My dad's best friend is fucking hot! He's like this rugged man with scruffy facial hair and a sailor tattoo on his arm--some anchor with a mermaid sitting on the hook. It’s stupid but it looks cute on him. Fuck, everything looks cute on him. He sometimes comes to our house on the weekends to hang out with my dad and I just love it. I hate when my dad goes over to his place, though, because I don’t get to see him.
They usually watch football or work on my dad’s car and stuff. He wears tight polos and tight jeans--like from the 70's. My friends all have a crush on him but then they also have a crush on my dad. We all like older men, for some reason, but date stupid little idiots, instead. Maybe that's why we are attracted to older men, because the boys our age are just not any good at romancing or seducing us. They seriously just hump and moan.
My dad’s best friend is Greg--probably the least sexy name out there--but whatever, this Greg’s sexy! He’s divorced and lives alone but he brings along this blond bitch with him sometimes. She’s too ugly for him! She does have a nice body, though, at least for her age. I hate her for steeling my man.
So it just so happens that Greg is great at tennis and privately coaches here and there. And guess what? I’m a tennis player. So my dad had this wild idea, probably to save money, that Greg should be my coach. So Greg started picking me up on Thursday nights and Saturday mornings.
It wasn’t until recently that I started checking him out. I’m sixteen now and I love checking him out. For instance, he usually wears these white tennis shorts that show off his bulk. Yummy. I always knew he was pretty big but now I know how big he really is. I especially love when after training he changes his shirt right there beside his truck. I’m already inside the truck so he can’t see me staring at him. He stretches his arms up to take his shirt off as his dick protrudes in his shorts really nice. I seriously just drool at it. He has an amazing body for his age. If only he didn’t have as much chest hair, he probably would look like a model. I want him as my lover but he’s not cooperating. My friend, Ashly, is the biggest slut you’ll ever know. She’s really hot so guys are all over her. She already hooked up with a thirty year old man and said it was the best sex she ever had. Now she wants Greg. No way in hell she’s getting her slutty hands on my man. Not before I do, anyway.
He’s not really my man, yet, but we already fucked once; but he doesn’t want anymore which makes me sad. He did eat my pussy last week in his truck because I practically begged him for sex and he didn’t want to disappoint me, but he wouldn’t fuck me again. Maybe I shouldn’t have given him a blow job. Thing is, his dick smells really good and tastes so good. Plus, his loads are freaking big. I just can’t keep away from it once I’m down there. This week, let’s see what happens.
I guess I ruined the ending, right? Well, this story is more about how it all began and how we ended up hooking up. I might decide to write a second part if he falls for me because that’s what I truly want. I want him to fall for me just as bald as I am in love with him. This is how it all started...
So, one day I decided to flirt with him a little on the way home from practice, just to see what happened. I didn’t do it in an obvious way, just in a casual way. I was so scared of being rejected. I had never been so nervous in my life.
“Greg, how old are you.”
“Haha why do you ask?”
“Just curious, cause you look so young but I know you’re like my dad’s age.”
“Why thank you, Jaime.”
“You’re welcome. But it’s true, though, I’m not just sayin.”
“Well, I’m forty five.”
“Oh, wow, you’re old haha.”
“Thank you for the reminder. Once you get my age, you really don’t want to be reminded.”
“Aaaw I didn’t mean to.”
“Oh I know.”
“But it doesn’t matter for you. I swear, you look young, still, probably like 30s.”
He turned around and smiled at me. I could tell he was flattered. I wondered if he knew that by “young” I meant “hot.” I had never caught him staring at me before, like at my ass or boobs but this time he looked at me very intensely, so much that I had to turn because I got so flustered. His eyes are so pretty I can only look at them for seconds at a time before going crazy. That was basically me flirting with him haha.
The week after that I was supposed to meet him at his house because he wasn’t gonna have time to pick me up, so my mom dropped me off like thirty minutes before we had to leave. He told me to come and wait for him while he went over to pick something up to I don’t know where. He took like an hour so I just watched TV. I laid on the smaller couch face down with my ass was up in the air. Tennis shorts are really short so you could probably see my ass cheeks clearly.
