What if… Jackie Showed Up After Graduation [M/F] (Margaret)

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=== ***Jackie*** ===

I’m waiting there under the lights, with my back against my beater of a Honda. Impatiently, I looked down at my phone, noting how it’s almost 9 PM and that son-of-a-bitch hasn’t shown his face!

“Hey!” came that familiar voice, a little deep but undoubtedly that of a teenager. Chris came jogging towards me, still wearing his lavender graduation cap and gown. “Thanks for meeting me.”

“What is it, Chris. What did you want to talk about?” I asked impatiently as I tapped my foot on the ground and crossed my arms. “I’ve got a party to go to, you know.”

I lied. I don’t have a party to go to. I’m just going back home and drink some beer. My dad doesn’t care if I drink. He doesn’t care about a lot of things.

“Um, I uh…”

He rambled. He’s not usually this frazzled or anything, so I took my keys and started tossing it up and down my hand. “Look, if you’re just going to waste my time then we don’t have anything to talk about.”

I’m a little excited on what he’s going to ask me. Chris has been my best friend since we were kids, and it’s a little alarming seeing him so grown up. I used to be much taller than him, and then sophomore year hits and he got a massive growth spurt. Massive for him, but his height is modest.

“I… I wanted to ask you if… if… if…”

“Out with it!”

I grabbed him by the collar and pulled him close and down until I’m looking down at him. I’m glaring at him, trying to put on the fiercest face I could.

“I wanted to ask if you wanted to be my girlfriend!”

I puffed up my cheeks as I pushed him away. “Is that all?” I asked, trying my best to be the same bitch he’s known.

“Yeah, that’s it,” he meekly said.

“Alright. Alright then. But, as my boyfriend, you have to take me on dates. Starting right now.”

His eyes went wide, his smile broadened, and he leapt up and hugged me. I had to push him away as he smiled in happiness.

“Oh, right now? Oh… okay, let’s go!”

He took me by my hand, and we went on. “What about my car!” I called out to him.

“We’ll come back for it tomorrow!” he replied.

===

He’s sweet.

He’s caring.

He does all the right things.

So why can’t I fall in love with him? Why? We’ve been together for a year now, and nothing. Nothing at all. I see the way he looks at me. I feel how tight he holds my hand. But nothing! My heart doesn’t jump for him.

I’ve moved out from my parent’s home. I got a job at a grocery store, and the apartment is small but comfortable, it’s a studio apartment but its mine. I gave him a key, but he’s been staying with his family and working as well.

His parents are going to move further north since his mom was offered a job up there for a lot more money, but instead of moving up with them he chose to move in with me! We split utilities and rent, he usually just gives me half of the rent and sometimes he would go and pay for groceries.

But… but my heart just doesn’t skip for him. I pretend that it does. I pretend that I miss and love him, which gets harder and harder to do. We haven’t even had sex yet and I keep telling him to wait for marriage, or to wait for us to get settled and have more money. He doesn’t push. He doesn’t ask me for any sort of intimacy other than kissing and hugging and cuddling. I like the things he does for me, but my heart just doesn’t…

What is wrong with me!?

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

I got accepted! I got accepted to the state university! This coming spring is when I’ll start working towards my goal of Computer Engineer and then I’ll really start my life. I’ve always had a love for computers, and now I get to put that love towards a career!

I picked us up some subs from the local deli store, and I drove back to the apartment to give her the good news. I’m sure she’ll be happy, she’s going to college next year for business management, but I cannot wait to tell her the news!

It’s about 6 PM right now and I put the keys into the lock. I swing the door open, and I see… horror.

Jackie, bent over the dining table, her legs wide. Who’s behind her?

Dean.

She screamed in horror. “Chris, no! It’s not what it looks like!”

I just see Dean’s face. His cunning smile, like he stole my favorite belonging. That bastard. I’ve never felt such rage or such hate. He looked… happy, almost. Happy that he’s destroying my life. Happy that he’s causing me this great pain. At that moment, he stopped being my brother. He stopped being a person to me.

I dropped everything. I dropped the mail. I dropped the sandwiches that I bought for us. I shut the door, ran back to my car, and I just… left.

