progress story

[Breaker445]

Breaker, you need to follow-up when she gives you an opening.
"Of course guys fantasize about other women, honey, just like women fantasize about men, that's just human nature."

Ahhh that is a good one! I either don't realize there is an opening when there is one, or if I do I don't know what to say.

So I had planned on sending her a text about the challenge that ddriver had suggested. Since I didn't know when the next time she would tease me that I couldn't last I figured I would star the challenge a bit different. But before I had a chance to send the message I got a text from her in a super skin tight white dress with the question, "When are you going to take me out so I can wear this?" She looked stunning and I responded hopefully soon! I asked her if there was something she really wanted and she responded, "Hahahaha oh yes always " she followed that up with the question, "Why?" I told her there was this naughty game/challenge we could play and explained to her that I would have one hour to last with her and if I make it I win and get something I want but if I don't last the hour she got something she wanted.

She responded, "Hahaha oh wow....I would so win." I told her we should set a date night, and then do the challenge after our date. She texted back, "Ok!"
I asked her what she would want and she texted probably shoes. If that is the case, it should be easy to top that item for round 2.

Anyways, I got home and no surprise the vibrator was moved. I am thinking our date and challenge will be this upcoming weekend, I am excited to see for one, what she plans to wear out on our date, and two, the things she is going to do and say.

[ddriver86]

Hey Breaker445,

Sounds like you have it going on. I envy you!

When you set up for "Round Two" you need to be extremely confident that "Round One" was a FLUKE and you have the stamina and manliness to win the bet. Keep using the phrase "I am MAN enough to please you for at least an hour." She has to believe you and be challenged again to prove to you that she can win.

Also, remember for "Round Two" when she tells you what she wants, remember to be so confident that you will add some sexy play to it. Stuff you do not want to do, even if you secretly do, like be in chastity for 1 month, be on house choirs duty for a month, unlimited massages for her from you, have to eat your own ejaculate every time you climax for the next month, you have to stay home and she can go out with her girlfriends as much as she likes for the next month, she gets to take you with a strap-on, etc. Don't scare her or gross her out though. Just whatever she will find intriquingly sexyish. It's because you know without a doubt you will win. Right?

Good Luck and please keep us informed.

[BallSpanking]

Maybe you can offer the next prize, maybe a challenge that she would be turned on by...

[Breaker445]

Hey Breaker445,

Sounds like you have it going on. I envy you!

When you set up for "Round Two" you need to be extremely confident that "Round One" was a FLUKE and you have the stamina and manliness to win the bet. Keep using the phrase "I am MAN enough to please you for at least an hour." She has to believe you and be challenged again to prove to you that she can win.

Also, remember for "Round Two" when she tells you what she wants, remember to be so confident that you will add some sexy play to it. Stuff you do not want to do, even if you secretly do, like be in chastity for 1 month, be on house choirs duty for a month, unlimited massages for her from you, have to eat your own ejaculate every time you climax for the next month, you have to stay home and she can go out with her girlfriends as much as she likes for the next month, she gets to take you with a strap-on, etc. Don't scare her or gross her out though. Just whatever she will find intriquingly sexyish. It's because you know without a doubt you will win. Right?

Good Luck and please keep us informed.

Thanks, those are good ideas.

Just today she told me in a cute little sad tone that she wanted to hang out and be social. I told her I did too and that we needed to come up with something. I don't know exactly what she means, because it was so close to us talking about going out if she means go out with a group of friends, or her and I go out to a dance club or something. I'll try to bring it up again and see if she will elaborate more on what she wanted. It was said in quick passing so we didn't get to talk much.

[BallSpanking]

Ask her, but suggest the latter, where she can cut loose a little bit, and flirt with sexy guys?
I doubt she would do that in front of your whole social group.

[Breaker445]

Ask her, but suggest the latter, where she can cut loose a little bit, and flirt with sexy guys?
I doubt she would do that in front of your whole social group.

You'd think so, but to my surprise the last time we went out with friends it ended up being a group setting and she got hit on by a guy which I could tell she enjoyed. I had to step in to get the guy to move along. I still have her facial expressions in my mind from when she was talking with the guy, I could tell she enjoyed the attention.

[BallSpanking]

Possibly you are right, but my guess is she would be less inhibited in a crowd where she is not known, and it wouldn't get back to her in "polite" society.

[BallSpanking]

"When are you going to take me out so I can wear this?"

