Flashbacks - New Years

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A New Years Shemale Party.
3.9k words
4.45
47.4k
16

Part 1 of the 5 part series

Updated 06/07/2023
Created 12/05/2015
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You may be interested in the rest of the series, with actual plot and boring facts about my life and how I ended up living in a polyamorous family. Or you may just want to read this one. It doesn't contain spoilers, necessarily – but what I am now is not who I was then, so you will see so changes.

Readers choice.

This is my life, and after New Years 2015 I realized that I wasn't restricted in any way from a timeline – just write down events and let people hopefully enjoy them.

Just to keep things sane, the stories will be "Flashback –New Years", and you'll figure out that it can be read as a standalone. Another thing. This is written in a distinctly different style than the stories that are actual flashbacks. I hope you like the writing, its just another way of differentiating the past from present. One more thing, one final note.

E flat. E♭

"Come – in the Bahamas." - Crazy People

"Heaven is a place on Earth" – The Bangles

We were all down in the Bahamas for New Years, ushering in 2016. After two days of partying and drinking on the beach, watching our group and others play in the sand and at the pool, we were ready. I planned to be with Lauren for the night. I was looking forward to staying awake way after midnight. If someone else in the family wanted to join us, though, we weren't going to say no.

Lauren was a beautiful redhead, with a gorgeous pale face with glittering emerald eyes. She could look both severe and vulnerable at the same time.

Her body was inhuman. Her hips and ass were huge, in the best sort of way. Her ass was round, curved; the classic bubble butt. A joy to look at, walking, sitting from behind, all painting worthy. Just perfect. But she needed to get specially fitted clothing, because she was so Barbie-dollish. Add to that her huge cock, and she was always perfectly dressed. Just a LITTLE too tightly. Her toned legs and ass combined to let her walk like a strutting snake, all sinuous slides and curves meshing together in a sight that always caused whiplash in public.

Her stomach was tight, but still had that layer of fat that made it look like a female, not like a man with a six-pack. Long ago, she had decided that her bottom heaviness was not matched by her regular D's, so she got huge implants. They had to do them gradually, filling them slowly over a period of two years, to avoid stretch marks. The last two were performed in Mexico, where they didn't have the restrictions we do here in the US. It made a sumptuously broad soft set of firm, hot delights that you could get lost in. They were so big that their cleavage never stopped. Clothed or naked, her breasts pressed tightly together over her breastbone, and extended out slightly from the sides of her chest. They were topped by large areolas that had huge nipples. The fact that her tits were so large made them look normal sized, but when you concentrated on them, they were almost a full mouthful. Again, proportions. What size were her tits? At a certain point, when the bra needs to be custom made and custom finished, who the fuck cares about a number? It was the final expression of this creature of curves and lust, and if it appeared improbable; then you were right. If you thought it was wrong, then you were jealous or just pig-shitted stupid.

Her face was beautiful, too. Long dark wavy red hair long enough to cover her face and almost reaching down to her groomed paradise, that huge steam pipe god had given her. She was Swedish, and although her body didn't show it, her face did. Most people think Swede's are all blonde, but there is a large fraction who are redheads. Usually they were a pale shade of Lauren's flame kissed mane, but the genes were there. Strong cheekbones, large eyes spread wide apart, luxurious long lashes underneath large, russet eyebrows.

We were all holding our champagne bottles, watching the Dick Clark New Years Rocking Eve Show without Dick Clark, and there were a few puppet heads and Whitney Cummings going way over the line for a show that kids and old prudes were watching, and Carson had a mask that he could put on so that he could look embarrassed when everyone knew he was cracking up.

My left arm was linked with Lauren's right arm, and we were holding hands. She has a firm grip, and her perfectly shaped, short blue nails were resting gently on the back of my hand, gently stroking it.

ten, nine, eight

Her hand loosened, in that voiceless way that lovers send messages, and we let go of our hands

seven, six, five

I felt her hand slide underneath my belt and hold my ass cheek. I took my arm and pulled her beautiful slender waist close, so hard that her huge right breast flattened against my side, and her delicious ass pressed into mine. Pulling her stomach into mine actually caused her to bend a little, so large was she above and below. I looked over and saw how her soft waves cascaded over her back and fell lightly on her tits, a few hairs falling in between her breasts like scarlet threads, and loosely brushing my arm hair

four Three TWO

She slipped a thin finger right up my ass, and I jumped. I looked over at here with a warm smile, eye to eye, and leaned forward to kiss her

ONE

Lauren leaned forward and our tongues came together, and I licked her lower lip while she thrust her tongue in my mouth and pressed her finger deeper and

ZERO! The room exploded in "Happy New Years!" as Lauren shoved a second and third finger up my ass so hard that I rose onto my tiptoes, flashes of pleasure weakening my knees, and then we were going at it.

