A fond recollection of a young man's trip to a Mexican resort with his sister and her best friend.
The best memories of life are from those unexpected moments when a friendship with a girl develops into something unbelievably intense, culminates in the physical, and then maintains that pleasant level for a couple of years until you both move on. The memories last forever, and you always have that special gleam in your memory about the beauty of it. Most people have those memories -- or at least I hope they do. It's an amazing thing.
In my case, though, it happened with my sister.
The summer before my senior year in high school my parents took Karen, myself, and a friend of hers, Lisa on a trip to Cozumel, Mexico for a ten days. My parents are fairly well-off, not extravagantly wealthy but doing well enough to afford occasional luxuries. Karen was almost 16 and had developed into a gorgeous young woman. Her arms were long and almost thin, but her body was curvaceous and toned. She had long amber hair and this amazing laugh that made her entire face light up. I knew that she was beautiful, both inside and out, but my feelings towards her were not consciously sexual. Instead it was more of a quiet pride in the intelligent, happy, and beautiful young woman she was becoming.
We had been at the resort in Cozumel a few days when our parents decided to go in to town for the day to shop, eat, and basically have some mom-and-dad alone time. We were all old enough and responsible enough that they were comfortable leaving us alone at the resort for the day. And honestly I wonder if they suspected something might happen and just didn't care all that much. Our parents had always made sure we were knowledgeable about human sexuality, and figured that was better than us getting bored and getting in trouble in a more public way.
They knew it was our vacation too, after all. And I'm pretty sure they also had wild adventures when they were our age.
So the parents headed into town early in the morning. We all woke up about an hour after they left and put on our uniforms for the trip, which in our cases happened to be bathing suits. Karen looked amazing. She wore a lime green bikini that was just *this* side of being too small. Long hours beachside had caused her to get a great tan that made her cheeks flush red whenever she would laugh. Lisa wore a bikini that was about the same size as Karen's but solid white, contrasting nicely with her dark, long, silky brown hair.
Before the trip Lisa and I had this relationship that bordered just this side of being confrontational. She was hot, but came across a being slightly arrogant. Further, she was my sister's best friend, so there was this unspoken rule that she was off-limits. In retrospect I think this came from my sister; I think Karen was attracted to me on a forbidden level, but just couldn't let herself admit it -- even to herself. So instead she sent off subtle clues of jealousy that became slightly more pronounced whenever Lisa was around. You're hypersensitive to those things about girls when you're that age, so to make sure Karen knew that I got the message I would joke around with Lisa in kind of a passive-aggressive way. Lisa would always return the favor.
But after we were all forced to be around each other for a couple of days the dynamics started to change. There was an edge to everything that was very pleasant and relaxed. The biting comments stopped almost completely, and when they did crop up they were not as harsh. We just laughed, swam, and basically had a great time with each other. And hell, I was 17 and enjoyed every moment of being around them, watching them move and laugh.
We ate breakfast that morning together, watched TV for a bit and headed to the pool. After a bit of haggling with the bartender, and with the help of some "hey I'm going to talk to you with my arms pushing my boobs together" from Karen, we managed to to get served some mimosas. Since we were all lightweights it only took a few before we got a nice morning buzz. After a while we got bored and headed back to the hotel room. The girls wanted to check out the shops that were across the street, and didn't want to walk around in their bathing suits.
We got back to the Karen and Lisa went into the bathroom to change. I could hear them talking and giggling softly, but my eyes were focused on one thing of particular interest: they left the door open. After a couple of minutes I got up to go talk to them. Yes, they were in the bathroom, normally a private domain. But the door was open, and… there was something in the atmosphere. Something exciting. Something electric.
It just seemed like the right thing to do.
So I got to the bathroom door and opened my mouth to talk when I saw Karen standing there, doing something with her eyelashes in the mirror. Topless. She turns to look at me with a slight grin, one eyebrow raised.
"Uh, do you need something, Brian?"
"No, I, uh, just wanted to see what you guys wanted to do later." Most brilliant comeback of all time.
