The Woman I almost became
I thinking of something to write, I had so many ideas to put on this...but i will try to do one to start with.
This is what could have happened earlier in my life to change what and who i am now.
Thinking back to my teens...I was skinny, tall, and undesirable to the girls i was around. yes skinny and tall, 5' 11" and 140 pounds at 17. This is an honest retrospective on possibilities in my life.(this is 100% true for the first part of the story signified by the *)
Scenario #1
I was very venerable in high school, just a few geeky friends. I was allowed into the smoking area and could hang with them(yes we could smoke in high school back then).
let me back up a little. My family was a good Christian family. BUT my father was a hard worker and my mother was a housewife. My brothers were older and in college. My mother had leukemia and was in and out to doctors offices and the hospital for a month at a time...
I would spend a lot of time with her and watch her Soaps with her. She and I were pals. Well needless to say she succumbed to her illness and I was left with a hole in my life. My father was supportive and a good man but just wasn't my mom.
After her death...I had time alone at home with my father working and my brothers in Northeast Louisiana University and also working.
I found myself digging through her dresser a lot(father hadn't thrown anything away since he was still in morning and couldn't bring himself to toss her belongings.
I would strip off and put on her panties and bras...(her panties just hung on me cause mom wasnt small but i was so skinny also). i would walk around for a few hours every other day it seemed looking at myself, and masturbating. I liked how it felt. Soon i began finding some of her clothes she wore when she was younger and had kept.(did i feel funny wearing my dead mothers clothes? yes...but it was all i had).
I was 17 and had a virtually hairless body accept for pubic and under arms. So i was slightly feminine already.
I had gone as far as i could with what i had at home....until.*
Jeanne was a girl down the road i had known since she moved into the neighborhood four years before. She had just turned 17 and was gorgeous. Jeanne was part time lifeguard at a local pool so she was in shape. I drooled over her..and she knew it. We would hang out sometimes after school since she lived 4 houses down, and shoot baskets or watch baseball. Well, one day it was raining and she wanted me to teach her poker.(all guys where i am from know poker) so i showed her the basics and different combinations of cards. Jeanne was smart and so picked up on the game quickly so we played poker for an hour. We started betting little things like nickles and dimes. About a week later she and I started out playing friendly poker but she is very competitive...and decided to step up the stakes. Before we ever knew what truth or dare was we kinda had our own version. We each won hands and laughed at each others chatter. She won the last hand and asked me if i had secrets that would shock the family. I was so comfy and enamored by her i just blurted out that i wore womens clothes sometimes...(shock was on both our faces) but she smiled and said let me see...I explained that i didnt have and that fit because of moms butt was bigger than mine...
She disappeared and came back with a grocery sack full of clothes...Hers and her moms that they were going to thrown in the Salvation Army box. "lets find you something to wear more your size". Well the cat was out of the bag and she had one of those personalities that just made you feel relaxed...
so we put our heads together and found a skirt and blouse(you dont give away used undies) so she found one of hers and her moms older bras...and she went to work dressing me...
She wanted to watch me pull off my clothes but i was shy as can be. BUT i had never put on pantyhose and needed help so she poped into the room and assisted...She did notice my slender cock was hard in her panties. "you have a wet spot" and i turned red...she never flinched and helped me with the pantyhose. she hooked the bra and helped with the skirt...
This was the late 70s and guys had semi long hair...she sat me down at her dresser and began to primp my hair...I was enjoying it and started relaxing with her and enjoying being a girl.
I took it all off after a little while and she gave me a peck on the cheek and sent me home with a small bag of frillies to try on and wear.
Jeanne was friendlier than ever now and brought new things to try on. Then the makeup came, which i wasnt receptive too but soon over the course of the next month began to love. I would give her money to go get me some girly things.
She would do so gladly in her little Vega that her dad had gotten her.
Soon she had my hair feathered and it was a little longer(my hair grows fast).
One day she stepped back and was like wow T, your so hot!
She had been conditioning me over these last few months.
*Chatting about the Soaps, which i still watched and still do.
*Talking about relationships.
*She she would slip in talk about the boys she liked asking my thoughts.
All this led up to me going to a small out of the way mall in a close by town. I swear that girl could convince me to do almost anything...and she did...
Before i knew it, she had me dressed up in a shorts and polo(one of hers) and off we went to cruise one Saturday.(I have no idea where my family was when all this went on)
I didn't mind going out dressed up with her, as long as we didn't stop or talk to anyone... She was so into the whole having a new girlfriend to hang with. Of course i was silly and she knew I had to start acting more feminine(which she started when this all began and snuck her fem training in on me without my knowing a damn thing, being a dumb male). I was already slightly prissy and with her help I could wiggle my hips with the best of them.
