Wife's First Time? Hopefully.

For cuckoldresses and the men who serve them.
isinlarsa
OHW Addict
Posts: 2220
Joined: Thu Mar 31, 2016 5:44 am

Re: Wife's First Time? Hopefully.

Unread post by isinlarsa » Sat Jun 08, 2024 12:25 pm

justlookin2day wrote:
Sat Jun 08, 2024 12:17 pm
isinlarsa wrote:
Sat Jun 08, 2024 12:05 pm
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 we 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.
I agree. One of my hottest experiences was taking our daughter out for the evening so my wife could take her young black stud into our marital bed and for him to fuck her for the first time. How many kids do you have and what are their ages? It is so hot for young mothers to get fucked by other men.

isinlarsa
OHW Addict
Posts: 2220
Joined: Thu Mar 31, 2016 5:44 am

Re: Wife's First Time? Hopefully.

Unread post by isinlarsa » Sat Jun 08, 2024 12:32 pm

Any plans for her also to get together in July with the guy she gave the blow job to? It would be so hot for you to be off with the kids whlle she entertains each man in her extra room.

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Sat Jun 08, 2024 12:37 pm

myoralannie wrote:
Sat Jun 08, 2024 6:44 am
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.
I read your posts and your situation does seem difficult. It suppose we have to make concessions to our women in order to have them sleep with men outside of our marriages. How crazy does that sentence sound!!

On this forum some cuckolds say they don't understand why men allow their women to play alone, because then we get nothing out of it. For my wife, having me in the room is a non-starter. If I don't agree to her playing solo to start then I will never have a hotwife and will never see a video, picture or live performance of her with another man. I just have to believe that with experience her perspective will change.

Good luck and thank you for your advice. I fell like I will need plenty of it during this new phase of life.

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Sat Jun 08, 2024 12:51 pm

isinlarsa wrote:
Sat Jun 08, 2024 12:32 pm
Any plans for her also to get together in July with the guy she gave the blow job to? It would be so hot for you to be off with the kids whlle she entertains each man in her extra room.
I'm not sure about the first guy. I haven't written much about the aftermath of that experience, but in short he has had a pretty serious crush on my wife for many years. He reminded her that they had sex twice (several years apart), not the once she remembered and has always thought of her as the one who got away even thought yhey never dated. We are both concerned that it could get messy as he is married.

I wrote earlier that my wife was considered to be a real catch when she was younger and the two meetings she had this week really proved that to be true. In addition to what I wrote above, Sam confided that he was very interested in pursuing a relationship with her when they were younger and that she hurt him by being dismissive and dating many different men. She had no idea and told me yesterday that if Sam had made it known to her at the time she would have pursued a relationship with him.

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Sun Jun 09, 2024 6:05 am

Meeting with Sam on Friday went from:

1. First conversation within 1 hour of meeting:
a. Nothing happened. In open relationship but needs to discuss having sex ahead of time.
b. With light questioning she admitted to kissing him goodbye, with tongue and with a little more prodding rubbing each other and stroking his cock through his clothes. As this was as they said goodbye I assumed they were standing.

2. Second conversation which happened last night about 30 hours after meeting:
a. There was a lot of grinding kissing and groping while on the couch. (I plan to ask some questions about this. Who initiated the kissing? Who was on top grinding? How long did it go on for? Who stopped it?) Do you guys have any I should add to my list? I just feel that there may be more to what happened.
b. I asked if it would have been difficult to stop to get the condoms if not for Sam's agreement with his SO. She responded that there was almost no chance that they would have used a condom. This was shocking to me as we agreed that for oral she would not use a condom but for intercourse she would. I had even purchased condoms for her to use earlier this week. She said that since they are familiar with each other and had not used condoms years ago that she did not think they would now. She said that she was so turned on she just does not think she would have thought to use them.
c. It does not look like my wife will meet Sam again as he and his SO have b-day celebrations all weekend. We will be in NYC for a family vacation in July so I think they will have sex then. As mentioned in an earlier post we will get an additional room at the hotel for her to entertain. I asked if she expects to use condoms with Sam now that she has thought about it and she said no. Another shock for me as it seems what I thought is a "rule" is not. She says she would certainly not go bare with someone new but with someone she trusts she would. She knows I want to lick her pussy after she fucks someone else but that I do not want to do cleanup. If she had fucked Sam this trip I would not have worried about it because it would be at least a day or two between her being with Sam and being with me. But for our trip to NYC we both expect me to lick her pussy soon after he leaves. And as long as she is not too sore to fuck her as well!! She didn't seem too concerned about the short time between his cock being in her pussy and me licking her pussy.
d. I also asked how long she would like to spend with Sam and she said it would be best if she left when the kids fall asleep and return before they wake up. So at least 5 or 6 hours.
e. She masturbated on Saturday afternoon fantasizing about Sam taking her from behind. She said that she has never fantasized about a specific person while masturbating. She generally just thinks about a big dick and watches porn.

