Emma - The Early Days Pt. 02

It's been over a decade since Emma and I had been together - footloose and fancy free as twenty-somethings, her journeys from interstate seemed to end up in the most wild sexual encounters. But it didn't start out that way... Your comments and feedback inspired me to share our next encounter, and this is literally just the beginning. Like what you're reading? Check out "Emma - The Early Days"

++++

Saturday morning, I woke with a raging hard-on and a solid hangover headache. I could almost guarantee I'd be horny the morning after a big night on the drink.

Annabel must have wondered what had got into me - she stirred and woke, with my cock very deliberately pressing right into the crack of her butt - just the cotton of my boxers and her knickers between us. Will was fast asleep, Annabel was silent and as much as I thought she wouldn't play, I was persistent and never one to miss a chance that she might finally let her guard down - as she reached back I expected a familiar adjustment and whisper to decline - instead, she curiously slid her hand over my cock and gave me a gentle, silent brush through my CK boxers.

A hint of daylight streamed into the hotel room at the edge of the curtains. After months of trying to get inside Annabel's cute little knickers - it was her that had her hand, at least on my underwear. As she lightly, timidly teased my cock through my boxers she didn't even look back, sliding her left hand over my cock, wrapped in the thin cotton. I reached around to hug her - I cupped her left breast through her singlet. She let me tease her nipple through the cotton, but her right hand made sure any attempt to move down over her torso wasn't in the cards.

Not a word was whispered, it was almost as though if she didn't look back she wouldn't have broken her own rules on what base we were at. Annabel slid, slipped and teased me softly, her hand was inexperienced, but I loved it, almost awkwardly her hand wrapped my cock through the cotton and she started to gently pull me off, her hands as hesitant as her mind. I could tell she wasnt comfortable with a even the rustle of our bed sheet, she definitely didn't want Will to wake and see what was she was up to, it was strange she had chosen this moment, when we weren't even alone.

Her grip was still soft, but her motion fastened, my mind should have only been focused on sliding my fingers inside Annabel's elusive, but off limits pussy - it wasn't though, as her inexperienced hand fondled and pulled me off, all I could think of was Emma. Only hours earlier she'd gifted me her tight pussy in the hotel hallway, I'd taken everything on offer, gave her everything I had to give, leaving her with a deep passionate kiss and full of my cum for her taxi ride home. As Annabel continued to grip and rub my cock, my breathing intensified and I jolted forward as I came to climax - thinking exclusively of Emma.

Annabel had tried to 'shhhh' me to no avail, she'd maintained her innocence though, I hadn't even touched her bare nipples let alone her pussy - nonetheless, she got me off, and I had a full load in my CK boxers to deal with as she slid away from me seemingly frustrated she had given in. I tried to feel her up through her knickers, but her shoulder nudged my arm in decline, the best I could manage was brushing across the top of cotton covered mons. As I tidied myself up, I wondered if Annabel was a virgin, we hadn't talked about it, in the back of my mind I was beginning to think she was waiting for "the one" when it came to getting inside her underwear.

Saturday in Portland was upon us and given the hangovers, headaches and sleep-in it was fairly uneventful. Annabel showered and decided to head over to see her parents, Will and I desperately needed some greasy food for the hangover - eggs, bacon and coffee was the order of the day. Annabel text the girls, the plan was to meet at the hotel for a drink at 7pm then head to dinner. Will and I chatted about the night before, we didn't have any secrets and I wasn't about to hold back on Emma - he loved every detail. He was not the jealous type at all, in fact it was usually him landing the bulk of action with me all ears - but he was pretty blown away that Emma had let me fill her bare back, "that's pretty wild Dave, fuckin hot, it's gonna be damn fun to watch you handle this situation" he joked.

I knew I had to text Emma, but I have to admit, i wasn't sure what to write and I kept procrastinating. I decided to play it straight and shot off a quick text to Emma:

Dave: "I hope the cab home was ok and you got some rest - Annabel said you guys up for another big one tonight?"

Emma's reply was almost instant, clearly she was waiting for me to clear the air - smart girl, she probably knew that Annabel might've seen my phone.

Emma: "I've been waiting for you xx, I'm still in bed, hungover and feeling very guilty about last night"

Dave: "Hey, I know - it's been hanging with me all morning, but Jesus, Emma - that was next level"

Emma: "Ummmm yes, I don't know what to say..."

Dave: "You don't have to say anything, but you do have to make sure you come tonight."

