PROGRESS report AFTER my wifes FIRST Sensual Massage!!

Myhubbysharesme

Couple
Gold
TLDR recap from previous posts..
Together over 20 year
Married over 15
2 kids
VERY much in love
Wife is reserved and proper
Very open communication
Told her several years ago my greatest fantasy is to share her with another man, her pleasure is my biggest turn on.
She wasnt interested but open to ideas that help satisfy my fantasy while staying within boundaries that she can justify and feel she’s respecting herself.
Took and posted photos/videos on NsFW reddit to hear other guys thoughts on what I believe to be super hot and perfect.. she verified and chose the material to post but keeping very private because of jobs and kids
Talked her into a sensual massage.
She can view it as a massage(and feel good)

I get to see her nude in front of another man and touched on any part of her body by another man for the first time in over 20 years.

Months of planning, compromises and open discussion, she had a full body sensual massage from a guy we found on Reddit, experienced in this, brought a table to the hotel room, used oils, music, room temp.. all the legit stuff.
She kept her thong on, no pussy or asshole touching.. had an amazing experience, got video of him grazing her thong line covering her pussy, his hands wrapped around her large oily breasts …”

Fast forward a little over a month since, and I’m planting the seed for our next step.

She’s made it clear she’ll never ...... with another man but is open to discussing things that turn me on and help satisfy my fantasy desires (she’s fucking amazing)

At the end of the massage I was very turned on with him watching us while he packed up his table and supplies and had moved her to the bed to begin fucking her…

I mentioned another massage but having him watch us fuck in its entirety after the massage

She’s on board with it and said the massage felt good but was still uncomfortable with another man touching her so I framed a new idea as respecting that and will be less uncomfortable if we forego the massage completely….
Have someone join us in a hotel room, to film us while I undress her, foreplay/oral, and fuck.

This way I get to fuck her knowing there’s another guy in the room enjoying the show, he can get all the best angles and I can enjoy it and relive it many times over with the videos after.
To make her feel better I suggested we could wear masks so she’s not worried about this ever getting out and privacy is still honored… she’s going to have further discussion on the details but she’s on board with this being our next experience … 5 years ago I would NEVER thought she’d be good with any of this, and while having much doubt I’ll ever see her shared with another man, these experiences are such a fucking turn on nonetheless… we plan on doing this in several months after we celebrate her birthday and focus on her.. so I have time to find the right person that she would be comfortable with having there while we fuck … some things I plan on approaching with her over that time is the possibility of allowing the third to jerk off while this happens, we fully expect them to be aroused so she won’t be super thrown at this suggestion, I had my cock out stroking the entire time she was being massager and she was aware… so this would be even another step for her to be in the presence of another man’s exposed cock… still thinking of other things to slowly work in that she may be okay with… it’s taken a long time, a lot of patience and open communication but I’m loving the progess… my previous posts have videos of her massage for those interested IMG_1258.jpeg
 
Love this ... Looking forward to seeing future updates on your story I'm in exactly the same boat and often fantasize of the massage scenario but that is all it is at the moment..
Tonight she actually brought up herself about going dogging "letting strangers watch "possibly more" have sex in the car when then weather gets warmer 🥵
 
TLDR recap from previous posts..
Together over 20 year
Married over 15
2 kids
VERY much in love
Wife is reserved and proper
Very open communication
Told her several years ago my greatest fantasy is to share her with another man, her pleasure is my biggest turn on.
She wasnt interested but open to ideas that help satisfy my fantasy while staying within boundaries that she can justify and feel she’s respecting herself.
Took and posted photos/videos on NsFW reddit to hear other guys thoughts on what I believe to be super hot and perfect.. she verified and chose the material to post but keeping very private because of jobs and kids
Talked her into a sensual massage.
She can view it as a massage(and feel good)

I get to see her nude in front of another man and touched on any part of her body by another man for the first time in over 20 years.

Months of planning, compromises and open discussion, she had a full body sensual massage from a guy we found on Reddit, experienced in this, brought a table to the hotel room, used oils, music, room temp.. all the legit stuff.
She kept her thong on, no pussy or asshole touching.. had an amazing experience, got video of him grazing her thong line covering her pussy, his hands wrapped around her large oily breasts …”

Fast forward a little over a month since, and I’m planting the seed for our next step.

