Be Careful What You Fantasize About!
I have visited this site occasionally over the years and have read with interest the posts about family members masturbating together. My story is similar to many of those posts in some ways, but is also offered as a cautionary tale, things can easily get out of hand.
During spring break of my junior year in high school my parents went on a trip overseas. They left my older sister, Cheryl, a senior in high school, and me at home because we both had school activities and a short break. We were responsible kids and had taken care of ourselves before without incident.
The first morning home from school I slept-in late and awoke with that great feeling of freedom, knowing that I didn't have to get up, or go anywhere. I was warm and cozy in my sunlit bed and had an enormous morning erection. I pulled back the sheets and admired my cock, throbbing in time with my heartbeat. Closing my eyes I wrapped my hand around the warm, hard shaft and slowly began to stroke, fantasizing about the girl I was dating. It felt great and I picked up the pace as I visualized my girlfriend's tight little ass and pointy, firm tits. I had not seen her naked, yet, but had felt her up several times while making out, more than enough to fuel a young man's masturbation fantasy. I could feel myself approaching a climax when I heard my sister moving around out in the hall. My door was open, so I quickly pulled the sheets over my cock and rolled onto my side to hide my erection. Cheryl stepped into my room and, standing in the doorway, asked if she could come in.
'Sure,' I said as she walked across the room and sat down cross-legged on the foot of my bed.
She was wearing a long, terry cloth bathrobe and her hair was a little messed. She had obviously just gotten out of bed. I was a little irritated by her visit because my cock was still rock hard and throbbing, almost ready to cum. I'm sure my face was flushed and my breathing heavy.
'So, what do you want to do while mom and dad are gone? We've got the whole week off and I'm already kind of bored just thinking about sitting around the house. We could go to the mall or the movies. We could go to a concert downtown. We could..hey, are you listening to me?'
Honestly, I wasn't. All I could think about was finishing what I had started. I could feel pre-cum dripping out of my cock in a long sticky stream. My balls ached.
'Yeah. Uh, yes, of course.'
My sister looked at me closely and asked, 'What were you doing?'
'Nothing! What do you mean?' I said, blushing deeply.
'You were jacking off, weren't you? I caught you masturbating!' she said, a slight smile breaking across her face.
'NO! No, of course not!'
'What's wrong? Why are you so uptight? You think you're the only person in the world that masturbates? Everybody does it. Why deny it? I do it, too!' Suddenly she got this crazy look on her face and grabbed the sheet, pulling it down before I could react, exposing my still throbbing cock, pre-cum pooling on the sheet. I tried to cover myself with my hand, but there was no way to hide my erection.
'Oh! You were really close, weren't you?' she said, with a funny grin. Then, unbelievably, 'Why don't you finish? I can leave or I could stay and watch or, or I could masturbate too'. These last words trailed off until they were almost inaudible, as my sister looked down at her hands, clasped in her lap, the smile fading from her face. It was almost like she knew, even as she said it, that what she was suggesting would end badly.
My head was swimming with all kinds of thoughts. Warning bells were going off like crazy, but screaming louder than everything else was my cock saying, I WANT TO CUM! I was lying there naked, my hand already on my cock as I tried to hide it, pre-cum dripping out, almost ready to shoot, looking at my sister. Almost without thinking I started to stroke again as I rolled onto my back. By now there was so much pre-cum it was like lube and my hand was sliding easily up and down my shaft.
My sister's eyes glanced up at my cock and she just watched for a minute or two as I picked up speed. Then she reached down and untied her robe, letting it fall open, exposing her breasts.
Cheryl wasn't one of the really hot girls at school. She was cute, a word many girls hear as an insult, and ever so slightly chubby. I'd noticed in the past that her breasts were on the large side, but little else about her. I had seen her in a bathing suit, but never naked. Her skin was very pale and thin looking. Her hair was dark brown. Now, as her breasts came into full view, I noticed that they were large, creamy white with faint blue veins showing through her skin. They looked pillowy and soft, hanging down over a slight roll at her belly. Cheryl's areolae were large and indistinct, darker pink at her erect nipples, fading into lighter pink and then into the white of her breasts at least an inch out from her nipples.
She continued to pull her robe open as she watched me stroking my cock. I could see the top of her pubic hair come into view, dark and thick. Cheryl leaned back slightly and uncrossed her legs, spreading them enough that I could see her entire pussy, her lips swollen and brownish-pink. Though I had seen my share of porn, this was the first time I had seen a naked woman's body in person. It was electrifying!
My cock was surging in my hand as I stroked it madly, watching as my sister's right hand dropped into her lap and parted her lips, searching out her clit. She shivered slightly as she made contact with it and began to rub the base between her thumb and forefinger, her eyes never leaving my cock. Her breathing began to quicken as she kneaded the top of her bush with the heel of her left hand, rubbing her clit harder and harder with her right. I could hear the sound of her fingers working in the juicy folds of her pussy. I could smell her muskiness as she got wetter and wetter. It was mind-blowing! As she started to moan and make little gasping noises, I felt my orgasm rising from the pit of my stomach and deep in my balls. I thrust my hips into the air and stroked my cock hard, back arched, head forward. With a grunt the first rope of semen shot out of my cock and landed next to my head on the pillow. The second and third hit just below my shoulder and draped down across my belly. The fourth landed on my lower belly and the remainder ran down my shaft, over my hand and into my pubic hair.