isinlarsa
OHW Addict
Posts: 2220
Joined: Thu Mar 31, 2016 5:44 am

Re: Wife's First Time? Hopefully.

Unread post by isinlarsa » Sun Jun 09, 2024 6:57 am

Kind of a letdown that only a little happened. I hope things work out in July.

In the first conversation do you mean Sam had to clear it with his SO before having sex with your wife? Too bad he didn't already clear it. I wonder why he didn't.

She admitted stroking his cock; but did she say how much Sam felt up her body? Was she trying to get him to change his mind about fucking?

Yes, in the second meeting it would be exciting to know who initiated the kissing and who was on top in the grinding. Given how the first meeting went, I wouldn't be surprised if your wife was the aggressor. What do you think?

Your wife certainly doesn't want to use condoms -- at least not with Sam. How much does that worry you, and how much does it excite you? To the best of my knowledge my wife always used condoms when she was dating while married. However, I did fantasize that in the throes of passion she would want him to fuck her bareback.

It sounds like she may want you to lick her while she's still full of Sam's cum. Are you ready to do that if that is what she desires?

From her fantasizing about Sam taking her from behind, I would say that she's really ready for another man to fuck her. It would be a disappointment to both her and you if Sam doesn't come through.

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Sun Jun 09, 2024 7:34 am

isinlarsa wrote:
Sun Jun 09, 2024 6:57 am
Kind of a letdown that only a little happened. I hope things work out in July.

In the first conversation do you mean Sam had to clear it with his SO before having sex with your wife? Too bad he didn't already clear it. I wonder why he didn't.

She admitted stroking his cock; but did she say how much Sam felt up her body? Was she trying to get him to change his mind about fucking?

Yes, in the second meeting it would be exciting to know who initiated the kissing and who was on top in the grinding. Given how the first meeting went, I wouldn't be surprised if your wife was the aggressor. What do you think?

Your wife certainly doesn't want to use condoms -- at least not with Sam. How much does that worry you, and how much does it excite you? To the best of my knowledge my wife always used condoms when she was dating while married. However, I did fantasize that in the throes of passion she would want him to fuck her bareback.

It sounds like she may want you to lick her while she's still full of Sam's cum. Are you ready to do that if that is what she desires?

From her fantasizing about Sam taking her from behind, I would say that she's really ready for another man to fuck her. It would be a disappointment to both her and you if Sam doesn't come through.
I must not have been clear. Sam and my wife only met once and the two conversations were ones I had with my wife about their single meetup. The conversations were one day apart and the details were very different so I can see why you thought it was two separate meetups as her descriptions were so different. Sam did not ask permission from his SO because he had no idea of my wife's intentions. And my wife did not know he was in an open relationship. When my wife made her intentions clear he was shocked because he never believed he would have another opportunity with her since she had married me.

isinlarsa
OHW Addict
Posts: 2220
Joined: Thu Mar 31, 2016 5:44 am

Re: Wife's First Time? Hopefully.

Unread post by isinlarsa » Sun Jun 09, 2024 7:39 am

Thank you for the clarification. It is more clear to me what occurred. It does sound like she would have been ready to have sex with Sam, except for his need to check with his SO. Is that correct? Did you have that understanding as well, so you were thinking she would be returning to you having been fucked by another man?