"Well, I don't know Brian, did you have something in mind?" Lisa asked. She was sitting on the counter on the other side of Karen. She was also looking at me with a gleam in her eye.
Something about their attitudes caused me to snap back into my typical self. I took a stance like a gunfighter and said in my best Texas drawl:
"Well I dunno there little buckaroos, but I think this is a good place t'start!" With that I whipped the camera I bought for the trip out of my back pocket like it was a six-shooter and held it up in front of my face.
"Brian!" They both screamed, laughing.
"Brian, NO! You can't do that!", Karen said. But she didn't move to cover herself and she certainly didn't look like she wasn't having fun. "I don't want anything showing up on the Internet!"
"So you don't care if I take it though, right?" I thought.
I locked eyes with her and hesitated for a moment.
"I tell you what, sis. We do this and you can have the memory card when I'm done. What you do after that is your business."
"Oh my God, I can't believe you want to do that," she said.
So before she could say another word I snapped a picture of her.
She's standing there, laughing, one hand partially covering her mouth, her cheeks flush. Her long hair is still wet and golden-dark. And her breasts are perfection like no plastic surgeon has ever been able to achieve: high, full, round. Sunlight is coming in from the window to the right of her, highlighting her hair and her bright green eyes. She laughs. She glows.
Seeing Karen like that caused a reaction in me that was deeply physical and surprisingly emotional. I felt a love for her that took me completely by surprise. What I wanted to do was to pick her up, take her into the bedroom, lock the door, and completely have my way with her forever and ever, Lisa and society be goddamned. It was passion, but passion based upon the friendship that we had developed and the love we had shared our whole lives.
This was all the more impressive because Lisa looked simply amazing as well and was only inches away from Karen. Her white bikini top was holding up these magnificent breasts, smaller than Karen's but no less gorgeous. She was wearing a green floral-print wrap, sitting on the counter with her legs crossed. The wrap fell open almost all the way to her hip, and the effect was sexier than if she had had nothing on but her bikini bottoms. She was leaning back on her hands, the position causing her well-toned abs to show.
Even with that vision of beauty sitting a few feet away there was little room in my mind for anything other than the laughing, elfin face that I'd known my whole life. I wanted to take her. *Now.*
But things weren't yet at that point. All of a sudden I found myself painfully erect. I hadn't even been aware of it happening. My cock was pointing straight up, held back by the lining of my swimming trunks. I both did and did not hope that they could tell. They probably could.
Lisa looked up at me as I pointed the camera at her.
"So, Lisa, are you playing to?"
"I don't think so, Brian. Whatever you do with your perv sister is your business!" Something in her face and the way she said it didn't quite match her words. Or maybe I was just being hopeful.
"Oh come on, Lisa! Don't be such a prude!", Karen said, surprising me a bit.
Lisa looked over at her. For a few seconds they exchanged gazes. Then Lisa started blushing deeply.
"Oh here we go," I couldn't help but think.
She turned to look at me, reached around behind her neck, and started untying the bikini string.
"Wait," I said. "Stop right there."
She looked at me with a quizzical look on her face. I held the camera up and she seemed to understand: her current pose was perfect. I snapped a picture of her, her big brown eyes staring right at the camera, her hands behind her neck. This caused her already perky boobs to rise even higher. Her long hair was held back in a ponytail, highlighting her slender neck.
"Ok, go ahead," I said.
She paused for a second, then untied the strings to her top and tossed it aside.
"Why don't you stand up and lean against the counter?" I asked.
So she does. Whenever I run across the word "statuesque" I always think about Karen. But the word "voluptuous"... That describes Lisa perfectly. She was an inch or two shorter than Karen, but had more curves in some very nice places. Her hips were slightly wider, but her waist was about the same size.
I got a few more pictures of her, suggesting poses. I then turned back to Karen and did the same. We're laughing and cutting up, they're trying unsuccessfully to be all serious and sexy for the camera, all of this happening in this pleasantly cramped bathroom.
After about ten more minutes of this Lisa says "Ok, Brian. Now it's your turn."
I feigned ignorance. "What do you mean?"
"I think she means she wants to take pictures of you, dummy."
