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randyrockhard
20-09-2020, 06:36 PM
It was a few days before I hit my 40th birthday that I got to know Tanya from a dating app when I was on a business trip in Big Durian.

At the time she was only 22 yrs old and just started her internship at one of the big four law firms there.

What attracted me to message her in the first place was her upside down profile photo with her eyes being crossed out with red line, her light skin, with a shy smile on light pink lipstick, while wearing greenish gold QiPao.

She also wrote on her profile that if you do the right thing, you would hit the jackpot.

I casually messaged her and started a light conversation with her, first was to gauge what her intention was, second was to at least have a decent conversation.

The vibes that I picked up from our conversation was that she seems like a nice girl, but somewhat a bit shy. I later learned that she was brought up with a strict upbringing causing her all kinds of issues about self esteem and keeping a healthy and positive mindset is always a challenge for her.

I established with her what I think about hooking up and she seemed open to it. She confessed that she never done it before, but if someone is pleasant enough she is willing to give it a try.

My meeting venue the next day happened to be just across her office building, so I asked whether we should meet up for lunch. And to my pleasant surprise, she preferred meeting up for dinner instead.

She asked what food I wanted to try in her city, and I told her that I was open for suggestions. We finally met up and some western food restaurant and that's where it all started....

<To be continued>

bigmannow
20-09-2020, 09:04 PM
camping here .....

randyrockhard
21-09-2020, 09:39 PM
Before me and her agreed to meet up, we discussed extensively our rules and boundaries, especially the things that she likes and the things that she doesn't like.
And with me being the much older party, I tried my best to accommodate her wishes.

We met at a restaurant only a short walking distance away from my hotel. There she was, 173 cm tall, straight black hair, exotic eyes and oriental nose. A bit too oriental for my liking, though. When she smiled, I could see that her teeth isn't too perfectly aligned.. but her hip though, looks really deadly. 😝

Personality wise, I can tell that Tanya is a bit shy and there is this tendency for her to self-correct her own words. I knew that she was nervous.

So I tried as much as possible to ease the tension by acting natural, just by being attentive, pleasant and caring with a bit of naughtiness but respectful. Still no touching.

At that moment everything was still in doubt whether I would be able to hook up with her straightaway that night, but then I saw that she was carrying a large bag, which was basically her stuffs. Usually this is odd for a one night stand, but then she seems like she never done it before.

At the end of the meal, I casually propositioned to her that I would be more than happy to have her joining me back to my hotel. She just smiled and nodded.

That's where I knew I almost hit the jackpot.

We went back to my hotel and we started slow, by taking shower separately. Afterwards, she was still a bit shy and nervous and she asked to dim the lights. We started by laying down next to another, I turned around and started to kiss her slowly, slow and gentle and then i suddenly plant a deep kiss on her lips. From that moment it was a series of discoveries .... where I learned about her weak spot, which to my surprise it was her right toe. Everytime my feet touches her toe, she always moaned, I kept on teasing and teasing. Until she couldnt resist any further and asked me to penetrate her.

I put the cap on, and she asked me to be gentle, to which I obliged. Little that I know that she seemed to have some sort of vaginissmus condition. She told me that she always had painful penetration. I was taken aback by her admission because it means that I have to be very patient and slow.

Well the thing is... Taking things slow is usually not good for my erection... Lol

I tried so hard that evening to stimulate her and after almost half hour of trying, I finally managed to get it in.

The feeling was surreal, she was really tight and warm. It was probably the most comfortable and relaxing feeling I had in many years and with such young delicate woman writhing in front of me, I couldn't last too long.

(To be continued)

chouck
27-09-2020, 11:16 PM
Please continue bro! :)

randyrockhard
25-10-2020, 04:13 PM
With all the big bags that she carried from the night before, Tanya asked whether she could leave them during the day at my hotel so that she didn't have to carry them to work. I thought sure, what's the harm in it and probably we were just not gonna see each other again.

I asked her if she wanted to grab a dinner after work and she was fine with it.

I returned straight to my hotel after finishing my business meeting, and my hotel decided to send me a surprise birthday cake to my room in the evening. I saw the cake and it had my real name being crafted onto the chocolate icing. I knew that perhaps with a hookup it may not be a good idea to let them know too much of your identity, so I decided to eat the cake part with my name on it. ��

We had dinner that evening and surprisingly she wanted to stay with me again. I thought to myself, wow... what a birthday present from the heavens to have a girl 20 years younger than me, wanting to fuck me again 2 nights in a row.

I discovered that she haven't had sex for quite a while since she broke up with her ex a few years ago. I was in for the greatest ride of my life.

(To be continued)