That’s the way I was gonna stay until he came back. I wanted to make sure he got a good view of it. Seriously, my friends and I walked around the living room in our bathing suits and I never caught him checking us out. It made me frustrated because everybody checks me out. I think that just made me want him more. I wanted him to look at me and notice me.
“Hey,” he said as he came in.
I turned my head and answered: “Hey.” He was looking right at my face, unfortunately, but I stayed in that position for a while, swinging my legs up and down to draw attention to that area. I have very long sexy legs and although my ass isn’t all big, it’s nice and firm. He had to take a peek if he can call himself a man.
“I’m sorry, I just really had to do this.”
“It’s ok, I actually liked this episode. It’s cool.”
“Well, you ready?”
“Umm… Isn’t it too late? Usually we get done by eight and it’s already seven.”
“So you don’t want to go?”
“Not really haha I just got lazy laying here haha. Let’s ditch practice!”
“Hmm… Well, I guess that’s ok. Should I take you home?”
“Actually, I want to go swimming, if you don’t mind. It’s such a hot day, and my pool is gross right now. Let’s go for a swim that way we still get a work out.”
“How are you gonna go swimming? You don’t have a bathing suit.”
“I have a bathing in my bag because I go to the YMCA after school for a swim.”
“Well, sure, go for it. I’ll meet you up in a bit.”
I smiled. I always get what I want when it comes to boys but Greg was a full grown man. I knew Greg would never consider it cause of my dad and I’m way too young for him, anyway. But I’m very persistent and I would make my way into his pants, just watch. I knew my nipples were visible through my white bikini and the water just made them so much more protuberant. Greg showed up like ten minutes later in his James Bond bathing suit. Damn, he looked so fine. His abs are tremendous. He walked so masculine up to the pool and dove in seamlessly. He’s so athletic.
We started playing around, just swimming back and forth, racing and what not. I got out a lot of times to jump off the trampoline just so he could get a look at my body. My tits are small, probably because I swim a lot and have like zero percent body fat, but whatever, boobs are boobs and I wanted to show them off. Finally, one time while I was fooling around in the shallow end of the pool, I caught his glare right at them. How could he not? My nipples were seriously so obviously erect. I purposely bought that suit for that reason. I love showing off my little tits and nipples to the boys. My nipples make up for my lack of boobage. They are very perky and pink. Boys love them. So, I smiled and went up to him asking him for another race.
“Ok this is the last one, though. It’s getting late.”
So we raced but I cheated by grabbing on to his bathing suit for fun. I was hoping he would start wrestling with me in the water, but he didn’t. We got outta the pool and I was just checking out his ass as he walked in front of me. I wanted to take those shorts off so bad and spank him for being so stupid. My first move failed and I couldn’t figure out how to make my next move. As we walked into his living room drying ourselves up, I started small talk again.
“Hey, so what’s up with that girlfriend of yours, Lindsy, or whatever.”
“Lindsy? Oh she’s just a friend, nothing serious.”
“What? I saw you kiss her one time.”
“Well, Jaime, when you turn my age, kissing doesn’t mean anything, really.”
“Huh. What about sex? Does that mean anything?”
He gave me an unsettled look as if he were shocked that I would ask him about sex.
“Well, not really. I mean… are you asking me if I’ve slept with her?”
I smiled. “Yeah. Do you guys... do it?” I wanted to say “fuck” but I couldn’t quite be so crude just yet. I had to build up the innuendo. You know?
“Well, we have, but not anymore. We’ve decided not to see each other for a while. You see, she has a more serious acquaintance and I told her I didn’t want to intrude anymore.”
“Oh my god. So she was cheating with you! Greg, you’re so bad!”
He laughed. “Well, see, I didn’t know she was with anybody until after a while. She told me she was single, but in fact, she was just fighting with him. Apparently they have been at it for years.”