"Oh, ok." I hand the camera over and strike a pose.
"Oh no," Lisa says. "Not like that. You get to see us, we get to see you."
"But I didn't get to see all of you!" I was enjoying the hell out of this, but wasn't going to let them know that.
"Come on, Brian, you show us yours and maybe we'll show you ours," Lisa said.
So with that I untied the drawstring to my trunks, slid them down to ground, stepped out of them, and stood up straight.
"Oh my God," Karen said, staring straight at my cock. Now, I'm no slouch in the cock department: 7 inches from tip to balls. So I tried not to grin like an idiot at those words, and managed to just gently smile. I was also very aware that my cock was standing at full attention, being admired by two topless teens.
"Mmmm ok, now pose!" Lisa ordered, and I did. She would suggest poses, then Karen would, then Lisa again. The whole time I was painfully aware of how close they were to me.
After a few minutes Lisa lowered the camera.
"Hey, why don't you guys pose together? You look so cute next to each other."
I couldn't tell if my mouth dried up or I started salivating. Either way, my heart was thumping in my chest so loudly I could hardly think.
Karen let out this embarrassed laugh and looked at me. I smiled, shrugged, and moved in closer to her.
We did some fairly innocuous poses, both of us pretending this wasn't turning into something more. Then she turned around and I got behind her, my cock nestled in between her ass cheeks. I had my hands around her waist, and could feel the tight muscles of her abdomen. And something else, as well: she was trembling.
That threw me for a loop. There was no way in hell I would do anything to hurt this beautiful creature. So instead of grabbing her like instinct told me to I instead gently stroked her belly with my fingertips, then her back. She was still trembling but seemed to relax somewhat. She bent over a little bit more and put her elbows on the countertop.
"That feels nice," she sighed.
I continued to lightly caress her back. She relaxed some more and then did something that almost made me come right then and there: she pushed back at me and began slowly, very slowly, moving her ass up and down.
It was at this point that Lisa put the camera down. My attention had been focused like a laser on Karen and Lisa's movement brought me out of it. She laid the camera down on the counter, looked directly into my eyes, and walked up next to me. She put her hand on my lower back, and then just like that we were kissing.
There are two images from that day that are embedded in my memory like they had been burned there with a branding iron. The first was of Karen's beauty while she blushed and laughed as I took that first picture of her. The second is of Lisa walking up to me before we kissed. She was topless, wearing nothing more than her bikini bottoms, a floral wrap, a beautiful tan, and a ponytail that went down below her shoulder blades. I'll never forget the way she looked as she moved, graceful and determined.
I let go of Karen and turned my attention to Lisa. She put her arms around my neck and pressed her breasts against my lower chest, her belly mashing my cock against my abs. We kissed deeply for a moment before I heard Karen move. I broke the kiss, turned to Karen, and leaned into her ear.
"I am going to kiss you now," I whispered.
And I did, and… Wow. We could have powered a small city with that kiss. At first it was tentative, then it grew in strength and intensity. Our tongues battled and she let out this girlish moan that was so sexy I almost lost it then and there.
She draped her arms around my neck and pulled me in close. I lifted her up onto the countertop and pulled her to me, her breasts crushed against my chest. My kisses moved to her neck, at which point she looked at Lisa who obligingly moved in. They exchanged a kiss while I moved my hands to Karen's magnificent tits.
She wasn't trembling any more.
"So have you guys done this before?" I ask.
"Not with you!" Lisa exclaimed.
"Good enough," I thought.
Karen's right breast was now pressed against Lisa's left one, nipples touching. I leaned down between them and begin flicking my tongue over both nipples. They both let out small moans and look down at me. I looked back up and grinned, my tongue sticking out.
It really doesn't get any better than that.
I kissed my way back up, this time to Lisa's neck.
Then I nearly jumped out of my skin as I felt a hand lightly touch my incredibly sensitive cock. They both felt me jump and everything stopped for a moment as we shared a nervous chuckle.
It was Karen's hand. My sister's hand. And I was happy for it.
