As most of you probably know by now, Holly and I have been trying to spend as much time together as we can before her hubby returns from his trip and we have to go on our dreaded "break". We've gotten to see quite a bit of each other the past couple of weeks and have really had some great times together - sometimes having lots of hot sex, and other times, just doing normal stuff like having lunch or going to a movie. We've actually packed a lot in over this time and have almost always had a plan for each day we've spent together.
But the other day was different. We had simply planned to spend time together. In truth, Holly had offered to come up with a plan for the day as we were going to be meeting in her neck of the woods. The night before, she'd hinted at having a surprise for me and told me to check my email in the morning for instructions. I must say, I was definitely intrigued. When I got her message in the morning though, she said that she'd decided to go with a simpler plan and just asked me to meet at her office for a short visit before heading to lunch. I think it was implied that we'd also end up spending some time at a hotel at some point, too.
Fortunately for us, Holly has a real office with a real door (and a real lock)! When I arrived, she was playing the CD I'd made for her on the eve of another of our breaks. Yes, I made her a "mix tape" - I'm a dork like that. I had come dressed from work and was a bit shabby looking, but I had planned ahead and packed a change of clothes in my gym bag. Holly and I sat and talked for a few minutes and I then I asked her if it was ok if I changed clothes real quick. She smiled and assured me that was fine with her. So, I stripped down to my tight, black briefs and then bent down to kiss her while she sat on the couch.
In between kisses, I took the opportunity to slip my hand down her low-cut dress to play with her tits. I was getting hard - the bulge in my shorts growing more prominent. I was still bent over her when I said, "I want to give you your first orgasm here in your office before we get to the hotel."
"Well, I thought it might be fun to wait," Holly replied. "But, what did you have in mind?"
"I was thinking about turning you towards that wall over there, slipping your panties down around your ankles, and fucking the hell out of you from behind until you cum."
She smiled broadly and said, "Hmm...I guess that might be a good idea, too." With that, she stood up and walked over to the corner near the door. She reached under her dress and slipped her panties off and tossed them into the corner. Holly lifted up her dress to expose her ass as I stepped out of my briefs. She stuck her butt out to meet me and I put my cock between the crack of her ass and grabbed her hips to pull her toward me as we ground our bodies together. My dick was pointing straight up at the ceiling and I teased her like this for a minute as I held on her and rubbed her ass a bit. I was ready to fuck, though, so I soon took my cock in my hand and guided it toward her wet, slippery cunt. I slid it back and forth a few times, grazing her clit with the head, before slipping inside her. She groaned as my thick cock spread her open. I pumped her deep and pretty hard as Holly braced herself against the wall. I was humping her like an animal right there in her office and it was so fucking hot! When I reached around and fingered her clit, it only took about a minute to make her cum. Since we were in her office, she had to be pretty quiet, but she did make some sexy little moaning noises to clue me in on what was happening. "Mission accomplished?" I asked.
"Uh huh," she mumbled in reply. I pulled out and looked down at my cock and it was glistening with her juices. Holly noticed the direction of my gaze and asked, "What should we do about that?"
"I think you should clean me off." Holly told me to sit on the couch and she got on her knees between my legs and slowly licked and sucked my throbbing dick. She was bobbing up and down on my cock and jacking the shaft. It felt incredibly good but I didn't want to cum until later when I could fuck her properly at the hotel. So, I kissed Holly and suggested that we go on to lunch while she still gripped my cock in her hand. She agreed, released her grip, and stood up to straighten out her dress. My damn cell had been ringing off the proverbial hook (I wonder, will kids in 10 years even get that expression?) and so I quickly returned a business call as Holly cleaned up a bit. She was about to put her panties back on as I hung up from my call but I tossed my phone down on the couch and hiked her dress back up and plunged back inside her. I gripped her hips tightly and gave her several more quick, deep pumps before finally letting her get dressed so we could go.
