Our First Penetration

With my sister and I being as competitive as
we were, romance and seduction was not usually the way
one got the other interested in sex. We usually played
a “role game”, or made a wager with sex as the payment.
I would usually suggest that if she lost a bet she had
to show me her pussy, or I would get to touch it, or
she would have to play with my penis. If trying to be
more subtle, the wager involved a backrub with roaming
hands. One such incident resulted in our first attempt
at intercourse.

I was about 21 years old and Trish was 19, and we were
having a contest of who could make the most free throws
at the basketball court in the park. I suggested a
wager where the loser would give the winner a massage.
This was a win/win wager for myself. If I won, I would
receive the massage, and if I lost, I had the pleasure
of rubbing my hands all over my sister’s body, often
resulting in my being able to cop a feel.

I remember walking home from the park and being excited
at losing this particular wager. Trish and I arrived
to an empty house and proceeded to her bedroom. She
laid an her stomach and awaited her victory massage as
I sat next to her on the bed. I pulled the shirt up on
her back and began tickling her exposed skin.

It was a warm and humid day, and with the activity on
the court we were both hot and sweaty, so she didn’t
argue when I pulled the shirt completely over her head.
I tickled her back, then lifted her damp bra strap and
scratched the lines on her skin created by the bra’s
tightness. I soon undid the clasp of her bra, and
tickled her with long strokes reaching from her neck to
her hips.

The elastic on her shorts did the same to her waist as
the bra on her back, so I scratched that area, too, and
pulled her shorts down a few inches. I returned to
tickling and massaging and scratching her back. Though
her shirt was over her head and the bra unclasped, they
were still bound-up around her shoulders, and I took a
quick break to remove them completely, then briefly
tickled her hands and arms.

Noticing she was still wearing her sneakers and socks,
I removed them, and began tickling and massaging her
from the heels to the bottom of her shorts, and from
her head to the top of her shorts.

The long, gentle strokes to her backside were obviously
interrupted by those damn shorts. I don’t know why she
let me, maybe she was enjoying her massage, but when I
started to pull her shorts down a little farther, she
surprised me by raising her hips.

In retrospect, I’m sure she knew of my intentions and
was probably horny herself, but at the time I didn’t
have that insight. I did not pass on this opportunity
though, and lowered the remaining garments to the level
of her knees. I then caressed her smooth, round buns
with a light, circular motion, and soon watched her
breakout with goose bumps.

I finally removed the rest of her clothes and massaged
her naked body with strokes that traversed from head
to foot, with my fingers lightly traveling up and down
the crack of her butt.

I gently spread her legs and gazed at the pubes within
the shadows of her crotch. The trips over her butt
crack went progressively farther and farther between
her legs until I was lightly stroking her pubic hair.
She made no attempt to block my hand’s paths by closing
her legs, so I continued to caress her there.

At this point, I asked Trish to turn over so I could
“massage” the front of her body. Typically, if she
didn’t want any sexual contact, she would refuse this
request. Otherwise, she would turn over, but coyly
cover her breasts and/or her thinly covered bush with
her hands.

That was the case today. She placed one hand over her
mound and her forearm covered breasts. I did not
attempt to move her hand or arm, but instead lightly
massaged her neck and shoulders, and ran my fingers up
and down the length of her arms. When I lightly
caressed her stomach, she brought her arms in to stop
the tickling sensation, and I was able to catch brief
glimpses of her womanly parts.

This cat-and-mouse game continued for a short while,
until I began kneading her thighs. Having waited what
I thought to be a sufficient length of time, I gently
lifted her arms and placed them to the sides of her
body. Typically, if she was “playing shy”, she
resisted my attempts to expose her, but if sufficiently
aroused, she would leave her arms to her side and allow
me to view her full frontal nudeness.

On this occasion, she obviously wanted my attention,
and kept her arms to her sides, giving me a beautiful
view of those areas about which I often fantasized. I
ran my fingers over her upper body and slowly made my
way towards her small, firm tits. My fingers traveled
in large circles around her breasts, with those circles
getting smaller and smaller until finally they reached
her nipples. The light contact made them stand to

Gradually, I began massaging her breasts with both
hands, then ever so lowly my mouth was drawn down,
and my lips hovered over an erect nipple.

