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fctrl+f to "bedtime" to skip the prologue and build-up.

I first met Anna about four years earlier. Some friends and I were out for a night of carousing in Chicago. It was a few years after graduating from college and we had decided to get together in the city to party and catch up. Anna was a friend of a friend who wound up joining up with our group as the night progressed. I wasn't immediately infatuated with her or anything like that, but I definitely remember being very curious about her from the moment I saw her. She was gorgeous, and on that evening she wore a very short bright orange dress that floated above and accentuated her athletic yet curvy frame.
I found my gaze drawn to her time and again throughout the night. She was a very beautiful woman with strong facial features. Her caramel Puerto Rican skin seemed to be glowing against the contrast of her dress. She seemed like a really awesome person. I was thrilled when I saw her talking with our mutual friend and I had good opening to engage her in some conversation. We chatted and laughed together for a bit, and in my mind I invented the notion that there was some mutual flirtation going on.
Following that evening, I began to see her more frequently, especially when our friend was hosting large gatherings at his place. We became fairly well acquainted and eventually "first degree" friends. We even began exchanging emails between the occasional meet-ups, and I became convinced that there was some mutual attraction going on. There were never any overt signals, except maybe one time when I thought I detected her gaze lingering upon me at one of the gatherings. Mostly she was just so nice and sweet to me, and seemed to enjoy our chats, and that was fuel my speculation.
We lived sort of far apart, but I began to entertain the notion that I could make my intentions clear, and maybe we could begin dating semi-long distance. In hindsight, it was always a pipe dream, and it became irrefutably so when one day I learned from our friend that she was moving to a more distant city for a job opportunity, and a driving-distance romance was no longer an option. After that, while we still kept in touch albeit far less frequently, I let my romantic notions about Anna drift from my mind.
Cut to near present day...
In the intervening period I too had moved to a far flung city. My time away went fantastically, but now I was returning home. Soon after getting back I was catching up my old friend, and he invited me to join him and some others for a group vacation that he was planning. I didn't have a job yet, and I had some money in the bank, and so I thought "what the hell, why not?" We would be going to a resort in the Bahamas to enjoy a week of surf, sand, sun and partying.
I didn't even think to ask who else was going because my buddy is cool and I knew he would have warned me if anyone disagreeable would be joining. I finally got around to asking him about the roster about two weeks before the trip, and he rattled off a list of about 10 names, and at the very end of the list was Anna. My heart skipped a beat. I was suddenly overcome with the wonderful feeling of renewed possibility. I would be close to Anna once again, and maybe, if I was the luckiest guy on earth, I could finally learn if she wanted me as badly as I had once and again wanted her. My head swam with delight at thought of it.
Departure day arrived and everyone was travelling from their various cities down to the Bahamas. As it turned out, my brief layover in Miami coincided with Anna's. Before I knew it, I was getting off my flight and texting her so we could meet up and board the flight to the Bahamas together. I knew she was with a friend, and I had not seen her in person in a very long time. I didn't know what to expect. When we finally saw each other across the terminal, and locked eyes, she smiled broadly and warmly, and waved to me. She looked as good as the first day I ever laid eyes on her, maybe better.
I savored the the view of her as I approached from across the terminal. Because I was far away to begin with, I could clearly take all of her in from head to toe without looking like too much of a creep. Her long toned legs were clad in comfortable black leggings for the day of flying. I obviously could not see behind her, but I remembered vividly what was underneath those leggings. I was already thinking ahead to what her pert round ass was going to look like in a bikini on the beach. It was as full and round as it was toned and taut, and I suddenly couldn't shake the thought of what it would like look naked and bouncing back against me. Her spaghetti strap tank top fit snugly over her full c-cup breasts and toned torso. Her jet black hair was pulled back tightly into a pony tail, and she wore hardly and make up. I was transfixed by her bright green eyes as she watched me approach her.
I walked up, smiling right back, and hugged her hello. It felt so good to hold her, even for what outwardly would have appeared as an innocuous hug. But that hug seemed to tell me everything I that I had wanted to know. The mutual attraction was there, and had always been there. I'll spare you the nuanced analysis, but my heart told me that she held it long enough and firmly enough to send a clear signal... or did she? Maybe that was my hopeful cock doing the talking. The devil's advocate in the back of my mind tormented me, and made me wonder if there really was any "signal" at all. We broke off, I met her friend, and we carried on about the business of traveling to our tropical holiday. But from this point on, my entire subconscious mind was mediating on every moment, and trying to determine how, when and where I would finally hook up with Anna... but hopefully not "if".
