Words with Friends

[Sissy_Michelle]

Good Morning Ladies,

I may not post very often, but I frequent here a lot to catch up on the posts, and everyone's day do day life. There are a few people that I work with that know I underdress on a regular basis. That I rarely if ever fully dress. My wife's best friend found out that I cross dress a few years ago and we play Words with Friends quite often. She is also someone that I can confide with and gives me inspiration and courage. She is very pretty and we have hung out and gone shopping on many occasions, she had suggested to me last year that we have "Challenges" to our games. Now I know everything I tell her will eventually be heard by my wife. Although with our marriage we have a no secret no "BS" communication policy set up. Though she supports my crossdressing she doesn't want to participate, where her friend thinks it's great and we get to have fun on occasion.

So for the past year we had set up these "Challenges" that if you lost you had to do what the other asked. So before our game we would discuss what the challenge would be and once agreed upon the loser either had to produce a picture of proof or we would meet up. Throughout the year I've had to wear my bikini bottoms to do laps, sports bras under my t-shirts to workout in especially spin class... Over New Years I guess I was drunk enough to agree to going out to a public place fully dressed. And try as I might, I lost. I have never been outside of my house fully dressed. So last weekend we went out to Goodwill where she picked out a dress, shoes, and tights. And we planned on going out this weekend or possibly tomorrow. I have contacted a lady friend of mine at a local lingerie shop with my "challenge", she assured me that she would love to help me out with my challenge, now my wife's fiend doesn't know about our deal...

Wish me luck, I will post a picture once I pay up...

@--}-----
Michelle

[Krisi]

If you are doing this stuff with your wife's friend and not your wife, I will expect to see the bunch of you on the Jerry Springer TV show soon. You are heading for trouble.

[Lana Mae]

I have to agree with Krisi. No good can come of this. IMHO Hugs Lana Mae

[ronda]

good luck with all your challenges your going to need it and I think there are more then you know

[Julie MA]

I'm confused about who is who, and who knows what, and who the challenges are with and known by...But if your wife knows, sounds like she does or will know, have fun with your lost challenge. Maybe you lost on purpose...?

[SarahleeNH]

Based on what I read from the OP, no good can come of this. Imho, you and your friend are violating your wife's trust. You should seriously reconsider participating in this very ill-advised game, unless you are certain your wife is fully included and supportive. Just my opinion...

[Sissy_Michelle]

Krisi - " Jerry Springer" LoL, no... We always keep things in the open. No secrets is all.

Yes my wife knows about all the challenges and what I was asked to do. If she doesn't approve then we figure something else out. My wife and her best friend have been friends since they were in middle school. I've only known them for the last twelve years...

Thank-you Ronda for the luck, I am very nervous...

Being confused is a good thing, because if everything was clear the world wouldn't be such an interesting place.

And no I would never lose on purpose.

Thank-you for all your kind comments and well wishes.

@--}----
Michelle

[Taylor186]

Sound to me that, in the game you are playing, your win is a loss (for crossdressing) and your loss is a win. So your claim that you "never lose on purpose" is hard to interpret. It could mean that you never lose (a chance to crossdress) on purpose. You seem to lose, in the traditional sense, a lot based on the challenges you've performed. Assuming your wife is totally on board with this, why the charade?

[Sissy_Michelle]

Taylor,

No charade... The game was only for fun, something to do since we don't see each other very often. Although your lose / win description is too deep for me. Think more high school grad, and less PH.D. / counseler.

@--}----
Michelle

[ClosetED]

So I see 2 options - since you don't fully dressed often and are not sure of how good you will look in public, then either let the friend and / or wife dress you and do makeup, or go for it all and have the lingerie shop friend or professional makeover do you to your very best and wow them all!
Can't wait to see pics!
Hugs, Ellen

[Acastina]

If this were all behind your wife's back and she was unaware of it, I'd be inclined to side with the voices of doom, but it sounds from your subsequent messages as if she's OK with your separate friendship, and may be relieved that you have that outlet for your CD needs without her having to participate directly in it. I'm sure you're aware of the possibility that you might be playing with matches?

As for venturing out, certainly lots of us here would encourage you to try it. It can be harmless fun or nerve-wracking, depending on who you are, where you go, and what you encounter. Just be careful and observant; not a good time to tie one on.

I just don't see great danger here as long as your wife is in the loop and isn't put off or made jealous (or similar) by your time with her friend. Not every XX & XY close friendship leads to trouble.

[Jenny22]

Acastina said, "playing with matches", but it sounds more like Dy-no-mite!!

[Sissy_Michelle]

Good Evening Everyone,

I hope everyone is doing well and taking precautions with the snowfall?

Before all the crazy drivers, and after I got off work I went home and changed into my outfit. This is the first time I have left home fully dressed. I went over to a lingerie shop that I frequent from time to time, came out to the owner and we spoke for about an hour and a half. Wasn't paying attention when the first two customers walked in but all they did was smile and the owner excused herself to help them out since I was just sitting and chatting with her. Once her customers finished their purchases I said my good byes and returned home. I did wear an overcoat to and from the shop, but for an hour and a half it was just me the owner and her customers. She told me I am more than welcome either as I am dressed now or otherwise.

I am so very happy.

@--}----
Michelle

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[BLUE ORCHID]

Hi Michelle, Keep us advised of your fun and games, It sounds interesting ,

Good luck, I hope that it doesn't blow up in your face......

[Barbara Black]

OMG give it a break with the 'danger'. Would you rather she doesn't have any friends other than her wife? I have none because my wife is so suspicious I could never freely go out, even with the guys, without suspicion, since we were dating. And now that she knows I crossdress, she's even more paranoid that I'm gay or bi. virtually ruling out going to meet someone while dressed or not. I was wrong to allow it, I should have risked it 'blowing up in my face' many years ago. Is marriage worth a suppression of your entire life? I certainly don't think so and I still love her, but have suffered for it.

[Krisi]

OMG give it a break with the 'danger'. Would you rather she doesn't have any friends other than her wife? ...............

OMG-give it a break with the "OMGs"!

Some of us have posted what we believe is sincere and "real world" advice. You certainly have your right to post conflicting advice but not to suggest that we not post our own advice just because you don't agree with it.

[karynspanties]

Well, I personally think that the wifes "friend" is working her way up to not only seeing him in lingerie, but getting him into the bedroom for adult playtime. I think she is way turned on by the thought of him dressed as a woman and things will be progressing to an affair. With what has been going on so far is kind of an affair already, just no sex involved................yet..............