Her breathing came faster, and it was soon time to work
my way south. I let my fingers do the walking, and
strolled down the future “trail to happiness”. They
wandered into her growing forest and made contact with
her fleshy bud.

My light touch turned into gentle masturbation, and at
this point I brought my mouth off her nipples, spread
her legs and knelt between them. My fingers dabbled in
the folds of her beautiful genitalia. I lowered my
face toward her lap and let her feel my breath. With
this, I noticed her squirm as she spread her legs a
little wider for me. I pushed in with my tongue, and
tasted her. My tongue’s actions were light and slow,
but the pressure and speed increased with our mutual

In need of some attention myself, managed to remove my
shorts as I simultaneously practiced cunnilingus. My
erection was rock-hard and needed to feel the inside of
a woman.

My tongue slowly made its way out of the folds of my
sister’s pussy and led my face up her torso. My mouth
again met her breasts.

We were naked, her legs were spread, and I was on top
of her. I wanted to fuck her so bad. I wanted to fuck
her like I’ve never wanted anything else in my life. I
was also shaking, and a little scared. I asked her if
I could put “it” inside of her.

She closed her eyes and nodded her head. Slowly, I
rubbed the head of my dick against her clitoris and
spread my pre-cum around. The contact was intense
and forced me to pull away, lest I orgasm then and

After a short period of recovery, my dick returned to
his mission of penetration. Starting at her clit, I
placed the head into her labia and made the voyage
down toward her vagina. When my one-eyed monster was
directly over her sex hole, she whispered to me to put
it in, but warned me not to cum in her.

God she was tight — I quickly met a resistance, which
seemed to cause her some pain. Once again I was forced
to retreat, and to focus my attention on anything other
than her body and the incredible pleasure it was giving

I waited a bit, then attempted re-entry, but again
caused her pain. At this point she changed her mind,
and refused me any further exploration. A ruptured
hymen would be evidence of our incestual contact, and
we had no desire to incriminate ourselves, but I needed
to be inside of her.

I asked, or in retrospect, probably begged her to let
me fuck her ass hole. Obviously very horny and curious
about the act, she agreed. My mouth returned to her
folds. I fingered her cunt then spread our lubricant in
and around her sphincter. She moaned as I pushed my
finger into her very tight anus, but after repeated
penetrations, the circular muscle seemed to relax. I
gently pulled her to her hands and knees.

I was intoxicated with lust and possessed by carnal
desires. I wanted to fuck a hole, and she was going to
provide it for me. I spread her legs and positioned
myself between them, then pulled her ass toward me.

She lowered her elbows onto the bed and braced herself
with her forearms. I spread her cheeks and forced my
beast into her back door. She flexed her muscles and
denied my entrance. A bottle of tanning oil was on a
desk near-by, and a few drops were dribbled on her
sphincter. Again the monster demanded entry, and this
time she opened a bit.

Not sure of what I’d find, I slowly entered her. It
was warm, and dark, and very tight. My sister moaned,
though was it a moan of pain, or pleasure…or both?
My hips pressed against her ass, forcing my member
deeper into her.

She placed her weight on her shoulders and reached
backed with both hands. Her right hand finger-fucking
her cunt hole while the other rubbed her clit. The
thrusts were repeated and the monster grew larger,
until it could grow no more, then it spewed its con-
tents, forcing its way into the depths of my sister’s
bowels. She began to spasm, and the respective orgasms
tamed the savage beast.

We regained our composure and realized what had just
happened. The power of lust was frightening to us
both. At this point, our emotional immaturity was
evident, for we felt dirty, and a little embarrassed
by our sexual act. We caught our breath, I felt the
real need of a shower. Not knowing when our parents
would be home, we showered by ourselves. It seemed a
lonely shower to me after what we’d just done together.

After this experience my sister would never let me
touch her again like that. She would always refuse to
bet for sexual things in the future, but I’ll never
forget what we did, and how it felt…