“Oh. Would you have still… fucked her if you knew?” I had to throw it in there because I was getting too horny by the thought of Greg having sex and when I’m horny I love to say that word. I just couldn’t wait any longer. I saw him glance at my boobs again. My nipples were probably ripping through my top by then. I could feel that tingle on them like every time I get excited. I just wanted to grab his head and put his mouth on my tits. He had sexy curly hair which I thought would be great to play with while he gave me head. The thoughts that were running through my mind were so naughty.
Again, he looked a little shocked that I would drop an F-bomb in that concept.
“Hmm. No, I don’t think so.”
“Oh you’re such a gentleman, Greg. Well, I think you’re too good for her, anyway,” I said in a smile.
“Ahh now aren’t you the sweet one. Thank you, Jaime. I promise I won’t tell her you said that. But you really don’t think she’s an attractive woman? Remember now, she’s my age and it’s not the same thing anymore. It’s hard to find women at this age who are still in good shape.”
“I know, but I think you could date younger if you tried.”
“I could, but I like sophistication in my relationships. What’s the point of going out with a girl who I cannot relate to?”
“So you wouldn’t date, say, like a girl in her twenties?”
“MMM… no. Too crazy. Girls in their twenties are such a mess. They think they’re getting old so they live out all their fantasies in a few years. They are more likely to cheat on you. Also, they tend to be very insecure and they’re not mature enough to realize how good they have it, so all they do is complain and talk about themselves.”
“Hahaha ok. Well, howbout just fucking a girl in her twenties?”
“Haha oh Jaime, you’re putting me on the spot, now.”
“Ok, that’s different. I supposed girls in their twenties are the most physically appealing. I have actually had encounters with girls in their twenties. One night stands, guess you call them.”
“Really? Oh my god! And?”
“Most of them aren’t good in bed. Of course there are always exceptions but most of them are a bit blase about sex.”
“What do you mean?”
“Jaime, how old are you know? I don’t know if I should be going into details…”
“Greg, I’m not a virgin. I know how to fuck. I’ve had three boyfriends and a few encounters with boys and even a couple girls so don’t treat me like a little girl.”
His eyes broadened. He definitely was not expecting that. I knew deep down he wanted to tell me that I was still a little girl no matter how many boyfriends I had but he didn’t want to upset me.
“You’ve messed around with girls? Wow. Times certainly have changed. You’re so young.”
“Haha it’s such a common thing now. Most girls in high school have at least made out with a girl. I actually hooked up with Ashly. You know her.”
“That short, blonde girl? Goodness, I would never have figured.”
“That’s probably because you don’t look at us that way. I mean, we aren’t like in love with each other, but we’ve fooled around and even with boys, sometimes.”
“Goodness gracious. Well, then, If you really want to know… most young girls are not very creative. I like to talk during sex and try different things, you know… experiment a little, have a little fun with the psychology of it. But most young girls just went by the standard manual. You know?”
“You mean, like dirty talk? Is that what you like?”
“Yes, I suppose, for example...
I stared to have second thoughts because I didn’t want to disappoint him. I began to think I might not please him but for him I was willing to be as dirty as I could be. I had no idea how to dirty talk. I had never really done anything else but moan and say the standard “yes, yes… harder, harder” and one or two “fuck me” here and there. But I would try anything with him. He certainly is my dream man.
Women my age are more experienced, obviously, and they make sex much more interesting and intense.”
“So you won’t have sex with younger girls anymore.”
He smiled. "Well, I won’t pursue them. If they happen to fall onto my lap, well, I am just human.”
I hoped that was a hint for me to fall into his lap.
“I don’t think girls that age like old men like me, anyway, Jaime. It’s not just that they aren’t very good at sex.”
“Oh but you’re wrong haha. You have no idea. All my friends like older men.”
“Yeah! Greg, all my friends want in your pants haha. They’re way too scared to approach you, though. They never would. Well, Ashly, I think she would haha I swear she worships you. I think that if she had the chance...”
