Jen’s Chaperone

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This is a single chapter story. Just meant to be a little fun.

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“Becca said no. Leave her alone.” I told Jen.

Jen responded to me, “Fuck off, Greg. Just because you tricked her into marrying you doesn’t make her your slave.”

My wife’s best friend Jen was hanging out as usual and was trying to bully my wife Rebecca into doing what she wanted. As usual.

Tonight Jen was pushing Rebecca into going to a dance club even though my wife was 7 months pregnant with our first child and tired from being on her feet all day.

Rebecca had heard enough of our squabbling. She was red faced and snarling, which was very out of character for my normally overly congenial partner, as she snapped at us. “Both of you, out!”

Jen and I responded together, “What?”

“I need peace and that’s not going to happen as long as the two of you are biting at each other.” My hormone charged wife focused on me. “Greg, take Jen to a club and keep her safe from the pervs.”

Jen grumbled under her breath at me, “Dickless douchebag couldn’t protect a ham sandwich.”

Before I could respond Rebecca leveled a blood freezing glare at her and coldly and carefully said, “Go. Get. Ready.”

Jen fled Rebecca’s uncharacteristic scorn to get ready. I quietly argued with my wife while Jen changed into the scrap of cloth she called her clubbing dress.

“Becca, I can’t take that girl anywhere.”

“Please go.” She huffed at me. “Jen needs a strong man to take care of her and I need you to get her out of my hair. That girl is driving me nuts. Please do this for my sanity’s sake.” Rebecca’s pregnancy rounded face implored to me. “Be nice to her, maybe you can start to be friends with her for once. It would make my life a whole lot easier.”

“I’ve tried that. She’s never wanted to be my friend. She can’t stand me.” I tried to be somewhat cordial with Jen. Unfortunately the feeling was not mutual. Ever since I first picked up on Rebecca that night I saw them sitting at a bar together, Jen had always been a bitch to me, like I was not good enough for her friend.

“It’s not like that. She likes you just fine. She just doesn’t know how to deal with you. You moved into her territory. Most men she can exercise some control over.” Rebecca smiled. “But not you, you’re the first man who dares to defy her. She’s just frustrated with you.”

“Well she frustrates me, the way she tries to push you around. Just because she likes to go out dancing doesn’t mean it’s okay to pressure you into going.”

Rebecca cupped my cheek in her palm and kissed me warmly. “Always looking out for me aren’t you. My knight in shining armor. But I’m not going am I? Look out for Jen in my place. Besides, how bad can it be dancing with a gorgeous half naked woman like Jen.”

“I’d rather spend the evening all naked with you.”

Rebecca gave me a wan smile. Our love life had begun to tail off over the last month. She still made an effort to provide some comfort to me a couple nights a week but it was not the same lusty, athletic fucking we had engaged in until recently.

“Do this and I promise you the best blow job of your life. As many blow jobs as you want. We’ll spend the rest of the weekend with you in my mouth.”

“Blow jobs for the whole weekend?” I confirmed optimistically.

I could tell she was trying to not laugh at my childlike excitement. “Go change your clothes.” she said from behind her smiling face.

I kissed her and went to put on attire more appropriate for a club. 45 minutes later I had long since finished changing and I sat waiting for Jen. Rebecca and I were discussing the color pallet of the baby’s room, but I was thinking about getting a whole lot of blow jobs over the next 72 hours; wondering if she would swallow or let me cum on her pregnancy swollen tits. I wanted to play with her swollen and distorted body. Although she didn’t see it my way, I thought she was sexy as ever.

Jen came out of the bathroom ending my conversation with Rebecca. I had to admit she looked great. Her 5 foot tall, tiny body was on display. Her slim long legs were exposed below her tiny black skin tight one piece dress. Her small but shapely ass was on display immediately above the high hem. The bottom of the dress was so high up her legs that it was a wonder that I couldn’t see her panties.

I was so distracted by the perfect legs, ass, and slim waist I didn’t notice right away that neckline plunged down to expose the tops of her breasts. She had somehow hoisted her normally flat chest into two small globes that begged to be licked.

Her curls of artificially dark red hair was pulled up in a messy pile on top of her head exposing her long neck. Her eyeshadow was smokey and eyeliner heavy. Her lips were colored dark red, almost black.

She looked like a picture of sex. Keeping men away from her in the club was going to be a full time job.

She had timed her entrance perfectly, our Uber had just pulled up.

