Way out of my league, until I had something. [m/f]

Ok, so, after writing this I can see why people might think it's not true. I totally understand because it is basically a dream story but it did happen to me, and I'm so lucky, and so grateful that it did. I thought I should share with you guys, so enjoy either way. This is really really long too – apologies.

Bit of background first: I'm 18, pretty average looking, and a bit of a dork at school. Have a small group of friends, but that's about it, no girlfriend or anything.

There's this one girl, she's called Emily. She's the same age as me, and about 8 thousand times out of my league. Which I'm fine with cos I get that I'm not a looker, but the fact she's in my friend group drives me crazy.

We have free periods at the same time, and all I do is fantasize.

But anyway, Emily. She has long brunette hair, incredible build/body, toned abs but is still ridiculously curvy. She has a pretty nice pair of tits, not too big, and an unbelievable ass. I'm an ass guy and it seems like most of the people on here are too, so you can understand where I'm coming from. Its huge, soft, and round. Perfection.

Me and Emily are pretty good friends. We've known each other from the start of high school so we're close. We sit next to each other in one lesson, but that's it. We talk about all sorts of stuff, and sometimes she'll flirt. I know it means nothing but it drives me crazy.

Anyway, we somehow get onto the topic of her having no money. She says that she would love a sugar daddy, and I laughed and she told me she was serious. She said she didn't care what he looked like or was like, as long as he could buy her shit. You can see where this is going? Wrong. I'm broke as fuck.

I half answer what she's saying all the while wishing I could somehow win the lottery.

She knows I love her ass and I comment on it all the time, I'll often give it the cheeky squeeze when we're walking in/out of class and it makes my knees weak. I have her on snapchat and one night she put on a properly sexy story (she's like that, shows herself off to everyone – I'm not complaining) I somehow ask for a picture, knowing her response, but still go for it. She says no and I say something about how I bet she would if I had money. She put something like "Hahaha, probably ;)"

Fuck. This is driving me insane. Fast-forward about 3 weeks and I get home to find out some old relative has died, who I had forgot even existed. She was ridiculously rich, owned an estate and a lot of shares in some big businesses she bought into when she was a lot younger. She left some for her close family, and some for the next generation, and quite a lot for her third (me and some others).

She was blunt, which I respected, and she left a note saying to us; "In this day and age, a lot of things are expensive, not like they used to be when I was your age. Some of you are smart, and some of you are not. The smart ones I hope will do with this money what they please, because I know they are going to do well in life regardless. The not so smart, buy a house or something." Debatable, I was told she always thought I was the smartest but I'm young and naive, so you already know what I'm going to do with the money.

I have anything I could ever really want thanks to my parents. I put some of it away, bought a nice car with some, and kept the rest. Also, when being given the money I asked if I could have some bills. They agreed (would take about a week) and I had $5,000 taken out.

My plan was falling into place. Emily again puts something on her story (a revealing ass picture or something) and I again send her one saying can I see it properly? She replies no, and I don't say anything, but send her a picture of 2G's. She tells me its fake, so I tell her to send me her number. She does, and it goes like this:

(me) "Hi"

(her) "Hey"

"That's real. It can be yours if you want it."

"Yeah sure ;)"

"I'm serious. I won't make this offer again, If you want it you can have it, for something in return obviously"

"Ok… what in return?"

(At this point I have a few ideas) "For the 2,000, I take you out to the mall and buy you whatever you like. Then I get 50 pictures of your ass."

"Hahaha asif you'd do that. What then?"

"I will. Then it depends if you want more."

Now this may sound unbelievable to some, but I'm a sad nerd who doesn't really need anything else in life than to feel like somebody likes me. I knew I was paying for it, but that's just like having a prostitute, right? Except I had feelings for this girl and in my head I could make it real. By the way, because of this money I start acting serious with her, like you just read. No, "you can make up or mind" or any shit like that, I felt like a don for once and I was abusing that power.

