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Introduction:

An online hookup with low expectation turns out better than expected
Let me start by introducing myself. I'm live in a city called Toronto where women are very pretty. I'm in my early 30s, stay healthy and fit and am considered 'good looking' by normal standards. I've had my share of adventures and fantasies come true.... and have decided to post one such recent encounter.. From my looks people wouldn't consider me someone wild.. In fact some would call me reserved and gentleman like with boyish looks when I dress casual and smart when I dress for business.....

Enough about me...

It was a bright spring weekend day.. People were out on the streets enjoying the weather change and the events happening in the city... I had been home all morning, just finishing up work, emails...

A few days before I had been online on a dating website and had starting chatting with this girl who showed quite a bit of interest.. She was openminded, sexual and fun to speak to... Her pictures however did not have the same impact as her text.... I wasn't overly excited... On the other had she definitely liked my pictures..(again, I'm no Brad Pitt, and have been rejected by many.. just like all other guys... but every once a while I get lucky)..

So I had somewhat gotten lucky.. Sort of lucky....

Anyway, she called me and I regretted for a moment, giving out my number... She wanted to see me.... I decided to take a chance and let her know that I had only little time as I was meeting friends later... She agreed to meet and maybe drive around, have coffee... as she as coming to the city and was going to be close by.....

We met at a parking lot and I could see she was instantly attracted to me...I wasn't as we had exchanged pics and I knew what was coming... She was a short asian girl (I like asians otherwise, but she wasn't my type)... Sweet smile, tits, a bit on the plump side and seemed no more than 23....

As decided, I reminded her of my time constraint and she agreed to drive around in my car......

She told me her weekend had been lame... I asked her why? She said, she was expecting to get laid.... and she did get laid.... but her 'friend' who she had been out with a night earlier... Who had been trying to get into her panties finally succeeded.. She gave-in but was disappointed by his size...... although she did say he was awesome at getting her off... He was great with his fingers and his tongue.....

My cock had already started to twitch as she described her experience in more detail than expected..

She said, she wasn't getting attention at all... and that the guys who she liked never gave it to her.... The way she said it made me feel bad... She had sensed rejection and I didn't want to make it more obvious I was not attracted to her...

Anyway, to be polite, I asked her more details about her last night... and she described her semi-unsatisfying encounter..

After a few more minutes of driving around, hearing her story.. I was fully hard.... and she sorta saw my bulge.. I was wearing jeans and a boxer inside and my cock was pushing upwards... In a few more minutes,

She asked me if I was a disappointing size too.. and I answered that I don't know what size is disappointing for her.. What's her threshold..?

So she started to unzip me.... I was startled but horny as hell..By now I was thinking from my dick....

At this point my brain had rejected the idea of NOT doing anything sexual... I couldn't care less if she wasn't as attractive...

I told her to hold on as she struggled with my zipper.... We pulled into a parking lot which was empty.... I unziped and whipped out my cock..... she let out a "sigh"... and she said I want it in me RIGHT now... Take me home please... she begged me.... I told her i needed to see her pussy, it was a fair deal..... (just for fun)

She pulled her jeans and panties down in an instant..... She was clean not freshly shaved but good enough.... Her pussy wasn't bad... swollen lips and a small clit that was erect... I inserted 2 fingers and loved that she was so wet.....

That's it.. we went to my place right away...

As soon as we got in... we got naked... .. I hadn't had sex for many weeks and was pointing to the ceiling... Yup it happens to single busy professionals sometimes...

she sucked my cock like a champ..

She licked the top of my cock head, then the underside all the way up to my balls.... she had her hands on my ass and the slid it and started playing with my balls as she sucked me well...... But didnt make me cum... I take too long and wanted to go inside a pussy...

I hurriedly put on condom..... it was a thin type condom...

... we fucked like animals... Starting with missionary... I teased her a little at first by rubbing my cock on her pussy, clit.... and she went wild.. She pulled me in and her pussy swallowed my cock....... she let out a moan that was so HOT.......

I started fucking slow and deep and increased my pace... he moans too became intense....

We changed positions...

I would literally pick her up into a new position every 8-10 mins... She was short, which I absolutely LOVE... I loved it when I pulled out, made her go on all fours in one swift strong actions....

From behind too.. I teased with my cock head rubbing all over her cunt...

I held her waist and fucked her wild and she screemed..

