My Ex After the Drive In Pt. 02

Sorry for the short part 1; will make the rest longer

Over the next few weeks, things went on pretty much as normal. She went to teach, I went to work in NYC. We talked a bit about that night, but that too began to fade. Perhaps for her, but not in my mind. I needed to come up with a plan.

I started to think what hadn't we done that I would love to do. What had I wanted that she either refused or I felt nervous in bringing up? That brought me to two things: dressing up and toys. Combine that with idea of her liking being paid for, an idea started to come to immediate clarity.

I went to a mall far from us that had a Victoria's Secret store. I didn't want anyone who knew us to see me. I needed to protect her good girl image -- and someone seeing her husband in a lingerie shop would kill it -- at least for me. She never wanted to wear those types of things -- no matter how I asked -- so this was my opportunity to finally get her in those types of outfits.

I picked up a few things -- small black see-through bra, garters, black stockings, high cut bikini panties and a string tied thong with a simple string in the back which would ride up her crack. I also added some heels -- not big ones, but three-inch, which was way out character for the good girl. Every pair of shoes she had were what I called clunky teacher shoes -- brown, small heel, and very comfortable. Also -- very boring!

I then drove to a sex shop about forty miles away. Again, I really didn't want anyone to see me and get ideas. I knew I wanted to add in sex toys but not being very experienced in this, I started to look around.

After a few minutes I got ideas of what I wanted. I saw a ball gag, and that gave me thoughts. I picked it up and then added a blindfold. I then went for the dildos, - and got a good sized one -- slightly bigger than Jimmy's cock from the other night. I picked up a rather large black one, and a small thin one.

I was about to leave and then saw collars and leashes. That really made me think! And I grabbed a collar and leash that most looked like you would use for your pet dog. Then I saw some ropes and cords supposedly good for tying someone up. We had never done bondage at all, never really talked about it, and I wasn't sure I wanted to, but bought them any just in case the right moment happened. I figured I had one shot at this -- better be prepared. When I went to the counter, the person there asked if I was planning a party. I looked at him and said, "You have no idea!".

When I got home, I left the stuff in the trunk of my car. I went to the apartment and found a note from my ex saying she had gone and would be home around dinner time.

Great!! I went back to the car, got both bags, and placed them in my dresser drawers under clothes. We did our own laundry, so there was no chance she would find them.

That night we were having dinner and I said "Do you remember our conversation about me planning something for us?"

She stopped eating. She gulped and said, "Yes, I do."

I asked if she was still willing to go through with it. She slowly nodded. She was really nervous anticipating what was next.

I almost coldly stated, "I set the plan in motion. One day, and it's not today, I'll let you know what we'll be doing. And once we start, you can't stop. Ok?"

She got really quiet.

I got closer and held her hand. "Did you enjoy what we did a few weeks ago and that I will take care of everything?

She smiled and nodded yes. She leaned over to kiss me and we had sex right there on the dining room floor.

I really thought about setting my plan in motion the next morning, but I wanted to wait so there were no distractions. I had a ton going on at work (not that I was concentrating on that), and she was starting a new term and there were night meetings and things. So -- I waited a few weeks.

I picked a day -- a Friday. Have the weekend to deal with the aftermath. On Thursday night, I put the Victoria's Secret stuff in a bag on her side of the closet. I put the other bag from the sex shop on the other side. I put the bondage ropes in one of my drawers - still wasn't sure if I wanted to use them. I went to the bank and got a few hundred in tens and twenties. She liked the idea of being paid for sex? Well, she was going to earn real money that night.

On Friday morning, I left the house early -- before she woke up to go teach. About 6:45AM, I called the apartment. She picked up the phone and I said it's me. She sleepily remarked about me leaving early, and I responded.

"Today's the day."

Still sleepy, she said, "What day?"

"That day."

She got quiet and said oh. I asked if she was still willing to go along with whatever I said. She took a deep breath and quietly said yes.

Then I paused and said, "Ok. If you're still game, go to your side of the closet. There's a bag in the right corner. Go get it but don't look at it."

She put the phone down and went to the bedroom. She came back to the phone and said she had the bag.