He giggled. “Oh, no, no, now you’re just pushing it. That girl is something. That’s just not gonna happen. You’re friends are in highs school, for christ sake!”
“Who cares!? They’re all sluts, anyway. What difference would it make if you fucked them?”
He laughed. “You just surprise me. You’re way more feisty than I thought. you really do just speak your mind.”
“You swear we’re like these angels sitting on clouds talking about Jesus. My friends are all so jaded haha. All they do is smoke pot, drink beer and fuck boys.” There was a pause. I looked down a little disappointed.
“Nothing. Just kinda feel lame now.”
“What do you mean. Why?”
“Because I probably suck at sex.”
“Haha… ohh well, trust me, the boys you’re fooling around with just need a little rubbing and they’re good to go! You have nothing to worry about.”
“Well, I still would like to know what would make me great at sex. You should give me some headers.”
“Jaime, I don’t think you’re parents would appreciate me giving you sex lessons. Oh… wow, that sounded horrible.”
I practically had a heart attack. My flush was so obvious. I wanted to run to the bathroom. What he had just said just made me imagine him pounding me against the wall just to teach me how to fuck like a woman. “Greg, I won’t tell. What, you think Im just gonna go tell daddy: ‘Dad, Greg taught me how to ride cock like a champ!?’ hahaha.” I couldn’t believe I said that. I seriously was heaving. I was so horny my bikini was probably drenched with my cum. If Greg were to ask me: “Jaime, will you bend over and pull your panties down so I can fuck you silly?” I would have answered: “Yes mister” and obeyed like a slave bitch. But Greg really was a gentleman.
He shook his head in a faint smile. “Well, I guess not, but I don’t know.”
“Oh, c’mon, don’t be a dweeb. It’s 2011 it’s not the 40’s anymore.”
“Ok, what do you want to know, missy?”
“I dunno, like, what are things I could do to seduce a guy instead of just macking on him?”
“Hmm. Well, it’s hard to explain… guys like fantasizing about intelligent women; women who seem unreachable; women who seem too good for you; women who don’t flirt obviously but do it with such skill that they leave the man questioning whether she is flirting or not. If you could do that then you’re onto something.”
Next, I made the boldest move I ever had in my life. “Oh. Well, did you notice that I’ve been flirting with you all day?”
He gulped. I had never see Greg uncomfortable but oh he was uncomfortable now. “Have you?”
My heart started pounding like crazy. I knew I had finally crossed the line and put myself out there. This was the moment I had been waiting for.
“Oh my, why no, I didn’t notice at all. I thought you were just curious.”
“I-I am curious. I was just kidding haha.” I stuttered.
By now, he could tell I was nervous and I really didn’t have to tell him that I was really flirting with him. I just couldn’t do it, though. I think that the right answer would have been: “But I wouldn’t have stayed here if I didn’t like you, Greg. I have like three boyfriends right now but you’re hotter and I wanna fuck you way more.”
“Well, ok, let’s say that I had been flirting with you and you hand’t noticed. What now?”
“Well, if you were indeed flirting with me and I didn’t know it, I would probably not make a move, yet. It would be a long process of this very casual foreplay.”
“Ok, let’s skip that. I want to know what you say when you’re doing her. What is dirty talk?”
“Please… I really wanna know. C’mon, Greg.”
“Well, ok. I like to call the girl bitch and slut, things like that, and I like the girls to tell me that they’re my dirty sluts. Stuff like that. It gives me a sense of control over them as if I’m their master. C’mon, this is awkward. It’s hard to talk about this when your not actually doing it. You probably think that’s sick.”
“No, no. I get it. I actually think that’s hot.”
“I also love it when the girl dances sensually to seduce me.”
Now that, I could do! I was awesome at stripping. I had studied movies and stuff and had a bunch of moves. “Really? I love to dance.”
“Yeah! I think I’m pretty good, actually. I used to do it for my ex all the time and he loved it.”
