First Time With a Paid Escort

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His venture into the "hobby".
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Normal Disclaimer: This is all pure fantasy – any similarities to real people are purely coincidental.

Your comments (and votes) are much appreciated. I’m new to writing erotica and would love some constructive criticism.

Today is the day I finally allow one of my oldest fantasies to come to fruition. I have long dreamed of spending a couple of hours with a paid escort, there’s something about paying for sex that gives me a little extra thrill, or should I say thethought of paying for sex adds a little intensity to my fantasies. Today I find out if reality is as exciting as my imagination.

First, a little about myself. I’m a 38 year-old male, 6’2” tall and could stand to lose a few pounds. Some women find me attractive, others do not. I’ve been married to a wonderful woman for 14 years whom I love dearly. While we do enjoy our intimate time together – the sex has become predictable and any attempts on my part to spice things up have been met with disdain and resentment. This is why I have decided to find creative sexual release elsewhere.

The thought of hiring an escort has been in the back of my perverted brain for many years but was brought to the forefront several months ago when I stumbled upon a website where escorts advertise their services. This particular website had the escorts grouped by city so I clicked on my hometown out of curiosity and saw a menu of about 20 ladies. Normally, I would just view these as I would any other pornographic website but when I visited one of the ladies home pages I noticed she had a link to reviews previous clients had written about her. She had also listed the website where these reviews originated.

Reviews??? What was this? My biggest obstacle to pursuing time with an escort was my fear of being ripped-off or, worse yet, being arrested as part of a sting operation. As I perused this site, again with separate forums for each active city, I was intrigued. Perhaps this website could significantly reduce my concerns with pursuing this fantasy. Fortunately, my hometown had a very active forum and it wasn’t long before I had learned as much as I could about this “hobby” without actually participating in it.

After several months of periodically reviewing the other “hobbiest’s” posts, I was able to create a short list of ladies who I thought could provide me with a good, first-time experience. Finally, I decided it was now or never so I sent two of the ladies an e-mail with the information they required for screening new clients. Each of the ladies requirements were a little different but this information generally consisted of my real name, place of employment and their main phone number (to verify my employment), and a preferred method for them to contact me (e-mail, cell phone, etc.) and 2 references if I had previously seen other providers. While I was a little nervous about sending this information, I recognized that these ladies’ reputations and occupation required them to be discrete with their inquiries.

One of the ladies responded via e-mail within a couple of hours politely turning down my request to spend time with her as she “was not accepting new clients at this time but appreciated my interest in her” and encouraged me to check back with her in a couple of months. While I was disappointed I had half-expected this response as she was one of the more popular providers on the review website. Happily, I received a call on my direct line at work from the other lady the next day. When she told me who she was and that she would love to get acquainted, I was so excited I almost came in my pants! I felt like a high-school kid asking a girl out on his first.

Once I got over my school-boy nervousness we managed to set a date for the next day as well as the time (noon) and location (a decent motel close to my office). I was so distracted that night my wife asked me, “What’s wrong with you this evening?” I just mumbled something about a big meeting the next day at work and I just couldn’t get my mind off of it (if she only knew how true that was!). Finally, this morning came and I had to get ready.

After I took my shower, I ate breakfast, gave my wife a kiss good-bye and went to the bank to withdraw the lady’s fee plus some extra from my personal account and went on to work. I don’t remember what I did that morning except to look at my watch every fifteen minutes waiting for the appointed time to arrive. Finally, the time has come to go and after telling my boss I had a doctor’s appointment at lunch and might be gone more than the usual hour, I hop into my vehicle and practically race to the motel while chewing on mint gum as this lady had stated bad breath was a major turn-off for her.

I had two envelopes in my breast pocket, one with the lady’s required fee and the other with a possible tip if I felt it was appropriate. While doing my research on the review board, many of the experienced hobbiests had suggested the best way to approach these encounters is as a business arrangement first and then let the lady take the lead. But when I knocked on the door exactly at noon and she opened up the door, it was very difficult to keep my mind on the business side of things. She was absolutely stunning and that school-boy nervousness quickly came back to me which she seemed to notice right away. So she gently grabbed me by the arm and guided me into the room after introductions were made.

Let me take a moment here to describe this lady. The short description would be “blonde Amazon” – she listed herself as 5’10” tall with 38D-28-38 measurements. She has the brightest green eyes I’ve ever seen and her blonde hair went about halfway down her back. Her curves were absolutely fantastic and the black dress she wore perfectly accentuated every single one of them. Her heels made her a little taller than me which turned me on tremendously. I don’t often have to look up to see a girl’s eyes and this was a wonderful change for me.