You can tease her by telling her she doesn't need to go out to wear that dress.
She can wear it for you at home.

If she reacts with disappointment, you will know she intends to wear it for the benefit of other men.

[Serrand]

Well, I don't know, but maybe you should show a little caution about the "challenge" the commentator above suggests.

In general, I think, if your wife would ever starting cuckholding you for real, because she's disappointed of you in the "sex department", it would leave you in a very dangerous position, in my opinion. There would be the very possible imminent danger, that your wife would start loosing respect for you.
So to speak, if you ever should introducing your wife into cuckolding, you should do it from a position of strength and not of weakness. Therefore, I believe it's very important for you to try everything to be a sufficient, satisfying and good lover for your wife.
As some maybe here suggest, for you starting deliberatetly "to disappoint" her with your bedroom performance, that would be a extremely stupid and dangerous idea.
But like I said, that's only my humble opinion. Take care

[BallSpanking]

Serrand is correct.
There is a danger from indulging in humiliation. Disappointment in your sexual performance and in you as a man, can be destructive to her regard for you. It is better if this becomes a joint project for her to be more fully sexually satisfied.

[bobbiecd]

Serrand is correct.
There is a danger from indulging in humiliation. Disappointment in your sexual performance and in you as a man, can be destructive to her regard for you. It is better if this becomes a joint project for her to be more fully sexually satisfied.

^^^this^^^ I'm of the opinion that sometimes -- most times? -- women will use fantasies as a way to draw you in closer. They simply want to be #1 to you, especially in a sexual way. If however, fantasies are needed for the cuck to find the wife/SO attractive, eventually the wife/SO figures it out and that's when things can go sideways. She'll either want the fantasies/stories to stop because she wants you to appreciate her without the fantasies (and wants you to be the bull), or she may go the distance to "punish" you in the hope you come around to her, or ... she can ascertain whether the fantasy means more to you than her, in which case she'll bail. I'm not saying things can't work, just that cuckolding presents a very complex, slippery slope. It's one helluva sexual mind fuck and it's why I think older, more seasoned and settled relationship partners, have a better chance of making it work. Not to mention that it can fuck your mind up too and your subsequent relationships will bear witness to that.

Disclaimer: Not all of what I write is based solely on observation...

[ddriver86]

Hey Breaker445,

Some have raised caution about the challenge technique. And their points are valid. After reading your story you and your wife are already into humiliation play. You and her are already going down this path. From what I have read you both are getting off on it greatly and what to explore it more. If I am wrong let me know. It will not be something new to you or her. She already knows she can win. As I said before, the challenge will move you along faster and answer a lot of guessing on your part that could take weeks and months to figure out.

If you don't feel comfortable after the first round, slow down and reconsider the second round. You still can do round two anytime. You don't have to do it the next weekend or even the next month. The challenge is going to tell her what she already knows and the cool thing is it will tell you what she is thinking by what she does to win. That's it.

I am not sure I would be that concerned about her having a negative revelation about you because of a sex game. It's your decision though, but it already seems she wants those shoes. Or you can always win and get what you want. What was that by the way?

Just let us know how it goes whatever you do. I appreciate you sharing with us.

Good Luck!!

[Breaker445]

Hey Breaker445,

Some have raised caution about the challenge technique. And their points are valid. After reading your story you and your wife are already into humiliation play. You and her are already going down this path. From what I have read you both are getting off on it greatly and what to explore it more. If I am wrong let me know. It will not be something new to you or her. She already knows she can win. As I said before, the challenge will move you along faster and answer a lot of guessing on your part that could take weeks and months to figure out.

If you don't feel comfortable after the first round, slow down and reconsider the second round. You still can do round two anytime. You don't have to do it the next weekend or even the next month. The challenge is going to tell her what she already knows and the cool thing is it will tell you what she is thinking by what she does to win. That's it.

I am not sure I would be that concerned about her having a negative revelation about you because of a sex game. It's your decision though, but it already seems she wants those shoes. Or you can always win and get what you want. What was that by the way?

Just let us know how it goes whatever you do. I appreciate you sharing with us.

Good Luck!!

You are correct she and I have been doing humiliation play for years now and she has known for years that humiliation play turns me on and I enjoy it and it has seemed to never affect our relationship. I do appreciate the others posting their thoughts and opinions and they are right about many of the things, but as far as this challenge and the sex games we play I have no worries. I see this challenge turning out to be a fun little game where we both enjoy. She already seems to be looking forward to it.

