Training Tracy

I needed a new pair of shoes. I'm a guy and so shopping isn't a hobby, more of a chore. I'd rather be hiking in the mountains than going to the mall. The only good thing about the mall is that it tends to be populated with lots of cute teenagers, dressed to look good to each other. I'm not going to pretend that I don't sometimes imagine how they look naked, even though it makes me feel a bit of a dirty old man.

Girls, especially young and inexperienced ones, have a hard time distinguishing which emotion they are feeling. Arousal, exhilaration, fear. Hunger, even. They are all a girl's body telling her...well, telling her something...but that's about all she knows. If you make it clear to a girl what you expect of her, and she is in that mixed up state where she is feeling some of those things, then she will often do what you want. Because it feels right at the time, even though later she will wonder what she was thinking.

I was in the shoe shop. I guessed the assistant helping me was probably a recent high school graduate. It was summer, so recent would mean just a couple of months earlier. She wore a nametag that told me her name was Tracy.

"Are you done with school, Tracy?" I asked her by way of conversation, when she came back from the stock room with a box of shoes my size. I have a rule always to talk to everyone, but especially pretty girls. And she was pretty. Long curly black hair. Maybe 5' 6" tall. Slim with a nice figure. Breasts nicely in proportion with everything else, a nice compromise between being flat-chested and having huge pillows spilling out. She was dressed in the uniform of the shop, an orange-colored shirt and a black skirt, short but not extremely so. Nice shoes, of course, since she worked in a shoe shop. Heels, but not insane ones.

"Yes," she said. "I just graduated high school in June."

"Are you going to college?"

"Yes, in October."

"Where will you go?"

She gave the name of a college on the other side of the country.

"That's a long way away. Do you have problems with your parents?"

She looked at me curiously. "No. Why?"

"Well, that's one reason that kids go to college far away. To escape their old life. Start a new life."

"I want to start a new life, I suppose. But I'm not running away from anything. Going to college just seems to be a big event although...well, I haven't done it yet, maybe it's just like more high school."

"I promise you that it's not like more high school."

"Good. I suppose high school was okay, but I was glad to get it over with."

She crouched down in front of me and got one of the shoes out of the box for me to try on. She had to maneuver herself carefully so that she kept her legs together and I didn't get a view right up her skirt.

I laughed. "They should let you wear pants," I said.

She laughed too. "Oh god, I wish. I'm so worried that...you know."

"I'll get to see up your skirt."

"Yeah."

"See your panties."

She blushed slightly and looked away. "Well...yes...although that's not a word I was expecting to hear out loud in the store."

"They are more fun to discuss than shoes. At least for guys."

She laughed. "Girls spend a lot more time talking about shoes."

"Do you ever discuss them?"

"Not really. Shoes, clothes. I suppose we do occasionally. Thong versus boyshorts. That kind of thing. How did you get me to talk about this?"

"So which did you pick?"

She looked confused. "What do you mean?"

"Thong? Or boyshorts?"

She blushed a little again, and looked away. She didn't say anything.

"Go and get the next size up in this model, these are too tight," I said. "When you come back and squat down to let me try them on, don't try so hard to be discreet. Let me see them."

"Oh my god." She looked around to see if anybody might have overheard me. "I can't believe you suggested that. We're in public."

"I know that. But I don't like to be boring. Talk about the weather. Or baseball."

"I'm not used to this. I don't know what to say. I know ‘red sky at night' and I know the Red Sox."

"Are they red?"

"What? The Red Sox?"

"No. You know what I mean."

"Really? I think I know. I just can't believe I'm having this conversation. I should go and get my manager."

"Don't do that. It's a yes or no question."

She looked around again, to make sure nobody could overhear us. Then she looked down at my shoes. so she didn't have to look me in the eye. "Yes," she said quietly.

"This is where you have to go back to the stockroom and pull yourself together. Then you have to come back. If you are adventurous, you do it in a way that at least gives me a chance."

She silently got up and went out through the door to the back room. In a couple of minutes she was back with a new shoe-box. She stood there silently in front of me. I could sense that she was breathing a little bit too hard, that the situation was getting to her. She was excited, or maybe scared. Certainly apprehensive.

"Red sky at night, buyer's delight," I said.

"You are...well, I'm totally out of my comfort zone even trying to carry on a conversation with you but...it's more fun than most days in this place."

"It's not for nothing that they made the guy in ‘Married with Children' work in a shoe store."

"I've seen a few episodes of that. It was on for a long time, from before I was born. It's weird if you see a late one then an early one. The kids grow up. Like Harry Potter, or Game of Thrones."

"You're growing up too."

"I know. I'm surprised when I see photos of myself when I was, like, 10."

"No boobs."

She looked up at me, blushing again. "Please don't do that. I don't even talk like this with my friends. Let alone at work."

