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This is based on true experience my senior year in high school with some added for spice.

Part 1 – The Swim Meet

As a senior in high school, I should have been thinking about a lot of things; the upcoming state soccer championship, upcoming college acceptance notifications, of course then finding a way to pay for college, and generally just not fucking up in my final two semesters.

But here I was on a Tuesday night in the bleachers of a humid dank swimming pool for the Trojans final swimming meet before the states. I didn’t swim competitively, never had. None of my buds were with me, just me and a few other die-hards and of course the parents. I was alone with my obsession. Only thinking about that beautiful creature by the pool, just as I had been for the last three months.

There she was, Jackie, clowning with her teammates, particularly the ones with the big cocks barely hidden in their loose skimpy speedos. She was a thing of beauty, and I just couldn’t get my mind off her, or even think clearly anymore. Not that she even knew who I was.

She had deep brown eyes framed with a pixy’ish brown mane on her 5 11′ frame. Being the same height as me, her eyes pierced right through me when I had the temerity look her in the eyes as we occasionally passed in the hallways between classes, me maybe mumbling a barely audible “hello”.

It was clear she knew her power as she skittered around the pool side, displaying the flawless strong feminine body of a champion swimmer, with those long but shapely legs leading to an ass tightly displayed in her racing suit. Of course, a sleek abdomen sculpted by training leading up to a perfect set of pert breasts protruding, nipples accentuated by the chill. And her smile, even though never directed at me, melted any forbearance or concentration I could muster.

Everyone understood that the swim team was an experienced group, as in they were ahead of the rest of us in exploring the opposite sex. Co-ed, traveling together, spending half the time essentially naked in their form fitting swimsuits. It was inevitable. They were too cool to brag or even talk about, kinda like fight club, first rule of fight club: nobody speaks about. And me, as a virgin, this made any thought of approaching her even more intimidating.

So here I was enraptured at a distance watching Jackie flirt and grab before her upcoming swim heat. The time came, the starting gun went off, she dove and swam beautifully placing a close second. Now I could leave. I had my excuse to speak to her tomorrow, to congratulate her on her race. Time for bed. Of course, little sleep. I would just be lying there jerking my little dick with her image in my head and thinking what I would say to her tomorrow. Pathetic.

Part 2 — A Hello

Jackie was in my 10am history class. She sat with her swim team girlfriends, I sat with my soccer and math buddies. Yes, I was also a bit of a science nerd.

I got to class early knowing she would arrive after and then I could say hello when she came in. My hands were getting a bit sweaty as I waited. Then she came in chatting with Hallie and Susan from the team. I started to get up, and then sat back down hoping no one notice. Chickened out.

As class droned on, I committed to making the move. No chickening out. Yes, no matter what I would say hello when class ended.

Bell rang, Jackie stood up, Hallie and Susan rushed out together leaving Jackie to leave alone.

As she was passing my desk, I stood and said “Hey Jackie, nice race last night. Congratulations”

She looked at me and said “Oh Hi Sam.”

Geez, she knew my name.

I said, “Yeah, I saw you at the meet last night.”

“You did, what brought you there?” She look a little quizzically, but I thought maybe a there was something mischievous in the smile. Probably not.

“Oh, a I guess I wanted to cheer on team, you know. You guys have done great this season. And nice job with getting second place.”

“Yeh. No. Second place sucks. On top, ruling the roost or its just better not to show up. That my way. But thanks for coming anyway.”

My heart went flat. Again, saying the wrong thing as she turned away.

But then she turned back. “Hey Sam, on Saturday night Brad is having a big party at his house to celebrate the end of the season. See you there maybe?”

“I don’t think I am invited”

“I just invited you, didn’t I? You were at the meet, so. In fact – didn’t you come to a number of the meets.”

“Yeah, almost all of them I guess.”

“You did? That’s cute. Weird maybe, but cute. So I’ll see you Saturday night?”

“You bet, Miss”

Again, the same look as she turned away.

Bang, my head was spinning. What just happened? Jackie invited me to a party? How did that happen? And she had noticed me, I guess. Wow.

But “Miss”. Why did I say “Miss”?!? That sounded stupid. Where dd that come from? I sure hoped she hadn’t noticed.

Part 3 – Saturday Night

I was a wreck the rest of the week thinking about Saturday. What to wear? What would I do if I saw her there? None of my istanbul travesti friends were invited I wouldn’t feel right bringing someone to crash it, given Jackie sort of invited just me to someone else’s party.

