Author Topic: Becoming Becky Pt 2 by Janet House  (Read 2992 times)

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Becoming Becky Pt 2 by Janet House
« on: February 19, 2016, 12:06:15 PM »
Becoming Becky
Chapter 4 – Preparing For Our First Tutoring Session
What I had told Lawrence about me being tending to stay up late was true.  I really wasn’t much of a morning person so I slept in a bit on Saturday.  I finally got up around 10am as I had several things to do today in preparation for tonight.  I honestly intended the focus tonight to be on math as I needed to get up to speed, but I also wanted to be able to dig into Lawrence’s apparent submissive proclivities a bit and to do that I needed a few things.  So I quickly showered and dressed, and finished off last night’s dinner for my breakfast before heading out. 
My first stop was a liquor store.  I’m not much of a drinker, but I do enjoy a decent wine from time to time and thought I’d get a bottle so I could relax a bit this afternoon once everything was done.  I also needed to grab some more Capri’s and a lighter to replace the one I had given Lawrence in case he failed to follow directions.  I’d be less than amused if he failed to do so, but I wasn’t about to sacrifice our arrangement over it either. 
My next stop was the grocery store.  I needed to do my weekly shopping, but I also wanted to grab some Coke for Lawrence as I wasn’t about to give a minor wine, especially since he’d be driving home.  I also made a point to grab a couple of frozen pizzas.  They weren’t really my thing and I knew Lawrence was supposed to be having dinner with his Mother, but I thought they’d make a nice snack when/if we took a break from the math.  I had a couple of other errands to run which took longer than I expected.  But I finally got them completed and was able to head home.  By now it was mid-afternoon, so once I had everything put away, including getting the wine into the refrigerator, I made myself a quick lunch and then set about getting the house ‘company ready’. 
My house was nothing overly special.  For the area it was in, it was an average sized ranch home that I had been able to purchase with some money my parents had left me along with most of the divorce settlement I had received.  I had gone against my lawyer’s wishes and not pursued alimony, but I had let her talk me into pushing for a moderate sized lump sum payment to “get me on my feet”.  I had just enough money to pay cash for the house so it was mine free and clear.  I was grateful for that as not having a mortgage provided me with a lot more financial freedom than many people my age.
The front door opened up into the living room and from there you could either head down the hall to the bedrooms and bathroom (one in the hall and one in the master bedroom) or you could head into the kitchen/dining room area.  I had decided that the best place to study would be in the dining area as there was plenty of bright light and minimal distractions.  I’m not one to be messy, but I still spent a good hour touching up the living room, bathroom, and kitchen/dining areas.  By 6pm or so everything looked good as far as having a good clean study area, etc.  I had three hours to kill, so I decided to take a nice long hot bath, one of my guilty pleasures.  As the tub filled, I added in some of my favorite bubble bath and went and got a glass of wine.  Before I knew it I had been in there for nearly a hour and it was approaching 7pm.
I had a few more things to get ready so I scurried out of the tub to get dressed.  When I had been shopping the prior week for the ‘soccer mom’ clothes, instead of picking up ‘outfits’, I picked up several separates so I could mix and match.  I settled on a cute sweatshirt and a pair of jeans.  This time I paired them with a more typical, at least for me, pair of heels.  Since I’d only be walking around the house I went with a nice 4 ½” pair that would actually make me a touch taller than Lawrence which is what I was going for.  For makeup, I went subtle with two exceptions.  Those were the same red lipstick from the prior night and some heavy black eyeliner.  The lipstick was for obvious reasons, and the liner – well it makes my eyes pop and I wanted to encourage him to look directly at me since other than when I was smoking, he had a real issue with eye contact.
Once I was dressed I had a couple of last minute things to do.  First off I just adore candles, and have them all over the place.  I lit several in the living room and killed the lights.  At the same time I popped in a Kenny G cd and put it on repeat.  I actually like a lot of his music as I find it very relaxing.  The combination of the candle light and the music made the living room into quite the relaxing area.  I also set out an ashtray in the living room as I intended on smoking in there, which is also why I went with the candles and music.  I wanted to focus on his fetish and I thought this was the right atmosphere for that.