She’s made it clear she’ll never ...... with another man but is open to discussing things that turn me on and help satisfy my fantasy desires (she’s fucking amazing)

At the end of the massage I was very turned on with him watching us while he packed up his table and supplies and had moved her to the bed to begin fucking her…

I mentioned another massage but having him watch us fuck in its entirety after the massage

She’s on board with it and said the massage felt good but was still uncomfortable with another man touching her so I framed a new idea as respecting that and will be less uncomfortable if we forego the massage completely….
Have someone join us in a hotel room, to film us while I undress her, foreplay/oral, and fuck.

This way I get to fuck her knowing there’s another guy in the room enjoying the show, he can get all the best angles and I can enjoy it and relive it many times over with the videos after.
To make her feel better I suggested we could wear masks so she’s not worried about this ever getting out and privacy is still honored… she’s going to have further discussion on the details but she’s on board with this being our next experience … 5 years ago I would NEVER thought she’d be good with any of this, and while having much doubt I’ll ever see her shared with another man, these experiences are such a fucking turn on nonetheless… we plan on doing this in several months after we celebrate her birthday and focus on her.. so I have time to find the right person that she would be comfortable with having there while we fuck … some things I plan on approaching with her over that time is the possibility of allowing the third to jerk off while this happens, we fully expect them to be aroused so she won’t be super thrown at this suggestion, I had my cock out stroking the entire time she was being massager and she was aware… so this would be even another step for her to be in the presence of another man’s exposed cock… still thinking of other things to slowly work in that she may be okay with… it’s taken a long time, a lot of patience and open communication but I’m loving the progess… my previous posts have videos of her massage for those interested View attachment 3087439
She is so hot
 
TLDR recap from previous posts..
Together over 20 year
Married over 15
2 kids
VERY much in love
Wife is reserved and proper
Very open communication
Told her several years ago my greatest fantasy is to share her with another man, her pleasure is my biggest turn on.
She wasnt interested but open to ideas that help satisfy my fantasy while staying within boundaries that she can justify and feel she’s respecting herself.
Took and posted photos/videos on NsFW reddit to hear other guys thoughts on what I believe to be super hot and perfect.. she verified and chose the material to post but keeping very private because of jobs and kids
Talked her into a sensual massage.
She can view it as a massage(and feel good)

I get to see her nude in front of another man and touched on any part of her body by another man for the first time in over 20 years.

Months of planning, compromises and open discussion, she had a full body sensual massage from a guy we found on Reddit, experienced in this, brought a table to the hotel room, used oils, music, room temp.. all the legit stuff.
She kept her thong on, no pussy or asshole touching.. had an amazing experience, got video of him grazing her thong line covering her pussy, his hands wrapped around her large oily breasts …”

Fast forward a little over a month since, and I’m planting the seed for our next step.

She’s made it clear she’ll never ...... with another man but is open to discussing things that turn me on and help satisfy my fantasy desires (she’s fucking amazing)

At the end of the massage I was very turned on with him watching us while he packed up his table and supplies and had moved her to the bed to begin fucking her…

I mentioned another massage but having him watch us fuck in its entirety after the massage

She’s on board with it and said the massage felt good but was still uncomfortable with another man touching her so I framed a new idea as respecting that and will be less uncomfortable if we forego the massage completely….
Have someone join us in a hotel room, to film us while I undress her, foreplay/oral, and fuck.

This way I get to fuck her knowing there’s another guy in the room enjoying the show, he can get all the best angles and I can enjoy it and relive it many times over with the videos after.
To make her feel better I suggested we could wear masks so she’s not worried about this ever getting out and privacy is still honored… she’s going to have further discussion on the details but she’s on board with this being our next experience … 5 years ago I would NEVER thought she’d be good with any of this, and while having much doubt I’ll ever see her shared with another man, these experiences are such a fucking turn on nonetheless… we plan on doing this in several months after we celebrate her birthday and focus on her.. so I have time to find the right person that she would be comfortable with having there while we fuck … some things I plan on approaching with her over that time is the possibility of allowing the third to jerk off while this happens, we fully expect them to be aroused so she won’t be super thrown at this suggestion, I had my cock out stroking the entire time she was being massager and she was aware… so this would be even another step for her to be in the presence of another man’s exposed cock… still thinking of other things to slowly work in that she may be okay with… it’s taken a long time, a lot of patience and open communication but I’m loving the progess… my previous posts have videos of her massage for those interested View attachment 3087439
Wow! 🤩 She’s gorgeous, I can record the video.
 