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Sun Jun 09, 2024 8:26 am

She was definitely ready to have sex with Sam. Both on Friday when they met and on Saturday if he had been available. Before she left I was not sure that anything would happen on this trip, but I was certainly hopeful. For full sex it seems like the stars just weren't aligned as Sam had plans with his SO that could not be broken. But she did give a bj to the guy on Thursday and if that hadn't become strangely emotional after he came down her throat, she would have had sex with him once he recovered and was hard again.
I must admit that I am happy with the progress and would truly be surprised if my wife does not sleep with Sam in July and would be shocked if she does not have sex with someone this year. For me that is a great result as I know some men wait 5-10 years to get to this point. For me it's really only been a year of fantasizing with her about becoming a hotwife.
In regards to Sam, the only thing that would make my wife apply the brakes is if he wants to have a relationship beyond what she wants, which is a FWB. That is what happened with BJ guy on Thursday and she does not want a repeat of that so she will talk with Sam between now and July to make sure their goals are aligned.

isinlarsa
OHW Addict
Posts: 2220
Joined: Thu Mar 31, 2016 5:44 am

Re: Wife's First Time? Hopefully.

Unread post by isinlarsa » Sun Jun 09, 2024 9:08 am

Your wife's attitude toward extramarital sex is just what I would want in my wife. No deep emotional attachment; but just fun sex with someone other than husband. My wife started that way. Funny story. After she had been with a couple of different guys we were talking and I referred to them as her boyfriends or lovers. She crossly said to me: "Don't call them my boyfriends or lovers." Without thinking through my response, I retorted: "Well, I thought that was better than calling them your fuckers." If looks could kill I would be dead.

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Sun Jun 09, 2024 1:23 pm

My wife is heading to the airport and is no longer with her girlfriends so she told me a little more about the blowjob she gave on Thursday. As mentioned earlier I rarely get blowjobs and never to completion. She just told me the biggest surprise of the trip was how much she loved sucking him, how good it made her feel and how much she has been thinking about it since. I asked why and she said he was shorter and thinner than me so she was able to take him fully in her mouth and throat without feeling like she was choking and her mouth was stretched open. She said when he came he was down her throat and she loved it. She also said that she could suck a cock like that for hours and might even randomly drop to her knees without any thought of reciprocation. Really amazing!!!
She did say that for intercourse he was probably lacking a bit but who knows. She said sucking him made her so wet that maybe she would cum really easily.

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Mon Jun 10, 2024 5:22 pm

isinlarsa: I didn’t answer several of your questions so here goes:

Your wife certainly doesn't want to use condoms -- at least not with Sam. How much does that worry you, and how much does it excite you?
Of course I’m worried about STDs, but I am wildly aroused by the idea that my wife can’t help herself.

It sounds like she may want you to lick her while she's still full of Sam's cum. Are you ready to do that if that is what she desires?
I assume he would not finish inside my wife. As I wrote earlier, I think I could be convinced to do a lot of things if I was hard, and in the room while my wife is fucking another man. But if she returns to our room with a creampie I almost certainly would not eat it.

From her fantasizing about Sam taking her from behind, I would say that she's really ready for another man to fuck her. It would be a disappointment to both her and you if Sam doesn't come through.
Totally agree. She said she masturbated again this morning while thinking about him.

patw3268
Experienced
Posts: 106
Joined: Mon Feb 26, 2024 3:43 pm

Re: Wife's First Time? Hopefully.

Unread post by patw3268 » Mon Jun 10, 2024 5:59 pm

Im really happy for you. If my wife would ever take another man’s load down her throat I. Would. Die. Congrats and look forward to reading more.

isinlarsa
OHW Addict
Posts: 2220
Joined: Thu Mar 31, 2016 5:44 am

Re: Wife's First Time? Hopefully.

Unread post by isinlarsa » Tue Jun 11, 2024 6:51 am

justlookin2day wrote:
Mon Jun 10, 2024 5:22 pm
isinlarsa: I didn’t answer several of your questions so here goes:

Your wife certainly doesn't want to use condoms -- at least not with Sam. How much does that worry you, and how much does it excite you?
Of course I’m worried about STDs, but I am wildly aroused by the idea that my wife can’t help herself.

It sounds like she may want you to lick her while she's still full of Sam's cum. Are you ready to do that if that is what she desires?
I assume he would not finish inside my wife. As I wrote earlier, I think I could be convinced to do a lot of things if I was hard, and in the room while my wife is fucking another man. But if she returns to our room with a creampie I almost certainly would not eat it.