Saturday, I headed alone to the party at 930, even though it supposedly started at 8. People would be drunk by then, no one would be keeping track who was coming and going. I barely knew Brad, and he always impressed me as an asshole.

Lots of cars parked in street. Loud music made the house easy to find. Folks milling around in front on lawn and heard a splash in back, must be a pool.

I had on jeans, sneakers and valor maroon shirt (a thing back then, and my only shirts non-oxford or polos). I tried to blend in as I approached, and walk like I belonged and look confident. Unfortunately, my legs being slightly shaky didn’t really get it done and I was perspiring a little too.

As I approached I hear someone yell “Hey you”. I turned to see Brad pointing my way. Now I am sure I will be kicked out before I even arrive.

“Hey Sam” Brad says. “Jackie asked if I had seen you a while back.”

“Thanks” I say.

“Yeah, you may want to find her. You know how she gets.”

“No, what do you mean?”

“Never mind, just kidding. But she did ask.” Brad said as he turned to hi five one of his swimming buddies.

I wandered around looking for a beer, trying to look busy and directed. I didn’t really know anyone at the party. Suddenly a little tug on my shirt.

“Hi there, nice shirt”. I hear Jackie’s voice. “I thought I saw that in the girls department at Target.”

“No! This was from Bloomingdales. Definitely men’s.”

“Well, Hi to you too Sam”

“Oh sorry. Its just you know. But, Hi Jackie”.

“Did you just get here?”

“Yes, I had another party before this” lying for no reason. Good way to start.

“Well, want to grab me a beer? I was sitting around the other side of that bush. Meet me there?”

“Sure, I will be right there.”

Wow. This was feeling like the Twilight Zone. Had Jackie really been waiting for me to arrive?

Two beers in hand I walked around the bush off to the side in the back yards, quite, dark and away from the hub-bub.

There was Jackie sitting on a small bench in her short brown leather skirt, with a white peasant blouse with the top half unbuttoned. Literally breathtaking.

“Hey, here’s your beer. They’re a little warm I guess”

“Thanks Sam, why don’t you sit here”. As she skootched over to make room.

I sat down took a sip, and said “Nice party”

She looked at me, right in the eye with that same mischievous expression and said nothing. She just looked and was silent. Our faces were only about 8 inches apart. So I slide a little bit away and looked toward the yard, “Everyone seems to be having a good time”.

Still, she just sat there looking at me saying nothing.

I made one more attempt at conversation. “I like your hair do, very cool”

She remained silent.

I thought, should I kiss her? What if she doesn’t want me to? Maybe I should get another beer and come back.

She said nothing.

Then, finally she said “Sam, you’re a virgin right”

“Yes Miss”.

There it was again, saying Miss. So stupid.

“You haven’t even ever had a blow-job have you?”

Now this was getting a bit weird. The directness left me not knowing how to answer.

“Don’t bother answering, I can guess.”

Feeling nervous and humiliated I started to get up to leave.

“Sit”

I looked at her eyes. Clearly that wasn’t a question.

“Yes, Miss”. Now it felt strangely natural to say, or at least fitting.

“I am going to ask you some questions now Sam. I need you to be honest. Understood.”

“Yes Miss.”

“Good, and understand dishonesty will have consequences. Understood?”

“Yes, Miss.”

“Good, first question: Did you really go to a party before this?”

“No Miss”.

“OK. Good job being honest now. But you deserve some consequences for the previous lie. Don’t you agree?”

“What consequences Miss?”

She was silent.

Finally, not knowing what else to do, I said “Yes Miss. I agree.”

“Good boy”. Her saying that made me feel inexplicitly good and sort of tingly.

Then she said. “Now. Do you want to kiss me?”

“More than anything in the world Miss”

“Why didn’t you before?” She sort of chuckled

“I don’t know. I was scared I guess”

“Well, would it be better if I told you what I wanted and then you just do it?” with a new sternness in her voice.

“That would be so much better, Miss”

“Good. Let’s start. Unzip your pants, pull them to your knees … and underpants.”

“Really, now. Here?”

“You know the other thing with consequences? Questioning a directive.”

“Yes Miss”. I gingerly complied. Sitting my naked ass on the cold bench with my pants at my knees. My wiener had shrunk to nothing.

