Flagpole of Humiliation

I was on my way to the dorm in my car. The night before, my wife told me that she'd finally had enough with our college babysitter, Chloe, and I was supposed to bring her final check to her in her dorm and give her the bad news.

I really couldn't argue with the decision, because she was truly a horrible babysitter. She rarely came on time, was doing social media on her phone most of the time when she was there and generally had a bad attitude.

On the other hand, I was disappointed because, as a 40 year old man, I had really enjoyed watching a college girl walk around the house in her tight outfits. She was a brunette with shoulder length hair, had a great figure and loved wearing those super short shorts that young girls wear these days which showed her firm and perfect 18 year old ass, and also liked tight-fitting crop tops that showed off her toned stomach and size C tits. I loved to catch glances of her as she walked around the house, and had spent countless sessions in private pleasuring myself to her facebook and instagram pages.

Oh well, I thought to myself. I parked behind her dorm, grabbed the check and went up.

I'd called ahead to Chloe to let her know I was on the way over but didn't tell her why. When I told her I was coming, she paused for a bit and just said "I see. Ok." I thought it was odd she didn't ask why, but didn't think anything of it.

When i got to her room on the second floor I knocked and she opened the door. She was wearing tight yoga pants with heels, and a tight white t shirt that was tied in the front right under her breasts, showing off her stomach and her butterfly tattoo right above her ass. My eyes instinctively went down because I didn't want to give the impression I was staring, but I could already feel my cock start to swell a bit as it usually did around her.

She gave a small smile out of the corner of her mouth and tilted her head, looking at me and just said "Hi." Then she turned and walked back into her room, leaving the door open. I followed her into the room, and the door swung shut behind me automatically.

It was a typical girls college dorm room, with everything mostly pink and white in color.

Chloe had gone back to her desk chair and sat in it leaning back with her legs crossed, looking up at me and dangling her leg. I was just standing in the middle of the room holding the envelope, and wondered why it felt like she had all the confidence and power at that moment.

I started in "So Chloe the reason I came here was because we really don't think you're working out for us." I went on to explain all the things she'd been doing wrong, but finding it hard to make eye contact with her, while she just stared straight at me from the chair with a slight smirk.

While I was speaking and looking around the room, i noticed her dresser drawer behind her was open, and I could see some pink cotton panties and a white cotton bra inside. I tried not to focus on them, but I could tell she noticed me looking and she slowly turned to look at them before turning back to me.

Finally, she stood up and walked toward me and stood inches from me, looking up at me, as she was several inches shorter.

"So you think you came here to fire me?" She said softly and sarcastically. Because i'd never stood that close to her face to face I wasn't sure how to react or what to do, but was only aware of her direct gaze. "And is this envelope supposed to be my last check?"

"Umm...Y-y-yes..." I said, lifting it up towards her.

Suddenly, in a smooth motion, she looped a rope around my wrists and pulled it tight, before I could get my senses as to what was going on. It was like everything was going in slow motion, but I couldn't move. She threw the other end of the rope up over a hook on the ceiling and pulled up, so that my tied hands went above my head. She pulled up until i was on my tippy toes, and tied the rope off on her desk leg.

"Chloe!" I finally shouted out. "What are you doing? Let me down right now!" I was wriggling against the ropes and started to kick my legs.

She just stood back looking at me and said "There's university police right outside the building. If you don't stop moving, I'll just start shouting that you're attacking me. How about that?"

With that I stopped moving immediately, and just stayed there, hanging with my arms above my head and standing on my toes.

"That's better" she said, "now we can start." She quickly undid my belt and pants, pulling them completely off and leaving my bottom half completely naked in front of her. I started to shout and kick but she put up a finger to her mouth with a stern look and i stopped.

She stood for a moment looking at my cock, which was still mostly soft but which I could feel swelling a bit from her stare.

"Well, well, well," she said, "about as average as I thought." She took a finger and flicked the tip of my cock before walking to her desk.

"Now, did you really think i don't know how you stare at me? Or how you check out my online pics? Oh, you really thought you were hiding that?" She started laughing. "I guess you didn't know you left your computer on after one of your little "sessions". So I got to see very clearly which of my pics you liked. Based on how many of my pics you saved to your hard drive, you must spend most of your free time jacking off to me. Right? And funny how the porn vids you download all seem to have girls that look like me."

I was too horrified to even respond because she was entirely right. She'd caught me red handed. And I was totally captive in any event.

She flipped on her computer screen and continued "As I recall, you like this one because you even cropped it to make it bigger!" She brought up a picture of her in her dorm wearing a super tight low cut white tank top that had a clearly visible red lace bra underneath, with shiny tight red booty shorts that were cut high to show the bottom of her ass cheeks.

"You liked this one, huh?" She asked, looking at me. "What about it did you like?"

I was silent, trying not to look at either her or the picture.

"Hey!" She said, "I'm talking to you! Or should I open the window and yell for security? Why bother resisting? We both clearly know you jack off to me, so just tell me."

