tl;dr: I met u/HolidayBeginning 8 months ago on this subreddit and after 2 previous drinks dates, last weekend we had 20 hours of bliss. He’s a complete gentleman, championship cuddler, and incredible at getting me off. I made him cum 5 times over the two days and I couldn’t even count how many I had. A would bang again :)

(skip to ***** for the dirty details - very long and detailed because I don’t want to forget a second of it!)

Back in June of 2019 I reached out to u/HolidayBeginning after seeing one of his posts looking for a partner in the DC area. We hit it off immediately, but seeing as he travels constantly for work, finding time to meet up has been a challenge. We met for drinks early in July but it was a weeknight and pretty late so nothing happened beyond making sure neither was a serial killer. We kept trying to make things work, but eventually things stalled out.

Once the death of kik rumors started flying around I reached back out to him to make sure I could still connect with him after the service went away. We switched to a new app and our conversation picked up again. Fast forward to the end of the year and he told me he was planning a week’s vacation at “home” in DC for mid-February. We decided to put it on our calendar just in case.

The week comes, and we decided to meet up for dinner / drinks one last time to make sure we were both still interested. We were, and if he hadn’t flown in on a red eye that morning we would have come back to mine for some early fun.

The next day we agreed to logistics - I had taken the day of our date off from work, and he had about a zillion hotel points, so he booked us a very nice room in a downtown hotel and agreed to meet around 3pm. We discussed kinks and toys and he gave me a list of things he wanted me to bring. I couldn’t think straight the next couple days - I was so ready for this.

*************

I arrived at the hotel just before 3pm, small suitcase in tow, dressed in my business casual / casual Friday best. Tight dark jeans, loafers, a low cut blouse and matching jacket. Underneath, incredibly sexy red and black lace lingerie.

I was sure the Uber driver knew what was going on when he picked me up at my apartment to drop me off at a hotel. That only added to the thrill. Not to mention, fully half my suitcase was packed with sex toys. :)

I settled in at the (very empty!) hotel bar and quickly had a couple of gin and tonics to calm my nerves. I texted him to see if he had arrived yet - he had checked in (guess we just missed each other in the lobby!) and was waiting for me. He came down and had a G&T as well and then he invited me up to the room.

I had a feeling it would be nice, but the room was sleek and sexy. Windows overlooking the street, and directly into the apartments across the way. Big couch, king bed.

I was nervous as I put my things down - I always get butterflies the first time I’m with someone. I used the restroom and then found him already laid out on the bed. I sat down and immediately we started making out. He’s a fantastic kisser. We took our time, slowly stripping off each layer of clothes. As we did we reviewed our hard limits and agreed on safe words if we needed them.

Eventually I got greedy, as I always do. I had to see the cock in person. It did not disappoint. He had leaked enough precum to soak through his boxers and his pant leg before we got naked. I found that incredibly sexy and it only made me wetter.

I slid down to the floor and started worshiping his cock. He told me he liked it sloppy and messy, so that’s what I gave him. It took a little time for me to get used to his size, but him telling me “good girl” in that English accent definitely helped encourage me. It took a bit of gagging and a bit of “help” with his hands in my hair to get it all the way down my throat. He told me later “you look so happy with a dick in your mouth” - I guess it’s probably true. :)

It wasn’t long before he was spraying his hot cum all over my tits. I felt how big his load was and listening to him cum was incredibly sexy. Even better, as soon as he was done he sat down and started playing with my tits and rubbing his cum into my skin. I loved that he wasn’t shy about it.

After a little bit I got up and cleaned myself up a little, I still had my panties on but they were soaked through and my wetness was coating my thighs. I wiped up a little of it and washed the cum off my chest.

I grabbed my Liberator blanket and spread it on the bed. Since I’m a squirter, and we planned to sleep at least a little, I didn’t want anyone stuck with a wet spot.

