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Waterskiing With Sis

Summer fun on the water because of a flat tire.
When I was a young teenager, 16 years old, my family had a ski boat, which we used on many summer weekends and evenings. We lived close enough to a reservoir that we would often go water skiing for a couple of hours when Dad got home from work in the evening. It was during one of these short, evening ski trips that the experience I'm about to tell you about happened.

While I was part of a big family, Mom, Dad and five kids, two of my siblings were much older and were off to college by the time I was 16: an older sister, in nursing school, and an older brother, studying to be an engineer. And Mom was way too fat to ski or put on a bathing suit, so it was usually my other older sister Colleen, who was 17, my twin brother Todd, Dad and me (John) who went water skiing.

Ever since I had reached puberty, I had the hots for my sister. I think this was more due to her being around than anything else, as she was on the pudgy side, and just plain average looking. She was blond, about 5'3", and probably 150 pounds. But, when you are 16, horny as hell, introverted as I was, even a pudgy sister can look tempting.

Not that I had ever got any relief from my sister. She was as modest as she was fat, and I could only imagine what her chubby tits looked like under the tight blouses she wore, and I was mesmerized when she wore jeans and the seam in the back would be up in her ass crack. But I never got to do more than glance at her butt.

I recall once sitting at the dinner table, Colleen on my right, and noticing that her blouse was pulling apart between buttons. I could just see part of her bra, and the top part of her breast. As small a peek as this was, it still provided jerk-off fantasies for me for weeks.

One summer evening of waterskiing, however, things changed for the better.

Colleen liked to waterski, but since she was so pudgy, she always wore a one-piece bathing suit, and most of the time had a beach towel wrapped around her. She never laid in the sun on the beach, but occasionally we would take a break from skiing, have a snack, let the boat drift for a while, and Colleen would sometimes stretch out on the bow. Since my Dad was there, I didn't even get to oogle her when she caught some rays on the boat. At best, I could just guess how big her tits were under the suit, and sometimes get a quick view of her butt and crotch, through her suit, of course, when she would bend over.

One evening, later in the summer, we finished our water skiing. As usual, one of the "twins" (meaning my brother or me) got off at the dock with Dad to go get the truck and trailer, while Colleen and the other boy stayed on the boat to drive it to the trailer. This evening, it was Colleen and me on the boat, and (as usual) Colleen just watched while I did the driving.

After we dropped Dad and Todd off, we waited for way too long for them to come back to the boat ramp. Finally, I saw Todd waving from the dock, so we motored back. Todd told us the trailer had a flat, and since there was no spare, he and Dad had to drive back to town to get the tire fixed. We were to just putter around close to the marina for the hour or so it would take.

I turned the boat around and headed out. We pulled a mile or so from the marina, and I turned off the engine and let the boat drift. Colleen headed to the bow to catch a few last rays. Being later in the summer, the air was cooling down fast, and the low sun did not do much to warm things up.

I opened a soda pop and sat in the Captain's chair, watching my sister. For once I could stare without worrying if Dad was watching. Colleen was on her back with her head toward me, so she could not easily see me without twisting her head around.

Even better, I could see a bit of cleavage down the front of her bathing suit. Not much, mind you, as the suit was fairly high-cut, and Colleen would be a small B-cup if she weren't fat, but it was enough to get a 16-year-old boy horny.

As I sat in the Captain's chair, I stared at that bit of cleavage, and slowly started massaging my cock through my bathing suit. Colleen could not possibly see this without sitting up, so I felt safe. It didn't take long for me to get rock hard, and soon the liner of my suit was becoming too tight for my prick. Not that I'm all that well endowed, but I was probably 6" long even then. So I pulled my suit leg and liner to the side, and let my prick poke out the bottom. I slowly stroked it, occasionally massaging my balls, and soon I was dripping pre-cum from the tip of my prick.

