Jerry becomes Jill Pt. 01: The Beginning

Please bear with me as this story gets off to a slow start as I set the stage for what will happen later. Thanks for reading this and please leave comments.

My name is Jerry, or as I am better known now Jill and how this happened is the story I am going to relate here and in future sections of this tale. I was always a small boy for my age, reaching my adult height of about 5' 2" in the ninth grade. In addition to being relatively short I was small boned and not very muscular. I was not athletic but participated on the school debate team and chess team. I had a few dates during my freshman and sophomore years but nothing to write home about.

Things changed in my junior year when they announced that they were adding two male cheerleaders to the squad. One of my friends and I decided to try out for the two spots. My parents had paid for me to have dance lessons when I was younger and these paid off during the tryouts. My friend and I made the team and had a ball cheering at football and basketball games. Additionally we got to spend a lot of time with some of the prettiest girls in school. Unfortunately most of these girls were chasing the jocks, although I did score a few random dates with a cheerleader, there was nothing serious or long term.

The big benefit of being on the high school cheerleading team was the advantage it gave me when I got to college. I was invited to try out for the college cheerleading team and made the team as a reserve in my freshman year. One thing that was different at college was that all of the girls on the team were as tall or taller than me, which meant no dates with my fellow cheerleaders, at least not to start.

When I returned to college for my sophomore year I was promoted to the varsity cheerleading squad, which meant cheering at the games and traveling to away games, including some overnight trips. Shortly after the start of the semester, Rikki, the captain of the cheerleading squad met with me. We talked about the importance of classes and good grades, practices and other things. She also stressed that if I had any problems I should come to her for help. I thanked her and agreed that we would have lunch once a month to make sure no problems came up.

As for my personal life practice and studying took most of my time. I had a few dates mostly with girls from class in my major, finance. The lunches with Rikki helped keep me grounded and focused. But there were many nights where I had a date with my hand. Then the week end before Thanksgiving world came apart.

Shortly after midnight I was awoken with a knocking on my dorm door. When I opened the door a state trooper was there and after identifying himself he asked if he could come in and talk. We got back into the room, by this time my roommate was awake, as well. The officer then said, "There is no easy way to tell you this but your parents were killed in an automobile accident this evening. At present we are not sure what happened but it appears they were run off the road as they approached the bridge over the John's River and the car ended up in the river. I am so sorry. Is there anything I can do for you?"

I told the officer, "No, I need to tie up a few loose ends here and then I will head home tomorrow. Who will have the details when I get back t town?"

The office gave me his card and told me to call the number on it and his office would help.

I sat there in shock for some time, realizing I was alone in the world. I had no siblings, and both my parents were only children. I discussed what need to happen with my roommate and then started to pack my clothes and books so I could leave in the morning, before trying to catch a nap. Up and ready to go at 7:30 I called Rikki and told her what had happened. I then asked if I could meet and talk to her about what needed to happen and school. She said of course and gave me the address to her off campus apartment.

I loaded the car and drove over to Rikki's apartment and she had breakfast ready for both of us. After that I told her what I had planned and ask her if she had any ideas about school? She called the dean of students and explained my situation. After about a fifteen minute we had it worked out where I could to finish my class work for the semester and be back in class at the start of the next semester. I told Rikki I would keep her posted on my plans and left for the hour drive home.

Our neighbors as I grew up were the Browns. He was an attorney and I am not sure what she did. When I got home I talked with Mr. Brown and he helped me get things going. We got the insurance claims filed, the funerals set-up for the Saturday after Thanksgiving. The day of the funerals arrived and several of the cheerleaders and friends from college drove down to give me support. Rikki hung around after the funerals and went to a reception put on by the Brown's and my dad's former employer.

After that I convinced her to spend the night in the guest bedroom at the house and drive back in the morning. She agreed and we sat around and talked until the early hours of the morning. As we headed to bed Rikki gave me a light kiss on the check and said, "You are handling this well. Let me know if I can help in any way."

In the morning we had a late breakfast and talked of my plans. I told her I was interviewing real estate agents and would be putting the house up for sale. Rikki said that she would plan her Christmas break schedule and spend a couple of days helping between Christmas and New Year's if I could use the help. I said that would be great as she gave me a light kiss on the check and left to get back to school.

Time flew by as I meet with real estate agents, lawyers, financial planners, estate sale persons and I don't remember who else. Soon it was the twenty-eighth of December and Rikki was due in later that day. I spent the morning cleaning-up and getting the guest room ready for her.

Rikki got in about 4:00 in the afternoon and after a warm hug we got her settled in the guest room. We then settled in the den and got caught up on what had been going on. I told her I was selling the house and one of the remaining cars keeping dad's sports car for me. There was an estate sale set for after the first of the year and that I would be financially set for life if I was careful. We then went out and got some dinner before coming back to the house to talk before going to bed.

The next few days went by quickly as we packed things I was going to keep and put them in a storage unit that I had rented. Before we knew it, New Year's Eve was here and even though Rikki had planned to go back to school to celebrate, she decided to stay with me. I was able to get us dinner reservations which included a New Year's party. Since we would be drinking we took a cab to dinner and the party where we had good time. The cab picked us up a 12:30 and we got in the back for the 20 in ride back to the house. Although we had been drinking we were not drunk but feeling good.

As the car pulled away from the restaurant Rikki slide over next to me and put her hand on my thigh. Sliding my arm over her shoulder I pulled her close and she put her head on my shoulder and whispered, "Thank you, I had a great time."

I looked her in the eyes and replied, "Your welcome, I had a great time as well."

Rikki turned a little looking into my eyes and kissed me full on the lips.

