“She’s Cheating With Her Friend’s Dad” [mf] [anal] [long]

EDIT: [Includes ATM]

“She’s Cheating With Her Friend’s Dad”
“I’m 18, and a senior at a parochial high school. I have a boyfriend. We’ve been with each other since I was 15. I actually lost my virginity to him. He is a year older than me. He graduated last year from public school. I love him so much. He’s always been good to me. He likes my friends, and I like his. I friended a new girl at our school. She was from out of state. I kinda felt bad for her. I just figured it would be so hard for me to leave the kids that I grew up with only one year left before I’d graduate. I’m sure she felt like that, and that would be terrible….Her name is Jessie.

Jessie, her mom, and stepdad moved to our town when he picked up a new job in our area. I started to really spend time with her, mostly at her house. I have a younger brother that would be so annoying with his pubescent testosterone pumping through his body. I definitely didn’t want to do that to her. She is drop dead gorgeous too. From what I could gather, her family seemed really down-to-earth. When her stepdad was around, and not her mother, he was always real talkative, and seemed so knowledgeable about pretty much anything. He was also very funny. I don’t know what happened to Jessie’s real dad, but, she certainly got lucky with her stepdad. Like I’ve said, her Mom and step Dad seemed very nice.

My boyfriend, Aaron, loved the fact I hung out with Jessie. He liked me being with her, at her house, because, that means I wasn’t out talking to other guys. Aaron was a very jealous guy, and somewhat, controlling. But, I love him. I thought before that we’d marry someday. He was my man, and I was his girl. If I wasn’t with Aaron, I was with Jessie.

The more I went over to my girlfriend’s house, the more I talked to her step-dad. He was really smart and polite. I never really saw him kiss, or joke around with Jessie’s mom. They sorta did their own thing. He would sit out on the porch and watch tv and drink a few beers, while his wife was either out with her new girlfriends or in the living room watching “Housewives of whatever city”. I could tell he had so much love to give, but, no one to give it to. Last week I stopped over their house when I knew, Jessie, his step daughter, wasn’t going to be home. I really started liking her stepdad, Michael. But, not just liking him as Jessie’s stepdad. I started to want him, as the man, the more we talked. I thought it was an impossibility. Which made it so right to be thinking such naughty things. It was becoming my fantasy. Something, I thought, would never come to fruition.

Michael was 42 years old, and is pretty hot. That day I stopped over, my boyfriend kept calling. I answered once and told him I was at the mall with Jessie and her family. Well, I WAS with her step dad, so, I wasn’t lying entirely.

I went over there using the excuse that I needed notes from class for a test we would be having the next day. I think Michael knew why I was really there. I just wanted to be near him. This man was rocking my world, in my mind, and I knew where it was inevitably going. Or, so I hoped. The way he discussed love and the importance of self sacrifice in a relationship was getting me so turned on.

I knew Jessie would be back soon, so I had to get going. There I stood in his kitchen, getting ready to leave, with Michael standing right in front of me. I don’t know what came over me, but I just kissed him. He kissed me back. He kissed me like he’s been wanting to do that, to someone, for a very long time. He had me. I was in his control. If he would of wanted to fuck me, right there and then, I would of dropped my panties beneath my pleated school skirt, and got on top of him and rode him like he hasn’t felt in a long while.

He had his 42 year old tongue down my throat, as he held my face in his hands. He moved those hands through my blonde hair, putting it behind my ears, down the back of my neck, over to my shoulders, working down my arms, and around my waist. He then moved them down my hips, to almost mid-thigh, and then back up under my skirt to my butt. He began squeezing my tight 18 year old ass, through my panties. Mmmm. This older man was making this younger girl so wet. My boyfriend hasn’t gotten me that wet, that fast.

I couldn’t believe what was happening. Michael moved his fingers underneath the bottom of my panties, spreading my ass with his index fingers, and with his middle fingers of both his hands, he felt my wet vagina with those two long fingers. He then came up and spread the very bottom of my ass again, the same way, with his slick fingers, started to do small circles on the center of my young, virgin, asshole. Mmm. It felt so good. I thought, I hope he starts fucking me. He pressed just the tip of his finger partially in that tender indent. Oh, I wanted Michael so bad. I bet he was so good. I wanted him. I wanted my girlfriend’s step Dad.

