Awkward escort experience

I recently hired my first escort and it was one of the most awkward experiences of my life. I perused the site and found the girl I was interested in. There was no face pic but the body looked amazing so I called, inquired, and gave her directions on outfit and how to get to my place. A couple hours later, she pulled in my driveway, I looked out the window and almost fainted. The girl walking to my door was a girl I had a monster crush on in high school. I debated not answering the door while she walked up the sidewalk but decided, what the hell, and greeted her at the door. We graduated 13 years ago, couldn't be that big a deal. She came in, we made eye contact and she said, "what the fuck?" I kind of chuckled and said, "yeah, little awkward." She said, "you're not going to tell anyone, are you?" I said, "nope. Your business is your business. I'll be honest, as awkward as this is, I don't want you to leave." She said, "im not leaving. Im doing this for the money, not the hellos." I said, "good, then lets get started. Did your bring the outfit?" She said, "yes." I said, "great, donation is on the counter in the kitchen, bathroom, is down the hall, see you in a couple minutes." She sort of rolled her eyes and said, very sarcastically, "great, can't wait." That pissed me off. She came out in her red lingerie set and Santa hat and i decided i was going to hate fuck her. 13 year crush, her attitude and the fact that I was paying her gave me new found confidence. I fucked her with reckless abandon and came all over her tits. Felt amazing and was super satisfied at the end. She went and cleaned up and came back out and said, "do you want to do this again?" I said, "yeah I'll be calling again." She just stared at me and said "ok. Thanks for the tip. Should I leave the Santa hat here?" "No take it with you. See you soon."

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  • Update: I brought her around again this past Saturday night. We were each a little more open with one another this time and we had a lot more fun than last time. I asked her to wear skirt, no panties, and a white blouse to look like a naughty secretary. She added black frame glasses to the outfit herself and looked amazing. She role played and when we were finished admitted to me that she had done that one before so she was comfortable. We also made an agreement to meet once a month moving forward. She needs the money, I don't mind spending it on good sex, and it works out for both of us. She said in exchange for the rate we agreed on, she'll surprise me with a different outfit each time. they'll either be seasonal or fetish related. this is going to work out so much better than I originally expected.

  • How about getting this little slut around again soon and telling us all about it, this is a great sexy story, I hope you can humiliate her

  • Aww I just feel sad that you can't get free sex. :(

  • The school girl outfit with very short dress is a must, hide a cam or two in your lounge room and make her change there while you watch, no panties or bra, ensure she gives you a giant blowjob then take her doggie style preferably anally if not in her cunt, keep the video till you need it she might try and stay away from you, when you have a real good video or two I think you will have her exactly where you want her a nice little slutty, prostitute slave

  • When did it get awkward with Roller Girl? This sounds like a pleasant experience to me!

  • It was a great experience but it was awkward AF due to knowing her for so long, lusting after her during and since high school, and then her genuinely bitchy attitude the entire time. Will definitely repeat though and plan on being a jerk next time.

  • Make sure you go for the school girl outfit no panties no bra Buddy, fuck her up the arse good and proper you will bring her down off her snooty pedestal

  • Just treat her like the whore she is , its nice hearing about these stuck up bitches being taken down a notch or two. My ten year class reunion was great most of these girls were married and popped out a few kids already. Their bodies definitely didn't recover well from child rearing. It was also nice to see the girls that were more the plain Jane types in school really looking good. That Karma is a real insensitive bitch!

  • Yep make it a school girl outfit next time for sure exactly the same as she wore at school but with a very short dress and braless, make sure you do her anally or at least doggy as well bet that takes the smirkiness out of the little slut

  • Good for you, next time blow your load I her face and say HOW YOU LIKE ME NOW ... haha bitch

  • Back in high school , one girl in our class was extremely stuck up. She was beautiful, she came from money, or at least acted like she did. Most days if you said hello to her she wouldn't even look at you let alone actually reply back. Fast forward ten years, I live five hundred miles from where I grew up, a good friend is getting married and has a big party the night before the wedding. The stripper comes out and there she was, Linda that stuck up bitch from high school , stripping and later giving head in the back bedroom for money. It just show, you should treat everyone with respect , you never know what fate has in store for you!

  • Did you ever consider in high school she was just painfully shy due to low self esteem, and not "stuck up"?

  • No she was in with all the other stuck up little bitches there was nothing shy about her ,they had their own little group back then. Its funny how things change , when I go back to my home town and see them now they act as if we are old friends, when back in school they acted like you didn't exist .

  • I think you want her in a school outfit next time? be like fucking her all thous years ago

  • That is so good, but you should have made her undress and get into the outfit in front of you in full view, sounds like she is a really good fuck and well worth the money, next time no outfit see if you can get a discount, I hope she does oral and anal that would make her irresistible

  • Haha! Good for you. She was kind of bitchy. Hope it turns out well for you.

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