Tailwind (Love By Design 4)

“Just me back here.” I told her to reassure her. I don’t know what’s made her so nervous after we discussed it, but I don’t like it. I want her to feel comfortable and confident in her body. I want this to feel good for her but it isn’t going to work if she fights me before we’ve even tried anything. I was happy to forgo this and do whatever she liked but I guess a broken condom is like a bad hangover–it takes a little time to get back in the saddle.

“Who else would be back there?” She groaned.

“The boogeyman?” I joked. She doesn’t laugh and I bite my lip trying not to.

“You uh, won’t spit all over me will you?”

“Where’s the confident, no nonsense girl I met in my office weeks ago?” I chuckled reminding her.

“I fainted the first time I met you.”

“I am pretty awesome.” He puffed out his chest. “I meant the woman who walked down Main Street like she owned it.”

“Oh, you mean the one living here under duress and getting dragged about town by three ruffians who smell and shit in the house?”

“See, babe, it’s like we’ve got kids already.” I shrugged to the feel of her pinching my leg. The look over her shoulder isn’t one of bliss and I reminisce how stubborn she can be.

“Ouch, easy tiger.” I removed her fingers rubbing the tips of her short nails.

“She didn’t know she would meet someone who was light years ahead of her wanting things she has no business wanting herself.” Ah, the confession doesn’t surprise me and it saddens me a little. Winnie doesn’t want the things I want, at least not yet she doesn’t which is why she’s up here in the first place pet sitting for the summer.

We met during a crossroad in our respective lives, except I’m open to all the challenges the universe wants to present. Winnie is still fighting back. I want her. I want her to stay. Part of me needs to reaffirm it’s me that she wants and not what she thinks I can do for her. A throwback to the days I thought I would be somebody famous in the spotlight playing Monday night football. Would quiet town life be enough for my city mouse?

I kept kissing her and licking as I go a little farther each time pushing the doubts back. Earlier, I put the lube in a glass of warm water to warm it up before I started squirting it willy-nilly. Obviously, Winnie doesn’t do surprises well. I can’t have her having another freak out.

“You okay?” I asked between kisses and rubs.

“This is like the deep space, the place no man has voyaged to before.” Leave it to Winnie to break up any chance of romance happening right now.

I lift up and speak over her shoulder, “Got it babe, virgin asshole. Roger that.” I take the lube and squirt it on the dimple of her ass above her starred knot letting it dribble down to watch her squirm. I think this part is half the fun, the anticipation of it before it happens, but I doubt she sees it that way. Of course, I’ve never been on the receiving end so I wouldn’t know.

I let my fingers slip down to massage her lips back and forth teasing the hole of her pussy. I press in a fraction feeling her walls clamp down on my finger.

“That’s not–”

I cut her off, “Shush, Winnie. I’m taking my time back here. Don’t expect me to jump right in.” I could jump right in given how sexy hot her backside is and how I want to appreciate every curve but I also know how shy Winnie can be when it comes to something new.

She’s quietly panting, good sounds that I hope I’m reading right. I worked up a steady rhythm pressing my finger in and pulling it out. I drop more lube and slowly spread it listening to her moan and her muscles slowly clench down. I let my finger curve down pressing on the front wall of her pussy teasing her. Once she started to relax I added a second finger and more lube working in and slipping deeper. I want her good and wet, deliriously, so that when I do breach her tight knot she’s so far gone it doesn’t register as anything but pleasant, fun, and shooting her off into orgasmic pleasure.

“Chase.” She wined my name and I watch her hands scrunch up the bed sheets in her fists.

“I love how you feel squeezing tight and pulling me in deeper.” I tell her working my fingers against her soaked flesh with each building moan.

“It feels so good. Right there.” She pressed her hips back seeking more and I let my thumb graze the slit higher up pressing gently.

“Right there?” I asked her pressing with firmer pressure of my thumb in her knot while my fingers continue making a mess of her greedy squelching pussy.

“Mmm Hmm.” Her neck dips down to the bed and I imagined her poor lip being torn up with her teeth from the sounds she’s making.

My thumb continued to press sliding in easier with the lube, her flesh resisting minimally. I stop fingering her and sheath myself with a condom. I did some light reading on the mechanics of this having never done it before. Had no interest in trying it with past girlfriends until now. Once my dick is covered I rub it between her legs catching her wetness and the lube saturating her body.

“Chase,” she growled.

“Easy, Winsome. Easy.” I tell her rubbing my dick against her positioning myself better before pressing the flared head inside her.

“It hurts.” She whimpered, but I keep up the steady pressure because she hasn’t told me to stop yet. I soothe her and rub her side down encouraging her to keep with it.

“What kind of hurt baby?” I asked. I wanted to grip the back of her neck and hold her down in a primal way but kept one hand steady on her hip gripping the sharp jut of her bones.