From her fantasizing about Sam taking her from behind, I would say that she's really ready for another man to fuck her. It would be a disappointment to both her and you if Sam doesn't come through.
Totally agree. She said she masturbated again this morning while thinking about him.
Yes, I agree it is wildly exciting for your wife to get so aroused that she begs the man to take her bareback and to fill her with his cum.

If you are anything like me, if I'm hard and just watched her fucked, I could be convinced to go down on her if she asked me to. My introduction was her making me eat her out without telling me she had just been fucked bareback.

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Thu Jun 20, 2024 8:47 am

A minor but important update.
1. I booked two rooms for our trip to NYC in July. One for the family and one for my wife to use as a playroom.
2. She has been texting with the two guys she kissed/blew when she was in NYC earlier this month. Her preferred partner is almost certain to be available when we are there.
So if all goes to plan my wife will be fucking another man within the next 3 weeks.

User avatar
Fearlesspain
Experienced
Posts: 186
Joined: Tue Apr 09, 2024 8:44 pm

Re: Wife's First Time? Hopefully.

Unread post by Fearlesspain » Thu Jun 20, 2024 6:29 pm

Im sorry that last time didnt work out but the fact that the room is booked and she is already fantasizing how shes going to take his cock is amazing! Dare I say that the anticipation may even be making it more exciting.

Please fill us in on any texts between them in the meantime.

July cant get here soon enough! I'm gonna try and take my wife to a nude beach for the first time. Here's to grand July for the both of us!

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Sun Jul 07, 2024 11:55 am

Tomorrow we head to NYC and I expect by the end of the week I will have been fully cuckolded. My wife has setup a date for Tuesday with Samuel. While they have not explicitly said they will be having sex we both expect it to happen. In addition my wife is open to an encounter to someone she meets in a bar or other public place. In the last few weeks she told me about several men in NYC who were very forward with her so I don't think this is out of the question.
I last had sex with my wife on Thursday and have been told I will not be allowed PIV until after her date with Samuel as she wants to be tight and horny. She says she also wants me to be excited so I will not be allowed to masturbate today or Monday.
I will update this thread as we get closer to Tuesday's date and will of course update about her time with Samuel.

bowlerlb
Trainable
Posts: 80
Joined: Sun Apr 26, 2020 6:44 pm

Re: Wife's First Time? Hopefully.

Unread post by bowlerlb » Sun Jul 07, 2024 1:33 pm

justlookin2day wrote:
Fri Jun 07, 2024 2:25 pm
myoralannie wrote:
Fri Jun 07, 2024 1:49 pm
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.
Totally agree. It is not appropriate for you to cum while your wife and her Bull are fucking. They should not be distracted in any way and you should be at the peak of your arousal when they have finished and ready to clean up any fluids off his cock and then thoroughly clean your wifes dripping used pussy. That is why you are there. They dont need you for anything else.

toshare
Player
Posts: 306
Joined: Wed Oct 31, 2018 9:29 am

Re: Wife's First Time? Hopefully.

Unread post by toshare » Sun Jul 07, 2024 2:48 pm

As a cuckold, I agree with Bowlerlb. Ive been there to clean up my wife and her lover(s) many times. I too was so against that idea, but once my wife got me into it..omg its soooo hot and its the role for cucks, for sure!

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Sun Jul 07, 2024 2:50 pm

bowlerlb wrote:
Sun Jul 07, 2024 1:33 pm
justlookin2day wrote:
Fri Jun 07, 2024 2:25 pm
myoralannie wrote:
Fri Jun 07, 2024 1:49 pm
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.
Totally agree. It is not appropriate for you to cum while your wife and her Bull are fucking. They should not be distracted in any way and you should be at the peak of your arousal when they have finished and ready to clean up any fluids off his cock and then thoroughly clean your wifes dripping used pussy. That is why you are there. They dont need you for anything else.
bowlerlb : I will not be in the hotel room while the are together, so there will not be any cleanup. As you say she certainly does not need or want me to interrupt them or play any part. I'm looking forward to a recap and sloppy seconds.

