Tailwind (Love By Design Book 4) Page 12

  “They are cute together.”

  “I’m sorry, is this my girlfriend?”

  “It would seem so.”

  “Okay, don’t defend Damien. You don’t know him well enough.”

  “Sounds reasonable.”

  “Trust me. So tell me why your parents are not there this weekend?”

  “Because my mother got some crazy idea in her head that my dad is still cheating on her so she flipped out when he was fifteen minutes late in downtown traffic and decided to not get in the car with him. Dad got mad and drove to the hospital instead of coming up here by himself. He’s prepping for a residency in Albany.”

  “Ouch.”

  “Yeah, but it’s better than having them here fighting and driving me nuts.”

  “And you’re by yourself.”

  “Are we counting the three souls of Satan?”

  “Generally, no.”

  “Than yes.”

  “I’m sorry, Win. I really wish you were here.”

  “Me too but you come home soon. I can deal with it.”

  “Yeah but I can’t.” Chase whined.

  “So no tattoo for you?”

  “Not this time. Someone had to make sure boy wonder and the crew made it back to the room without a tiger or a mob hit.”

  “You know, that would be funny if it wasn’t partially possible.”

  “See, you know Damien after all, I swear that movie the Hangover was written after his shenanigans.”

  “No, I meant your sister. She’s been texting me all weekend and it sounds like trouble.”

  “Do I want to know?” Chased groaned and the sexy sound set my core to quivering and my needs to immediate. My hands were going to busy doing more than just texting the next few days.

  “Nope.” I popped the p saying I this time.

  “You’d need more than just bleach for your eyes.”

  “Alright, I’ll pass then.”

  “Good decision.”

  “So when I get back, I’m coming straight over.”

  “Are you warning me, or telling me?”

  “I was thinking there was nothing wrong with being prepared.”

  “Hmm, I’ll take that under advisement.”

  “Excellent.”

  I hung up the phone feeling lighter than I had in days since Chase had left. My parents might have let me down but he was doing everything he could to make it up to me and make me feel better. It worked. I couldn’t wait for him to get back. I might even stop by the Vodka and Wash salon for a little pampering so long as I had the cash on my debit card. Chase Calloway was worth the good waxing.

  23

  Chase

  “So remember when you said anal?” I strolled into the bedroom watching my girlfriend lay on the bed reading a book wearing a pair of cotton lacy bottoms that gave her endless legs and a tank top that let her small breasts sag gently into the bedding. She was definitely my girlfriend now. I claimed her and all but peed on her leg marking her as mine. I was kinky, but I wasn’t disgusting.

  She peered up from the pages biting her bottom lip, cheeks blushing as if I caught her reading something she shouldn’t. Heck, if she was reading something romance-y maybe it would get her in the mood.

  “Uh? I said that? I don’t think I said that.” Winnie shook her head closing the book and tossing it onto the nightstand. She knew as well as I did she said it and now I’m here to take her up on her offer. Willingly of course.

  I tapped her calf nudging her to move over and make room for me on the bed. Sweet Winsome liked to starfish my bed, but I was in charge in here. “Roll over sweet cheeks.” I tapped her ass with my hand in a gentle swat.

  “Sweet cheeks is it?” She looked royally put out, not that I could blame her. It’s not every day one takes it for the proverbial team but I think Winnie could at least try to expand her horizons a little bit beyond her trust fund and citified ideas. It doesn’t hurt that I think she’s hot as fuck and who wouldn’t want to plow her gorgeous behind. Thinking about it made me wince. I didn’t want any other guy thinking about it. Just me.

  I exhaled a deep breath touching her body that seemed stiff as board right now. “Personally I’d go with candy ass but since I plan on pounding it I settled on sweet cheeks. I figured it was less offensive.” I moved her onto her belly taking her panties off as she turned.

  “Less offensive?” The glare she gave me over her shoulder would be etched into my mind forever. It was the glare that dared me to do this while saying I was going to owe her more than a nice dinner after this.

  “I did buy the good lube.”

  “So there’s a shitty lube I should be concerned about?’

  I shrugged. “If it makes you feel better.”

  “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.

  “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.

  “A good hurt.” She surprised me leaning back into me. There’s my brave girl and I pressed forward slowly and retreat slightly. My hands massaged the soft skin of her flanks encouraging her.

  “Better?”

  “Don’t stop.” Once I’m in partially and have traction to move a little my hands wander her body caressing her, calming her. My fingers resume playing with her clit and one finger enters her slowly.

  Winnie moved, attempting to get closer to me rocking on her heels and stretching out her lovely back.

  “Good girl.” I praised s
toking her. I give her what she needs as I finally bottom out inside her ass and my balls slap her clit from below.

  “Oh Chase.” Her moan echoed in the bedroom and I moved more meeting her thrust for thrust. Every part of her was in sync with me squeezing and begging for more.

  “Winnie, I’m going to come.” Grunting I’m there already pulsing, my eyes feeling a dark haze come over my vision.

  “I’m coming.” She shouted back and I let go jetting inside the condom and stroking her orgasm out.

  We rolled to the side on the bed and I hold her spooning still inside her feeling every little twitch of her body out of breath with mine.

  “That was…” Her voice trailed off a little sleepy sounding.

  “Awesome?” I cued her.

  “I was going to say not half bad.” She mumbled into the pillow and I tickled her ribs.

  “Not half bad?” I growled nipping at her.

  “Sorry, I’m a terrible loser.”

  “Well, then, I guess we’ll have to try that again.” I tell her kissing away further protests.

  Not half bad she says…

  Women.

  Pfft.

  24

  Winnie

  I might be addicted to butt sex, but damn if I’ll ever admit that to Chase. He’s spooning me and I’m too exhausted to care about how sticky weird I feel because I’m floating in a blissful state of post sexual happiness. It was better than ice cream, shoe shopping and the theater on Broadway wrapped into one. Okay, maybe it wasn’t totally all those things, I mean seeing the original cast of Evan Hansen on Broadway was exceptional, but my irrational fears aside it really was good sex. I might have to look up the equivalent for guys because I honestly think straight guys might be missing out on something here.

  “Let me take care of this.” Chase eased out from under me and slipped inside the bathroom to dispose of the condom. He came back with a towel and starts peeling my legs apart.

  “Hey, hey, hey!” I tried slapping his hands away but he’s bigger, stronger, and apparently bossier now that we’ve done this his way. I think I mistakenly unleashed a dominant freak. He holds my wrists firmly and goes about his business. He’s become some kind of alpha-dog but if he tries urinating next to mark his territory I’ll punch him.