During my single days, I met a girl that was cute, really quiet, but was easy to get into bed.
We had met on pub crawl, and she was my kryptonite: a red head. She was barely 5’0″, had great tits, and was just chubby enough to be self-conscientious about it. For date #2 I suggested a movie at her place, and brought the DVD (this was before netflix).
Since we made-out on the night we met, things progressed pretty quickly. I was a sucker for a sure thing, so we ended-up seeing each other a few times a week for the next couple of months.
The sex wasn’t great, but regular sex is still good. Often it would be some hand stuff, I would go down on her, then missionary, and sometimes she would ride me cowgirl. The freakiest thing about her was that she always insisted I finish inside her.
She wore the birth control patch, and said that feeling a man fill her with his cum made her feel like a woman. Whatever, I dumped in her every time.
One night, I asked about getting head, as she never once did it, or even tried. She said she didn’t like to do it, but would try if I really wanted. The effort was awful. Teeth scraped, and the lack of enthusiasm all but killed my erection.
One night, after being at the bar, we got back to her place. She star-fished on the bed while I was in the bathroom, down to the lavender panties she had been wearing.
I crawled on top of her and started kissing her neck, and she moaned. She lifted her hips as I pulled her panties down over her ass, and started rubbing my cock against her ass cheeks. We had never done doggy style, so I was going for it.
I pulled her ass towards me as a I spread her legs a bit. I was horny and drunk, and she was very drunk, so I just wanted to fuck. Without foreplay, it was tough going, until she reached for the lube in her night stand. With a good coating, I was slipping right in her.
Her normally quiet self started moaning and gasping, and I felt her fingers brush my sack as she played with herself, which was totally new.
Being just inebriated enough, I was going to town. Her unusual openness to new things had me pushing the limits. I pulled her hair, smacked her ass, lightly choked… she loved it all.
I decided to go for it all. First, I pressed my thumb into her ass. She pushed back, and looked back, but went with it. A few minutes of this, and I wanted to be balls deep in her shitter.
Grabbing the lube again, I squirted her ass crack, and then started to push the head of my cock against her asshole.
“What are you doing?”
“You always ask if I’m happy with our sex, This is what I want tonight, this is will make me happy.”
“Okay, but go slow. You’re big.”
(I’m not that big, in fact I’m text book average, but I love when women say that.)
For as much as I wanted to pound her ass, I went slow. First the head, then a bit more. No thrusting, just a constant push. Her sphincter loosened, and I started sliding in more.
“Ugh – your ass feels so tight. You feel so good.”
“You make me happy, I want to make you happy. Are you turned on doing my butt?” (She didn’t curse, and this was about as dirty as it got.)
“Fill me. Fill me with you cum. You know how it makes me feel.”
Thinking about cream pieing her back door did it for me, and I finished. She jerked away after I bucked a little aggressively, but that created a lube/cum goo string that stretch from my dick to her ass. I loved it.
We dated another week or two, but it ended. The sex wasn’t bad, but taking her anal virginity was the best part for me.
Source: reddit.com/r/gonewildstories/comments/6fh479/mf_getting_her_out_of_her_shell