Enny and Hypnosis

[MILF Date Night]

Kenny waited on the couch. Just as he checked the time on his phone, the doorbell rang. Ms. Feng was standing on the front porch wearing just a tight fitting white t-shirt.

"By the way, two cars saw me like this on the way over here," Ms. Feng said.

"Didn't you used to be timid about being seen like this?" Kenny asked.

"Only when it's people we know. If it's strangers on the street, I could care less."

Kenny welcomed her inside the dark house with the only source of light seeming to come from a glow in the dining room. Ms. Feng followed behind Kenny, taking a seat at the table while he went to the kitchen; returning with a silver tray.

"So, what are we doing for dinner?" Ms. Feng asked as she sat down in one of the only two seats at the dinner table. "You did tell me to come over with a not-so-full stomach."

"Well, I figured we'd have some dessert instead of dinner," Kenny said as he placed the silver tray full of chocolate-covered strawberries in front of Ms. Feng.

Ms. Feng gasped with glee.

"Kenny!" She said with a tone of someone being touched by a sincere gesture. "Chocolate strawberries? Oh, I just love these!"

Ms. Feng gave Kenny a kiss on the cheek, causing him to smile and blush. Ms. Feng took the first bite, rolling her eyes and moaning at the delightful taste of a sweet berry with bitter chocolate.

"Oh my, god," she said with a mouthful. "Dark chocolate is my absolute favorite!"

"Well, I kinda overheard you talking to your bookclub about your favorite desserts that one day," Kenny said to her.

Ms. Feng grabbed a white chocolate one and put it up to Kenny's mouth. She opened her mouth, wanting Kenny to do the same, and he took a small bite out of it.

"Oh, yeah," he said. "These definitely came out great."

"Did you make these yourself?" Ms. Feng asked, biting into another one.

"I did," Kenny answered "I got the best strawberries I could find as well as the best chocolates to melt over them."

"I just love a man who makes his honey what she likes," Ms. Feng said before licking the melted chocolate off her fingertips. "It really gets me in the mood."

Ms. Feng grabbed a milk chocolate strawberry and pressed it against Kenny's lips, also scooting her chair closer to his. She then pressed her lips against it until it rubbed against his. Ms. Feng took a bite, Kenny taking one two. Soon, the minuscule amount of fruit fell from their lips and onto the table. Ms. Feng pushed forward and gave Kenny a chocolate-covered kiss on the lips. Kenny responded by twisting his lips and licking the chocolate off hers while still pressing against them. Their tongues soon met inside one another's mouths and they completely forgot about the wonderful dessert next to them; wanting each other's sweet lips instead.

The two closed their eyes and held onto each other's heads as they brought themselves closer together. Ms. Feng was soon sitting on Kenny's lap as they continued. He furrowed his brow as he reached his hand down to her ass.

"There's... something bumpy hitting my leg," Kenny said to her.

"Oh, that?" Ms. Feng said to him with a smile and giggle.

Ms. Feng stood up, turned around and bent over. With the glow of the candle on the table, he was able to see her wearing the same blue jewel plug she had worn from their night at the school.

"Don't mind the plug, baby," she said to him, shaking her ass. "That's just what I use to keep my ass nice and ready for when my boyfriend wants to stick his cock in."

Kenny stood up and pulled Ms. Feng back, catching her in his arms. She laughed playfully as he walked her up the stairs and up to his bedroom. He flipped the light on with his elbow, then tossed her onto the bed. Once the door was closed, he faced his MILF-lover.

"No more dessert, huh?" She said to him.

Ms. Feng laid on her right side and pulled her left leg far enough towards her head for the jewel of the plug to be seen wedged between her cheeks to be seen.

"How about a late night snack?" She said, suggestively and with a smile.

Kenny took his shirt off and got down on his knees in front of Ms. Feng's ass. Ms. Feng reached back and quickly pulled her plug out with a wet *pop*, then tossed it behind her on the floor. Kenny stuck his face between her cheeks and proceeded to run his tongue across the diameter of her asshole.

"Eat that fucking ass, Kenny..." Ms. Feng softly said with mild strain.

Kenny closed his eyes and ran his hands across the side of her left cheek as he licked her ass. He couldn't see it, but could feel Ms. Feng's pussy tightening with each swipe of his tongue. Kenny felt Ms. Feng open her legs then felt a finger graze across his cheek. Opening his eyes, he saw that Ms. Feng was now massaging her pussy.

"Oh, yeah..." Ms. Feng said with a sharp inhale. "Let me tease my pussy while you get ready to tear my ass open..."

