This story happened about 6 months ago. I was on a consulting job out of town when I got an email from one of the boss’s at the consulting company. The email was very nice and complimentary of me and my skills, near the end I got the sense it was the slightest bit flirty. I emailed her back (she is my boss’s boss) and decided to say something about how I looked her up on Facebook and I think she’s cute. She can text me if she wants. I was a little worried to be unprofessional but figured, I was complimenting her and based on my success with the company she’s not going to hold a compliment against me.
About 20 minutes later I get a text. We start texting back and fourth. And over the next couple of weeks things get more flirty. I’m saying she’s cute, she says I make her blush, yada yada yada. She has a fun, spunky personality so one day I text her that her personality turns me on. She responds that I shouldn’t text her things like that. (She is my boss’s boss after all). And she says she has a boyfriend….apparently.
Anyways, we keep texting being flirty, I make sure not to push it over the line. But after about a month I want to see her. I ask her to fly out to me. I tell her I’ll be happy to buy her ticket. By this time, we’ve already bitched about our company to each other so we both trust each other not to say anything to anyone. She plays hard to get a little, like she shouldn’t be doing this but she relents and let’s me book her plane ticket.
I go to pick her up at the airport. She calls me and tells me she’s standing outside at baggage claim but I don’t see her. I keep looking around but she’s not there. Finally I get out and walk, telling her to meet me. As I’m walking a cute as fuck blonde girl, good body, blonde curls, cute innocent face gives me a look like “Hey dude”! I smile politely and keep walking. Then she says my name and asks me where I’m going. I’m surprised because I don’t know her then realize she’s the girl!! My boss in the Facebook pics always had pics with other girls so I has assumed she was one of the other ones. She was actually one of the hotter ones. I feel so lucky in this moment. She’s mid 20s, 5’3, 120-130, longer blonde curls, face kind of like Holly from the show The office.
Like this but younger. http://imgur.com/3LY6ddn
Here are a couple pics of me….
I give her a hug and we get in the car and go to my place. We just relax, make small talk and go to dinner. We haven’t talked about having sex, but it’s kind of assumed.
When we get back to my place I pour us some wine but before we start really drinking it I give her a long kiss in the kitchen. We stand there kissing and touching each other arms, bodies, faces, you know. I start feeling her titties through her shirt and unhook her bra. Then I pull her waist into my crotch letting her feel my stiffness push against her pussy. She starts to grab my cock through my pants and we make out harder. I suggest we go to he bedroom.
In the bedroom we lay down right away and continue as before. We start undressing slowly. I start pushing and fingering her through her pants. I can feel the warmth through her jeans. As she gets her panties off I lick 2 fingers and slide 1 inside her. I start fingering her slowly and exploring her pussy while making out with her. I slide another finger in and finger her with 2 fingers and curl back to her G-spot. She’s getting so wet and her moans are so fucking sexy with a little high pitched sound at the end. She playing with my cock, jacking it off lazily with 2 hands as she enjoys the fingering. She opens her eyes and says “The flight from Texas was worth it”, with a sly smile. There’s that spunky sense of humor, I think.
We are naked now and she is nice and wet. I get on top of her and slip inside her. She has such a nice pussy, inside and out. She’s a little short and has a nice short pussy to match as I bottom out in her I can feel my cock hit a wall. I love this because I know I’m going to be able to wear her out and leave her pussy sore.
I start fucking her missionary and we are both enjoying it. Changing positions slightly between putting one of her legs up, both legs up, her legs wrapped around my body, etc. My head is down near hers and she starts kissing my ear, then she starts licking it. She’s licking it like she’s eating pussy or something. This feels really good!!!! Much more than you’d expect. Especially when you are comfortable with your dick in a warm, tight pussy.
We have sex in that position more and she cums. She doesn’t tell me she’s going to cum (which I wish she would have), she just starts moaning in a certain way, her moans getting louder and more powerful before she digs her fingernails into my arms and moves her mouth up to meet mine as she cums all over my dick.
I feel her pussy get more wet as her orgasm subsides. I move her onto her stomach because I want to enter her from behind and just pound down on her little body. As we move positions she pulls me into her and kisses me hard. Letting me know she loves this.
I lay on top of her, spread her ass and let me cock find her pussy. She lets out a good moan when I get inside. I tell her I want to cum inside her and she says “No, we can’t”. I don’t know why not, but whatever. I want to have her again so I’m not going to push it.
I start fucking her with her ass bouncing up to meet my pounding. We are sort of alternating between semi-doggy style and her flat on her stomach. She starts moaning heavy again and within a few seconds of moaning she has another orgasm. I slow down as her pussy is too wet now, I can barely feel my cock. I take it out, wipe off her juice and slide it back in. It feels perfect now. I start moaning now, letting her know I’m getting close. And telling her how her pussy is sucking on my dick.
She turns her head around and nervously spits out that “You can cum in if you want”. I smile and lean down and kiss her. I start slamming her pussy harder for a few more seconds before I start to cum. Hugging her body and kissing her hard as my ropes of cum coat her insides, painting her white.
We stay in this embrace for a minute before I roll off her. She gets up to go to the bathroom and I just lay there smiling with her eyes closed. I’m so happy with my life, I think arrogantly.
Turns out she didn’t have a boyfriend. Just some guy she was casually seeing. We dated for a bit, I like her but the long distance thing is hard for a committed relationship. So all you Trolls can just find a bridge and jump off.
Hope you enjoyed. Ladies…PM me, let’s talk, I’ll fly you out and we can make our own story :)
Source: reddit.com/r/gonewildstories/comments/462uy3/creampie_for_the_bosss_boss_picskinda_29m25f
So from your pics you’re in the top 5% of attractive men so any story you tell is like a highlight reel from any movie.
Your boss’s boss is 25?
> She’s a little short and has a nice short pussy to match as I bottom out in her I can feel my cock hit a wall. I love this because I know I’m going to be able to wear her out and leave her pussy sore.
You can injure someone doing that.
https://www.google.com/search?sourceid=chrome-psyapi2&ion=1&espv=2&ie=UTF-8&q=bruised%20cervix&oq=bruised%20c&aqs=chrome.1.69i57j0l5.5495j0j7