By now it was after 8pm, so I had a bit of time to kill.  I went to the kitchen and made myself a quick snack.  I was tempted to have another glass of wine, but I decided against it as I knew I’d want some later and I didn’t want to compromise my judgment.  As 9pm creeped closer, I found myself actually a touch nervous.  Not over the tutoring, but over the thought of if I should bring up Lawrence’s apparently submissive nature tonight or to wait.  To take my mind off of that I went and got my satchel with my math book, notebook, and calculator and set them on the table.  I also ran out to the car and got Lawrence’s things as I had left them out there the night before. 
About 10 minutes before 9, I went and poured myself a small glass of wine and filled a glass with some ice cubes and a can of Coke for Lawrence and took them into the living room.  I then went and grabbed the pack of Capri’s from my purse and the lighter I just bought and brought them into the living room.  The way my living room was laid out was a couch along the wall with a coffee table in front of it.  A television that almost never was turned on across the room, and two nice chairs on the short sides of the coffee table, one facing the door and one facing towards the kitchen. 
I elected to place my things on the end of the coffee table closest to the door and his Coke on the far end so we’d end up in the chairs facing each other with his back to the kitchen area.  I drew the curtains shut to block out the extra light and turned off the kitchen lights so that the candles provided the bulk of the illumination in the room.  At the last minute I ran and got my lipstick and placed it near the cigarettes.  I wanted to be able to touch up my lipstick so I could give him the full effect.  I also moved the lighter behind a picture so it was out of sight.  I needed it there in case he failed to bring the one I had given him, but I didn’t want him to think I didn’t have faith in his ability to follow directions.  At this point it was maybe 5 minutes prior to 9 so I sat down to wait.  Just as I did I thought I heard a car pull up over the music.  At this point I was able to relax a bit as I knew I hadn’t scared him off. 
I waited expecting to hear him at the door, but the minutes ticked off without either a knock or the doorbell going off.  I was starting to wonder if I had been mistaken about the car earlier.  Finally, right at 9pm, I heard a knock.  It was literally the most timid knock I’ve EVER heard in my life.  I started to get up to answer the door and thought better of it.  I decided to wait until he knocked again.  A minute or two passed by and there was another knock.  Not much better than the first, but considering his apparent submissive personality I felt that might be as good as it was going to get and I didn’t want to chance him leaving so I headed to the door.

Chapter 5 – The Arrival

I opened the door and much to my surprise he looked far better this evening.  The clothes were similar but they weren’t wrinkled up like what he had worn the prior night and even his cologne was more tastefully applied, though it was still a scent I would not have recommended.  He still wouldn’t have been somebody that I would be attracted to, but he had definitely improved his appearance from the night before.  But there was something off with him, I just couldn’t place what it was.
I invited him in suggested he sit down so we could chat for a bit before we got into the math.  I pointed to the chair I had placed his soda at and I went to the other chair and sat down.  He stood there for a moment as if he was unsure if he really should sit down.  “Lawrence, please sit down.  There’s a Coke in front of you if you are thirsty.  I’d offer you a glass of wine, but since we’ve established that you’re not old enough to drink, Coke is as good as it’s going to get.”  I hoped my attempt at levity would loosen him up a bit and it seemed to as he did go over to the chair and sit down, and while I watched him take a quick glance at me, his eyes went to the floor almost immediately.
I took a sip of my wine waiting to see if he was going to say anything, but when he didn’t I decided to break the ice myself.  “So Lawrence you look much nicer tonight, how was your dinner?”
Without looking up he said, “It was fine I guess.”
The “I guess” part of his response got me, there was obviously something bothering him and if tonight was going to be productive I felt that I needed to try and get him past whatever it was.  “Your tone didn’t make it sound like it was ‘fine’ and your demeanor also indicates otherwise.  What’s wrong?”  I could tell he was reluctant to discuss whatever it was and I was getting ready to prod him further when he finally spoke up.
“It’s just, well my Mom and Sister really tried hard to make it a good night, but it was the first time I could remember going out for my birthday where all five of us weren’t together and – well it just depressed me for it to only be the three of us this time.”
“Lawrence, I’m sorry about that.  If you don’t feel up to doing this tonight we can try another night.”
He thought about that for a moment and I thought he was going to take me up on it.  After another minute or so, he finally spoke.  “No, I don’t want that.  I don’t really know why, but I’ve been looking forward to this all evening.  I do like to help people, it makes me feel better about myself.  I just usually don’t get an opportunity to.  I’d really like to stay Janet.”
