A Younger Emily

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Emily's first time with another achieves her first orgasm.
2.8k words
3.48
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Part 2 of the 2 part series

Updated 06/14/2023
Created 03/20/2023
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Jono sat on the bus looking out the window as the rain pelted the side. He was on his way to pick up Emily, his girlfriend, well ex girlfriend, from the airport. It was a mutual breakup, though he had no real choice in the matter but she only did it because she was heading overseas and he couldn't justify following her. He'd pondered over why she decided it was best to break up before she left as opposed to when she left.

At the time they were both half way through their Degree when she'd decided it wasn't for her, found a summer holiday camp job half way around the world and booked it in. Breaking up to spend her last few months catching up with friends and family before she was off, potentially forever.

They'd been neighbours in their first year and as they got to know each other over the trimester, Emily made a move on him. Jono wasn't a virgin, but by no means experienced in sex, the only other time was in the back seat of his car after a party. Emily had been a virgin though, and Jono made sure she was comfortable that first magical time. She only complained when he attempted to go a third time the next morning and she had said it was a bit sore, obliging, they'd just cuddled. Getting to fondle her pert breasts was also a fresh, wonderful, experience. Spending hours exploring the rest of her fit body.

Emily had just been to see her sister who was studying medicine up North. Flying up for a week and then back into town for a couple of days with Jono and friends before flying out for the camp. Jono slipped his earbuds back into their case as the bus pulled up. He hopped out and made his way to the Arrivals. Stomach a wreck. Nervous because this was the last few hours he'd get to see her, his love, while also excited because he'd be getting to spend some time with her after a month or so without.

Jono was awestruck when he finally laid eyes on her. Still as he remembered, her gorgeous smile and naturally beautiful face, no makeup required. All five foot six of her was perfect. He hoped he was still allowed to hug, kiss and so much more over the next couple of days. Previous highlights of their past were fresh in his mind. The only thing he felt they'd missed was confirming Emily had ever truly orgasmed. There was the weekend they'd had away when she had said afterwards she'd wanted to scream when he was going down on her. Then the massage on her bed, he had spent a good forty minutes giving her a full body massage, ever so carefully rubbing close and grazing her labia until he could see she was soaked. Managing to undress mid massage without her noticing, positioning himself over her and ploughing deep from behind. She had made some noises that time.

Emily was drinking out of her bottle when she spotted him, eyes smiling, she had walked over and given him a proper lovers hug like nothing had changed. Jono was only able to reciprocate, he'd take everything he could get. Before long Emily was striding along beside him chatting away just like old times. Jono could never understand how she was able to do this, nothing seemed to affect her, while his mind was counting down the minutes until she was gone again. He had reached out for her hand taking hold of it and it helped with the gut wrenching ache.

Back at his flat Jono showed Emily to his room and grabbed a couple of beers from the fridge. They sat down on the end of his bed and Emily had begun to untie her shoes. Jono asked how her sister was. Emily was half way through the second shoe and paused a moment before continuing and dropping it to the floor. She sat up cross legged on the bed and without any preamble said "I slept with my sister's flatmate."

Jono glazed over. The reality he knew evaporated. His head flooded with images, imaginings of what she'd done. The imagination turned to questions and he felt her eyes burn holes into the side of his head. She was needing a reaction, Jono realised, he could lose all of her right then if he acted poorly. Remembering she was no longer 'his' he had no right to be pissed, but fuck that was a lot.

Jono turned slowly towards her and pulled his legs up as well. Arms folded he was struggling, searching for some kind of control. He looked longingly at her only to find tears flooding down her face. He reached out and pulled her into a hug. They both fell down on the bed sobbing into each other.

Once the brunt of it had passed Jono noticed his pants were tight, his body had gotten so used to Emily there was no stopping this urge. Emily noticed too. She looked up and made eyes. Smiling that perfect smile, she reached down and ran her hand over the top of his pants. Finding the outline of his erection. Both of them relaxed as their bodies fell back on old habits, exhausted.