I laid down and immediately he had me pinned down, telling me he was going to edge me and tease me. Blowing him had made me so horny that I told him it wouldn’t take much. He saw how soaked my panties were and pulled them off before gently, barely, touching my lips and clit. I started to squirm and he laid next to me, pinning one arm under him, using his leg to hold one of mine in place. He put his arm under my head and grabbed my other wrist, immobilizing me while leaving his other hand free to caress and torment me. I struggled against his grasp, but his grip on my wrist was firm. That only turned me on more. I adore being manhandled and overpowered.

Every time I tried to close my legs to rub against his hand he forced my legs back open. I was at his mercy and it was such sweet torture. He is incredibly skilled and finally after what seemed like hours, but was probably only a few minutes, he made me cum hard with direct stimulation on my clit. When I cum I shake and can be very loud :) He gave me a few seconds to breathe before I asked if he wanted to see me squirt. I told him what it took - direct pressure on my gspot, trapping it to my pubic bone - and he said he thought his technique would do the job. Um, yes. Yes it did. We were both very happy that I brought the blanket as I soaked it, repeatedly, throughout the time we were together. He made me cum a few more times alternately with his hands and his mouth. His oral skills were incredible and on par with everything else about him.

After recovering for a few minutes, I started playing with his dick again, caressing his balls as I sucked him. I had to have him in me so I begged him to fuck me. He pinned my legs back and fucked me hard. He’s quite vocal which I love. Hearing him cum again, and feeling it inside me (with a condom) was awesome.

He cleaned up a smidge - got rid of the condom - and found me still in a heap where he left me. He got back in bed and we cuddled for a good long while before deciding maybe we should rinse off some and figure out some dinner. I jumped in the shower first and then laid back down while he went to shower. We settled on a place nearby for dinner, I made a quick reservation on my phone, and we got dressed.

Dinner was delicious and we had a really good time talking about all manner of things, but mostly our shared experiences in Europe and places we’ve been. I got some bad news during dinner and he was amazing. Really supportive and kind while I processed it. There wasn’t anything I could do about the news, so we decided to go back to the hotel.

I adore lingerie, and we had plans to chill a little and let dinner settle, so I immediately changed into my sexy satin pj set I had brought - teal satin with black lace, camisole and short shorts. He stripped down to his boxer briefs again and we cuddled and talked some more until his face ended up on breasts. That got him going again, kissing my tits and caressing my neck.

I have incredibly sensitive nipples and neck and I was already wet again. He remembered we hadn’t even gotten to the toys he instructed me to bring, so he told me to go get them. I had a packing cube filled to the brim with a couple of glass dildos, my cordless wand vibrator, another small vibrator, lube, nipple clamps, a paddle, and a few other things. He selected the dildos and wand and went to town on me.

I have no idea how long it lasted but easily 20-30 minutes of him fingering me, fucking me with my dildos, making me squirt, and then the piece de resistance, a dildo on my gspot and the wand on my clit. It was effectively one long orgasm the entire session, with peaks of intensity. I was so loud we were a little afraid of a noise complaint. I tried to muffle my screams with my hands and his chest as I shook and quivered against him.

I was nearly spent but I wanted to make him feel as good as he made me feel, so I reached over and started stroking his dick while cuddling. Early on I had tried to jerk him off while he was playing with me but I quickly lost my focus. I was determined not to this time. Listening to his soft moans as I played with his cock and balls turned me on again and soon I was on my knees next to the bed again. I asked if he had ever tried using a vibrator on himself and he said no, but he was open to it. I stroked him and played with his balls as I ran the wand up and down his dick.

It was really fun when I turned the vibe to pulse and held it against his frenulum. Listening to him moan, and watching the head of his cock swell in time with the pulses was mesmerizing. I loved edging him, but decided I should be nice. Eventually I asked if he wanted to fuck me again, and he did. Getting fucked by him felt awesome. The cuddles after were almost as awesome.

Eventually we both decided to clean up and rinse off before turning in for the night. I read a little as he dozed off but quickly followed him to dreamland.

Stay tuned for part 2 ;)