One day her Vega went dead and couldnt get it started...of course we were miles from home and me in a knee length skirt! So I had no choice but to play a girl and try to be inconspicuous as i could. but long legs and short skirt were not inconspicuous. Cell phones were not around so we had to either call one of our fathers or wait for a jump start from a stranger. Well, low and behold a couple high schoolers from Calhoun stopped by...I could tell thier hormones were in full swing. both looked nice and nice smiles(OMG what was i thinking..) Jeanne put her hand on mine and walked me up to them and asked for help. They were glad to oblige. They had to remove the battery and drive off to get a new one...(I didn't have a wallet also no purse and Jeanne had only 15 dollars)...when they put the new battery in we let them know we only had 15 (batteries were only 25 then, but 10 bucks was 10 bucks). They were a bit peeved but Jeanne threw out we will go to the movie with them for the 10....
WHAT was she saying! no way in hell...
But there was that Jeanne factor, talking me into it. I agreed ONLY if i could wear pants. she agreed almost too fast.
So, That is where I met Jeremy. We went out with them 3 times...I was accepting being the new me. back then groping wasnt a first few date thing...that came later...I wouldnt let him touch me only kiss me which to Jeanne's delight was so hot. I gave my first blowjob after a month and he exploded in my mouth.(I had to get help from Jeanne on what a girl did) Well it was inevitable and i let him reach under my skirt....after i had blown his smooth cock off twice that evening...HE was OH SHIT A DICK!! but looking into his eyes and a slight tear in my eye, he kissed me warmly...my cock was hard as hell and so was his. he crawled between my legs after he had pulled my panties off. What do we do next he asked as he pulled his pants off. I just pulled him close to me on th tailgate of his truck and wrapped my legs around his warm skin. his cock rubbing my balls...
I pushed his cock with his precum on my asshole and told him it had to be wet wet...
I lend forward and spit on his shaft and rubbed it in and guided his cock to my ass and felt it press against my brown hole with a hardness that i had never felt.
Jeanne told me it would hurt as it had her pussy but I knew I had to do this.
IT was hell on my ass but also heavenly. We dated for a year. We still see each other and smile.
I am with his other friend I took from Jeanne and she is now a Psychiatrist specializing in such behaviors...
What do you think?
This is what could have happened earlier in my life to change what and who i am now.
Thinking back to my teens...I was skinny, tall, and undesirable to the girls i was around. yes skinny and tall, 5' 11" and 140 pounds at 17. This is an honest retrospective on possibilities in my life.(this is 100% true for the first part of the story signified by the *)
Scenario #1
I was very venerable in high school, just a few geeky friends. I was allowed into the smoking area and could hang with them(yes we could smoke in high school back then).
let me back up a little. My family was a good Christian family. BUT my father was a hard worker and my mother was a housewife. My brothers were older and in college. My mother had leukemia and was in and out to doctors offices and the hospital for a month at a time...
I would spend a lot of time with her and watch her Soaps with her. She and I were pals. Well needless to say she succumbed to her illness and I was left with a hole in my life. My father was supportive and a good man but just wasn't my mom.
After her death...I had time alone at home with my father working and my brothers in Northeast Louisiana University and also working.
I found myself digging through her dresser a lot(father hadn't thrown anything away since he was still in morning and couldn't bring himself to toss her belongings.
I would strip off and put on her panties and bras...(her panties just hung on me cause mom wasnt small but i was so skinny also). i would walk around for a few hours every other day it seemed looking at myself, and masturbating. I liked how it felt. Soon i began finding some of her clothes she wore when she was younger and had kept.(did i feel funny wearing my dead mothers clothes? yes...but it was all i had).
I was 17 and had a virtually hairless body accept for pubic and under arms. So i was slightly feminine already.
I had gone as far as i could with what i had at home....until.*
Jeanne was a girl down the road i had known since she moved into the neighborhood four years before. She had just turned 17 and was gorgeous. Jeanne was part time lifeguard at a local pool so she was in shape. I drooled over her..and she knew it. We would hang out sometimes after school since she lived 4 houses down, and shoot baskets or watch baseball. Well, one day it was raining and she wanted me to teach her poker.(all guys where i am from know poker) so i showed her the basics and different combinations of cards. Jeanne was smart and so picked up on the game quickly so we played poker for an hour. We started betting little things like nickles and dimes. About a week later she and I started out playing friendly poker but she is very competitive...and decided to step up the stakes. Before we ever knew what truth or dare was we kinda had our own version. We each won hands and laughed at each others chatter. She won the last hand and asked me if i had secrets that would shock the family. I was so comfy and enamored by her i just blurted out that i wore womens clothes sometimes...(shock was on both our faces) but she smiled and said let me see...I explained that i didnt have and that fit because of moms butt was bigger than mine...