Finally I made her come on top... fingered her clit hard while she bucked wild....She had a big orgasm and i could feel her clench.... it was AWESOME..... She thanked me and said she had never had an orgasm with a cock.... I loved it..

anyway, i told her its her turn... she said im all yours....


I fucked her missionary with pace.. and built myself up for a huge shot....

I told her I had never cum ON anyones lips.... or face.. always had cum inside a mouth or pussy or on tits..

She agreed with a smile... she sucked me like there was no tomorrow.... i helped her by jerking off..... she had her tongue on my cock head and gently squeezed my balls..... that got me off the edge and i shot stream after stream on her tongue, inside her mouth, on her lips.....

I felt drained... but I dont wanna do her again.... Im not attracted to her.... and she understands it... but she thanked me and said I could fuck her anytime i wanted..

I sometimes feel like such a bad guy for giving someone a pity fuck.. or maybe I'm just a guy...... and maybe I did her a favor... I'm definitely NOT going into a moral debate with myself anymore... bottom-line is, cum on her face was priceless... :)

So that's my story... My first story (of a recent encounter)...... Comments welcome..!!
6 comments

anonymous readerReport

2011-07-10 15:12:53
The best pussy in my life was with a chick who told a mutual friend she was 19, ready to lose her virginity and wanted to know if I would help. She was not pretty at all, and had kind of a dumpy figure to boot. I only pity-fucked her because it was free pussy and a chance to bust a cherry. She did not turn me on at all, but she was awesome in bed. I guess she knew she wasn't going to catch too much cock and she decided to make the most of her first time. She could really roll that big ass and she made every drop of my come flow out like oil. It was and remains the best fuck of my life. My wife is a beautiful woman, but she's never made me cum like that virgin did. I wanted her to blow me, but I was actually afraid if she sucked as good as she fucked, I might be unable to walk away from her. I think unattractive girls know they have to try harder and probably are hornier due to lack of activity. Pretty chicks think all they have to do is lie there. I'm glad I had that pity fuck.

anonymous readerReport

2011-07-10 14:40:45
Liz used to chase me all the time when I was in college. She was tall and had a body like a Vegas show girl, but her face was plain. I like petite, pretty women. One day she confronted me and all but dared me to fuck her and stop avoiding her. I gave in. In bed she was all delightful surprises. Her big rack was much softer and fuller than I expected, as was her cunt hair. Her pussy was amazingly tight for such a big girl; but her cunt was deep as a well. For my first time ever I was able to get all of my big dick up in a pussy and could bang her crotch HARD. She must have really liked it; she got taunt as a bowstring and I felt her pussy get very, very wet. A few strokes more and she did it again, soaking us both. She had come, twice. The wetness turned me off, actually and I came in her and left. But all these years later, that sympathy fuck still turns me on, and I still jerk off thinking about that deep, tight snatch, sloppy with girl cum, basting my dick and balls. Thank you, Liz!

anonymous readerReport

2011-06-16 10:23:14
A pussy is a pussy. One doesn't fuck the face. Give me a woman or young girl whe likes to have 7 inches in and out of her pussy snd I'm a happy man.

anonymous readerReport

2011-06-15 21:06:27
One night I had three women who shared an apartment. Two were beauties and one was a plain Jane. I'd been out on a date with one of the beauties who brought me home with her. She was sitting on my lap in front of the other two and then said, ''I'm tired. We're going to bed.''. I fucked her brains out. She was an ok fuck. She went to the bathroom and a few minutes later the other beauty came in and got in bed with me. ''Wheeee!!!'' I thought and fucked her brains out, too. She wasn't as good as the first one. She went to the bathroom. A couple of minutes later, the plain Jane came in and got into bed with me. I figured ''Oh, what the fuck. I'll give her a mercy fuck.'' WE FUCKED EACH OTHER'S BRAINS OUT!!! That girl was one hell of a piece of ass. I went back to see her for months and only fucked her. It had to be a hell of a moral booster for her because she knew that she wasn't as pretty as the other two girls. Her self confidence sure improved.

JadeMReport

2011-06-15 06:48:56
Well I guess that question about pity/sympathy fucks was not an idle one! I knew you had done it but did not realize it was the subject of your first story. Congrats on your first story btw.
I am not the best for style/spelling/grammar etc so I will not comment on that.
Keep writing and see what else you come up with! Positive vote

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