Our First Penetration

With my younger sister and I being as competetive as we were, romance and
seduction were 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 15 years old and Trish was 14, 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 did the bra on her back, so I scratched
that area, too, and pulled the 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 fron her head to the top of her shorts.

The long, gentle strokes to her back side were obviously interrupted by
those damn shorts. I don’t know if she was exceptionally horny, or if she
truly enjoyed the tickling I was doing, but when I started to pull her shorts
down a little farther, she suprised 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 carressed
her smooth, round, white buns with a light, circular motion, and soon watched
her break-out with “goose bumps”. I finally removed her clothes and tickled
her naked body with strokes that tranversed 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 attempts to block my hand’s
paths by closing her legs, so I continued to carress 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
here. She placed one hand over her mound and her forearm covered the nipples
of her white breasts. I did not attempt to move her hand or arm, but instead
lightly massaged her face and shoulders, and ran my fingers up and down the
length of her arms. When I lightly carressed 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 progressed to 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
side 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 side, giving me a
beautiful view of those areas of hers about which I often fantasized. I ran my
fingers over her upper body and slowly made my way towards her small, white
tits. The fingers traveled in large circles around the breasts, with those
circles getting smaller and smaller until finally reaching her nipples. The
light contact made them stand to attention. Gradually, I began massaging her
breasts with both hands. My mouth was drawn down, and my lips contoured an
erect nipple. Her breathing began to increase in volume and rate, and it was
soon time to work my way south-ward. 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 the fleshy bud. The light touch turned into
gentle masterbation, and at this point I brought my mouth off her titty,
spread her legs and knelt between them. My fingers dabbled in the many 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. I reached in with my tongue, and tasted her. My tongue’s actions were
light and slow, but the pressure and speed increased with our sexual arousal.

In need of some attention myself, managed to remove my shorts as I
simultaneously practiced cunnilingus. My erection was rock-hard and needed to
see the inside of a woman. My tongue slowly made its way out of the folds 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. 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 penis to
her clitoris and spread the pre-cum around. The contact was intense and
forced me to pull away, lest I would have surely had an orgasm. After a short
period of recovery, my dick returned to his mission of penetration. Starting
at her clit, I placed the head into the labia and made the voyage down toward
her vagina. When the one-eyed monster was directly over her sex hole, she
wispered at me to put it in, but warned me not to cum. She was tight, and I
quickly met a resistance which seemed to cause her 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 me. I waited a bit, then attempted
re-entry, but again caused her pain. At this point she changed her mind, and
refused the vaginal penetration. 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 that act, she
agreed. My mouth returned to her folds. I fingered her cunt then spread the
lubricant in and around her sphincter. She moaned at the entering of my
finger into her very tight anus, but after repeated penetrations, the circular
muscle seemed to relax. I directed her to get onto her hands and knees.

We were 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 the beast into her back door. She flexed her muscle 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 he’d find, he slowly entered her. It
was warm, and dark, and very tight. The host moaned, though was it a moan of
pain, or pleasure…or both? My hips pressed against her ass, forcing the
member deeper into her. She placed her weight on her shoulders and reached
backed with both hands. Her right hand finger-fucking her cunt 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 contents, forcing its way into the
depths of her 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. At this point, our emotional immaturity was
evident, for we felt dirty, and a little embarrased by our sexual acts. We
caught our breath, and needed to shower. Not knowing when the parents would
be home, we showered by ourselves. It seemed a lonely shower for me. Little
did I know the this would be our last CONSENTUAL sexual contact…but that’s
another story.