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TLDR recap from previous posts..
Together over 20 year
Married over 15
2 kids
VERY much in love
Wife is reserved and proper
Very open communication
Told her several years ago my greatest fantasy is to share her with another man, her pleasure is my biggest turn on.
She wasnt interested but open to ideas that help satisfy my fantasy while staying within boundaries that she can justify and feel she’s respecting herself.
Took and posted photos/videos on NsFW reddit to hear other guys thoughts on what I believe to be super hot and perfect.. she verified and chose the material to post but keeping very private because of jobs and kids
Talked her into a sensual massage.
She can view it as a massage(and feel good)

I get to see her nude in front of another man and touched on any part of her body by another man for the first time in over 20 years.

Months of planning, compromises and open discussion, she had a full body sensual massage from a guy we found on Reddit, experienced in this, brought a table to the hotel room, used oils, music, room temp.. all the legit stuff.
She kept her thong on, no pussy or asshole touching.. had an amazing experience, got video of him grazing her thong line covering her pussy, his hands wrapped around her large oily breasts …”

Fast forward a little over a month since, and I’m planting the seed for our next step.

She’s made it clear she’ll never ...... with another man but is open to discussing things that turn me on and help satisfy my fantasy desires (she’s fucking amazing)

At the end of the massage I was very turned on with him watching us while he packed up his table and supplies and had moved her to the bed to begin fucking her…

I mentioned another massage but having him watch us fuck in its entirety after the massage

She’s on board with it and said the massage felt good but was still uncomfortable with another man touching her so I framed a new idea as respecting that and will be less uncomfortable if we forego the massage completely….
Have someone join us in a hotel room, to film us while I undress her, foreplay/oral, and fuck.

This way I get to fuck her knowing there’s another guy in the room enjoying the show, he can get all the best angles and I can enjoy it and relive it many times over with the videos after.
To make her feel better I suggested we could wear masks so she’s not worried about this ever getting out and privacy is still honored… she’s going to have further discussion on the details but she’s on board with this being our next experience … 5 years ago I would NEVER thought she’d be good with any of this, and while having much doubt I’ll ever see her shared with another man, these experiences are such a fucking turn on nonetheless… we plan on doing this in several months after we celebrate her birthday and focus on her.. so I have time to find the right person that she would be comfortable with having there while we fuck … some things I plan on approaching with her over that time is the possibility of allowing the third to jerk off while this happens, we fully expect them to be aroused so she won’t be super thrown at this suggestion, I had my cock out stroking the entire time she was being massager and she was aware… so this would be even another step for her to be in the presence of another man’s exposed cock… still thinking of other things to slowly work in that she may be okay with… it’s taken a long time, a lot of patience and open communication but I’m loving the progess… my previous posts have videos of her massage for those interested View attachment 3087439
Love it. She is very sexy!
 
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Reactions: Myhubbysharesme
TLDR recap from previous posts..
Together over 20 year
Married over 15
2 kids
VERY much in love
Wife is reserved and proper
Very open communication
Told her several years ago my greatest fantasy is to share her with another man, her pleasure is my biggest turn on.
She wasnt interested but open to ideas that help satisfy my fantasy while staying within boundaries that she can justify and feel she’s respecting herself.
Took and posted photos/videos on NsFW reddit to hear other guys thoughts on what I believe to be super hot and perfect.. she verified and chose the material to post but keeping very private because of jobs and kids
Talked her into a sensual massage.
She can view it as a massage(and feel good)

I get to see her nude in front of another man and touched on any part of her body by another man for the first time in over 20 years.

Months of planning, compromises and open discussion, she had a full body sensual massage from a guy we found on Reddit, experienced in this, brought a table to the hotel room, used oils, music, room temp.. all the legit stuff.
She kept her thong on, no pussy or asshole touching.. had an amazing experience, got video of him grazing her thong line covering her pussy, his hands wrapped around her large oily breasts …”

Fast forward a little over a month since, and I’m planting the seed for our next step.

She’s made it clear she’ll never ...... with another man but is open to discussing things that turn me on and help satisfy my fantasy desires (she’s fucking amazing)

At the end of the massage I was very turned on with him watching us while he packed up his table and supplies and had moved her to the bed to begin fucking her…

I mentioned another massage but having him watch us fuck in its entirety after the massage

She’s on board with it and said the massage felt good but was still uncomfortable with another man touching her so I framed a new idea as respecting that and will be less uncomfortable if we forego the massage completely….
Have someone join us in a hotel room, to film us while I undress her, foreplay/oral, and fuck.

