What if… Jackie Showed Up After Graduation Ch. 4 [M/F] (Janice)

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=== ***Chris*** ===

We have a super secret way of contacting her. We have to be careful, super careful, because [Janice](https://64.media.tumblr.com/82fd7e9989bf2221d9ea58179534a178/9e4d4d351e0f0122-1b/s540x810/d3cbb5b34ed52fc1709974c16309fedcc98918b0.jpg) is very particular in how we contact her.

Janice is a local judge, and Eve and I just call her that: Judge. Janice is an intimidating woman and the fact that she’s a judge made a lot of men not want to deal with her, but I saw her for what she really is: a woman looking for intimacy.

Well a week later she calls me up and asks for a date. Of course I told Eve, I told her about it after meeting up with her in the bar. Eve liked the idea of having a judge on our side, so she kept Janice off the books, pro bono. We wouldn’t want Janice’s career in jeopardy if something were to happen to us.

Janice is single. Her pursuit of her career development meant that she focused all of her energy for it. By the time she realized she wanted more in life than her career, she’s already a woman in her early 40’s. Still, she kept her figure though and she’s mindful about that.

Janice is caucasian, standing at about 5’8 give or take, and she likes to wear black pencil skirt, white blouse and a black blazer. Typical business attire. She has a slim figure, you wouldn’t know it under her judge’s robe, and she keeps her long, dirty blonde hair tied behind her. She has to wear glasses, red rimmed and it somehow accentuates her blue eyes.

She didn’t look her age. She took care of herself, obviously. I would have mistaken her for a young 30-something, but a bit of crows feet is apparent.

Janice is a career woman. She buckled down in college and got her law degree and passed the BAR exam. Then, she focused on her work and made partners. Then, she earned her judgeship. All this while she’s only 41 years of age.

This tunnel vision for her career came at the cost of several things: she has trouble separating work from the rest of her life, she has trouble maintaining meaningful connections with people, and she easily intimidates others because of her career. She also has a little trouble with social interactions.

So, for a long time, this meant that she has not had any sexual partners – or any boyfriends, really – in all of her teenage and adult life!

So, how did she and I meet? Well, Margaret’s parents basically told her what I did. They’ve known each other for a while, Janice used to actually babysit Margaret when she was a toddler and Janice was younger. We’ve met and talked, just to get the awkwardness out of the air, and she and Eve exchanged numbers.

So now, we’re meeting up at her place. This was a long time coming and she finally has a couple of days off.

Before I go off to visit my parents, I sent my brother and his wife away. They were a bit angry at what Eve and I did, but they went back to their home with my promise that I’ll follow as soon as I finish up some business.

Sure, they only have my promise to rely on, but that’s all they’re going to get from me.

I have no idea how Janice is. I have no idea what she likes. I don’t know if she’ll call the cops or anything on me.

===

“Alright, slugger, make me proud,” my darling wife said with a parting kiss. She rubbed my cheeks and gave my face a little tap, before I closed the doors and went on.

Her house isn’t remarkable or anything. Nothing fancy but another suburban home like the rest of the houses around. She has gardeners working to keep her yard nice, clean and well kept.

I knocked on the door and within seconds she came and answered. She has on a tight little red dress, a cocktail dress from the looks of it, and her tits are bulging out from the top.

“Hmm, Chris, was it? Harold and Linda spoke highly of you,” she said with a smirk, “I hope you won’t disappoint.”

She stepped aside and walked back further into her home and I followed suit.

She has a very quaint home. Lived in and homely.

“I really hope you’re just as good as what Linda claim to be. I’d hate to give Linda a scathing review of my time with you.”She chuckled lightly as she took a seat on her couch. I took the seat next to her and she crossed one leg over the other.

Her approach is a little old fashioned. She looks really sexy, and very beautiful. Her hair is in slight curls at the end and her glasses sits on her face really well.

But I’m a little impatient. I grabbed her shoulder and pulled her roughly to me, while my other hand went to the small of her back.

“Listen to me, you little slut,” I snarled as I looked her dead in the eyes, “we’re going to go up to your room and you’re going to change into something more comfortable. Then, you’re going to make me a sandwich. I’m going to eat that sandwich.”

She looked at me and I could tell there’s some conflict in her eyes.