The day flew by. We arrived at the hotel and in no time at all we were all at the beach, drinking and having a great time. Later in the evening I saw to it that I wound up with Anna in one of the rooms as we began to get cleaned up for dinner. Our stuff was in the same room because we dumped everyone's luggage in just two rooms when we arrived and decided to settle in later. I thanked God that we had wound up alone together in the room. Others would be back soon. As we moved about the room grabbing our things and getting ready to head off to get to ready, there was a moment we passed closely to each other. Close enough to be able to perceive the delicate and tiny body and breath language that precedes intimate contact.
I can not adequately describe the ecstasy of the moment. Our faces were hovering near one another's. In that moment I knew I could lean in and kiss her. She was giving me an opening, there was no question about it. I let the moment pass. Right now you're probably thinking "what the fuck is wrong with you man?!". I know it seems crazy, but no there was no longer any question about it. She was definitely into me and I was now dead certain that we were going to hook up. I was suddenly feeling very confident, and even a little cocky, and I was enjoying the anticipation the feeling of a kind of power or control over her.
Cut to bedtime...
Now I know the fact that Anna and I wound up sharing a room is entirely unbelievable, but it is true. I could hardly believe my luck at the time. Her friend wanted to have a room to herself, so that helped, and although our names were on the same room I had offered to swap with another girl in the group who was also with a guy, to get to a more traditional and decent arrangement for the greater group. No one seemed to care or speak up when I made that offer. Of course I was fucking elated when no one bit, and I did not protest or press the issue. In hindsight, maybe everyone had been plotting on some vacation sex.
We were back from dinner, and everyone was tired from traveling and drinking all day, and was turning in for bed. Although I have said before that I was dead certain about the signals that Anna was broadcasting, and that I knew we would hook up, I was still nearly delirious with the thrill of actually being in this situation. All I could think at this moment was that I must have done some pretty good things in a past life. I listened to her getting ready for bed in the bathroom, imagined her narrow waste bent over she sink toward the mirror, her round ass poking out behind her underneath soft pajama pants, her full, bra-less breasts swaying beneath her thin t-shirt, her soft dark hair resting on her shoulders and back. In just a few more moments, all of that would be coming to get into the same bed as me.
It was dark outside and the moon was nearly full, casting a dim light across the greenery and water ourside the window. The lights were off in the room as Anna finished brushing her teeth and came to the bed. She turned the corner from the bathroom and I swear my face must have gone completely slack. She was wearing sheer silk pink pajama pants, and an almost completely transparent pink linen tank top. I gazed in awe at her exposed, astonishingly beautiful c-cup breasts. She looked at me with a playful smile and threw a teasing eye-roll as if to say "what, have you never seen a woman undressed and ready for bed?" Of course I had, but not Anna.
She got into bed next to me and we chatted and laughed quietly for another moment or so. Before long the conversation died off, and for then there was hardly any noise or movement. The wind blew softly outside the large double doors across the lush lawn and over the beach and ocean. I was lying on my side looking at her, and she was gazing off into the darkness at the ceiling, slightly away from me. I softly spoke her name.
"Anna"
She turned her head toward me and looked into my eyes. I gazed back at her for another moment, and the I leaned in and kissed her.
I feeling of finally kissing her soft, full lips was incredible. My senses were on fire. I taste of her lips, her smell, the feeling of her skin and hair; it was all too intoxicating. We began to kiss passionately and I reached up to caress her face. She moved her body closer to mine, and I let my hand wander down her slender side and over her free amateur pussy pictures hips and firm, full ass, and I pulled her into me. I moved down to kiss her jaw and neck. She rolled her head back and moaned as I kissed her and caressed her entire body. I didn't reach underneath anything right away. I was trying my best to go slowly and to make it last for as long as possible. But it was so very difficult.
I moved myself over her and looked down at her. Her dark skin looked so good in the moonlight against the white of bed linens. She raised her arms as I pulled her tank-top off over her head. I leaned down and kissed her delicate brown nipples, which were by this point raised firmly up with arousal. She ran her hand across the back of my head, arched her back, and moaned and sighed as sucked her nipples, kissed around her breast and gently bit her ribs.