I believed what he said, but I was torn.  I was sure he could help me with my math regardless of how he was feeling; but was that really fair to him?  And from a selfish perspective I was afraid that the other reason I had him here wouldn’t go well with him in this state of mind.  I guess the internal debate I was having was taking too long as when I looked over at him, he was actually no longer looking down at the floor, but rather right at me.  That made my decision for me.  “Lawrence, if you are up for it, I would like to spend the time going over what we’ve covered the first few weeks of class.  I am hopelessly behind and if I don’t get caught up soon I’m afraid I won’t be able to catch up.  Why don’t you drink your soda while I go get things setup in the other room.”
I didn’t need to setup anything as it was already done, but since the lights had been off in there and his back was now to the kitchen area he didn’t know that.  I thought he could use a couple of minutes to compose himself and I wanted to give him that time.  So I went in turned on the lights and shuffled some things around so it seemed like I was busy.  I probably gave him 3 or 4 minutes before I turned the lights off and went back into the living room to sit down.  He still didn’t look overly happy, but he definitely looked better than he had a scant few minutes prior.
I took another drink of my wine before speaking.  “Well, before we get started on my math issues, I believe we had an ‘arrangement’, are you still agreeable to that?  If not, my original offer to pay you for your time still stands.”  I barely had the words out of my mouth before he started to speak. 
“Yes Janet, I’m very happy with what we agreed to last night.  I’d like to stick with that if you are still willing.”
“Lawrence, I never go back on my word, and perhaps this will brighten your mood a little bit.”  I started to reach for a Capri and thought better of it and grabbed the tube of lipstick instead.  I really didn’t need to touch it up, but he wouldn’t know that and I thought it would be a nice touch to the performance.  I made a real show out of taking the top off, screwing the lipstick up and out of the tube, and applying it.  I had to be careful as while I’m pretty good without a mirror, I’m not perfect and I didn’t want to mess up what I had so carefully done earlier.  I made the same show out of twisting it back down and putting the top back on.  Looking over at him, he was watching me intently so I knew the effort had been worth it.  With that I picked up a Capri and looked back over at him.  I had hoped he’d be smart enough to come over and light it for me without being prompted, but alas that was not to be.  So after a few seconds I finally spoke up.  “Lawrence, didn’t I just say I never go back on my word?”
“Yes you did Janet.”
“Well Lawrence, what was one of the last things I told you last night?”
It took a few seconds, I suppose he was thinking about everything I might have said.  Finally the proverbial lightbulb went on for him and he replied with “You told me to always have a lighter with me.”
“Lawrence that’s mostly correct, but there was more to it than that, wasn’t there?  Didn’t I also tell you that if you forgot then you’d simply lose out that night?”
He replied, “Yes you did.  I’m sorry, I do have it.”  With that he stood up and dug it out of his pocket.
“Well Lawrence, it doesn’t do a lot of good over there now does it?”  With that I put the cigarette up to my lips and simply stared at him.  Thankfully I didn’t have to say anything else, he walked around the table and lit the cigarette for me.  I took a nice long drag and exhaled it up towards his face.  I still wasn’t quite sure if that was part of his little ‘fetish’ or not, I’d have to eventually find out.  But for now it worked for me.  When it became obvious he wasn’t going to do it on his own, I waved him back to his chair to sit down.
Once he had returned to his chair I took another long drag from the Capri and held the smoke in for a bit longer than normal.  I then looked him right in the eyes and exhaled a nice thin stream of smoke in his direction.  Setting the cigarette down in the ashtray I asked, “Last chance Lawrence, are you sure you prefer this to me paying you for tutoring me?  I won’t ask again.”
As he had done earlier, he replied almost before I had finished my sentence.  “Yes Janet, this is what we agreed to and it’s definitely what I want.”
“Good, I think this little ‘arrangement’ of ours works better anyway.”  This seemed to puzzle him a bit which was my intention, but before he could say anything I cut him off.  “What did you tell your Mother about tonight?” 
She actually perked up when I asked her that and said, “Well, I wasn’t sure what excuse to give her.  So I waited until she was heading off to bed for the night and told her I was going to run up to work and meet with a couple of people to go see a late movie for my birthday.  She’s friends with the parents of a girl I work with named Erica.  When I mentioned that Erica was going she didn’t give it a second thought and told me to have a good night.”
