Jack continues his escapes with someone new.
These stories are based on Jack’s experiences with finding Lily drunk, but before the serum. If you haven’t read those, then I would recommend reading the Drunk Stepdaughter series.
Jack stood in the reception area and tried to force a smile to hide his annoyance. He had to dig deep to manipulate his face into a smile and not give anything away. The room bustled with guests and staff preparing for the upcoming wedding, and Jack should have been full of excitement and joy; however, the receptionist had just delivered a devastating blow to his evening plans. Instead of having two separate rooms as he had booked, the hotel had made a mistake, and the only room available was a family room.
Normally this wouldn’t be a problem; however, Jack had been scheming again. He wanted to make sure Lily was in her own room so that when the drinks Jack would ply her with took effect, he could take full advantage, just like he had done a few times in the past. However, now, with Katie in the room, that was going to be a lot harder. Lily definitely got her blackout tendencies from her mother, but the risk would be too high to attempt doing all the things Jack had been dreaming about.
All this was passing through Jack’s head as he pushed it aside and pretended that the mix-up wasn’t an issue—it was only for two nights, after all. Katie reassured him that it would be fine and that Lily would be no trouble. He was sure she thought he was just annoyed that they wouldn’t be able to have sex, but she didn’t know the half of it.
They went up to the room and found it to be extremely spacious and very comfortable. Jack continued to fight the feeling of disappointment as he reassured Katie that all was fine and that they would be very happy in the room. Besides, they’d be at the wedding and barely spending any time in there!
The day of arrival was the day before the wedding. Jack and Katie spent time mingling and making merry with friends, family, and the bride and groom. It was a pleasure to be around everyone in the same space, as it happened so rarely. The venue was a stately home turned into a hotel and wedding venue. The grounds were extensive and beautifully manicured, and the bars, lounges, and entertainment spaces were grand but still felt homely. Jack spent his time drinking and enjoying the company of people he hadn’t seen in years. Throughout the day, people arrived in droves, and it wasn’t until mid-afternoon that Jack saw her.
In all of the planning, packing, shopping, and daydreaming about what Jack was going to do to Lily, he had completely forgotten that Lily’s cousin would be attending the wedding with her aunt. Ella was fifteen and had caused quite a stir in the last year with the family due to her drinking, partying, and having been caught having sex with her boyfriend just before her fifteenth birthday. She was, as Katie called her, a little slag. This had made them both laugh; it was only meant as a joke, but there was an element of truth to it. Ella was five-foot-three and had dark brown hair. Her eyes were a shade of green that gave off a constant impression of mischief that didn’t help her current reputation. She had an incredible ass with hips that swayed in a way that made you stop and stare. Her breasts were, for a young girl, very large. Jack guessed at around D cups, but that may have been because of her short stature. When she arrived, Jack was gobsmacked and had to be careful not to stare too much. It was hard not to, but the result of her arrival was that a new thought had started to form in his mind. If he couldn’t have Lily, then maybe he could have Ella.
Jack and Katie spoke to Ella and her mother, Claire, after they had done the rounds of saying hello to the family. Jack had kept the small talk flowing, but all the while was watching Ella like a hawk. Her mother had told them that Ella was convinced she would be drinking and that she had told her countless times that she wouldn’t be allowed. At this point, Katie stepped in and unwittingly set Jack up with the possibility of an opportunity. Katie told Claire that Lily would be drinking, as they’d agreed she would be able to partake in the celebrations as long as she was sensible and wasn’t too obvious with it around the staff. Claire seemed to relax at the mention of this and conceded that Ella could have a drink, as it would be unfair to leave her out if Lily was. It was then that Jack came up with a fantastic idea. He casually mentioned that the girls could keep the drinks that he and Katie had bought in Ella’s room so they didn’t get caught. Claire seemed happy with that arrangement, but Jack quickly stepped in and put across the need for the adults to also have a key to make sure they were being sensible. Jack offered to hold it, as he always kept their one in his wallet, and to his surprise, both women went for the idea!