Kenny went from licking to kissing, practically sucking on Ms. Feng's asshole. He felt her go from gently teasing her pussy to sinking her fingers down to the knuckles at a moderate speed. Kenny pushed his face in closer to Ms. Feng's ass and stuck his tongue up her asshole.

"So good!" She said in a loud, wobbly voice.

Ms. Feng was moaning non-stop with each passing second. She was unknowingly rocking her own body back and forth, pretending Kenny was fucking her ass with his tongue. She shuddered as she felt his wet, hot tongue swirl around her insides; pulling in and out in a twisting motion.

Kenny slowed down his roll until his tongue and face left her ass. Ms. Feng looked down and watched him take his pants and boxers off.

"Look at my asshole, sweetie," Ms. Feng said, grabbing her left cheek and pulling it back.

Ms. Feng squeezed her ass open and shut, attempting to 'wink' at him; so to speak.

"Look at how bad it wants your thick cock inside it," she said with a desperate tone.

Kenny's cock was already perfectly hard. Ms. Feng felt nervous staring at it as he approached her behind.

"This thing's already been inside me quite a few times..." she thought to herself. "But I guess this is the first time really seeing it for the monster it truly is."

Kenny chose to rub his dick against the slit of her pussy and between her thighs instead of trying to immediately start fucking her ass. He went in and out, far enough for Ms. Feng to be able to see the tip peak out from the front of her thighs.

"If you're going to tease me..." Ms. Feng said. "Can you at least hear me out?"

Kenny stopped and looked over Ms. Feng's face.

"Think you can rest your balls against my asshole?" She asked him. "I want to feel them twitching and moving as they get acquainted with their favorite sex-hole."

Kenny complied with the bizarre request and pulled out of Ms. Feng's thighs. He gripped and pulled his cock up as he pressed the top part of his sack against the curvature of Ms. Feng's left ass-cheek. His testicles hung down and were soon gently pressed between her cheeks as Ms. Feng reached back to spread them apart further. Kenny stood awkwardly as he looked all over his room as Ms. Feng softly moaned below him.

"I can feel your balls squirming against my butt," she said. "They must really want you to release your backed-up spunk, huh? They're not picky either, they'll be happy unloading in any kind of pussy, right?"

Kenny's dick was pulsating on Ms. Feng's ass as his perineum twitched.

"You should listen to your body," Ms. Feng said in a low voice.

Kenny looked over once more at Ms. Feng's face.

"You should shove your cock up my ass," she said, licking her lips.

Kenny no longer cared if his dick was wet enough to penetrate Ms. Feng, he only wanted to feel the tight insides of her hot asshole.

"Oh, fuck yeah!" Kenny said without holding back.

Ms. Feng giggled behind her tooth smile. She soon started to lightly moan with her mouth open.

"Just like that..." she said. "That's how I like my ass stretched."

Kenny planted one hand on his bed and the other on her left thigh. He slapped his hips against her ass at a steady pace. The low, wet, meaty sound of her wet asshole gripping his cock as it slid in and out, radiated out until it could be heard by both parties.

"Go harder, honey!" Ms. Feng said to him. "I know you like it rough! You know I like it rough too!"

Kenny pushed the weight of his body down further and started to push his cock down further. He looked down to watch Ms. Feng's asshole swallow and spit out his cock, also watching it go from partially dry to completely soaked. Kenny brought his right knee onto the bed and used it to hold himself steady, then got Ms. Feng to scoot further away to bring his other leg up as well.

Kenny was now on all fours, crashing his hips into Ms. Feng's soft, big ass.

"You're a beast!" Ms. Feng cried out. "You're a monster fucking my ass!"

Kenny's cock accidentally slipped out when he pulled back too far.

"Beg for me to stick it back in," he said to her.

"Please, Kenny!" Ms. Feng pleaded. " Please tear my ass up with your massive fucking cock!"

Kenny happily complied and stuck his cock back in. Ms. Feng was moaning wildly as he went balls-to-rim on each thrust. He would hold himself in close, twirling his dick around her insides, before pulling back out; only to repeat the process.

"My poor pussy..." Ms. Feng said in a strained voice.

Ms. Feng reached down and encircled her clit as streams of liquid squirted out one after another.

"My poor pussy is cumming while my ass gets destroyed~" she said in the same tone.

"I'm... I-I'm gonna buuuuuuust!" Kenny moaned.

"Go ahead, baby!" Ms. Feng said. "Cum in my asshole like you own it!"