By looking forward to it she sent me two photos of her in the outfit she is thinking about wearing for our date. Her body language in the photos is that of confidence and taunting. I responded to her, "Whoa!! You're hot!" She texted back, "I like it." I texted back to her that if we do the challenge on our date I may not even last leaving. She responded, "Hahahahaha." The outfit she had on was a tank top, tight jeans and ankle boots with her toes peaking out, along with a laced choker.

I am wondering a few things about the challenge. Since it will be played out after our date night, I wonder if she decides to start early and says or does things while out on our date that can give her an advantage (Such as bringing up on her own she notices an attractive guy), and then when the challenge begins how quickly does she go into cuckolding talk, and what type of things will she say about cuckolding. I may sneak the use of the numbing spray before hand just to give me a better chance of lasting a few more minutes.

I noticed she used her vibrator again. I am anxiously awaiting her dildo to arrive and see if she enjoys it and if she ends up using it as much as her vibrator. I can't believe how often she uses it, it is almost a nightly thing if we don't have sex. Today her outfit was one I have not seen before, it was a casual dress but it was a short dress! Super hot and she let me know she got looks when she was out.

[BallSpanking]

Nice.
It sounds like she also enjoys the male attention, so it should be an easy and small step for her to flirt with them. If you give her room, spend a long time at the bar, or in the bathroom, there will be guys hitting on her, offering to buy her drinks, or asking her out to dance. Your delayed return would give you the opportunity to scope out what she is doing, quite approvingly.

[Breaker445]

Unfortunately we never got around to having our challenge. Things just happened and I came down with the flu. Although I wasn't feeling the best we still were able to have a little date out, but feeling under the weather nothing really happened at all. She did switch up her outfit for our date to a little more "darker" look. She wore a black tank top, black tight jeans with holes in them and black leather sandals that had these sexy black leather straps that went up her ankle. When I commented on how hot she looked she said she knew I would like it.

Probably the best tease she gave me was after our date when we got home she got into lounging clothes but wore her hair the way that always gets me turned on. Feeling under the weather I still wanted her badly and she knew it. I told her how hot she looked with her hair the way she had it and she gave me a laugh and said she knew I would like it and that was why she wore it. But I think she wore it more for a tease because she knew I wasn't feeling great. However I was able to muster up the ability to have sex. I hadn't relieved myself in days so I struggled to not end so early. She seemed to enjoy my struggles because I would give her a few thrusts then have to pull out as to keep myself from cumming. Each time I would pull out she would give me the "Mmmhmmm, you want me?" Sometimes adding a sweet little chuckle as to taunt my inabilities to stay in her. Along with that i'd get the occasional naughty talk from her telling me I was lucky.

Last night I was starting to feel better but our sex was very vanilla. I avoided cuckold talk to give it a break a couple times. Now basically two times having sex without me bringing up any sort of fantasy or kink doesn't make it seem like everytime we do it it involves a fetish.

However, there were a few subtle things I caught on to her saying that I found intriguing over the weekend. One was when we were driving from our date we got talking about how we will have to go on another date soon. I brought up, you still haven't worn your mini leather skirt in awhile, hinting id love to see her wear that out on our next date. Her reply was she would love to wear it and then added, "We need to go out of town so I can wear all sorts of hot sexy outfits." I showed agreement and she followed up with, "Wear even a gold latex bikini". I showed her excitement and agreed that it would be fun.

So the following night she brought up again getting out of town and basically started planning the whole thing. She mentioned she wanted to be near good nightlife. She found a hotel with a dance club in it and we started talking about it and she got excited about the fact it had a club and a poolside bar. She also brought up that the hotel is a huge party place. I instantly started to remember her conversation the night before about getting away and wearing sexy clothes, then thinking about being in an atmosphere where it definitely will present endless opportunities for something to happen. Along with her driving for all this to happen, I found it very exciting. It makes me think she has something in her mind. The fact she brought up sexy outfits and gold latex bikini, and getting away the night before, then the next night gets on a conversation about getting away, finding a hotel with a poolside bar, and a dance club in it makes me think the conversation the night before about sexy outfits and bikini's was on purpose. Add in there that she in the past she was never a partier, yet made it clear she wanted to be near nightlife and was excited to find a hotel with a poolside bar and nightclub in it makes this whole thing exciting. I mean, a year ago, even 6 months ago she would have preferred to get out of town by ourselves in a nice little relaxing secluded get away where the focus was just on her and I alone. Now wanting nightlife, drinking, dance clubs, and a hotel known for partying, is a big change in her preference.