I reach down to pull off her pajama pants. She was wearing a simple white thong underneath. The sight of her lying underneath me wearing only that white thong was almost too much. I had always imagined how fantastic she would look at a moment like this, and in fact she looked about a thousand times better than I could have imagined. Her majestic breasts hanging there above her toned belly, her white cotton thong stretched across her protruding pelvic bones. She was a heavenly sight. Suddenly I was kissing her again, but now with animalistic urgency. I kept kissing her as I reached down to pull off her thong. I felt the delicate patch of the few hairs that she had left over her almost completely bald mound, and I felt how wet she had already become.
At this point I was completely drunk with passion, and drunk with the feeling of power that one tends to get when a beautiful creature is yielding to your every move and advance. After her thong was off, I was dying to taste her pussy. I wanted to swim in the fucking thing, for Christ's sake. My restraint and delicacy was losing ground to my raw passion, and I could no longer contain my desire to the absolute dirtiest things that I could think of to Anna's beautiful naked body.
Now that she was fully naked, I took a moment to caress and kiss her body from head to toe. I could not get enough of her flawless, soft brown skin. I was on the side of her now, taking her in and kissing and caressing her everywhere. I cupped her breasts and stroked and gently fingered her pussy. She gasped and whimpered softly as my hands and tongue touched her. I moved back over her and positioned myself between her legs. I kissed her again, and then made my way down her chest, across her taut stomach to between her legs.
The look and smell of her sex as I contemplated her pussy was beyond describing. I was enthralled. I began softly kissing her sex, a bit freely at first, and then with a steady rhythm of tongue as she began to writhe and moan against my face. She was arching her back and bucking and grinding herself against my mouth, and was desperately grasping at the back of head and pulling me into her. I drew back and came up to my knees, and looked down at her. Her legs were spread wide around me and she looked back into my eyes as her breath slowed in the momentary pause. I continued to gaze down at her as I reached her her hips and began to roll her her. I was not at all finished tasting that pussy, but I wanted that beautiful ass right in my face as I did, and to be honest, I wanted to do something really dirty with her, to see her at her most vulnerable and exposed.
She did not hesitate in the slightest. She let me roll her onto her belly and I moved her legs to each side of me. I pulled her hips slightly into the air so that her ass was raised up, and her pussy was slightly pursed and fully exposed from behind. Her head was turned to one side her face pressed against the mattress looking over her shoulder at me with anticipation though her beautiful black hair that was fallen all over her face and back. I reached down with both hands and grabbed the back of her thighs right below her ass, and gently pulled up and apart as I thrust my face against her pussy and began to eat her again.
Her head rolled back and her throat pressed against the bed she cried out in pleasure. She reached underneath herself to my chin, stroking and pulling me into her as opened my mouth wide around her pussy whiles slowing drawing the the full surface of my tongue over her clit and labia, again and again. I let my nose nuzzle her perineum and her beautiful, tight brown asshole as I lapped at her pussy. She was moaning steadily now. She had reached up to knead and pull at her breasts and nipples, and she was rocking her hips back against my face. I renewed my grip on her thighs and the bottom of her ass and coaxed her hips and pussy even further apart as I continued to bathe her sex with my tongue.
I was lost in her pussy, held captive by view and feel of her ass and legs. I knew that if I kept going that she could orgasm, and fuck, by this point I was pretty sure that I was going to nut the second she or I touched my dick, if I could even manage to get to that point. Watching Anna moan and writhe against my face as I ate her from behind was about the hottest thing that I had ever experienced in my life at this point. I forced myself to draw back. She let her hips fall slightly and lay there on her belly panting softly and taking a moment to come down from the oral sex high. There were about a million things that I wanted to do to her. I thought about trying to slow things down, to make the night last. But I remembered that we were there for a week, and this was only night #1. There would be plenty of time to do whatever she or I wanted. But this, this was the first night. This was the culmination of a flirtation and desire that had been sparked over four years early, and that was now suddenly and unexpectedly coming to fruition. This was the breaking of the dam. "Fuck going slowly", I thought to myself as I hopped off the bed to grab a condom from my bag.