After a few minutes of sitting on the bow, my sister must have started getting chilly, because soon I could see her nipples poking up through the swimsuit material. This made me start stroking faster, still confident that Sis was oblivious to my staring and stroking. A couple of times I approached orgasm, but I would stop for a minute or so, just to keep the pleasure building. Besides, how often could I stare at my sisters tits and nipples, even through a bathing suit, for an extended period?

After perhaps 10 minutes of stroking, pausing, stroking some more, I was getting near the point of no return. Then I saw my sister reach up and scratch the side of her tit. I'm sure this was done without thinking that I might be watching, but as she scratched and her boob bounced back and forth, I hit the point of no return – I started cumming, shooting white streams all over, and groaning with pleasure.

At that young age, I had the (now envied) ability to shoot my cum quite a distance, and this time one gob flew the three feet or so to where Colleen was laying, landing on her swimsuit near the top of her tit. I don't know whether it was a gob of cum landing on her shoulder, or my incoherent groans that she noticed first, but, in any case, she bolted upright and turned around, just in time to see the last spurt of cum fly out of my prick.

I knew I was dead meat – Colleen sat there, mouth gaping in surprise (or horror), looking at my wilting prick in my hand. We probably stared at each other for ten or fifteen seconds before she said anything.

"What in the world are you doing!?"

"I'm . . . I'm . . . well . . . sorry, Sis . . ."

"I guess I can see what you are doing. Were you jerking off watching me?"

"No, I was . . . ah . . . I was . . . well, I guess . . ." I was still incoherent and embarrassed, and I started to tuck my prick back into my swim suit.

"Hold it right there! Leave your weenie out until we settle this!" I don't think Sis knew what she wanted to do right then, but just needed a few moments to think things through. "But grab that towel and wipe up your mess!"

I grabbed a towel, wiped up the floor and the dashboard where I had splattered cum. When I finished, Colleen said, "You missed one spot." The only spot I could see was the one on her swim suit, and I was in enough trouble without going after that one.

Colleen turned around, got off the bow and came and stood by me. "If you're going to make a mess, you have to clean it up! Now wipe off this spot before my suit gets stained." I was still immobile from fear, slowly turning into lust. Colleen grabbed my hand with the towel, raised it to her boob, and wiped the cum off her suit with her hand on top of mine. I swear to God that she rubbed my hand back and forth much more than was necessary, massaging her tit with my hand, and giving me another raging hard-on.

As Colleen let go of my hand, she looked down and saw my young, but very hard prick saluting her.

"My, oh my, you are hard again already! I think my baby brother has the hots for his sister! Do you find me sexy, John?"

Of course, I'm still nearly speechless from embarrassment and in a bit of shock that my sister has not totally freaked out at my cumming on her. Slowly I mumble, "Well, kind of."

"What do you mean, ‘kind of'?"

"Well . . . when you have your bathing suit on, and I can see your shape, I kind of like that. And your n . . . ni . . . nip . . ." I still couldn't bring myself to be this candid.

"My nipples? Are you saying you noticed my nipples sticking up through my suit? And that turns you on?"

"Uh, yea."

"Well, I think I'd better tell Dad he has a pervert for a son. I don't think he'll be very happy knowing you were jerking off over your sister, let along that you came on her."

"No, please, Sis, I'm sorry . . . I'll never do it again . . . Please don't tell Dad . . . I'll do anything for you if you don't tell Dad!"
"Well, anything can mean a lot of different things."

"I know . . . Sis, I'll do dishes on your nights . . . I'll stay out of your CDs . . . anything you want . . . Just don't tell Dad!" By now, my raging hard-on had shriveled into nothing, and was back in my suit. The thought of my Dad knowing what happened had totally wiped my feelings of horniness away. Obviously Colleen knew this scared me, and was perfectly willing to take advantage of it.

"Well, John, I don' really care about dishes and CDs right now. However, since you have agreed to do anything, you can start by taking your suit off so I can see your penis."