Cheryl gasped loudly as I came. 'Oh my GOD!' she screamed, and then began to convulse. Her shoulders lurched forward causing her tits to sway wildly. Her right hand pounded her clit, her left driving hard into the top of her mound. Her head was thrown back, mouth open in a silent scream and eyes clamped shut tightly in a grimace of pleasure. I continued to pump myself up and down furiously, droplets of cum flying off of my hand and the head of my cock. Cheryl didn't slow down, she kept rubbing and rubbing, cum oozing from her pussy, into her pubic hair and out onto my sheets. She arched her back, throwing her shoulders back and her tits forward and screamed, 'I'm cumming AGAIN!' A small flow of cum ran down from between her already soaking lips and made a large, dark wet spot on my sheets.
Cheryl's head pitched forward and her shoulders slumped, tits hanging heavily and swaying with her deep, rapid breaths. Her hands stopped, her right still holding her clit between her finger and thumb. Occasional quivers, aftershocks of her orgasms, shook her body. I realized I was still stroking my cock and slowed the pace until I had stopped, seeing for the first time what a mess I had made and not caring in the least. Cheryl continued to look down at her lap.
Finally she released her grip on her clit and moved her hands away from her sloppy pussy. Without looking at me she swung her legs over the edge of the bed and stood up shakily. She closed her robe, back to me, and walked out of my room. I looked down and noticed that there was an actual puddle of liquid on my sheets where she had been sitting.
'Holy SHIT!' I muttered as I released my now softening cock and began to clean up.
There was no mention of the morning's events for the rest of the day. There was some tension in the air and my sister and I generally avoided each other. Time and time again, however, I found myself fully erect and fantasizing about her tits, about her soaking wet pussy, the smells and sounds. Twice more during the day I masturbated, and then again after I went to bed, feeling sick to my stomach with guilt each time.
The next morning I woke and laid in bed on my back, a full, hard morning erection begging for attention. I grasped it and was just starting to stroke when I heard a noise from my sisters room across the hall. I stopped and listened, instantly recognizing the sounds from the prior day. I could hear her panting, gasping and low moans. I could even hear the sounds of her wet pussy gushing under the attention of her fingers. Then I heard another, unfamiliar sound, a buzzing mixed with an occasion slurping sound. I lay there and listened until I heard sounds that I knew meant Cheryl was cumming. She tried to stifle them, but there was no mistake. She came once and the buzzing sound stopped. A moment later I heard her walk down the hall to the bathroom and start the shower.
I got up and walked across the hall into her bedroom. Her bed was unmade and there, in the middle of her sheets, was a large wet spot like the one she had made on my bed. Next to it was a large, pink vibrator, still glistening with cum. On the floor next to the bed laid a pair of white cotton panties. My cock was hard and throbbing. I quickly picked up the panties and wrapped them around my shaft, the head of my cock buried in the crotch. Then, kneeling on her bed I put my face into the wet spot and breathed in deeply while I began stroking my cock. I licked the wetness and tasted my sisters cum. I couldn't believe what I was doing but I couldn't stop either. I picked up the vibrator in my left hand and slid it into my mouth. The sweet, slightly metallic taste of her juices sent me over the edge. I felt streams of cum filling the panties wrapped around my cock just as I heard the shower stop.
I quickly returned the vibrator to the bed and dropped the cum filled panties on the floor where they had been, running back to my own room just in time to hear Cheryl opening the bathroom door.
What the HELL am I doing?! I thought as I sat on my bed still horny, but feeling sick at the same time.
I couldn't stop thinking about her smell, her taste, the sound of her cumming, the look on her face when I shot my load, the sight of her cum flowing out of her hairy pussy. I masturbated constantly for the next two days. There was still no talk about what had happened. In fact we talked very little and avoided each other except when we had no choice.
Then on the evening of the fourth day of break I was sitting in the living room watching TV. Cheryl walked into the room talking on the phone and sat down across from me. She was wearing her robe, having just gotten out of the shower. The sight of her in that robe caused me to immediately get a full erection. I was wearing a pair of thin gym shorts and had nothing handy to cover my lap. Cheryl glanced over and had to have noticed the larger bulge in my shorts. I thought I saw the same little grin that had been on her face the morning we masturbated together. I tried to ignore her and focus on the TV program, but I kept glancing over, fuelling my hard-on.
Cheryl was talking to one of her girlfriends and it soon became obvious that the topic was a boy at school that they both had a crush on. I began to listen to the conversation more closely as Cheryl's voice dropped and I started to hear an occasional word like Ass and Cock and Tits. I continued to act like I was oblivious to the conversation, but I was now listening intently. Cheryl was looking down and was barely whispering into the phone.
