Gender: Male Age: 27 Location: Outside Toronto, ON
|Introduction: My first escort|
I had just taken a new position at work. With this new gig came more freedom, responsibility but more importantly, a bit of extra cash each pay cheque. I had been with my girlfriend for about 3.5yrs at this point. We owned a place together, had plans for the future. Overall our relationship was phenomenal, but for time to time I found myself longing for something more.
Bored at lunch one day, I found myself surfing the Internet on my new blackberry (another perk of the job). I was feeling horny so I decided to visit craigslist to see if there were any ladies looking for a lunchtime rendezvous. Instead of viewing the personals I accidentally clicked on the escort ads. I was tempted to go back, but I decided to have a look and see if there was anything worth while on there.
I found this one lady in the first ad, Gabriella was her name. Gorgeous girl, about 30yrs old, thick ass/thighs and fair sized boobs. I thought this girl seems hot enough, why not? I had never been with an escort before but figured I’d let my stiffening cock to the talking.
Made a quick call and set up a date with her. We were to meet in 15 minutes at her hotel. Arrived at the hotel, got her room number and off I went. Was feeling quite confident in myself until I got to the room. Hesitant, I knocked on the door. A few seconds later the door opens and I see this beautiful face appear. Tim? She says. “Yep, that’s me”, I replied. She opened the door and invited me in. Once inside she gave me a tight tug pressing her gorgeous body against me. She was wearing black lace tank with black lace panties, knee high socks and heels, probably 3 or 4 inches.
We sat on the bed and chatted for a few minutes, which helped A LOT because I was unbelievably nervous. She asked, “what are you into?” “What do you mean”, I replied. “I mean, sexually, what are you into?” “Oh, I said, well…. I’m into just about anything really”
“Anything? Well, I like boys like you! For the next 30 minutes you are my bitch! my slave!” she declared. Unsure about her declaration I tried to talk to her a bit more “I don’t know about…” She cut me off putting her hand on my mouth “shut up my little bitch. You will never experience anything better, I promise” She proceeded to push me onto my back and sit on my chest. She began undressing me. Once naked she undressed herself and began to dress me in her lingerie.
“What are you doing this for” I asked. “Shhhh… trust me baby, you’ll understand soon enough”
Once dressed, she repositioned me on the bed and flipped me onto my stomach. She began to tie my hands together behind my back and tied my feet together. Flipping me back onto my stomach she positioned my head off the end of the bed. Gabriella then did something I had always wanted… she sat on my face, forcing her pussy right into my mouth. I loved it. For the next while (it could’ve been 5minutes, it could’ve been 10, I have no idea) I pleasured her better then I had pleasured anyone in my life. I loved every second of it. My face soaking wet from all her juices. She pulled my head closer, I could feel her moving around a lot more, becoming more and more vocal. Suddenly she stopped moving and a rush of liquid flooded my mouth, and all over my face.
Exhausted from my efforts she continued to sit on my face for a moment or so. She then stood up, turned around, and then sat back on my face. This time her anus was on my lips. She said, “mmm hunny, you lick a mean pussy” “Thank you!” I said. She slapped me across the face! “Thank you Mistress!! Is how you will address me, Understood?” “Ye-Yes Mistress” I trembled.
“Have you ever enjoyed a girls ass before, slave”
“Well you’re going to right now” as she spread her cheeks and put her anus on my lips. I gingerly licked, not really having a clue what I was doing. I began to lick according to her moans and movements. It seemed to go on forever. As I licked her anus was relaxing and when my tongue was near she would push down on my face… I assumed it was an indication she wanted me to probe, I obliged.
Suddenly she stopped, got up and said “Up now slave!” I immediately stood up. She pulled me close kissing me passionately. “Did you enjoy pleasing your mistress” “Yes, that was amazing mistress” I replied.
“Good, now it’s your turn. Lay on your stomach” she demanded.