I kissed my wife and shrugged one shoulder indifferently at Jen inviting fake hospital hastane her to walk with me out to the car. The entire drive Jen eyed me with her piercing, unreadable gaze. I responded by ignoring her.


Jen proclaimed the first club too dead the moment we walked in, so we left immediately to find more clubs for her to be displeased with.

I found us a table at the second club and a pretty blonde waitress began to flirt with me. I watched her eyes travel up and down my 6 foot 2 lean body. “What can I get for you cutie?”

“I’ll start with a Long Island ice tea.” I said suggestively. If I was single I was pretty sure we could have ended up at her place by the end of the night based on the look in her eyes.

“Um hmm!” Jen cleared her throat to announce she had returned from the dance floor.

“Oh” the waitress sounded dismayed upon seeing Jen. “What can I get for you?”

I answered for her because she always got the same thing, “My little sister will have a Vodka Martini.”

The waitress’s smile returned just before she turned away.

“I can’t fucking believe you. Trying to cheat on your pregnant wife right in front of me.”

“I’m not going to do anything. She started the flirting, I just went with it. It feels flattering to have a hot woman hit on me.”

“You are the biggest fucking douche alive. She’s just angling for a good tip.”

“Maybe, but it’s still nice. You could learn something from her about being pleasant.”

“Like where she got her boobs enhanced?”

“I was thinking more about the catching more flies was honey than vinegar thing.” I appreciatively considered the waitress’s large bust from across the room. “Besides, I think they’re real.”

“Wishful thinking.”

When our drinks arrived Jen was already carping about leaving for another club.

“The vibe in this place sucks.” she declared.

“I like this club.” I pushed back.

“We are out so I can dance, not so you can flirt and pretend like you have the balls to cheat with a waitress.”

I didn’t respond.

Jen pointed at the nearly empty dance floor. “I’m not dancing alone.” She got a devilish gleam in her eye. “Unless you want to get out there with me.”

We downed our drinks and left. We both winced at the strength of the alcohol. The waitress had given us very strong drinks.

“At least your flirting got us decent drinks.” she allowed. “I’ll give you that much credit.”

We walked down the strip to the next club. It was a repeat of the second club except without the flirty waitress. We ordered a long island and a martini. Jen danced in the sparse crowd while I waited for our drinks. She came back when our drinks arrived.

She kicked back her martini like it was water. “This place sucks.” she said.

“You don’t like the ‘vibe’?”

“Finish your drink. Let’s go.”

I gulped down the long island.

It was getting later and the clubs were getting busier. We walked in the next club. I thought we had found the place. We ordered our drinks and Jen disappeared into the crowd on the dance floor. As soon as the drinks arrived Jen reappeared and down hers before disappearing again.

Feeling a light drunken buzz, I sipped my drink and enjoyed looking at scantily dressed girls. I particularly appreciated the flashes of Jen’s body. I kept waiting for an up skirt glimpse, but the dress was staying in place only tensing me as it clung to her perfect little ass and showing her great legs. I watched Jen getting attention from a gentleman on the dance floor. She seemed to be responding positively to him so I let him continue without interference.

30 minutes later I ordered another round and waited at the table protecting Jen’s drink from tampering.

Then the DJ changed. Apparently he was a famous guy most of the people had come to see. He was spinning really harsh sounding electronic rave.

Jen returned pouting. “Damn it! I was having fun. I hate this crappy music.”

“What about your dance partner?”

She turned and waved to him. He looked at me and winked. “Yeah, he’s gay. He was just using me to dance.” She got a snarky grin. “I told him you were gay too.”


“I tried to get him to come over and flirt with you, but he said he could tell that you only had eyes for me.”

I looked at Jen startled.

“Yeah, I know.” she laughed. “He totally missed the mark with us.” She went on, “Let’s get out of here. This music is unbearable.”

I agreed with her. If we stayed, I was going to get a migraine. I handed Jen her drink which she gulped down.

As we walked to the next club I noticed Jen was drunk. Her hundred pound body was not handling the four martinis she had downed. I was buzzing hard from my four long islands as well. I helped steady her by offering my arm. She clutched my elbow and pressed her body to my side to prevent falling off the perch of her 4 inch platform heels. I ignored the fact that my arm was being pressed to the flesh between her boobs. fake taxi porno

She bypassed the line waiting to get in. The nice part about going clubbing with Jen was that she never waited in line. She walked up to the bouncer and looked at him expectantly. He glanced at her from head to toe and moved aside to let us by. I heard people in the line groan in complaint.