Her lips quivered, curling into a sneer, but my lips pressing against hers finally got her the answer she wanted. She pounded her little fist on my chest, pulled at my hair and scratched at my arm.

She wanted to establish herself as the dominant one. She wanted to be the one to take me, I could tell. But her chance is gone the moment she and I kissed.

“Ok,” she uttered softly, breathlessly. She got up and took me by my hand and we went off towards her room.

Her room is boring. Really boring. Plain, white curtains on plain white sheets and beige carpet. Barely any color in this room.

She bent over seductively and started rummaging through her drawers. She slowly, one by one, held up each shirt and shook her head no. I got impatient, and pulled her away and then pushed her on the bed. I dug into her drawer, retrieved a gray pair of shorts and a white tank top, and threw it at her. “Put those on,” I said with a huff and she just nodded.

She slowly took off her red dress, revealing a pair of black bra and lacy thong. “Put the bra away, keep the panties,” I told her and she did as she was told. She sheepishly, and shyly, took her bra off and revealed a nice set of perky tits for me. She stuffed herself in the tank top, and her beautiful, thick legs and ass into those shorts.

“Now, I want a sandwich. And make it fast,” I said and I hurriedly pushed her out and back to the living room.

“What kind of sandwich?” She asked.

“What kind? Whatever you can make! Hurry up, I’m fucking starving over here!”

Within a minute she came back with a roast beef in white with mustard, on a plate. She sat next to me while I snatched the sandwich away.

“Good job,” I growled. I grabbed her by the back of her head and pulled her in close. “Now, you’ve been a good girl,” she nodded, “and good girls get a nice reward.” Eagerness is in her eyes as it lit up, expectantly.

I undid my jean’s buttons and unzipped myself. I lift my hip up and pushed my pants down. I’m sitting on her couch in only my boxers and she’s looking down while licking her lips.

“Tell me what you want,” I asked if her.

“P-please, let me see your dick,” she muttered softly.

“I’m sorry, care to repeat that? With a little bit more politeness.”

“Let me see your dick, please sir,” she repeated and I nodded at her. For someone her age, and a virgin, she has some idea of what she wants. I took a bite out of my sandwich, chewed it for a couple of seconds and swallowed it.

“I need a drink,” I said. She looked at me, waited for a couple of seconds before I sighed in feigned frustration. “Now! Do I need to spell it out!”

“I’m sorry, sir!” She yelped as she hopped up and bounced her way to the kitchen. “What would you like?”

“What do you think!? Whatever goes with this sandwich you made!”

A few seconds later she came back with a glass of iced tea. Not really my preferred drink, but it’ll do. She sat next to me again, just waiting patiently. I took another bite and chewed it thoroughly, and slowly, set the plate with the sandwich down next to me and unbuttoned and unzipped my pants. I lifted my hips up slightly and took my jeans off, leaving my boxers on, and looked at her.

She draped herself down over my pelvis, whining and purring while she looked at my bulge. “Don’t you dare touch that,” I told her and she whined like a wounded kitten. I took another bite, slowly chewed it while looking at her while she looked at my growing mound, then took my boxers off like how I did with my pants.

“Oh my,” she said softly. She reached for it but then flinched, remembering what I had just told her.

“Don’t. You. Dare,” I warned and she nodded swiftly. She watched as my cock twitched and flexed, and her face rests almost next to it.

“Another. I want another sandwich,” I said, “come on, I’m still hungry!”

She jumped up and made another for me and as she sat back down and hands it to me, my hand shot up, grabbed the back of her head, and shoved her face down near my cock. I placed the plate down on the end-table next to me, atop the other one, and I jerked myself off while she watched me from an inch away.

“You must really want this,” I said and she nodded, “sexually frustrated and hungry?” Again, she nodded. “Tell me what you want me to do.”

“Please, let me suck your dick. I really need it.”

“You’ve been a sexless virgin for a long time, why now? What changed?” I proved and she whimpered quietly.

“I’ve been having fantasies. A lot more than usual. Me, getting taken while walking down the street. Me, getting told what to do. A man forcing his dick into me. It turns me on so much!”

I smirked as I rubbed my cock all over her face and she sharply sucked in air. “What do you know about sex? About sucking a big dick? Someone like you? Huh?”