I don’t know how long I’ve been driving. I don’t have a clear direction. I just drove west and I haven’t noticed how many hours have passed. My phone kept buzzing and buzzing until it finally stopped, probably because it died. I have a charger in my car but I didn’t bother plugging it in. I just drove, I didn’t care anymore. I filled up my tank, ate some shitty gasoline hot dog or pizza, and I kept driving until I ended up in another state.

I checked into some cheap motel, thankfully I have cash on me, and slept for maybe an hour. I plugged my phone in to charge and when it came to life all the messages came flooding it. There must have been thousands, a vast majority of it is from Jackie but a few is from Dean who gloated and rubbed it in.

Apparently, they’ve been doing it for a long time, a very long time, since we’ve gotten together it looks like. They usually get together when I’m not home or I’m at my job. Dean has always been mean to me, much more than what an older brother would to his younger, and since he’s the athlete of the family my dad coddled and spoiled him.

My mother didn’t spoil me, but she did teach me to be strong and be a good person. She’s always been good to me, always so she’s the one I went to call first.

“C-Chrissy? Chrissy, where ya be, me son?” came her voice from the phone.

“Uh… I don’t know,” I lied, “but… but…. Ma, why? Why me? Dean…. Dean has everything… but he’s always taken from me, but… but…. why?”

“Ach… that dumbass son of mine. If he didn’t come straight outta me, I would have never known he’s me own. But Chris… come home, aye? Please?”

I felt another buzz and another message from Dean. He’s going to marry her…

“I can’t, ma. I can’t… um… t-take care of them, ma. I’ll be fine here, I’ll be fine.”

“Chris! Don’t be stupid, son! Yer 19 years old, still a wee lad! Come home, please, we can talk about this aye?”

I sniffled. I can feel this great pain in my chest, like a rail-spike being driven inside. “I can’t, ma. I can’t. I’m too weak… I’ll be fine, I love you, ma, tell that to Albert and dad, please.”

I hung up. It’s still afternoon so I went to the ATM and withdrew all the cash from my account. I have about 20 grand on me right now which is mostly saved allowances and some summer job. I went and got a new number for my phone. I cut up my credit cards, thank god I didn’t have any bills.

I don’t know why this happened to me. I don’t know what I did to deserve this. But what I do know is I need to be strong. I need to have a heart of steel. I went back to my motel room and tried my best to get some sleep.

But I’m plagued with visions of those two. How Dean’s smile crept up the moment he saw my face. How Jackie’s face of pure ecstasy moments before seeing me. It was all very vivid in my eyes, so very vivid in my memory…

Will I ever get over this?

=== ***Jackie*** ===

It’s been five years. Five, long, grueling years. I haven’t seen him since that night. I haven’t seen him since the night his brother and I broke his heart. Dean, for the most part, married me and we’ve been together since. His mother cut us off, his brother refused to talk to us, and the only one who would even entertain us is his father, who barely speaks to us. We really did break this family, but we’ve managed to dig us out of that hole. We graduated our business management classes and got us a restaurant. Then the virus broke out and we almost didn’t make it, but we survived.

“We found him.”

Dean and I have been trying to make this family right again. We realized the great mistake we did, but it was two years way too fucking late. Dean did a lot of growing up in those two years and he finally saw how big of a mistake it was. I can say the same, thought, and it’s all our fault. We know it’s our fault, we broke the family that was so great and pure.

His father has been looking for Chris, both as a way of making it right for the family and as a way of proving to his wife that he could be a great father! Bill wasn’t as hands-on as he could be and spoiled Dean, which resulted in Dean being an asshole, so now he’s trying to make it up to his wife.

“You found him? Where?” I asked in great enthusiasm.

Dean sat down next to me and sighed, “A couple of state south-west, in some small city. The PI didn’t get any clear picture of him, but he’s very positive it’s him.”

“How positive?”

“Very.”

My hands went to cover my mouth. Finally, finally we can right the wrongs Dean and I committed. Maybe if we can get him back, we can rebuild the family back to how it was.

I can’t believe it took us 5 years to find him. He’s 24 now and who knows what he looks like since the PI didn’t get a good picture of him. The ones we’ve seen were all him either hunched down, have the papers up, or has his back turned towards us. But they’re confident it’s him and his father paid a lot of money to find him.

Chris was very into social media growing up. He used them all, but then when… well, when Dean and I did what we did to him, it has been left stagnant. The last post he made was him announcing he was accepted for the Computer Engineering program, and that was it. A 5 year old post. When he left, I picked up the envelope that fell next to some deli sandwiches, most likely for me and him, and it was a letter for him from the college.