“Well, lucky him. Not all women do that for their men.”
“I like to do it. It’s fun. Do you like the, to strip for you?”
“Yes. That is the best. THe point of dancing for your man is so you can strip and tease him to get him prepared.”
“What’s the best strip you’ve ever had? What made it good?”
“Hmm… there was this one girl, her name is Emily. She was a stripper so she definitely had the moves. She had a stripper pole in her bedroom. I think that’s why it was the most enjoyable. You know what I think it was with her, though? She was the most intelligent woman I had ever been with. She was just so voguish about everything and that’s just sexy. She never flirted, or not obviously, and you just couldn’t imagine her as a sexually driven being. But she had one of the best sex drives I have ever come across. I would have never guessed she was a stripper until she told me it after a few months of dating. She was a student of medicine. She might just be a doctor now.”
“And what happened to her?”
“She moved to Michigan to finish her career. I kept in touch with her for a while but we then moved on and we haven’t talked in years now. She was twenty-eight when I met her. She must be about thirty-three by now. Well, I rambled on about that one but she was certainly the best dancer.”
“Do you want to see me dance?”
I giggled. “Do you want to watch me dance?”
I giggled again. “Yes, me! I want you to tell me things I could do better. Yeah?”
I goggled once more. “I’m not gonna get naked, Greg, haha. I’m already in my bikini so I could be like a stripper in her stripper clothes haha. Let me just show you this routine I came up with. It’s to my favorite song.”
“Well, I guess… Let me change, then. I should put one a shirt and some jeans or something.”
“No, you're fine. It’ll take too long just wait here.” I ran to get my ipod and put it in the speaker-system thing. “Ok, I have to kinda dance up on you a little, if you don’t mind.”
He just smiled at me. I could tell he was a bit nervous. So I began to dance to this really awesome hip hop song. Just danced sexy first but then made my way into his legs. By now, I knew I had him. I wasn’t actually grinding too much or pressing myself against him, but there certainly was some contact. I could see he got a little bigger but I didn’t wanna stare too much. I bent over a few times, pulled my top down exposing the summit of my boobs, and even pulled down my bottoms a bit to show my butterfly tattoo by my pussy. When the song finished, I ended up saddled on him. His hands were slightly on my waist. No way I was gonna get off of him.
“So? What’d ya think?” I asked.
“That was really good. You are an amazing dancer, Jaime.”
“Thanks! Usually I end up taking my clothes off and then… you know….”
“Yes, of course.”
“Yeah, I usually grind up on their boners and dry fuck them haha. One time I made this guy cum even before I had all my clothes off.”
“Oh... wow. See, there you go. Boys your age need nothing more.”
“Yeah, so that was totally a PG version of what I usually do.” I was grabbing on to the pockets of his bathing suit, dangerously close to his cock.
“Well, of course.”
He made this smirk of agreement. His thumbs were rubbing up and down my waist. One of his fingers even made its way into the strap of my bottom. He looked at my boobs and then back up at me. We stared at each other intently and I finally just went for it. I put my arms around his neck, slowly, and leaned in for a kiss. But when our lips touched, he pushed me away.
“No, no, Jaime. We can’t do this. You’re just a girl, for christ sake.”
I stood up in front of him as he looked at me, probably feeling sorry for me.
“Look, you have your boyfriends and you should explore and experiment with them. Jaime, you’re a beautiful girl and you’re very, very sexy. I would be very lucky to have you but this is just wrong. I’m sorry. I just can’t.”
I basically wanted to disappear from the universe.
“You should go put some clothes on. We should get going.”
I didn’t say a word and went into the bathroom to change. I took my time. I was ashamed to go back outside. He eventually knocked on the door.
“Look, Jaime, this was all my fault. I should never have allowed such conversation to go on between you and me. It was highly inappropriate. So, c’mon, babe, let’s put this behind us and move on. This shouldn’t get in the way of our relationship.”