The kiss lasted for a little while before she broke it off and we looked at each other. I bent forward and kissed her hard again. This time her tongue probed into my mouth and mine into hers. Breaking off the kiss we sat in silence the rest of the way back to the house, my arm around her shoulder and her hand lightly stroking my thigh.

We arrived at the house, got out of the car and walked into the house hand in hand. After I closed and locked the door, Rikki took me in her arms and kissed me passionately. After the kiss she whispered in my ear, "Come to bed with me." I nod and Rikki took my hand and led me to the guest room.

As we enter the room Rikki turns, grabs me and kisses me forcing her tongue into my mouth. Without breaking off the kiss she starts to undress me. Interpreting this as a green light I start to undress Rikki but she stops me and says, "Let me do you," and continues to undress me. When I am naked she kisses me again, while gently stroking my cock.

After continuing this for a few minutes she says, "Lie on your back on the bed and don't touch your cock." As I lay there Rikki slowly and seductively removes her blouse and skirt, leaving her in her panties, bra, garter belt, stocking and heels. What a beautiful sight of this tall strong woman!

Rikki turns and walks into the adjoining bathroom, from which she shortly emerges with a bottle of lotion. She slowly walks to the bed and sits on the edge. Pouring some of the lotion on her hands she reaches over and starts stroking my cock. As she is slowly teasing and stroking my cock Rikki says, "Relax and enjoy, this is all you will get tonight." I am enjoying her gentle touch too much to question the last part of the statement.

Rikki continues slowly sliding her hands up and down my hard cock and teasing my balls with her beautiful finger nails. Each time I would get close she would stop long enough for me to come back from the edge, before starting over.

After about forty minutes and coming close a number of time Rikki finally took me over the edge allowing me to shot my cum all over my chest and face. With the head of my cock super sensitive, while gripping my cock in one hand, Rikki continues to tease the head with her nails and rub it with the palm of her other hand. The sensation drives me crazy!

Rikki stops and scoops up my cum in her hand and brings it to my mouth saying, "Open wide." Still being in that warm post orgasm place, without thinking I open my mouth and as I do, Rikki scrapes my cum from her hand into my mouth. Realizing what had just happened I start to sit up to spit the cum out of my mouth, but as I do Rikki bends forward and start to kiss me again, saying, "Swallow." With her lips pressed against mine I have little choice but to swallow the cum. As I do Rikki pokes her tongue into my mouth and kisses me erotically.

As she breaks the kiss Rikki says, "Go into the bathroom and clean-up and then come back to bed." I get up and go into the bathroom and wash up the mess off my chest and take a piss. When I return to the bedroom I find Rikki in bed and covered up. I pull back the covers to get into bed and discover Rikki has on a pair of flannel onesie pajamas. To say I was disappointed would be an understatement.

I slide into bed and Rikki cuddles up next to me and gives me a kiss saying, "Happy New Year and thank you."

I give her a kiss and say, "Your welcome, but what about you?"

Rikki says, "I'm fine we can talk more in the morning. Let's get some sleep," and cuddles close to me as we fall asleep.

When I wake up in the morning Rikki is already up and in the bathroom. I go in and take my morning piss and Rikki says, "Good morning sleepy head. How about going and making us some breakfast while I get a shower?"

"OK, but I need to get some clothes on first, "I reply.

"Not to worry," replies Rikki as she hands me a pair of her light blue boy-cut panties.

"I can't wear these," I respond.

"Sure you can. I think you will look cute in them," replies Rikki with a smile and then she adds, "Do it for me. It will be our little secret."

I take the panties from her and slide them on. I like the way they feel and my dick is starting to get hard. I head to the kitchen to prepare breakfast as Rikki starts to disrobe and get in the shower.

Twenty minutes later as I am putting the last of breakfast on the table Rikki walks in wearing nothing but a sexy sheer black lace teddy and high-heeled pumps. We sit down and start eating breakfast, when Rikki says, "Thank you for wearing the panties, you really look good in them. After we finish breakfast I will need to get packed and head back to school, classes start in four days."

"I understand," I reply and then add, "I will be heading back in a day or two as soon as I finish up some loose ends here."

"Where are you going to live this semester and what about the summer?" asks Rikki.

"I was planning on living in the dorm this semester and not sure what I will do during the summer," I replied.

Rikki responds, "I have three bedrooms in my apartment, you could have one of them and go to school during the summer. I am going to go to graduate school next year so we would have over a year to plan on what to do next. I could charge rent at much less than your dorm fees and we could share the food costs. What do you think?"

"I like that idea, but what about my commitment to the dorm?" I answer.

"I will see if I can get you out of your commitment with the dean when I get back to school and call you," replied Rikki adding, "No commitment on either of our parts concerning last night."

To which I replied, "Understood."

With that taken care we finished breakfast, got dressed and got Rikki on her way back to school. As we were saying good bye, Rikki reached in and gave me a kiss and pushed something in my back jeans pocket. After she left I reached into my pocket and pulled out the blue panties from this morning.

I got busy getting ready for the estate sale, the sale of the house and ready to go back to school. That night I slept in the panties, thinking about the previous night and Rikki resulted in a long masturbation session before I fell asleep.

The next day it was back to getting things wrapped up when Rikki called just before noon. We talked for about twenty minutes during which time she told me that she had the dorm room issue resolved. That when I got back to school I should move in with her and that we would need clean out my dorm room by Tuesday. Before hanging up I told I would be back Sunday night and we could handle the dorm room on Monday.

After hanging up I told her that I would see her soon and got back to getting ready to return to school in a few days.

To be continued.......