"Okay. I'll behave. But I still want you to misbehave."

She opened the shoe box as if she was doing everything in slow motion. She took one shoe and then crouched down. At first her knees were glued together, and then, as if she'd suddenly made a decision, she crouched down the rest of the way quickly, letting her legs spread apart and giving me a brief sight of her panties. Red, as I already knew. She moved her legs together again as she picked up my foot. It had only been a split-second peek, but long enough for me to see what she had chosen that morning.

"Thank you," I said.

"I can't believe I did it. So not like me. Did you see? I don't even know if I showed anything."

"Briefs," I said.

"Oh my god, you did." She covered her face with her hands in mock embarrassment.

I laughed. "Briefs the same color as your face."

She used a shoehorn to put the shoe on. Then she put the other shoe on. They fitted perfectly.

"How do they feel?" she said, back in her professional demeanor again.

"Perfect," I said. "But I'm having such fun I don't want to leave yet. Maybe I should try one size larger to be sure?"

"I'm having fun too. Sort of. You are the most...I don't know...let's just say interesting, customer I've had."

"I can be even more interesting." I paused. "Take them off," I said firmly.

"What?" she gasped.

"Go back and get the next size up from the stock room. While you are in there, take them off and put them somewhere discreet."

"Oh gosh, I'm so confused. I don't think I could even if I wanted to."

"You do want to."

"I...I don't know what I want. You have me all mixed up now."

She took the shoes off my feet and put them back in the box. She took them back into the stock room. Soon she was back, with two boxes. The size that fitted and the next size up. She put the size that fitted on the seat beside me.

She squatted down, carefully keeping her legs together in the way she had practiced hundreds of times over the summer. I had no idea if she had been brave enough to take off her panties, but she was not yet brave enough to let me see for myself.

She took one shoe out of the box and put it on. Of course it was too large.

"I think these are too large," she said. We both knew that since the only reason I was trying them on at all had been to keep our conversation going.

"Did you do it?" I said.

"Yeah," she said. "I don't know why. You've indoctrinated me or something."

"It's exciting, isn't it?"

"It's insane. Way beyond exciting."

"You're going to do it for me," I said.

"I'll try. My body might refuse. Like a horse at a fence that is too high."

"Do you ride horses?"

"I used to."

"Now you ride your boyfriend."

She blushed. "Now you are going too far."

"Too far is just far enough."

At that moment, her supervisor came over, having seen that I had been there a long time. Tracy watched in terror as she approached

"Is there a problem, Tracy?" the supervisor said.

Tracy was still in state of confusion, unable to say anything. So I spoke instead.

"No," I said, holding up the box that was on the seat beside me. "I'm going to take this pair."

I knew the supervisor would be happy as long as a transaction was happening and I wasn't just wasting a lot of time.

Then, to my amazement, Tracy did it. While her supervisor stood there beside her, she got up in such a way that I got a glimpse up her skirt. I couldn't see that much in the shadows, but enough to tell she wasn't shaved. But not really much more than proof that she really was a girl. Not that I needed any proof. Then the glimpse was over and she was standing.

She took me over to the cashier. She was moving as if in a daze. I could sense that she was both excited and amazed at what she just did. The cashier asked me for my phone number and I reeled it off. Then I gave her my credit card. Soon I had a big plastic bag with a box of shoes in it.

I walked towards the door. When we were far enough away that we couldn't be overheard she spoke.

"They're in the box," she whispered. It took a moment for me to register what she meant. "It was the only place I could think of out of sight."

"Do you want them back?"

"Not now," she gasped. "Not in public."

"My number's in the computer. Do you have access to it?"

"Yes."

"When's your break?"

"In about half an hour if we don't get super-busy."

"Text me. I'll buy you a coffee. And give you them back."

"I suppose." She laughed. "It's going to feel pretty weird working until then."

"With a bare pussy."

"Behave," she hissed at me in a sort of stage whisper. But she was smiling. I doubt anyone had ever flirted so shamelessly with her before.

"You said you wanted to start a new life. It just started."

"I can't believe you got me to...you know."

"Take them off?"

"Yeah. And flash you. With my boss standing there."

"You'd better go back to work. I'll see you in a while and we'll see how your new life continues."

I turned and exited the shoe store into the mall. I wandered around looking in the store windows. I went into a stationery store and bought a large envelope. Then I went to the back of the store, where I was out of sight, got Tracy's panties out of the shoe box and put them in the envelope.

After about 15 minutes my phone vibrated. I looked at it. It was from what my phone considered an unknown number, but I knew was Tracy.

"break at 5pm" the text message said.

By then I'd scoped out the mall and found Starbucks. It seemed the best place to meet.

"i'll be in starbucks waiting for you"

"k"

"what coffee do you want?"

"latte. no sugar."

Coming up to 5pm I went to Starbucks and got us both a coffee. I had just sat down at a table when she arrived.