We were holding each other, kissing warm and hungry at the same time, when Jessica, the beautiful slim brunette who I'd grown to love, joined us. The three of us managed to tumble into a room, close the door, drink our champagne, drop the glasses at the end table, get naked, and fall into bed, without ever totally letting go of each other.

Jessica had a thin athlete's body, earned through hard and long gym sessions. Sometimes I led her, and sometimes she led me in our workouts. She had slender hips, a tight stomach, and a pretty set of b cups. Her small areolas had petite, rock hard nipples – she didn't wear a bra unless she wanted them pushed up for some reason, and either way, you could always tell when the headlights were on. They usually were.

She had long brown hair, with a reddish hue in the sun, and it was always coiled like a long snake in a ponytail that reached past the small of her back and nestled in her crack. If it had fallen loose, it probably would have been at her thighs. Small nose, sparkling brown eyes, an open and inviting expression, and a permanent smile. She was part Puerto Rican, part Jamaican, and part Korean. Her dark skin held a touch of the yellow, and her deep brown eyes had slight epicanthic folds. She was intriguing and beguiling, a snake twining herself up to the pipers tune.

She ended up between us, standing almost nose to nose with me, eyes closed and tongue busy. I had learned to keep my eyes open, and it made everything better. I enjoyed the faint blush that rose on her face as we made out.

Right on the other side of Jessica was that busty shemale beauty. Lauren pushed gently on Jess's back, pushing her flat on the bed. Then she turned her over on her back. I leaned back down again, and now I starting kissing her hard, pulling the lower lip tight, while I pinched and twisted her tits and nipples tightly. She liked it hard, not rough; just the right amount of force. She liked to be used but not abused. And, boy, were we going to use her.

My cock had risen along its full length, flat on my stomach, and she reached up and pulled me down so that we were in a 69 position. My dick slid effortlessly into and down her throat. She pulled it out and swallowed it again and again.

I licked her clit, large and also firm. Her juices started to flow, and I both added to them with my saliva and sopped it up with my lapping tongue. I ate her out for a few minutes, and then looked up, knowing what I was going to see.

A cock. A monster cock; a cock that could not be believed. Most of the family were completely hairless, but she had left enough hair on her balls and the base of her dick, maybe an inch, just enough so you could see the bright crimson hue.

Her cock wasn't just long, which it was. It was almost nine inches, but the proportions were so off you didn't realize how long it was. It was HUGE around. My two hands could go around it, but a woman's hands couldn't. A slightly small soda can, a larger than normal energy drink. Huge.

It was topped by a cut head so large that my hands could hold it - but just barely. It had had required long practice just to get it in my mouth. Deep throat? Impossible.

I loved it.

I kept licking and loving Jessica's pussy, and she got wetter and wetter. With one hand, Lauren stroked her monster up. She was a grower, not a shower, so when she dropped her pants she had just a delightfully swaying, huge trunk of a cock. I loved to feel it balloon in my mouth, so I grabbed it and sucked it in. While it swelled in my mouth, I kept rubbing the beautiful vagina below me.

Even Jessica's pussy was beautiful and well proportioned. Her lips were a deep brown, darker than her skin, with gentle folds covering her gloriously delicious hole. When excited, they parted slightly, showing the perfectly tight hole underneath. One finger in, two fingers in, three, she took it all – and yet was tight when each one went in. My thumb stayed firmly circling around her clit. Her muscles pulsed every time my finger hit just THAT spot, and I put more and more attention to it, driving her into a frenzy of gasps and cries of "more, more, more"...

Lauren's cock had grown so much that it was pushing against the back of my throat, so much that it hurt, so I backed off a bit. I rubbed her cock with one hand, and savored the plum sized furry balls swaying back and forth right in front of my eyes. They were so large, and her sack so big, that they each seemed to be in their own furry pouches, two low hanging fruit that begged to be sucked in.

