Growing up I was never the most social person. I have always struggled with finding common things to talk about with women and until nerds got cool, I really never thought I would ever be able to find common ground with girls. I hate dancing, I really could care less about music and tv shows? Please. TV is nothing I care about (unless its Game of Thrones, or Rick and Morty). Never have. I do not have things in common with your standard, “OMG, who is going to be the next American Idol or Bachelorette” Who cares. That’s always been me.
That doesn’t mean that I don’t want to fuck the girl next store, or the really hot 20-year old that brings me my food at my favorite restaurant. One of the rules of life, servers fuck servers. If you are in the food industry, there is a very good chance you have gone out, gotten drunk after work and fucked a co-worker. It’s literally what they do. I am a millionaire nerd, I have never worked a real day in my life, I can play a good poker game, but that gets me the girl. I love a good meal and when there is a cute girl, I leave a good tip, and they get flirty with guys who leave good tips, but let me tell you, it almost never brings home the girl.
Success-oriented people don’t like to take no for an answer. I am not suggesting a lack of consent, I am merely suggesting that we try again. Get rejected once, try harder. That’s been my approach and sometimes with the timing is right good things happen. You never know what is going on in a woman’s life, while today you might have no chance with her, the right moment, the right situation, things can change. If I had a nickel for every time a girl said she’d NEVER sleep with me, Id have 35 cents at least. Things change.
That said, it’s still really hard to get your server. They don’t want you, but they do want your money and being a server is hard work. Every server has a price, it’s just a matter of how much you are willing to pay.
$1000.00. At least 10 years ago, that was the magic price. For $1000 dollars you can get a server to do whatever you want and that was basically how the conversation started.
I simply have to have you. Go ahead, name your price…. 300? 500? 1000? “1000?!… yeah, I will fuck you today for 1000” Ok, come over, but I do love anal.
We had already discussed sex numerous times, as I had been hitting on her for weeks. She claimed to hate sucking dick but was totally down for anal. Even told me, it stimulates her G-spot or something like that. She was 95 pounds, with the cutest set of tats on her sides. She claimed to be a model, but really it was an excuse for guys to take naked photos of her. Anyways, I eagerly awaited her arrival at my house. She was greeted by me, already wet as if she had come from a shower directly. I took her upstairs and the fun began.
No oral… that’s the only rule. Oral isn’t that important to me. We kiss and she bites a lot, she loved to bite the lip, which annoys me a bit, but it’s all good little sweetie, my thick cock is going to be in that ass soon. I slowly strip her down as we make out. I mean, I love to enjoy the suspense and she finally gets a sense of what I am packing. Most guys, you can get away with being a cocky bitch that loves your ass stimulated, but with me, you better be able to take a big dick. A lot of girls cant, but those that can — well they are the best.
With her clothes off, and the biting annoying me, I put her doggy position and began to fuck her. Her pussy felt amazing, I totally loved her pussy, it was tight, and she sounded so sweet. The sounds a woman makes when you fuck her is special and she was proving to be a good fuck. She loved my cock inside her pussy, it was hitting all the right spots and I could tell that I was going to impress this one…. In my young days, I was able to switch positions and bring a lot of stamina… we fucked doggy, then missionary, then I let her ride me a bit, but now it was time for the main event.
I lubed her ass up and got ready to penetrate… she jumped.
“Whoa.. you know, maybe I shouldn’t do anal today.. Ya know how about another time.”
I reached for my drawer and grabbed a stack of $20s… 1000 worth and put it on the bed, let her touch and went.. this is what you are fucking for…
I grabbed her ass again, and put my cock inside of her ass. This time, no complaints, no hesitation, she began to get fucked in the ass by my cock and it felt great. I totally loved using her anus to be my perfect toy and she didn’t like being my perfect toy, it hurt. She decided to propose something I have never done before….
“Let me ride it with my ass”
To this date, she is the only person I have ever fucked that has ridden my cock using her ass. She popped that cock right in her ass and began to fuck herself with it, riding it up and down. In some ways this was better because I could now see her gorgeous face in a bit of pain, I played with her tits, which were very flat, but still, I admired her body, but I couldn’t help but think, damn, I should get tested after this, I am really surprised this girl is riding my dick wiht her ass.
Then she decided to cheat. She took my dick and changed holes. I was now in her pussy and she was fucking her pussy hard. To be honest, her pussy felt better than her ass, though I lost the great look on her face, she is now fucking my cock hard and enjoying it again, but I laid there more puzzled but how dirty this slut is changing holes than anything else. You see, I am not allowed to cum in her pussy and that was the one thing she made clear was important, but she didnt my cock in her ass either.. so we rolled with this and she took charge, fucking away. When I got closer to cumming, I told her I am about to cum….
but I wasn’t quite there yet, I just wanted to see her fuck her ass again and she did. All and all, we must have fucked about 30-45 minutes as I made sure to get good use of her asshole for my money. Eventually, I did cum inside her ass, as planned. It was a great fuck for me and well worth my cash, the hot server becoming my anal whore… there is not much better than that.
Sadly, she never returned again. Though she did get another $1000 a few months later by promising that she needed the money and she will come back and fuck me as she had moved to a different city, only to never come back and see me again. I am not sure why she never did, I really thought I did a great job with her pussy but she did later confide that she held back tears when getting fucked in the ass by me. That I was only her second partner in the ass and it was too much for her. Who knows if its true or not, but this was one of those times that I truly think my $1000 was well spent, however, the second $1000 was a lesson to never pay someone for sex unless they are there to give it you on the spot.
Last Updated on 2 years by pseudonymous