Once inside, Jen swayed straight to the dance floor. This club was packed, the music was loud, and the men were converging on Jen instantaneously.

Before she even started to dance she came back and dragged me onto the packed dance floor with her and we attempted dance in the tight writhing throng. She was already attracting unwanted attention from horny guys. They got close and tried to use the press of the crowd as an excuse to touch her.

Jen grabbed my hands and flattened herself to my front before spinning us 180 degrees so that I was between her and a guy that she wanted to get away from. Although she had accomplished her goal of using me as a human shield she stayed pressed close as she gyrated.

She yelled near my ear in order to be heard over the clashing sounds of music, “You are supposed to be posing as my jealous boyfriend who will kick anyone’s ass if they come near me.”

“Okay” I yelled.

She got a coy smile and an odd look in her eyes. “No one is going to believe you, if you’re afraid of me.”

“I’m not afraid of you.”

“Prove it.”

She grabbed my arms and pulled them around her, positioning my hands on her ass. She looped her arms around my neck and rested her head on my shoulder as her hips swiveled side to side against my rapidly tightening pants. We were tightly grinding against each other to the music. She had to feel me getting hard due to the friction.

I let go of her ass and tried to make space between us.

Jen desperately begged, “Pretend I’m Becca. Touch me like you do her. Unless you are a coward.”

Jen turned her back to me and pressed her butt against my hard cock. She leaned back resting her head on my chest.

Her seduction was torturing me. “Jen, please stop.” I plead through gritted teeth

She turned her head and stressed, “I’m Becca. Be brave and just close your eyes and hold Becca.”

She pulled my arms around her and twerked her hips using the cleft for her ass to stroke me. I closed my eyes and let my fuzzy mind drift to thoughts of Rebecca and what I would do with her. I wanted to fuck Rebecca so bad. The tight willing woman in front of me could be a proxy for that lust. She slid my hands up onto her tits, and I graciously squeezed. I gave in and leaned over her to bite at her earlobe. She moaned and turned her head until her tongue was in my mouth.

After two long, elicit seconds I pulled away. “Jen, I can’t do this.”

“I know.” She answered dejectedly. “You’re too good.” She turned to face me with the look of loss on her face. “Pretend to be a bad boy. Pretend you are like the assholes I usually date. I can be a bad girl for you.” She closed the space between us placing her face looking straight up under mine. Her hand reached up and she lovingly stroked my lower lip with her thumb, her fingers caressed my stubbled cheek. “I can be really bad.”

“Jen, please behave.”

She became petulant. “Becca behaves. I’m naughty. Let me be naughty for you. Use me. I want you to use me.”

“Please stop pushing me. I might break. Jen, you’re incredibly sexy. I can’t handle the teasing. You are just too gorgeous for me to resist. “

She stopped moving. “Thanks” she said. “Please dance with me.” she stressed.

She gave me a millimeter of space and we danced.

Five minutes later loud high energy song came on. Jen cheered and started to grind on my body constantly.

“Treat me like a woman!” she demanded.

She put her hands on my shoulders. I forgot myself and placed my palm in the small of her back pulling her against me. She wrapped her leg around mine and pressed her pussy against my thigh.

She said in my ear, “That’s better. The creeps are giving me space now.” She licked my earlobe and grabbed my ass. “Show me what you would do to Becca.”

In a moment of misguided drunken lust I closed my eyes and imagined that it was Becca in my arms. It was her warm body grinding against me with the promise of sex later in the night. I palmed her ass and stroked my cock against her belly. She latched her mouth onto mine and as we made out I cupped her breast slipping my fingers inside her top to find a nipple. I wanted to take her then and there.

“Oh god Becca, I love you.” I gushed.

We both froze. Jen slipped from my loosening arms and wedged herself back into her dress.

We danced in uncomfortable silence for another couple songs. Luckily the last call announcement came on. I was surprised that it had gotten so late. We had been out for a several hours, but it felt like a flash. I grab her hand and along with most of the crowd I dragged Jen out of the stuffy club into the chill night air. family stroke porno

Jen was shivering as the frigid night air froze the sweat on her glistening body. I automatically gave her my coat which she accepted politely. We stood quietly waiting for the Uber driver to collect us.

