Wife's First Time? Hopefully.

[justlookin2day]

Hi All,
I think it is about time that I start a thread as much for me as for this great community. I've been interested in having a hotwife/cuckold relationship for the last two years and I think my wife will likely sleep with another man or men in the next few days.
She is meeting four of her friends for a girls trip to NYC and has been talking and texting with two of her former lovers. One was a long-term fwb she had in her twenties and the other was a friend she slept with one time during the same period of her life. Several months ago on another trip to NYC she met up with the friend she slept with one time at her hotel. Unfortunately on that trip she was sharing a room with her friend so they did not sleep together, but they did kiss and touch each other. This time I have booked a large suite for her in a separate hotel from her friends so she will feel free to go as far a she is comfortable.
She leaves tomorrow morning so I will update this thread as things happen. I found her last trip incredibly arousing so I'm hoping I have a similar reaction this time.

[tit5atat]

Sounds exciting! Please share how it goes.
How did all this lead up to where you are now? You asked her to cuck you? What made her make up her mind to do this?

[Pecannut]

Sounds awesome! Hope everything goes well and she enjoys herself in NYC.

[Wantsomefunto]

Great first post! Hope she keeps you informed how things go. Is she going to send you pics? Love to know more about her and you.

[Johnann2227]

Well, you have done everything you can to support her, now it is up to her. Hopefully she will take that liberating first step and fuck her friend. If she does, regardless of what you have previously said, she will have doubts about what she has done. While she is away go and buy her a lovely piece of jewellery. When she gets back give it to her and tell it signifies your love and commitment to her. A charm bracelet is good. Put a heart charm on it. Tell her that each time she sleeps with a new guy you will add a new charm. This will ease her doubts. Good luck and hopefully welcome to our lifestyle.

[justlookin2day]

Sounds exciting! Please share how it goes.
How did all this lead up to where you are now? You asked her to cuck you? What made her make up her mind to do this?

I think this all began when I started getting turned on by stories of her past relationships. We have known each other since university but did not start dating until out late twenties. Since I knew her as a friend I knew she had been with many men, most of whom were very athletic, tall and successful. She is very smart and beautiful so she was almost always the center of attention and had her pick of men. For some reason after 15 years together I asked her for sexy stories from her past and I loved them.

For me at least this evolved to wanting to see her with other men, which she was of course reluctant to even discuss. But over the past year or so she has come around. Her biggest concern was that I was using this to sleep with other women. Once she understood that was the last thing I wanted she quickly came around to the idea.

[justlookin2day]

Great first post! Hope she keeps you informed how things go. Is she going to send you pics? Love to know more about her and you.

We are both operating under the assumption that she will be with one of the two friends in the next few days. If she does I will definitely receive pictures that she will take before and after showing what she is wearing, etc. I would be surprised if on this first go around I receive pictures of her and the guy together. She said she would try to get him to take a picture while she is giving him head, or penetrating her but I think that is too much to ask for on her first time.

[justlookin2day]

Well, you have done everything you can to support her, now it is up to her. Hooefully she will take that liberating first step and fuck her friend. If she does, regardless of what you have previously said, she will have doubts about what she has done. While she is away go and by her a lovely piece of jewellery. When she gets back give it to her and tell it signifies your love and commitment to her. A charm bracelet is good. Put a heart charm on it. Tell her that each time she sleeps with a new guy you will add a new charm. This will ease her doubts. Good luck and hopefully welcome to our lifestyle.

It really is crazy for me to think that I will be a cuckold in the next few days. I dropped her off at the airport this morning and she certainly feels confident that she will proceed. She even texted me that she was getting more looks and eye contact than normal. I told her it is likely because she is now sexually available.

My goal is to be supportive and not allow any jealousy or angst to to impact my wife. I think as long as I control myself she will be happy and not feel too much guilt. I asked if she felt any guilt after her last trip to NYC when she kissed another man and she said "No, because she knew I would like it". Obviously kissing and fucking are very different!

As for a gift, I have already purchased a very nice Cartier bracelet for her when she returns.

[ucaneffher]

I'm starting to really get jealous of all these different hot stories of you guys having your lovely ladies go off on trips to most likely have sex. First I read about the Florida thread and now you post about your wife heading to NYC where she will likely get dicked down in a large suite.

When am I gonna catch my break and join all of you with some hot experiences?!

Anyway, I hope that she has a blast and feels comfortable going all the way once she is there. Hope that it is everything that you expect and that you both get addicted to it. Please keep us updated with details! Hope she comes back as a new liberated woman needing constant male attention

[justlookin2day]

My wife called me last night and she is settled in at the hotel. She is definitely nervous about today and said she did not want to disappoint me. Of course I told her that I will not be disappointed no matter what happens. All of us know this is not entirely true!!
With her being with friends all day, we will not have too many chances to talk so I'm going to keep myself busy with work and see how the night progresses.

