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The 1st Real Date (& Maybe the Last...)
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Just realized that I never filled you all in over here about what went down during my date last week and beyond:

A little context for those that aren't up to speed, for over a month, I've been talking to a couple that is new to this lifestyle. Since they are new, I've been pushing their limits but haven't broken any of them yet. For example; last night was supposed to be our first time fucking but the wifey (HW) and I jumped the gun a week early without the cuck around. Now it was his chance to see what he's been missing out on.

The cuck got us a room and a table reservation at a hotel. Meeting them at their room, the three of us head down to the dinning hall. From the moment I arrive, HW is all over me, finding any excuse to be up against me while the cuck is sort of just hanging back, happy to just bare witness. Heading down to the dinner hall and taking our seats, you'd thought that she and I were the married couple and the cuck was just a hapless third-wheel.

HW is seating right next to me as we discuss and reaffirm boundaries and expectations over dinner and drinks. During this talk, under the table, I reach over and take HW's hand and guide it towards my lap. She eagerly takes the hint and rubs my cock through my pant leg; stroking and squeezing it with glee as we continued our conversation.

By the time dinner was done, she and I were more than ready to get back to the room. On the elevator back up, we have a hot make make-out/heavy petting session while the cuck watched from the back corner.

As soon as we pass the threshold of our room, it was on. Before cucky can even close the door, HW and I begin stripping each other, ready to finally get back to what we started a week ago. Laying her down one of the two beds, I give the cuck the condom and told him to open it up for us while HW and I enjoyed tasting each other. After a quick bit of oral fun, I acknowledge his presence by asking if he had that condom ready yet. He did. I stood up by the bed and spoke to him directly:

"Come put it on me, then"

Awkwardly, he waddled over; this was his first time seeing my cock in the flesh and he's got almost as much cockshock as his wife did her first time.

"You can touch it, if you want. Find out what a real cock feels like."

He wraps his small man hand around me, his face a deep red as he gave my dick a couple of squeezes before rolling the condom down its length.

Taking a seat on the other bed, Cucky got a VIP view of his wife getting plowed. He was quiet for the most part; he took his own dick out and played with it for a bit but was having trouble getting hard. Meanwhile, I have her folded like a pretzel while dicking her down proper.

HW is losing her mind as her pussy gets the workout it's been craving. As far as I know, this would be the first time he would see his wife cum; not climax or orgasm but body-quaking, sheet-soaking cum. At one point, I instructed the cuck to reach into the bag I brought and to grab my vibrator. Once he handed it to me, I clicked it on and held it to her clit as we fucked.

"Holy shit!" she blurted out, "I didn't think your dick could have gotten any better!"

Since she didn't have to keep quiet and had all night, HW was even wilder and more animated than before as she gripped and tore at the sheets in ecstasy, pleading for more.

When I say we spent all night fucking, I'm only being slightly facetious. We took regular brakes to hydrate and such but most of my time was spent inside HW. We even fell asleep with my cock in her, cuddled up in one bed while her husband had to sleep alone in the other bed.

Even when morning came, she and I were still at it. Not as vigorously as before, mind you, but we were still using each other's bodies to pleasure ourselves. Cucky woke up to me sitting up in bed with her straddling my lap, rocking and grinding on top of me as we discussed breakfast; the hotel offered breakfast in the dining hall but we didn't really feel like leaving the room. Instead, Cucky ordered us room service over the phone while his wife and I cranked a couple more orgasms out of her. By the time food arrived, I was done; I still had cum yet (my medication makes it difficult for that to happen) but I was satisfied. Besides, we had an hour or so before check-out.

After our meal, while we were packing up, I asked the cuck how he was feeling. He admitted that it wasn't what he was expecting but he really enjoyed himself. He said it was like watching porn starring his wife and that he didn't know she could cum that hard or that much. After seeing that, he said he would be fine if she and I fucked without him, just that he would appreciate pics or videos of the action.

And, with that, the date was done! But that's not where the story ends...

A few days later, I got a text from the HW stating that, even though we all had fun, they are going to close their relationship again. When I inquired as to why, turns out that cucky had the idea of reclaiming his wife, which is common, but attempted to do so while she was sleeping. She never agreed to or even discussed such play with him so that was already a large boundary crossed but he also nutted in her when she's made it very clear as far as I know that she isn't on any form of protection. She took a morning after pill so hopefully that nips that in the bud but, after her husband behaved in such a way, she decided that he may not be ready for this lifestyle so they are gonna stop all extra-marital play until they can get this settled.

Sorry again for making you all wait; I had originally posted this over on the discord server but forgot to put here as well.

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1 year ago