I wasn't super hungry anyway.

She pulled off both her shoes and stretched out her legs which I almost had to stare at. I liked her legs a lot. She could probably figure that out too. But pretty quickly she got up and said "be right back." I heard her go upstairs and knew she would change. 

She came back down wearing a nice silk robe but it was long. I liked her short ones better but I guess the leg show was over. She sat down and started flipping TV channels. Finally she stopped and shut the TV off. 

She took a very big drink of wine and then turned to me. "Stevie, I know we're friends now and your mommy told you to help me when I need it. You've been a wonderful helper but I can't forget that I was and I still am your teacher. And I'm also really embarrassed about what happened today with Janine. But I have a solution. Stevie, sweetheart, will you trust me?"

She looked so serious and so concerned, I didn't know what to say. But of course I trusted her. "Mrs. Wentworth, of course I trust you a lot and I know that I have learned a lot just talking to you so whatever you say is okay with me."

That made her happy, I guess. She then turned on the couch and whispered. I don't know why she was whispering. No one was watching but maybe she was nervous. She put her feet up and bent her knees and parted her legs. I could see a pair of white silk panties covering her as her legs got wider. All I could do was look at them in awe. She didn't mind.

"Stevie, darling, we're going to begin a lesson. This is just a lesson. It's perfectly clinical, that's all. Intimacy like this would often happen when your partner was not clothed but I'll leave these very thin, sheer panties on so you know we're just studying and learning. Now I want you to bend over and gently kiss my thigh near the panties leg hole. This is how a man starts to orally please his partner."

I didn't believe this was happening and I didn't speak because I was afraid I would mess things up. I just followed.

I leaned in and kissed and licked gently all the way to the edge of her panties. I liked the way she smelled. Her smell was very strong and like a unique kind of perfume. 

By this point she had both hands on my hand caressing the back of my head but one was gently pulling me up further. "Now place small kisses up and down the front of the panties. Yessss, just like that. Now stop up here and spend a few minutes kissing." Her panties were soft and a little wet but just a little.

Her legs were a little wider and her speaking voice was breathier, like she was having a little trouble with her breath. "Stevie, that's a woman's clitoris. Sometimes it's easier to notice a woman's clitoris when I'm excited. It's very sensitive even through my panties so be gentle but your partner will like the attention you pay here." 

I was trying to follow her instructions carefully but it also made sense just to kiss and lick gently and make sure she was responding. I knew she was teaching me but I thought that getting a real response would happen if I was doing it right.

She wasn't talking as much as when we started and her hands on my head were holding it tight, almost pulling my hair. Her body didn't stay still which made it harder but I think it was because she was having fun too. Sometimes she would talk between gritted teeth: "yes, Stephen, OH, right, yes that's what I meant." Other times, she wasn't very specific: "yes, oh yes, thats a good idea." 

She had loosened her grip and I lifted my head to just look a bit and her back was arched backward which made it hard for her to see what I was doing. Also her eyes were closed but I think she could feel it. 

Her panties were even wetter which I could feel on my chin. It was then that I figured out that arousal makes a woman sometimes get wet. Mrs. Wentworth wasn't really speaking anymore, just making noises and moving around. 

Suddenly, I felt her body shaking and her legs twitching and heard a muffled sound from her head but I didn't want to stop tasting her. It wasn't long after that though that she pulled on my head and pulled me off her and slid me up so I wasn't doing it anymore.

She held my head and seemed to be catching her breath. I was pretty sure she had an orgasm even though she was just teaching me. Actually her orgasm made me feel better than almost any part of it. I got a lot of pleasure inside just from knowing that I had caused an orgasm in her no matter why it happened.

After a while, she moved back to her old position and sat back up on the couch. I figured she would have to go upstairs and change again but she didn't leave. 

A few minutes later, she didn't look at me became all teacher-voiced again and said, "anyway, so you can see that if you happen to be with a woman sometimes and she has some interest in something like that you'll know what to do. You can see why it was very naughty of Janine to suggest something like that today. I don't know what she was thinking."

I wasn't sure what would happen next so I just said, "Yes, it was very surprising and not right of her to ask that."

I wanted to be grateful but wasn't sure what to say exactly so I added, "Um, thank you for the lesson for me though." I wasn't sure what to say next because I wanted her to know how much I enjoyed doing it for her but not if she would think that was weird.

She finally turned to me and smiled and said "you're just the sweetest young man, aren't you?" And then she leaned over and kissed me. It was nice. Not too quick either which was sort of funny because I bet my mouth kind of tasted different because of where it had just been. 

I stayed pretty hard the rest of the night but all we did was talk about other stuff, finish the wine, and the appetizers. She kissed me goodnight, got up, walked into the laundry room for a second and then to bed. "Night night sweetie."

It wasn't late but I was actually pretty tired. I walked by the laundry room too about fifteen minutes later. I went in and found she had left the panties she was just wearing on the top of a hamper in there. I could tell because it was open and they sort of hung on the edge. I couldn;t help myself and grabbed them. They were still wet, obviously. I wasn't about to jack off in the laundry room so I slipped them in my pocket and went upstairs. 

Mrs. Wentworth's door was open because she has that open door policy, as she calls it. I put my head in and said good night. She was already in bed and said "night night, Stevie. Thanks you for taking care of me today. I hope you get to sleep easily." 

I changed pretty quick and got under the covers and masturbated right away. The panties were my inspiration. The open door rule made me be nice and quiet as much as I could so she didn't hear. But I came pretty fast and the panties reminded me of the new amazing that happened and all the amazing things that had happened all day. It was a wild day and I fell asleep smiling and looking forward to the next day.