I had been looking forward to this trip for some time. It was a contest, and only later I discovered the true purpose and origin of the trip. I had won it at the college I attended in Northwest Missouri. It would take me to Kansas City, to St. Louis, and the final destination in Chicago. Roundtrip. By train. With a one day layover in each of the three cities.
I had planned to use the layover in each city to workout with some peers. Racquetball with Tim in Kansas City. Games at the Jewish Community Center in St Louis. Finally a visit to the Chicago Athletic Club in Chicago. A good summer tuneup for the fall season.
Happy to get out of Maryville, Missouri for a little while. My college crush had been weighing on my mind, and I needed to muster the courage to ask her out. It was high time as a sophomore, and she had been dropping hints as subtly as atom bombs.
I picked up the train in Omaha at 5:00 am in the morning on the way to Kansas City. It was a nice sleeper car with a sunny view. I took a short nap and woke up for a late breakfast. Afterwards, I planned on departing the train for the layover. I was excited about going to the club. Then my plans were changed. For a long long time.
I went out in the dining car and sat down for a good breakfast. I noticed a lady above sitting at a table two tables away from me. We made eye contact, she smiled, and immediately she walked over and sat down. We began chatting. She introduced herself as Isabella. We talked, and after a few minutes, she asked, "do you recognize me Zack?"
I demurred, stating to her that she did resemble someone i knew, but also that it was just a coincidence. We chatted a little longer, and I got up and bid her adieu, commenting that i was disembarking for the layover in Kansas City.
When i arrived back at my train compartment and entered, i turned and noticed she had brazenly followed me into my private trainspace. I started to question her presence but she interrupted me, almost shouting, "you're not going anywhere!" I looked at her incredulously, and became even more confused as Isabella grabbed my wrist and pulled it behind my back. I had had enough, and then she yelled for me to stop. It sort of froze me for a couple of seconds, and then in an even more bizarre twist, she pinned my wrists behind my back and locked them. Cuffed them. She had obviously practiced this through. We both sort of fell back onto the sleeping mattress in my traincar. This was too much. I stood up, but almost as quickly, sat down as Isabella put her hands on my thighs and pushed down. "Again Zack, you are not going anywhere. You are here to learn." This was getting stranger by the moment. She continued to explain things to me as we sat shoulder to shoulder.
"You obviously dont have a lot of experience with women. We know you've procrastinated with your time in Maryville. You have a wonderful opportunity there. We are here to help you."
I mentioned something about how did you know about that, in my own mind thinking aloud about my crush and their uncanny similarity in looks. "Never you mind how", she answered back. She then asked me if I ever had pleased a girl with my mouth. She put her hand on my shoulder and smiled at me.
"Well, your hesitation and silence answer that. You see Zack, we've studied you." It was getting stranger and a little more anxiety causing by the minute.
"First of all, lets look at you, handsome, tall, with two major caveats. Your eyes are way too innocent. They are shiny, dark green and black, very clear. People can see right through you. If you pursue a career, if you are going to teach, thats one thing. But if you go into the army you better develop a mean streak or at least fake it. You will get eaten alive. We don't want that. You are handsome. But your lips Zack, they are soooo thick and puffy. They belong more on a fashion model than they do on a man. We all agreed that they are tailor made for eating pussy." I was stunned by her brazen assumptions but said nothing.
"So, I want you to kneel down here, in front of me while i sit on the bed." She lifted her pleated khaki skirt. "I am wearing no panties. Just look for a couple of minutes." She was completely shaven, with two tender inviting lips, and smelled of vanilla. I completely swooned. She told me to scoot forward and let me guide you, to kiss around the outside. She encouraged to me to keep going. This went on for five minutes. She had me take my hands and open her up gently. She laughed and said something like not that gently.
"Now, use your tongue and explore everywhere, feel everywhere, learn good." I tongued her for about 20 minutes. She started humming and grasping my head gently. Then not so gently. I felt her heat rising. She grasped my head, and said, more pressure, more pressure NOW. RIGHT THERE DONT STOP. I didn't, as her essence cascaded like a hard rain over my face. Finally, it ended, and she fell back exhausted. After a few minutes, she reached down and uncuffed me.
"Get up on the bed." I did so, not knowing where to put my hands. We spooned, she reached over and slung my hands over her shoulders. All the while, in the background, the sound of the train, the lurches and rolls, was soothing and we both went to sleep.
I woke up the next morning as Isabella was gently shaking my shoulders. "Good morning Zack." She was already dressed in feminine khaki pants and blouse, her long brown hair matching her freckles nicely. She told me my next lesson won't be as enjoyable, although she said you will come to cherish it in time. She reminded me to provide pleasure, regardless.
"Now, dress and go get some breakfast lazy." She rubbed my head as i sat up, got up and left.
I wandered out to the breakfast car and ordered eggs and toast, with Columbian coffee. The import of what had just happened to me hadn't sunk in. Provide pleasure? I instead thought, how strange and how lucky I was! What a story. I couldn't wait to get to St. Louis, stretch my legs, and get some court time. Wrong deduction by me again.