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Tomboy named Sue

Categories Fiction, First Time, Virginity

Authror: oldnerd

Published: 06 June 2017

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This is a re-write of a story I did a few years ago. Hope you all like it.

The story is largely fiction, however, it is based on some of my early life’s happenings, and Sue was real (but not her real name).

Our parents owned houses next door to each other. The neighborhood was lower middle class, so almost all families were living hand to mouth. Her Dad was a union machinist and did well enough so her mom did not have to work. My Dad’s goal in life was to own a home, something his parents couldn’t do. My mother worked as a book keeper for a woman’s clothing shop, and dad delivered heating oil and gasoline. Being young in the great depression, dad quit school when he was 14 to help support his family, and was not well educated, hence the lower pay. However, we had a home, food on the table and a car that ran. Not a new one, but it got us where we wanted to go. But we had very little else.

Sue and I met when we moved in, about in the 6 th grade. Being only children, we treated each other like brother and sister (in a non-sexual way) until later. Read on…..


I was very skinny and only 5.7, 117# at graduation from H S. I wore very thick glasses, and was very smart; I was viewed as a nerd. The only athletics I ever did was cross country runner in my senior year. I was not that good, but the Phys Ed teacher promised me an “A” if I did this. My GPA was very important to me. Being that we were poor, I kept my studies up to make a scholarship possible, as that was the ONLY way I was going to college. And college was my ticket out of being poor.

Sue. She was about 5-5, 120#, small chest, collar length black hair with a cute face. Was not ugly or “hot” and would not stand out in a crowd. She was definitely a tomboy. She also dressed like one of the boys: loose fitting jeans or warm up pants, and a baggy sweatshirt. Moreover, the neighborhood guys treated her like “one of the guys” She was a gifted athlete, particularly in fast pitch softball. Her school team took the state championship, and this got her a scholarship to a state college in a town about 100 miles away.

She had problems with math and science. That’s where I came in, helping her study that 2 subjects. She was good in English and social studies, though, and helped me thru them in H S.

When we were seniors, one day she came over crying. She was harassed by one of the popular guys because of her athletic accomplishments. Those guys migrated to the cheerleader type of girl. You know, blonde, small and bimbos

He called her a lesbian, in front of a lot of other guys. She did not date, as she just did not find most guys to be “suitable”. She was not a lesbian or Bi. As said, just did not find the right guy. I suspect she wanted a male counterpart of her, like someone who was athletic and understands competition.

So I comforted her and told her they were wrong. And I would be very happy to take her out on a date, if she would have me. So, we made a date for dinner and the movies that Saturday. I worked part time in food service at the sports stadium so I had some spending money.

Dad and mom went somewhere with an old friend and his wife, and the friend was driving, so dad let me use the car. I picked her up at her house front door. She had on a nice dress, heels, did her hair and looked very cute and feminine. I had on a suit and tie. We looked damn good.

The dinner was good and we talked about things not related to school. Then in the movie theater, she puts her head on my shoulder. I put my arm around her. She puts her hand on my leg and rubs it, but not near my Johnson. So I do the same to her and she smiles. We snuck some kisses, but nothing serious. Like brother and sister. On the way home, I mentioned that my parents were not expected back until late, so she said “let’s go in and talk some more. My dad won’t mind, he trusts you”

She mentioned that she was still a bit taken back about that dude’s lesbian remark. I said I will mention to some guys that I went on a date with you and you are not a lesbian, and a very nice girl. She jumped into my lap and started kissing me on my lips. This was definitely NOT a brother/sister kiss. Yeah, boy I was enjoying it, and my Johnson came to attention. She felt that happen and said “Did I do that?"

I said “yes, I really meant it when I said you look really good tonight. You should wear dresses more often. Matter of fact, maybe if you wear more feminine clothes, like dresses and skirts, it may help erase the bad mouth that guy did on you”

Then she asked: “Have you had sex with a girl, yet? “(I did not date much either, because being a nerd; the "cool" girls were interested in the jocks or otherwise “cool” guys) I said “No”

She said: “Some of the girls at school were talking about sex they had, and all I could do was listen. So, I would like you to be my first and break my cherry, but, not tonight. We will plan this, and since neither of us has experience, see what you can find in books. You are better at research than me” (this was way before internet).