I said, "Good, now open it."

I heard the bag rustling, her hand going in, and heard her muttering as she looked at the bag contents.

She got on the phone. "What is all this?"

"Do you see the lingerie and heels?"

"Yes?"

"Today you're going to wear them under your teacher clothes and go to school. You're going to be like one of those professional high-class women who have regular good jobs during the day and are paid for whores at night."

The phone got real quiet. I asked, "Do you agree with this? If you don't, that's fine, but if we start, there's no turning back"?

Still silence, then a meek, "I agree."

Then I dropped the hammer. "And now look on the side of the bag. Find something taped." There was more rustling, and I heard the ripping of tape from the bag.

"What did you find?"

"It's a twenty-dollar bill! What's that for?"

"You told me the night with your former student whores get paid in cash. Today, you're going to earn your money. Every time you complete something, you get twenty dollars. The more you do, the more you earn. Just like a good little working girl."

She started to breathe a bit heavier.

I then said "Think of this as the ultimate good girl gone bad event. You'll be teaching in that plaid jumper of yours, the blue button-down blouse, and underneath you're dressed like a high-end call girl. And for the panties, for now wear the bikini high rise. That will make your ass stand out to those horny male teacher colleuges of yours!

She started to breath heavier now and I wanted to see if she would follow orders.

"So -- for wearing those things -- you just earned twenty dollars. Want to earn twenty more?"

All I heard was a breathy yes.

"Make yourself cum. Right now!", I commanded. "I want to her you make yourself come!".

I was wondering if she would do it until I heard her rubbing herself, sticking her fingers in her pussy, hearing the squishing sounds as her pussy got wetter and wetter.

I then said "Make this good. I need to hear you. I want my money's worth!"

That got her going. She took a couple of deep breathes, starting moaning and then grunted as she came. She calmed down and then said on the phone, "That good enough?"

I said yes. And then she quickly said, "Good. Now where's my money!"

She was in -- she would play the rented woman. She was planning to play the paid whore for me. I said, "Check behind the kitchen cabinet door."

She walked over and then came back. "You taped a twenty to the door? Am I to assume there's more around here?"

"Could be!", and then said, "Congrats! You just earned your first forty bucks as a sex worker!".

That entire day at work was a blur. I was worthless. My mind certainly wasn't on creating ad campaigns for my clients or worrying about expense reports. And I had a few things I wanted her to do during her work day.

I knew her first break was at 10:30. So, I called the school and asked for her. She came to phone and said hello. They didn't ask who it was, so she didn't know who was on the other end.

I responded, "The man who's paying for your services."

She almost cooed into the phone, "Oh, it's you. Nice to hear from you!"

I said, "Yeah, how's those clothes feeling? Getting a bit of a thrill?"

"I swear some of the people know what I'm wearing. I'm not used to garters so I keep on trying to straighten them. I think some of the others got a glimpse of the stocking tops!"

"Well, remember you're paid for what you do! Don't give anything away unless they pay!!"

"I'll keep that in mind."

I then asked, "Want to make another twenty dollars?" I was going to keep this earning aspect up, so she felt like she was really being paid for by a client and not her husband.

"Ok". There was no hesitation. "What do you want me to do?"

"Go to the bathroom, take off your panties, put them in your purse, and make yourself cum."

"What?"

"You heard me. Make yourself cum right now, and work the rest of the day without underpants." I added the underpants part to make it sound more innocent. "Check your purse -- see what's taped to the side."

She responded, "It's another 20".

I said, "Yep. You do it, you earn more. If you haven't guessed by now, you're my personal whore for the day, and you can make a shitload of money today. All you have to do is obey and do exactly what you are told. Agreed?"

She exhaled and said "Ok. I'm your bought and paid for girl. I could use the money!"

And that's when I was pretty sure she'd to do anything I wanted -- and she was ok being paid as a whore -- even if it was coming from her husband and our house money. I told her to go do what I had asked and call me back. True to her word, she called me back.

"I did what you asked"

"Did you make yourself cum?"

"Yes -- it didn't take long. You might want a refund."

"No -- I'll get my real value later."

She asked, "What does that mean?"