Holly had to take care of something and we'd decided to drive separately to the hotel anyway, so I drove over and checked in and then she picked me up and took me to a really authentic, really cool, and really tasty sushi place for lunch. We had some time to just relax and chat as we ate lunch and it truly was a fun time. Toward the end of our meal, I tried to talk with her a bit more about the whole open relationship issue, but I know she views that as more of a "down the road" topic and so I didn't push it too far. The stuff we talked about was good, though, and as always, she makes talking about difficult topics a lot easier and I really appreciate that. As we walked out of the restaurant, I put my arm around her waist, pulled her close and whispered in her ear, "I love you." She stopped and turned to me to kiss me and assured me that she loves me, too.
We headed back toward the hotel but made a quick stop at a local store so Holly could show me something we'd been talking about at lunch. That was fun, too, but I was definitely ready to get her naked and wet again so we drove up the street to the hotel. Once in the room, I stripped down again, peeled her dress off her and turned off all the lights as she laid back on the bed. She was wearing the sexy bra and panty set that she'd bought with me when we had celebrated our six month anniversary a couple weeks back. It's a pink bra with little black polka dots and some lacy pink and black panties (at least, I think there's some pink in there - they didn't stay on that long). So anyway...I was on top of Holly, kissing her hard and grinding my crotch against hers in the dark. A storm was rolling up outside and so it really was pretty dark in the room and we could hear thunder rumbling a bit in the distance. It definitely helped set a sexy mood!
I worked my way down her body and slid her panties down her legs. I don't remember the exact order of things but I proceeded to use a combination of fingers and tongue to stimulate her clit and g-spot. After giving her three powerful orgasms in fairly short order, she was dripping wet and I know her well enough to understand that she was aching to be fucked. And fuck her I did! She mumbled something about not really being able to move at that point and pretty much told me that I could have my way with her. Don't tell Holly, but I pretty much had already assumed that! I talked some junk to her, telling her how wet her pussy was and how I thought she really liked me having my way with her. She moaned her agreement into my mouth as I kissed her hard again.
I was super hard and dripping from the head of my cock as I eased into her. I slid in easily since she was so wet and ready for me. We started off with me on top and alternated between fucking her hard and fast and then more slowly, teasing her with just the tip. I didn't really pay a lot of attention to her orgasm count after this point, but I'm reasonably sure that she came a few more times during our very hot, breathy romp. There were several positions tried in round 1, but none of them included her on top - I was determined to be in charge! Suffice it to say that Holly spent lots of time on her back, her side, and on her hands and knees taking my cock.
At some point, she told me how good it felt to have my balls slapping up against her pussy as I was pounding her hot, wet, little box. That inspired me to grab my cock ring and slip it on over my shaft and balls. In case you don't know, wearing a cock ring that way makes the balls more "full" and prominent and sort of pushes them together and forward. Once in place, I walked back over to the bed and pointed my dick right at her face. She sort of backed away from it (but, in reality, I think she was just trying to re-position herself to better suck it). I grabbed the back of her head and told her that moving away from my cock wasn't allowed as I forced it between her lips. She gladly sucked me and remarked how hard I was as she cupped my balls in the palm of her hand.
I was ready to be back inside her and so I had Holly slide over to the edge of the bed and put her ass up in the air for me. I immediately rammed my rigid, veiny cock cock back inside of her sopping wet snatch. It was literally running out of her and the insides of her thighs were all slick and wet - I loved it! Anyway, I fucked her doggy style for a good long time as she played with her clit. I asked her if she could feel my balls even better now and she replied that she definitely could. I was beyond ready to cum by now and just blasted away at her poor little pussy. I stuck my thumb in her ass as she rubbed her clit and she came again. Then, I pulled out and stroked my cock fast and hard. After I rubbed off all of her natural lube, I leaned over and spit on the head of my dick and began pumping faster and faster. Right as I was about to blow, I shoved it back into her. I moaned and grunted and shook as my legs tensed up and I coated the inside of her cunt with my thick, milky cum.
I braced myself on Holly's back for a minute until I caught my breath and then slipped out of her and went to wash up. I then collapsed back on the bed with her and we just cuddled and rested and chatted for a bit. There were more sweet kisses and later a brief round 2 where she got me up again with her mouth and hand before climbing on top for a nice ride. I couldn't muster another orgasm, though and so we spent our last few minutes just lying together and kissing some more before I had to hit the road and head home.
All in all, I'd say that it was a great day; full of plenty of hot sex, warm feelings and lots of love. Pretty good for a guy without a plan, huh?
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