'Uh-huh! I agree! Oh, I would love to have his cock in my mouth. Can you imagine how hard and big he must be? I'd let him cum in my mouth. Really? Why not? I bet it would taste great. It makes me really horny to think about it. Yeah, me too! I'm already getting REALLY wet just thinking about him holding my tits in his hands while he cums in my mouth. Oh, stop it! It is NOT gross. I really want to try it.'
By now my cock was almost bursting out of my shorts and I knew I was breathing heavy. I could feel the flush in my face and the dampness of a pre-cum wet spot in my shorts.
'Oh God I'm getting wet. Are you going to cum?'
Out of the corner of my eye I saw Cheryl slightly spread her legs and switch the phone to her left hand. Her right hand dropped to her lap and snaked its way into the folds of her robe. The lights were off in the living room but the flickering light of the TV was enough for me to make out the dark patch of pubic hair that came into sight as her legs spread more widely. At that point I turned my head and looked directly at my sister. Her eyes met mine and she smiled, spreading her legs fully, exposing her hairy pussy and wet pink lips. She took her clit between her fingers and started to rub. I wanted to jack off so badly, but I just couldn't do it. I got up and went to my room, leaving her alone to masturbate with her friend.
A rush of confused emotions overtook me: I desperately wanted to go back and masturbate with her, but I knew it was wrong. I took my shorts off and sat down on the bed, stroking my cock to completion in record time. The climax did nothing to relieve my desire, or the conflict I had in my heart.
About a half-hour later Cheryl came into my room and sat on the foot of my bed.
'Why did you leave? I don't get you. You obviously came up here and jacked off. Why didn't you just do it with me? It's not like we're having sex with each other or something. I like it. You like it. It feels good. So, what's up?'
'I don't know. It just seems wrong.'
'Look, if we don't let this get out of hand, I can't see anything wrong with it.' Then, after a long pause, 'Are you going to tell Mom and Dad?'
'What? NO, of course not! Holy SHIT! NO!'
'Good. Cause I'd hate to have to tell them that you jacked off into my panties!' And, with that she stood, smiled at me and walked out of the room.
That night, I though a lot about what Cheryl had said and it seemed to make sense. I don't think now that it really did, but I was going crazy to see her naked again and to watch her masturbate.
The next day was a turning point. It started out okay, but man it got weird!
I took a chance in the morning and left my door open as I began to work my morning hard-on, making sure I made plenty of noise. Soon Cheryl appeared in my doorway, robe already open, her large tits topped by erect nipples, her dark, thick bush already showing signs of dampness. I continued to stroke as Cheryl came across to my bed and climbed in, facing the opposite direction, her legs spread wide to expose her full wet lips and swollen clit. She immediately plunged one, then two fingers deep into her hole, pulling them out sticky with her juices. She rubbed this mess onto her clit and began to masturbate in earnest. Her left hand went to her large breast this time and began to tug at her nipples. She stared at my cock intently and began to urge me on, 'Yes! Yes! YES! Stroke it. Jack off for me! I want to watch you cum!'
I couldn't hold back and shot stream after stream of cum, even hitting myself in the face with one. Cheryl wasn't far behind and came with a scream. With the first orgasm she squirted cum an inch or so out of her pussy and I watched transfixed as she continued to masturbate, cumming at least twice more before she relaxed into a heap, her heavy breasts rising and falling with her breaths.
My erection barely even softened as I watched her lay there, juices oozing out of her gaping pussy. Within minutes we were at it again. All through the day we masturbated, rested and then masturbated again. The sheets were soaked and the room reeked of sex. At one point Cheryl went to her room and returned with a box of toys including her pink vibrator. 'Want to suck it again?' She smiled.
We were both totally lost in the craziness of what we were doing, giving no though to the ramifications of our actions, or what might come next. As the day progressed, boundaries seemed to start falling. It was after the second or third time that we began to explore each other, tentatively at first, instead of just ourselves. Later in the evening I had two fingers deep in my sisters pussy, bringing her to a massive squirting orgasm. I licked her juices off of my hand as she gave me my first hand job, taking my load into her mouth and licking the cum off of her hand.
In the dark hours of that night lines were crossed that should never be crossed. We both passed out, sex-drunk, only to awake in the same bed to the horrible realization of what we had done the day before.
Cheryl clasped her robe around her naked, sticky body and ran out of the room. I heard her sobbing quietly before the shower came on and drowned out the sounds. I looked around the room, at the disheveled bed, covered in semen and Cheryl's cum, at the vibrators and at the empty container of lube. I was instantly sick to my stomach, dashing for the waste can where I vomited.
That spring break was over 20 years ago. Since then, my sister and I have hardly said a word to each other. She now lives in another state and is in an out of bad relationships between stays in alcohol rehab centers. My father is in prison for crimes that came to light after my sister left home. My mother has been released from prison, having served five years for her role in the same crimes. I run an adult web site, consider myself a sex addict, and can't stay in a relationship long enough to screw it up. I masturbate several times per day, almost always tortured by memories of my sister.
Be careful what you fantasize about, it may just come true.