Jono couldn't tear his mind away from some of the questions in his head though and before he could stop it blurted out "Did he make you cum." Emily paused, obviously thinking about it. After a few moments replying "Yes." Jono was yelling at himself for asking such a stupid immature question when her answer slapped him across the face. "How did you two hook up?" Jono gushed, the damage done. Emily went into a detailed description of the flat and how she'd been given the couch to sleep on, then that night they were all watching a movie and she'd sat next to him, Shaun. Nothing had happened but she'd felt something, horny maybe, she'd not been laid for ages. "Anyway after the movie Shaun asked if I'd like a bed instead of the couch" Emily continued. "He was decent looking, I hadn't had sex in months, I've never had anyone but you. I thought, why not."

Jono just stared, she'd been so easy, the woman he loved completely, had fucked the first dude that had asked her. "How big was his dick" he asked, feeling flustered. Butterflies were invading his insides. "Big" Emily responded. "Really big." Jono clutched his chest. "It fucking hurt" she went on "He wasn't gentle like you and didn't go down on me like you would have either, it was all a bit different"

Jono rolled away onto his back, the feelings he had were all a bit much. The room silenced as they both fell into thought. Emily had rolled with Jono and kept her hand on his hip. Now on his back his erection made a large tent. She moved her hand to it and found the zip for his fly, pulling it down, she reached it and removed his penis from his underwear. All five inches visibly throbbed, his foreskin already rolled back due to how hard it was. She sat up and lowered her mouth onto it and gently sucked on his head, extending her tongue along its underside. Jono jerked and came into Emily's mouth. She swallowed like every other time she'd done this, not missing a drop. Soft lips encased the head of his penis and her tongue swirled around. She stayed like this until he was done, sucking it clean before she fell back onto the bed next to him.

Post nut clarity descended upon Jono and his thoughts fell into some kind of order. The one at the front being, how big. This was the question that burned inside. Maybe it was due to all the porn he had been watching recently. He rolled his head to look at her and asked "So how big is really big?" Emily went red "I don't know, it's not like a got a tape measure out to measure the fucking thing." "Well describe it to me then." he pushed. Emily hesitated before she reached down to grab his hand. She pulled it up in front of them both and squeezed her fingers around his wrist, middle finger and thumb just barely touching together. Jono's eyes went wide, as thick as his wrist, wholly shit. Then sliding her fingers up towards his elbow she stopped about halfway. "There." she said. "That's how thick it was." "Bullshit." he replied.

Jono got up and grabbed one of the beer cans he had gotten earlier. He did the same as she'd done with his fingers around the can then handed it to her. Emily repeated it on the can. "Yea." she said "About the size of a can then. Well not one can." She then reached for the other one and sat it on top of the first can. "That's about it. Really soft though, like even when he was erect it was kinda squishy, not like yours which gets super hard." She placed them one on top of the other down on his table and they looked. Jono couldn't believe it. His mind refusing to accept that his love could fuck other people so nonchalantly, let alone a dick the size of his forearm. Should he have felt turned on, he couldn't tell, but he did. Part of him was wishing he'd seen it happening.

He reached out and stroked her shoulder, caressed her neck and then slid his hand down her back to her bra, undoing the clasps in a single quick motion through her t-shirt. Her breasts surged forwards and he reached down to the bottom of her t-shirt and lifted the whole lot up and over her head releasing them. Jono pushed her back down on the bed and her breasts jiggled, nipples firming up with the change in temperature. Moving down to her jeans, popping the buttons and pulling. They were well fitted to her slim legs and took a few good tugs to relieve her of them. He left the knickers and dropped the jeans to the floor. Then admired her and made a mental note of her almost nude form, locking it away for later.

Jono shuffled over her and began planting kisses everywhere. Licking delicious areas of her skin, like the inside of her thigh or the crease where breast meets ribcage. He ran his fingers all over, feeling out her form, definition, a short squeeze of her bicep then gripping a heel and ankle. He avoided all the sensitive areas for now. When they made eye contact he asked "So why did it hurt?" As he continued to toy with her body, the occasional brush of a nipple, hands getting further up the thigh.

"There wasn't much foreplay, we pretty much stripped off and went at it, him on top. I didn't expect him to be so large, it was pretty dark so didn't realise just how big until he was trying to stick it in me."

