Thread: Our Journey
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Old Yesterday, 05:47 PM
RealWithRy RealWithRy is offline
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Default First ACTUAL play date

After months of conversations that never seemed to go anywhere, this one felt different.

When he first messaged me, he assumed I was single. It became obvious pretty quickly that he hadn't read our profile very carefully, so before either of us got invested, I explained everything. I told him I was happily married, that my husband knew I was talking to him, and that if we ever met, it would be something we experienced together, not something I was hiding.

I expected the conversation to end right there.

Instead, he thanked me for being honest. He admitted he hadn't looked that closely at our profile and asked a few respectful questions. Once he understood our situation, he simply said he was comfortable with it.

That response surprised me.

He was a handsome Black man named Tony with an easy smile and a calm confidence. More than anything, he made us feel comfortable. He never acted like our relationship was strange or something to judge. He didn't seem bothered that I was a short, chubby white woman, and he wasn't intimidated by the idea of my husband being present. He treated us like real people instead of a fantasy.

After several days of talking, we agreed our first meeting should simply be over coffee.

Our favorite coffee shop had become our unofficial meeting place, and it felt like neutral ground. We spent over an hour talking about life, work, relationships, and getting to know each other. There wasn't any pressure. It honestly felt like three people seeing whether everyone genuinely clicked.

By the end of the conversation, we all agreed that if we decided to continue, we'd meet the following Friday at a hotel about an hour away. We'd drive separately so everyone had complete freedom to leave whenever they wanted. Nobody wanted anyone to feel trapped or obligated. Just knowing everyone had their own vehicle made the whole situation feel safer.

My husband booked a nice suite, we found a babysitter, and suddenly this wasn't just another online conversation anymore.

Friday morning arrived, and I woke up with butterflies in my stomach.

I dropped our child off with the babysitter and spent the day getting ready. I had my hair freshly cut and styled, treated myself to a manicure and pedicure, and when I got home, I dug through my closet until I found a lingerie set I'd been saving for a special occasion.

If there was ever a day to wear it, this was it.

When my husband got home from work, we made the drive together. I don't remember much about the trip because my mind was racing the entire time. Every mile made it feel a little more real.

We'd agreed to meet first at the hotel bar.

Originally, we'd planned not to drink, but the moment we sat down, my nerves completely got the better of me. I laughed and admitted I needed one shot just to calm the butterflies. My husband had worked all day and then driven an hour, so he decided to have one too. Tony wasn't much of a drinker, so he ordered a single beer while we settled into conversation.

Looking back, that conversation was probably the most important part of the entire evening.

Before anyone even thought about going upstairs, we wanted every expectation and every boundary out in the open.

The first thing we discussed was privacy.

All three of us agreed that nothing would ever be photographed or recorded. No pictures, no videos, no audio. We wanted to be fully present without worrying about anything living forever on someone's phone. He agreed immediately and never questioned it.

Then we talked about consent.

We all understood that agreeing to meet didn't mean anyone was obligated to do anything. At any point, for any reason, any one of us could decide we weren't comfortable anymore and walk away. There wouldn't be hurt feelings or pressure to continue. Knowing that gave me an incredible sense of security because it reminded me that we were choosing this together every step of the way.

We also talked about pace.

None of us wanted the evening to feel rushed or choreographed. We agreed we'd simply let things happen naturally, if they happened at all. There wasn't a script to follow or a checklist to complete. We wanted conversation, comfort, and chemistry to guide the evening rather than expectations.

When the conversation turned to personal boundaries, I was completely honest. I explained that there were some things I was comfortable with exploring and others that I wasn't interested in. I was open about what I felt comfortable with, including that oral sex was within my comfort zone, while anal sex wasn't something I wanted to do. He accepted those boundaries without hesitation or debate, which made me feel respected.

We also discussed my husband's role.

From the very beginning, we'd agreed he wouldn't be physically involved. He would stay in the room because experiencing this together was important to both of us, but his role was simply to be present and supportive. That arrangement was what made both of us feel comfortable, and our guest respected it completely.

