Chicago (GXG)

Part 28

"Alright, how about you lay on your stomach first?" I guided her. I don't want to go in cold so I'll eat it first, then insert the toy. Damn I'm smart.
"Sure." She said as she adjusted herself around and made herself comfortable.

She is now laying on her stomach with some pillows under her head and her hands are hugging them tight. "You a little nervous there?" I asked and laughed at how stiff she looks.
She smacks me with one of her feet somehow and tells me to stop teasing her as she's already feeling embarrased enough.

"I've never done this, of course I'm going to be a little on edge." She sighs. "What if something goes wrong? I cleaned myself but there could still be a risk for some unpleasant things..." She rambled on and on. "Look, I know the risks but I'm down for all of it to be honest. Let's just be mature and accept that if something happens then we can deal with it, alright?" I assured her.

Her body language loosens up quite a bit and she no longer seems as insecure, which is a good sign. I'll take that as a hint to get to business.
I lowered myself from my previous sitting position so that my face is closer to her hips. I start kissing her lower back and eventually making my way onto her buttocks.

I take my sweet time kissing on them before moving into anywhere deeper, just to get her accustomed to the idea first.
I take my right hand and grap her right cheek thouroughly, spreading it so that I can see what awaits me. She really is beautiful all over, somehow.

My kisses and wandering tongue slowly make their way down the inside of the cheek, creeping closer and closer. Val's body is still somewhat unsure, stiffing as I get near to my goal.

I understand why she would be insecure about this, it's not really something that many people would do. Most people actually make fun of this stuff anyways, but oh well. Their loss.

I'll try to make my girlfriend feel as comfortable as possible, I lightly kiss the opening. She takes a deep breath, accepting that this is happening now.
I switch to using my tongue and I swirl it around and around, pushing it slightly inside and around the entrance.

Her body seems to be responding, but obviously not as much as it does to normal head. Her breathing is deeper and she keeps pushing her behind toward my face, asking for more.
She's clearly enjoying this so I'll continue for a while more before I switch to other things. I run out of things to do so I just trace the alphabet with my tongue, but eventually I run out of letters.

That's when I decide to introduce a little something else. I take a bit of the lube with my index finger and rub it on her hole, making what I'm asking for obvious to her.
She doesn't protest, so I take that as a sign to keep at it. I do circles around it for a while before I apply pressure to push it in.

She moans a little as it goes inside, up to the halfway point of my finger. I hold it still for a while to give her some time to adjust before I begin to wiggle it ever so slightly.
I massage the inside walls and then thrust it in a bit deeper until my whole finger is in. She is moaning a bit but shows no sign of pain or discomfort, that's good.

"Does it hurt?" I ask her to be sure. I move it around inside of her and she arches her back to make it easier for me. "Does it look like I'm in pain?" She asks me teasingly. This lady I swear, so much pride. I love her though.

"Well if this is so painless and boring, should be move on to the plug thingy?" I suggest. She laughs and gets into doggy position.
"What are you waiting for then?" She says.

I remove my finger carefully before reaching for the toy that's on the bed. I apply a hefty layer of lube on it, drowning it. Spread her cheeks roughly and tease her hole with the tip of it.
"Prepare yourself then, alright?" I say quickly. I feel so out of breath and my mouth is dry.
I always get so nervous and excited when we have sex, but in hindsight that's a good thing.