Advice for the first meeting please
Advice for the first meeting please
This may seem strange, but I’m getting hung up on a small detail. Has anyone got any advice or tips for moving from the hotel bar to the room. Any ways of making it feel more natural than just asking shall we move to the room?
And when we get to the room, is it easier for the other guy to make the first move or me and my wife or my wife to make the first move?
Any tips welcome to make our first time a sublime experience welcome!
And when we get to the room, is it easier for the other guy to make the first move or me and my wife or my wife to make the first move?
Any tips welcome to make our first time a sublime experience welcome!
Re: Advice for the first meeting please
I don't think you should concentrate too much on making the first time feel "natural" from start to finish. The truth is, it's not very natural at first
If they get to a bit of kissing in the bar, then the transition to the room should probably happen fairly organically. If (more likely) the time comes and you're all sitting there feeling a bit nervous and awkward, then someone blurting out "let's go to the room" is as good an ice breaker as any.
Once there, you could suggest that you and he begin undressing your wife together. Some kissing - lips, neck, whatever - depending on who's standing where - and slowly taking off her clothes and then your own.
Once the 'action' starts to happen, things ought to begin to progress pretty naturally, as they do when people start lose their shyness and inhibitions, and get aroused. Once everyone is naked there's not as much to be nervous or awkward about, any more

If they get to a bit of kissing in the bar, then the transition to the room should probably happen fairly organically. If (more likely) the time comes and you're all sitting there feeling a bit nervous and awkward, then someone blurting out "let's go to the room" is as good an ice breaker as any.
Once there, you could suggest that you and he begin undressing your wife together. Some kissing - lips, neck, whatever - depending on who's standing where - and slowly taking off her clothes and then your own.
Once the 'action' starts to happen, things ought to begin to progress pretty naturally, as they do when people start lose their shyness and inhibitions, and get aroused. Once everyone is naked there's not as much to be nervous or awkward about, any more

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Re: Advice for the first meeting please
I thinks for some wives it would be easier if you let her go to the room alone with him and give them some time to get to know each other. She can either message you when she is ready for you to come up or just set a specific time amount like 15 minutes. She might be too busy to message .
Re: Advice for the first meeting please
I would say the easiest or most natural transition crom the bar to the room would be a nice you’ve finished a round of drinks suggesting you get another to enjoy in the room. “I’m ready for another round. Should get one for the room?” Addresses the need for a new drink and action to move to the bar but also promotes you’ve got somewhere to take it to me you have it.john1616 wrote: ↑Tue Jun 03, 2025 2:51 amThis may seem strange, but I’m getting hung up on a small detail. Has anyone got any advice or tips for moving from the hotel bar to the room. Any ways of making it feel more natural than just asking shall we move to the room?
And when we get to the room, is it easier for the other guy to make the first move or me and my wife or my wife to make the first move?
Any tips welcome to make our first time a sublime experience welcome!
And recently, my wife and someone were flirting… she’s known him 30 years (high school boyfriend) and we invited him over. The presumption by everyone was that they would at least engage in some light. The reality is that he left after about 90 minutes because no one made the first move… we talked, had drinks but he chickened out and my wife was waiting on him. It’s their deal, I’m not involved so I didn’t say anything either. In hindsight, I wish I had just asked, “so, what brings you around this evening?” Just as a way to break open the conversation”
Re: Advice for the first meeting please
All really good advice, I like the round for the room idea and then both taking my wife’s clothes slowly off works for me. I don’t know why that became an issue for me , but it’s all new.
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Re: Advice for the first meeting please
You could suggest that there is alcohol in your room that is free, for him, to continue the party.
If he is nervous I'll make the first move to let him know it is ok with us if he wants to have sex with my wife.
Re: Advice for the first meeting please
Nice ideas!
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Re: Advice for the first meeting please
When will she be ready to do it
Re: Advice for the first meeting please
She is ready and willing now, it’s just a matter of time tables syncing. The wait is painful, especially hearing that she has decided she wants his cum in her mouth (which she rarely did with mine) potentially going to swallow (even rarer!) and she wants to rim him!!