“Please, let me taste it! It smells so good!”

I grabbed the base of her ponytail and pulled her up, then I lead her open mouth over my dick. She hung there, with her mouth open, tongue and lips waiting, and slowly I lowered her down until I felt her wet tongue wrap around my throbbing head. That relieved moan she gave as she started sucking and licking and lapping my dick up is music on my ears.

“Oh yes, it taste so strong! I love the taste! I love it!” She moaned strongly as she stroked my dick and sucked at the head. Sure, she has some learning to do, and she could barely go near her throat, but her enthusiasm is something to watch.

I went back to eating my sandwich while she sucked me off, with my other hand resting on her head. She bunched up her tank top over her breast and I could feel her nipples rubbing against my thigh, erect and hard from her arousal.

“You’re not very good at making sandwiches,” I told her and I got a short whine from her as she shot me a dismissive look. I didn’t like that, so I grabbed her pony tail and pulled her up. “What was that look for!?”

“I’m sorry! I’m sorry!” She professed while her hands worked my shaft. I looked at her, how her saliva stained her cheeks. How her pink lipstick is stretched across her lips and the surrounding tissue. How her tears are smeared all around her eyes. I pulled her in close and kissed her, softly biting her lips and sucking on her tongue.

“Good. You’re a good slut.”

“Next time, I want a proper roast beef sandwich,” I added and I let her hair go. “Kneel on the floor,” I told her and she obeyed, quickly getting on her knees while looking up at me with her blue eyes. “Let’s see how deep you can take me.”

“Open your mouth,” I grinned and her mouth opened wide. I slid my cock in on her extended tongue, feeling it’s wet roughness on the bottom of my cock head. “You need to drink more water, you don’t want your throat and pussy to get dry,” I groaned as my hand went to the back of her head and I slowly pushed my cock deeper.

She didn’t get too deep. Just enough to the back of her throat, but it’s good enough. “I’m going to break you in,” I told her and she moaned softly, and every once in a while she has to cough. My hands went to the back of her head while I roughly fucked her face, and she would cough and gag from time to time. Every once in a while I held my cock as deep as she could take it, going just a touch deeper as she gets used to it.

“Oh god!” She gasped as a pool of spit clung onto her bunched up top. “Fuck, I… I…”

“Go and get a glass of water. You need to hydrate,” I told her with a disappointed shake if my head. She got up and shakily walked to the kitchen and came back with a couple of cool bottles of water. She popped one and chugged it thirstily, gasping as she looked towards me. I sat back down and bid for her to come.

Her cool lips and tongue wrapped around my cock again, a somewhat different and arousing feeling. Soon her tongue warmed up and I could feel the gradual temperature climb. “For a virgin, you’re pretty good at giving head,” I told her and she gave me her big eyes and nodded.

“I practiced,” she said as her lips wrapped around my balls. “Practiced just for today.”

“Ooh, I like your work ethics. Good girl,” I crooned and she nodded. “Is that all you practiced?”

“I didn’t use the dildo. I figured you’d want to take my virginity,” she smacked her lips as it clung onto my balls again.

“Very good!”

“Thank you,” she said with a warm smile, “I’m a good slut?”

“A very good one!”

I reached over and grabbed her ass, fondling her fat ass while feeling it spread all over my hands. I pulled at her thong and she winced and cried out. “Sit on the couch. I want a taste,” I said and she smiled and nodded as she got up and sat with her legs spread.

“Have you ever fingered yourself?” She shook her head. “The dildo, did you use it in your pussy?” Again, she shook her head. Really, this 41 year old virgin might still have her hymen intact? That seems too far fetched!

I wouldn’t want to break her hymen if she has one. I prefer using the old fashion method of breaking it. I pulled her shorts off roughly and her panties went with it. I pushed her legs aside and looked on at her special box. I softly traced her pretty lips with my finger, noticing at how wet she’s gotten from all the excitement. She looked over to me with reddened face and her lips softly biting her index finger.

As soon as I started sucking on her clit, her moans became louder and louder. I’m afraid the workers outside would overheat us, hopefully not, but she seems to not mind. Her shaky, loud moans reverberated in her living room as her torso laid back and she started convulsing.