I didn't explain -- I hung up the phone and went back to work.

During her second break, I called again. This time they told her it was her husband.

"Yes -- what's next?" She was now into it -- taking orders and being docile -- paid and docile.

"When you get home, put on the other pair of panties -- and take off your clothes except for the undergarments. Put on those new shoes from the bag. I want you to do you daily things in underwear -- and keep the blinds open.

She gasped, "All the way???"

" No -- just at halfway so the slates are all even. This way, people may see you, but not sure what they are seeing. "

"What do I get for that?"

"God, all you sex workers are about is money. Ok, there's another twenty underneath the top of the silverware drawer. It's yours when you do it."

She quietly agreed. I then said there's one more thing.

"What?"

"That other pair of panties has a very small front. I don't want to see any hair poking out of there!"

My ex wife was a bit puzzled. "What are you suggesting?"

"Well..", I responded, "There's shaving cream and a razor on my side of the bathroom cabinet."

The phone went dead. There was no response, and I thought I had blown it. Our little sex game was going to be over. But just then, she spoke in a very little voice.

"What do I get for that?"

"Twenty bucks. Like everything else."

She simply said I understand, and I said ok. She asked if I was going to say anything else. I replied no; you don't have pleasantries with things you paid for -- and then hung up the phone. My guess was being treated like a common street walker was getting her off and she was having an orgasm -- right in the teacher lounge.

I stayed at work for as long as I could stand it, but left about 4 and made my way from the city to Central Jersey. I took the bus home, and had to try and keep my raging hard on from springing out. It was an uncomfortable ride to be sure.

I got to the bus stop near our place, and went to the phone at the 7-11. I called the house and put the next phase in action.

"Hello?", she said.

"What are you wearing?", I said, not trying to discuss my voice.

She said, "Oh, it's you. Just what you paid me to."

I took a breath. If I could get her to do this, then she really was mine.

"Ok -- I'm at the 7-11. I'm going to walk to the street outside our window. Open up the blinds all the way and stand there so I can see you're not lying. You don't have to open them until you see me."

"Ok.", she said. "That's 20 bucks for the view."

I responded with a simple sold. I knew she was getting in to it. And sold was becoming the word for the day.

I walked down the street about 100 yards to our place. Our living room window was on the second floor, right in the middle of the courtyard facing the main road. When I got there, I looked up right at our window. I saw her there, looking through the shades, and as soon as she saw me, she starting lifting them up.

The blinds went all the way to the top, providing a slow big reveal. Slowly, her body came into view, standing there in garters and suspenders, in that new sexy bra showing off her tits just so, and the new panties. You could see the small piece of fabric covering her pussy -- and from my view, didn't see any hair there. She looked incredibly natural in those types of clothes, even though she never wore them before. Heck, she always refused to wear them.

One inhibition had dropped away. And then she did the unexpected. She turned around and her perfect ass was in front, with the single line of fabric almost swallowed by her cheeks. She walked away from the window, and then back towards the window so anyone who was out there could see. She then sat down, and I motioned for her to close the blinds. I don't know if anyone saw us. I was hoping they did.

I walked back to the 7-11 phone booth and called her. She picked up immediately and asked where I was. She was breathing heavily and she was really turned on by that very simple performance to me and whomever of the neighbors might have been watching,

"You have a nice ass.", I said. "Glad I'm paying for a top flight looker."

"Thanks. I work out." Then she asked again where I was.

"I'm back at the 7-11. You're really earning your money today. How much have you made so far.?" I wanted to keep focusing on the money, to reinforce she was really acting like a call girl -- getting paid for various sex acts just like any street walker.

"About 80. You still owe for what I just did". She was playing along and I loved it.

"You'll get it when I get back. When I get there, have a drink for me -- and keep wearing what you have on!"

"Ok, not sure what you're going for, but ok." She hung up and I knew she was wondering was next. From what she was wearing to being paid for simple sex acts and shows, I had her off her game, and that was needed when we got into the rest of what I had planned.

I drove back to our apartment and had to stop myself from running right into the place and fucking her brains out. If this was all going to work, I needed to stay calm and in control. I had second thoughts on what we were doing, but decided we could stop if we wanted to. And she could always say no. That's how it had to work.