This then left Jack with the ideal opportunity to make things interesting. The drinks they had bought for Lily wouldn’t supply both of them, so Jack offered to go and get some more. This was taken up as a kind offer, and off he went. Jack bought a small bottle of vodka and some mixers. He also got some Buzz Balls, as he had heard the girls talking about them excitedly before he went. Once he was back, he took them up to the room and dropped them off. Both girls were getting ready for dinner, and Jack reminded them to wait until they’d eaten so they didn’t make a scene. From there, it was a waiting game.
Dinner was held in a large hall which would then turn into a light social with a band in the evening. The bride and groom certainly knew how to keep people entertained, and the whole place had an incredible atmosphere. The food was incredible, and Jack forced himself to enjoy it as much as possible. He’d been keeping a keen eye on the girls and made sure to take note whenever they disappeared. This could, of course, be a bathroom break, but he had a feeling it wouldn’t be. Once the meal was over, he and Katie spent the evening enjoying the party and dancing, all the while Jack remained on constant alert. Katie, as she normally did at these events, got quite drunk and went to bed around ten o’clock. The girls were still up but definitely starting to show signs of being intoxicated, so Jack held on and spent the time talking to family at the bar. Around eleven o’clock, Jack realised he hadn’t seen Lily or Ella for a while and decided to make his excuses and go to bed.
On the walk up to the room, his heart pounded. The anticipation and adrenaline was almost as addictive as the act itself, and he always loved this part. It was excruciating, but in the best way. Jack decided to check his room first and opened the door as quietly as possible. The room was dark, and he could hear the heavy breathing of Katie. He quietly shut the door behind him and crept further in. As the room opened out past the bathroom on his right, he saw Lily’s bed. He stopped and let his eyes adjust, and could see her on top of her covers in a pair of pants and the top she was wearing earlier. Jack took this as a good sign, as normally she would be in pyjamas; however, she had clearly come in drunk. His cock started to rise, and he couldn’t resist a squeeze of her ass. He quickly checked to make sure Katie was completely asleep and then moved back to Lily. He leant down and slipped his hand over her ass, feeling it in his hand and squeezing it sensually. He then slipped his hand up her inner thigh and rubbed it over her hot pussy. He quickly pushed her panties to the side and slowly slid a finger into her, pausing to listen to her breathing. Hearing that all was normal, he then slid a second and then a third. She was so tight, and her moisture coated his fingers. With his other hand, he slid his cock out of his shorts and rubbed the juice on his swollen head. He was going to rub this on Ella’s lips so she could taste her.
Walking away from Lily was incredibly hard, but something Jack knew he had to do. He tucked himself back into his shorts and slowly left the room, making sure he was silent. Back in the hall, all was quiet, and he walked down to Ella’s room. His heart pounded. He had no idea if she had the same reaction to drink as his two girls, but the throbbing cock in his shorts was ruling his brain. He needed to fuck, and he didn’t want to be gentle like he had been with Lily; he was ready to lose control.
He approached Ella’s door and was thankful it was late—he really didn’t want to be caught sneaking into this room! He knocked quietly on the door, thinking he could say he couldn’t find Lily if she answered. He knocked again and pressed his ear against it. He couldn’t hear anything and hoped that she was passed out.
Jack swiped the key card, and the door clicked unlocked. He opened the door, and the glow of the side lights by the bed glowed warmly. He shut the door and called out Ella’s name softly. There was no reply. Jack crept forward and moved past the bathroom. As he rounded the corner, he saw Ella sat up in bed, partly slumped in a drunken sleep. The vodka bottle, alcopops, and Buzz Balls were all empty, with one next to her on the side table. She was sat fully dressed; however, her denim skirt had ridden up around her waist, and he could see her pink, lacy panties peeking out. As he walked over to the bed, he could hear her breathing heavily and sighed audibly. He called her again and shook her. She didn’t stir, and he felt his cock throb again. The nerves had kept him hard the entire time. Now was his chance to teach this girl what being a little slag was all about.
