35M reminiscing with first time me (26M) with a newbie 21F escrowt

Throwaway.

Was back in grad school, I had just finished a bout of midterms. I was big and fat and hardly ever got any women (im much more in shape now). I had never been raw inside any women before but I was not a virgin.

I decided to rip the bandaid and I heard about the site (bp iykyk) from other online sources. I checked the site around my area and most of the girls looked….. undesirable. Some of them were cute but the prices just scared me away. It was back in 2015 or so, so a few hundred really didnt seem like it back then- I was just looking for something quick so it seemed like a lot. The closest I had ever done to anything paid before that was just a nude massage at someones house- where all I did was just take my hot hard dick and just press it against her pussy to tease her(she said no sex).

I looked online and I saw this page of a beautiful white black haired girl. She had freckles and looked lean. She didnt have her page up for very long. Id been looking for a few days already and hadnt noticed that profile before. I contacted her and set up a meeting. I thought it was low compared to what others were requesting so I decided to try and match the request- “how about a blowjob only for 15 mins?” She said that was fine, and we set up the time.

She arrived at my apartment complex and I was just stunned. Tall, 5’10, with a long sundress on. She looked out of this world. Stuck out like a sore thumb in the living apartment community of college students. I took her up to my apartment while sneaking her into my room from my one roommate, and I was so nervous. I got my BJ and came fast. It was amazing. She swallowed it all too it was so hot. I then sent her on her way and couldnt believe what I had happen. I HAD to see her again so I hit her up the next day at night to come back again for hundrd for 15 mins. I then asked her “….. is it ok if we have sex as well?” She said yes thats fine I guess but condoms are a MUST. i said ok and she came over.

This is where the fun starts. She didnt take off any of her clothes the last time she gave me the BJ, but she immediately got undressed and I saw her lean slender 5’10 body. She had a perky curvy little butt and small lean girl boobs. I asked her if I could video the whole thing too and she said it was fine.

I got on my chair and she starts sucking my cock. Her hair was tied up in a ponytail and you know she was just a pro. I asked her what her story was, how she got on the site. She said she was 21, she just broke up with her boyfriend of 4 years after he cheated on her. She just left his house last night and got a hotel room and started up this whole escorting thing. She said I was the first one she was seeing because everyone else looked kinda gross and a college student felt safe.

I used my hands to guide her back to the side of my bed where she got in doggystyle in standing doggy bent over it. Her butt looked exactly like the peach emoji with how curvy it was, and she had just the ever so slight layer of peach fuzz on it as well. It was so hot.

I immediately took my hard throbbing dick and started teasing her with it, like I did with the first time i saw the massage girl. Her legs were closed tight, so I just pressed up against her wet pussy. She gave off the most newbie vibe, it seemed like she was super down for anything. I dont know what it was but I felt like all inhibitions were out the window. This wasnt an escort to me, this was just a regular normie. I pressed up against her pussy again a second time, and then even harder for a third time.

The third time, I held the pressure for a few seconds, a few more harder, and I heard her make a moaning noise so I just kept up the pressure and it just slid in. Then it just hit my brain with a big dopamine rush. I was completely inside a girl 4 inches taller than me, a solid 8-8.5/10 baddie, completely raw. I immediately started fucking her, and she was wet but not so wet that it lowered friction. She was making noises too and i couldnt believe it. I thought i was just fat and ugly but it seemed like she was really enjoying it. “Whatever happened to CONDOMS ARE A MUST?” I thought in my head with whatever functioning brain cells I had in the moment.

The buildup was insane. I couldnt hold it anymore. I knew how risky it was and I should probably pull out, but I just shot a massive load and filled her all up. And whats crazy, I still kept going fucking her. I was so turned on I stayed hard and she goes “how are you still so hard right now?!” And it was so fucking hot that I immediately came again with another load in about 20 seconds after the first one.

I froze just taking in what had just happened and absorbing the energy of it all and slowly slid out, watching the thick cum slowly slide out in one slowly dripping stretchy mass that was from her pussy to my bed. It was over. It must have been a whole hour not 15 mins. Time just passed by. She put on her clothes and she was on her way out. I had to see her again. She texted me later that night and asked if I came inside her. At this point I was like how could you not know that, lol. But she says “next time cumming in me is not allowed.”

I saw her again the third time, I told her I was going to cum. She keeps bouncing back harder in doggy and I just yell that Im going to cum in her and she just goes “fuck yes please daddy” and I shot a load in her again. Nothing of what she said the prior night stuck. I saw her again, probably up to 20 times or more. No STIs ever, a hundrd each time, with a 5’10 bombshell. Im convinced I exhausted all my luck out of that one. It was still the only time in my life to this day that I ever had a double orgasm. Also the hottest girl I had ever fucked. We eventually get to be friends i got her on social media and everything. I stopped seeing her maybe 8 months in due to boredom. Damn im hard at work now.