She looked at my lap, and then in my eyes and said slowly and firmly “Well my next question was going to be ‘Do you want to fuck me?’ but travesti istanbul clearly there is no point. That is an embarrassment, not a dick”

I was quivering, feeling humiliated and wanting to cry. I started to pull my pants back. She stopped my placing her warm hand on my crotch, and looked at me again in the eyes and said “kiss me”.

I did. Proverbial fireworks went off. And now I did start to sob, just a little.

She said in a warm tone of voice, almost maternal “That’s OK. There, there. You can make me happy other ways if you are willing to serve without question. Would you like to do that? Become my submissive?”

I had never heard that term, but it sounded good. Maybe great, so long as I could kiss her.

“Yes Miss. I would very much like to be your submissive.”

“Good boy. We will start Tuesday formally if you agree to the terms. I will hand you the rules on a note in history class on Monday. You will have Monday night to decide”

“Miss, I know I want to serve you. I can tell you now.”

“No. It is important you understand the rules and fully agree before committing. But we will end tonight with the consequences you earned earlier. Now get up and lay across my lap.”

“What here? Across your lap? What are you going to do?”

“Yes, here. Yes, a spanking. No one can see around the bush, and no one will come around unless you make noise. Unless of course some bad luck. Here why don’t you put these in your mouth before you lay across.”

She reached down, pulled up her skirt to access her panties, pulled them down here beautiful legs and over her feet and handed them to me.

They were very damp and smelled like heaven. She nodded knowingly. I put them in my mouth and lay over her beautiful legs. She pulled my hips up slightly so my ass was fully prone and my dick which had hardened rested where her thighs met, not long enough to go in between.

She then proceeded to spank me with her hand, every once in a while stopping to run her fingers over my ass event touching my crack. Then she would continue.

Everything just kind of went spinning and fuzzy overwhelmed by the situation. At some point she stopped. Lifted me off her lap. She got up, straightened her skirt and walked off without a word.

I lay there for a moment trying to figure out what just happened. Realizing I was exposed, hurriedly pulled up my pants and quickly passed through the party trying to leave without being noticed, her panties tucked in my pocket.

Just as I was heading toward my car, I hear Brad yell out. “Hey Sam, what did I tell you about making Jackie wait.” He just smirked and turned away.

Part 4 — Monday

I hardly slept Sunday night wondering what Jackie and history class would bring. I really felt that I was losing my mind, or at least any control of it.

The only communication I had had with Jackie since Saturday night was a brief text exchange. Somehow, she gotten my cell number.

Sunday morning I received a message saying:

Hi — Jackie here. Do you still have my panties?

Me: Yes. I have them safe and sound. How are you?

Jackie: Do you still want to move forward with my proposal?

Me: Yes Jackie. Very much. But I think we should talk about what happened.

Jackie: I am glad to hear you want to take the next step. Tomorrow, wear my panties to school. In History class leave your fly open. Sit on my side of the class and be there before I arrive. See you then.

Me: But Jackie, you want me to wear your panties to school, really?

And then silence. No more response.

Now it was Monday morning, and I am sitting on the bed with Jackie’s pink silky panties next to me trying to figure out what to do.

Do I go down this path? Wearing girl’s panties to school? If anyone found out I would be laughed out of the entire place. But really, I didn’t have a choice. My willpower was owned by Jackie.

I showered and then slipped them on.

Oh, they felt wonderful. I started to get an erection. I put my regular jockey shorts in my backpack so I could change in the bathroom before gym class and soccer practice.

Bicycling to school, it felt like everyone knew my secret. They knew I was wearing Jackie’s panties and that she had spanked me silly on Saturday night. Where was this going to end.

As I got off my bike, I realized riding had given me a serious boner. Lucky due to my dicks size it wasn’t super obvious, but still I had to keep my hands in my pocket to be sure no one noticed. With my hands in there I found it very hard to resist rubbing the fabric against my penis. It just felt so good. After my first class before heading to History class I needed to pee. I decided to sit in a stall so as to avoid any chance of anyone catching a glimpse of my panties, I mean Jackie’s panties of course.

As I sat down and lowered my trousers, I could see a damp spot in the center front. A little precum must have leaked. So embarrassing. And I was about to see Jackie with my fly open.

I took some toilet paper to try to dry away the seamen. Mostly it worked, istanbul travestileri but still a little stain on the delicate pink fabric.