The first thing Jack did was walk to the bed and grasp her ankles. He began pulling her down the bed. She slid slowly, her head flopping to the side as she moved. This was going to be the test to see if she would stay passed out, and she did, giving a little snore and grumble as she was pulled onto her back. Jack then moved up the bed and rotated her so that her head was almost hanging off the bed. Her hair was a mess, and he could see her chest heaving up and down in slow breaths. He quickly took his shorts off and pulled his boxers down, releasing his aching member. Lily’s juice had dried, but he took hold of his cock, moved Ella’s hair out of the way, and rubbed his head all over her face and lips, loving the feeling of her soft, youthful skin on him. He stroked himself as he slapped her face, getting harder with each one and feeling his inner lust exploding through him—all the frustration and disappointment from earlier flowing through him as he stroked himself on her face. He pulled her towards him, and her head leant back to provide the perfect angle for what came next. He pinched her nose, a trick learned from his experiences with Lily, and waited five long seconds before her mouth opened to breathe. He then forced his cock into her mouth and felt her perfect tongue push over the top of his head. Jack groaned and kept pushing, seeing how far he could take this. He watched as his cock slid down her throat and was shocked when she didn’t gag. He began slowly fucking her mouth as he marvelled at this little slut’s abilities already. As he looked up, he saw her breasts swaying with the rhythm. He quickly and forcefully pulled her top up and her bra down, not taking the time to be careful, and was presented with a perfect pair of D-cup tits. Her nipples stood proud, and her areolas were on the larger side, which he liked. He grabbed hold of them and used them to anchor him while he fucked her throat. He wanted her to know she’d been raped. He mauled them and kneaded them as he fucked her relentlessly until, finally, she coughed and he felt her throat contract and tighten. The feeling was exquisite, but he didn’t want to wake her, so he pulled out quickly and let her recover. He took his cock and slapped all the spit that covered it on her face and smeared it into her tits. He knew she’d be bruised, but he didn’t care now.
Jack stood back, breathing heavily, and took a moment to compose himself. He looked down and saw her pink panties fully exposed from the vigorous movements. He walked to the other side of the bed and pulled them down ungracefully and threw them on the floor. He looked at her pussy. She had shaved, and he could see all of her glory. Unlike Lily’s, it was a lot bigger, and her lips came out like a flower. Not Jack’s favourite style, but he felt it somehow fit, and he had a real urge to bury his face in it. She didn’t look the kind of girl to have a pristine, tucked vagina, and that made him want to destroy it even more.
He dragged Ella so her hips were almost on the edge of the bed and pushed her thighs back. This spread her open, and she groaned softly in her unconscious state. Jack knelt down and breathed her in. She wasn’t as sweet as Lily, but her musk was stronger and more mature. Jack moved his face forward and pushed his tongue through her folds, loving the soft textures on his tongue and enjoying her taste. He focused on finding her clit through her folds, and when he found it, she jerked slightly. Jack froze for a second and then continued to lick it. She stopped twitching, but he enjoyed the thought of her enjoying it, even if it was unconsciously. He then ran his tongue down to her hole and was surprised to find her flowing with her juices. This drove Jack wild, and he lapped at her like an animal, thrusting his tongue into her deeply to get more. He moved one of his hands from her thigh, and her leg flopped slightly, resting on his shoulder. Moving his hand over to her, he slid a finger and then two into her hole and was surprised to find she was quite tight. Not virgin-Lily tight, but it was a reminder that she was still a teenager. He pulled out and tried to work a third in. Once inside, he curled them up and rammed them in and out, sitting back and enjoying watching his fingers fuck her hard. He loved the sight of her juices and his spit making her pussy glisten and watching it run down to her puckered ass. He removed his fingers and wondered if she’d been fucked in there. Probably not. Hopefully not. He slid a finger down and circled her tight bud. He applied some pressure, and he slid in with little resistance. This was probably down to her relaxed and inebriated state, Jack told himself. She was tight and hot, and he felt the rings of her anus move down his finger. He pushed another in and watched her asshole struggle to take it. He fingered her a few times and then pulled out, watching her hole clamp shut. He was going to make it gape by the time he was finished.