Of course, this was totally unexpected, so I just stared for a few moments. "Take my suit off?"

"Yes, pull your suit off. If you are going to jerk off watching me, I want to watch you, so take off your suit, and rub your prick to make it hard again."

I slowly dropped my suit, but didn't really need to stroke it, because the thought of my sister looking at my prick had me hard again by the time the suit hit the floor of the boat. Besides, by the time I had straightened back up, Colleen had reached out and grabbed my prick, and started stroking it slowly.

"Wow, that got hard fast! Does this feel good?"

The feel of my sister's hand stroking my prick was incredible. This was the first time a woman had ever touched it, and I think I would have exploded in about ten seconds if I hadn't just cum a few minutes earlier. "Yea, that feels great!"

I don't think my sister had ever had any sexual experience with boys at this point in her life. She was only 17, was pudgy and plain looking, and, as far as I know, had never been on a date. So, perhaps her response to my voyeuristic jerking was in part her own sexual drive and lack of release, or even just curiosity about boys. In any case, I wasn't complaining.

Sis sat down on the opposite chair, while I was still standing. This put her face just a few inches from my rock-hard cock. She continued to stroke it slowly, sometimes stopping to squeeze or shift her hand, while looking intently at my prick, in an almost stupor-like fascination. After a minute or two, I started groaning, as it was feeling so good. Sis looked up and smiled, then took her other hand and started feeling and massaging my balls.

"I'm going to cum again!" I said.

"No! Not yet! I don't want you to come until I have finished playing!"

Playing? Maybe she thought this was "play," but it was mind-blowing to me. "You've got to stop if you don't want me to cum!" I finally spouted.

Sis moved her hands to my belly and thigh, and watched closely as my prick twitched in excitement. "Well, then, perhaps you need to pay attention to me so your weenie gets a rest." I don't know why she calls my manhood a "weenie," but at that point I wasn't about to complain.

"What do you mean, ‘pay attention to you'?"

"I've made your weenie feel good, now you need to make me feel good. You can start here," with which she slipped off her suit straps and lowed the top, showing me in an instant those two pudgy tits I had been jerking off to for months.

I was back in stammer mode, "I . . . uh . . . I . . . uh . . . well . . . what do I do . . . ?"

Colleen just grinned at my discomposure, put her own hands on the sides of her boobs, lifted them up a bit, and said, "Why don't you feel these for starters!" I didn't need another invitation – I leaned down and put my hands under her tits, lifted them a bit and started massaging them. I had never imagined boobs were so soft! Soon I was running my thumbs around her nipples, which started to harden, and Sis started to moan a bit.

"Lick them!" she moaned. At this point I had to kneel on the floor, and tentatively started licking her nipples. After a minute or so, she told me to suck, so I started doing that. I guess I must have sucked too hard, as at one point she exclaimed "ouch," and pushed my head away.

"Sorry, Sis, I didn't mean to hurt you!"

"You've got to be gentle!" (Haven't I heard that from women many times since!) "Here, let's go sit where it is more comfortable." Colleen stood up and walked to the back where there was a bench seat. She started to sit down, then stopped and said, "I've seen all your goodies, do you want to see mine?"

For the third time in about fifteen minutes I was again a stammering, stuttering idiot, "Uh . . . well . . . I guess so!"

"Hah! You guess so! Have you ever seen a pussy before? I'll bet you have never even seen a bare tit before, have you, little brother?"

"No, only in some pictures."

"Where did you get pictures of naked women?"

"Well, my friend Sam's dad gets Penthouse, and sometimes we can sneak a look at it."

"Penthouse! That's the most disgusting magazine! They don't just show beautiful women, they do the beaver shots that make them look like sluts!"

"What's a beaver shot?"

"That's where the girl spreads her legs and they focus the camera on her pussy. Here, I'll show you!" With that Colleen peeled off the rest of her suit, sat on the bench seat, and spread her legs wide. "Come here and look, but don't touch!"