Kenny grabbed Ms. Feng and pulled her body closer onto his as he groaned loudly. Ms. Feng moaned in orgasmic-anguish as his cock pulsed violently inside her. She could feel the empty space of her rectum being filled with white-hot sperm while her pussy quivered and spurted once more. Kenny was arching his back while holding himself up in the air and collapsed onto Ms. Feng one he was spent.

"That ass of yours..." he struggled to say. "It's always... so god damn amazing..."

"Same about your cock, sweetie," Ms. Feng said, panting before she could continue. "Your thick cock fits so well up my tight-asshole."

Ms. Feng turned her head around and grabbed Kenny's from behind.

"Please always be here when I need some anal lovin'," she said, kissing him deeply.

The two spent a few seconds making out before crawling under the covers.

"Oh," Ms. Feng said suddenly. "There's something else I wanted to start trying and I figured today would be a good start."

"What is it?" Kenny asked.

"I want you to fuck me in my sleep," Ms. Feng bluntly stated. "If my ass is willing and ready, just go ahead and stick your cock up it whenever you feel like."

"And if I wake up, then all the better," she concluded with a wink.

The two kissed one last time and giggled as Kenny turned the light to his room off then got back in the bed. The chocolate strawberries on the dining room table could bee seen melting and the final piece of wax dripped off the candle and the wick went out.

*****

Kenny and Ms. Feng were both in his bed. His phone was set-up and recording from his desk. A caption on the video read, "fucking my girlfriend's sleeping ass while my parents are downstairs." Thanks to hypnosis, Ms. Feng would stay asleep throughout the ordeal. Kenny carefully got out of the bed and picked her shirt off the floor. A caption read, "this is the only thing she wore here." Kenny took out a black marker and wrote, "MILF" on the chest.

Next, he took a bottle of lube out of his drawer. He pulled the covers off of Ms. Feng, revealing her sleeping on her stomach with her right leg straight but her left leg pulled up to the side. He squirted some lube between her cheeks and rubbed it in, then on his cock. He positioned himself over her lower body then slowly sunk his cock in between her cheeks and into her asshole.

Ms. Feng moaned lightly. Kenny quickly covered her mouth and resumed pounding her ass. Footsteps could be heard coming up the stairs. Kenny quickly stopped and carried Ms. Feng to his bathroom, where he sat on the closed toilet lid holding her in his arms. Kenny's mother knocked on the door before opening it.

"Kenny? Are you awake yet?" She asked.

"Yeah! I was about to take a shower!" Kenny shouted back, covering Ms. Feng's ears.

"Okay! I left breakfast on the counter! Your father and I might get back late, so you're on your own for dinner!" Kenny's mother said.

"Got it!" Kenny said.

Kenny's mother closed the door to his room. Against his knowledge, the door didn't close fully and slowly swung open. Kenny opened the door to his bathroom so that the camera could record them inside. He then stood up with her and reoriented her for a standing full-nelson. With his cock back in, Kenny thrusted in and out of Ms. Feng's tight asshole; her moaning lightly. The camera showed the open bathroom door as well as the open door to his bedroom.

He walked over to the entry way of his bathroom and continued there for a bit. After a while, he looked off to the side and was surprised to see the door to his room open. Quickly, he ran over and gently closed the door. Still rock hard and aching to fuck Ms. Feng more, he carried her back to his bed. Her legs hung off the side facing his phone. He lifted her legs up and stood to the side, showing her wet and twitching asshole.

Kenny stuck his cock back in and continued to hold her legs up as he fucked her. He put her on her side and plunged between her cheeks like so. His phone captured her big ass swallowing his cock on each thrust. Kenny wanted to try more positions but reached his limit before he could. He settled on cumming with Ms. Feng on her side and sped up his movements until he climaxed deep up her ass. Upon pulling out, streams of cum oozed out rapidly and down the side of her cheeks.

Kenny tucked her back into bed then went downstairs. After his parents left, he returned to his bedroom.

"*yawn* Good mawnin'... are your parents gone?" Ms. Feng said in a whisper.

"Yeah, they already left," Kenny said back.

"Oh, in that case, want to fuck a bit before I go home?" Ms. Feng asked. "I had this insane wet dream where you banged my ass hard enough for me to cum three times before you pulled out."

Kenny and Ms. Feng proceeded to bang in numerous places around the house before she decided to head home. Ms. Feng grabbed her T-shirt, her only article of clothing, and read what Kenny had written on it.

"Really?" She said, looking over at Kenny. "Well, if this is what you want me to wear..."

Kenny walked her downstairs where she looked out the living room window and out to the neighborhood.