I was actually impressed with that, though I was still a bit disturbed that his Mother was treating him as less of an adult that I felt he deserved.  But that was a discussion for another time if things progressed that far.  The Capri was about half done by now so I said, “Why don’t you sit back and relax and watch me finish this and then we can get to work.”  I had another drink of my wine and drug the cigarette out as long as I could for him, but eventually it was finished so I put it out in the ashtray and stood up.  “Well it’s time to get working, I’ve got everything setup in the kitchen.”  With that I headed in there and turned on the light as he followed me in there.
We spent about 90 minutes or so going over the lessons from the prior week that I had been having problems with.  At that point I really needed a break and truthfully I was actually getting a touch hungry.  I looked over at Lawrence and suggested a break.  He didn’t say it, but he looked like he needed one too.  So I stood up and said, “Are you hungry?  I am and I was thinking about throwing some pizza in the oven.”
He thought it over briefly, and said “Actually I am a bit hungry.  I didn’t eat much of my dinner earlier.”
As I headed over to the freezer to get the pizzas I told him that if he needed to use the bathroom that it was down the hall and on the right.  Obviously he did as I didn’t have to tell him twice.  I turned the oven on to preheat and figured I’d put the pizzas in when he returned.  Per our arrangement, I wanted to have enough time to ‘indulge his fetish’ while they were cooking.  He actually got back a little quicker than I expected so the oven wasn’t quite warmed up enough.  I offered him another Coke and got one myself.  I wanted a glass of wine, but I had already had two and I planned on having one more later, and three is about my limit.  By the time I had done that the oven was ready so in went the pizzas and I suggested we adjourn back to the living room to wait for them.  I let him go first so I could kill the lights in the kitchen again.
Once we got in there and were seated as we had been earlier, I repeated the process from earlier.  I made a show of touching up my lipstick and got out another Capri.  This time I didn’t have to say anything, he got right up and lit it for me and went and sat back down.  Despite his obvious social awkwardness, he was finally picking up on a few things.  We sat there for a couple of minutes, me smoking, and him watching me intently.  Maybe it was the couple of glasses of wine, maybe it was just me being me, but I decided to push things a bit more.
As I finished the Capri and put it out in the ashtray I looked over at him and said “Chuck…”  As soon as I said it his mouth dropped a bit and he started to say something but I cut him off.  “Chuck, and yes I called you that intentionally.  I’ve made a bit of a decision.  I want to keep the tutoring as we’ve discussed and as such when that’s going on I will refer to you as Lawrence.  But when we are on break and for that matter possibly other times I would like things to be more casual so I thought that using Chuck would help with that.  I’m assuming you’re fine with that?”
He replied with “That’s great, I really do prefer Chuck.”
 “Okay Chuck, we have a few more minutes until the pizza is done and I’ve taken care of my end of our bargain on our little break.  Since we are now that we are on a more personal level at the moment I’d like to ask you a few questions while we’re waiting.  You don’t have to answer anything you aren’t comfortable with, but I would prefer that you did.  If you answer all of them I’ll have another Capri for you after we’re done with the pizza but before we get back to the math.  Are you up for this?”
He didn’t answer quite as quickly as he had earlier, but as I expected he quickly agreed.
“Okay Chuck, first question.  Do you have a girlfriend?”
He looked a touch embarrassed at the question and simply nodded his head no.
“That’s not quite good enough for me, please answer me with a ‘yes’ or a ‘no’ like we talked about last night.”
His face turned a couple of deeper shades of red before saying, “No I don’t.”
“Next question, have you EVER had a girlfriend?”
I didn’t think it was possible, but he got ever more flushed.  “Not really Janet.  I mean there are girls I’ve liked and there are girls I’ve hung out with, but it was always more of a friendly thing than anything.”
This didn’t surprise me, considering his submissive traits he was a prime ‘friend zone’ candidate.  Part of me felt a little sorry about this, but a bigger part of me was ecstatic as these answers were only confirming that he’d likely make a good submissive for me.
I could just make out the timer on the oven and we had about 5 minutes left, so I figured I had time for a couple of more questions.  “Next question, are you more of a follower or a leader?”