I wish I didn’t do what I did. I wish broke up with him instead of letting the vile thing we did ruin his life! It took us some time to come to term to what we did, Dean and I, and I don’t think we can ever really forgive ourselves for what we did. I don’t expect him to forgive us, but I would like him to come back and become a family with his parents again.

Maeve has been a wreck. She used to be fun. She used to be the mother that I wanted. Now, ever since Chris went away, she focused all of her energy towards work and barely said a word to Bill and Dean. Albert was the same way. He became a lawyer and pretty much shut himself away from us. They both wanted Chris back. They both wanted the family back.

So, we travelled down there, it took us about a 15-hour drive. That’s pretty damn long if I’m being honest. The PI got us a hotel room and asked us to meet him in a nearby coffee shop.

The town gives a small-town kind of vibe. It feels old fashioned, like it was left behind in the 90’s. But there’s a lot of big houses her, a lot of money it looks like.

There’s no big superstore or anything, they have a butcher and a bakery shop and a somewhat big mom-and-pops store that sells various things. There’s a large theater towards the northern part of the town. It’s near the coast too so there is fishing is a pretty big part of the culture here.

Our PI is a very unassuming guy. He wore drab colors to blend in with the public and looked kind of… normal. I guess that goes with the job. You wouldn’t want to stand out if your job description is following someone.

“What do you have for us?” Dean asked and the man produced a folder from his briefcase. He gave us a nod and stood, “that’s all I can dig up on him. I’m paid up, so the rest is up to you two. Good luck,” he said, and he went off.

When Dean opened the folder he gave a small gasp. Finally, a pretty clear picture of him but he looks… different.

“Is this really him?” I asked and Dean nodded, “is that… no, it can’t be.”

Chris has gotten very, very… very muscular. He used to be a thin guy, not scrawny but he has a little bit of muscle on him. What I’m looking at is a pretty buff guy, not body-builder buff, but he has some muscles on him. His chest is wide and thick, his shoulders and arms are ripped, and he wears a tight shirt and shows off all the grooves and indentations of his body.

Chris was thin so all the clothes he wore was baggy for him.

Dean used to be in the football team back in high school, but he was never that big. Chris also cut his hair and he kept it short, and he let his facial hair grow so he has a short beard. There’re also several logs written down of the PI, most of it detailing how Chris has been able to dodge and slip by him and he spent some time just tracking him down. There’s some account of him going in and out of several houses, spending hours and hours in there.

From what the PI can discern, Chris lives in a studio apartment by himself, but there’s always a woman that goes in there. She usually brings along two kids, and the PI also took pictures of Chris carrying one of the kids and kissing the woman.

“He has kids!?” I gasped in shock, “Dean! H-He, he has kids!?”

Dean looked at the image and I could tell he’s a little bit sad. The kids aren’t grown, they’re probably 2-3 years old, but Dean has always wanted kids.

But Dean can’t have kids: he’s sterile. He took some steroids back in high school so he can get bigger and to perform better, but at the cost of his fertility. He’s not sterile, to be exact, but his sperm count is so low that he might as well be sterile. We’ve been trying to have kids for the longest time, ever since we got married, and I’ll admit that I have never been on birth control, and we weren’t careful even when I was cheating on Chris with Dean.

“He may or may not have kids, we don’t know that for sure,” he corrected, a little anger and sadness flaring up. He took a deep breath and studied the picture, “I may or may not have a niece and nephew…”

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

“He’s gone, I think.”

I roll over to look at her. “Who’s gone, babe?” I asked.

“The guy that’s been tailing you,” she answered as she rolled over to face me, “I noticed that he hasn’t been by in a couple of days.”

“Babe, you’re a bit paranoid,” I laughed, “I’m not being followed or anything.”

She sat up and took the pair of glasses from the bedside table and fixated it on her beautiful face, “look, I can clearly tell you that you were being followed. Whoever it is got the information they wanted, so they’re gone!”

“Alright, alright, I’m being followed, and the government is going to come and assassinate me. Babe, you still didn’t answer my question: Do you think I should sleep with Margaret tomorrow or not?”

She took a deep breath, “Well, you’re pretty much free tomorrow, as long as I get some afterwards.”