Now I had to hurry to ensure I was in class early, before Jackie and her crew arrived.

I entered the class and sat in one of the seats Jackie’s posse usually sat in and waited.

Soon people started to steam into class. Finally, with just a few minutes before the starting bell, Jackie walked in, walked over to where I was sitting and said in a loud voice “Oh Sam what are you doing over here in the girl’s section? That precious. Let me sit next to you, girlfriend”.

She plopped down in the seat next to me. I was beat red, blushing like a five-alarm fire.

The class bell rang and as everyone was looking at Mr. Smith as he started class, I felt a hand brush against my crotch. I look down and there was Jackie’s hand with a note in it working its way into my open fly. She felt around a bit, and I guess satisfied I had complied wedge the note inside and gave my fly zipper a quick yank closed. She gave me that patented smile and bent over toward my ear whispering “good boy”.

I was so happy and satisfied, I could have died and gone to heaven right then and there.

As the euphoria receded, I realized this was just another step along an intoxicating and dangerous path. I knew I had no control to turn back.

As class ended, just as she had on Saturday night, Jackie stood up and didn’t say another word as she walked out of the room other than a quick look back at me with her cute red lips slightly puckered. She had a pencil skirt on that profiled her sculpted ass as she sashayed away which I could see the eyes of other guys in the class follow out the door.

Again, I was erect with my pany clad dick and a paper note trapped behind my half closed zipper. I reached down and discretely pulled my fly shut and stood slowly with my book hiding my erection. I walked quickly to my next class practically holding my breath until lunch break.

When lunch break finally arrived I was desperate to fish Jackie’s note out of my pants and read her proposed “terms of submission”. Actually, I guess they weren’t proposed; she had been pretty clear they were “take it or leave it”. Knowing I was inevitably going to “take it”, I was very nervous what lay ahead.

I found a quiet corner in the courtyard where I sat down, looking around nervously to see if anyone noticed me. On the bench I sat down and extracted the note. It was on pink paper, pretty closely matched my panties and it smelled strongly of an expensive and rather strong perfume.

I unfolded and read the purple ink in flowing script:

Dear Samuel –

Please read my requirements for me to allow you to serve me and be my submissive.

If you agree to these terms, return this note to me in class tomorrow signed “Mistress Jackie – I promise to serve you and follow your rules submissively – Panty Boy”. Yes, Pany Boy will be how I address you going forward. In public I will call you PB. You can explain that nickname to others however you want, unless of course I direct you to tell them the truth 🙂

If you want to stop, then bring my panties to class tomorrow hand cleaned and dried. Hand them to me and I will never acknowledge you again.

RULES:

You will address me as Mistress. If we are with others you can use Miss

You will do whatever I ask without question. You are allowed to ask for clarification

You will always be truthful

You will not cum or touch yourself without my permission

Every morning and evening you will send a text saying “Mistress – thank you for letting me serve you”

I hope you make the right decision. I do so want to play with you beautiful ass.

Mistress

After reading, I was relieved. I could do all that. Easy. This was going to be a lot of fun.

Part 5 – The Beginning

That night I didn’t jerk off, though I so so wanted to. I wasn’t sure whether it already started, but I really wanted to be a good boy for Mistress.

The next morning I bounded out of bed and got ready for school. Mistresses’ panties safely tucked away in my sock drawer and off to school.

I walked into History class and took the same seat as yesterday. Jackie walked in wearing black yoga pants and tee shirt not fully covering her washboard mid-drift. She sat down next to me and just looked me in the eyes. I handed her the perfumed note.

“Thank you PB. I am glad you made the right choice.”

“Thank you Miss”.

Saying that with all these people around felt weird, embarrassing, but also kind of good. Her two friends, Hallie and Susan, sitting next to Mistress heard the exchange and smiled at me.

I thought, “I wonder if they know anything”

As class proceeded, Mistress slipped her hand towards my pants like yesterday but bumped into my closed fly. She gave me a scowl and leaned over whispering “never let there be a barrier between my hand and your panties again”.

I was flummoxed. That wasn’t a rule on the note. And I didn’t have panties on, she didn’t tell me.

I leaned over to say something. Suddenly a pain shot through my groin. She had found a way to grab my balls through my pants without visibly moving her arms. She quietly snarled “never speak to me during class, only I speak to you”.

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