The night I hooked up with a playboy model (long) [MF]

Let’s address the elephant in the room. This story is completely true, no exaggerations and no lies. No matter how unbelievable you might think the headline is, I ask you to suspend your disbelief and read on. The simple facts are I fucked a woman who has posed in numerous playboy issues. Why should you believe this? I would ask the same question if I was the one reading this; obviously bullshit would be my assumption. Yet, the truth relies on one simple fact: I paid her, plain and simple. Cold hard cash definitely buys happiness, at least for a few hours. This was the first time I hired an escort and it was amazing.

Maybe you are wondering why someone would hire an escort. There are a lot of reasons and excuses, but in the end it was mostly to have sex with a ridiculously hot woman without having to put in much effort. She was a 10+, and I am a 7 on my best day; she was on a whole other level of hotness above the women I have dated. I have a healthy amount of self-confidence but this woman was along the lines of models that only date other models or professional athletes. I’m not close to playing on that level. I can get the small town hot cheerleader at times, but this was way beyond that.

A little of my backstory, I had been in an awful relationship for over a year and I finally called it off when the ex became physically abusive. I was astonished at how easily I got sucked into such an abusive relationship and I resolved to spend a year single to better myself and process what happened. Well, for a 32-year old with a healthy sex drive, going a year without sex was a hard thing to do. After 3 months into it, I decided I needed a release but I wasn’t willing to put any effort into dating yet and I did not have a FWB at the time. While browsing around slightly seedy corners of the internet, I happened upon multiple ads for escorts. I decided this was worth a try, but I was to go all in. I wanted top quality (i.e. no BP or CL) and I was willing to pay for it (top quality started at about ~$500/hr at the time). I found Gina’s website and started communicating with her. Once we both verified each other, we made plans for an evening in a few weeks.

When the day arrived, I checked into the hotel and found my best laid plan might be harder than expected. The hotel required a key card to access the guest floors; I was immediately thrown off the game plan and nervous that I might have to meet Gina in the lobby, which was quite small and the front desk workers had been super chatty. SMH. Luckily, I found the hotel had a small bar away from the main lobby area and there was a hallway from the bar to the elevators that did not force us to walk past the front desk. Problem solved! I messaged Gina to meet me in the bar at 8 o’clock in the evening.

I arrived at the bar 20 minutes early to down a few cocktails and calm my nerves before she arrived. This was not something I was used to and I had no idea what to expect from her. I had read a few primers on meeting with escorts that covered what to do, what to say, what not to say, etc. I was happy to find there was a couple groups of people in the bar already, making it about half full. I was sitting at the bar when Gina pulled up next to me. She was dressed casually in skin-tight jeans, a form fitting sweater, and knee high leather boots. [This was similar to her look (not her though)](https://photo.venus.com/im/17315801.jpg)

I lucked out and Gina was a super cool woman. When she arrived, she slid onto the bar stool next to me and casually said hi. Acted just like a friend or colleague meeting up for a drink. We chatted some small talk and when she finished her first drink, she leaned into me and whispered “let’s get out of here”. As we walked out of the bar to the elevators, I got to view one of the best asses in jeans I have ever seen; they had to have been a size 0 jeans and her little ass filled them nicely. ([example rear view](https://photo.venus.com/im/17315822.jpg)) She turned the heads of a few business men in the hallway and elevator. I just smiled the whole way up.

*******************

We had just entered my room when she wrapped her arms around my neck and started making out with me. Damn she was a good kisser, those long deep French kisses had me rising to the occasion pretty quickly. I started exploring her curves with my hands; she was in her late 20s, about 5’10”, with amazingly long legs and some great curves, 32DD specifically (surgically enhanced). After a few minutes standing in the entryway, she said “we are wearing way too many clothes.” I agreed.

She slipped the sweater over her head in one quick motion, and undid the zipper on her jeans. I took the opportunity to lean in and kiss my way down her torso, sucking and kissing the tops of her breasts bulging from her bra, to the top of her lace thong she had on. I grabbed her ass with one hand as I helped her peel off the skin tight jeans with my other. She kicked off the jeans and I stood back to take in the full view of this goddess in her mesmerizing bra and thong set. (Something like this: [Front](https://cdn.shopify.com/s/files/1/0175/5096/products/ELSE-Lingerie_Petunia-Magenta_EC-319T_Thong_Model_1800x1800.jpg), [Back](https://cdn.shopify.com/s/files/1/0175/5096/products/ELSE-Lingerie_Petunia-Magenta_EC-319T_Thong_Model-Back_1800x1800.jpg)))

As she stood in her lingerie, she said “now you are wearing too many clothes!” She undid the buttons on my dress shirt, my belt, and undid my pants. Suddenly, I was standing in only my boxers. Without hesitation, she kneeled on the floor in front of me, slid my boxers down, and took my cock in her mouth. I was fully hard at that point and she worked it expertly. She stroked the shaft as she twirled her tongue around the head, then she took it all in and deep throated it. What followed was an amazing mix of sucking, stroking, and the occasional deep throating. After about five minutes of this, she took me out or her mouth and started sucking on my balls while she stroked me intensely. I was in blowjob heaven and nearly exploded. I stopped all the action to save my first load for a bit later when I was inside her.