I stumbled a few steps to the back of the boat, sat down on the deck, and looked between my sister's legs. She is blond, and her pussy hair was also blond, but there wasn't much of it. As I looked, Colleen rubbed her hands up and down the insides of her thighs, and slowly started pulling her pussy lips apart. "Do you know what a girl's pussy looks like?"

"Well, we had some drawings in health class, and those pictures in Penthouse."

"Look closely – here are my outer lips," Colleen said as she rubbed them up and down, "and here are my inner lips," she said as she slowly pulled them apart, then flicked them back and forth, "and here is my love button," which she rubbed with her thumb, although, truth be told, I am not sure I could tell which part she was referring to, as my head was spinning. Finally, she pushed an index finger into her honey hole, and said, "and here is where boys like to put their pricks!"

Of course, by now I was sporting a raging hard-on, so hard it was starting to hurt. I think Sis sensed my stress, and told me to stand up. I stood up and she sat up, and grabbed my prick in her hand. She slowly moved her head forward, and tentatively licked the bottom of my prick. I just moaned at how good it felt.

Colleen moved her head back, pumped my prick a few times with her hand, then leaned forward again to lick the precum off the tip. "Tastes funny," she said, after which she leaned further forward and took my prick in her mouth. She first swallowed the head, then slowly moved forward along the shaft. I'm sure this was the first time in her life she had a prick in her mouth, so she simply moved her head back and forth. But, being a horny sixteen-year-old who had never had any sexual experience, that was all I needed.

"I'm gonna cum!!!" I moaned. Sis kind of mumbled "uh huh," without taking her mouth away, and just kept her slow in-and-out motion going. Within a few seconds I could feel an orgasm coming. I grabbed her shoulders to keep from falling over, and started pumping her mouth full of cum. Sis just kept up her motion, and let the cum dribble out of her mouth. I spurted half a dozen times and almost fainted from the pleasure. Sis started to slow down, then took her mouth off my prick and leaned back. She seemed to be tasting my cum to see if she liked it. After a few seconds she leaned over the edge of the boat and spit it out.

"Doesn't taste bad . . . a bit salty!"

Colleen now leaned back on the seat, her pudgy belly showing a couple of rolls of fat, her tits hanging to the side a bit. "Now you can return the favor, little brother. You've seen my pussy, have you ever tasted one?"

Of course, I had not, and was a bit apprehensive about it. "Sit down on the deck," she commanded. After I sat down, she spread her legs a bit and pushed her butt forward off the seat. "Lean forward, and lick me right here," she said, as she moved one index finger up and down her labia major. I stuck my tongue out and licked her where she told me to. I didn't taste much, but I could smell her pussy. It wasn't unpleasant, but it wasn't the "honey" that Penthouse letters said it was.

"Ok, now move your tongue up and down these," Colleen said, as she cocked her legs wider, but swung her ankles onto my shoulders. Her hand pulled her outer pussy lips apart so I could get to her inner pussy lips. I started licking up and down, and Sis started moaning audibly. That kind of turned me on, so I licked faster and started stroking higher and lower. "Ok, real fast here . . . ." she said, with her finger pointing to her clitoris. I started flicking it with my tongue. "Faster!" I flicked my tongue back and forth as fast as I could, while Sis started bucking her hips and moaning louder.

"Put your finger in my pussy!" Sis told me. This was another new experience for me, but I dutifully pushed my index finger into her cunt hole, and was surprised at how wet and slippery it was. "Ok, move your finger in and out and keep flicking my clit!" she moaned. I kept up my duties, licking her clit and pumping my finger in and out of her cunt. Sis moaned some more, and moments later I could feel her legs jerking on my back. Right then she grabbed my head and moaned "Stop!" I stopped both my hand and tongue, but left my finger in her pussy. She jerked a few more times, then started to relax.