“Eve, you know you always get one afterwards.”

She smiled as she leans in close and we shared another kiss, “that’s my bull.”

When I got to this town five years ago, I didn’t think my life would end up like this. I don’t work, I don’t need to now, and the only “work” I do is pretty simple: I have sex with women for money, and my girlfriend is my pimp.

It’s not dirty or anything, illegal it might be sure, but the women I sleep with are all tested regularly, and I am too. Sometimes I go to their home or sometimes I go to the apartment. I still have standards, though, no women over 45, I have to find them attractive, they have to be fit, and they have to be on some sort of birth control because I refuse to wear a condom.

Although there are a couple girls that I’ve impregnated, for a few thousands more. In these cases, I’m not on the hook for child support nor do I get a say in how they are raised. I do see them from time to time, and their mothers are still a client of mine. Besides the ones Eve has, I have two more kids from two different women.

All of the women I sleep with are rich, bored housewife whose husbands are already cheating on them and they have either an open marriage or an agreement. I do have a couple of girls who are single and just wanted to have sex. Having said that, the mothers of my children are someone who I don’t charge money for. Once a week I go over and have sex with one of them and I alternate between the two.

All in all, I have about 20 girls that I regularly have sex with, and I earn about 8-10K a month.

But Eve, she’s a special girl. She’s the first girl I met, and we strike up a relationship almost as soon as I got here. It was her idea to pimp me out to these housewives, but she’s the one I always come home to.

“How much is Margaret paying again?”

“Her usual of $1000,” she answered she sank back under the cover, “she wants the entire package: Kissing, blowjob, oral, vaginal penetration, she’s even forking up an extra $200 for anal.”

“Anal? Haven’t done that in a while. Did she say if she’s clean back there?” I asked and she kind of grunts at me.

“She said she’s been wearing a plug since Monday, and she did some cleansing today. Just show up around 10 AM and give her a good dicking, then I’ll come and pick you up for lunch,” she mumbled.

“Well if we’re having lunch, we gotta take the kids somewhere they like to eat,” I pointed out and she rolled to her back.

“Maybe that pizza place again? I’m starting to hate pizza if I’m being honest,” she grumbled annoyingly, “I guess somewhere that serves fries?”

“Sounds good. Alright, 10 AM over at Margaret’s then. Love ya, babe,” I said, and we kissed again, this time lasting about a minute or so.

“Mmm, you’re such a good kisser. No wonder the girls pay extra just for you to kiss them.”

Wow, I didn’t know the girls were paying extra just to get a kiss from me.

“Are the kids alright?” I asked and she laughed lightly, “I’m being serious here.”

“Sorry, sorry, yeah they’re fine. As long as mommy and daddy are happy, they’re happy. But Chris, how long do you think you can do this? I mean, the money’s good but I don’t see us doing this forever.”

How long indeed… “well, let’s build a good nest egg before we start thinking about the future. I can go back to school, go for that computer science or computer engineer I’ve been wanting for a while now.”

“Oh yeah? You’ve always been good with computer, hun. I need some shut-eye, I got a shift tomorrow. Your car should be good, and that knocking in the engine is gone.”

“Thanks, babe,” I said as I lean over her and kissed her again, “I like cars, but I’m no good with them.”

“Oh, by the way hun, you know how Margaret likes it right?”

===

[Margaret](https://m.media-amazon.com/images/M/MV5BODk5NzY5YTEtMGMyMS00NTc4LTlhZTctYTYwNzk0YzgzYTc1XkEyXkFqcGdeQXVyMTE5ODM2NjEy._V1_.jpg) is probably my youngest customer, at 19. Her parents are rich, and they live somewhere else for work managing some company, and so she’s basically surrounded by servants and butlers, like those rich kids you see on movies and television. She’s very pretty, blonde and white, and she’s very uptight and crass with how she treats others. She goes through maids and butlers because she’s such a brat and she doesn’t seem to know how to talk to others. I’ve slept with her probably about 15 times, and it started as soon as she turned 18. Her parents got wind of my “services” from one of their friend’s daughters, one of my customers, and they thought it was a good idea to introduce their child to sex.