“Ooooh, fuck! W-What is…? What!? Fuuuck!!” She screamed as I fought to keep her legs open. Her hands grabbed my hair as she pushed me into her delicious mound, and I made sure not to go too deep into her pussy. Just enough to tickle her a bit.

I wiped my lips as I emerged from below and grabbed my cock as I poised myself before her lovely, pink slit. I pulled her head.up by the back of her neck, “watch it. Watch me put my dick in you.”

I rubbed her slit with my cock, making her hum lowly, and as I push through that membrane of hers, causing her to yelp put suddenly from the sharp pain, she hissed through it as she watched me go into her.

“It hurts! Oh it hurts!” She cried out as a little more went into her.

“Shut up and give it time,” I groaned, “fuck, that’s a tight one! Your 40 year old pussy feels nice around me.”

“You’re tearing me apart! It hurts!”

“Shut up! Just be patient!”

I slowly slid into her, only about a couple of inches in, and then back out slowly. Her pained grunt and groans eventually turned into moans of pleasure as her grimaced face transforms into a face filled with lust. “Oooh fuck, that feels good! Oh that feels so good!” She moaned loudly as she clung onto my arm.

“See? I told you,” I laughed, “now just let me do the work.”

She became more aroused as her cervix pulled back, allowing me to reach her deepest spots. Once I did, her tone changed. It went from a sensual, sexy moan to a primal grunt.

“Holy shit! Keep going, you’re fucking me so deep!” She said in a shaky voice. Her ankles went next to her ears while I pushed down on the back of her thigh, allowing me to penetrate even deeper into her. With long strokes I fucked her freshly taken pussy.

“Open up!” I told her and she didn’t know what it meant. I got my cock out and jerked it off as it pointed at her. Within seconds, I shot off long ropes of cum at her, landing mostly on her face, neck, breast and stomach. A couple strings got on her hair.

“Oh it’s so warm, sir,” she crooned as she laid there, basking in the warmth.

“What are you doing? You’re supposed to wipe it all up and put it in your mouth!”

“What? But that’s —“

“Are you talking back? Do it, now!” My tone left no grounds for bargain as she hesitantly wiped up each threads of cum with her finger. She then, gingerly, placed each creamy finger into her mouth.

“Savor it, you better get used to the taste,” I said and she nodded submissively.

“It’s salty,” she said with a disgusted look on her face. It took her a minute to gather it all up and swallowed them, but she got it all.

“So?”

“I… I don’t hate it, sir,” she answered.

“Good. A slut’s first cum should always be a facial and you’re supposed to savor the taste. Now, we’re not done yet.”

I pulled her back and brought her ankle up and near her head, pushing down on her thigh. “The second one is always a creampie.”

“What!? N-No! Sir, I’m not on any birth co— Ahhhh!!”

Before she could finish, I plunged myself into her and dig deep, rubbing against the entrance of her cervix and punching the deepest parts of her. I looked at her as she bit the fat of her thumb and her eyes rolled back, her tongue out and hung limply on the side of her mouth.

“I’m. Not. On. The. Pill!” She managed to say after each long stroke.

“Then you better get a morning after pill later!” I shouted at her, “I’d be on the pill if I was you, unless you don’t want to have sex anymore.”

“Okay. Please, be more gentle sir!”

“You dirty bitch, don’t tell me what to do!”

I pushed myself as deep as I can, our pelvis looking like one form. She gave a howling moan as her pussy clamped down and squeezed me tight, refusing to relinquish me but I managed to pull my cock back.

“I’m cumming! I’m c-cumming!” She said with sharp inhales. Her legs jerked and hobbled but I kept her pressed down. Her eyes rolled to the back of her head, and then she went limp.

“Janice? Janice?”

She fainted…

===

A few minutes later, I heard her sharp gasp as she scrambled back against the backrest of the sofa, grabbing at the cushion and putting it in front of her chest. “What happened!?” She demanded and I laughed as I drank the last bit of the iced tea.

“You passed out,” I told her. She looked around and then it finally hit her and she replied with a laugh of her own.

“I guess my brain couldn’t handle it,” she continued. “Holy shit, why did I miss out on this?”

“Well, you can enjoy it now.”

I sat next to her, propped my feet up on the table and drew my arms out across the backrest. “So, what now?”

She pushed her hair to the back of her ears. “This might be too forward, but could you… impregnate me?”