I slipped the condom on as she shifted to her side to watch me. I was so turned on by now, I knew I was going to need every ounce of control to avoid from coming the second that I entered her. I was glad for the assistance that the condom would provide on that front. I climbed back on to the bed. Anna said nothing, she just watched me with her beautiful green eyes and waited for me to continue to have my way with her. I learned later that it was a huge turn on for her that I took a firm lead, and did whatever I wanted to her. There was never any risk that she was going to protest, or say she didn't like what I was doing. In fact she had hoped that I wouldn't be timid or deferential, she had hoped that I would be the type of lover to take what I wanted from her.
I crawled across the bed toward her and leaned back down to kiss her some more. I had to get against her skin again, it was like crack cocaine to me at the time. I took a moment to gently kiss her hip, ass , flanks and tits. I kissed her hard on the mouth, and then I drew back and rolled her off her side back on the her belly. I guided her up on to all fours, and watched her hair cascade from her back down over her shoulders as she drew up from the bed. My eyes travelled from her hair, down her slender back, to the rise and expanse of her full ass, and her full tits hanging down underneath her. It was a fucking glorious sight. I reached down and grabbed her the back of her thigh, and with my thumb on her labia I pulled slightly apart as I held and guided my cock into her pussy with my right hand.
At that moment I was in heaven. It was probably the highest most triumphant moment of my life. What else was left. I was nude on my knees, cock hard as a rock, gripping the ass and hips of one of the most beautiful women I had ever encountered, hearing the guttural tone her grunt and moan as I entered her from behind. I started out slow for self-preservation, but we all know that slow and gentle doesn't really cut it in any situation, especially one like this. The language of her body had me picking up speed and power at a very rapid rate. She was arching her back and pushing back against me in rhythm. Finally, in a hushed and labored voice she spoke the first word she had uttered since we had started making love: "harder".
How I didn't explode right then, I'll never know. I collected myself, refocused, and pushed her hips lower into the bed, and began to alternatively grip her ass free naked amateur pics and pull her hips against me as I fucked her. My right hand reached up into her hair. I stroked it a few times, gave it a twist to draw most of it together into my hand, and than began to simultaneously pull while thrusting even harder and deeper into her than I had been up till that point. She cried out, and then broke into a sustained moan that rose and fell in rhythm with my thrusts. I released her hair and reached up under her throat and wrapped my hand around it, feeling the vibration of her moans in her throat, and forcing her chin upward. Her mouth was open, her eyes closed and squintng as her moans grew even louder and more urgent.
I couldn't take any more. I was seconds away from coming. I thought she was on the cusp too, but I couldn't be absolutely sure. I decided to go for broke rather than trying to hold out any longer. My hand was still at her throat, and I let my index finger slide up over her lip into her mouth. She instantly began sucking my finger and moaning hard with her now closed mouth. My left hand was splayed open across her has, with my thumb laying between her spread ass cheeks. I pressed gently against and massaged her ass hole with my thumb tip as she sucked my finger and as I continued to fuck her from behind. I moaned and practically yelled as my orgasm arrived. Both of my hands went to her hips to pull her against me as I began to buck and blow a load that I was honestly afraid would burst the condom.
Anna dropped her shoulders to the bed. Her left hand was at her tits, twisting and pulling at her nipples, and her right hand and flown to her clit. Thankfully, she had been close, and with just a few deft strokes of her hand at her tits and clit, along with our fucking, was all she needed to careen over the edge with me. I felt her pussy begin to rhythmically clamp down on my dick, and I watched her asshole twitch in concert. She was trembling and spasming back against me as I began to slow my stroke while my orgasm subsided. I felt on top of her and continued to grind gently into her from behind now that I was done. Her orgasm seemed to persist for a while, her breath still drawing sharply and her pussy still spasming on my dick as I layed there on top her, now totally spent.
After a moment or two I rolled off of her onto my back. I continued to try to catch my breath while looking out the window over the ocean. My mind wandered back to the question of what could I have possibly done to deserve being a tropical paradise having just fucked one of the most beautiful girls I had ever known. I looked back to Anna. She was still laying on her stomach, one leg straight and one knee drawn up, her hand running through her hair as she tossed it aside and looked back at me with now drowsy eyes. I was exhausted too, and we cleaned up and drifted off to sleep together in each others arms.

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