How that’s a healthy way to go about it, I have no idea. I probably ruined her for other guys, but that’s not my place to do. It was supposed to be a one-time thing and she’s supposed to get a boyfriend since, but just like a lot of things in her life she doesn’t put a lot of effort into it. If she doesn’t have a lot going for her during the month, she calls up Eve and pays for my time. There are times where a month or two she’s really busy about something and we don’t hear from her, but when she does and I go to her, she is extremely, extremely horny.

“There you are, you’re late! I said be here by 10 AM and it’s already 5 after!”

She has a nice voice, a very cultured English accent, but while she has the accent the words she uses are American through and through. But the way she talks is brash and devoid of thought behind it. She leads me into the house, and I noticed that it’s empty.

“Oh, I gave the help the day off. They’re pretty happy about that,” she said with a wave of her well-manicured hands, “we should be good.”

I’ve said before how Margaret is beautiful. She’s a total 10, the full package, nice perky breast, a tight D I think, smooth fair skin that’s blemish free, she stands at a reasonable 5’6, and she has a nice ass. Her long, blonde hair curls at the end, and she’s got a shine on it. Right now she’s wearing one of those white cocktail dress with matching heels.

She likes to walk up front and as soon as we get into the kitchen, I closed in on her and grabbed her by the back of her neck. “Ooh, we’re going to start? Don’t make a lot of mess, the help won’t be back until tomorrow.”

I looked at her, regarded her fully as I tilt her head back. She really is a beautiful girl; she just needs to be a little bit more aware of how others feel. I can understand why she’s been single all this time but having me screw her whenever she feels the need is not healthy for her. She’s young but I feel like she’s the type to keep thinking she’s going to stay young forever.

I started kissing her neck softly and lightly, making my way up to her chin. She laughed and giggled at my effort while her hand went for my belt. “No, no, no. You know how it goes,” I told her while my hand grabbed hers and lifts them up over her head. She smiled precociously as I pushed her against the counter. “We can’t go to the good part just yet, stop being naughty.”

So, we started to kiss. Truth be told, I wasn’t much of a kisser when I got here. When Eve and I started going out I hadn’t kissed anyone. She was my first – she was my first in every sexual experience. She’s the first girl I slept with, she was the first girl that I gave oral to, and she coached me on it, the first girl who gave me a blowjob, and the first girl that I had anal sex with. She taught me what I know, the basics of it, and the rest I either researched or I experimented with.

I pulled her in tighter to my lips and we danced and fought over who’s going to be the dominant one on this. She’s been doing that ever since we started, trying to establish herself as above me, but every time I win over her and she has to submit to me, and today isn’t any different.

She tried to push against me but I pulled her back by the back of her neck. “Oh no, we’re playing by my rules right now,” I snarled against her cheeks as she laughed. We pushed away from the counter and I spun her around and pulled her against me, then my hand went south and under her little dress. She moaned loudly as my finger touched her bare, uncovered pussy, and she yelped with surprise as I fingered her a little bit and then brought my sopping wet hand up so we can both look at what she produced.

“Already wet? We haven’t even started,” I snickered lightly. She moaned softly while my other hand squeezed and pinched her erect nipples. “And no panties too? You know my rule, and you broke it.”

“Oh no, I broke a rule? What are you going to do to me?” Her tone is a naughty and teasing. I know how she likes it. I know what she likes.

I grabbed her by the hair and pulled at it, bringing her chin pointing up. “Get on your knees and you’re going to crawl back to your room and you’re going to put on some panties like I’ve wanted you to.”

I pushed her down to her knees, keeping her long hair in my palm, and I walked her back to her room. She crawled on all fours, whining like a bitch in heat, and I spanked her add every time she lagged behind. “Almost there, come on,” I said to her and she whined again. When she lagged behind again, I pulled on her hair a little bit.

“Come on, go up the stairs. You know where your room is, why am I leading you?”

I made her crawl up the stairs and I just watched her cute little butt sway side to side. I spied the little jewel hidden inside her ass and I spanked her again and again just to get her to move faster. “Margie, get your ass up there!” I growled at her as I give her plump ass another big slap. She moaned and yelled out in both pleasure and pain and she soldiered on.

We finally made it to her room and she crawled to her dresser where she stood and opened a drawer. Her room is nice and well maintained, props to the maid for that, and it’s nothing special if I’m being honest. Her drawer has her panties and thong in a nice little order. She looked at me and swayed her hips from side to side as I picked out what she’s gong to wear.