"Was that you cumming?" I asked.

"Yep . . . that was really good . . . with a little training, you could become a master pussy licker!" She dropped her legs to the floor, and relaxed with a big sigh.

I sat back and looked at my sister, bare naked, legs spread, moist pussy staring at me. "Can I look closer?" I asked her. "Sure, if you want."

I grabbed her legs and pushed them upward. She got the hint and grabbed her thighs to hold them up, while I used my hands to spread and explore her genitals. I spread her pussy lips, found her little pee hole, and leaned forward and licked it – for which she rewarded me with a moan. When I spread her pussy hole, I was surprised at the little folds and flaps of flesh--while it was warm, moist and soft, it was nothing at all like the smooth inside of the "pocket pussy" that my friend's father had in a drawer.

Sis was very moist, but, again, not "gushing" like Penthouse authors always talked about. I leaned forward and licked around her pussy hole, trying to get a better taste. It tasted ok, but I still can't say (even to this day) that pussy tastes great. Not bad, and certainly worth going through in order to please a woman.

After a minute or two of licking around her pussy lips and cunt hole, just lightly enough to explore, but not enough to really get Sis off, I moved back and stared at her other private part, that little brown starfish below her pussy hole. I had always had a fascination (and still do, for that matter) with girl's buttholes, and having watched my sister's jeans ride up her crack many times, I was dying to see what the jeans were hiding.

Since Colleen had been in the water just a half hour earlier, she was fresh and clean, and I did not have any aversion to exploring her anus. In fact, I did not even ask her – I just moved my finger down and started circling her butthole. At first Sis tensed up a bit and I thought she was going to stop me, but when she moaned lightly, I new it was pleasure that she was feeling.

I felt around her anus, and pressed lightly on it, then rubbed up and down right over the hole. Sis moaned a bit more. I was turned on myself, of course, and was sporting another raging hard-on (oh, that I could perform like that now that I'm 50!). I started tonguing her pussy hole again, then slowly moved down, lightly flicking her perineum, and then, when my tongue reached her asshole, I circled it slowly. Sis was starting to really moan, and let go of her right leg so she could use her right hand to masturbate herself.

I flicked my tongue back and forth on her butthole, while she frigged herself. I tried to push my tongue into her butt, but it was too tight, so I inserted a finger into her pussy to get it all wet, then slowly slid my finger up her ass. By now Sis was bucking her hips, and I slowly moved my finger in and out of her asshole. Sis started cumming again, jerking her legs, and instantly stopping her frigging. I left my finger in her butt while she came off her orgasm. After a minute, she opened her eyes and smiled at me, and I slowly pulled my finger out.

"Wow, that was incredible!" she said, "I'm astounded you would play with my asshole even though you have never had sex before."

"Sis, I've watched your jeans ride up your butt crack ever since I started getting horny, and I've wanted to play with your asshole almost as long. I just never thought it would happen!"

"Well, neither did I, until a few minutes ago! Now, I think I need to do you one more favor, since you just gave me the most intense orgasm I've ever had. And I see your weenie is ready for action again. What would you like this time – handjob or blowjob?"

"How about I put it in your pussy?"

"Sorry, little brother, but I'm a virgin and I intend to stay that way for awhile. Besides, I don't know if playing with each other is incest, but having intercourse certainly is, and we could get in big trouble if we did that and I got pregnant. So, blow job or hand job?"

"Well, how about I put it up your butt? You can't get pregnant and it does not take your virginity, and I love your butt!" Sis obviously had to think about this a bit. I don't know if it was something she wanted to "save" for a special man, or she was scared of it or what.

"Your weenie looks pretty big to fit up my butt. I think it would probably hurt me."

"Look, we've got lots of lotion to use to make things slippery, and if it hurts, I'll stop."

Sis thought for a second, then turned around on the seat, leaned over the back, and said, "Ok, go for it!"

