Potentially the Start

[venus-can99]

Thanks for the update DDW. Looking forward to HW's next moves. Seems like she is really enjoying the HW'ing experience and hopefully this moves to multiple partners over time.

[tovid555]

Well, I have to agree. I think our favorite cuckoldress may be crossing a line in her personal traits as her traditional tendencies seem to be slowly falling by the wayside. But really, is anyone surprised (especially her)? Look at everything she has done in the last six months? I'd be very surprised if she hadn't changed her views from her previous conservative (vanilla) days. A lot has changed and I think there is even more on the horizon.

[txrockdog]

The "You do know I've never been a one-night stand person, keeping more than one person in my life physically?" "I've always been a romantic deep at heart?" is tossed out the window now.

Well of course! Who is she to say no to her BF, right? This is just the next step she has to take down the path her BF is leading her.

[Gearup]

Just when I thought this thread was growing a little old.........The boyfriend saves the day!! Hearing that Mrs. DDW is potentially branching out and dipping her toes into deeper hotwife waters is , well, HOT!

[elina]

Well, I have to agree. I think our favorite cuckoldress may be crossing a line in her personal traits as her traditional tendencies seem to be slowly falling by the wayside. But really, is anyone surprised (especially her)? Look at everything she has done in the last six months? I'd be very surprised if she hadn't changed her views from her previous conservative (vanilla) days. A lot has changed and I think there is even more on the horizon.

We all develop as we go through life.

To me, It is absolutely wonderful to see how DDW is no longer a wannabe, but a complete cuck who has ceeded control to the Wife he still loves who has clearly developed to a Hotwife and then towards a Cuckoldress while Her cuck is mesmerised and, even if he doesn't share much emotion here, through his responses to the questions asked by his Cuckoldress, demonstrates his submission and only wanting His Wonderful Wife to expand Her sexual activities. And DDWHW just loving him more, but differently, for it.

I am very grateful that you continue to share your story.

Sincerely
elina

[Watchinu69]

Just when I thought this thread was growing a little old.........The boyfriend saves the day!! Hearing that Mrs. DDW is potentially branching out and dipping her toes into deeper hotwife waters is , well, HOT!

Well said Gearup! We like when it gets fresh!

[Deepdownwannabe]

And the week started with a bang, as she told me she wanted to go out with me Friday night. Only we were going to roleplay it, I was not her cuck, I was to be a date. I was confused but she said she wanted to do a dry run of a date with a stranger. I was the guinea pig. "Let's just say this is a dry run before I give an answer. You'll see how it will go, I would like you to play along please". And that was that.

It became clearer later in the day when I received an email from her, only it wasn't addressed to me, it was addressed to this fictitious person that I was to be. She introduced herself, as the girlfriend of my friend. She said that she was asked to look after you in town this Friday night while I was "visiting". She said she looked forward to meeting me, and that she had even taken the liberty of making a reservation at a local nice restaurant.

It dawned on me I was to pretend I was this stranger in from out of town, friends of her boyfriend. And I was to take her out Friday night. This is strange.

[MonaLisaOverdrive]

Dude, get into it.

Play the role with everything you've got and fuck her brains out.

[TheHammer]

Damn, she is an absolute gem. Get to working on your character and have some back stories, hobbies, personality, sexual history, etc in order for your alter ego.

[subtoall]

She's got a playful, creative mind. Let he run wild with it and follow wherever she leads. I suspect you'll have a great time playing with this, and whatever else she dreams up and throws at you.

[venus-can99]

That’s wonderful news DDW. I love HW’s creativity and planning - a dry run prior to the actual launch

[elina]

Thank You DDW,

To me this looks like more Fun than strange.
But anyhow, this is what your Superior Wife and Cuckoldress wants to do. If I were in your shoes I would try to be a good cuck, try to make the best act possible and make every effort to ensure that She will enjoy Herself!!!!

Sincerely
elina

[kinkydetroit]

Here is a fun "all in" role play idea. My thought is if she wants you to role play it, go all in and take charge of the evening.

Open a new email addy, write to ddwhw introducing yourself as her BF's friend and explain how excited you are to meet her this Friday for dinner. Explain how you will be staying at xxx hotel and suggest that instead of the restaurant she choose,you could instead meet at the hotel's restaurant for dinner. After all, if he is coming from out of town he would probably be staying at a hotel and if the actual evening were to go as we are all fantasizing why would he want to deal with logistics of restaurant to car to hotel. The icing on the cake, if budget allows, is book a room in the hotel. One can hope that your "all in" role play might be rewarded.

[tovid555]

Play the part well. Remember this isn't about you, it is about her and finding out if she is comfortable with all of this. I think she is but she just wants a personal confirmation of it. Nonetheless, what a great idea of hers!

[BoBatty]

I would be careful about "Topping from the Bottom". Your wife is putting herself out there and being creative. I would let her call the shots. I agree that having an interesting backstory and personality is a great addition, but I personally would not want to alter her dinner plans or try to control the flow in any way.