Slowly she started to move it up and down. I moved my hands up each of their inner thighs and began rubbing the mounds underneath their bikini bottoms. Karen moaned and grabbed my shoulder for balance, slightly spreading her legs. Lisa leaned back against the counter and thrust her hips forward, rocking them back and forth. The aroma of them started to fill the tiny room. I slowly worked my way under Lisa's bikini bottoms.
Hopping down Karen pulled me by my cock towards the bathroom door.
"You guys follow me," Karen says, leading the way to the girls' bedroom. They fell onto Karen's bed.
"These need to go," I said with a grin. I untied Lisa's bikini bottom and threw it on the floor, then pulled off Karen's and discarded it on top of Lisa's. Lisa's pussy was covered with a light brown strip of hair that was just barely there. Karen's was almost nothing to speak of: light blonde hair that was difficult to see, the skin under it untouched by the sun. I kissed my way up Lisa's magnificent leg, up her thigh, and deeply inhaled her aroma. It was a beautiful smell. Karen rolled over on her side and began kissing Lisa again, massaging her breasts. I kissed Lisa's pussy, causing her to gasp and spread her legs further. I licked her pussy from bottom to top as she thrust her pelvis against my face, moaning loudly.
"Oh my God, yes," she panted. "Yes!" she almost screamed as I began working on her clit. Her panting and exclamations quickly became harsher and more intense. I reached up to play with her tits and found one already occupied by one of Karen's hands. I slid my hand between her hand and Lisa's tit, grasping Karen's fingers tightly between mine so she wouldn't take her hand away.
"Oh yes, that... Yes!" Lisa screamed. I could tell she was very close. I quickly licked my middle finger and stuck it inside her. Her chest suddenly jerked downward like she were doing a stomach crunch and she began to shudder, her hips powerfully moving up and down. Her mouth flew open and she began taking deep, fast breaths.
It was *gorgeous*.
I continued eating her as her hips jerked up and down, coating my mouth and jaw with her juices. After a minute she calmed down, letting out little shudders every once in a while. I slowed down my efforts until they became gentle kisses. She looked down at me, panting, her eyes now open. She had this peaceful look on her face before smiling. She then looked over at Karen, then back at me.
"Do that to *her*!" Lisa said, grinning.
I stood up, looked to Karen for any objections, found none, and gently pushed her onto her back. Our eyes never left one another's: somewhere I was still unsure about this foray into incest, and I was sure she was as well. I wanted to give her a chance to back out if she needed to.
We kissed deeply, her hands pulling my head in to hers. I kissed my way down her neck, eager to get to her perfect breasts. I alternated kissing and biting each of them, her breathing getting heavier. Finally I kissed down her tanned belly before scooting off the bed entirely, between her legs, my hands running up her sides to grasp her tits.
We locked gazes, both of us realizing that this was the point of no return, if that point hadn't already been reached. The look on her face now was quite different from what it was when I took that first picture of her. Now her eyes were half-closed, glazed, her mouth slightly open. She looked excited, yes, but perhaps a little bit afraid. I gently massaged her erect nipples, aware of Lisa watching us, sensing that this was an important moment. Karen's pussy was close enough that I could lean in and lick it if I wanted to, and I did want to. But only if she did: our relationship was far too important for me to push things.
But still, I wanted her. So I compromised with myself and gently blew on her pungent lips, my eyes never leaving hers.
That did the trick. Karen pulled her knees up towards her chest, closed her eyes, and started gently panting. She put her hands on top of mine, crushing her own tits.
That was all the signal I needed. I leaned in and kissed Karen's almost hairless lips. As soon as my mouth touched her pussy she started taking in quick, vocal breaths. She removed one hand and grasped the back of Lisa's neck, pulling her in to share a kiss, muffling her increasingly loud moans. As I worked on her clit and nipples she broke the kiss and started moaning in Lisa's ear, holding her tightly against her while Lisa kissed her ear and neck.