As I went upstairs, I realized she would expect me to use my key. After all, I lived there. So, I decided to keep changing things up. I went upstairs and knocked on the door -- very hard. I'm guessing the knock startled her, as it could have been anyone and she was walking around almost naked in stockings and hooker heels.

I heard the clicking of the heels on the hardwood floors and she got closer. She got to the door, paused, and then stuttered out, "Who...who is it?"

I just said through the door, "Your next customer!" She kind of giggled and said hold on.

She slowly opened the door just slightly, peered out to make sure it was me, and then opened the door all the way. I was stunned! There she was -- all dresses up like a high-class hooker in the new stuff I bought her. The see-through bra, stockings, garters, in three-inch heels, and the very small thong panties. She leaned against the door jam like in the old movies, arm upon the side and a look that said come in and fuck me. The see-through bra did not obscure anything -- and her nipples were so hard they almost burst through the fabric. She stood there confidently, like she dressed like this plenty of times before, or more like the part she was playing that day: a call girl expecting her next john.

I was standing there, and completing the whole call girl at a brothel scene, she simply said, "Come in. You're right on time."

On time! She was playing her role perfectly. It did occur to me we didn't rehearse or plan any of this type of talk.

"Very nice, very nice", I said as I walked in as I continued to stare at her almost naked body. I closed the door, walked up to her, reached into my wallet, pulled out a twenty and started to hand it to her.

"That's for the window show.", I said.

And when she went to take the money, she kind of stopped, with a look that said we were crossing a line. Before, it was kind of a game. She would do something, and then she found the twenty I left. Here, she was taking money from her customer. She swallowed hard and simply said thanks.

Another line was crossed -- she took money directly for a sex act.

"No, it was a great window show! You deserve it. Now -- go stand over there." I pointed toward the middle of the living room, and I watched that great ass swing back and forth as she did what she was told.

I said, "Let me see if you cleaned yourself up." I could already see that there were no hairs poking out of the small panty triangle, but I wanted to see how far she went, She looked at me confused, and I just pointed to her pussy. She hesitated a bit, so I pulled out a twenty and waived it in the air. She took a deep breath, and pulled down her panties out from her stomach so I could look in. I walked over and peered in -- yep, clean as a whistle. I reached down with my hand to feel clean she was. As I reached in and felt her now bald pussy, she was as wet as she ever got. She was clearly turned on by this little game.

I pulled my hand out and grabbed another twenty. "Very nice. All clean!". I took the twenty and stuck it between the thong side string and her skin. She awkwardly smiled as now she was collecting money in more than her hand.

She stood there with her hands on her hips, her cheeks were flush, waiting for the next command. I look at her and then remembered what I asked her on the phone.

"Hey, where's my drink?" She looked at me and then I said, "You know, all the best brothels have drinks for their best customers!"

She kind of laughed, turned and went into the kitchen. Now, one thing about my ex was she was an ardent feminist. Telling a woman to fetch a drink for a man normally got you an argument.

But not now. Since she was being paid for service, she simply did what she was paid to do. Watching her turn and then seeing that great ass move with her cheeks swallowing the thong string was incredible. Back and forth, back and forth, all in rhythm with the click of her heels on the hardwood floors. Accenting all of this twenty stuck between the thong string moving in rhythm with her hips. It seemed she really was getting into serving her customer.

She walked back into the room with my drink, almost like a sexy waitress from a Vegas night club -- covered, but not with much. As she got closer, I wondered if I could ever get her to play nude waitress -maybe for me, maybe for others. But that would be another game.

She brought a scotch, handed to me and said, "Here's your drink, sir."

Sir! Sir? That was a bit unexpected. I guessed she was getting into being at someone's beck and call, or even she'd make more if she pleased the guy with the money!

"Thank you miss. Here you go", I said, and gave her another twenty. This time, she didn't hesitate to take the money. She took it and placed it in between the thong string and her hip on her other side -- so now she had twenties on both sides of her body. "Now, go into the other room and put on what you wore to school today. Keep these panties and shoes on. And leave the twenties wear they are!