Tailwind (Love By Design 4)

“Loads better.” She said sarcastically and the itch to tap her ass with my hand skirted in my mind. I really, really liked this girl.

“Come on, babe.”

“Hey, wait! Whoa! Are you sure I can’t get pregnant this way?” She batted my hands away playfully. The tremble in her voice was adorable. She can’t be serious about the pregnancy thing though. We were adults and I’m sure she’s had a thorough sex education by now. You couldn’t possibly get to your twenties without this knowledge. She lived in NYC where live was fast paced and Planned Parenthood had a firm stronghold on contraceptive education, ,or at least the last time I checked. If not, I was more than willing to educate her with a live demonstration.

“Pretty sure.” I said ready to play this out to the wicked end. “I consulted with a few other doctors I know and there’s no way an anaconda up the butt is going to knock you up sweet cheeks.”

“An anaconda?” She was gullible and I loved that about her. It was hard to hold back my laugh.

“Yeah, you know, the man snake.” I tried to play it off but she caught me. I was in so much trouble now.

“You’re a veterinarian!” She shrieked trying to crawl off the bed before I caught her ankle and settled her over my lap spanking her ass twice for good measure.

“Damn right I am, now hold still.” I said caressing the warm pink skin of her butt that now sported my handprint. I never thought I would like something like that but I did. I probably liked it far more than I should.

Winnie stopped struggling but her warm soft belly pressed over my dick was distracting at best. I could feel myself rubbing against her leaking a bit of moisture and lifted my hips up and grind against her.

“I’m not sure about this.”

“Win, I’m absolutely certain anal sex can’t get you pregnant no matter what species of mammal one happens to be.” Now we were arguing in a circle of non-logic.

“I don’t think this position is going to work.” She grunted trying to turn over but I didn’t let her, instead my fingers traveled to her ass caressing and slipping between her silky thighs.

“I think m’lady doth protest too much”

She moaned as my finger traced up and down her slit spreading her wetness around. “If you start playing that Animal song, I will punch you in the dick so hard you won’t be able to get a girl pregnant ten years from now.” She was huffing and wiggling which didn’t make the position we were in any easier on me let alone what I planned to do to her in the next few minutes that had me rock hard.

“Relax, there’s a whole protocol to work up to before I slip inside this tight little star.” I let my thumb graze the cleft of her ass circling the bud. Her whole body contracted and I took it as a good sign she hadn’t bucked and thrown herself to the floor.

“I don’t know if I can relax.”

“Do you want music playing?” We didn’t have to do this but I figured if regular sex was off the table we could try something else. Apparently she’s worked up in her mind a host of things that go wrong with anal sex and so far I haven’t been reassuring.

Go me.

Boyfriend of the year.

“Very funny, Dr. Calloway.”

“I’ll get you there Winsome.” I lean over her pressing h

er deeper into my lap. I kissed her shoulder. “Promise. Do you trust me?”

“Y-yes.” She huffed making her sound like a disgruntled kitten.

“Then be a good girl.” I shifted myself so Winnie was on the bed propping her up on her hands and knees. She looked over her shoulder at me, her dark eyes pleading and brow furrowed. I promised to give her pleasure before I get anywhere near her rear and I planned to deliver.

“What if your baby stuff, um, you know, leaks down?” I fight to roll my eyes with my dick so hard and straining against the fabric of my pants at the naïve question. I know she’s not serious, but the way she nibbles her bottom lip and her cheeks pink, this is more about her fears.

“I’m going to wear a condom and use plenty of lube. Winnie, I would never make you do something you’re uncomfortable with. If at any time you want me to stop, tell me and I will.”

“Promise?”

“Always, sweetheart.” I pushed her shoulders down on the bed hearing her grunt. I stuffed a pillow under her to keep her in a better position.

I hoped this was temporary. I was all for trying out new experiences but I had my reservations. I wasn’t going to tell her about the research I did online or discreetly at the book store in the human sexuality section. I’d gotten enough stares in Kingston praying no one recognized me there. I’m sure there were plenty of porn sites I could have scoured but I wasn’t looking to perv out on this, I wanted to find something that would both bring us pleasure and keep Winnie from freaking out about babies and commitments lasting longer than summer. Yeah, if I was honest with myself I think that part bothered me te most.

My hand reached up and felt her spine, so delicate under her honey colored skin. I leaned over to kiss each ridge of her back peppering the notches of her vertebrae with my lips. My tongue followed making a wet path down to the top of her ass. Her whole body shook and I caressed her to calm her down.