On my stomach, Gabriella, or Mistress I suppose I should be calling her, sat on top of my legs. She began rubbing/massaging my back. It felt amazing, almost professional. I was beginning to relax as she worked out all the kinks in my body. She moved to my ass and massaged my cheeks. Not something I had ever experienced, but it was something. I really enjoyed it.
“Slave, have you ever had your ass played with?” She asked.
“Yes mistress I have” I replied.
“When and by who”
“When I was a teenager, I was fucked by a man”
“So you’ve never been fucked by a toy?“
and with that I felt her fingers pressing into my anus. Gently working my anus with her fingers and lube. She asked me to get on all fours, saying it would make it easier for her. She untied my hands and I quickly followed my orders.
Her fingers felt amazing, eventually adding a second finger I was in ecstasy heaven. I looked back to see she had switched to a dildo. How could I not have noticed that, I thought to myself. I couldn’t think about it to long because it was absolutely the best pleasure I had experienced with a women.
Then all of a sudden she stopped. She leaned forward, kissed my back all the way down to my ass cheeks and then in one slow steady motion licked from my balls all the way up my ass crack to my lower back again. I let out a fairly loud moan. I had never had a women do that to me before, but I liked it… a lot.
I felt the dildo pressing into my ass again. I did my best to relax as she pushed it deeper until I felt the warmth of her skin against my legs. Without saying a word I looked back to see her towering over my ass. It was no dildo; she had donned a strap on!!
She slowly began to pump my ass. Going nice and slow to work me in. After about a minute or so her pace picked up. Thrusting faster and faster, you could hear the skin of our legs slapping together as she pounded me.
Words couldn’t describe the pleasure I was experiencing. I could voice nothing expect a few moans and the words “oh mistress”
Suddenly Mistress stopped. I was so close to cumming!! I said “why on earth did you stop, I was so close”
She replied “excuse me? Did I not tell you already how to address me” she slapped my face and pushed me on the bed “for speaking incorrectly, you will clean this strap on… with your mouth” as she climbed onto my chest and forced the strap on into my mouth.
Once satisfied that I had cleaned it, she pulled me by my hair into the bathroom. “we’re going to shower together slave. Lay in the shower”
I quickly lay in the shower as she stood over top of me. She started reaching for the tap when she stop, looked at me and said “this shower is going to have to wait” “why I asked”
All of a sudden my chest was hit by a steady stream of incredibly warm water. I looked up to see that it was not water! She was peeing on me!!
“all my slaves love my golden nectar” she shouted as she directed it onto my face for a brief second. I was shocked… appalled… but oddly enough even more turned on then I was when she was fucking my ass.
She turned on the shower as the nectar stopped flowing. I stood up and we embraced in a deep passionate kiss. Every inch of our bodies was pressed together as the warm water rained down on us. Suddenly, without warning my cock erupted all over her legs and stomach as we continued to kiss. It was so incredibly intense. The orgasm seemed to last forever. My legs and arms felt weak but we continued to kiss.
We turned off the shower and attempted to dry off while still kissing passionately. We made our way back to the bed and continued kissing and playing with each other’s bodies for another 10 minutes or so. I felt like a teenager again, when you make out for the first time.
I felt myself stirring again and proceeded to press my cock against her dripping wet pussy. In the missionary position, we had sex for a few minutes until I released again. Feeling like I was going to black out, two of the most intense orgasms I had felt in my life. I collapsed on top of her for a few more minutes.
After a bit of chit chat I got up and dressed. Pulled Gabriella close one last time and kissed her. “Thank you Mistress. I needed this”
“You’re very welcome my slave. See you soon”
A quick peck on the cheek and I was out the door. When I got to my car I realized I never paid her. I quickly texted her to apologize and say I could come back in.
She responded instantly “no baby, no need that was to perfect to charge for”
“Really, are you sure” I replied.
Within a few seconds my phone rang. “Hello” I said.
The voice on the other end said “don’t worry baby, mistress doesn’t want your money this time, or ever. I hope to see you again real soon” and then she hung up.
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