This way I get to fuck her knowing there’s another guy in the room enjoying the show, he can get all the best angles and I can enjoy it and relive it many times over with the videos after.
To make her feel better I suggested we could wear masks so she’s not worried about this ever getting out and privacy is still honored… she’s going to have further discussion on the details but she’s on board with this being our next experience … 5 years ago I would NEVER thought she’d be good with any of this, and while having much doubt I’ll ever see her shared with another man, these experiences are such a fucking turn on nonetheless… we plan on doing this in several months after we celebrate her birthday and focus on her.. so I have time to find the right person that she would be comfortable with having there while we fuck … some things I plan on approaching with her over that time is the possibility of allowing the third to jerk off while this happens, we fully expect them to be aroused so she won’t be super thrown at this suggestion, I had my cock out stroking the entire time she was being massager and she was aware… so this would be even another step for her to be in the presence of another man’s exposed cock… still thinking of other things to slowly work in that she may be okay with… it’s taken a long time, a lot of patience and open communication but I’m loving the progess… my previous posts have videos of her massage for those interested View attachment 3087439
wow she's hot! What an incredible story!
 
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Reactions: Myhubbysharesme
TLDR recap from previous posts..
Together over 20 year
Married over 15
2 kids
VERY much in love
Wife is reserved and proper
Very open communication
Told her several years ago my greatest fantasy is to share her with another man, her pleasure is my biggest turn on.
She wasnt interested but open to ideas that help satisfy my fantasy while staying within boundaries that she can justify and feel she’s respecting herself.
Took and posted photos/videos on NsFW reddit to hear other guys thoughts on what I believe to be super hot and perfect.. she verified and chose the material to post but keeping very private because of jobs and kids
Talked her into a sensual massage.
She can view it as a massage(and feel good)

I get to see her nude in front of another man and touched on any part of her body by another man for the first time in over 20 years.

Months of planning, compromises and open discussion, she had a full body sensual massage from a guy we found on Reddit, experienced in this, brought a table to the hotel room, used oils, music, room temp.. all the legit stuff.
She kept her thong on, no pussy or asshole touching.. had an amazing experience, got video of him grazing her thong line covering her pussy, his hands wrapped around her large oily breasts …”

Fast forward a little over a month since, and I’m planting the seed for our next step.

She’s made it clear she’ll never ...... with another man but is open to discussing things that turn me on and help satisfy my fantasy desires (she’s fucking amazing)

At the end of the massage I was very turned on with him watching us while he packed up his table and supplies and had moved her to the bed to begin fucking her…

I mentioned another massage but having him watch us fuck in its entirety after the massage

She’s on board with it and said the massage felt good but was still uncomfortable with another man touching her so I framed a new idea as respecting that and will be less uncomfortable if we forego the massage completely….
Have someone join us in a hotel room, to film us while I undress her, foreplay/oral, and fuck.

This way I get to fuck her knowing there’s another guy in the room enjoying the show, he can get all the best angles and I can enjoy it and relive it many times over with the videos after.
To make her feel better I suggested we could wear masks so she’s not worried about this ever getting out and privacy is still honored… she’s going to have further discussion on the details but she’s on board with this being our next experience … 5 years ago I would NEVER thought she’d be good with any of this, and while having much doubt I’ll ever see her shared with another man, these experiences are such a fucking turn on nonetheless… we plan on doing this in several months after we celebrate her birthday and focus on her.. so I have time to find the right person that she would be comfortable with having there while we fuck … some things I plan on approaching with her over that time is the possibility of allowing the third to jerk off while this happens, we fully expect them to be aroused so she won’t be super thrown at this suggestion, I had my cock out stroking the entire time she was being massager and she was aware… so this would be even another step for her to be in the presence of another man’s exposed cock… still thinking of other things to slowly work in that she may be okay with… it’s taken a long time, a lot of patience and open communication but I’m loving the progess… my previous posts have videos of her massage for those interested View attachment 3087439
What a beautiful, sensual woman you have there! Please keep us updated. Does she know you're on this site? it mighthelp the fantasy come closer to reality if she's on here with youu andrealizes how many couples share this lefestyle. Love her body!!
 