Before we could get any further, we heard the living room door open. It was Jessie. Oh shit! Two hours went by so fast. Michael had a hard on. He sat down at the table and said, “See, I told you she’d be home soon. Was I not right?” Michael saying that made it look like I just walked in the door. Even though my panties were soaking wet and my clit, throbbing. I just asked Jessie if she had her bio notes for the test we were having. Close call.

I was so worked up thinking about Jessie’s stepdad, and how he got me so wet, I couldn’t help but masturbate, finger my pussy, and rub my clit as soon as I got home. Oh, I wanted this man. As I said, I love my boyfriend, but, there was something about Jessie’s stepdad. I’m sure he could take me there. I’ve never orgasmed before with my boyfriend. We were close a lot of times, but he always finished before I got there.

All week, I was getting texts from Michael. I smiled every time I heard that familiar ring tone. He actually got me to do things I would’ve never done with my boyfriend while I was at school. He got me to go pantyless, at school, with nothing on but my school skirt. I even lifted my skirt and took a picture of my cooch with my phone under my desk. I even went in the bathroom and lifted my skirt, and did my best to capture the ass that I would, so willing, give to him. (See, ‘this’ girl sends pics of her ass….hello, I’m right here?)….I was so horny for this man. I wanted him to do anything he wanted to me. Him, 42. Me 18. Twenty-four years apart. I wanted him to touch this young ass again. My ass needs loving. If my boyfriend ever would have brought anal sex up, I’m positive I would of done it. Knowing him, the way I do, I never did bring it up, thinking he’d say, “that’s disgusting”, or, “that’s an exit only” or something like that. I think I’d actually finally have an orgasm from doing anal. Mmmm. So frustrating. I’ve left him so many subtle hints before, but, he never figured it out, or went there, like I thought.

Aaron and I went for a walk later in the evening. We were holding hands as we walked closer to Jessie’s house. My boyfriend didn’t know it, but, I did. Michael was outside washing his 80’s conversion van.
Michael actually had a couple vintage vehicles. My favorite was that van. It was all redone, complete with the checker board table and shag carpet on the walls. Jessie told me about it, but, I’d love to see it for myself. Michael caught Aaron looking in his direction and waved. My bf waved back and yelled up the drive way, “Nice van!” Michael just nodded and smiled. Oh, gees, not in a million years would I have thought my boyfriend would speak to the one man who was constantly on my mind, and he had no idea. He had no idea even who he was. I just waved also, being friendly, pretending like he was just a stranger, and I was simply being friendly. Whew. That could of been really awkward.

Seeing Michael, and thinking about him touching me, got me really horny. I seduced Aaron to give me sex. I could not help but think it was Michael entering me. It certainly made the sex better for me. I got so close to asking Aaron to give me anal. So close. While we were fucking I kinda felt bad that I was doing all of this stuff behind his back. Having these naughty thoughts about an older man. He didn’t have a clue. Just the thought of my boyfriend’s cock being Michael’s, I almost was reaching a climax, until my boyfriend pulled out of my pussy and came all over my belly. I was feeling bad for not giving my boyfriend his own attention. He has been good to me, and I have not done anything “really” wrong yet. Except just a little kiss, on my part. I mean I have kissed his older brother on the cheek at Christmas and stuff. So, what I did, was no where near cheating. My hands didn’t touch anything. It was only like a minute, compared to the three years, which was well over one and a half million minutes that were all Aaron’s. A few minutes, compared to all of those, was really no comparison. That’s how I justified it. I wasn’t going to worry about it anymore, even though it did consume so much of my thoughts.

I just couldn’t get Michael out of my head. He knew how to make a women cum. I just knew it. He probably could do it just with those thick fingers of his..He gets me so wet. I am sinfully attracted to a man that literally could be my father. So hot. I’d love to have that cock deep inside me. That used cock. That cock that has probably been up so many asses in his life. Maybe even got it dirty on occasion. Oh, I wanted him to secretly fuck me in my bum. So bad.