She disappeared and came back with a grocery sack full of clothes...Hers and her moms that they were going to thrown in the Salvation Army box. "lets find you something to wear more your size". Well the cat was out of the bag and she had one of those personalities that just made you feel relaxed...
so we put our heads together and found a skirt and blouse(you dont give away used undies) so she found one of hers and her moms older bras...and she went to work dressing me...
She wanted to watch me pull off my clothes but i was shy as can be. BUT i had never put on pantyhose and needed help so she poped into the room and assisted...She did notice my slender cock was hard in her panties. "you have a wet spot" and i turned red...she never flinched and helped me with the pantyhose. she hooked the bra and helped with the skirt...
This was the late 70s and guys had semi long hair...she sat me down at her dresser and began to primp my hair...I was enjoying it and started relaxing with her and enjoying being a girl.
I took it all off after a little while and she gave me a peck on the cheek and sent me home with a small bag of frillies to try on and wear.
Jeanne was friendlier than ever now and brought new things to try on. Then the makeup came, which i wasnt receptive too but soon over the course of the next month began to love. I would give her money to go get me some girly things.
She would do so gladly in her little Vega that her dad had gotten her.
Soon she had my hair feathered and it was a little longer(my hair grows fast).
One day she stepped back and was like wow T, your so hot!
She had been conditioning me over these last few months.
*Chatting about the Soaps, which i still watched and still do.
*Talking about relationships.
*She she would slip in talk about the boys she liked asking my thoughts.
All this led up to me going to a small out of the way mall in a close by town. I swear that girl could convince me to do almost anything...and she did...
Before i knew it, she had me dressed up in a shorts and polo(one of hers) and off we went to cruise one Saturday.(I have no idea where my family was when all this went on)
I didn't mind going out dressed up with her, as long as we didn't stop or talk to anyone... She was so into the whole having a new girlfriend to hang with. Of course i was silly and she knew I had to start acting more feminine(which she started when this all began and snuck her fem training in on me without my knowing a damn thing, being a dumb male). I was already slightly prissy and with her help I could wiggle my hips with the best of them.
One day her Vega went dead and couldnt get it started...of course we were miles from home and me in a knee length skirt! So I had no choice but to play a girl and try to be inconspicuous as i could. but long legs and short skirt were not inconspicuous. Cell phones were not around so we had to either call one of our fathers or wait for a jump start from a stranger. Well, low and behold a couple high schoolers from Calhoun stopped by...I could tell thier hormones were in full swing. both looked nice and nice smiles(OMG what was i thinking..) Jeanne put her hand on mine and walked me up to them and asked for help. They were glad to oblige. They had to remove the battery and drive off to get a new one...(I didn't have a wallet also no purse and Jeanne had only 15 dollars)...when they put the new battery in we let them know we only had 15 (batteries were only 25 then, but 10 bucks was 10 bucks). They were a bit peeved but Jeanne threw out we will go to the movie with them for the 10....
WHAT was she saying! no way in hell...
But there was that Jeanne factor, talking me into it. I agreed ONLY if i could wear pants. she agreed almost too fast.
So, That is where I met Jeremy. We went out with them 3 times...I was accepting being the new me. back then groping wasnt a first few date thing...that came later...I wouldnt let him touch me only kiss me which to Jeanne's delight was so hot. I gave my first blowjob after a month and he exploded in my mouth.(I had to get help from Jeanne on what a girl did) Well it was inevitable and i let him reach under my skirt....after i had blown his smooth cock off twice that evening...HE was OH SHIT A DICK!! but looking into his eyes and a slight tear in my eye, he kissed me warmly...my cock was hard as hell and so was his. he crawled between my legs after he had pulled my panties off. What do we do next he asked as he pulled his pants off. I just pulled him close to me on th tailgate of his truck and wrapped my legs around his warm skin. his cock rubbing my balls...
I pushed his cock with his precum on my asshole and told him it had to be wet wet...
I lend forward and spit on his shaft and rubbed it in and guided his cock to my ass and felt it press against my brown hole with a hardness that i had never felt.
Jeanne told me it would hurt as it had her pussy but I knew I had to do this.
IT was hell on my ass but also heavenly. We dated for a year. We still see each other and smile.
I am with his other friend I took from Jeanne and she is now a Psychiatrist specializing in such behaviors...
What do you think?
11 years ago