Anyway, she calls me and asks if I'm being serious. I tell her yes, and that if we hang up without a decision she won't get it. She immediately says yes and then asks me when we're going. I tell her i'll pick her up at 7, she giggles and says ok.

I was shitting myself on the phone, and totally forgot I wanted some rules. So I text her and lay them out.

"Forgot to tell you I wanted rules. If you don't like them you can back out, its fine. I want you to act like you're my girlfriend whenever I take you out. I want you to flirt with me. I want you to call me daddy. And I want you to always do what I ask, when we're together. Don't mention any of this when we're together, I want you to pretend its real. Lastly, and most importantly, don't tell a single person."

I felt dizzy writing this, I'd had sex only a few times before with one girlfriend, and I thought she might find this hilarious and expose me to all our friends. I pressed send anyway and threw my phone across my room, and did some work so I wouldn't know if she'd replied. It gets to six so I think I should probably check.

"They're all fine by me. Anything you say though…I'm only giving you pics for the money."

Thank. Fuck.

"I have more money."

She sends me a winky face and I get ready. I pull up outside hers and text her saying I'm here. Fuck ringing doorbells, right? She walks out and holy shit. She is in this grey skintight dress that comes down to about her knees, has her gorgeous face done up a little and her hair let down. I tried to play it cool, but fuck me was she hot. All I could think about was seeing her ass in it when we got out of the car, so I drove there as fast as I could.

It was a little awkward at first because I didn't really know what to say, but I'm not really shy so once we broke through it, it was asif I was playing a role of somebody else. Not me, at least. She asked me what I was going to buy her, and I asked her what she wanted. She said she wasn't sure and asked if I had anything in mind. I said a lot of lingerie and maybe some yoga pants for when we're at school. She giggled and we carried on driving. I feel something on my hand on the gearstick and its hers. She intertwines her fingers with mine and I look at her, smiling. She has this sexy look on her face asif to say you wanted this to be real, so here you go.

We get to the mall and I go around to her door and open it up for her, as she steps out I get a proper look at her legs and ass as she does. Holy shit. We start walking in and she puts my hand around her waist. I squeeze her a little to bring her closer to me and we carry on walking. We go in a few places and buy her clothes she wants, each time "thankyou daddy." or "I love you, daddy." She then goes straight into a lingerie shop. She leads me in and notices me looking at her ass again, all the while smiling. Then, when going through some panties she asks me what I think they'd look like on her. For every one, I just say amazing.

Now, I decide to push my luck a little. I wander away, looking at some other things, then on my way back, I place my hand on the small of her back. She spins around to see its me, and relaxes. Then, I lower it a little. She doesn't stop me, and so I carry on. Boom. The ass. The thing I've been dreaming of touching for not just a cheeky second in school. I have a full cheek in one of my hands and I'm squeezing it and groping it like crazy. It feels so fucking good. We're in the queue so it goes on for quite a while, and every so often she looks over to me with that same kinky smile on her face. "I want those pictures by the end of tonight." "Okay daddy." I smack her ass and I pay, and we leave.

Driving her home she says "Can I ask you about the sex then?" I say sure, and she asks me how much. I ask her how much she'd like, and she says another 2 and a half. I contemplate for a while, but then agree. I really want this girl, regardless of whether she wants me. I tell her my families home but hers isn't. "We've got all night. You can stay if you like and we can go to school together from mine." Perfect. I lay out a few things too. "I'm not the biggest, probably won't last long the first time, it's been a while, and I want hard fucking. A lot of blowjobs too. I'll give you an extra 500 if we can sleep together too." "I was going to let you sleep with me anyway daddy."

We get to hers and she opens the door. Immediately I drop to my knees and pull up her dress. I smell her pussy and then pull down her little thong she has on too. I go to dive in but then she pushes my head away and tells me to wait. She walks away from me with her bare ass out and I nearly faint. She tells me to sit on the couch so I do. She comes out in some of the new lingerie I bought her.