“This one,” I said as I held up a nice little black, lacy thong. She gave me a nod as I bent down and held the legs open for her which she stepped in. When it’s on her, I lead her to the bed and pushed her down to her back. “How many times do I have to tell you to wear your panties when I come over?”

She just smiled mischievously. This is one of the little games she and I play, and this isn’t the first time I made her crawl up to her room on all fours. I just groaned in frustration as I started rubbing her pussy. She moaned a bit, hissed and gave little grunts, and when I slid her panties aside I just marveled at how wet and ready she is. I slowly licked her pussy and her head shot back against the mattress as she moaned in pleasure.

“Hoooo yes! Keep going daddy, keep going!”

I licked up all the fluids she’s been gushing out. I spread her lips a little more and stuck a finger in while my lips went around her clit. I sucked on tongue-slapped that little pink button and she moaned hard and loud. Then my hand went to her little plug and I twisted and pushed and pulled it in while keeping it inside her tight little asshole, all the while sucking on her little clit.

“Oh god! Oh fuck, keep going! Keep going! Oh shit, I’m cumming! I’m cumming! Don’t stop, don’t you fucking stop!”

Her back arched and she let out a faint scream

“Y-You’re always on point,” she sighed as soon as she got off the orgasm train, “now come and fuck my pussy.”

“No, we move at my liking,” I told her as I spun her around so that her head is hanging off from the edge of the bed. I started taking off my belt and then my jeans while her hand went and touched me all over. When I got my cock out, it fell and thump her on the chin. “Hands off,” I said and her hands immediately went to her crotch, fingering and rubbing her clit slowly.

I grabbed the back of her head and brought her to level, “open up,” I told her and she slowly opened her mouth for me. She had a somewhat smaller mouth.

“It’s so big,” she gasped, “have you measured it!?”

“Almost 10 inches, and a little over 6 inches in girth,” I answered and before she could even say anything I slid it in, “shut up and do what you’re good for!”

I roughly thrust myself in and out of her little mouth. I didn’t go balls deep, no she’s not ready for that yet. I keep telling her that if she wants me to roughly fuck her face, like how she’s been wanting me to, then she needs to train herself for it. But every time we go and get hot and heavy, she can barely go to the middle of my dick.

“You bought some dildos to practice with, right?” I grunted while my dick is mid-deep down her throat. “Answer me, did you or did you not?” I kept myself down there a few seconds longer than what I intended to, and as soon as I relented she took a great, big breath.

“I-I did,” she answered shortly, “but it’s boring without your hands grabbing my throat.”

I shoved myself down her mouth again, going deeper and deeper until she gagged and coughed, spit oozing out from her nose. “You need to practice,” I grunt again, “practice makes perfect!”

I bounced myself on her throat and stayed a little longer, and when I came off again she took another deep breath. Her mouth and throat is warm and wet, she felt good twitching around my cock as she did her best trying to swallow me.

“I can’t get enough of this cock! No one else can compare!” She moaned as her hand wrapped around my cock and brought it close to her again. She sucked on the head while her hands stroked me, and she felt so good that I honestly wanted to cum in her mouth. “Cum inside my mouth! I want to taste it!”

“If I do then we’re done,” I groaned, “you only paid for one nut from me.”

“I don’t care, I’ll pay for another one, just please I want your cum inside my mouth!”

I picked up my pants and fished my phone out from my pocket. I got Eve and called her up. “Hey, she wants another shot. Yup. Yup. Alright, just come pick me up in about an hour and a half. Alright, I love you, I’ll see you in a bit.”

I slid the phone back into my pocket. “That’s an extra 200,” I said and she just moaned loudly.

So I kept thrusting and thrusting into her mouth, grabbing her throat and lightly choking her. Her fingers went back to her pussy and clit and she fingered herself until she climaxed again. Watching her cum is honestly pretty damn hot, and frankly it got me wanting to reach my own.

“Tighten your lips,” I said and her mouth tightened around me. I continued fucking her face until I finally shoved it deep and came down her throat.

I sent strings and ropes of hot cum barreling down her throat, and when I drew back I deposited some into her mouth only for me to shove it down her throat again. I kept going and going, throwing more and more pearls down into her mouth and throat, groaning and moaning each time. I watched her back arch again and she squealed and whined and her mouth squeezed me tightly.