We didn’t speak another word the entire way home. She seemed unable to find a comfortable position and continuously shifted in her seat. Her long legs were entirely exposed and as her dress worked up even higher I was finally getting glimpses of her panties that I had hoped I could sneak a peak at. They were low cut, lacy, and transparent red and when she slumped low in the seat she slid her hips forward exposing the gap between her thighs they pulled tightly against her lips showing me everything. I imagined licking at her puffy labia. Grabbing her tiny hips as I used her, penetrating that sweet little pussy.

I needed to get laid. Rebecca had recently called a moratorium on sex until the baby came but promised to give oral frequently. She gave great head. I was going to need her to suck me off soon.

Assuming Rebecca was asleep, it seemed likely I was going to have to find satisfaction with my hand while I showered tonight. I promised myself I would think of my wife while I jerked.


We came home to find my wife awake, playing a game on her iPad. I looked at her beautiful rosy face framed by her bobbed blonde hair.

Jen laid herself out on the sofa with her arms and legs spread wide. I could easily see up her skirt and view her underwear.

“Did you have a good time?” Rebecca asked without looking up.

“The clubs sucked but I had fun.” Jen announced.

“Yeah, it was okay. You should be sleeping.” I told Rebecca hoping that her being awake meant I might be able to get some relief with her. A handjob would be wonderful right now.

“I slept some. But your daughter woke me up a little bit ago. I think she’s playing soccer in my belly. Since I was awake, I decided to wait up for you guys.”

I helped Rebecca up to her feet and hugged her. She immediately felt my boner as I pressed it into her stomach. She reached down and grabbed my cock through my pants.

“Damn it Jen!” She yelled. Jen opened one eye and looked at us. “You did this on purpose, didn’t you. You probably rubbed on him all night.”


“Now I’ve got a horny man who needs release on my hands.”

“You married him, he’s your problem.”

“Oh no you don’t. Get your ass over here. You’re going to take care of this.”

I thought, ‘Wait, what?’ as my mind tried to make sense of her words that I assumed I had misunderstood.

“I’m sure he is well acquainted with taking care of it himself.”

Rebecca sternly ordered, “Get over here now.” To my surprise Jen swung her feet to the floor and walked over. “On your knees.” Jen continued to comply sinking down in front of me.

Too stunned to respond, I watched my wife open my pants and fish out my cock. Holding my throbbing rod in one hand, she fisted her other hand in Jen’s hair. Jen opened her mouth voluntarily while Rebecca guided it onto my 7 inches of thick circumcised stiffness.

Jen sealed her lips around me and began to suck. All the while Rebecca stroked the lower half of my cock with one hand and moved Jen’s head with the other. I looked at Rebecca’s face as her blue eyes focused intently on what she was doing, smiling to herself.

Rebecca noticed my focus and reached her mouth up and kissed me. We battle tongues while her friend blew me.

Rebecca leaned back and winked at me. I felt her pushing Jen’s throat onto my cock. Jen immediately began choking. Jen turned her head to the side trying to gain control of her coughing.

Rebecca berated her, “All these years I had to listen to you brag to me about that your blow jobs are so good you could own any man. About you being able to deepthroat a guy. Was it all made up?”

“He’s really big damn it! It doesn’t fit.” Jen protested before went back to blowing me on her own accord without Rebecca’s guiding hand.

Rebecca whispered in my ear, “Don’t cum yet. I have some ideas. You’re going to have some fun tonight.”

Rebecca and I stood and looked down upon Jen as she happily hummed, slurped, and sucked at my cock. She appeared to be enjoying herself.

Rebecca recognised that I was getting near shooting off. She pushed Jen’s head back with a firm push on the forehead releasing me from her mouth.

Despite the fact everyone in the room knew I about to explode in Jen’s mouth, Rebecca chided Jen, “You’ll never finish him giving lousy head like that. Stand up and bend over the end of the sofa.”

Jen pulled my pants and underwear off past my feet then stood and looked seductively at me. Her lips were parted as she breathed heavily, her lidded eyes looked needy. The desire on her face suggested she was not at all upset about what was coming next. She looked more eager than anything. She turned and leaned over the arm of the sofa as directed. She thrust the ass out. Rebecca pulled Jen’s dress up until it was bunched around her small waist revealing her tiny heart shaped ass encased in red lace. Rebecca pulled the panties down and off carefully leaving the platform heels in place. Then, to my surprise, she stuck two fingers into Jen’s pussy.

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