I have spent the last several years helping with my son’s “academic team” events. Most of the time it would be something like keeping score or reading questions. I have very much enjoyed it in its own right, but there has been one unexpected benefit. For as long as I can remember, I have had a “thing” for the smart girls. Between the team members, and some of the coaches even, I have been in heaven just being near them.

As luck would have it, one of the prettiest (and smartest) girls on the team qualified for an event at a college a couple hours away. We were all happy that she was getting the opportunity, but it was beginning to shape up that there wouldn’t be anyone to take her and the school wouldn’t allow her to go alone, even though she could drive herself and had her own transportation.

In a last ditch effort, the coach grabbed me one day and asked if I might be able to accompany Elly to the event. The school would have to sign off on it, but the coach, Elly’s parents, and Elly herself were fine with me being the one to take her. I would have to rearrange my schedule for a couple of days, but the opportunity to spend a number of hours around Elly was worth the effort, so I agreed.

Everything worked out and the trip was arranged. We would leave on a Thursday afternoon, spend the night near the college and Elly would participate in the event all day Friday. After she was done we would drive straight home. The lodging and expense money was even being provided, so all I really had to do was be there and drive.

The day before we left, the coach asked me to come to his office for a quick meeting. He closed the door behind us and handed me a smallish black duffel bag. He sat across from me and cleared his throat before speaking.

“I thought I should prepare you for the fact that Elly has a very particular routine that she insists on adhering to before every team event or competition. She has made it clear that this event will not be an exception. I would rather not discuss the particulars of the routine, but suffice it to say it is outside what would normally be expected from a teacher or chaperone.”

I raised one eyebrow and began to respond “Wha...”

“Again, I would prefer to not give you any details, but unless I am very wrong, you won’t be asked to do anything you wouldn’t want to do. If you find you can’t follow through, I have no doubts that Elly would pull out of the event. That would be disappointing, but not the end of the world.”

I sat in silence for a second considering what it could possibly be. I looked at the bag in my hand and reached for the zipper. The coach stopped me.

“Elly is very particular that this bag not be opened unless she is present.”

I let the bag fall in my lap. I considered my options. I couldn’t believe that Elly’s routine could be anything too outrageous and again, just the fact that I would spend multiple hours with someone I very much enjoyed looking at and being around would make nearly anything worth it. I had already taken the time off, so I agreed to the new conditions. I must admit, I was very curious about what was to come.

The next day I pulled up to the school about an hour before the normal dismissal time. Elly was excused a bit early to make the trip. I had packed my own overnight bag and brought the, still unopened, black duffel with me. I will freely admit that I was very curious about the contents of the bag. It wasn’t heavy. There were only a few objects inside, but no amount of feeling or shaking revealed what it could be.

Elly had two bags with her. A small soft-sided suitcase that apparently contained the things she needed to stay overnight, and a backpack that looked like it probably contained her school books and laptop. I opened the trunk and she dropped her bags next to mine, making no comment about the black duffel, or anything else really.

We got in the car and I asked if she wanted to stop and get some snacks for the trip before we left. She shook her head slightly to indicate that she didn’t.

“Well, off we go then.”, I said.

I put the car in drive and pulled away from the school. Elly was silent the entire way. She spent most of the time looking at her phone and I divided the time between looking at the road and sneaking glimpses of Elly’s legs.

She was wearing a white hooded sweatshirt, but also a nicely short plaid skirt that ended just above her knees and showed a generous amount of that smooth tan skin that I am very fond of.

We were silent, but not really awkwardly so. When I drive, I don’t mind just riding along, listening to the radio and thinking. She didn’t seem to want to chat, and I sure wasn’t going to try to make her.

We arrived at the hotel and parked after I checked in. She grabbed her two bags from the trunk and waited for me to grab my bag and the duffel and we proceeded to the room. They had booked us a double queen room (two queen beds). The fact that we were in the same room didn’t escape me, but the fact that she would have her own bed would preclude any “accidental” touching or other shenanigans.