Jono had moved to the edge of her knickers and had been carefully slipping a finger under the elastic, he could see a small wet patch so knew things were progressing nicely. "So what did you do?" he asked. Emily let a whimper escape when Jono had nudged her labia. "Well I was so fucking horny. We'd been making out and he'd been playing with my boobs, I told him to stop as it hurt. I used my hand to hold him and rub the head of his dick around without actually pushing it in" She went on describing how after a while she'd got so wet there was a spot under her on the sheet.

She'd felt ready so still gripping him, lined it up and let him ease it inside of her. "Then what." Jono urged. "He was kneeling, I'm on my back and I had my elbows wrapped around the inside of my knees so I could watch everything. The worst bit was getting the head in, after that the pain subsided. It still really hurt, my eyes were watering, but it felt kinda good at the same time, like really full. It was pretty amazing watching something so massive sink into me. He came pretty soon after that. To be honest, I'm still a bit sore down there" Emily explained "He came inside you?" Jono queried. "Yea I'm still on the pill, remember." Emily answered. Jono didn't have the heart to tell her why condoms were a thing right then and wasn't about to bring the mood down by trying to find one of his.

Her panties had a large oval wet patch and he had become pretty solid after listening to her story. Once he'd dropped his clothes on the floor and lay down beside her naked his final question was ready "So what made you orgasm then?" "Oh" she said. "That didn't happen until the next morning" "You guys fucked more than once!?." Jono choked. Emily went red. "Umm, more than once, we kinda went at it like rabbits after that. I was there for what, 6 days. Anyway I woke up to light coming in through gaps in the curtain, he was still asleep, spread out on the bed. So I kinda gave him head while he was asleep, you know, morning wood." Emily continued to describe how she was fascinated by his penis and how big it was, so having some time to explore it before he woke up was fun. Pushing her tounge in under the foreskin and running it around the inside. Sucking on his balls and clasping his girth with both hands, measuring it.

Jono was past caring "Fuck me the same way you fucked him. Show me how you orgasmed." he jested. Emily giggled "Ok then.'' She'd sat up, flicking her knickers off and pushing him onto his back. She kneeled between his legs as described in her story and sucked his dick to full attention, bobbing up and down. She then squatted over him, her feet roughly inline with his bellybutton, a hand placed on his chest and the other reached down to his cock lining it up. Her bum dangling out over his rigid pole. Jono glanced over at the two beer cans and thought about the size difference. A dick like that would already be inside her, stretching her out, an inch deep.

She started to detail how it happend "So I got over him like this" Her bum still dangling precariously and putting both hands downs on Jonos chest "and then squatted down on him, it felt so fucking good. I think he was awake by then, but he just lay there. I slid up and down really slowly for aaaages and eventually got all of it inside me, like this." She motioned. Dropping her arse down into Jono's lap and taking all of him in one go. She'd slowly come back up so just his head was inside and then dropped it back down bouncing, again and again.

Emily was looking down between them, watching how her pussy swallowed his penis. Jono relaxed back imagining her doing this on someone else's cock, moaning hard, screaming for more. "And then you just came" he asked "Yea, after a few times with it going all the way in, I got these really deep wonderful feelings, my whole body was pulsing, flooding, I started to shake and I think I was moaning, oh it was so epic." she gushed.

Jono concentrated on not coming, noticing she wasn't coming on his dick and asked "Did he cum?" "No, once I finished, he rolled me over and put my ankles up over his shoulders. Here like this." She rolled off, legs in the air and Jono climbed on burying his dick. "Mmmm" she moaned "Like that". She squirmed under him and made sure he was as deep as possible. "Then he put his hands here and here." she motioned to her armpits. Jono found the position she was after. "Then he lifted his butt up and I could feel his dick slide almost out, then he would slowly push it back in, all the way down, he did this for a while and sucked on my tits. Slowly getting faster, I could feel his balls slapping my arse." Emily was in full story mode. Detailing the entire event thrust by thrust. Shaun's thrusts had grown in strength until Emily's firm arse rippled with the force, she had her hands pushed against the headboard and was screaming as he'd taken ownership. In and out relentlessly, a second orgasm washed over her. Her vagina contracted with what little resistance it had left. He'd come and emptied inside her a second time.

Jono pounded away himself and wondered why they'd never tried this position, it was great. He noticed she didn't feel the same, the thought of that pornstar sized dick being pumped into her again threw him over the edge and he let go inside her, body satisfied, soul destroyed.

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