At this point, she told me her three rules: 1) never ask for bareback, it is never on the menu; 2) never come in her mouth, she hates the taste; 3) no ass play of any kind. If I broke any of those rules, the session would be immediately over. I was absolutely fine with that as I expected those from reading her reviews.

We moved to the king size bed and she laid down to let me explore her body. I unhooked her bra as I reached my arm around her back. Her breasts popped out and were perfect for man-made, perky with just enough jiggle to them to make them almost seem real. I kissed and sucked her breasts and nipples and started making my way lower. She raised her hips and I slid her thong off. She had a perfectly manicured landing strip, I traced it with my tongue and kissed lower until I reached her clit. I spent a good deal of time eating her clit with a mix of pressure, sucking, and licking. I then slipped a single finger into her pussy and started massaging behind her clit. Her hips started bucking in a motion to match the tempo of my rubbing on the inside of her pussy. She then asked me to add another finger, which I gladly did. Two fingers fit nice and tightly. I wanted my cock insider her bad, but I also wanted to extend this pleasure for as long as possible. Her pussy tasted sweet and was glistening with fresh wetness. She was clearly excited and ready to go.

After a good while of eating the nicest pussy I have ever experienced, I told her I needed to be inside her. She grabbed her purse and pulled out a magnum condom. Honestly, I do not need magnum condoms, my size is the definition of average. Luckily, I had thought of bringing my own and had some awesome super thin condoms with me, she grabbed one of those from the night stand drawer. She had me lay back on the bed, put the unrolled condom in her mouth, then proceeded to apply the condom to my cock without using her hands. It was a fabulous sight to watch! (([Perfect Example]( https://www.pornhub.com/view_video.php?viewkey=ph59d5f7fd40e86&t=26))

As she mounted me cowgirl, I felt her pussy grip my cock bit by bit as she slid all the way down onto my cock. I fit insider her perfectly, nice and tight with plenty of grip. She started riding me very slowly, tossing her head and long hair back and forth as she picked up the tempo. Her tits bounced as I moved my hands between massaging them and grabbing her hips to grind her hard. She got to a medium pace after a few minutes and then slowed again. As she neared to a stop, she lifted her legs and spun around without removing me from inside her. She was now in a reverse cowgirl and she started riding me hard. ([Just like this](https://www.pornhub.com/view_video.php?viewkey=fc9e1f9e1464cc636e5b))

I wish I could say I lasted another 15 minutes, but it was more like gone in 60 seconds. I exploded into the condom as she rode me hard. I became extremely sensitive and had to stop her even though I had maintained a good 75% of my hardness. She climbed off and laid next to me to give me a good show of her playing with herself. We chatted about how amazing her pussy was. She had obviously heard this before, but was very appreciative of the compliments and effort placed earlier. I am pretty sure she didn’t have an orgasm, but that was not a major concern of mine. This night of pleasure was for me.

After pouring us a drink, and playing with her pussy for a good 20+ minutes, I was ready to go again. She unwrapped another condom on me just like last time and told me she wanted it hard doggy style. I obliged. I gave it all I had, ramming my cock into her as hard as I could and as fast as I could while smacking her ass a few times. She easily took it all with no complaints. After a few minutes, I had to slow to a moderate pace, so I reached under her and started playing with her clit as I fucked her from behind. This got her to grind her hips in a nice figure 8 motion. Years later, I still dream of watching that perfect ass and those long legs sway back and forth to the rhythm of my thrusts and rubbing.

There was very little talk during this second round. My goal was to bust another nut, so I flipped her over and pushed her feet up and behind her head; luckily those long legs were very flexible. Praise yoga! This gave me a great angle to drill her hole as deep as I could. My stamina on this second round was impressive, we fucked for about 25 minutes without any breaks. But, my ultimate goal was not obtained; I could not cum a second time.

She was a total professional though, and took pride in her abilities. She pushed me onto my back on the bed, took the condom off, and gave me a sloppy intense blowjob for another 10 minutes. She stroked as hard as I could take it and gave it all she had. Yet, I was not able to finish again.

At that point, she was totally spent. We ended the evening with another drink before she cleaned up, dressed, and left. I will never forget how amazingly hot she was and the amount of effort she put in on the second round. Well worth the grand I spent.

Source: reddit.com/r/gonewildstories/comments/a5yzp1/the_night_i_hooked_up_with_a_playboy_model_long_mf