I started to see spots, so I knew I needed breath. I went to pull her out, but her head was so large I had trouble. Finally, with a jaw cracking pop, her proud cock squirted out of my mouth and stood rail straight right in front of my eyes. The veins on the top were so large that they were like sliding rods of deep dark blue, and the line on the bottom of her dick protruded out as large as a pencil. Her impossibly large head, bigger than a baseball, was a deep dark purple, glistening with my saliva.

I rubbed and licked the pussy beneath me, and Lauren put her cockhead against her slit. She didn't put it in; she just held and pushed – a promise of what was to come.

Jessica started gasping for breath now, raggedly and desperately trying to keep enough air in her lungs, and although she kept sucking my cock, it was clear that her mind was on what we were doing to her. She moaned, she writhed, she cried out loud and whimpered when Lauren pushed just a little too hard, and the cock jerked inward, stopping before the wide flared bottom of the proud head went in, and then she trembled, and suddenly her body shook, and shot up, as much as my cock impaling her mouth would let her, and she shook as orgasm after orgasm rolled through her writhing, whimpering, gasping body. Her pussy flowed freely, covering my jaw with sweet syrup.

When she was done, I went back to her nipples and breasts, but softly now; just an "I love you" lapping with curved tongue all over, between, and gently sucking on her nipples. Lauren took her rock hard cock and rubbed it up and through her vagina lips, sliding over her wet slit and clit, back and forth, not hard, just to remind her that we weren't done.

After a few minutes of this, I leaned up and started to make out with Lauren. My chin was wet with Jessica's juices, and Lauren swallowed then from my chin with one sucking kiss. I was still leaning over Jessica's chin, with my balls on her mouth, which she obligingly pulled in and rolled around like candy. By now I was completely hairless, not a whisper. My hairless nutsack felt wonderful in her warm mouth, with her tongue occasionally snaking up and licking my asshole.

Her legs wrapped around Lauren's waist, keeping her body pressed close against her crotch and her cock laying like a thick sausage on her belly, with the head protruding past her belly button, hiding much of her lower body.

Then Lauren gently removed Jess's legs from her waist, and motioned me to go behind her. She gave me Jess's feet over her shoulders. They were rubbing Lauren's earrings underneath her thick scarlet hair. I rubbed my cock hard against Lauren's back, watching this glorious sight.

She slowly put her monster on Jess's pussy and pushed. Nothing of course, it was just starting. She leaned over, breasts rubbing breasts, huge tits hanging just slightly, perfectly, covering the beautiful small nipples and breasts completely.

Then she started to roll forward and backward, a belly dance, with just a hint of side to side. Lauren pulled her chest back with that glorious rack pointing up to the sky, and then undulated her body forward so that her cock pushed against Jess's pussy. She did this again and again, with her purple cockhead slowly easing itself in, a tiny fraction each time. Standing behind Lauren, my dick nestled tightly between her beautiful ass cheeks. My arms snaked through her hair, as she started to sweat now, and I held Jess's feet up. I pulled just a little harder, and her ass lifted slightly into the best position.

Lauren stopped moving for just the moment that I lifted Jess's ass of the bed, and then her cock head slipped in. Jess squealed, while Lauren's hiss flared loud across the room. I moaned at the view, and just watched. Lauren's cock started to push in deeper and deeper. She knew better than to pull it out again.

Lauren's cock was so large that it made her belly bulge as it sank deeper into her cunt and then back came almost out. Up and down her tight stomach rose and fell, as Lauren's dick went in and out. You could see the head moving almost as a separate creature plunging her from top to bottom. Slowly, so slowly, Lauren started to move faster.

I covered my hand and then my dick with spit, leaned forward, took my cock now pressed firmly against my stomach, aimed, and in one push sank balls deep into Lauren's beautiful asshole. She stiffened for a fraction, groaned loudly, and pushed all the way into Jess.

Jess moaned and instinctively tried to pull away, and then she pushed her hips onto that rod spearing her with a yelp of pain and pleasure. I started pumping fast, grunting with every forward thrust. No foreplay, just hard fucking.

Lauren almost instinctively met my stroke forward with a backward push. Her perfect ass cheeks flattened briefly against my hips, with her powerful muscles stopping them after her glorious softness spread like a hot soft blanket over my waist.

So fast, faster, and then sawing forward as fast as possible, my cock went into her, her pole pulled out of Jessica, and then as I pulled back Lauren punched forward into the wet stretched pussy. We slammed each other back and forth, groaning, moaning, crying with abject pleasure. Jessica was crying now, her body out of control, tears leaking from her exotic eyes down the sides of her writhing face. Then suddenly we lost our rhythm, leaving us all pushing and straining almost randomly, and then Jess's feet shook, shivering back down to her body like a sound wave. She screamed, a long drawn out wail that cracked plaster and rang glass, and then started bucking up and down, shoulders slamming down the bed so hard that the huge headboard was smashing hard against the wall behind her, crack crack crack!