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TLDR recap from previous posts..
Together over 20 year
Married over 15
2 kids
VERY much in love
Wife is reserved and proper
Very open communication
Told her several years ago my greatest fantasy is to share her with another man, her pleasure is my biggest turn on.
She wasnt interested but open to ideas that help satisfy my fantasy while staying within boundaries that she can justify and feel she’s respecting herself.
Took and posted photos/videos on NsFW reddit to hear other guys thoughts on what I believe to be super hot and perfect.. she verified and chose the material to post but keeping very private because of jobs and kids
Talked her into a sensual massage.
She can view it as a massage(and feel good)

I get to see her nude in front of another man and touched on any part of her body by another man for the first time in over 20 years.

Months of planning, compromises and open discussion, she had a full body sensual massage from a guy we found on Reddit, experienced in this, brought a table to the hotel room, used oils, music, room temp.. all the legit stuff.
She kept her thong on, no pussy or asshole touching.. had an amazing experience, got video of him grazing her thong line covering her pussy, his hands wrapped around her large oily breasts …”

Fast forward a little over a month since, and I’m planting the seed for our next step.

She’s made it clear she’ll never ...... with another man but is open to discussing things that turn me on and help satisfy my fantasy desires (she’s fucking amazing)

At the end of the massage I was very turned on with him watching us while he packed up his table and supplies and had moved her to the bed to begin fucking her…

I mentioned another massage but having him watch us fuck in its entirety after the massage

She’s on board with it and said the massage felt good but was still uncomfortable with another man touching her so I framed a new idea as respecting that and will be less uncomfortable if we forego the massage completely….
Have someone join us in a hotel room, to film us while I undress her, foreplay/oral, and fuck.

This way I get to fuck her knowing there’s another guy in the room enjoying the show, he can get all the best angles and I can enjoy it and relive it many times over with the videos after.
To make her feel better I suggested we could wear masks so she’s not worried about this ever getting out and privacy is still honored… she’s going to have further discussion on the details but she’s on board with this being our next experience … 5 years ago I would NEVER thought she’d be good with any of this, and while having much doubt I’ll ever see her shared with another man, these experiences are such a fucking turn on nonetheless… we plan on doing this in several months after we celebrate her birthday and focus on her.. so I have time to find the right person that she would be comfortable with having there while we fuck … some things I plan on approaching with her over that time is the possibility of allowing the third to jerk off while this happens, we fully expect them to be aroused so she won’t be super thrown at this suggestion, I had my cock out stroking the entire time she was being massager and she was aware… so this would be even another step for her to be in the presence of another man’s exposed cock… still thinking of other things to slowly work in that she may be okay with… it’s taken a long time, a lot of patience and open communication but I’m loving the progess… my previous posts have videos of her massage for those interested View attachment 3087439
Love this story and look forward to hearing more on your progress. You have an incredible wife.
 
Thanks for the detailed update, man. It's really hot to read your progress after 20+ years together. The fact that she's slowly opening up while staying true to her own boundaries shows how strong your communication and your love for each other really is.

One thing that strikes me when I look at the photo (especially her breasts) is that she seems to have had breast reduction surgery at some point (or something). One of my ex had a similar surgery and she was having mixed feelings about her body. She never told me directly but she did not like her body much.

I get the impression that your wife's biggest internal block isn't really the idea of another man... it's that she doesn't love her own body enough yet. She's reserved and proper, as you said, and that often comes with deep self-consciousness. Even though she enjoys the massage and is now open to being filmed while you fuck her, she's still protecting herself a lot (thong on, no direct touching, masks for privacy, etc.).

My suggestion for the next several months (while you prepare for her birthday and this new experience):

Instead of rushing straight to the "filming with a guy watching/jerking" step, put a big part of your energy into rebuilding her self-confidence and her love for her own body first. Make her feel incredibly desired and beautiful as she is right now. Compliment her breasts specifically in a loving, lustful way — tell her how much you love their shape, how they feel in your hands, how sexy they look when they're oiled and moving, etc. Overdo the praise in a genuine way (or whatever part of her body she doesn't like much).

The more she starts loving her own body and feeling sexy in it, the less she'll need to hide behind "this is just for your fantasy" justifications. She'll become more comfortable being seen and admired.