"Brian! Yes!" she shouted as I continued to work on her clit. I felt her pull Lisa closer to her. Lisa rolled on top of Karen, Lisa's legs holding Karen's high and wide: I now had two pussies directly in front of me. I continued to firmly lick Karen's clit, then took a finger and worked it in to her. "Oh yes, so good, oh my God, yes!" she panted. Her moans then became muffled and started coming from her nose: she was kissing Lisa again. I licked her clit with more force and slid another finger inside of her. Suddenly Karen's hips began jerking violently upwards and she screamed into Lisa's mouth, her hand slapping on to my upper arm and grasping it so tightly it hurt. I felt her pussy start to contract over and over around my penetrating fingers. Her loud panting stopped completely, and her entire body shuddered powerfully. Her orgasm peaking throughout her body, she thrust her legs downwards with uncontrollable force.
In fact, her legs contracted with such sudden strength that it knocked Lisa completely off balance and she sat down with her full weight right on my head.
"The fuck?! OUCH!" I exclaimed, my mouth muffled because, well, someone was sitting on my head and my mouth was full of pussy whether I wanted it right then or not. Now, Lisa was not a big girl by any means, but having *anyone* sit on your head right then just kinda sucks. Lisa immediately realized what had happened and jumped up, looked at me and started laughing her ass off while I sat up and rubbed my neck. Karen was still coming down from her orgasm so had no idea what had just happened, and was actually starting to look slightly pissed off, like we were laughing at her. When we explained it to her she started giggling at what she had done, then we all laughed together for a minute before everyone took a deep breath.
"So, now what?", I asked Karen, kissing the inside of her thigh.
"I dunno, big brother, now what?"
So I stood up and moved between her legs.
"Is this ok?" I ask.
"It's ok, we're on the pill," Lisa said, plopping down on the bed. I don't think there is a combination of six words in this language that are more beautiful.
Karen looked up to me, not saying anything, her mouth slightly open. I wasn't going to let Lisa speak for Karen, though, so I looked at her again to make sure we were going some place she wanted to go. She was probably asking herself the exact same questions I was asking -- or had asked, anyway. By that point all questions were gone from *my* mind.
She gave an almost imperceptible nod. I grabbed hold of my cock and aimed it home, and slowly slid in all the way to the hilt without having to stop even once. She was incredibly wet, and hot, and tight, and amazing. Fucking amazing. Fucking now. "Brian, is this ok?" she asks in my ear, a whisper. "I can't think of anything more ok", I whisper back, both of us unheard by Lisa. This is raw. This is powerful. This is right. This is good. This is me, fucking my *sister*. Wrong? NO. This is me, loving her. "I. Love. You." This is us, brother and sister, together. Kissing, touching breathing, fucking. Green eyes. Panting. Tan lines. Breasts bouncing. Holding. Fucking. Thrusting. Legs spread high and wide and look at this girl this woman look at her looking at me moaning because of me dripping so fucking hard. For *me*.
Coming. Now. Hard.
"Oh my God Karen I'm going to cum yesssssssss," I moaned, deep and throaty. I was too worked up to last very long: no apologies. I thrust myself as deeply as I could, feeling her vagina tighten around me, her cervix pressed against the head of my cock. Filling her, feeling my cum fill her warm, wet, tight pussy. I kissed Karen, her moans and her tongue filling my mouth. I then collapsed on top of her, my head falling between them.
We all quietly relaxed for a minute, me resting on my elbows, my ears ringing with the intensity of it all. Karen was playing with my hair and Lisa was tracing patterns on my back. Karen was contracting her vaginal muscles around my still erect cock. We kissed each others cheeks and lips, savoring the moment and feeling incredibly… together. Happy.
Normally it took me a few minutes to get hard again, but that wasn't going to be the case today. I was still rock hard inside of Karen. I looked over at Lisa.
"So, what about you?", I asked.
"What about me?" she asks.
"Do you want a turn?"
She paused for a second. "Well, YEAH."
"Ok then." I pushed myself off of Karen. She moved up to the top of the bed, sitting against the headboard with her legs spread and a pillow behind her. Lisa scooted over and laid down, her head about six inches away from Karen's pussy.
I moved over her.
"Do it, Brian," Karen said.
I put my hands on either side of her shoulders in a push-up stance as she reached down between us to guide my cock. She lined it up and rubbed it around for a second, then after two or three strokes I was in.