I walked out of the bathroom and nudged his shoulder as I walked passed him because he was right in front of the door. I still could not bring myself to speak. He grabbed my arm and looked at me again. “Are you crying?”
I was a little. “No,” I murmured.
“Jaime, this has nothing to do with me not being attracted to you. I told you, you are absolutely beautiful, but you are much too young. This is taboo, Jaime. It’s not a good idea. We can't look at each other that way.”
“I just…” I loved that he called me absolutely beautiful so I smiled.
“See, it’s ok.” He wiped a tear off my face and then took my hand. "C’mon, let’s get you home."
“I’m so embarrased.”
“No. Don’t be. Trust me, I really would if I could.”
“Yeah, you certainly looked like it.” I teased as I gave his dick a tap and giggled.
“Oh, my. Now I’m embarrassed.”
“Haha it was so obvious. Still is,” I said as I leaned in and looked at it.
“Okay. I should change. Hold on a bit.”
He went into his bedroom to change and I went in behind him.
“Jaime, what are you doing?”
“Well, if you’re not gonna fuck me, I at least want to see it. I know it’s big and I wanna see it.”
He sighed. "Wow. You are something. You really wanna see it?”
“Yes. I do.”
He slowly unbuttoned his shorts as I watched and let them fall. It was the most beautiful thing I had ever seen. It was slightly up but I wanted to see it up completely.
“Wow. That’s a nice dick.”
He smiled. “What do you want, Jaime?”
“I wanna suck it.”
He then picked me up by my legs and threw me on his shoulder to carry me to his bed. I could not believe it. We went in and he threw me on the bed. I was in shock. I was so confused. He unbuttoned my jeans and slipped them off. Then he spread my legs open and began kissing my inner thighs very softly. I was convulsing and goosebumps covered all of my body. I began to release little moans. He wasn’t going for my pussy but just around it and barely rubbing his lips against my skin.
“Jaime, you are gorgeous. You have no idea how badly I’ve desired this but I never thought it would happen. Do you want me to fuck you, little Jaime?”
“Yes, Greg, fuck me, please.” He then slipped my panties off and stood up. His cock was up now for sure. All the boys looked like fucking worms compared to Greg. He was so massive and veiny. It was a fucking creature!
“Fuck me, Greg, right now,” I mumbled staring at his dick.
He began pinching my nipples as he kissed my stomach and then made his way down. He slid his tongue inside me and devoured my pussy for like thirty minutes. I finally got to play with his curls. My fantasy was coming true. I came like twenty times but he just wouldn’t put his dick inside me. Finally, he looked up at me.
“You ready for it, sweet heart?”
I smiled at him. “Yes. give it to me, already!”
He smiled and said he was gonna go get a condom but I told him I had just got off my period, which was conveniently true. Still, he insisted on it and left to get it. Took him bout five seconds to come back.
“How do you want it?”
“Like a whore,” I said. "I am your slut, Greg, you can fuck me however you want." He grabbed me by my waist and flipped me over, lifted my ass up, and mounted me. He fucked me for an hour and I came too many times to count. I was in such an entranced state of horny that I really just couldn't talk dirty as I has planned. He was the one doing the talking.
“Take my fucking cock, you little whore. Take it all.”
All I could do was moan and scream or say “yeah” and “mmhhmm.”
When he was about to cum, I pulled it out and sucked him so he could blast it in my mouth. It was delicious. He actually tasted good. I mean that. Cum doesn’t really taste good so saying that his cum tasted good really means something. I really liked the taste. On the way home we didn’t really talk much. Just listened to music. About a block before we got to my house I told him I wanted to do it again. He said we would see but that nobody should ever find out. I gave him a kiss on the lips and told him he was my master and I would obey him so I would ever tell anything to nobody. I kissed him passionately and he kissed me back but for some reason he refused to kiss me while we fucked. Whatever, it was the best sex I ever had. I broke my promise by writing about it and publishing it on the internet but nobody we know will ever find out.
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with this note attached, it has been posted without my permission.
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