“Thank you for dinner” Kaitlyn said with a smile as she dabbed her napkin on the corners of her mouth.
“It was my pleasure”, I said semi-jokingly.
Honestly, I didn’t have much choice. We work for competing law firms. We’ve known each other since high school, continued as classmates through college and it wasn’t until after college that our lives had split. I went to Grover and McClintock while Kaitlyn went to Jones and Smith. It seems the only time I ever see her now is when we are opposing cases and that’s how we ended up here. Since we’ve known each other for so long, there’s been a lot of competition.
“A pleasure?” she said. “You got your ass kicked”.
“I gave you this win” I said. No, I didn’t give her the win, I really got my ass kicked.
“Riiiiiight” she said in a drawn out tone.
There was no way I was going to win the case nor did I want to. I was defending someone guiltier than sin. Usually, I’m good at my job, but my heart wasn’t in it. He was a real asshole, he deserved his sentence and I won’t be losing any sleep over this loss. Speaking of sin, her eyes and her eyes leave my gaze and move toward to a server has he walks by. My eyes glance down at her cleavage and I feel a slight tingle in my groin.
“Hey!” she says as she finishes the last few sips of her wine.
Shit! She caught me. My eyes move back up to her eyes and I feel my cheeks run hot. She smiles coyly and I pretend nothing happened.
“I do need to get going though, I have an early morning.” Kaitlyn says as she stands up and starts to walk off.
Her loose red skirt comes to just below her knees. Again, my eyes drop down and I glance down at her perfectly shaped calves and bright red high heels. Her skirt twists as I see her make a quick turn.
“Hey!” I hear.
Dammit, I did it again!
“Are you coming or not?”
“Yea” I reply.I finish the last sip of my Old Fashioned. God that’s too sweet, I think to myself and get out of my seat.
I take a few rushed steps to catch up with her and I feel my arm hair light graze her arm. My arm hair raises with a tingle that almost feels like static electricity. That was an accident and I hope she didn’t notice.
“Did you take an Uber here?” I asked, knowing the answer.
“I did, did you want to wait with me?”
“Naw,, but I can just drop you off if you want”.
I watch her eyes look up for a split second as if she were contemplating my offer.
“Sure” she finally replied.
I hold the left side of the green double doors open for her at the front of the restaurant and emerge onto the sidewalk. The parking spots at against the curb were completely open as she glances to see where my car was parked.
“I parked in the back” I answered as if I had her mind. I briefly place my hand on the small of her back as if to say, “let’s get going”.
She begins to walk just a few steps ahead of me and as she nears the corner her heel gets caught where concrete and the asphalt meet.It snaps and she quickly falls to the ground.
“Goddamnit!” she says as she starts to lift herself up, I offer her a hand which she quickly grabs. After returning to her, she bends her right leg back at the knee and pulls her shoe off, then bends at her left knee and removes her other shoe.
“Do you mind?” She asks.
“Mind if what?” I responded, but it was too late, she was already behind with her arms coming up between my arms and by upper body and she jumps wrapping her legs around my waist.
“Every time I walk on gravel it hurts my feet”, she playfully whimpers into my left ear.
Her shoes dangle near my right eye as she holds them in her hand.
I feel her breasts push into my back as I begin walking back to my car. The speed of which she jumped on my back happened so quickly that just I then realized that my hands were holding her up by her now exposed thighs. My pulse quickens and I feel a tingle again in my groin at this realization.
I bend at the knees and slowly ease her off my back as we stop at the passenger door of my car.
I reach into my front right pocket to retrieve my keys, unlock her door and pull the door open for her. She shifts her shoes to her left hand and slides her right hand against the small of my back then moves to the arm rest and eases herself down into the passenger seat. I glance down at her now exposed thighs and tingle at the realization of where my hands had been and how nice her legs look.
We’ve always had a level of sexual tension, but neither one of us had done anything about it in all this time.However, In my private time, I’ve often wondered how sex with Kaitlyn would be and now, I have new pictures that I can bring into my mind while I take my imagination into my own hands.
I open the drivers door and sit down only to realize that penis has started to harden at the thought of masturbating as soon as I walk back into my house.
“Dinner was good” I said, as I try to take my mind off my discomfort. I glance over seeing that she still hadn’t flattened her skirt out and her thighs were still exposed.