I emerged from her mouth breathing and gasping slightly, giving her tits a good squeeze. “Good girl,” I said as my cock left a trail of cum hanging from her lips, “that’s a good girl.”

“She rights herself up, wiping her lips and sucking at her finger tips. “Fuck, that was so good daddy,” she mewled as she spreads her leg and pumped her fingers into her wet, sloppy pussy. “You tasted so good. That $200 is so worth it.”

“Good, good. I like a satisfied customer.”

She bit her lip then started sucking her digits again while I regained my breath. “Ready?” I asked aloud and she eagerly nodded.

I pushed her to her back and pulled the top part of her dress down and pushed the bottom hem of her dress up and bunched it on her waist. I went straight for her beautiful big tits while I rubbed my cockhead against her nice, pink slit.

“Yes! Fuck me, daddy, fuck me!”

“You still want anal?” I asked and she nodded, “well, where do you want me to cum?”

“Inside my ass, please daddy,” she whimpered, “but I want a good fucking in my pussy.”

“That’s only for good girls,” I growled at her, “have you been a good girl?”

“Yes, daddy, I’ve been a good girl,” she whispered against me. I hadn’t put it in yet but I would press it in slightly and pull it away.

“Have you? Have you, really? You’re being nice to your staff?”

She nodded.

“You’ve been respectful to them? Have you been yelling at them like you used to?”

She nodded, but shook her head on the last part.

“Good,” I said and pushed my cock into her. She gasped and her eyes widened, “you get a nice gift from me.”

“Oh! Oh god! Oh my god, it’s so big! You’re spreading my poor pussy!”

I started slowly. I started by pushing until I get to the middle of my dick and then pulling back. I did this until she’s nice and ready for me. She moaned loudly and clawed at my back while I sucked her beautiful tits.

“Keep going! Keep going! Oh you’re going to make me cum! You’re going to make me cum again, daddy!”

I felt her pussy twitch and spasm, hugging me tightly whenever I pulled back and accepting me so readily while I pushed in. “You’re so tight,” I snarled at her, “your pussy is so nice and wet too.”

“This pussy loves that dick, daddy! Make me cum again, make this pussy cum for you again, daddy!”

I pushed the entirety of my manhood in and her back arched and she squirmed and gasped as she came again. I felt it, I felt her pussy contract and squeeze me so tightly that I was afraid I’m going to bust a nut right in her tight, little pussy.

So when her back settled I released myself from her convulsing slit. I reached down and felt for the jeweled end of her butt plug and slowly released it from her trap.

“Please, please daddy. Please, please be gentle.”

“Since you’ve been a good girl, I’ll be gentle,” I said as I reached up and pulled her in for a kiss. I hadn’t forgotten about that and I made sure I gave her some tongue action too. She moaned and pulled me in tightly, I’m guessing she hasn’t had a successful date yet that’s why she called for me. I told her to go on dates and find a boyfriend.

“Boy troubles?” I asked and she smiled.

“They’re so immature right now it’s not even funny. All they want is a one night stand, or for me to send them nudes and sexting. I haven’t found any good, quality men yet daddy, not like you.”

“Well don’t stop. I can’t be your boyfriend, but I’ll be your daddy.”

With that I rubbed my cock against her little brown button. She curled her legs to her side and looked down while I slowly teased her little asshole.

“Yes! Yes, daddy, please put it in. I need it, I want it so bad daddy, please, please, please!”

I spat on my hand and rubbed it all over my head then I pressed it in firmly until it broke through the little brown eye. She moaned and gently squealed and gripped my forearms so tight.

She hissed and huffed as she looked down and watched me advance. I did it slowly so she can get used to me. I would push in slowly, stop for a few seconds, pull back out and then repeat. I kept doing this and pushing in more and more

“Go on, fuck me deeper,” she softly moaned. She swallowed hard as I went deeper until I got about midway. “Ok… ok that’s it. Don’t go too much, daddy, I want the rest for next time.”

“Next time? You’re such a naughty girl,” I coyly said and she winked at me and grinned.

“Mmmm, now fuck me daddy. Fuck me like the whore that I am.”

I pull back and thrust into her and she damn near screamed. I did it a couple more times, with her screaming and shouting my name.