He actually took a moment to consider this before answering.  “Well, if we are talking about work, then I’d say a leader.  I can make good decisions, I can make quick decisions, I can stand up for my people, and so on.”  He paused for a moment before continuing, “But the truth is that while I think I do a good job as a leader at work, I hate it.  It’s not me.  I don’t like having to make decisions that impact other people.  If I screw something up and there’s a price to pay for that I’ll gladly pay it.  But if someone else has to pay a price for something I did, that pains me to no end.  So while I have to be a leader at work, everywhere else I suppose I’m a follower.  It bothers me that I feel like that, I shouldn’t be that way, but I am.”
Part of me hated asking him to answer that question, but I really felt it was important.  He all but painted a picture of himself as a submissive, he just didn’t realize it.  It was at this moment that I knew I should pursue this with him.  “Okay, we have a couple more minutes, so one last question.  Tell me the most embarrassing thing you’ve done in the last year.”
He looked right at me, the embarrassment oozing from his face and said, “Please don’t ask me that, ask me something else instead.”
For a moment I almost relented, but I thought better of it.  I wasn’t looking at something to hold over his head, rather at this point I was hoping to maybe let him get something off his chest that he had been hiding.  I calmly looked right at him and said, “Chuck, as I said before we started, you are welcome to not answer the question.  But I will NOT take it back and I will NOT ask you a different question.  Either answer it and I’ll keep my end of the bargain, or choose not to and we can eat our pizza and get back to our math.”  He sat there in silence for a good minute.  I glanced into the kitchen and saw we were down to a bit over a minute until the pizza was done.  “Chuck, you have about 60 seconds before our pizza is ready.  You either need to answer the question or we should go ahead and head back into the kitchen.”
He took a deep breath and the words came rushing out. 

Chapter 6 – The Surprise

“I like to wear my Mom’s clothes when she’s not around.” 
As soon as the words registered with me, I realized I had the daily double in front of me.  Not only was he apparently a natural submissive, but he liked to wear women’s clothes as well.  This was definitely something I could work with.  Before I could say something the oven time went off.  So I looked over at him and said, “I should go get the pizza before it burns.  Can you please bring our glasses into the kitchen while I get it out of the oven?”
I flipped the lights back on as we entered the kitchen.  Since I didn’t want to get sauce and cheese all over our things I told him to sit at the far end of the table and we’d eat down there.  I cut the pizzas and put them on the table and got us plates and him another Coke.  I on the other hand decided that it was time for that third glass of wine. 
I reached for a couple of pieces and he did the same.  It was sort of refreshing to see him do so without being prompted.  Perhaps baring a dark secret was going to have a positive impact on him.  We ate in silence for a couple of minutes, but I couldn’t help myself.  I had to push him just a bit further.  So I asked, “Chuck, I stand by what I said in the living room.  You answered my questions and when we’re done eating I’ll keep up my part of that deal.  But that last question, well I think that deserves a little bit of explanation and I think you might feel better if you’d be willing to answer a few more questions about it for me.  Just let me be clear, you don’t have to answer anything you don’t want to.  This isn’t a quid pro quo like earlier, I simply think getting this off your chest might help.”
He sat there for a moment chewing on his pizza, not even looking at me.  He finally swallowed the pizza and looked up.  I could just make out a tear in the corner of one of his eyes.  He took his glasses off and stared straight at me and said “Okay.”
Part of me wanted to chastise him for that since we had talked about it twice already, but I didn’t have the heart do to it now.  I looked back into his eyes, the boy really had beautiful eyes.  He needed to get rid of those horrible glasses and get some contact lenses.  They’d do wonders for his appearance.  But that was really beside the point at this moment.  I took a deep breath and said, “Why do you wear your Mothers clothes?”
He sat there for a moment and again looked down at the table before he started to speak.  “I, I, I don’t know Janet.  I just do.”  He paused briefly and then started speaking again.  “That’s not true, I do know.  They are so soft and nice.  I feel better about myself when I wear them.  I know I should be ashamed that I do it, but I can’t help it.  I just can’t.  Something is wrong me with to like that and I know I should stop, but I just can’t.”  A couple of more tears ran down his face and he fell silent.
I reached over and put my hand on the back of his neck and said, “Sweetie, it’s alright.  It really is.  Lots of men like to wear women’s clothes.  I know there’s at least one in my office that wears a bra and pantyhose under his clothes.  I saw the bra straps one day when he had his jacket off and his socks slide down on occasion and you can clearly see suntan pantyhose under them.  I don’t think any less of him for it, in fact I think better of him for it.  He’s doing what makes him happy regardless of what others might think.  It takes a strong person to do that.”