We even talked about protection. At the time, I was taking birth control, and because of that, none of us felt condoms were necessary. Looking back years later, we were young and probably should have been more cautious. At the time, though, I trusted that the pill was enough, and it honestly didn't concern me the way it probably should have.

One last thing I shared was something that had always been true about my personality.

I'm not someone who likes to direct every moment. If I'm comfortable and I trust the person I'm with, I generally prefer for the man to take the lead while I simply relax into the experience. That didn't mean giving up my voice or my ability to say no. Quite the opposite. We had already agreed that I could slow things down or stop everything at any moment, and so could either of them. Knowing those safeguards were in place made it much easier for me to let go of some of my anxiety.

By the time we'd finished talking, something inside me had shifted.

The fear that had followed me through months of unanswered messages and second-guessing myself had quietly disappeared.

It had been replaced by trust.

As we stood up from the bar and walked toward the elevator, I reached over and squeezed my husband's hand.

After months of wondering if we'd ever find someone who respected us, our marriage, and the boundaries we'd worked so hard to establish, it finally felt like we had.

The elevator doors closed, and with my husband on one side of me, and Tony on the other, we quietly closed one chapter of our lives and opened up a new one.

We rode the elevator to the top floor exchanging small talk, but I don't think any of us were really paying attention to the conversation. We were all smiling, all a little nervous, and all wondering what the rest of the evening would bring.

When we stepped into the suite, the atmosphere immediately felt relaxed. My husband had picked a room with a separate sitting area, giving it more of a comfortable apartment feel than a standard hotel room.

Tony and I sat down at the small table while my husband settled into the recliner across from us. Someone grabbed the deck of cards we'd brought along, and before long we were laughing over a few simple card games. It turned out to be exactly what we needed.

The cards gave us something to do besides stare at each other.

The conversation drifted everywhere, our jobs, where we'd grown up, funny dating stories, music we liked, and travel. My husband and Tony discovered they had more in common than either of them expected. They joked back and forth like they'd known each other much longer than a few hours, and seeing that friendship begin to form helped ease my remaining nerves.

That hour or so was probably one of the smartest decisions we made all evening.

Instead of rushing into anything, we gave ourselves time to become comfortable together. Every laugh made the room feel a little less intimidating. Every story reminded me that Tony wasn't just someone we'd met online, he was a genuine person, and so were we.

Eventually there was a natural lull in the conversation.

I smiled and excused myself for a few minutes to change into my lingerie set that I had brought along.

Standing alone in the bathroom, I caught my reflection in the mirror. My heart was pounding just as hard as it had been earlier that day. I took a deep breath, reminded myself that nothing had to happen unless everyone still felt comfortable, and that any one of us could change our mind at any point.

That thought gave me confidence.

When I walked back into the room, both of them looked up. I could feel my cheeks getting warm, but their smiles immediately put me at ease.

Rather than making a big moment out of it, I quietly walked over and sat on the edge of the bed.

There was a brief silence.

My husband smiled toward Tony and, in his calm, reassuring way, simply nodded in my direction.

Tony looked at me for a moment, silently checking that I was comfortable. I smiled back and gave a small nod of my own.

He walked over and sat beside me.

The first kiss was gentle and unhurried.

My husband sat forward in the recliner and watched the events unfold while simultaneously staying quiet as if to not disturb us.

The slow and gentle kiss turned into lightly nibbling and making out. Pretty soon I felt my hand wander off toward Tony's pants. We let things happen very naturally. I unbuttoned his pants and reached my hand inside. What I felt was not something I was used to. I had only had one boyfriend prior to my husband and I was rather nervous that I would be able to perform for such a well endowed man.

Eventually, he slides his pants and boxers off, and pulls his shirt off, exposing a dark, slightly muscular body. He started stroking himself and before I continue, I look over at my husband where he is grinning as if telling me to continue.

I slide off the bottoms to my lingerie set and spread my legs slightly. I grab hold of his hand and press it on my inner thigh. He gently caresses around before entering me with his finger, every moment, making me more excited than the last. I glance over at my husband again and he shakes his head yes in approval. Over the course of the next few minutes he gets me to climax several times, despite the nervousness of me up until this point.