I grabbed a bottle of lotion, and said, "Spread your cheeks." Sis grabbed her butt cheeks and spread them, giving me a great view of her asshole. I squirted some lotion in her crack and right on her asshole, squirted some more on my hard-on, and finally some into my hand. I rubbed my prick a few times to get it well lubricated, then rubbed lotion around my sister's pudgy ass, and finally started rubbing her asshole.

I slowly inserted my index finger into her butt, withdrawing it frequently to get more lotion on it. It only took a few seconds to have my finger all the way in. "Squeeze your butthole, Sis." She did, and I could feel it on my finger. "Ok, relax it." She did this, and after a few more "squeeze, relax" cycles, I had three fingers in her butt.

"Ok, Sis, here goes. Have you ever had anal sex before?"

"Oh, come on John, you know I've never had any kind of sex before."
"So, have you ever put your own fingers into your asshole?"

"No, but I did shove a candle up there once. It felt good, but not as good as your fingers."

At this point the head of my prick was against her butthole, so I slowly pushed against her. "Relax your asshole, Sis." She did, and my prick slipped in. At first it was very tight, but after the head got in, it was more comfortable.

"Ow! That hurt at first, but it is ok now," Sis told me.

I'd like to tell you that I pumped her asshole for hours and the filled her rectum up with so much cum that it leaked out. In reality, I pumped in and out perhaps a dozen times, and then squirted what little cum was left in me after two previous orgasms. However, it felt just as good as those Penthouse letters say it feels.

"Did you cum?" Sis asked when I stopped pumping.

"Yea, I did." I slowly withdrew my prick from her asshole, not really wanting to quit. As the head popped out, her butthole shrunk closed again. I rubbed a bit more lotion on it, then grabbed a towel and wiped her crotch clean of pussy juice, lotion and saliva.

"There you go, Sis, you can put your suit back on."

"Ok. We'd probably better get back to the dock before Dad gets back." In reality, Dad needed a full hour, and our little sexual adventure probably only took a half hour, so we had plenty of time.

"So, you're not going to tell Dad what I did?"

Sis laughed, "What, and have you tell him that I gave you a blowjob and let you fuck me in the ass!? Don't be stupid, little bro. This whole thing will stay between us. And, don't expect any repeat, ok? This was fun, but we can't do it again, or we might get caught."

I did not quite see the logic of that, but was not going to argue. As it turns out, that evening on the boat was the only time we ever had any sexual contact. Sis let me see her tits a couple of times when she got out of the shower at home, giving me more jerk-off memories, but we never had another chance for such a romp again before she left for college.

Now it's many years later, and both Colleen and I have been married, divorced and have kids, hers grown and gone, mine living with their mother. Next month I go visit Sis in Seattle for a week. She has put on even more weight (probably weighs 180 pounds), but so have I, and I have to admit I have a bit of a fetish for those BBWs – big, beautiful women. So, who knows, maybe I'll be writing another true incest story soon. If not, I'll be imagining it.

*** end ***

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Comments(9)

TakeThosePantiesDown
Posted 25 Apr 2013 09:21
White hot - gave me a massive cock stand!
Kellett
Posted 10 Jul 2012 02:42
very nice
pooooosy
Posted 02 Nov 2010 07:33
very good and real one hotttttttttttttttttt
nivek_88
Posted 03 Jul 2010 00:50
nice, work out a sequel if you could
DrHouse
Posted 06 Apr 2010 00:54
Really great story, definitely enjoyed it. I'd love to see what comes of the visit
Jillicious
Posted 11 Feb 2010 14:17
Very hot story. calling it a 'weenie' made me laugh.
iceman
Posted 03 Feb 2010 10:17
Hot story.... now you need to continue where they fuck...
grassmanross
Posted 03 Feb 2010 07:14
Good story. I liked it a lot.
sweet_guy_46_xx
Posted 03 Feb 2010 02:30
Nice story
 

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