"It looks like the coast is clear..." she said.

Kenny opened the door for her, but quickly closed it.

"What's up?" Ms. Feng asked him.

"Whoa! You don't have any pants on!" He said, remembering that a shirt was the only article of clothing Ms. Feng had worn for their date.

"So?" Ms. Feng said back.

"So? So someone could see a half-naked MILF leave my house and walk across to hers!" Kenny said. "Why did I have to write 'MILF' on your shirt..."

Kenny quickly walked went upstairs to his bathroom and came back with a white towel.

"Here. Wrap this around your waist," he said, handing it over.

Ms. Feng rolled her eyes as she put the towel around her waist. She gave Kenny one last kiss on the lips before walking out towards the street. Not too far down the driveway, she pulled her towel off and dropped it on the concrete. She looked both ways as she crossed the street and continued to walk through her driveway and up to her front porch. Kenny watched her let herself in without a key. Just when he was about to head back upstairs, he looked through the living room window one last time and saw Ms. Feng standing in front of her own. She flashed him his tits then motioned her hand towards her open mouth as if pretending to suck a cock before closing them.

*****

Kenny answered the door and welcoming in Ms. Evans, who was standing on his front porch wearing a pair of pink panties that cut deep into her crotch.

"What happened to your clothes?" He asked, unfazed from his date with Ms. Feng.

"Oh, my!" She exclaimed in a fake tone of surprise while looking down at herself. "I must have been in such a rush that I left everything at home!"

"*sigh* Let's get you inside..." Kenny said as he stepped out of Ms. Evans' way.

Ms. Evans walked in and headed straight for the couch.

"So, how did your date with Dianne go?" Ms. Evans asked.

"Pretty well," Kenny said as he sat down next to her. "We had some dessert then spent the rest of the night up in my room."

"I also heard you sent her back home with an sore-ass leaking with cum," Ms. Evans said with a wink.

Kenny chose to stay silent.

"Since you didn't want dinner, what did you want to do tonight?" He asked her.

"Well..." Ms. Evans said. "I was thinking we could watch a movie together."

"Sure," Kenny said in agreement. "What did you have in mind?"

Kenny turned on the living room TV and browsed through the endless lineup of titles on the streaming app. Ms. Evans shortly put her hand on the remote and lowered it down.

"I had a *different* movie in mind," she said with a smile.

Kenny glanced over at Ms. Evans as she flicked through her phone. After several taps on her screen, she looked up at the TV to see it momentarily go black before coming back on to a familiar empty theater. Ms. Feng was seen walking out to the middle of the stage and waving out to the seats with a smile on her face.

"Wait a minute..." Kenny thought to himself.

"Look familiar?" Ms. Evans said to him. "It should since this is the porno you and Dianne starred in. I'm so glad she let me save a copy on my phone."

Kenny felt nostalgic as he continued to watch the beginning of the video, already knowing what was going to be said and what was going to happen next. Ms. Evans chuckled and giggled each time Ms. Feng gave her dialogue. The two continued to watch up until Kenny was called on stage. Once Ms. Feng had taken her clothes off, Ms. Evans crossed her legs and watched intently with a wide grin on her face. Soon, Kenny felt her hand run along the outside of the crotch of his pants. She rubbed it in circles before undoing the button with her fingers then pulling the zipper down. From there, she fished out his dick and gently squeezed it in her hand.

"Mmm..." she said under her breath. "I just love good, amateur porn~."

Ms. Feng kept watching the video as she stroked Kenny's dick. Kenny decided to do some teasing of his own and reached over to toy with Ms. Evans' nipples. He pinched and pulled on the left one before switching over to the right. Kenny rubbed them with his thumb, feeling them go from inverted to hard. Ms. Evans felt his big, warm hand grip onto the 'meat' of her tits; shaking them side-to-side before letting it go and doing the same to the other.

"That's good..." Ms. Evans said, spreading her legs apart.

She wasn't quite spread eagle, but had her legs spread far enough apart for her knees to nearly touch the couch cushions. Kenny looked over and saw the pink fabric of her panties pressed against her pussy, nearly being swallowed into it. He moved his hand from her breasts to it and rubbed her lips from the outside. Ms. Evans did a long exhale through her nose while arching her back and pushing up against the back of the couch.

"Keep going," she said in a low voice to Kenny.

Kenny watched the porno of him and Ms. Feng while rubbing in circles on Ms. Evans' pussy. Right at the part where he squirted lube onto Ms. Feng's ass, he took his chance to slip his fingers behind her panties and dig into her pussy.