“Hmm? Are you sure?”

She’s taken aback. “Oh, I would’ve thought you’d be shocked by my request.” I just shrugged at her.

“Listen, you’re a judge so Im going to use my 5th constitutional right. But let’s say there’s a man who gets paid money to have sex with women. Now, some of these women have been taken advantage of by men because of certain disabilities. One is blind, the other is deaf. But they’re good women who each have an amazing family. Now, these women have asked the man if he could get them pregnant. The man agreed, and now these women each have a child and, maybe, they’re pregnant with another. The man was happy to do it.”

She drew closer to me and she rests her head against my chest. “So, will the man grant my request?” She asked.

“He might. Now, the man has stipulations: no child support, he still gets visitation, and upon request he would like the child to meet their siblings later on.”

“Well, what about my rule? The man has no say in how I raise my child.”

“The man understands and agrees.”

Her face went into a subtle smile. “Okay then.”

===

“Just lower yourself down. Make sure it’s in the hole.”

She has my cock pointed right up into her, but she’s hesitating in lowering herself down. She stared at it, right at the cusp of her pussy, and with a sharp inhale she lowered herself slowly. “Fuck! Fuck, it’s stretching me! Oh fuck, that’s a fat cock!”

She sat on her shin while the rest of my dick disappeared into her. “Good, now just bounce on it, or you can rock forward and backwards.”

She rocked herself, moaning passionately with each stride. I grabbed her juicy ass and pulled her down, slapping her ass so that she can bounce. I sucked on her tits while her ass slapped my thigh, squeezing me tightly as her pussy glides up and down.

“Fuck! Oh my god, you’re cock is so good! Oh my god!” She squealed. “I’m c-cumming again! Oh I’m cumming again!”

She shrunk down on top of my, curling up a little as she rode her orgasm to completion. She shook and trembled while her pussy clamped down on me. I pushed her off me and got her on her stomach flat while I climbed up behind her.

I spread her tight pussy apart and inserted myself into her which made her yell out. “I’m not ready! I’m still cumming!” She complained, but I just pressed my hand against her mouth while I continued. She might not be ready but her pussy welcomed me and hugged me nicely, fitting snugly around me.

I fucked her, slamming my pelvis against her bouncing cheeks while keeping her torso down. She bit the cushion, clawed against the arm rest, and slammed her fist against it as well. I’m chasing my own orgasm, feeling myself starting to catch up to it.

“I’m going to cum inside you. I’m going to fill you up. Get on your back, it’s better that way!”

I filled her to her back and she spreads her leg for me while I punched my dick deep inside of her. She watched as my cock pumped in and out of her like the pistons of an engine, she hoots and howled every time I dug in deep, and the final time I pressed down into her, I felt my cock expand and explode.

Warm goo wrapped around me as it flowed into her deep crevice. She wrapped her legs around me, her arms went around my back as she gave stifled gasped and short moans. With each pump of my pelvis I gave a grunt as I emptied more into her.

“It’s so hot!” She let out, “oh fuck it feels so good!”

I made sure to swirl my hip around her. She looked down as I draw my cock out from her and she grunted when I popped out. I placed a pillow behind her hips, and told her not to move for a couple of minutes while I shoved my cock into her.

“Get used to the taste,” I said, “you’ll be getting more in the future.”

She sucked my cock clean, using her tongue to scoop up the build up of film. She moaned with satisfaction as her tongue flits about.

“I can get used to the taste,” she said with a wink, “say, do you have more in the tank?”

“More? You want more?” I asked with a short chuckle.

“I have to catch up,” she said with a swoon as she squeezed her tits, “I don’t know when the next time I’ll see you again.”

I went and fetched my phone, telling Eve that Judge has asked for an all nighter. She gave a sad face emoji, but then said that she’ll see me tomorrow and she better get a good fucking as soon as I get home.

“Well, let’s see if you can keep up then.”

She smiled as her arms stretched and reached for me as I went and gave her a kiss. “Give me all you have, baby.”

~ End of Part 4 ~

Source: reddit.com/r/eroticliterature/comments/twnfo2/what_if_jackie_showed_up_after_graduation_ch_4_mf

1 comment

  1. Another amazing installment! We’ve missed you dear author, hope life’s going well

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