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  1. #1

    Join Date
    Dec 2018
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    Anna a New Adventure - 1

    Anna Story First meeting

    It was a cool fall night in Toronto and I had meetings near the airport, so I got a hotel near the airport, the Homewood suites. It was a haunting night and my meetings were done. I wanted some company so I searched the internet and looked up High Society Girls finding a hot lady who went by the name of Anna.

    I contact Carmen who I had heard about in Vancouver but never got to see. She was now the owner of HSG. We had a nice talk about the provider world back in Vancouver. I told her what I craved and she recommended I meet Anna.

    Anna was Russian, older provider late 30’s early 40’s. Blonde, tall, man made boobs but with a youthful appearance. She was not a spinner, but, well not heavy. She had a porn star look to her, nice cheek bones, and smoky eyes with just the right amount of make up.

    She arrived on time for an hour appointment. She had a hot accent and was wearing a black dress, pumps, black stockings with garters. She was so fucking hot. I think the most beautiful and by far the hottest provider I had ever seen. She was like out of a fantasy. I was paralyzed by her beauty. I was tongue tied and she was my perfect beauty. We chatted, mostly she chatted, and she seemed distance, very Russian, and we shared pleasantries. Then she said.

    “You alright there?” She asked and smirked. “Like what you see?” she continued in her Russian accent.

    I nodded and then cleared my head. Come on, stop acting like an idiot! I told myself and then looked at her. “Yeah.”

    “Haven't seen you before, do you see many escorts? Where are you from?” She asked, almost ironically given our small talk before. “Have I been here before?” now there is a question from the Russian lady.

    I scratch my bald head thinking what? “No, Yes, Europe...” Had we not just covered this already?

    “Looking for someone, or something in particular?” She asked and I nodded. After a second of me not talking she smiled. “Am I what you're looking for?”

    I thought for a moment. I didn't want to offend her, again I was gawking at her she was so hot. But she must get that all the time. She was a escort. I could not speak.

    “You don't do this often, do you?” She asked, not waiting for a response. “Well, I just started this myself.” She started to tell me her story.

    I couldn't believe that I was actually sitting here and not ripping her clothes off. Yet I knew I was about to have sex with her.

    “What's your name?” She looked at me next to her.

    “Greg. You?” Dump question. I knew the name Carman gave me and her ad was on the internet.

    “Call me Anna.” She said and turned to use the wash room.

    She came out and almost immediately slid out of her dress, revealing two large C-cup breasts hidden under a purple and black bra. She walked over to me and took off my shirt as I stared at her chest.

    She took my hand and led it to her breast, thinking I wouldn't do it myself. She then reaches back and undid her bra as I started to work on her breast. She couldn't help but let a moan escape her lips as I played with her, lightly rubbing my thumb over her erect nipple. She leaned in and then kissed me deeply.

    I had kissed many a SP before. This wasn't new. I held her close, rubbing her back as my tongue slipped into her mouth. I broke the kiss and started to kiss down her neck, lightly nipping at the skin. She started to get wet as I kissed her deeply, standing only in her panties now. I kissed down her neck and got to her breast.

    I began to tease her a little bit, tracing circles with my tongue around her nipple. I didn't know if what I was doing was right until she moaned, stroking the back of my head. She had no idea why I was doing it, trying to turn her on so much. She was being paid to give me pleasure. I think she was confused.

    She pushes me away and then sat me on the bed, taking off my suit, revealing my hard cock. It was surprisingly big, and very thick. She commented
    “Oh my you are a big boy, I hope I have condoms big enough for you” as her eyes light up.

    She lightly glides her finger tips across my shaft and I groan and lean my head back. My cock twitched, releasing some pre cum. She seem to like that, and licked it or was it to get a closer look. She tried to get her hand around my shaft. In her excitement she lets out.

    “Holy fuck you are thick. I can not get my hand around you. I think I will enjoy you.”

    She licked up my length, making me shudder with pleasure. She takes my head into her mouth, her tongue twirling around the tip, closing her eyes and going down on me until my tip touched the back of her throat. She began to play with my balls in her hand, sucking my cock at the same time.

    I watched her, still not fully believing that it was happening. To me she was very sexy, and now she was sucking my cock. I wanted to fuck her so badly, but wouldn't object to a blow job, figuring that either way I was getting off with something other than my hand.

    After a minute she sped up and I felt myself getting closer to an orgasm. I looked down at her, panting. “I'm going to cum soon Anna.” I moan as my cock twitches and I shoot my load into the back of her throat.

    She swallowed it and then got up and took off her panties. “Gotta get you hard again then.” She said and walked over to me. I took her and then threw her down onto the bed. She didn't expect it, not from me. I lean down and then licked her slit, causing her to moan loudly. Guys rarely ate her out, she rarely ever had orgasms because of it or so she told me later.

    I knew very little about how to make a woman like her have an orgasm, only knowing a little bit from my past experiences. I was moving her hips to my face though, so I figured I was doing a good job. I played with her clit with my tongue, penetrating her. I moved my hand up and started to finger her, using one finger at first and then moving it up to two.

    She felt the waves of an orgasm washing over her as her body shook for a moment. “Oh my god!” She yelled as she had an orgasm, her juices coating my finger.

    She looked down at me. “What was that?”

    “Sorry, I didn't mean to-”

    She smiled lightly, panting. “No, it was good... Lay down.”

    I didn't argue, just laying down on the bed. She climbs on top of me, positioning my once again stiff cock at her entrance. She about to lowered herself down onto me, and then paused. “We need a condom.”

    She pulled one from her hand bag and ripped it open and struggled to put it on.

    “Fuck you are big, I can not get it on” but not like a she was disappointed. She tried another this time I helped her.

    Things changed. I looked up at her and she leans down, kissing me. Kissing me with such passion. She was not distant any more. We held the kiss for a few moment before she started to move herself up and down on my cock. Slow at first then faster. She let out a “OH FUCK YOUR BIG” Her tight pussy walls gripped onto my stiff cock, and it took a lot of energy to try and keep from cumming, I wanted to make it last as long as possible.

    She started out slow, bouncing up and down on me then grinding me. It was very sexy to see her on top of me, riding me cowboy style. Enjoying me. Watching her head go back and forth. Watching her eyes closed and her face tensing up. Her large breasts moved with the rest of her body. The friction between my cock and her pussy was driving both of us mad, our groans filling the room.

    I could only hold out for five minutes before having my second orgasm. I filled up the condom with cum, her pussy now dripping with her juices. We look at each other, both panting, both satisfied.

    “We should do this again.” She pants and then kisses me, laying on top of me, her naked breasts pushing against my chest.

    Even though she was a prostitute, I did want to do it again. I called Carman and asked if she could stay longer and I got another hour to do her doggy and missionary. Then both of us got up, she got dressed, and she went back to work, and I got to dream about her.

    She did give me her email and told me she should not give this to me but she wants me to contact her again. She really wanted to see me again. I really wanted to see her again. So it started, a new relationship.



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