Hypothetically Speaking

Over the weekend, my LF and I were emailing when she mentioned that she was coming to town on Sunday to do some shoe shopping. The wife didn’t have a game to go to, so I didn’t think much about it because there wouldn’t be any way I could sneak out to meet her. Then LF mentioned that she had Monday off, so I suggested that she wait until Monday to do her shoe shopping because the wife would be at a game and I could meet her for dinner. Finally, we agreed on a place where we could get a bite and have a beer, and finally talk face-to-face.

I had that middle-low hum of anticipation all day from the excitement of meeting her, the uncertainty of what would happen, and the anxiety of running into someone I know and having to come up with a cover for why I’m having a beer with a female friend. Paranoid, maybe, but it added to the whole buzz, if you know what I mean.

She got to the restaurant a few minutes before me but was waiting in the parking lot when I pulled up. We greeted each other, and I thought we might hug but we didn’t; I don’t know if she was feeling as awkward about hugging in public as I was, but we just smiled and chatted as we walked in.

We were seated and had a beer in front of us pretty quick, then ordered our food. I wasn’t sure if we’d have much to talk about since we’ve been chatting and texting for some time, but the conversation flowed well, and we had a pleasant dinner. As we finished up, LF asked what I wanted to do now (as if she didn’t know.) I said “Do you want to blow the taco stand and drive around a bit?” She agreed, so I settled the tab and off we went.

Earlier in the day, I’d asked my former partner if the office would be free after 7 if, hypothetically, I needed a spot for privacy and, uh… talk. Originally he’d said it would not be, because one of the part-timers needed to be there for something until 8:30or so. Just as we started driving, he sent a text saying the office would, in fact, be clear by 7:30 if I still, hypothetically, needed it. (This is one of the reasons he and I have been such good friends since the 3rd grade, by the way.) I told LF that we just needed to kill about a half hour, so I found a nice, out of the way spot with a little shade.

After I parked, we talked for a few minutes more before I finally put my arm around her and went in for the kiss. That first kiss, the most exciting one, with someone new, is always the best, isn’t it? I was instantly hard and the bulge in my slacks was very noticeable, but I had the feeling LF didn’t mind. We kissed and touched, but both of us stayed in “safe areas” at first; caressing shoulders, elbows, knees, face, etc. When I raised my hand to her breast, over her shirt and bra, she moaned in my mouth. When I worked my hand down between her legs, over her pants, she squirmed and opened her legs to me further.

We had to be careful not to get too far gone, as there was the potential for people to be around. We were behind a store, and workers would come out in ones and twos for a smoke break. So we’d pull apart and let things simmer a bit, then go right back into it. I was developing a wet spot from my pre-cum in my trousers, I was so horny! I worked my hand up her blouse, and pushed the cup of her bra aside just enough to tweak her nipple, and when she groaned I knew it was time to find out if the office was clear!

It was a short drive, and the lights were off, so I just had to see if my key still works. It did; yes! I stuck my head in and called out, just to be safe, and nobody answered so we walked in. I gave her a quick tour around, looking for the little couch we used to keep in the server room (really comfortable for naps and the occasional make-out session), but it was at the front of the shop, near the window and door. Not exactly ideal, as someone walking by could glance in and see quite clearly.

We ducked into one of the offices, dark and full of junked computers, but enough room to embrace and kiss, and allow our hands to roam freely. I’m pretty good at the one-handed unsnapping of a bra, and LF was dutifully impressed when I had her breasts free. Her nipples called to me, and I massaged and tweaked them, marveling at their size, then I leaned down to suck them into my mouth. She moaned and squirmed, and as I sucked her nipples I undid her pants. I reached in and found her pussy dripping wet, and as I flicked her clit she leaned against me, groaning louder.

My cock was so hard that it was uncomfortable by this point, so I unzipped and pulled it out. She grasped me in her small, warm hand and stroked me as I continued sucking her nipples and playing with her pussy. I pushed her pants and panties down and she stepped out of them, giving me full access.

I sat down in a chair and pulled her to me, then started fingering her pussy and squeezing her ass. I was rubbing her clit and she straddled me knee for support. She was so wet, and I licked my fingers clean of her juices several times, and then went back to work. She shuddered and gasped in what I assume was an orgasm, and leaned against me, panting.

I stood up, unbuckled my pants, and pushed them and my boxer-briefs down to my ankles. LF kneeled in front of me, licking and kissing my engorged cock. When she took me fully into her mouth, it felt so good that I was afraid I would cum right then!  She started sucking me in earnest, and though I wanted it to continue, I couldn’t take it anymore. I love coming from a blowjob, but I wanted to fuck this woman!

I pulled her up and kissed her while playing with her pussy. I sat back in the chair and pulled her on my lap while she guided me into her. The angle was awkward, but still that first rush of entry was heavenly. We tried in that position for a bit, but I couldn’t get leverage and she was too short to keep herself from falling, so we switched. I sat her in the chair, pulled her legs up and her ass to the edge, and licked her slit. She tasted wonderful, and I loved her response when I worked her clit.

I tried entering her in that position, but my knees couldnt take the extreme bending to get the angle right. I had her stand up and bend over the chair, ass up, and I bent my knees enough to get everything lined up. Her pussy was still soaking, and my cock slid into her, filling her and making her moan again. I knew I wouldn’t last long, after such a long build-up, but I tried to hold off the inevitable by stopping for a few seconds here and there.

Finally, I couldn’t hold it any longer and I asked her where she wanted me to cum. “On my back!” she answered, and I pulled out just in time to shoot rope after rope along her ass and back. One shot almost reached her neck! (In truth, if I’d been trying I probably could have hit the wall from where we were, but I didn’t want to mess her hair. Not this time, anyway. Hehe.)

I was a mess, LF was a mess, but I think we both felt pretty good. I duck-walked into the kitchen area and grabbed some paper towels, and cleaned my cum off of her back, then cleaned up my groin as best I could so I could pull up my pants (still had my shoes on!) LF also got dressed, but her efforts were hampered somewhat by my interruptions to kiss and touch. When we were finally presentable (I think she stuffed her panties in her purse) we left. I drove her back to her car, and we shared one last kiss before she got out. I watched until she got in her car, then I drove home, satisfied and smiling. There’s still so much I want to do to (and with) this woman, though! I can’t wait until the next time; hopefully we’ll have more time and privacy, and maybe even a bed.

When I got home I sent my former partner a text saying “all clear” to let him know I was no longer in the office in case he wanted to go in late (as he’s been known to do). He texted back “Hope it worked”, to which I replied “Hypothetically speaking, it worked just fine. Thanks for the help!”