Practical ideas:
- Encourage her (little by little) to dress sexier in daily life and when you go out — tighter tops, nicer lingerie, outfits that show a bit more cleavage. Always frame it as "you look so fucking hot like this, it drives me crazy."
- Take lots of private photos and videos of her just for the two of you, and show her how much you jerk off to them.
- When the third guy eventually watches you fuck her, she'll feel much prouder and more turned on if she already feels good in her skin.
You've already done an amazing job with patience and communication. If you now actively work on making her fall in love with her own body again, I think the rest (including going further in the future) will flow much more naturally and with less discomfort for her.

She's lucky to have a husband who wants her pleasure so much. Keep us updated!
 
TLDR recap from previous posts..
Together over 20 year
Married over 15
2 kids
VERY much in love
Wife is reserved and proper
Very open communication
Told her several years ago my greatest fantasy is to share her with another man, her pleasure is my biggest turn on.
She wasnt interested but open to ideas that help satisfy my fantasy while staying within boundaries that she can justify and feel she’s respecting herself.
Took and posted photos/videos on NsFW reddit to hear other guys thoughts on what I believe to be super hot and perfect.. she verified and chose the material to post but keeping very private because of jobs and kids
Talked her into a sensual massage.
She can view it as a massage(and feel good)

I get to see her nude in front of another man and touched on any part of her body by another man for the first time in over 20 years.

Months of planning, compromises and open discussion, she had a full body sensual massage from a guy we found on Reddit, experienced in this, brought a table to the hotel room, used oils, music, room temp.. all the legit stuff.
She kept her thong on, no pussy or asshole touching.. had an amazing experience, got video of him grazing her thong line covering her pussy, his hands wrapped around her large oily breasts …”

Fast forward a little over a month since, and I’m planting the seed for our next step.

She’s made it clear she’ll never ...... with another man but is open to discussing things that turn me on and help satisfy my fantasy desires (she’s fucking amazing)

At the end of the massage I was very turned on with him watching us while he packed up his table and supplies and had moved her to the bed to begin fucking her…

I mentioned another massage but having him watch us fuck in its entirety after the massage

She’s on board with it and said the massage felt good but was still uncomfortable with another man touching her so I framed a new idea as respecting that and will be less uncomfortable if we forego the massage completely….
Have someone join us in a hotel room, to film us while I undress her, foreplay/oral, and fuck.

This way I get to fuck her knowing there’s another guy in the room enjoying the show, he can get all the best angles and I can enjoy it and relive it many times over with the videos after.
To make her feel better I suggested we could wear masks so she’s not worried about this ever getting out and privacy is still honored… she’s going to have further discussion on the details but she’s on board with this being our next experience … 5 years ago I would NEVER thought she’d be good with any of this, and while having much doubt I’ll ever see her shared with another man, these experiences are such a fucking turn on nonetheless… we plan on doing this in several months after we celebrate her birthday and focus on her.. so I have time to find the right person that she would be comfortable with having there while we fuck … some things I plan on approaching with her over that time is the possibility of allowing the third to jerk off while this happens, we fully expect them to be aroused so she won’t be super thrown at this suggestion, I had my cock out stroking the entire time she was being massager and she was aware… so this would be even another step for her to be in the presence of another man’s exposed cock… still thinking of other things to slowly work in that she may be okay with… it’s taken a long time, a lot of patience and open communication but I’m loving the progess… my previous posts have videos of her massage for those interested View attachment 3087439
I’m very interested. Also, my gut tells me that if she does allow the right guy to come and film from every near angle, view, etc. and if you could discuss privately with him about being vocally expressive about asking for a few wild sexual positions as y’all are doing it along with making his own excitement known but not being creepy?
Have him plan just before you climax to make some gesture and comment about not being able to stand it and openly holding his own cock to finish himself off, she mighhhhht possibly agree if you suggest in the heat of the moment that he come over and cum on her feet or something?
That may be way out in left field but if it worked it would be a huge step and if it were me, also a huge turn on. 🥜💦
 
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Where do we find these stud massage guys for joining us. A massage is the only way I’m gonna be able to get my wife to go through with a threesome and I know the right, good looking, well hung “therapist” is gonna have a fairly easy time once we’re in that situation and the two of us have her warmed up!
Serious question btw? Where do you guys suggest searching? We’re near Huntsville, Alabama btw. Thanks
 
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Thanks for the detailed update, man. It's really hot to read your progress after 20+ years together. The fact that she's slowly opening up while staying true to her own boundaries shows how strong your communication and your love for each other really is.