Emma: "I guess so... x"

Dave: "7pm, you got this Emma x"

Will and I headed back to the hotel and had a lay-down, he was channel hopping on the TV and I was dozing half asleep - about a half hour, my phone lit up.

Annabel: "Hey you... The girls are on for dinner, not sure they're up for a another big one though!!"

Dave: "Totally understand, maybe I can return your morning favour to you later on"

Annabel: "Dave! See you around 5pm"

Ding... It was Emma - her message literally came over the top of Annabel's reply on my phone screen.

Emma: "I've got a plan..."

Dave: "I'm not even going to ask, but you are so fuckin naughty!"

Managing to achieve absolutely nothing else but lay in bed the rest of the afternoon watching the ball game, it was just after 5pm when Annabel got back to the hotel. Will went out for a bit to give us some space and I let Annabel know how much I enjoyed our little soiree this morning - after all, it was the first time we had 1:1 to talk. "You were literally hard all night horn boy, anytime I moved I had your dick in my back" she laughed... I was feeling the guilt, Annabel and I were joking around like teenagers, we kissed and played but this little cutey may as well have had a padlock on her panties. As we started to get ready, my mind turned to Emma... I knew I had to be discreet, I knew there were no guarantees, but the opportunity to hook up with her again was more than just an itch that needed to be scratched.

Annabel had slipped into a nice little black skirt and matching top. She dressed miles hotter than her bedroom playbook. Will and I, our standard jeans and shirt combos - with him joking how much better his shirt was than mine...we headed down for a few drinks in the lobby bar. Annabel's friend Claire had already arrived - she normally dressed so conservatively, but Will had his eyes all over her in a hugging black dress. I was a bit on edge, wondering where Emma was, how she would react - but like clockwork, she made her way from the opposite end of the lobby in heels and a slinky little charcoal dress, the bottom a touch above her knees, a low cut showing off her cleavage.

We joked how we'd all woken Annabel the night before and how bad our hangovers were - Annabel claimed she was the smart one for having finished the night earlier than everyone else. Claire said her parents were a pain in the ass and woke her early and that's it's time she moved out, Emma said she'd been in bed all day... Will, never one to hold back, quipped that he would have liked to have someone as hot as Emma, Claire or Annabel in his bed all day, Emma's eyes momentarily connected with mine.

As Emma and Claire chatted, I heard Claire announce "That's a great idea". "What's that?" said Annabel, "Emma suggested we see if they have any rooms available so at least we can get a sleep in tomorrow, and besides I spent $40 to sit in a really bad cab last night" Claire replied. A few minutes later Emma was back, waving the little keycard for the room... "Never underestimate the power of a sexy little dress girls - A wink, a smile and $150 later the guy at the front desk got us a room - and with his staff discount no less!". Emma sat down on the bar stool, her dress slid up mid thigh, I wasn't even close to discreet as my eyes zoomed on her legs and a tiny glimpse of what looked to be dark blue or black knickers as she rotated the seat into the bar.

We headed from the bar to a hip Spanish place nearby about 9pm. With Annabel on my left and Emma on my right, I was on my best behaviour, hands above the table at all times, plenty of fun chat but it was the occasional innocent contact with Emma's leg that had me on edge. Will had a renewed interest in Claire, she was laughing out loud to whatever story he was telling - those two had a little bit of chemistry on display. We ate, drank, chatted and laughed, it was close to midnight as Will sorted the cheque and we headed to the club.

There's something about the darkness and disorientation of a club - the lights, music, smoke. I think Emma knew that she could be much less conservative on the dance floor - even strangers were bumping into each other as was we all danced. I'd made sure my hands got their share of "accidental" contact with Emma - front and back, that slinky charcoal dress was smooth and tight, especially on her ass. I got a tray of shots - cowboys and tequila, after the lemon, we licked the salt of each other's hands, Annabel of mine, me of Emma's and so on... By this stage Claire was kissing Will passing him the lemon wedge directly from her lips to his - I gave Annabel and Emma a high five, my left arm around Annabel and right around Emma, a group hug and dance as our friends made out.