Jack stood up and looked at Ella. She was a mess of hair, spit, and juices. Her legs flopped off the bed onto the floor with her body still on the bed. Jack decided to get her into a good position to be fucked. He grabbed all the pillows on the bed and stacked them up. He then grabbed Ella and turned her over, manoeuvring her body so the pillows were under her stomach, putting her into a slumped doggy position. She wasn’t the heaviest; however, it wasn’t an easy task, and Jack was panting by the end. Ella hadn’t made a sound and continued to snore lightly. He was amazed she was the same as Lily, but so happy she was. As he stood back, he moved behind her and looked at the sight in front of him. Her legs were slightly parted, and her ass looked incredible. He could see her pussy puffed out, and her folds looked so inviting, and her asshole looked pink and tight. He moved onto the bed and pushed her legs apart as far as they’d go and got between them. He stroked his cock and rubbed the head up and down her pussy, spitting on her and using it as lube. He ran the head through her folds and groaned, probing her entrance before taking some of her juices and smearing it onto her ass from his cock. He loved the feeling of her tight ring flicking against the most sensitive parts. Jack then pushed it back and began to slide it into her pussy with surprising ease. She was tight but had clearly been fucked a few times. Jack bottomed out easily enough, with the last two inches being slightly more difficult, making him grunt with pleasure. He looked down at her and took her ass cheeks into both hands, and his mind lost the little control it had. He used them to steady her as he began fucking her. He drew all the way out and slammed himself back into her, feeling his balls slap against her folds. He moved his hands to her hips and began to fuck her properly. Jack tried to be careful with Lily, but he wanted Ella to know she’d been fucked. He slammed in and out of her, panting and grunting. He spanked her ass and watched as a red mark came to the surface, which made him smile with sick pleasure. His eyes drifted to her asshole, and he spat down on it and used his fingers to push the spit in. He fucked her slowly but deeply as he fingered her ass. He looked around the room, and his eyes rested on her hairbrush. He quickly jumped off the bed and grabbed it and ran back over to slip himself back inside her pussy. He spat on the handle of the hairbrush a few times and pushed it into her ass. The handle was wide enough that it made her skin stretch, and it took a bit of force to slide it into her. Jack was completely motionless with his cock about halfway inside her. He began to push the brush in and out, watching as her ass accepted it and eventually relaxed. He popped it out and saw her gape slightly. This was all the invitation he needed, as Jack slipped his cock out and pushed himself against her pink starfish. The brush had done something to loosen her, and his head popped in. Jack groaned deeply and began sliding his swollen member into her. He couldn’t believe the grip she had on him or the fact she hadn’t even stirred! After thirty seconds of pushing, he was at the hilt and bottomed out in her. He pulled back and began to slowly fuck her ass. He had done well to not come up to this point and was surprised it hadn’t been harder, but now he was starting to get overwhelmed. Her ass gripped him as he pulled out, and he felt it squeeze him. He picked up his pace, and he felt his balls begin to tighten. Jack pulled his cock out and plunged it back into her pussy and thrust into her while looking at her asshole closing up. He then pulled out and slid back into her ass. This was getting too much, as Jack began to pant and moan. He felt the tightening and pulled himself out, stroking himself and aiming for her ass. He used all his strength not to yell out as he came. His first shot blasted against her pussy and splashed onto her leg. The next ones coated her cheeks and asshole beautifully. Jack was on the verge of passing out but held it together.
Once his orgasm eventually subsided, he stood back and admired his work. Ella was completely coated, and that’s how she was going to stay. He knew it was incredibly risky, but he didn’t care. This little slut needed to know she’d been used, and he couldn’t wait to see her struggling to walk tomorrow. Jack dressed and snuck out of the room, returning to his own room. He quietly showered and slipped into bed. As he was drifting off to sleep, Jack had an interesting idea. If Katie and Lily were both as bad as each other, maybe he could have them both. A full day of drinking and having them both in the same room might not be so bad after all.
🔞 Candy.AI 🔥 AI Sex Chat – Roleplay, Erotic Stories, Try for Free 🕹️