Working in Real Estate part 21 [M35/F30] [fiction] [penetration] [oral] [riding]

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I arrived at Kayli’s house on Friday night shortly before seven PM, willing and excited for our first official date since she had separated from her husband. Knocking on the door, I smoothed out my shirt, holding out the bouquet of flowers I had gotten her as she opened the door. When she did, the five foot tall, black haired real estate agent gasped in excitement, taking the flowers from me, and giving me a short hug as she invited me inside.

I joined her in the kitchen as she got out a vase for the flowers. We had chosen to go casual for our first day and Kayli was wearing a white t-shirt with our business logo on the back, blue capris that showed off her skinny, fit body, and had her black hair pulled back into a ponytail. She asked me, “are you nervous?” I said of course, causing Kayli to laugh and ask why.

I told her, “I’m taking a very beautiful woman out on a date. I’m nervous, excited, and have about a billion different thoughts, concerns, and worries running through my head.”

She laughed again and came around the island kitchen where we had been standing across from each other. She wrapped her hands around my neck, said, “how about this to calm your nerves down?” As she planted a kiss on my lips, sneaking her tongue pass my lips to swirl together with mine. When she was done, I said, “that did help a little. How about you? Are your nervous?”

Kayli wondered for a moment before saying, “is if weird if I am too? We’ve known each other for years, slept together countless times, admitted our true feelings for each other, but to actually say we’re going on a date with each other? Yeah, I’m a little bit nervous.”

We left for dinner a short time after that, enjoying the meal we had together, spending the time getting to know even more about each other, things we’ve been too nervous to ask the other when we couldn’t be out in the open, before heading off to a movie.

The movie was good, more memorable for being able to hold hands with Kayli, or her resting her head on my shoulder as we shared a bucket of popcorn together. As we walked back to my car afterwards, Kayli wrapped her arm around me, leaning into me again. At the car, I opened the door for her, kissing her forehead before she got in. I joined her on the other side when she asked, “so, now what?”

I asked what she wanted to do and she responded, “I don’t know. I’m scared that if I go to your house, I’ll never want to leave. And if you come to my house, I’ll never let you go. But, another part is telling me that we need to take this slow, treat this exactly how we should treat a first date. My heart is telling me to never leave your side, but my brain is telling me to be smart about it, and wait to see how things really turn out.”

I said, “I understand. I’m kinda feeling the same way. I wouldn’t want this whole relationship to just be sex, like it has been. So, maybe for tonight, I should just take you home, kiss you good night, and I’ll call you tomorrow to set up a second date?”

Our second date actually happened the next day. Kayli picked me up from my house and we went bowling that night, being joined by Tara and Jennifer and their husbands. When she dropped me off late that night, we made out in her car, our hands getting frisky, when Kayli broke off, sat back in her seat, and said, “Danny, I want you so bad. I just want to go in your house, rip our clothes off, and go at it, and never leave. But, something is still telling me that we should wait. Will you hate me if I tell you no tonight?”

I sat back, taking Kayli’s hands in mine and said, “Kayli, I love you and love everything about you. I could never hate you.”

She smiled and said, “I’m glad. I think two weeks of officially dating, just to see if we can survive each other without sex being a focal point, then see how things go. What do you think?”

I said, “does that mean that we are officially a couple now? Am I allowed to say you’re my girlfriend?” Kayli laughed and said, “hell yes. I actually almost introduced you to the clients this morning we met with as my boyfriend. So, if you’re Ok with it, so am I.” We both had smiles on our faces as we hugged and said good bye.

The next week, Kayli had a really tough and picky client that was really stressing her out. She was at the office with me on Thursday, sitting at her desk, talking on the phone with the client, while I was at my desk, working on some paperwork for Tara. Kayli hung up her phone, letting out a muffled scream into her arm. I stood up from my desk and walked over to Kayli, standing behind her as she laid her head down on her desk.

Kayli, who was wearing a gray tank top with our business logo on it, turned to smile at me as I reached out with my hands, and started to rub her shoulders. She said, “hmm, that feels good.” I told her that she sounded like she really needed it and she said, “it’s certainly the start of something that I need. What are you doing tonight?” I told her, “wishing I could be with you.”

As she pushed back against me to stand up, she said, “I might just have to make that happen. I could use some one on one time with you. I got a showing to go to, I’ll let you know about tonight.” She wrapped my arms around my neck as I wrapped mine around her waist. I lifted her small, five foot tall, skinny body off the ground a bit, causing her to giggle before our lips met in a passionate kiss. We both said I love you as she walked out of the office.

I didn’t hear from Kayli until eight o’clock that night, when she knocked on the door of my house. As I let her in and greeted her with a tight hug, I said, “you know, as my girlfriend, you can just come walking into my house, you don’t need to knock.” She laughed and said, “I know, still trying to get used to it, I guess. You OK if your girlfriend spends the night?” I told her of course and asked if everything was OK. As we walked out to her car to get a back, she told me, “yeah, everything is good. Just been one of those days, and I don’t want to be alone tonight.”

Kayli, who was still wearing her tank top from earlier, ran into the bathroom, changing from a pair of leggings to a loose fitting pair of shorts that just barely covered her groin. She joined me on my couch, cuddling up next to me as I turned on a movie, wrapping my arm around her and pulling her in close, Kayli laying her head and one of her hands down on my chest as I rubbed her lower back.