I said “I will do so, and get some protection”

In that state you had to be 18 to go into an adult bookstore or to buy condoms. This was an old town and mostly very religious people. Talking about sex is taboo, and it was not covered in hygiene classes in H S. A fellow nerd, who was older, found an illustrated book of “Pleasing the woman in your life” somewhere, which discussed foreplay, positions, and afterwards. (He must have went to another town) Today just ask the internet and you shall receive.

I got rock hard just reading the book. Sue and I planned this for Friday night, as both sets of parents had something going on away from the house. I went over there. Her bed was bigger. She was wearing the same dress as on our “date” night. Hair done, looked as good as ever. I showed her the book. We started with the foreplay part: kissing, foundling and playing each other, and playing with each others equipment. I found the clit and rubbed it, while she stroked my dick. She got very wet very quick. I thought I was going to cum way before I was supposed to, so I slowed down.

She put extra bedding down as we did not want to get blood and/or cum on her bed for her mother to find later. Then I put on a condom, and mounted her in the missionary position, as this was the first one in the illustrations. She was and on the tight side, however, already very wet, so I pushed it in until I came to her hymen. She said “Go for it. Fast and finish” and this is what I did. She let out a shriek when it broke, and I stopped. She said: "Stay like this for a moment and let me get used to it.”

After a while: “Keep going now” I got it all the way in and by that time she was moaning and dripping wet. Both of us were really enjoying this, I’ll tell you. She stiffened up, pushed against me with more force, and squeezed my dick with her pussy muscles, and had her first orgasm. We just laid there for a few minutes.

After a while, she said, “Get off me. I want to look up a position where I am on top”

I said: “I’m game to learn more”

She found “cowgirl” in the book. She straddled me, grabbed my cock, positioned herself on it, and slid down on my very wet cock, balls deep. I think it went in further in this position, because I it felt bottomed out. Here’s where her athletic ability and leg muscles made for the best girl-on-top I ever had. Hey, all you have to do is lay there and stay hard. Then, she had another orgasm and I came. Being I was 17, I stayed hard, and after a rest, we went at it again. Both of us had another orgasm. We cleaned up and I went home, as the parents were due back soon.

The next day she came over and said her mother asked what we did last night. She told her we read a book and studied physical stuff. We both laughed…….After all she did not lie to her mother.

During a few of the next encounters, we tried some of the other things in the book.. We both had reservations on oral. It was not a popular as today, and the thought of putting your mouth on that area, was a bit repulsive. We decided one time to wash each other up in the shower and try it. We got used to it fast and liked it. However, we always washed before (and after) for all the oral encounters, as a force of habit. We did 69, and had sex outdoors a few times. However, we agreed on our favorite position being cowgirl. I thought she liked being in charge. Not that I am complaining...

Neither her, or my, parents even remotely suspected our activity. Around the house we acted like brother and sister, or best friends. A couple of times when we went out, her dad let us use his car when my family took ours somewhere. He once made a comment: " What the hell did you do to get her ino a dress?" However, our sexual encounters were carefully well kept secrets. I escorted her to the senior prom. She did get attention from our friends in the prom dress her mother sewed. She was more popular, especially with the boys, as she looked a lot more feminine. The girls were more receptive as "one of their own".

Then, summer came and went. She was going to college 100 miles away, to study English to teach, and a minor in teaching phys ed.

I was accepted in a local technical college with a scholarship, and studied electronics. Being we were not moneyed; I lived at home and took the bus. Sue and I corresponded with mail and sometimes a phone call. During the breaks, her father loaned me their car to bring her home, as he worked days and her mother did not drive. We did our thing when she was home. The next summer, she stayed at school. She found out that she could graduate earlier and maybe go for a masters degree with the money allocated. I worked that summer and saved up enough for a jalopy of a car. Looked like crap with rusted sides because of the winter road salt, but ran very well.

