A first sexual experience

My sister’s best firend, Flora, was 19 when I was 18. It seems that
she had heard some horror story about how a girl’s first experience
with intercourse was always painful. Flora and my sister, Helen,
discussed this for a long time. Flora was planning to have her first
experiece with her boy friend and she wanted it to be perfect. So
Helen and her hatched a plot. It seems that Helen had volinteered my
services to be the first to enter Flora so as to make her first “real”
(as Flora put it) intercourse a more romantic happening. Since I
liked Flora and though she was about the prettiest girl I had ever
seen, I was more than happy to oblidge and followed their directions
as best I could.

Flora pulled her pants and panties off and set on the edge of the bed,
Helen sat next to her. I saw the triangel of pubic hair where
Flora’s legs met. “Well come on dummy, you got to get undressed too”
Helen taunted me.

When finally I was standing there in the room in my birthday suit,
they looked at each other and giggeled. Flora goes “I dont know about
this, he’s so small”. I wasn’t sure what she was refering to. After
all I was taller than most of my friends and was just slightly shorter
than Flora even though she was 2 years my senior. “Come over here
Kevin” Flora said. I walked over and stood in front of her. She
reach out and pulled me closer so I was standing between her legs.
Then she surprised me by reaching for my pecker. She streatched it
out as far as it would go. “I dont know he’s really small” she said
again. Helen said, “Well just try and see if it works”.

Flora started squeezin me more and wiggeling me with he hand. With
her giving me that kind of attention, I blushed all over, and started
to get an erection. “He’s cute” said Flora. Soon I was stickin
straight up to my tummy. She pushed the skin on my penis down as hard
as she could and the head popped out. Now I should tell you something
about my sexual anatomy. I didn’t know it at the time, but I am
considerably under average in size, even as an adult. I must not have
been more than 3 inches long fully erect. “I don’t know about this”
Flora said again.

Flora scooted back from the edge. She put her feet up on the bed and
gaped them apart in front of me. She laid back and spread opened her
sex with her fingers. I saw inside. It was all wet and pink. She
said to Helen, “Help him get it in right”. Now Helen stood beside me.
She took my little erection in her hand and directed it to the
opening in Flora’s sex. “Push it in there”, she said to me. I pushed
forward into Flora’s sex. The feel of her wetness tingeled on my
sensitive penis skin. I can still remember that feeling today. “Push
it inside” said Flora. I pushed in. “I dont think its in” I said.
“No,” said Flora, “Push harder”. Helen put her hand behind my butt
and tried to help me push. “He’s not going in” Flora said. Then
finally it did slip in .. all the way inside her … my penis was
stickin fully in her. “OUCH” screamed Flora pushing me away, “Not
there, your on top of it!”

I stood there with my penis twitching and tingeling while they
examined Flora’s sex. “He’s so small he just slipps up around it, and
when he’s pushing on it, he doesn’t push far enough”, was Flora’s
analysis of the situation. “Try again” said Helen. Flora took my
penis in here hand, she held it to her sex but she directed it down
further than it had been. “Push in hard right there” she said, “And
keep it down”. She kept her finger on me for a moment to keep it
pointing right. I pushed as hard as I could into her. But her sex
seemed to stretch in as I pushed and I couldnt get myself in her that
way. Finally Flora said “Oh stop it, your not doing anything, your
too short!” She seemed disgusted and mad at me. “Oh ok, he cant do
it”, Helen said. Then to me “You should go wash yourself off.” With
that, I was dismissed from their prescence. They closed the door on
me. I never did find out how Flora worked out her problem.

That experience has dominated my relationships with the opposite sex.
It is difficult for me to go beyond an intense feeling of inadequacy.
I still have a firm belief that I will never be able to properly
consumate a sexual relationship. Consequently, to this day, I am
reluctant to become intamate with women.