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Re: Advice for the first meeting please
When are you thinking she can meet up with him
Re: Advice for the first meeting please
I hoping for within 4 weeks from now! And it’ll be a bi threesome.
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Re: Advice for the first meeting please
Ditto to everything leggysman said.leggysman wrote: ↑Tue Jun 03, 2025 3:50 amI don't think you should concentrate too much on making the first time feel "natural" from start to finish. The truth is, it's not very natural at first![]()
If they get to a bit of kissing in the bar, then the transition to the room should probably happen fairly organically. If (more likely) the time comes and you're all sitting there feeling a bit nervous and awkward, then someone blurting out "let's go to the room" is as good an ice breaker as any.
Once there, you could suggest that you and he begin undressing your wife together. Some kissing - lips, neck, whatever - depending on who's standing where - and slowly taking off her clothes and then your own.
Once the 'action' starts to happen, things ought to begin to progress pretty naturally, as they do when people start lose their shyness and inhibitions, and get aroused. Once everyone is naked there's not as much to be nervous or awkward about, any more![]()
Our first time went down exactly like leggysman described. We checked into the hotel earlier in the evening and met the guy for drinks afterward in the hotel bar. My wife (Shelley) was very nervous during the conversation, but the guy was somewhat experienced and seemed very at ease. It also helped that they had been chatting for a week or so online and were already acquainted. As for myself, I don't recall feeling nervous, but it did feel a bit surreal and I remember spending a lot of attention trying read Shelley's vibe.
We mostly made small talk (no discussion about sex) for about an hour or so. When he went to the restroom, I asked her if she was okay and if she wanted to go upstairs. She was still very nervous, but smiled and nodded, suggesting it was time to move the party to the room.
I paid the check and we all headed for the elevator together. That's probably when things felt most surreal--walking and talking in the elevator about whatever (the weather? I don't remember now, but it was some ordinary shit), but knowing we were heading to the room with the intention of sex. And I'll never forget her nervous grin as we all talked in the elevator!
When we got settled in the room, I was the one who broke the ice by kissing Shelley as he sat next to her. After a few moments when I sensed her vibe was good, I broke kiss and asked her if she wanted to say hi to our new friend. She turned her head, eyes still closed, and they began to kiss.
The rest was beautiful history.

Omnis deus est. Omnia bona est!
Re: Advice for the first meeting please
That sounds amazing. I think that’s the closest to how I’ve imagined ours unfolding.Greg_N_Shelley wrote: ↑Tue Jun 10, 2025 8:47 amDitto to everything leggysman said.leggysman wrote: ↑Tue Jun 03, 2025 3:50 amI don't think you should concentrate too much on making the first time feel "natural" from start to finish. The truth is, it's not very natural at first![]()
If they get to a bit of kissing in the bar, then the transition to the room should probably happen fairly organically. If (more likely) the time comes and you're all sitting there feeling a bit nervous and awkward, then someone blurting out "let's go to the room" is as good an ice breaker as any.
Once there, you could suggest that you and he begin undressing your wife together. Some kissing - lips, neck, whatever - depending on who's standing where - and slowly taking off her clothes and then your own.
Once the 'action' starts to happen, things ought to begin to progress pretty naturally, as they do when people start lose their shyness and inhibitions, and get aroused. Once everyone is naked there's not as much to be nervous or awkward about, any more![]()
Our first time went down exactly like leggysman described. We checked into the hotel earlier in the evening and met the guy for drinks afterward in the hotel bar. My wife (Shelley) was very nervous during the conversation, but the guy was somewhat experienced and seemed very at ease. It also helped that they had been chatting for a week or so online and were already acquainted. As for myself, I don't recall feeling nervous, but it did feel a bit surreal and I remember spending a lot of attention trying read Shelley's vibe.
We mostly made small talk (no discussion about sex) for about an hour or so. When he went to the restroom, I asked her if she was okay and if she wanted to go upstairs. She was still very nervous, but smiled and nodded, suggesting it was time to move the party to the room.