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Sun Jul 07, 2024 4:17 pm

toshare wrote:
Sun Jul 07, 2024 2:48 pm
As a cuckold, I agree with Bowlerlb. Ive been there to clean up my wife and her lover(s) many times. I too was so against that idea, but once my wife got me into it..omg its soooo hot and its the role for cucks, for sure!
I must admit that I am nervous about the slippery slope.
5 years ago I would have said it was insane to share my wife. Now it is my biggest turn on.
1 year ago I would have said it was unthinkable to lick my wife's pussy clean. I'm still not ready but certainly see it as inevitable if my wife requests it.
Now, I would say it is incomprehensible for me to clean her lover's cock... but who knows in the future.
Receiving anal is a hard no, but as my list above clearly shows, one never can predict the future.

elina
OHW Addict
Posts: 1997
Joined: Sun Mar 05, 2023 1:29 am

Re: Wife's First Time? Hopefully.

Unread post by elina » Sun Jul 07, 2024 11:19 pm

justlookin2day wrote:
Sun Jul 07, 2024 4:17 pm
toshare wrote:
Sun Jul 07, 2024 2:48 pm
As a cuckold, I agree with Bowlerlb. Ive been there to clean up my wife and her lover(s) many times. I too was so against that idea, but once my wife got me into it..omg its soooo hot and its the role for cucks, for sure!
I must admit that I am nervous about the slippery slope.
5 years ago I would have said it was insane to share my wife. Now it is my biggest turn on.
1 year ago I would have said it was unthinkable to lick my wife's pussy clean. I'm still not ready but certainly see it as inevitable if my wife requests it.
Now, I would say it is incomprehensible for me to clean her lover's cock... but who knows in the future.
Receiving anal is a hard no, but as my list above clearly shows, one never can predict the future.
Dear justlookin2day,

I highlighted 2 sentences in your reply above.

To me, the interesting thing here is how your own (and I think this is true for all of us who are actively seeking to evolve and grow in different aspects of our lives as we mature) desires are evolving here,
And at the same time, Your Wife's desires will be evolving at the same time.

As She is opening up to have a wilder sex-life with other males, you have a stronger and stronger desire to se it happen.
These desires are there and we may become distracted by natural feelings of jealousy and fear of the unknown (we are releasing control to our Wives), but fundamentally the desires to be cuckolded (and increasingly submitting to our Wives) are still there.

I think your insight that we cannot predict the future is fully correct, and maybe that is what makes it exiting and interesting?

I hope you will be able to enjoy this week in New York, maybe try to just focus on how to make sure your Wife enjoys Herself?

Good luck,
Looking forward to hear from you as things progress.

Sincerely
elina
(submissive male)

Shiphead
Player
Posts: 366
Joined: Mon Aug 14, 2023 6:25 pm
Location: SoCal

Re: Wife's First Time? Hopefully.

Unread post by Shiphead » Mon Jul 08, 2024 10:37 pm

Justlook,
Just do what is comfortable for you and her. There is no right or wrong. There is only right and that is what you two decide.
It find it interesting that a few cucks have instructions for others on what they need to do. It is usually the same few.
I read your post and find it really hot. I understood that you didn't want to be there the first time and your wife didn't want you there. You were going to get a second room for them on another floor and you are going take care of the kids.
I love the whole hook up in the bar situation. I would love to sit in the back and watch that happen. I find that's exciting stuff. The hormones are running hot on both sides. It's fun watching the moves the guys are making to try and get in her panties.
I'll have to read your post again to see if you have plans on handling future dates.
Good luck. Be comfortable and have fun.

justlookin2day
Trainable
Posts: 88
Joined: Sat Dec 10, 2022 10:08 pm

Re: Wife's First Time? Hopefully.

Unread post by justlookin2day » Tue Jul 09, 2024 12:25 pm

My wife has just left our hotel room and is walking to meet Samuel. Once they connect, walk and flirt, I expect they will return to our hotel for what we both hope is great sex. I'm resting with our kids in our room, while she will use the other room I booked for her to play in.
A few things to note:
Last night, after the kids went to sleep we went to the second room to see how it looks. I asked for a hand-job which she quickly denied and said the room was not for us but for them.
We are meeting friends for dinner so the first time I see her after I'm officially a cuckold will be when she joins me with our kids and our friends with their kids for dinner. I'm hoping I can appear cool, calm and collected when she joins us for dinner.

venus-can99
OHW Addict
Posts: 3095
Joined: Thu May 25, 2023 11:57 am
Location: Not the 51st State

Re: Wife's First Time? Hopefully.

Unread post by venus-can99 » Tue Jul 09, 2024 1:03 pm

Hope she has fun with Sam...

Post Reply