Chapter 1:
“Hey Holly, I haven’t seen you in what feels like forever!” I sat in my cubicle looking up at her beaming face. My best friend, the person in this world whom I loved above all others. She smiled back.
“I know! I missed you too, so I thought I’d head over here and see if you could spare the time to head to grab lunch with me?”
“For you? Of corse, let me tell my secretary then we can head out.”
I gathered my things up and told my secretary Jill that I would be gone for an hour or so. I followed Holly out of the office. She looked absolutely perfect (as always). Ever since I first met her my first week of college, if there was one thing you could always expect from Holly, it was that she would always be dressed to the nines. Not over dressed per se, just put together. She used to always say that you had to dress like the person you wanted to be, no necessarily the person you are right now. Good advice like that had landed her an amazing job over at Chase corporate headquarters a few miles away, and she had helped me get my dream advertising job.
“So where do you want to eat John?” she asked as I held the door open for her.
“Oh wherever. You forget, I still live downtown, I can eat around here whenever I want.”
Holly had moved to the suburbs last year to be nearer to her boyfriend, my idiot best friend Jim. I loved him as a friend, I still couldn’t believe a girl like her was with an idiot like him. We decided on a small italian restaurant a few blocks away and began to walk.
“How is everything out in the suburbs?” I felt bad that I honestly had barely seen her in the past six months. Between work and my (now ex) girlfriend Sarah, I had been swamped.
“It’s good. Jim’s good. It’s just… Well… It’s honestly a little boring. You know? Don’t get me wrong, I love Jim, and out new place is great, but I just feel, well… too young to be this boring.”
“I get what you mean. You two do seem pretty settled down, considering we’re all just 25!”
As we ate we reminisced about old times and laughed constantly. Telling old stories like the time I downed a fifth of vodka after out accounting midterm and passed out in the cafeteria on a table. Or the time I had to literally carry her home from Karaoke.
Suddenly she just looked me dead in the eyes and asked “Do you remember that one time junior year when you kissed me after Dan Jennings party?”
I did. I still thought about it all the time “Umm, yeah. I think I do.”
“That is my favorite memory from college. I had the biggest crush on you”
“Really?” Holy shit, to think what I had missed. “Why did you never tell me?”
“Well why did you never tell me that you liked me? Huh? Don’t act like I didn’t know. I always wanted you to make a move, and I was too shy back then to try.”
This was so surreal. I could feel my pulse increase. I was sitting across from my dream girl, who is dating my best friend, with her semi angrily asking me why I never asked her out in college.
“I was just so worried that it would destroy our friendship.” She smiled.
“You always were so good to me. Have you ever wondered what would have happened if, you know… I had gone home with you that night?” She reached across the table and put her hand on mine.
I could barely think, let alone speak. But I saw the clock behind her, 12:43. Shit, I have to get to work. “Holly I’m so so sorry! I have to go.”
“It’s ok, I understand.” She pulled her hand back looking dejected. “Jim’s gone this weekend. Do you wanna meet up for drinks on Friday? For old time’s sake?”
“That sounds perfect! McNally’s at 9?”
I gave her a hug and quickly walked back to my office, my heart pounding, and my mind racing.
Chapter 2:
I pulled up a seat at McNally’s and ordered a pint of Guinness. The cute barmaid smiled and handed it to me. I took a sip and turned towards the door. I watched people stream in and out and finally a few minutes after nine she walked in. Wearing a tight, short black dress and matching stilettos. She spotted me and made a beeline for the seat next to me. I laughed as I saw every male eye in the room follow her walking towards me. She always had that effect on people. Women wanted to be her, men wanted to be in her. She wrapped her arms around me and kissed me on the cheek.
“Aren’t you going to buy me a drink?”
A couple hours and many drinks later we stumbled into my apartment. I walked to the kitchen and grabbed two glasses from the cabinet.
“Water or wine Holly?” I asked her as she settled in on my couch.
“Wine, duh! I’m not ready for tonight to be done yet! Thanks for letting me stay here by the way.”
I poured two glasses of pinot grigio and joined her on the couch. As we sipped our wine she leant into me, eventually laying her head on my lap.
“I don’t know if it’s just the alcohol talking, but I think you should kiss me.” She said, staring up at me with her big, bright eyes.
I pulled her up to me. “Are you sure this is a good idea?”
“I’ve been waiting seven years for this John! Don’t you dare make me wait any longer.” She straddled me on my lap and wrapped her arms around my neck kissing me deeply. I kissed her back, her soft tongue gingerly exploring my mouth. Slowly, as we kissed more passionately she began to undo my shirt.
Once she got my shirt off she led me to my room. Pushing me back onto the bed. Pulling her dress off she stood by my window in a beautiful matching set of purple lingerie (http://i.imgur.com/VGPHY.jpg). Looking back at me with a smirk she asked
“You like what you see?” Dropping her dress on a chair she turned around to me and took off her bra, exposing her perfect, round, pale tits. Slinking over towards me she pulled off my jeans before straddling me.
“I want you to enjoy every minute of this John, I wanna make you beg before I’m done with you!”
