Jessica

by Kimwell (Oct 99)

Earlier this year Tom moved to New York to take a job at a law firm.
We lived in a loft apartment in Manhattan.
He worked and seemed to be happy that I was home doing the wifey stuff.
I wasn't happy and we often argued. Don't get me wrong, I was still so in love with him, and when we made love I often thought, with deep pleasure, of conceiving his child.

I took long walks around town.
I liked to visit the art galleries the most, and then go to a cafŽ and drink lattes and stuff.
That's how I met Jessica. I was wandering around a small gallery and sat down to explore my purse, to see if I had enough money to eat that afternoon.
A girl, about 16 or 17, sat down beside me and said, 'that purse is so pretty, can I ask where you got it?'.

I named an expensive shop uptown and she gave me a rather curious look.
I wasn't really dressed for the art scene: white shorts and a pink blouse, tennis shoes and my totally out of place purse.
It was my slouching around town uniform.
She, on the other hand, was really dressed up: a long skirt, and a really cute jacket and blouse combo.
We smiled at each other, recognizing in each other the loneliness that would spark our friendship.

We started talking about where we lived.
She seemed to be in a really Cinderella situation: she lived with her mom, who was really mean to her. Dad had disappeared ages ago.
We continued our conversation at a cafe, I bought her an iced tea. Like a lot of girls her age she wore too much makeup.
I decided to wean her off that as soon as possible: she had an absolutely angelic face, even if she was waify.

Soon we started to hang out all the time, it was summer so she wasn't in school, and we visited more galleries and looked for clothes.
Spending all that time together we soon became close friends.
Often we would hold hands when we went walking together. We sat arm around arm in movie theaters, we hugged a lot and kissed when we met and parted.

She even went with me to the doctor's.
She would sit in the room while I lay on the table, my feet in stirrups while the doctor used a flashlight and a speculum to examine me.
She was really curious about that part of the exam and I could see her trying to peer past the doctor's shoulder into me.
At the time I thought she was just concerned for my safety, but that was not quite the case.

A few days after my check-up, we went shopping for clothes.
I was trying to build an all-black ensemble so I went into the dressing room with Jessica. I was wearing a black blouse and stockings and was going to try on a short black skirt when I noticed Jessica looking at the bush of pussy hair dimly visible through the stockings.

'Jessica,' I said, 'what are you doing?'
'Nothing. Just looking' She was embarrassed.



'How come I'm the only one who gets undressed when we're together?' I asked.
'Uh' She said.
'Here you try this skirt on'
I grabbed her skirt by her hips, and while she was protesting I pulled it down to the ground.
I was sitting on the floor when I noticed something wrong.
Her vulva seemed all fucked up and distorted.
Then I looked closer: it was a little dick taped back between two balls.
I looked up at 'Jessica' - tears were streaming down her cheeks.
I got up and pulled up her t-shirt, without resistance and saw that 'her' bra was stuffed with cotton balls.
'Jessica' was bawling.
I'm so sorry, he said, I was going to tell you.'
Why did you do this? I asked.
I just want to be a girl. When I get older and get some money I want to have an operation. Being a girl is what makes me happy, being with you was - well the first time I was accepted as female. My mother just thinks I'm a fag, but really I'm a girl in a boy's body!

I comforted him, I felt so bad, I started to cry too.
We hugged for a long time.
Finally, I said, ok, you want to be a girl?
He nodded yes.
'Well, first, you have to know what it is to be a boy.'

With that I slumped down on the floor, untaped his little weenie and put it in my mouth.
It was so small but soon grew enough that as I sucked on it I had to move my mouth around to get it all inside, but he was still a lot smaller than Tom's sausage.
I looked up at him, the tears were drying up and he was looking down at me with the utmost love in his face.
I love giving pleasure, it feels me with such joy.
I started to finger myself with one hand and used to the other to grip the base of his cock while I sucked my merry mind away.

He started to buck his hips and I saw his eyes roll back in his head.
He groaned and I did too, well the best I could with his cock in my mouth.
He started to spray thick gobs of his salty-sweet spray into my mouth.
I blushed deep red as his spurts turned into a dribble and I sipped him and finally licked him dry.
He helped me up and kissed me on the lips.
I helped him become a girl again.
I went to go buy the skirt. There were people waiting for the dressing room and they stared at us leaving, hand in hand.

At the cafŽ, Jesse, his real name, told me he wanted me to accept him as a young woman.
He wanted nothing more than me to help him learn about being a woman.
I was flattered, but also curious too.
'Didn't you enjoy what I did in the dressing room,' I asked him.

'Oh yeah, that was beautiful.' He seemed so struck by me.
'Maybe you can teach me how to do it one day.'
'okay, but you have some other things to learn about too.'
He was so cute, he had long hair, that reached to his earlobes, like mine.
He touched my stockings.
I shifted the chair so he could move his hands up my stockings, and under my skirt.
'Let's go to my place' I suggested.

Trembling he sat next to me on the bed I share with Tom. 'I've never did it with a girl before.'
'Good' I said, 'then you'll learn about being a girl from making love to one.'

He undressed completely.
He had a hard-on but a questioning look on his face.
'You have to take the initiative' I said.

He nodded and again ran his hand up my stockings and under my skirt.
He gently touched my labia, tracing them with a finger, I was so damp there that when his finger pushed into me through the stocking it made a squishing sound.
'It's so soft' he said.

I held his little cock in my hand, coaxing as best as I could his hard-on.
You're so hard, so manly' I said. He blushed.
It was the wrong thing for me to say, to remind him of what he was not.
But he recovered and lay me on my back.
He pulled the stockings down.
My blouse was open, I undid my bra for him and he fumbled around with my breasts.
He cupped them in his hands, feeling them. 'It's like both solid and watery,' he said gently shaking them. My rosy nipples became erect and he got on top of me to suck them.
'Oh, maybe I should put something on'
I didn't have condoms, but I was on the pill so I said just do it.
Trembling he first put his dick head on my anus. I shook my head no, 'wrong hole'.

He then moved it up a little bit. I couldn't see over my furry little mound, but the blossoming sensation around my inner labia told me he had found his mark.
He plunged into me, and began to kiss me all over.
His little cock was greased with my cum as he started to pump away.
He played with my breasts and suckled over and over again, stirring in me feelings both maternal and slutty at the same time.
Suddenly he started to rattle and came inside me.
He jacknifed onto the side of the bed and clamped his mouth on a nipple.
I put my hand between my legs and felt his come, warm and sticky slowly oozing out of my blasted open pussy.
I went to the bathroom to let his sperm drain out of me.
He came in to watch.
I showed him how to douche and we got into the shower. It was 430 and Tom would be home soon.


We were planning a big surprise for him.

To be continued