If you make changes she may believe that you are not on board with her plans and she may lose interest.

She cares enough to do this for you I say see how it goes.

[Deepdownwannabe]

She has continued this game as it seems we are having two different conversations. Some parts I am the husband cuck while other parts I am the visiting date. I think I even detected that she was flirting with the date in some of the correspondence. I still had no idea what the end game was going to be.

[kinkydetroit]

I went back and reread your original post about Friday. From what you wrote I understand that you are to role play the visiting friend. It would seem that her sending you emails that are like CC's of her emails to him she is providing insight into her expectations of her future meet w actual friend. I perceive that ddwhw is offering you the opportunity to describe your fantasy about what might happen in her meet up with the "friend". To me this is a way for you to tell her what you find hot about the scene as a third person. Kind of reminds me of the way a husband might want to tell the wife about some kinky scene that he would like to play out. Rather than just say it he relates a dream he had or a story he read. Kind of provides an excuse if she does not like it. Oh it was a dream or something I read about I would never suggest we would do something like the story I related.
Turn the planned role play date into a scene that you would really get off on her agreeing to. Have fun!!!

[venus-can99]

I hope you are having fun DDW - love the way HW is developing this game and giving you a role

[scarlettscuck]

Deepdown… go with this role play. It’s incredible and you are so lucky! She’s a gamer as a Hotwife. You need to find a frame of mind where you can actually “be” the new suitor Friday. Shed any inhibitions you might have and step up, be HER dream man Friday. It will be YOU except for the role play. Have fun with it, give her the dream date that you would if you could go back 7 month. Go buy a new shirt, a sport coat and some new cologne and show up that night with confidence and play along. Turn the page and blow her mind! Your Friday night sounds like the hottest night ever! You can do this!!!

[_xavier_]

It seems to me that she's not auditioning you as an alter ego, she's practicing her expected role when her bf "pimps her out" to his friends or business prospects.

You definitely need to play the part of a less submissive man, the sort of self assured man who would feel fully entitled to a hot slut being sent to take care of his needs like an unpaid high class call girl. Put on your power suit and invent a small backstory about the deal you're in town to close, or which one of your businesses you're in town to check in on / acquire. Use your deeper voice, talk slower and with more confidence. Flirt, but in the way a man would who has zero doubt he'll be undressing his companion as soon as he decides dinner is over. Channel your version of Don Draper.

Just... don't necessarily expect you're going to get unlocked to enjoy the happy ending that fictional man will. But not to worry, once she practices her invitations, dropping sexy hints into the conversation, leaning forward to tease you with the occasional glimpse down her blouse and finds how it is to put herself on the menu for this 'stranger' just to please her king, she'll let you know how this is all preparation for a promise she made him about servicing an acquaintance of his next week or the week after, and you'll get to hear all the details of those acts she isn't going to perform on a silly little cuck.

[Deepdownwannabe]

Last night she told me she would not be at the house after work today and that she would meet "her date" at the restaurant. I was reminded I was not to be "me" this evening and she gave me a very enthusiastic hug and I love you'd before we split off for the day.

[frb]

Have a great night DDW, role playing as the object of your wife's lust. These opportunities are about as frequent as solar eclipses or earthquakes in NYC.

[SusAno]

I hope you make the most of this Ddwb. Having a friend arrange a date for you with hot wife is a wonderful gift.

I would want to know more about her. Who is she and what does she do? How did she meet your friend and what’s their relationship? And what about her husband? You will be absolutely floored by her classic beauty so how can he let her out of his sight? When you hear about how bad at sex he is and how much more excited he is by being kept horny for her, some of the picture will make sense. You may even have met cuckolds and be able to talk about what seems to excite them.

With a lot of compliments and learning more about this gorgeous sexy adventuress, you may might be flirting more openly as the evening goes on. The occasional touch and open gaze may have got things more exciting. That maybe the time to find out more about what she is wanting out of this experience. What have been some of the most sexy and exciting things she has tried? What does she like? What does she want to try next?

If you do your job well she will be much more comfortable and confident as she meets her next potential lover. If you do it really well your flirting will have made you both horny. Maybe things went well enough to have a hot kiss or spent time making out.

How she rewards or punishes (or both) will be revealed at the end of the evening. Will you do such a good job that get to see her naked, perhaps with her boyfriend. Or will she build a passionate connection with you, then have you drop her off at her boyfriends? Or will she take matters into her own hand only letting you hear her as you imagine how much of what she said and did tonight will play out in real life.

Hope you have fun

[tovid555]

Well, this has the makings of a famously devilish weekend. I can't wait to hear how her "date" went. She's good, very good.

[cuckoldtipp]

DDW this sounds like your life is going to get very interesting .and it sounds like your HW is in for a very Hot weekend. Love your updates. Can't wait for more