[justlookin2day]

My wife told me that J (The friend she made out with last time she was in NYC) was on his way over to the hotel. Haven't received any response to my three text messages since then, two of which were immediate responses to her text. Will not reach out again until she does, as I certainly don't want to interrupt them. Fingers crossed!!

[slenderfish]

Hi Just look -

I remember doing this almost exact same effort (hotel,etc.) for my wife when she was embarking.

There was this balance between her remaining "in the moment" with her first guy vs. being aware of me and my part of it. I was hoping for an update immediately "after the encounter" and she did not want to disappoint, while enjoying her time and moment.

We agreed on a workaround. She called my mobile immediately after and I agreed not to pick up; rather, we both wanted it to go to voicemail. She left a very lovely and compelling message, and was able to close the call and go back to herself. I was able to listen to it, immediately after the fact, and to keep it for posterity (e.g. listening to it again and again to hear different nuances each time. And, of course, still have it (and a couple others)!

Just a suggestion.

[justlookin2day]

I did not get a full rundown of what happened yesterday, but what I do know is that they met up in my wife's hotel room and she gave him a bj and swallowed his load. She is with her friends all day sightseeing and she was happy to give me more details immediately but to be honest I didn't want to miss the details as there was a lot of background noise as is always the case in NYC. She is going to call me later when she is in her hotel room with more details. She seemed a little nervous of how I would react to what she did but of course I was supportive. The only question I really asked was if she enjoyed it. She said she ,"enjoyed the physical part a lot." I guess I will learn what that means later.

[justlookin2day]

One quick thing to add. Although my wife and I have sex often, I only get one or two blow jobs a year and never to completion. She has probably not swallowed my cum for a decade. I really like the idea that she will be doing things with other men that she does not do with me. I think that is why I posted in the cuckold forum rather than the hot wives forum. Do you guys agree?

[Harley1515]

Sounds hot too bad you couldn’t be there to watch him have your wife and for her to use his cock for her pleasure

[myoralannie]

Have you both discussed bareback or condom and are you interested in cleaning her?

[isinlarsa]

One quick thing to add. Although my wife and I have sex often, I only get one or two blow jobs a year and never to completion. She has probably not swallowed my cum for a decade. I really like the idea that she will be doing things with other men that she does not do with me. I think that is why I posted in the cuckold forum rather than the hot wives forum. Do you guys agree?

She is my hotwife, and I am her cuckold. I'm not into extreme things, like humiliation and the like; but I, too, do like it when she does things with other men that she does not do with me.

[justlookin2day]

Have you both discussed bareback or condom and are you interested in cleaning her?

She told me she has no interest in using condoms for oral sex but will use condoms for intercourse. I think this will be the rule unless she gets a regular bull. As for creampie cleanup, I don’t currently have any interest in it, but I am definitely turned on thinking about eating her pussy immediately after she is fucked.
However I think that if I watch my wife with another man or men I will be so turned on my wife could get me to do almost anything. I think she knows this because she has said that when I get to watch she does not want me to masturbate until they are finished. She is worried if I cum that I might interrupt her play.

[justlookin2day]

Sounds hot too bad you couldn’t be there to watch him have your wife and for her to use his cock for her pleasure

I don’t really believe I will watch my wife with other men for quite a while. Once she is comfortable cuckolding me then I will be able to watch and I am really looking forward to it. Hoping to start getting pics and videos within the next few months.
And she did not cum. Just swallowed his load which is what she told me she expected to do her first time.

[justlookin2day]

My wife met with her long-term fwb (I'll call him Sam) from before we were married yesterday. Most of their time together occurred in my wife's hotel although it started with them walking around NYC. Once they got to the hotel she texted me letting me know they were chatting on the couch and that was all the communication I had from her for almost 2.5 hours.

During this time I became increasingly convinced that she was having her second sexual experience in two days which really blew my mind. As far as I know she has not touched another man's cock in 15+ years and now she has touched two in less than 30 hours?? I was more turned on than I have been for years imagining what they were doing. It is important to know that she kept Sam as her fwb for years because he was a very good lover and she came multiple times almost every time they were together.

She called me after Sam left to tell me what had happened and what they discussed, but prefaced it saying that nothing had happened.

She told him about our new situation and she said Sam is definitely interested, even saying that the few times they have met socially since we were married that he had been aroused by her. The big news is that Sam is in an open-relationship, but their rule is that they must discuss any new relationship with the other before proceeding. At this point I understood why they did not have sex and just asked questions about how she felt, was she interested in him and if she expects them to meet in the future for sex. Her answer was that yes, she is interested, she expected to meet him for sex in the future and that if not for their "rule" that they definitely would have fucked last night.

My response to her was very supportive, saying how much I liked what she is doing and that I was excited for the future. I also wanted to make sure that she does not feel pressured by me to be with other men and she assured me that she really is enjoying herself, even though it is strange for her. She says her favorite thing so far is how attracted these men are to her and how much they seem to desire her.