One thing that strikes me when I look at the photo (especially her breasts) is that she seems to have had breast reduction surgery at some point (or something). One of my ex had a similar surgery and she was having mixed feelings about her body. She never told me directly but she did not like her body much.

I get the impression that your wife's biggest internal block isn't really the idea of another man... it's that she doesn't love her own body enough yet. She's reserved and proper, as you said, and that often comes with deep self-consciousness. Even though she enjoys the massage and is now open to being filmed while you fuck her, she's still protecting herself a lot (thong on, no direct touching, masks for privacy, etc.).

My suggestion for the next several months (while you prepare for her birthday and this new experience):

Instead of rushing straight to the "filming with a guy watching/jerking" step, put a big part of your energy into rebuilding her self-confidence and her love for her own body first. Make her feel incredibly desired and beautiful as she is right now. Compliment her breasts specifically in a loving, lustful way — tell her how much you love their shape, how they feel in your hands, how sexy they look when they're oiled and moving, etc. Overdo the praise in a genuine way (or whatever part of her body she doesn't like much).

The more she starts loving her own body and feeling sexy in it, the less she'll need to hide behind "this is just for your fantasy" justifications. She'll become more comfortable being seen and admired.

Practical ideas:
- Encourage her (little by little) to dress sexier in daily life and when you go out — tighter tops, nicer lingerie, outfits that show a bit more cleavage. Always frame it as "you look so fucking hot like this, it drives me crazy."
- Take lots of private photos and videos of her just for the two of you, and show her how much you jerk off to them.
- When the third guy eventually watches you fuck her, she'll feel much prouder and more turned on if she already feels good in her skin.
You've already done an amazing job with patience and communication. If you now actively work on making her fall in love with her own body again, I think the rest (including going further in the future) will flow much more naturally and with less discomfort for her.

She's lucky to have a husband who wants her pleasure so much. Keep us updated!
Hey.. thank you for the detailed response! She had a reduction at 18.. 22 years later she’s very comfortable with her body.. we have over 400 pics and videos of which we take new ones every week… I tell her every chance I get how perfect I find her body and I believe it helped reinforce that several years back when she began choosing photos to post on reddit… she also likes choosing new lingerie sets to wear for me, she knows I find her breasts perfect and she’s in no way insecure over them, nor should she be…. Her biggest block is definitely the idea of another man and her moral compass moving past the idea of it feeling like cheating to her… I’ve explained that cheating is a betrayal of trust and I trust her more than anyone, and this is what I want so she’s not going behind me back.
 
Hey.. thank you for the detailed response! She had a reduction at 18.. 22 years later she’s very comfortable with her body.. we have over 400 pics and videos of which we take new ones every week… I tell her every chance I get how perfect I find her body and I believe it helped reinforce that several years back when she began choosing photos to post on reddit… she also likes choosing new lingerie sets to wear for me, she knows I find her breasts perfect and she’s in no way insecure over them, nor should she be…. Her biggest block is definitely the idea of another man and her moral compass moving past the idea of it feeling like cheating to her… I’ve explained that cheating is a betrayal of trust and I trust her more than anyone, and this is what I want so she’s not going behind me back.
She’s actually all on board with the filming and fucking, I’m actively working on another idea to expland on that, she’s sat it on for a couple days, we’re discussing tonight and if it works out, I’ll be providing another update with this new possibility
 
I’m very interested. Also, my gut tells me that if she does allow the right guy to come and film from every near angle, view, etc. and if you could discuss privately with him about being vocally expressive about asking for a few wild sexual positions as y’all are doing it along with making his own excitement known but not being creepy?
Have him plan just before you climax to make some gesture and comment about not being able to stand it and openly holding his own cock to finish himself off, she mighhhhht possibly agree if you suggest in the heat of the moment that he come over and cum on her feet or something?
That may be way out in left field but if it worked it would be a huge step and if it were me, also a huge turn on. 🥜💦
I actually brought another idea to her this week to expland on the video idea, that the person who’s recording will obviously be aroused, and will very likely be stroking his own cock, and presented the idea of her reaching out and stroking him while im fucking her. She’s contemplating the idea and thinking if she could get her head around the idea, as well as any follow-up questions for me to discusss with each other tonight