The drinks flowed and it wasn't long until we were all well and truly alcohol infused. Annabel always tried to pace herself, being little more petite than the others. She joked that Claire and Will, who were now all over each other, should get a room, Claire joked back "we've already got one Annabel, that was Emma's job!" poking her tongue out. Annabel asked me if I was ready to go back to the hotel, I said I was keen to stay but was happy to go with her, or at least walk her back. Emma was keen to stay and had attracted the attention of two guys which had me eager to get back - but it was all quite timely as Annabel and I made the short walk from the club back to the hotel. She was super tired and a touch drunk. She let me play and touch her tits and nipples as we kissed but nothing more than a quick rub of her pussy over her black cotton knickers before she announced she was tired and going to sleep.

I was wide awake, horny as can be as I headed back across the street to the club. I wasn't surprised to see Claire and Will on their way out, I was however a little surprised that Emma told them she was staying on and that they'd left her with two guys. I hoped Will took Claire home and those two had a good session, otherwise it would've been a lean weekend away for him. Back inside and on the dance floor I saw Emma - right in the middle of the dance floor, and two guys dancing with her - she had them ogling over her, they were up close and had their hands on her ass and hips. I made my way over, sliding in from behind and grabbing Emma's hips. She flinched thinking one of her dancing pals was going too far. After realizing who it was, she arched her ass back into me wiggling against me, causing the blood to flow instantly to my cock. The two newcomers didn't know what to make of it, they'd clearly been trying their best to get close to Emma and out of nowhere I'd arrived, kissing her neck and and tracing my hands over her slinky fitted dress chest to hips, hips to ass.

We kissed in the club, and as Emma's tongue returned to my mouth, my mind returned directly to everything we had shared less than 24 hours earlier. Emma rubbed herself against my thigh, even though her dress was in place, I could feel the heat radiating from her pussy against my thigh as I flexed my quad. I knew I had to have her, and the feeling was mutual. More dancing, more touching, more kissing - my fingers even rubbed Emma over her panties where the darkness and smoke gave me cover to do so. By the time we decided to leave the club, my cock was literally stretching the denim, I had to adjust myself as walked over to the hotel.

"With what I have planned for you, we certainly can't go to your room big boy" said Emma as the elevator headed up to the 11th floor, "Let me see if anyone's home at my end, maybe Claire is getting her fix from Will" she said "Otherwise, there's gonna be some Deja Vu" she joked, pointing to the exact spot in the corridor from our earlier encounter. I kept my distance from the door, and used the chance to check my phone. Will had text to let me know that Annabel was fast asleep and that he and Claire were in in the other room as Emma had Claire's key. A stroke of luck for now, but wouldn't Annabel be wondering where the fuck I had got to? I hoped Claire and Will didn't wake her. I walked toward the room door and as Emma said "all clear Dave" I showed her Will's text. Emma checked her phone, a missed call from Claire and a text asking her for the key. This woman was a quick thinker, she looked at her watch, it was 2.30am... she sent off a text to Claire "Hi sexy, I'm still at the club dancing with all the boys, see you at the room at 3am". We had found ourselves half and hour.

It was usually me making the move, but it was different with Emma - even before the room door had closed she pushed me against the entry wall. Her kiss was unrivaled, by anyone in my life - it was like her tongue was a magic wand. She unhooked my belt and unbuttoned my jeans as I pulled her dress up from behind, exposing her ass cheeks, parted with a black sheer thong. I massaged and gripped her ass, teasing and spreading her cheeks. Emma dropped and crouched in front of me, her dress was sitting above the waistband of her panties - her legs were spread wide and I could see the curve of her pussy, wrapped in the crotch of her black sheer thong. It was so fucking sexy.

With her kissing prowess, I stupidly hadn't even joined the dots on how just how good Emma would be at sucking cock. As Emma freed my fully erect cock from my boxers, I needed have bothered to think, I was feeling her lips and tongue weaving on my 6" shaft here and now. She sucked like a pro, her head bouncing and tongue tracing my shaft, I didn't need to guide her, Emma took me deep then lathered me with her saliva - licking the underside from my balls to the tip, before gripping my wet shining shaft with her hand and pumping, only to return her mouth taking all of me in. As Emma leant in expertly blowing me, I unzipped the back of her dress and unclipped her strapless bra fell to the floor and my hands cupped her firm c cup tits and rubbed and pinched her bullet hard nipples. There's something about silence that let's you hear everything - the splash and slurp of her mouth on cock, the rush of air through her nose as she exhaled - everything was audible - then a loud muffled groan as I pinched both her nipples firmly.