It was finally Friday. The stars must of aligned the night before, in just the right order for me. Jessie asked if I could sleep over. Since I just gave my boyfriend his five minutes of sex two nights ago, this was not going to be a problem. I went back and forth with scenarios in my mind and what I would do if Michael, somehow, got me alone. I wasn’t sure what I’d do. I wouldn’t know how I’d feel afterwards, concerning my boyfriend. Ok, if something DID happen, it’s not like Michael is a threat. He’s not another boy in my class. Michael is married. It’s not like we could be an item, or anything. This kinda bummed me out, in a way. I was actually feeling jealousy for a married man. It’s amazing how one minute can change your whole outlook on things. A minute like that brings out the naughtiness that’s always been hiding in you. Even though, two months ago, even I thought I was a goody-goody. Now, I’m so secretive within myself, and constantly soaking wet…

I really didn’t have time to shower or change, so if anything would happen with Michael, I didn’t want him to go down on me. I was worried my smell would be a little “off” and I didn’t want him to think I wasn’t clean. I did have gym that day also. So, this would be a big “No”. Just fucking, that’s it. No kissing either. I also wouldn’t look at him, or his cock…. Listen to me. Gees. I know me. I’d let him do whatever he wanted. I wanted him to finish what he started in the kitchen. I hope he’s not acting weird about it. Because if he is, then I’d have to act weird also. I wanted him to know that he has consumed my mind all week, and how bad I wanted him. How bad I wanted him to treat me like he pleasured his previous lovers in the past. I wanted that middle aged man to make me feel like a woman for the first time in my life. I know, even with our little “thing” that happened earlier in the week, in the kitchen, I might be building myself up for something that might not even happen.

When I arrived at Jessie’s house, it was around six o’clock. I had to take my brother somewhere after school and I finally just dropped him off. I called my boyfriend on the way over to tell him I love him. I felt so naughty, for the thoughts I have been having. I rang the bell and Michael answered. I had butterflies in my stomach immediately. I should of known better, to think that he might act weird around me. I should of known. He’s not 18. He’s a man. He didn’t make me feel weird at all. Actually he made me relax, simply by being a gentleman.

Michael said, “Jess and Patty will be back in a half hour or so. She told me to tell you to wait here, she needed to get her mom to go with her to get new shoes or something, who knows…Would you like to come in?” My face, I think told Michael everything he needed to know. I just stood there like an idiot. “Hey, do you want to have a look at my van. I’ll show you what comfort was like in the 80’s”. I just nodded.

Walking over, Michael still was the only one talking. I just wanted to tell him. “Please, fuck me now.” The man is so hot. I don’t know what it is, but, my pussy was getting wet again under my skirt. “My Dad had one of these when I was a kid.” He said, opening the side door and sticking out his hand to let me know I could get in. “Oh, Thanks.” I finally said, ducking my head and stepping up. “Wow, it looks so comfortable in here.” I said turning around just as Michael shut the door behind him. “I’ve been thinking of you all week my dear.” Michael calmly said, gently putting his hands almost completely around my arms, staring down at me. I looked up into his weathered eyes, and said, “I’ve been thinking about you too.” I sheepishly told him in return. Then, Michael put his fingers on my chin, and bent his neck down to give me a perfect open mouthed kiss. I was instantly in heaven.

You could hear how our kissing picked up, and the rustling of clothes as arms were moving everywhere. We moved our way over to the cushioned bench that ran along the opposite side of the doors we just entered. I sat down. Michael kept kissing me when he ran his left hand down my side and under my perky breast, just to cup it and make out it’s size I guess. He continued down the side of my stomach, past my hip, on the outside of my school girl skirt, and on to my bare thigh. “Mmmm” I said, feeling his warm, calloused hand start to move under my skirt. I instinctively opened my legs, as he guided his hand to my panty line, and ran his finger on the inside, using the outside of his fingernail to graze over my short trimmed landing strip. I could not believe how worked up this man was making me. My panties were soaked.

I took my hands and pulled down my panties, and he helped me get my leg through one leg hole. I lifted my legs in the air. Michael paused kissing me, when he went down on me. I jerked, thinking, I didn’t want him too, but once he got there he softly said, “I love the way you smell.” That turned me on so bad.

