With my younger sister and I being as competitive 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.
We were teenagers 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 on 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 from 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 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, 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 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 attempts 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 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 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 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 masturbation, 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 whispered 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 embarrassed 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 then this would be our last CONSENTUAL sexual contact… but that’s another story.