With her lips on my cock, I couldn't reach any further down Emma's body but I needed desperately to taste her tightness. Her slinky dress was now just a ring of arousing material around her waist, her tits so firm they defied gravity and her pussy, so swollen, enveloped for my pleasure in her shining sheer black thong. I guided Emma's head up, as we stepped toward the end of the bed. My jeans sat around my knees, I kicked off my shoes and socks and stepped out of my jeans and boxers. Emma slid her dress to the floor, leaving only her panties on. I lifted Emma back onto the bed in missionary, we rolled over onto my back, then Emma spun around as she crawled on top of me - her lips found my cock again, and her pussy, clinging to the sheerest of nylon, sat so close to my face I could feel her heat and smell all of her.

Her thong easily slipped to the side under my guidance of my left hand. Emma's pussy was different and I fucking loved it - she had thick protruding lips exacerbated by how hot and swollen she was, it wasn't your angel porn pussy. Her clit was the size of a baby blueberry - there's no doubt her thick lips made her more sensitive and I'd never tasted anything quite like her either. She was bare as an earlobe from her bellybutton to her asshole - the feeling across my whole body as my mouth and tongue covered the entirety of Emma's lips and clit just about saw me cum in her mouth on the spot. I loved tasting her, I love how she'd danced herself wet all night, and no doubt a few strangers touches and hands in the club. What came from her lips as my tongue parted her opening was as perfect as how hot and wet she tasted already from our big night out.

My tongue circled Emma's clit, I could feel the vibration of her vocal chords on my cock as she moaned deeply. I was alternating between darting and flicking my saliva covered tongue on her clit and suckling ever so softly with my lips - this rhythm had Emma grinding her whole pussy down onto my face in pleasure. I hadn't yet gone near her arse but with her whole pussy shining with arousal and my index finger crooked inside her pussy pressing her G spot, I pressed at her perfect little arse with my wet little finger teasing and wiggling the tip into what I suspected was her virgin asshole. Her lips left my cock and she squealed "Fuck fuck fuck Dave" followed by a scream of pleasure - I took this only as an invitation, I sucked harder on her clit, as if I was freeing her tiny berry from the bunch, her pussy was free flowing wetness into my fingers, hand and mouth.

I'd gently worked my little finger about an inch into Emma's ass easing and teasing, as slow as I could possibly manage. "Oh fuck, Dave, yes yes oh yes" Emma groaned, I could feel her clit pulsing on my lips and as she reached orgasm, her hips jerked, thrusting down onto my face, the walls of her pussy gripped and released my fingers and her asshole contracted and spasmed so tightly, literally popping my little finger out - only for me to immediately press back in and deeper. Emma was levitating in her climax, in her ecstasy she had pressed the heals of her hands down so hard on my legs, she probably bruised me.

My cock was pointing directly upright below her chin. Emma had quite rightly lost focus on me as she found her high. My face was glistening with her orgasm, expecting her to be beyond sensitive post climax, I very gently released my fingers from her pussy and ass - my lips still wrapped around her perfect clit - I gave her pussy a friendly kiss. Emma sat up and atop me, she was still facing the foot of the bed - her bare wet pussy rubbed on my chest as she straddled me - slowly, she took herself toward my cock. As she sat up, her legs spread across my waist, she proceeded to raise herself up and down, Emma had positioned her pussy and clit to have the topside of my shaft gliding on her clit - she repeated this, sliding further and further forward forcing the angle of my cock to create more pressure on her clit. I wish I had a mirror on the wall in front, but what I couldn't see in front, I made up for from behind, each time Emma raised her body I could see her perfect, red opening and swollen lips, shining. I used my hands on each of her ass cheeks to peel her open from behind. Even though it had only been my little finger inside her ass, her tiny asshole contracted and relaxed with each glide of my cock on her hard clit, I could see the pink of where she'd let me tease my finger inside.

We were long on pleasure, but short on time, Emma was expert - she knew exactly what she was doing. As my thumb teased at her ass, Emma sat up a little higher, only this time the angle saw my cock slip back toward my stomach freed from the friction and pressure of her clit. Emma reached back, her fingers clasped and hand gripped my 6" shining and throbbing cock aiming directly at her wanting slit. As the tip of my cock made contact, her unique and perfect pussy took over - she was so aroused with a touch on her lips that she gasped even before lowering to part her thick wet tight opening. I could barely control myself, I wanted to grab her hips and slam her down onto my cock, instead Emma teased her way down onto me. Every single sense in my body was in overdrive as I watched her perfect pussy open and consume all of my bare cock. What was probably 30 seconds felt like 30 minutes of the highest pleasure.