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.