"Are you ok with a blow job?" Asked Tony.

Immediately thoughts began to race. I had never given a guy who was this big head before, but I guess I'm a little bit of a people pleaser, so I give it a try. I spread his legs slightly and position myself in between them while letting the saliva build in my mouth. I grab ahold of it and wrap my lips around it the best I can and slowly bounce up and down. I keep a close eye on his reaction. He leans back slightly and lets out a moan of pleasure like he is enjoying himself. Glancing over at my husband again, he shouts out "Keep focused on Tony, I think he's enjoying it!"

This goes on for a few minutes until Tony stands up and directs me to lay on my back on the edge of the bed. Then he walked over to my husband.

"Are you sure you are ok with this?" Tony asked.

"Absolutely" replied my husband.

Tony asked another question, "Where do you want me to finish?"

"Anywhere is fine by me, Ry is on birth control, just make sure she is fine with it." Replied my husband.

Tony came over and stood between my legs and I put them up and rested them on his chest. He looked me in the eyes and asked me if he could finish in me. The communication and openness this far made me want him even more. Tony was a very respectful man that had made me feel wanted and desired. "Yes, you can if you want" I replied.

He then proceeded to push it inside me. I had never felt one this large in me before. He slowly pushed it all the way in and asked me how it felt. I told him it felt good and just to start slow. He got a rhythm down and continued to thrust in me slowly but deeply. This went on for about 10 minutes until the pace started picking up.

"Are you sure you are fine with me finishing in you?"

"Oh yes, give it to me!" I excitedly replied.

Within 30 seconds of my last response, he pushed it in one last stroke, as deep as it would go, and released his load inside of me. He held it for a second, then slowly backed out. Then I immediately feel it running out of me. This was definitely a big one.

Pretty much immediately he got quiet and went and took a shower. While he was in the shower my husband came over with some paper towels and helped me clean up. We spent the rest of the evening just talking and hanging out. We had gotten pretty close with Tony and genuinely adored his company.

Tony and I eventually drifted off to sleep in the bed while my husband stretched out on the couch in the sitting area. It wasn't something we'd planned, it just happened naturally. After everything we'd built up in our minds over the previous moments in this journey, the ending to the evening felt surprisingly peaceful.

The next morning, sunlight shined through the curtains, and I slowly realized where I was.

For a second, it almost felt like waking up from a dream.

Then I looked around the room and smiled.

There we were, three people who previously had been complete strangers sitting in a coffee shop, wondering if this was all a terrible idea.

Instead, we'd spent an evening together, and thoroughly enjoyed ourselves.

As everyone started waking up, the mood was surprisingly light. There wasn't any awkward silence or uncertainty about what to say. We joked about who had snored the loudest, teased each other about the card games from the night before, and laughed about how nervous we'd all admitted to being.

After getting dressed and packing our bags, we headed downstairs together for breakfast before checking out.

Sitting around the table with coffee and breakfast felt oddly... normal.

If someone had walked by, they probably would have assumed we were simply three friends grabbing breakfast before heading home.

We talked about our families, future travel plans, work, and the restaurants we still wanted to try. The conversation was easy, relaxed, and comfortable in a way I never would have expected.

What stood out to me most was that there wasn't any pressure about what came next.

No one expected promises.

No one tried to define anything.

Instead, we all agreed on one simple thing, we'd had a great time together, and if life lined up again, we'd love to do it again.

When it was finally time to leave, we walked out to the parking lot together.

There were hugs, smiles, and the familiar exchange of, "Drive safe."

Before getting into his car, Tony grinned and said, "We'll have to do this again sometime."

My husband laughed and replied, "I think we can probably arrange that."

I couldn't help but smile.

As we watched him pull out of the parking lot, I looked over at my husband. Neither of us said much for the first few minutes of the drive home.

We didn't really need to. We both just felt satisfied.

And that's our first time actually arranging a meetup. The lifestyle just took off from there!
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