We talked and cuddle as we watched the movie, until Kayli said, “I could get used to this. It feels so good just to relax with you and be with you and not have any pressure about being caught by the wrong person, or going too far or having to worry about anything.” I told her I was glad as she turned her head, leaning up to kiss me.

Kayli continued to turn her body until she was straddling me on the couch, her hands wrapping around my neck, my hands instinctively gonna her ass, squeezing her cheeks as I pushed my groin up into hers, our tongues swirling together. Breaking the kiss, I moved my lips down to her neck, leaving her kisses everywhere as Kayli moaned out, “I need you so bad. Please make love to me.”

I stood up off the couch, Kayli wrapping her legs around me. She laid her head down on my shoulder, kissing my neck as I walked us towards the bedroom. Once there, I sat her down, and pulled off her tank top, Kayli reaching behind to unhook her bra, sliding it off her gigantic double D breasts as she sat down on the edge of the bed. She reached forward, grabbing my shorts and pulling me forward. She quickly pulled my shorts and boxers down, my semi-hard cock at her face. I pulled off my shirt as she wrapped her hand around it, rubbing my shaft up and down as I grew harder at her touch.

Kayli looked up at me and said, “I’ve missed your cock. I know I wanted to give it a few weeks and some more dates, but I need you tonight.” I smiled at her as she flicked her tongue around my tip and said, “It’s missed you too.” Kayli took me in her mouth, bobbing her head up and down, as I ran my hand through her black hair that she had in a messy bun on top of her head.

I reached down with my other hand, taking Kayli’s breast in it, squeezing it, rubbing her nipple and lightly pinching it before switching hands, making sure both her breasts got equal attention. Kayli was deep throating me, one of her hands lightly squeezing my balls, the other hand still wrapped around my shaft, moving in motion with her mouth.

Taking me out of her mouth, Kayli kissed the tip of my cock, before scooting back on the bed. I climbed onto the bed, kissing up her right leg until I got to her groin. In one motion, I pulled her shorts and underwear off, Kayli helping to kick them off from under me. I kissed my way up to her clean shaven pussy, reaching out with my tongue to lick around her pussy lips, causing Kayli to moan as I flicked my tongue in and out of her. I ran my arms up her body, taking her breasts in my hands, squeezing them as I ate her out.

I found Kayli’s clit, kissing around it, before sucking it into my mouth, sliding two fingers into her pussy, quickly moving them in and out as Kayli wrapped her legs around my neck, her hands pressing my head into her, she moaned out, “oh yes, that feels so good…so close…YES!”

When she released her grip on me as she relaxed from her orgasm, I licked her pussy one more time before kissing a trail up to her flat, toned stomach, under her breasts, then all over them, paying more attention to her nipples, pinching and pulling whatever one I wasn’t licking and sucking on.

I kissed up to her neck, then over to her mouth, laying my hard, six inch long, thick cock in between her legs, resting on her wet pussy. As we kissed, I wrapped my arms around her body, my cock sliding inside her, Kayli breaking our kiss to moan as I filled her. I laid my head down on her shoulder, kissing her neck again, as I slowly started to pump in and out of her.

Feeling her nipples rubbing against my chest, I kissed down to them, taking them each one by one into my mouth, sucking them deep as I picked up my speed. I let go of her nipples, pushing myself above her, going harder and faster into her with every thrust. Kayli put her arms above her head, small moans escaping her mouth every time I slammed into her.

I rolled us over, managing to keep inside Kayli as she quickly started to bounce up and down on my shaft, her gigantic breasts nearly hitting her in the face, until I reached up to take them in my hands. I squeezed and pinched her nipples as she rode me, watching as her eyes rolled into the back of her head. I started to buck my hips up to impale myself deeper and deeper into her. “Yes! Yes!” Kayli was moaning out, her skinny, fit body a perfect sight to see.

I was close to finishing as Kayli slowed down, leaning down to kiss me, rolling her hips back and forth on top of me. I wrapped my arms around her, rolling us back over. Slipping out of her, our hands fumbled together as we worked to get my hard cock back inside her pussy. I was quickly slamming back into her, over and over, Kayli wrapping her legs around me, pulling me deeper and deeper into her. I threw my head back into the air, letting out a few grunts and moans, as I started to orgasm. Kayli pulled me down into her, her legs going tighter against me as I pumped my cum inside, slamming into her as my cock twitched over and over. I was panting as she whisper in my ear, “God, Danny, I love you!”

I caught my breath, saying, “I love you, too, Kayli.” She smiled as I pulled out of her, rolling off and onto the bed, as she said, “you have no idea how long I’ve waited for you to say those words after sex.” I replied back, “oh yeah?” She cuddled her naked body next to mine and said, “yes, and it was even better then I thought it would be. So worth it.”

I pulled her close, telling her I was glad and I wondered so too.

The next day, me and Kayli drove separate to our work office, but arrived at the same time, for a team meeting with Jennifer and Tara. As we walked in, holding each other’s hand, we both laughed as Jennifer said, “did you two finally fuck last night?” We asked how she knew and she said, “I know you two are in a new relationship and all, and things are changing, but something has just looked different between you two. But, as you walked in today, there’s a weird glow and happiness about you guys. So, figured that maybe you finally just fucked and got it over with. Am I right?”

Kayli smiled after her as we joined her and Tara at a table we had for our meetings, and said, “yes, you’re right.”

NSFW: yes

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