“Fuck! Fuck me, Chris! Fuck that ass, push that shit in! I’m cumming! I’m cumming from my ass! I’m cumming from a big dick fucking my asshole!”

I kissed her again while thrusting into her faster and faster. She bit my lip softly and nibbled at it. “Fuck, you’re a good fucker, Chris. Why don’t you leave your girlfriend for me? What do you say?”

“You know I can’t do that,” I groaned, “and you know my rules. I’ll pretend I didn’t hear you say that, but if you say that again I’ll have to blacklist you.”

“Oooh… okay, okay daddy. As long as I get my pussy stuffed with this hard cock, I’ll be happy.”

I leaned in again and took her tit into my mouth. I sucked and bit at it, leaving my calling card for her. “Promise me you’ll find a man, that’s all. I’d hate to lose you as a customer.”

“Okay, daddy. I’ll keep looking, but promise me you’ll fuck me whenever I want?”

“You got it darling.”

I lift her leg up until they’re framing her face. I kept digging down her asshole, making sure not to go all the way. She looked at it while squeezing, moaning and hissing.

“Fuck, fuck, fuck! I’m cunning again! I’m cumming again! I fucking love sex!”

I leaned down an covered her body with mine as my thrust started to go faster and faster. With a big groan, I released my second load into her gaping asshole. I felt her brown ring squeeze me, then I felt a warm wetness exploded up against my pelvis. Did she just squirt? She just squirted!

I looked over and she’s laying there with her mouth wide open and her eyes rolled to the back of her head. She’s holding her breath as another orgasm rocked her body. When she finally took a deep breath she let out a bowl that echoed throughout her room.

“I came again! I came again, Chris! Holy fuck that was so good! Oh god, that was really fucking good!”

“Glad you liked it,” I groaned as I detached myself from her. I slowly shambled myself to her restroom and got a small towel and wiped my cock and my pelvis off from her juices. “Margie, you’re alright?”

“I’ll… I’ll be fine… oh god I’m still c-c-cumming,” came her stuttered words, “y-your money is in my bedside table, in an envelope. It’s a-all that, even the extra 200.”

I opened the dresser and she crawled up to me and went across my lap and sucked my cock. “You’re a good little slut aren’t you,” I said as I rubbed her head, pushing her lower until she gagged, “good girl,” I said and she just smiled at me.

I counted the bills in the envelope. Yup, $1200 and it’s all there. She probably wanted for me to cum in her mouth anyway and banked ok that fact. “You’re a really good girl,” I said as I bopped her forehead with the envelop. I picked up my pants and slid it on and took my wet shirt off. I got my phone out and texted for Eve to come and pick me up.

“Next week again?” She sighed.

“Take it up with Eve. You know how it is, Margie.”

“Okay, daddy,” she smiled as she dipped her finger in the pool of warm cum. She gathered up as much of her butt nut and poured it into her mouth, “you taste so good daddy,” she cooed as she sucked on her digits.

“Alright, I gotta go Margie.”

I got up and walked out slowly since my legs felt a little softer. I had to hold onto the walls a bit.

“Was my pussy that good daddy?” I heard a giggle from behind.

“Margie, shut up. You know you’re 10/10,” I laughed and she blew me a kiss.

By the time I got out of the house, Eva was already waiting for me and with the kids too. I waved at them, smiling, and they waved back at me. I got into the passenger seat and gave Eve a kiss.

“How was it?” She asked with a gentle smile, “good?”

“She’s good, not as good as you but she’s good.”

“That’s my bill,” she smiled again as she kissed me on the cheeks. I handed her the envelope and she opened it and counted the bills. “There’s an extra $100 here,” she said with surprise.

“Must be a tip then?” I laughed, “well that’s for dinner then. Did you decide where to go?”

“Chili’s,” she answered and I smiled, “I know you like Chilis.”

“Babe, I like wherever you and the kids eat. Come on, I’m both starving and thirsty.”

We drove off. I looked at the side mirror and noticed a black sedan pull off at the same time we did.

“You noticed too?” She asked, “told you they got the information they needed.”

“No, you’re just being paranoid. Let’s just go and eat, alright babe.”

Deep down, I kind of know who’s behind it all. I just wish they’re decent enough to leave me alone.

~ End of Chapter 1 ~

Source: reddit.com/r/eroticliterature/comments/rznzqm/what_if_jackie_showed_up_after_graduation_mf