She put her bags on the bed closest to the bathroom and I put mine on the other bed. We decided to order pizza for supper and I made the call.

I tossed the TV remote to Elly and let her choose something to watch while we waited for the pizza and drinks. They arrived and we ate while we watched TV.

So far, I didn’t see anything particularly unusual about her routine. She was pretty quiet, but some people are just like that.

After she was done eating she wiped her hands on a napkin and acknowledged the existence of the black duffel for the first time. She picked it up and examined the tab of the zipper. I’m not sure what she was looking for, but she was apparently satisfied and unzipped the bag.

She pulled out a single piece of printer paper out of the bag, being careful not to show the other contents. She handed me the paper.

“Read.” she commanded, quietly then took the black bag and another small bag from her own suitcase to the bathroom. I heard the shower start shortly after she closed the door.

The page was filled on one side with text. I sat on the bed and read the letter.

To Elly’s Chaperone:

Thank you for taking the time to act in this capacity. We understand that this is very unusual, but hope that you will understand and be able to perform the actions that will be asked of you. Elly would prefer that we not tell you exactly what will transpire, but suffice it to say sexual contact between you and Elly will be required. We are fully aware of the “routine” and you may be assured that you will be taking any actions she commands with our full approval and blessing.

As you are reading this letter Elly is in the shower. When she is done, she will summon you. Please enter the bathroom. Elly will instruct you from that point.

The letter was signed by both of Elly’s parents and the coach.

To say I was shocked was an understatement. The fact that they sent me here fully expecting (demanding even) that I have “sexual contact” with Elly was blowing my mind. I sat in silence and considered the possibilities.

After about 30 minutes, the bathroom door cracked open and Elly said “Come.”

With very little hesitation, I rose to my feet and moved to the bathroom door. Wisps of steam curled around the edge of the door as I slowly pulled it open before entering.

Elly was standing near the shower (which was still running) completely nude. Her wet hair hung over her shoulders and she “posed” to allow the full effect of seeing her nude for the first time to wash over me. I would like to say I was discreet and enjoyed the view of her naked body with the respect and modesty that the difference in our ages should dictate. In truth, I ogled her without any decorum. For the first time, a small smile curled the corners of her mouth as my appreciation of the view met with her approval.

After allowing me a few seconds to admire the view, she turned and pulled a purple nitrile glove out of the bag (that was sitting on the bathroom counter) and instructed me to put it on my dominant hand (right in my case). The humidity of the room made it a bit of a struggle, but I finally got it on.

She reached into the bag again and pulled out an unopened tube of KY jelly. She opened it then grabbed my gloved hand before squirting a generous amount of the cool gel on my first two fingers.

She smoothed the gel around a bit, then hopped up to sit on the bathroom counter. She pulled her heels up and perched them on the edge near the delightful cheeks of her ass. She let her knees fall apart and I saw the delicate, and completely shaved, lips of her pussy open.

She indicated I should make a “gun” shape with my first two fingers extended and the third and fourth folded toward my palm. She took my hand and guided it between her legs. She rubbed my lubricated fingers around her pussy then pushed them toward the opening, sinking them fully to her depths. Her eyes were closed and she sighed a bit at the penetration. I started to move them around a bit, but she stopped me. “Let me do it.”

I allowed her to provide all the motion as she slowly slid my two fingers into her depths and out for at least 5 minutes. She pulled my fingers out and pulled the glove off my hand, throwing it in the trash can next to the toilet.

“Undress.” she commanded.

I stepped back with just a little hesitation and pulled my clothes off, throwing them on the floor outside the bathroom door.

While I was undressing, she had reached into the bag without opening her eyes and extracted a condom packet. She was opening it as I approached her again. She gently took my erect cock in her hand and slowly rolled the condom down its length. She again applied KY jelly over the latex and smoothed it around before pulling me toward her waiting opening.