In early 2002, I was on a Jewish dating website from which a nice girl contacted me after reading my profile. She was just about to start a lease in a newly constructed apartment building in Chicago. From the picture (of really only her face) on her profile, she didn’t look all that attractive, but not everyone takes great pictures, right? Also, I made it a point never to ignore a woman who takes the initiative to contact me. I hated it when I’d send messages only to be ignored, so I could not do the same to someone who messaged me.
We set up a date for the very evening she would be moving into her new apartment. The plan was to pick her up there and take her out to dinner. When she opened the door I noticed that she did look better than her photo. Not astoundingly so, but better. But now I got to take a look at her body (unseen in the earlier photo). And if I was lukewarm about her face, I was sold by her figure. Not the conventionally sought after physique, but right up my alley. Somewhat tall – maybe 5’6, athletic. Broad shoulders, probably C-cup breasts, and a nice round ass. Her ass was so wide it lent her a pear-shaped figure. Athletic legs and thighs. I distinctly remember thinking, ‘I’m gonna’ lick this girl’s pussy tonight.’
We went out to dinner and had a nice time. In driving her back to her new home, she asked, “Would you like to come up?” “Sure,” I replied. We settled on her new convertible couch, and it didn’t take long before we started hooking up. Things were moving along quickly, and I started fingering her on the couch. When I did this, I was instantly elated because I could feel dense amounts of pubic hair, a feature I always loved on a woman, but as the ’90’s turned into the 2000’s, more and more often I was encountering shaved vaginas.
Once I started fingering her she asked me if I wanted to go to her bedroom. I said I would, and she warned me that her mattress was just delivered today and she hasn’t even put her sheets on it yet. I told her I didn’t care, and we made out way there. As I’m walking there, I’m shedding my shirt and pants. I arrive with her on her bare mattress. She had been disrobing too and all I needed to do was take her underwear off to have her completely naked. I took off my own underwear first in case she would feel more comfortable that way. There was enough ambient light for her to see my fully erect penis staring her int he face when I removed them. She laid on her mattress and I took off her panties. I was greeted with the kind of big, black bush I had come to love. Knowing what I wanted to do and with eagerness for me to do it, she spread her legs revealing a meaty, brownish red pussy. Wasting no time I started eating her out. It was a beautiful sight for a first date, her ample thighs and feet now elevated in the air.
Eventually we got into 69. She was on top, and I did something I had only done to one other female up to that point. I fingered her asshole. Specifically, I put the tip of my pinky in her anus as I licked her clitorus and vaginal opening. She did not move away or ask me to stop. If anything, her breathing quickened and she seemed to have an orgasm after a few minutes.
I was hoping she had one because I sure was about to. She seemed to have a lot of experience giving head. And I was glad because I was more than happy to be the recipient of the awesome skills she had amassed. I started to orgasm and I announced, “I’m gonna’ cum.” She took my penis out of her mouth and stroked me off. Yes, a fair amount of quite a large ejaculation went on my own torso, but it also went on her brand new, bare mattress. Secretly, I got a real kick out of that. Mattress not one day old and already a guy (me!) nutted on it!
Source: reddit.com/r/gonewildstories/comments/m418oe/breaking_in_new_mattress_with_f_who_contacted_me