He put his whole mouth on me and completely covered my entire pussy. I could feel the warmth of his breath as he began to do amazing things with his tongue. He was moving so fast. He was driving me nuts. “Oh, Jesus..”, is all that I could say. Michael certainly knew what he was doing. This man was more than twice my age, by six years, and I wanted him more than I have ever wanted someone before in my life.

He lifted my ankles up as he continued to suck on my clit, driving me mad with lust. I shimmied my way out further on the bench. He had complete access to ‘everything’. He licked his way down and, Oh, God, he circled his tongue around my sensitive bumhole. The feeling going throughout my body was incredible. His soft tongue found its way to the very edge of my anus. Teasing me. Arousing me. Circling my asshole with his tongue, purposely staying fractions of an inch away from sending sensations throughout my body. I grabbed Michaels head as he was able to make eye contact with me. So fucking turned on. I showered in the morning, went through a whole school day, including gym class, and here was this 42 year-old man, about to enter his freaking tongue in this 18 year-olds sweaty, tacky back door. Almost the definition of taboo. I felt so dirty. I felt so slutty. I felt so sneaky..I felt like a woman…I was cheating on my boyfriend, and he was NEVER going to find out about it, no matter what. I felt the feeling that only certain women ever dared to go, and I was still in school.

Enough of the teasing, Michael’s tongue finally entered my ass. For the love of all things good, that feeling is indescribable. How do you describe something, you may have never felt, entering your butthole?..Orgasmic, is all that I can say. Without even realizing it, my hand moved down onto my clit. My pussy was dripping down into my asshole, which ended up on Michael’s tongue going all around the inside of my rectum. I could feel my rectal muscle fighting his tongue. Michael was clearly winning that battle.

At this point, My knees were up by my shoulders, While Michael’s big hands cupped my ass cheeks, spreading my anus with the inside of his thumbs. He was going clockwise, as deep as he could go with the thick part of his tongue, and then he’d reverse his direction, sending waves of pleasure generating from my rim and flowering throughout my body. I had to close my eyes, while I rubbed my clit, and I pushed my ass into Michael’s face, in rhythm as if he was actually fucking my rear exit.

Rubbing feverishly, I was causing a wet spot growing under me, onto the velvet bench cushion. “Oh, god”, I barely was able to say. This 42 year old hunk, had this barely legal teen’s ankles up in the air, while he continued sticking his beautiful long tongue inside my asshole. Spinning it, opening me up, swirling the edges of my sphincter muscles. Oh, lord, the feeling!

The sound of a sloppy mess stopped when Michael came up from my pussy juice infested asshole. His face was all shiny. I grabbed the back of his head with my soaking wet hand and brought him up to stick my tongue down HIS throat. “I want you to fill up my ass with your big cock.” I got out, in between our tongue wrestling.

The thought of that same tongue being in my now, cleaned out asshole, just made me suck on his tongue even more. My sweaty ass tasted fantastic. It felt so dirty, but it was such a huge fucking turn-on. Holy shit I wanted his cock inside there, now.

Michael’s cock was wide, and that got me even wetter knowing that thing was going to stretch me out. I needed it so bad. I needed fucked in my ass. At this point he had both my ankles in one hand as he lifted my ass up a little more to get full penetration with his cock.

Then it happened. I felt his warm, wet, pre-cummed tip touch my inner anus, without penetration. The inside of my ass was visible due to the position I was in. Fuck. Michael started it in. Biting my lower lip, I begged my ass to accept it. The pressure was intense. I wouldn’t say it was pain. I wanted it so bad, it was orgasmic.

I had each of my hands stretching out my ass, with both my middle fingers right on his shaft, feeling it go in me, slowly. I was breathing real fast like I was in a Lamaze class. My left eyelid was flickering. Then, there it was, with my fingers I felt his balls rub up against them. Michael was all the way in. I had such a deep feeling of absolute sluttiness in my mind, and I loved it. I started rubbing my clit, making my assfucking feel that much better.

