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.