After guiding me into the room, she gave me a hug at which point I caught a faint whiff of her lovely perfume. She told me to relax and “get comfortable” while she excused herself to the restroom. As she turned to walk away, she grabbed my hard-on through my pants while giving me a wink and blowing me a kiss. I nearly jumped out of my shoes at her unexpected touch. After she closed the door to the restroom, I placed the envelope with her fee on the dresser, got undressed, slid under the covers (I was still nervous), and waited for her with the hardest hard-on I’ve had in years.

A couple of minutes later, she came out of the restroom wearing nothing but her heels and posed for me at the foot of the bed. My jaw literally dropped to my chin and I believe I even drooled a little bit. Her breasts were absolutely stunning and her areolas were perfect. Her stomach was flat and led to the most wonderful hips and shaved kitty. After standing there with one hand on her hip, she turned and showed me her most famous feature – her stupendous ass. It was bigger than what most might like but it was firm and oh-so-rounded. I felt like jumping up and down and applauding but all I could manage was a “Wow, you are amazing!”

She kind of giggled then crawled up on the bed next to me and gave me the lightest of kisses on the lips and asked me what I wanted to do. I kind of stuttered out, “Well, since this is my first time in this hobby, I thought I would leave the menu up to you.” She just smiled as she ran her fingers through my chest hairs and said she would take good care of me. I just gulped and said, “I’m at your mercy but I would like to taste that wonderful pussy of yours at some point if you agree.”

She just grinned and started kissing her way down my chest to my stomach, moving the covers as she went. Finally, she exposed my raging hard-on and gave it a good squeeze with her hand – I almost exploded right then and there but I somehow managed not to. Soon she was kissing and licking the head of my cock while her hand alternately massaged my thigh and my balls. Slowly, she took my cock into her mouth and I was in heaven. It had been so long since I had received a blow-job I had forgotten what it felt like. Inch-by-inch, she worked her way down until my whole cock was in her mouth, then she slowly worked her way back up until the tip popped out of her mouth.

I told her I wasn’t going to last long so she engulfed my cock again and proceeded to give me the best head ever, swirling her tongue all around and sucking like the pro she is. After a couple of minutes of this, I was ready to erupt at which point she took my cock our of her mouth and gave me a couple of strokes with her hand and I shot a string a couple of feet in the air while she kept pumping and pumping. I can’t remember the last time I came that much, it seemed to go on forever. Once I was spent, she gave me another quick kiss and went to get a wet washcloth and towel to clean me up.

While she cleaned me up, she noticed I had a bit of a disappointed look on my face and asked what was wrong. I told her the blow-job/hand-job was great but I really wanted to have sex with her. She just laughed and said, “Silly, we still have plenty of time left, I’m sure we can come up with something to do.” She then gave me another kiss on the lips and laid her head on my shoulder while stretching out her body next to mine. I asked her if we could spoon, so she turned facing the other way and scooted down with my right arm underneath her head and my left arm draped over her bosom.

Slowly, I started kissing her neck while my left hand started massaging her breasts at which point she pushed that beautiful butt of hers into me and gently moved her hips up and down as if she was giving me a lap dance while laying down. As I played with her nipples, they came to attention and I just had to suck on them. So I moved enough to allow her to lay on her back and I gently started sucking on first one, then the other nipple while my left hand massaged her legs and that smooth tummy. I kissed my way down her stomach to her pubic area at which point I asked if I may go down on her (not all escorts will allow this). Her only response was to spread her legs wide as she started squeezing her breasts and pinching her nipples.

So I maneuvered myself between her legs and started by licking the outer folds of her delicious pussy, slowly working my tongue into the well of her femininity. Her juices were sweet to the taste and I drank from her like a man who had been lost in the desert for several weeks. As I alternately teased her clit and licked all over she grabbed my hair and bucked her hips, grinding my mouth into her harder and harder. After what seemed to be both eternity and mere seconds she lifted my head up and pulled me towards her. She quickly grabbed the condom that was resting on the nightstand and slipped it over my re-invigorated cock.

Next she flipped over onto her hands and knees so that I could slip into her doggie-style. By this point, I was overcome with lust and grabbed her wonderful hips as I guided my cock into her woman-hood. Once I was in all the way, I stayed there for a little while just enjoying the sensation of finally being inside her. Soon she started moving her hips and I took the hint and began pounding her with everything I had. She felt fantastic! After several minutes of this, I could feel my second orgasm welling up inside me until I finally exploded again – completely satiated and exhausted.

I then took a quick shower and watched her as I got dressed – she was still naked laying on top of the bed watching me. I took the second envelope out of my jacket pocket, laid it next to the other one on the dresser, gave her a quick kiss, and promised to call her again sometime.

Was it worth it? You be the judge – the best sex I’d had in years and no worries about an emotional attachment. Will I call her again? Maybe. There are many other escorts in this area though….maybe next time I’ll write about the one I talked to this afternoon…

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