"I nearly didn't come," she said, as she sat down.

"Because it's scary as hell. You don't know who I am. You're bare and feeling vulnerable."

"Yeah, all of the above."

I pulled the envelope out of the plastic bag from the shoe store and put it on the table.

"They're inside," I said.

"Can I...?" her voice fell away.

"I won't be offended if you go to the restroom and put them on, if that's what you were going to ask."

"How can you read my mind? You know nothing about me."

She took the envelope and went off to the bathroom. In a few minutes she was back. Of course I couldn't see it, but I knew her pussy was covered with a layer of fabric. She sat down looking a lot more comfortable.

"It's a relief?" I asked.

"You have no idea."

"Tell me."

"Really? I'll try. So after you left it felt really weird. I mean it was weird when you were there but somehow you had my body all warmed up, so it seemed natural. Once I was cool, I felt guilty at what I'd done. If I felt a little worried before when I crouched down to put someone's shoes on, it was ten times worse like that. Plus every time I moved I was conscious of it...you know...down there.

"Your pussy?"

"You're so naughty, we're in Starbucks. But yes, every time I moved, it...you know..."

"Say the word."

"Oh gosh, you are so bad. Okay. Every time I moved my pussy reminded me it was uncovered."

"Does it want its new life to continue?"

"What? I don't know what you mean."

"Your pussy. Does it want to be adventurous?"

"Like what? It had an adventure today. There's more?"

"There can be."

"Like what?"

"That depends on what I decide."

A group of people came and sat at the next table, so we would be overheard.

"Let's go for a walk," I said, standing up.

The two of us left Starbucks and walked through the mall. I was tempted to put my arm around her but it would have been too much too soon.

"So what sort of adventure?" she asked.

"It will involve sexual stuff."

"I'm not an idiot. I realize that."

"Has your pussy had much?"

"What? Like s e xual stuff?"

"If it's going to be a good adventure, you have to be open with me."

She paused. "I'm not a virgin, if that's what you mean. But not much."

I guessed what she meant by that.

"You've only had sex a few times."

She laughed. "Well, if once counts as ‘a few'."

"Tell me."

"It's such a cliché. I lost my virginity on the night of the prom. I wasn't even that into the guy...enough to get it over with, but not enough to start a relationship."

"So you don't have a boyfriend at the moment."

"No, I've never had a real boyfriend. Are you going to be my boyfriend?"

"More of your personal trainer."

"Have you done this before?"

"Had sex?"

She punched me playfully. "No! Trained a teenager."

"Nope. It'll be an adventure for me too."

"So you're going to take control of me? Of my life?"

"Your new life started an hour ago. If you let me, I promise you will never want your old life back."

"Oh gosh, I can't decide if that's wonderful or terrifying."

"Maybe it's both. Girls can't really tell the difference."

"I'm scared. I don't know you. And I'm...well, let's just say I may not be a virgin, but I'm very inexperienced."

"Do you have a car?"

"Yes."

"What time do you finish work?"

"At 8pm today. Then I would normally drive home. My mom would make me dinner. Then sleep."

"No masturbation first?"

She looked at me, once again surprised at my directness. She blushed slightly.

"I'll take that as a yes," I said. "Tonight I will make you dinner. You won't need to masturbate. I'll do that for you. If your parents aren't going to make a big deal of it, you can sleep at my place. Else go home late."

"I'll try and tell my parents I'm staying with a friend."

"It will even be true. At least by morning."

"I suppose. I'm not sure you'll feel like a friend. More like the sergeant-major in one of those Army recruit movies."

"In the morning you decide whether to enlist."

"For basic training?"

"Yes."

"Gosh, my future hypothetical boyfriends will benefit if you get me tuned up like a NASCAR race-car."

I laughed. "I'm not sure I'm promising that. But you'll be ready for anything college will throw at you. Boyfriends. Hookups. Friends with benefits. Maybe a little girl-girl experimentation."

"Why me? Why are you picking me?"

"Mostly coincidence, I guess. I walked into your shoe store. You served me. But I noticed a special spark in you. It turned out you were indeed special. Not many girls would have done it."

"I guess you're only the second person to see it. Prom guy and you."

"Then it took even more courage than I realized for you to do it for me. I'll see it properly tonight."

"Properly?"

"More than a glance."

"It sounds odd, but I totes do want to show it to you. Not at all like prom guy."

"What was it like with him?"

"Embarrassing. I was so self-conscious. Girls all think we look weird down there, and nobody else had ever seen it. It took so much willpower to let him take my panties off."

"You already took them off for me this afternoon. You'll do it again tonight."

"I know." She pulled her phone out and checked the time. "I need to go back to work now."

We arranged the logistics. On the way home I went to the supermarket and bought the ingredients for dinner, and a bottle of good wine. And some condoms.

To be continued.

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