I’ve only been with one other guy in my life, and that one guy is NEVER going to find this out, ever. This was going to be Michael and my little secret. If it remains like that, I’ll do this even if I marry Aaron. I’ll even send him pics of me with different things up my ass (Be like this girl, ladies, send those nudes to those guys that want you to ?, like me for example). “Oh, shit, Michael!” I let out, as he began to back out. I could feel my rim pulling out along with his cock. Such a tight fit. But, it did fit. Michael was moaning while gritting his teeth. It felt so climatic leaving my ass, I came while rubbing my clit at light speed.

Back in he went. My asshole was spasming, with no direction, or space to spasm. But, I could feel it. I touched my rim as it did a full reversal back into me. Michael was going in and out a little faster to keep a good pace. I could be more vocal now that he has loosened my forbidden hole up. It was amazing. My clit was swollen, my body was shaking. The head rush from my orgasm, was bringing my vision back. “Mmmm, yes, Mr. Peterson, how does this school girl’s ass feel? Tight? Mmmm. You’re amazing with that cock…” I said, now holding the back of my thighs, with my knees at my head, while he pummeled my ass.

I had my eyes closed, enjoying Michael (Mr. Peterson) injecting his whole length in me, I could feel yet another assgasm building, when out of no where, the van door opened!….My eyes widened, my heart rate went up. Michael just looked over without stopping his penetration. Even if I wanted to move, I couldn’t. I was being pinned further and further into the side of the plush maroon carpet of the van. It was Jessie! Shit! “Umm, Jessie!…” I said, quickly, trying to come up with an excuse. “You guys, the whole van is shaking… I thought you’d be done by now, …Daddy…”
What? I thought. Michael just shook his head, trying not to lose concentration. “You’re lucky Mom went up to pee… I thought I gave you more than enough time.” Jessie said, smiling at me. I relaxed again. Well, the best I could at the moment. I was somewhat confused. “Well, I’m going to help you guys finish. I’m glad I’m here for this.” Jessie said, leaning down and kissing me ever so gingerly. I have never kissed a girl before, but, I liked it.

Michael was jamming my ass really fast. Jessie went down and started licking my clit. “Shit, oh fucking christ. Shit. I love you guys..” I said. I really felt good. I was cheating so bad on Aaron, and I didn’t care… Jessie was speed bagging my sensitive clit, and playing with Michael’s balls, when he started to moan louder as he thrust into my ass even harder. He was ready to cum. “Explode in my ass, Mr. Peterson! I want to feel your cum swimming in my intestines! Oh,…Jessie…you are amazing..” I got out as soon as Michael bucked my tiny teen body and shot his hot milky load deep in my chute. Oh, shit. It felt so good filling me up with all of his liquid seed.

Just as Michael’s last couple thrusts, and his balls emptied, I wiggled my entire body as I came again. A whole new experience for me. Michael let out a deep “Aaaahhh” pulling his pulsating, spent, cock out of my ass. My hole was so pumped full of cum, it started to seep out of my bored out gaping ass. Jessie went down and started sucking on my ass. Licking up as much of that cum dripping out of my ass. Her tongue felt so soft. My winking brown eye would tighten around her tongue as she lapped up more of her stepdads cum pumped into me. I could do nothing but lie there enjoying my own afterglow of finally having an orgasm. Many orgasms. If Aaron only knew how slutty his girlfriend was, at this moment, he’d be in so much shock. Jessie started to suck on her step-dad’s dick. “Your asshole tastes fantastic.” She said, giggling, holding Michael’s cock in her hand. She cleaned the rest of him off, and came up and French kissed me, spitting some of that cum in my mouth. Mmmm. My ass and Michael’s cum tasted so good.

I just looked at the three of us. A part of me felt born again. I knew two things immediately following our little affair. One, I was going to stay with Aaron, as long as he didn’t find out and leave me. And two, this was going to get real fun, here on out. It was magic. I was so excited about what else, the three of us could do, and,..WILL do….”
THE END

Well. I hope you liked this story. It was a story of fiction. I wrote it just for you. I wrote it to turn you on. I really hope it worked. I hope you started touching yourself and it got you so wet. I’d love to know if it did. Pm me. I’ll tell you, I was hard as fuck writing it. I just hope you enjoyed it. They take a long time to write. Take care, fellow readers! -Justin

Source: reddit.com/r/eroticliterature/comments/dj59su/shes_cheating_with_her_friends_dad_mf_anal_long