Black Stockings, a black g-string/panty type thing, and a black bra. I didn't know where to look. She comes over to me and sits on my lap, then puts her arms around my neck and starts kissing me. She's a good actor, because she really feels into it. I reach around and grab her ass, softly playing with it then smacking it and alternating, each time getting a little moan from her. She takes off my shirt and starts kissing down my body, until she gets to my jeans. She unbuttons them, pulls them down and takes out my dick. She holds it, spits on it, then goes to work. She could seriously be a professional dick sucker. I don't know if this is what it was meant to feel like or what because my last girlfriend wouldn't suck my dick, but I nearly came. I held my own though and regained my composure and before long she was deepthroating me, going all the way down, then slowly back up, keeping eye contact with me. I didn't think I made noise during sex, but I could actually hear myself groaning. I stopped her before I came and hoisted her up onto the chair. I pulled down her panties and began to eat her pussy. It was so sweet and perfect, I couldn't get enough. She gripped my hair and pushed me deeper, moaning and calling me daddy, then I felt her legs begin to quiver. She wrapped them around my head and kept me held down there. I couldn't breath, but fuck it was hot, so I carried on until she came. She didn't scream but let out a really cute long moan/whimper, and it turned me on even more. I turned her over and began eating her asshole. It took her as a surprise (She'd never had it done before) but she loved it. I again couldn't get enough and just carried on. I forgot I was paying for fucking.

When I had let myself rest for long enough I stood up and backed her pussy onto my throbbing dick. I toyed with her a little, pushing just past the head then backing up. Eventually she just grabbed it and took it inside of her. I started ramming her as hard as I could. I banged her for a solid 2 minutes before I told her I was gonna blow. She said she was on the pill and that I didn't need to back out, so i flipped her so I could hold onto her tits and see her face as I came. I have never blew a load like I did that night. I filled her up completely and collapsed on top of her. I started then making out with her and feeling everywhere I could get my hands. She got up and went down on me to clean me up, and to both of our surprises I sprung back up. She giggled and said maybe we should head to bed.

I happily agreed, and picked her up. I placed her onto my dick again and started slowly moving her up and down. I carried her upstairs and laid her on her bed. This time it was way less furious and I was fine with it. I had her legs over my shoulders and was holding onto her hands, slowly dipping in and out of her tight pussy. She whimpered again slightly and it turned me on even more, again. After a few more minutes I went deep again, fucking her with authority once more.

"I'm gonna cum again. Swallow it for me?" "Okay."

She laid me down on the bed and went to work once more. Slowly this time, taking care of my balls too, taking them inside her mouth. I told her it was time and she went all the way down me and played with my balls. I exploded again down her throat and she took it all, swallowing after my dick had stopped pumping.

She came back up to me and kissed me once more, saying "was that okay for you?" I couldn't even reply I was so zoned out, I tried to say something but it was just gibberish. She laughed, kissed me once more and said "thankyou for tonight, daddy. Can this be a regular thing? I'll even do you a discount." I immediately agreed and I think I said yes about 20 times just to make sure she understood. We got under her covers and spooned naked, and fell asleep.

I woke up the next morning to her laid on top of me giving me a blowjob. When I was going to come this time she didn't swallow, but turned over and let me bust it all over her ass. She wiped it all up and before going to school we laid on the bed for a while and her ass didn't leave my hands. I was addicted, I couldn't leave it alone. We went to school and there has been only a couple more encounters, but I have plenty more money and she's more than willing to carry on.

I don't know if she was faking that night but I think i'm clever enough to know she was. She did tell me she truly came when I was eating her out, she said I was really good, so I have that going for me. Like I said, I don't care if she is faking, I'm happy with the show she puts on, it's believable. I have a couple more stories if you guys would like them, but yeah, that's it. Sorry it's long.

Source: reddit.com/r/gonewildstories/comments/32ubfw/way_out_of_my_league_until_i_had_something_mf