I paid the check and we all headed for the elevator together. That's probably when things felt most surreal--walking and talking in the elevator about whatever (the weather? I don't remember now, but it was some ordinary shit), but knowing we were heading to the room with the intention of sex. And I'll never forget her nervous grin as we all talked in the elevator!
When we got settled in the room, I was the one who broke the ice by kissing Shelley as he sat next to her. After a few moments when I sensed her vibe was good, I broke kiss and asked her if she wanted to say hi to our new friend. She turned her head, eyes still closed, and they began to kiss.
The rest was beautiful history.![]()
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Re: Advice for the first meeting please
The guy only seemed to know one position (missionary), but Shelley orgasmed three times while he was digging her. I'm not sure if it was his technique, the size of his cock (he was pretty girthy), or how turned on she was with the new scenario. She was very nervous, but I often observed that the more nervous she was beforehand, the more aroused she was once playtime was fully underway.
Here's hoping for a similar experience for the two of you!
Omnis deus est. Omnia bona est!
Re: Advice for the first meeting please
Thanks Greg_N_Shelley for your insight. My wife is also super nervous, but I’m assuming that energy has to go somewhere. It feels as though we are almost talking about the same woman! My wife has always been super shy around sex, but once turned on, that all goes and translates into wildness. She has been chatting with one guy for a couple of weeks, and seems to be the front runner at the moment. All of the things that we’d all like to see have been discussed and I’m so looking forward to it!Greg_N_Shelley wrote: ↑Tue Jun 10, 2025 1:35 pmThe guy only seemed to know one position (missionary), but Shelley orgasmed three times while he was digging her. I'm not sure if it was his technique, the size of his cock (he was pretty girthy), or how turned on she was with the new scenario. She was very nervous, but I often observed that the more nervous she was beforehand, the more aroused she was once playtime was fully underway.
Here's hoping for a similar experience for the two of you!
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Re: Advice for the first meeting please
Agreed, there's definitely some similarities.john1616 wrote: ↑Tue Jun 10, 2025 2:32 pmThanks Greg_N_Shelley for your insight. My wife is also super nervous, but I’m assuming that energy has to go somewhere. It feels as though we are almost talking about the same woman! My wife has always been super shy around sex, but once turned on, that all goes and translates into wildness. She has been chatting with one guy for a couple of weeks, and seems to be the front runner at the moment. All of the things that we’d all like to see have been discussed and I’m so looking forward to it!
Any update on a date for the big night? I don't spend much time on OHW lately, but I would like to check in and see how things go for your first experience.
If you're interested in hearing the entire story about what unfolded once we got to the room, here's a link to a post about it the Library section: viewtopic.php?f=8&t=67426
Omnis deus est. Omnia bona est!
Re: Advice for the first meeting please
No update yet, it’s hinging on our daughter’s baby sitting availability. I will definitely be updating when the big day happens, and thanks for the link to your adventures in the room. I’m going to head there right now!Greg_N_Shelley wrote: ↑Wed Jun 11, 2025 7:19 amAgreed, there's definitely some similarities.john1616 wrote: ↑Tue Jun 10, 2025 2:32 pmThanks Greg_N_Shelley for your insight. My wife is also super nervous, but I’m assuming that energy has to go somewhere. It feels as though we are almost talking about the same woman! My wife has always been super shy around sex, but once turned on, that all goes and translates into wildness. She has been chatting with one guy for a couple of weeks, and seems to be the front runner at the moment. All of the things that we’d all like to see have been discussed and I’m so looking forward to it!
Any update on a date for the big night? I don't spend much time on OHW lately, but I would like to check in and see how things go for your first experience.
If you're interested in hearing the entire story about what unfolded once we got to the room, here's a link to a post about it the Library section: viewtopic.php?f=8&t=67426
Re: Advice for the first meeting please
Hot and hilarious story Greg_N_Shelley. Really hoping ours is as memorable. We’ve discussed how we would like it to go and what we would like to do so much. I’m sure it won’t go to our ‘perfect’ scenario, but just the fact that we are this point is incredible. Your feelings of surrealism are exactly how I’m feeling right now and we haven’t even had our first meeting yet!