Reluctantly, I started talking, "I... I like the way your shirt is really tight against your . . . your breasts . . . And how I can see the lace outline of your bra underneath pressed up against the shirt. And how your shorts show off your butt shape and butt cheeks."

As I was describing this to her and looking at the picture, my cock started to rise despite my attempts to prevent it. Looking at her pics always made me helpless, and this was no exception. Her body was so young and hot, and her face so pretty, I just couldn't resist it. She stood silently in front of me, smirking as she watched my cock twitch by itself to a full erection as I described it.

"Well, well, well," she said, "I guess I really do have control over you."

She pulled out her phone and snapped a picture of me, standing there tied up and helpless in the middle of her dorm room, naked with a full erection.

"Chloe, please don't!" I pleaded with her, "I won't fire you. I'll do whatever you want. Please!"

She looked at me and laughed "I don't want your stupid job. I hate working. What I want is for you to admit that I totally own you and your cock. That your cock belongs to me. And I want you, a 40 year old man, to beg me, a young college girl less than half your age, to beg me to let you cum. That will be my amusement for the day."

I decided that this had to stop. "Chloe, that will just never happen. Let me go!"

She just smiled. "It'll never happen? We'll see."

She started recording video on her phone and put it on her desk, pointed at me. Then she turned to her dresser drawer and took out the pair of pink panties I'd seen before. She dangled them with a finger and slowly started lightly brushing my cock with them, back and forth, up and down. The sensation of her panties lightly touching my cock immediately brought me back to full erection.

"You just have no control, huh?" she mocked, "Your cock just can't help but give you away."

Then she took the panties and hung them off the very tip of my cock by one of the panty leg holes. My cock started twitching to the feel of the panty fabric on my tip, making the panties bounce up and down.

Chloe looked and laughed. "Look at that! So cute! Your little cock is dancing!"

"Chloe," I said, as my cock continued to bounce her panties up and down, "Please . . . Please stop."

"I don't think so," she replied. "You what I call this," she asked, pointing at my hard cock holding up her panties, "I call it 'the flag pole of humiliation'. Get it? Your little dick is the flag pole and my panties are the flag that shows I've humiliated you. If you could control your erection I couldn't do this, right? The panties would just fall to the floor. But here you are, dick up in the air, holding up my panties. How humiliated do you feel?"

"So," she continued, "Do you admit I completely control you?"

I was silent. She walked up to me and pressed against me from the side. I could feel her firm breasts pressing against my arm, and the smooth fabric of her yoga pants against my skin as she straddled me from the side.

"I didn't hear you," she said, sliding her leg up and down my leg, hitting my cock with her knee. "Let me hear you say you're being completely controlled by a little college girl."

She then took the panties and looped them around my shaft, and then started ever so softly stroking me with them. "I own you," she whispered. "I know what your weaknesses are. Young college girls. Yoga pants, tights, halter tops, lace bras, cotton panties. Right? Just like in the pictures. Just like that picture of me on the computer. Admit it." She tightened her grip around my cock ever so slightly as she continued to stroke me. I could feel the cum pulsing near the tip of my cock and knew I would not be able to last. She could feel me shudder and she knew it also.

"There it is," she said with a soft smile, "I've got you, don't I?"

I had no choice. She was in complete control.

"Yes," I whispered.

"Yes, what?"

"Yes, you're in complete control."

"What else?" Her stroking was slowly increasing in speed. "Or should I just stop now like you asked before?"

The cum was pounding against the inside tip of my cock, but she knew just when to let up a little to prevent me from busting.

"Yes," I said, "college girls wearing tights and yoga pants, with halter tops and visible bras are my weakness. Cotton panties are my weakness. You are my weakness."

"You own me," I said, "you own my cock. It belongs to you." I had totally given in to her. All I could think about was cumming. "I'm no match for you."

I was just about to spurt and she abruptly stopped again. My entire cock was throbbing with cum. "Unnnhngh," I cried out, "Please Chloe, please don't stop."

"Beg for it" she said sternly.

"Please, please, I beg you Chloe, please let me cum."

She stroked me twice more and stopped again. It was excruciating.

"Please Chloe. I beg you," I said again, and just started pathetically imploring her with whatever came out of my mouth, "I'm at your mercy. I'll do anything for you. Please put me out of my misery. I completely belong to you. I'm being dominated and humiliated by a young college girl. Please, please let me cum my college mistress Chloe, please!"

"That's more like it," she said, and with that delivered her final swift strokes to my aching cock that sent my cum spurting into her hand and panties. My body went totally limp with physical and mental exhaustion. She left the sticky cum soaked panties wrapped around my cock. She undid the rope, then took my pants and threw them at my feet.

"Put your pants back on, but leave my panties around your cock," she said, and I slowly obeyed.

She went to her phone that had been recording what happened and held it up. "Now that we understand each other, whenever I text you, you will come immediately to me. Is that clear?"

"Yes Chloe, it's clear." I murmured, and slowly walked out of her dorm room, wondering what would happen next.