She felt amazing. Different. Her vaginal muscles didn't have as much strength, but she was tighter deep inside. I slowly worked in and out of her, our breaths getting deeper and almost synchronized. She grabbed my sides to pull me harder into her, saying "yes" over and over.
"Fuuuuuck," she moaned, my thrusts getting longer and more powerful. I slammed my cock into her, hitting her clit with every penetration. "Yes, God, yes!" She locked her legs around me, her heels bouncing against my ass and pulling me into her with every stroke. "Oh my God, Brian, that feels… soo…. gooood." I thrust in and out of her, our rhythm powerful and steady.
After a few minutes of this I slowed down and kissed her.
"Why don't you roll over?" I asked.
"Ok", she said. So I started to pull out. But that was no good. Pussy was calling. Ok, back in, just for a tease. So I slid back in. Ok, now I'll pull out. Oh but wait, just once more. Ok, now out. And now in. And now we were in a rhythm again, her moans getting louder and louder. I looked up at Karen and saw that she was gently stroking herself. She blew a kiss at me. I smiled and slowed down, and pulled out.
Karen rolled herself over onto all fours, still in between Karen's legs. They looked at each other as Karen reached up and stroked Lisa's hair. I moved behind Lisa to line myself up. At that moment Karen looked straight at me and grinned.
I grinned back, grabbed Lisa's waist, and thrust. Lisa gave a mighty "unh" and pushed back. We quickly got into a rhythm. Lisa held her head up and took one of Karen's nipples into her mouth. Karen held the back of Lisa's head and bit her bottom lip.
I fucked away at Lisa, her black ponytail bouncing back and forth, her back muscles rippling underneath her lightly tanned skin. She pushed back into me and let out a louder moan when Karen reached up to play with Lisa's nipples.
After a bit of this Karen got up and indicated she wanted to get underneath Lisa. Lisa lifted up an arm to let her in. Karen slid in, her head near where I was still drilling Lisa, Karen's legs spread for her friend. Lisa immediately dropped her mouth onto Karen's pussy, her ponytail falling forward onto the bed. I felt Karen start to play with Lisa's clit, her fingers occasionally brushing against my cock. I plow into Lisa's pussy, grabbing her hips and fucking her with increasing force. I can feel it building, but don't want it to happen for a long time.
I looked down and saw the girls' discarded bikini bottoms on the floor. For some reason that was all I could handle. Bam. I'm coming in Lisa, completely out of nowhere. I moan again, this time louder. I feel her pussy muscles clamp down against me, milking the cum out of me. She moans louder, then moans loudly into Karen's pussy, coming again.
I pulled out of her and we all collapsed in a tangled heap on the bed. We were sweaty and exhausted and sticky and oh so very satisfied. We rested for a few minutes before going and taking a group shower: also a crowded experience. There was no fucking around in the shower (well, maybe a little), mostly quiet conversations and smiles.
We didn't get a chance to do that again. We went home later that week, and our parents were annoyingly present for the rest of the trip. After we returned home there were a few other sordid adventures, but none were as emotional as that first one. Karen told me later that she and Lisa had been talking about me, and that she really did go into the bathroom to change, but she just kinda-sorta-accidentally-on-purpose left the door open.
I did give the memory card to Karen. I assume she still has the pictures; I only saw the full set once, and respected her wishes around that. I do have one picture, though: the first one I took. I insisted on having a copy of it, upon pain of death if it were to make it onto the net. I still have it, and cherish it. That laugh, those eyes, that beauty. The picture is almost unnecessary, though. I still remember her standing there as clearly as if it were earlier today.
And no, you can't see it.
Every sexually active man has a memory similar to this. Some may admit to it, some won't. But women, if you ask your boyfriend or husband if he has such a memory he's very likely going to say yes. These things stick with you. They keep you warm as you get older, when times are dark and you it helps to remember that things can at times be very, very good. But keeping those memories do not mean that they don't love you, or that they want to relive the glory days (at least if they're wise). It's just a good memory. The best of memories.
And Lord knows there aren't enough of those in life.