It also makes me think or at least hope there will be some sort of progress made with this lifestyle when we go. Maybe even some hope that she is the one that tries to plant the seed and water it in my mind that something may happen and prepare me. The reason I think this is because the two conversations we had on two separate days and how they were almost purposefully set up by her along with other little comments ive noticed from time to time.

[BallSpanking]

Hi Breaker,

Are you going to Vegas?
Either way, this is a great opportunity to get her to flirt openly with potential Alpha guys.
It would also give you an excuse to buy her sexy micro or mini skirts, and Wicked Weasel type bikinis.
Vegas has some topless adult pools too, where women can free their breasts from annoying straps...

Perhaps you could prevail on her, that your greatest enjoyment, is in seeing her sexiness to other men, and how you would enjoy observing her hang out and flirt freely.

Have a rescue word set up so you can extract her from any nuisance, but make it clear that you will NOT intervene unless she texts you the rescue word, and that she need not worry about how far she wants to take it if she finds a sexy guy, because you fully approve of her having fun. FULLY APPROVE!

[guster12345]

This story is great. Minus the toys, it reminds me of an old relationship I was in. Good luck

[Breaker445]

Not much to update and I haven't really pushed the fantasy in awhile, just to give it a break and not overdue it. Her toy should be arriving any day now and when she talks about it she does have this excitement about her. She seems to be anxiously waiting for it to come, I just hope that she is in the mood for it when it does finally arrive. I've noticed her vibrator is still getting good use. It is almost a nightly thing routine for her.

Tonight she went out with her girlfriends. I had heard many days ago she was thinking of going out with them, but thought plans had fallen through as she didn't talk about it or bring it up again. So today when I got home I noticed she was all dressed up, looking amazing. She had her hair straight, make up was looking good and she had mascara heavily applied which was sexy. She was wearing super tight white jeans which really showed her legs and butt and was wearing brown leather ankle boots. I got very excited seeing here and asked her what she was doing and she told me she was going out with her girlfriends. I played it off as I had forgotten because I didn't think it was still on. I expressed to her how hot she looked and how badly I wanted her. She laughed and said, "You don't get to have sex with me." I teasingly played off being disappointed and she chuckled at me being declined. When I went to give her a kiss she made sure it was a very light kiss as to not mess up her makeup.

There is no doubt in my mind she is going to get plenty of looks tonight. Her jeans alone with how tight they were and how well they showed off her legs and butt, oh my. I am thinking of sending her a text asking her to let me know if she catches anyone checking her out and see if she plays along or not. The place they are going is more aimed toward males too, it is like a bar/pub and is a trendy type place very popular amongst guys.

One thing I did find a little interesting is lately I've noticed while we lounge around she is intensely attached to her phone screen and ive noticed little smirks and smiles from time to time as she is look at her phone. (if she finds something funny she will usually tell me about it for me to see it too, but she doesn't with these smirks and smiles.) Well the other day I was texting one of my good friends for a good portion of 30 minutes and she asked me, almost in an accusing way who I was talking with. I told her who and she just went about her way. But it made me think, we all read the articles or stories that someone who is cheating sometimes thinks the other one is as well. Now, like I have said before, I am sure she isn't, but connecting the dots of her lately attached to her phone and the occasional smirks and smiles then her asking me with an almost accusing tone about who I was talking with just made me ponder. Like I've said before, it may be hotter to find out something. But if she were she would be doing a dang good job at hiding it because I purposefully try to find something with hopes of finding something and I never do.

[BallSpanking]

Sounds like she is definitely having outside conversations, but it could be innocent.
It also sounds like she may have set up a profile with AFF, or something, and is getting a lot of hits.

[Breaker445]

Just a little update. Once she got to the place they went to she sent me a text that we should go there together. I told her that it would be fun. I then sent her a text telling her if a guy buys her a drink she should accept to be nice with a wink face. She didn't respond and hours went by before I got a text from her, which was only a text letting me know she was on her way home. It was too late for me by the time she got home that I was asleep. This morning after we both left in a hectic busy morning I sent her a text asking her how last night was as we never talked about it. I then sent a text almost immediately following that one saying "Or is that something to wait on telling me and I set up the bedroom as a dungeon and you tell me about it then..... "

Her response was, "Hahaha wow....." Now some may see that as a negative, or an indifference, I however see it as a positive in a way. In the past when I put the fantasy that much forward she would come back with a no, or something along the lines of no is usually followed up with her response. This for me left it open, there was no "No". She didn't downplay what I said, or immediately try to change course. Her "....." in that context usually mean naughty for her, or pondering naughtiness. So for me, I was pleased with her response.