At this point she needed to jump off the phone as it was time to meet her friends for a late dinner. As I was saying good bye I asked how she and Sam said good bye and she said they kissed. Of course I responded asking if it was a friendly kiss or something more. She said it was a little more than friendly so I asked if tongue was involved to which she quietly said "yes". After a few more questions and some back and forth she admitted that as he was about to leave, they made out, touched each other everywhere without taking off their clothes and that she had rubbed his hard cock through his pants.

I asked her how their last moments together amounted to nothing and she responded that it seems so strange to to talk about making-out with another man with me, her husband. I was very understanding and did not get upset but reiterated that this is what I want to hear about. Is this common for women starting out? I mean two days ago she had a cock in her mouth and swallowed his cum and yesterday she is hesitant to tell me about making out with another guy?

[myoralannie]

Good luck trying to figure that out. This is my issue as well only somewhat deeper and more difficult. I suppose the pundits on HWing would tell you to let it breathe, which is probably correct. I feel like the more time that comes between the act and her sharing it w/ you reinforces that you are both not in it together. I have had read very good advice from a lot of folks on here so you came to the right place.
Good luck. It sounds like the start of a lot of fun.

[isinlarsa]

My wife met with her long-term fwb (I'll call him Sam) from before we were married yesterday. Most of their time together occurred in my wife's hotel although it started with them walking around NYC. Once they got to the hotel she texted me letting me know they were chatting on the couch and that was all the communication I had from her for almost 2.5 hours.

During this time I became increasingly convinced that she was having her second sexual experience in two days which really blew my mind. As far as I know she has not touched another man's cock in 15+ years and now she has touched two in less than 30 hours?? I was more turned on than I have been for years imagining what they were doing. It is important to know that she kept Sam as her fwb for years because he was a very good lover and she came multiple times almost every time they were together.

She called me after Sam left to tell me what had happened and what they discussed, but prefaced it saying that nothing had happened.

She told him about our new situation and she said Sam is definitely interested, even saying that the few times they have met socially since we were married that he had been aroused by her. The big news is that Sam is in an open-relationship, but their rule is that they must discuss any new relationship with the other before proceeding. At this point I understood why they did not have sex and just asked questions about how she felt, was she interested in him and if she expects them to meet in the future for sex. Her answer was that yes, she is interested, she expected to meet him for sex in the future and that if not for their "rule" that they definitely would have fucked last night.

My response to her was very supportive, saying how much I liked what she is doing and that I was excited for the future. I also wanted to make sure that she does not feel pressured by me to be with other men and she assured me that she really is enjoying herself, even though it is strange for her. She says her favorite thing so far is how attracted these men are to her and how much they seem to desire her.

At this point she needed to jump off the phone as it was time to meet her friends for a late dinner. As I was saying good bye I asked how she and Sam said good bye and she said they kissed. Of course I responded asking if it was a friendly kiss or something more. She said it was a little more than friendly so I asked if tongue was involved to which she quietly said "yes". After a few more questions and some back and forth she admitted that as he was about to leave, they made out, touched each other everywhere without taking off their clothes and that she had rubbed his hard cock through his pants.

I asked her how their last moments together amounted to nothing and she responded that it seems so strange to to talk about making-out with another man with me, her husband. I was very understanding and did not get upset but reiterated that this is what I want to hear about. Is this common for women starting out? I mean two days ago she had a cock in her mouth and swallowed his cum and yesterday she is hesitant to tell me about making out with another guy?

Women's minds work differently than us guys. She may have been reluctant to tell about just French kissing with the second guy, because she may have been concerned about how you would feel about her moving from one guy to another in such a short period of time; even though things they did were mild. From what I understand from your post is they did discuss actually having sex with each other once he clears it with his Significant Other.

[justlookin2day]

isinlarsa: I think you may be right that she felt a little slutty for going from one guy to the next so quickly. She told me this morning that she is going to try to convince Sam to come to her hotel tonight. This time definitely to fuck. He is busy with his significant other so he really should not come. He did text that she is "killing him" as he wants her so badly, so she will do her best to tempt him. She really wants this now so I'm hoping tonight is the night she spreads her legs for another man. If not, we are going on a family trip to NYC in July so worst case it will happen then.

[isinlarsa]

I hope he can clear it with his SO, so your wife gets fucked tonight.

If it doesn't happen until July, will the fact it is a family trip complicate things? Are you and she coming up with a cover story, so she can get together with him?

Of course, it can happen tonight and again in July.

[justlookin2day]

I hope he can clear it with his SO, so your wife gets fucked tonight.

If it doesn't happen until July, will the fact it is a family trip complicate things? Are you and she coming up with a cover story, so she can get together with him?

Of course, it can happen tonight and again in July.

I think it will definitely happen in July regardless. We will stay in a hotel with our young kids so my plan would be to get an extra room for her to play on a separate floor. I would stay with the kid's while she goes off to see "friends" which would not be unusual as she lived in NYC for several years and keeps in touch with people there.
I think it will really feed into my fantasies if I care for the kids while several floors away she is entertaining another man.