I made a few trips to visit her and we kept each other satisfied. I saw that she dressed in skirts and dresses. Let her hair grow a bit longer, like shoulder length. Looked like a normal college girl. She had lots of friends. And she looked a lot cuter.

During her 3 rd year she met a guy who was a pitcher (and captain) on the varsity baseball team. She was the captain of the softball team, which was in contention for the national title. She fell in love with him and our sex sessions came to a screetching halt. But we still corresponded and talked when she came home. Again like brother and sister.

After getting my degree, I went to work as an engineer, at a local company. I found a girl I liked and got married. We bought a house near where I worked. We did OK money wise. Wife was a homemaker, and did not need to work. We had a daughter. She married her high school sweetheart right after graduation, and they moved to another town about an hour dive away. We visited each other a lot.

Sue and her guy got married. However, he got injured and his baseball career was over. But he had a degree in Physical Education. They accepted teaching positions out of state, although his was at a different school in the same town. Their son became a computer wiz. We corresponded with Christmas cards, letters, etc. We never told our spouses or parents about the Sex Ed sessions.

Fast forward about 20 years. One day she called me and said her husband died in an auto accident. The other driver was drunk, and was driving a company car. The company did not want it publicized, so they settled out of court with a large amount the next day. I went to the funeral. She was very shook up, as they had a good thing going. I said if you need anything I can do, call me. We met a few times and talked about different things, but no sexual tones. I was married and happy, and she knew this and honored it.

2 years later, my wife had some blood vessel near the heart burst. She died before they got her to the hospital. Sue was at the funeral, and said to call her if I need anything, or someone to talk to. My company paid 100% for both our life insurance policies, in the amount of 2 years of MY salary, so I did not have any financial worries. After a while I tried some dates with other women, but there was never any music, if you know what I mean..

A few months later, Sue’s son got married. I was asked to be part of the head table, next to her. We got to talking afterward, and I said: “Now that your son is married, why don’t you come and stay with me for a while. If it works out, we can make it permanent” She said she will drive there tomorrow.

They next day, she arrived about noon. I made some lunch. After lunch we had a long talk. Then, she took my hand and lead me to the bedroom. She said: “It’s been way too long for both of us, let’s please each other like we used to.” She started taking off her clothes. Who am I to argue? I noticed her legs were still muscular, and she was in good shape, as also I was. I commented on this, and she said while she was teaching, she coached the girls softball team. Then, in a mischievous voice she said “cowgirl?” I said “ride em cowgirl”

We did that, and some other positions. We lay in bed and talked more. Her husband did not like cowgirl and any position where he wasn't the "team captain". She said although her husband had a somewhat bigger cock, (He was 6-4) sex was better with me. Being 5-7; I made up for it with technique. I said my wife was maybe twice a week for sex, but would not do oral, either receiving or giving. Her religious background was quite heavy. However, I learned to live with it being she was a great wife otherwise.

After 6 months, we got married. She gave her house to her son, and we made my house our home. I had a more modern home , in the suburbs, with a pool and an exercise room. With the combination of her settlement and my wife’s life insurance, we did not have to work. We were retired in our 50s. We both volunteered for the public school system to help problem children get thru school.

She had brought a lot of boxes which got placed into my storage area over the garage. I had stuff there which sat from the time I moved in. About a year later, we went thru them to discard unwanted and display some wanted mementos, and we found the well used, dog-eared sex book we used as teenagers. We laughed, cried and went to the bedroom.

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Tomboy named Sue

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Comments (4)
oldnerd02 June 2017 20:04
Crazy Col: you nailed it. Sorry about that.
Crazy Col — 01 June 2017 07:06
Too many grammatical errors made this story hard to read. Once you got to 3rd year of College you rushed the story.
mature gina — 01 June 2017 03:36
I certainly enjoyed it.
LeahR — 31 May 2017 12:56
A nice story.
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