I didn't respond and just let that text sit. I figure tonight I will try to suggest we do set up the bedroom as a dungeon and do a D/s session like the one she enjoyed so much awhile ago. And if she does want to do that see if she plays along with any story from last nights outing.

[Breaker445]

Her toy arrived today! She doesn't know it is here but it did arrive. I am hoping tonight we get to try it out! I also cant wait to see what she says/does when she sees it.

Last night I got lucky with her and had the privilege of having sex with her. She did tell me I was lucky to fuck her before she orgasmed, but after she was done and trying to bring me to orgasm she again told me I was so lucky to fuck her which I told her I was. I told her she was so hot and she replied to me, "I know I am, so many guys wish they could fuck me." She continued her taunt by telling me, "I could fuck anyone I wanted." I moaned yes she could and asked her if she liked knowing she could fuck anyone. Her reply was a sexy "MMhhhmmmm oh yeah." I didn't last long after that. After my orgasm I was ready to go for round 2 but she laughed it off and said a second time was not happening.

We will see about her dildo and how much she enjoys it and if it gets more use or equal use to her vibrator. I do hope, unlike the vibrator, she will use the dildo while I am present, or tell me about using it. With the vibrator she never tells me or brings it up. However, I guess if she is secretly using the dildo almost nightly like her vibrator and not telling me means she might be fantasizing something in her mind that she doesn't want to share.

[Breaker445]

Ok, I think we may be going somewhere now. Last night was amazing and I think she would agree, and I think she enjoyed it to the point where I think for the first time she may be enjoying this fantasy and seeing the benefits. I am excited to see what happens next or comes of this.

So her toy arrived and I was hoping she would go to the table where I placed it as I was wanting her to bring it up on her own. But she never really went around the table to see it. She was watching one of her shows, a show in which she had been waiting to see for awhile now so she was really interested in it. Realizing she was not going to find the package on her own I told her it had arrived. "It's here?" She asked off guard and surprised. I told her it was and she immediately got up, never pausing her show or even really caring she was missing any part of it and went to the table where the package was. She immediately ripped into the plastic and cardboard to open it up.

It didn't take her long to open it and she came back down and sat on the couch next to me. She was instantly attached to it. She pulled it out of the package and with a slight giggle felt it and told me how real it felt and looked. Her giggle turned into intrigue as she continued to hold it and look at it. She started to tell me what she was seeing and feeling with it. I started to get hard as I watched her hold it, feel it, and rub it with her hands as she continued to look at it and feel it as she is telling me how real it felt. She told me to feel it and she handed it to me. As I was feeling it she continued to tell me that it felt like the real thing. And as I was holding it she reached her hand over to my lap to feel me. She noticed I was hard and she said with a teasing voice, "I don't know why you're so hard this is for me."

Without much more time she pulled down my pants and started to compare her toy to me. Almost as if my penis was just another toy she placed the dildo next to it and nonchalantly compared me with it. The dildo was a few inches longer, but not as thick. She noticed the difference and told me about it and also told me about some similarities and differences as we both sat there looking at each. The way she talked and compared the two it was like she was shopping for an item and trying to decide between two things.

I told her I wanted her and we could play with her new toy. She smiled and told me I was naughty and that, "This is for me. I'm not going to tell you when I use it." I begged her why and that I wanted to know because it was hot. She responded with, "It's my little secret." I was raging hard at this point and she gave me another feel. "Ok" she added suggested we go to the bedroom. As she got up, she grabbed her toy and with sexiness and confidence walked to the bedroom as I followed behind admiring her.

Once we got to the bedroom she placed her toy on the dresser and as she got into bed I brought the toy from the dresser introducing it into the bed. She saw me and with a smirk told me I was naughty. She told me she wanted me and I inserted her with ease as she was already wet. I gave her a few thrusts as she seemed to enjoy it and I exited her and grabbed her toy.

