Being in an open relationship with my girlfriend definitely has its perks, like being able to sleep with a much younger girl that works in the same building I do.
Cassie looks like a typical office/front desk employee. But under the prim and proper work exterior a hard-partying, tattooed rocker girl (with one or two daddy issues) is hidden.
When I hooked up with her for the first time Cassie summarily denied anal. With a little bit of convincing every now and then however I convinced her to work up to it however.
It took some doing getting her ready. Playing with her lovely, perky bottom is definitely something I looked forward to. So after a period of careful preparation the day had come.
We met for dinner after work. And while Cassie normally is a hard drinker too, I could tell by the way she nursing her drink and looking uncharacteristically insecure, that she was nervous.
So when we were back at my and my girlfriend’s place, (She was out of town for work) I decided to be more gentle with Cassie. Normally she likes it at least a little rough, but I think the prospect of taking it up her other hole had nerves in disarray enough.
So we took a seat on the bed and I kissed her. Laying her down on the bed gently and slowly pushing a hand under her skirt and starting to rub her through her panties.
She enjoyed that and relaxed, while shivering in anticipation of me going further. Taking that as a sign I started taking of her clothes, revealing her ink. Which is a spectacular sight again and again. Owing to the contrast of her looking like a business woman, when clothed for work and like the slutty vixen she is without.
I kept warming her up by licking her lower lips and clit, interspersing that with sucking and slight biting and then going further, when she started to get wet, by inserting my thumb in her pussy.
When I had her moaning and aroused, I gently inserted my middle finger in her especially for the occasion cleaned rear. I kept playing with her pussy and took my time to make the sensation for her feel pleasurable.
However I did want some attention too. So I got on top of her and we 69ed, while I kept playing with her pussy and ass she expertly sucked my dick. With all the preliminary work Cassie just started shivering and came, from all the attention I had given her.
After a while we moved on and Cassie got on all fours. So while I started to fuck her pussy from behind and I kept inserting my fingers in her other hole. Slowly increasing how much I stretched her other entrance.
I kept fucking her within reach of another orgasm before I stopped. I had Cassie lay down on her side and then got behind her in a spooning position. I slowly started to insert my cock into her ass.
I kept reaching around though, stimulating her intimate areas. Cassie actually teared up a little and whimpered in pain. But that actually was replaced by moans of ecstasy and pleasure. As she had been shortly before reaching a climax, me playing with her front side, actually sent her over the edge.
The feeling of pleasure overrode the feeling of pain. Once I had worked my way fully into her I took up speed, but never kept letting up on pleasuring her pussy and clit too.
Experiencing orgasms like that definitely made her appreciate anal. We moved on to doggystyle and variations of cowgirl and missionary positions. And Cassie had the fuck of her life, like that. (Her words not mine.)
I reached my limit too however after keeping up a steady fucking. So I shot my load inside her ass and pulled out saying goodbye for now to the tightness of her perky, not virgin anymore, ass.
After enjoying herself a lot, she was eager to repeat the experience in the foreseeable future.
Source: reddit.com/r/gonewildstories/comments/a8g0ts/first_anal_for_my_young_lover_mf