She slipped off my boxers exposing my thick hardening cock.
“Oh wow… I umm… Yeah!” She began to lick it up and down the shaft (http://i.imgur.com/B1J2ijb.gif). Looking me, her eyes full of lust and passion she kept licking my cock getting it fully hard, and wet (http://i.imgur.com/aU4TgcU.jpg), before taking it in her mouth. Slowly at first she slid the tip in, but with each stroke took it progressively deeper into her mouth, hey tongue flicking around stimulating the tip. She was so confident in her movements, gentle and slow at times, but so confident. She was completely rocking my world with her lips, tongue, and hands.
As she picked up the pace I felt myself let out a moan which made her smile.
“Oh you like that John?” And went back to passionately making out with my now rock hard cock (http://i.minus.com/i7tAfitMSPolD.gif). Right at the point when the anticipation was almost too much to bear she knelt up and slid over my crotch. I thought the teasing was over as she lowered herself onto me, but instead of slipping me inside, she began to grind against me, rubbing her wet warm pussy up and down my shaft (http://i.imgur.com/HIc6zaC.gif).
“Holy fuck Holly, I can’t… I can’t handle this! I want you!” She laughed and looked down at me.
“I told you I was going to make you beg didn’t I?” (http://i.imgur.com/4qpOqiY.gif)
Finally she gave in, and placing her hands on my chest, slid my cock slowly into her tight, dripping wet pussy, gasping as I filled her up. She looked down at me so passionately and lovingly as she began to ride me slowly, and purposefully, building up my pleasure.
“Your cock is amazing John! I feel so full I love it!” She worked her hips round and around, grinding her pelvis against me, stimulating every millimeter of my throbbing cock (http://i.imgur.com/FHPYvLK.gif). As she picked up the pace she began to moan my name as she used me for her pleasure. Never before had I seen a girl so in control. In control of her pleasure, in control of my pleasure, all while looking absolutely perfect riding me (http://i.minus.com/igcGhGm1qNFQX.gif). I could feel her getting close to orgasm and her eyes rolled back in her head as she let herself go, her tight pussy clenching and squeezing my cock even tighter.
“HOLY SHIT JOHN!” She grabbed my shoulders and began riding faster and harder, slamming her body against mine. It felt so good, it was perfect. The feeling of plunging deep into her over and over as her perfect tits bounced in my face (http://i.minus.com/i9P7vzCoOsVdG.gif). I couldn’t hold back any more.
“Holly I’m gonna cum!” I told her, concerned that she wasn’t ready/
“That’s the idea! I want you to relax and give me all of your cum!”
She jumped off me and slid to the end of the bed and began sucking me even more passionately and intentionally than before, making firmer deeper strokes with her hands (http://31.media.tumblr.com/76c2896b3d174f64c99453fd6d4c655d/tumblr_mtekhmkLiR1ra8e2io1_400.gif). I felt a huge cum blast building inside of me and I warned her, but instead of relenting she wrapped both hands around my shaft firmly and kept tugging, licking, and sucking me till it was too much to bear. With a scream of delight I let out streams of warm, thick cum into her mouth. Hearing her moan and feeling her not slow down as I filled her mouth, put me even further over the edge, and I fell back in ecstasy as she sucked out the last drops of cum from my throbbing, spent cock (http://i.imgur.com/y7XX0qu.gif).
As I lay there, exhausted, relaxed, and completely satisfied, she licked her lips, swallowed my cum without even a slight wince and lay down next to me snuggling into my embrace.
“That was as amazing as I’ve always dreamt.” She said, in a relaxed, loving tone.
“I have one question though for you Holly, why did you finish me in your mouth?” I don’t know what that question came to mind. Why not, why did you just fuck me even though you’re dating my best friend? Or, how are you so perfect? Did I just ruin the night?
To my surprise she smiled looking me dead in the eyes.
“You see, when I had your cock in my mouth I was in control. With the slightest movement in my tongue I can control every sensation and pleasure. When I finished you off I was your world, for that split second when I made you fill my mouth with your cum, I owned you. I owned every inch of you. That’s why I wanted your cum. I’ve wanted you to be mine since the moment I met you, and I finally got to have you even if it was just for tonight.”
Source: reddit.com/r/sexystories/comments/26fba5/finally_getting_the_girl_you_always_wanted
Hey guys, I hope you liked this. This is my first attempt at a dirty story all on my own (not a two person roleplay). Let me know what you think and if you would like to hear more. It’s pretty vanilla, but sometimes vanilla is fun.
I loved it
You’ve got the basics down. But it’s one of the most vanilla cheating/dreamsex stories ever :P. Would be fun if you put more flavour in future ones. Make it more extreme, go where imagination leads you :)
Oh don’t worry. I have plans for things to get crazier. I was going for romantic sexy with this one. Thanks for the advice.
/Clap clap clap. Awesome story! Cant wait for the next one!
*bows* Thank you! That means a lot.
Think you hit the mark with that one … Great pairing with the visuals. Looking forward to the next one …
Thanks for the kind words.
Thank you for this!