Another tingle. “Dammit man, get with it” I think to myself trying not to make things more embarrassing for myself.
The drive back to her place felt awkward, I tried convincing myself otherwise, but every time I felt like I was in control of my horny mind, I would notice another detail. Our arms lightly touching as I reposition myself to look through the back window or seeing the goosebumps on her thighs from the cool breeze from the air conditioner.
Instinctively, I adjust the vent control so it’s only blowing at our faces. I blush again when as I wonder if she realized that I noticed her goosebumps.
15 minutes later I pull up to her apartment.
I exit, walk around and open her door.
“As always, it was good seeing you”. I reach out and give her a quick hug.
“Not so fast” she responds.
Nervously, I look inter her eyes. “what?” I ask.
“I’m not walking up the stairs, you’re going to need to carry me again.”
My heart rate increases when I realize how close we are going to be again and being able to think about it before it happened made things so much more uncomfortable.
Bending at the knees I offer her another piggy back ride. This time, being more mindful of where I hands are, I hold her up from right behind her knees.
“Good”, I think to myself, “much less inappropriate”.
Sometimes, it’s hard to distinguish between innocence or flirtation. Like, does her heel press against my groin on purpose? or is it entirely done in innocence and a result of the awkward manner of which we’re walking. Does she NEED to press her tits against my back? Is she really rocking her crotch against my back or is it just the way she’s being held?
“Thank God”, I think to myself as we finally get to her door. Two flights of stairs just breezed by and it seems like I got here in no time. “I can’t wait to get home”.
For the last time in the night, I bend my knees and help her down off my back. We turn towards each other and I reach out to give her one final hug for the night. As we press against each other, I realize my semi-erect penis is pressing into her groin.
“Damn” I think so myself, hoping she doesn’t notice anything.
“Let’s do dinner again soon” I finally choke out
“Don’t you want to come inside” Kaitlyn responds.
“I thought you had an early day tomorrow” I responded.
“I do, but I would really like some hot chocolate before bed” she says.
Hot chocolate, that does sound good.
“Alright” I respond.
She reaches into her purse and pulls out the key, puts it into locks and slowly turns the key. More tingles? Jesus, even the thought of her putting a key into the lock is turning me on? I really need to get home. Sometimes having a dick sucks.
I sit on her couch as she goes into the kitchen to prepare our hot chocolate. I feel antsy, I want to jerk off, but it’s not like I’m going to say, “No, I can’t come in because I need to jerk off.” That would make things so much more awkward. After sitting alone in silence for a few minutes, she comes over, hands me a much with this minty smelling cocoa.
I take a small sip.
“Wow, that’s delicious. What is it?” I ask.
She giggles and says “Swiss Miss….”
I raise an eyebrow.
“With a healthy amount of peppermint schnapps.”
Ahh, that explains the mint, I think to myself.
“What are you trying to do, get me drunk?” I ask.
“No, it’s to loosen you up. You’ve been pretty uptight today, especially after dinner.”
Fuck, I think to myself. Has she noticed?
We make small talk about nothing of substance until I finish the last sip of cocoa. I lean forward to set the mug down on the coffee table. As soon as the clank of porcelain touching glass happens, Kaitlyn gets up and stands between me and the table. She lifts the front of her skirt and sits down on top of me. I could have sworn in that quick glimpse that she wasn’t wearing any panties.
“What?” I think to myself. “We’ve never done anything like this, is this really happening?”
I lean into the back of the sofa, with her knees on either side of my thighs, the full weight of her crotch pushing into my now fully erect cock, she reaches up, putting her hands on either side of my face, leans in and kisses me deeply. I wrap my left arm around her placing my hand on the small of her back, my right hand on the nape of her neck and I pull in her tightly. Out tongues dance together in ecstasy. I can feel her pulse throbbing against my penis.
“Looks like I’m not jerking off tonight,” I gasp.
“What?” she pulls back and gives me a puzzled look.
Realizing I actually said this out loud I laugh and say, “oh nothing” as I bring her in for another kiss.
She reaches down unhooks my slacks and slowly unzips my pants reaching down farther, she grabs my penis and pulls it through the fly of my boxers. We kiss again deeply as her wetness starts running up and down the length of my cock.