We both smiled as we both knew what was about to happen. I slowly entered the dildo into her and without any hesitation she took it with enjoyment. I helped her with it a few times before moving more toward her head and giving her some kisses and telling her how hot she was. A few moans from her and by looking at her I could see she was somewhere else in her mind. I went toward her legs and sat on my knees to sit back and watch her and enjoy her enjoying the dildo. I rubbed her sexy legs as I could tell she was in fantasy land in her mind. She caught me starring and admiring her and she moved her foot toward my mouth. Without hesitation I took her foot and started smelling and licking it as she went on. To my surprise the moment I started worshipping her foot her moans got louder and it seemed she enjoyed it even more. After enjoying her foot she pulled it away from me and looked at me. She reached her arm out to grab my shoulder and to bring me in closer to her. Once I got close to her I gave her another kiss and she asked if I liked this and I told her "oh yes!" She then told me, "I want you to go down there and lick me while I use it."

Inside I was overly excited, I couldn't believe at how much she was enjoying this. I went down and started licking her as she continued using the toy. It was absolutely one of the hottest things ever. I was licking her and she was fully enjoying the dildo going in and out of her and me licking her at the same time. I could feel how wet she was getting and I was enjoying it so much I couldn't hold myself any longer. I came so much it ended up leaving a huge spot on the sheets. But it didn't matter, even though I came early I stayed hard and continued my job. Her moans got louder and more intense and her body started moving it ways I hadn't seen or felt it move. She moaned several times she was going to cum and with each time she told me I could feel her getting wetter and wetter. Finally she orgasmed and from just my point of view it was a great orgasm for her.

We both laid there for a moment and I told her how amazing that was and that I had came already. She didn't seem surprised at all and said, "You probably like this thing because you can cum whenever you want." She told me how good it was and left me to put the toy away. Since she had not used the suction cup she asked me about where she could place it. I told her she could stick it on the bathroom floor or shower, etc. As if she didn't really care about what my response really was she told me, "I'll do whatever I want with it, it's mine." The tone was a taunting type with her basically telling me she will use the toy how she likes, when she wants. I placed the toy in a spot I thought would be appropriate. She asked me where I put it and almost like she was disappointed in my decision where to place it she said she would forget it was there or wasn't such an easy access for her. She made it sound like I should have placed it in a glass case right by her nightstand.

It was absolutely surreal how much she enjoyed it and how hot it was to watch her enjoy it. It was a great moment and I think she would agree. I think she is most definitely going to use the dildo as much if not more then her vibrator and I think she is going to introduce the dildo more in our play. And during the moment of last night, and afterward I had this thought that it would be any moment after using this toy that she will tell me she wants more of this fantasy. With her seeing how much I enjoyed it and how much she enjoyed it and probably how good it felt for her I think she is more into this fantasy then she ever has.

I am probably forgetting things that were said or happened because so much happened, but all I can say is she really enjoyed the toy.

[BallSpanking]

You need to buy her another dildo, just as long, but thicker, at least as thick or thicker than you.
Don't forget to introduce sexy stories of her flirting with hot guys when you use it, so she unequivocally buys into the idea of seducing and fucking other guys.

BTW, when are you guys going "out of town" to try out her new toys and outfits?

[Breaker445]

You need to buy her another dildo, just as long, but thicker, at least as thick or thicker than you.
Don't forget to introduce sexy stories of her flirting with hot guys when you use it, so she unequivocally buys into the idea of seducing and fucking other guys.

Yeah I was thinking the next thing would be a bigger thicker dildo, but knew her first one shouldn't be super large so she could enjoy it and ease into it. I will also introduce those stories or other guys as we continue to use the toy. Didn't want to overdue it on her very first time. Also, I really wouldn't be surprised if the next time we use it it is her who brings up the mention of another guy while she uses it. The way she enjoyed the dildo and saw how much I enjoyed it I feel she is ready to explore this more and the realness of the dildo definitely helps I think.

Just this morning she was getting ready to go out for the day and she spent a good hour getting ready. We have no plans, but she's put on makeup in a sexy way and wearing ankle boots and tight jeans, all the works even a hot looking necklace and a choker and she is going out on her own. I played around with her telling her how hot she looked. She told me, "We've been having sex a lot lately." I told her that was a good thing because she was so hot. She told me, "You should feel lucky." I told her of course I do. I expressed how hot she looked and she told me back "Well if you took me out on a date I could look even better." I told her I would love to take her out on a date and she just played it off like of course I would.

This is all very exciting and can't wait to see how she incorporates this new found territory of hers moving forward.

[BallSpanking]

This could be an excellent opportunity to begin an MFM conversation, using the dildo as guy #2.
This will habituate her to the thought of her enjoying another man's cock with your full approval.