He wiped his eyes and looked up at me.  “Really?  He really goes to work like that?  I’ve never done that, I’ve only done it around the house when everyone is gone.”
“Yes he does, and I highly doubt he’s the only one there.  It’s far more common that you might think, especially among men who are in higher stress jobs.  For many of them it’s sort of a ‘stress reliever’ of sorts.  For others it may be more or less than that.”  I let that sink in for a moment, before continuing.  “The next question, and it’s one you probably need to give some thought to, so don’t answer it now, is WHY do you like wearing women’s clothes?  Being able to answer that will go a long way towards helping you get comfortable with doing so.  I’d really like it if you’d spend some time this week thinking about that and we can revisit that question at our next tutoring session.  At least we can if you are still planning on tutoring me.”
He pondered that for a moment and said, “I agreed to it and I like to keep my word, but more than that I want to do it because I like our arrangement and I’d hate to lose that.”
Again, maybe it was the wine getting to me, but I had a thought.  “Let’s finish our pizza, then we can go back to the living room so I can make good on our question deal, and then I have something that I think will make you feel a bit better.”  He nodded his head and we made small talk for another 10 minutes or so as we ate.  Once we were finished, I took the dishes and to my surprise he grabbed a dish cloth off of the sink and wiped down the table.  We then adjourned back to the living room where I kept my word and had another Capri as he watched.  Once again it seemed to perk him up, but I thought what I had planned would perk him up even further.
As I put the Capri out in the ashtray I looked over at him and said, “I’ll be right back, why don’t you head into the kitchen so we can get a little more work in before you need to head home.”  With that he got up and headed that way and I went down the hall to my bedroom.  One of my vices in life is higher end lingerie.  Bras, panties, garters, stockings, you name it and I’ve spent far too much money on it.  But for all the nice lingerie I had, I also kept a few cheaper pairs of panties around for the ‘monthly inconvenience’.  I normally bought these in packages from places like Wal-Mart or Target.  I also generally bought them a bit bigger than my normal size which would make them perfect for what I had in mind.  Now it was just a matter of where I had put my most recent purchase of them.  Thankfully it only took three drawers before I found what I was looking for.  It was a package of 6 with 4 pairs still in it.  I grabbed 3 of the four pairs and sized them up.  He was bigger and heavier than I was, but most of that was in his upper body.  His waist actually wasn’t all that far off from mine and while these would be snug on him I thought they’d work and the fact that they were snug would actually be a benefit as they should ‘rub him nicely’ so to speak.
I headed back towards the kitchen with my little surprise tucked behind my back.  He was sitting down ready to go, I almost think the studying qualified as his ‘safe place’ and he was back in it.  I looked at him and said, “I know we’re back in here to study, but for the moment I want to stay in the ‘Chuck zone’ with you.  I’m going to give you something in a moment, but before you say anything I want you to promise to hear me out completely.  If you can’t agree to that I’ll drop the issue and we can resume studying.  So will you make that promise?”
I could tell I was asking a lot of him, here he was in my house and yet he barely knew anything about me at this point.  Yet he had already bared several things to me that he probably had no intention of ever telling anyone.  He was obviously a special person and apparently nobody had ever taken the time to notice that.  After a few moments he looked up at me and said, “Yes Janet, I promise to listen to everything you have to say.” 
“Well then Chuck, please close your eyes and stick your hands out in front of you.”  He did so and I laid the panties in his hands.  “Please keep your eyes closed until I’m done talking.”  He nodded his head in agreement so I continued.  “What you have in your hands are three pairs of panties.  Three pairs of women’s panties.  They’re probably a bit small for you, but they were fairly inexpensive so if you stretch them out it’s no big deal.  What I want to ask of you is this.  Please go to the bathroom and change into one of the pairs, please leave your own underwear in there for now.  I don’t care which color you prefer, but pick the one you like best.  Personally I like the pink, but the green and yellow are very nice colors as well.  Once you’ve done that, I want you to come back here and I’ll finish with that I have to say.  Since I’m not done yet and you promised to hear me out, simply open your eyes and please go do as I asked.  Once I’m done if you aren’t happy with what I’ve had to say you can always go change back into your own underwear.  Go now.”