“This is unreal”, I say and she smiles in return.
I begin to untuck her blouse and unbutton it starting at the top. After the last button I toss her shirt aside.
“Oh my God,” I think to myself seeing her tits spilling out of her bra. I’ve caught glances at her cleavage, but never this.” How was she able to button the shirt in the first place,” I begin to wonder.
She stands up and I feel a cool breeze over my penis covered in her wetness, she unzips the back of her skirt causing it to fall down to her ankles. I look her over, taking her in. You never truly know what to expect until it’s there in front of you. She’s…..fucking perfect.
She eases herself down so she is lying on the couch with her legs spread open. Her pussy looks magical as it glistens in the light. She tilts her head down slightly and looks deeply into my eyes and a slight smile comes across her lips, she lifts a finger and starts motioning me toward her. As I crawl my way up between her legs having one thing in mind, she grabs my head with both hands and brings my mouth down to meet her.
Her taste is exquisite. The tip of my tongue runs up and down her slit lightly a few times and the urge overtakes me. I need more. I watch my thumbs start rubbing on either side of her clit before I open her up wider. I slide my middle finger inside of her and start rubbing against the front wall of her vagina while dragging the length of my tongue over her clitoris. Over and over, over and over I feel her body tense as I quicken my pace. She wraps her legs around my head as she pulls me closer. Her muscles tense tighter and tighter until I feel her muscles relax. At this moment, I feel her pussy clinching around my finger as her clitoris starts to throb. I wrap my lips around it and begin sucking her into my mouth with every contraction then flick the tip of my tongue over it every time it comes into my mouth.
We make eye contact with her as a smile comes across her mouth.
I raise myself up ready to enter her as she also starts changing her position. I watch her as she turns around onto her knees and presses her chest down into the sofa cushion.
I can see some of her juices dripping down her inner thigh. My eyes run up her pussy to her ass and finally to her back, I notice the light hairs standing up in goosebumps.
I position myself behind her looking her over at this sexy angle.
I wet the head of my cock by gliding it over her entrance.
“Please,” I hear her moan.
I push the head of my penis inside reach up to grab her this and in one slow trust I bury myself deep inside her sliding my head against the back wall of her vagina until I feel myself rest against her cervix. I hold myself there catching my breath. We fit together perfectly.
My hands tighten on her hips and I begin thrusting myself in and out leaving just the tip in her as I push myself back into her.
The smell of our sex fills the room as I continue thrusting into her. I notice a bead of sweat run down the center of her back and she starts pushing back into me, matching every thrust. My testicles slap against her clit in every thrust. My penis clinches as I pull her back onto me and hold her there. I start thinking about ANYTHING other than this, I don’t want to finish yet. I run my hands up and down her back and feel a tickle in my balls. She ungulates causing a light throbbing sensation in my penis. I relax myself and feel my pre-cum running up the shaft and out the head. I can’t tell what is making her more slippery, her juices or mine.
When I’m ready I reach down and put my hands over her breasts, pulling her up. My chest pushes itself into her back as I start begin rocking my pelvis. The head of my cock again starts applying pressure to the front walls of her vagina once again. Our pace quickens as I slide into her, over and over over and over until I can’t take anymore. I try to regain composure by pushing myself deep inside her. I think it did it in time, until I feel herself clinch down on my cock, tighter and tighter until it feels like I can’t even pull out if I wanted to. My penis tightens and I feel my testicles pull tight against me which causes my penis to expand making her tighter around me. I can’t help but push in deeper.
“Unnnngh” she moans aloud as I feel her muscles relax again. Her contractions begin milking my penis. I tighten as she squeezes tighter and tighter every time she contracts. Knowing that there isn’t much more I can do to prolong the experience I push in as deep as I can squeezing her tits as I relax into her I start feel my cum tickling my shaft until I can no longer control it. Every pulsation of my penis causes her to clinch down around me. I put my hand on her face and turn her toward me. We stare into each other’s eyes as our orgasms subside. I can still feel the heartbeat in her pussy as I finally pull myself out. Our combined juices run down our legs as I collapse down along side each other. She leans in to kiss me as she whispers, “maybe I’ll just call in sick so we can do this again in the morning”.