Lauren gave a mighty push, so much that I lost hold of Jess's feet, pushing her forward on the bed, and growled wildly as load after load gushed into Jess's asshole. Her cock left no room left in Jess's pussy, so Lauren's cum squirted out of her hole all around the huge hose, spurt, spurt, another spurt of thick creamy white. I couldn't see it from my position, with my cock plowing her ass, but I knew that her stomach was covered in her huge load. Lauren knew better than to pull right out – Jess couldn't take that much abuse. So she just stopped moving, letting herself slowly go soft so she could come out without too much pain. Jessica just lay, sweat streaming off her chest, pooling and spilling out of her perfect belly button, rolling around her sapphire belly stud, soaking her ponytail and covering the soft blanket with dark spreading stains. Streaks of tears lined her face, over a satisfied cat's smile.

When Lauren's cock had shrunk to just a mighty size, she slowly pulled herself out. Jessica's pussy was gaping open, and then with her amazing elasticity, slowly closed back to her normal tightness, her clit shrunk, and then her vagina looked just like it normally did, a beautifully tight and inviting slit. The only sign that she had been impaled by a baseball bat only a few minutes ago was the beautiful bright scarlet of her abused lips, and Lauren's cum dripping off of her bald crotch and down between her legs to the even more abused blanket.

I leaned forward, pushing my cock all the way into Lauren's asshole, and she twisted her head around to kiss me hungrily. She was too tall for me to get in her completely standing up, so she kept the kiss, until she lay down on the bed, careful not to let me go. She closed her eyes, took her legs with her strong feminine hands and lifted them up. Her tits were so large that they pushed her sturdy legs away from her body, and only her arms holding them up kept them out of the way.

I stopped, briefly, to savor the sight. My cock was buried in her asshole. Her hose lay on her stomach, still leaking cum in soft pulses into her sweaty stomach, so feminine, so shapely. Her huge breasts with its monster cleavage were pushed together with her arms, her large nipples surrounded by the perfect circular areolas sticking into the sky, her neck straining, tendons sharp, her stunning face surrounded by matted hair, scarlet on pastel blue sheets, a rose against the sky.

Jessica lay near her, heads almost touching, still shivering, eyes closed, whimpering in afterglow.

Then I pushed so hard I groaned with the effort. My cockhead, always curved sharply up, pushed directly onto Lauren's prostate, and she jumped. Her cock shivered and started to rise from its flaccid state. I pushed again, and again, and every time her cock swelled a little more, and her balls were on my dick, and I held them, one in each hand. I squeezed them harder with every thrust, just to the point of pain. Her tits were bouncing up and down her body and she was moaning and shouting "more, more, give me more!" I took let go of her balls with one final firm grasp, and started rubbing her cock furiously with both hands. I kept pounding so much, so hard, that I slipped and stutter-pumped her once, then with even more strength. Her tits were bouncing back and forth, her cock jumped harder and larger in my hands, and she whined higher and higher every time I pounded her insides, again, again, again. She was running out of breath, panting, mouth open.

I went faster and faster, harder and harder, until Jess slowly got up and started kissing her open mouth, tongue darting all over Lauren's dry mouth, sweetening it with her wonderful lips and saliva; then her nipples, forehead, all over. I pulled and loved and stroked her cock, one hand pumping furiously on the shaft and one on the mighty head, rubbing hard and fast. Lauren shocked into a completely straight position, and then blew another huge load straight up, hitting my chest and face, shot after shot of thick hard delicious cum. That tipped me over the edge, and I exploded myself, blasting right into her ass, hard, spunk after spurt of hot white juice. I sank down onto her, and my dick stayed in her asshole. I was pillowed in her breasts, with Jessica softly stroking my back. Just laying in and on one woman's sumptuous breasts, with her dick wedged between us, large enough to push into me, soft enough so I could feel it throb, and then being stroked all over, kept me hard for a long, long time. As we idly cleaned each other with lazy lips and rolling tongues my cock slipped out of her ass. I remember my tongue lingering in the small of Lauren's back, and I know I went from licking to kissing to resting gently, but eventually, unnoticed, we all fell asleep.

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