To his credit, he kept his word.  He opened his eyes, looked over the panties and set the green and yellow pairs on the table and took the pink pair down the hall.  A minute or so later he returned and while there was some apprehension in his face, he really did appear to be at least a bit happier than he was just minutes earlier.  I looked at him and then said, “Okay please sit back down and let me finish.”  Once he had done so I continued on.  “It’s Saturday night.  I’d like you to wear that pair home and all day tomorrow.  I’d like you to wear one of the other two pairs to class on Friday night.  The third pair I’d like you to wear one day this week that is convenient for you.  Set them aside, and for your own sake don’t let your mother find them.  Bring the pair from tonight and the pair you wear during the week with you on Friday as well.  I’ll take care of them once you do that, the last thing you need is for your mother to find strange panties in the wash.  If you don’t want to do this, you can go back and put on your own underwear and leave the panties in the bathroom.  Otherwise, please do as I’ve asked and I’ll take care of washing your old underwear for you and return them on Friday.  If you have any questions, now is the time to ask.  If you don’t then I’d like an answer, are you going to trust me on this?”
For a moment or two I thought he was going to head down the hall and change back into his own underwear.  He looked at me, he looked at the remaining panties on the table, and then he looked back at me.  Finally he spoke.  “Yes Janet, I’ll trust you on this and I’ll do as you have asked.  But what if somebody notices I’m wearing them?  Like in the bathroom or something?”
I actually giggled out loud just a bit and I felt bad for doing so, but he was so cute the way he asked that question.  Once I composed myself I looked right at him and said, “Well you do want to be careful when you are at home as I’m sure your Mother would be less than pleased to see you wearing panties.  Beyond that, if somebody notices, then so what?  Really they are probably less noticeable than normal men’s underwear as these are a much lighter material.  As far as the bathroom goes, I’d suggest avoiding the urinals, but if you can’t big deal.  The person next to you may well be wearing panties himself.”  That brought out a bit of a laugh from him.  It was nice to hear him laugh.  It had been a rough day and evening and to hear that laugh told me if anything I had done more good than bad this evening.
I looked over at the clock and it was nearing midnight by now.  So I said, “It’s time to go back to ‘Lawrence” now.  It’s getting late, so why don’t we spend another 20 or 30 minutes reviewing a few things, then we can head to the living room and I’ll have a nice Capri for you and you get home before it’s too awfully late.”  With that we got back to it.  I still had lots that I either flat out didn’t understand, or at least didn’t understand well; but I had actually learned more this evening that I ever expected to and had new found hope that I might actually be able to pass the class with his help.
True to my word 30 minutes later I said it was time to wrap up.  I told him to grab his things, including his new panties, and meet me in the living room.  In the meantime I broke my own rule and poured a fourth glass of wine.  I figured at this point I deserved it.  I then followed him to the living room and once again went through the show of touching up my lipstick, though I was probably a bit sloppy this go around as I was starting to feel the wine a bit.  I then let him light my Capri for me and he stood there and watched me smoke it.
He moved towards the door to leave and I followed him over.  As he got there I said, “Chuck turn around for a moment.”  He did and I gave him a friendly peck on his cheek and thanked him for all the help with my math.  I then asked if he’d be willing to get together again after week’s class.
At this point he actually smiled and said, “Yes I’d be happy to do it again, but I don’t have my schedule that far out yet.  Can we work it out at class Friday night?”
I said, “That’s fine.  But I want you to make me one more promise before you leave tonight.”  He looked at me with a bit of a puzzled look on his face but before he could ask I continued on.  “In addition to thinking about WHY you like wearing women’s clothes, I want you to do one other thing for me.  I want you to think about WHY you chose to be so open with me the last two days.  The answer to that question is very important to me.  Do you understand that?”
From the look on his face I don’t think he really had any type of an answer to that question.  I took that as a good thing as I felt that meant he did it because he felt he could trust me, that he felt safe around me, and if there was in fact any chance of us pursuing a D/s dynamic those feelings were crucial to it working.
Despite the quasi-puzzled look, he quickly said, “Yes Janet I understand and I’ll have answers for you the next time we get together.  Thank you for dinner, and everything else tonight.  It really meant a lot to me.”
With that I let him out, but not before asking him to call my number when he got home and let it ring three times and hang up so that I knew he made it home safely since it was late.  20 or 30 minutes later the phone rang three times and stopped.  I finished up my wine and headed off to bed, more pleased with myself than I had been in a VERY long time.



 

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