So… that happened… Megan’s thread

Okay, called Gary. Went very well. I was very up front about being sexually interested in him and that my husband has given up any voice in who I sleep with. He is open to talking about it but wants to get to know me more. Set up to get drinks tonight “just to talk” where I want to explore if he is comfortable with kinks while I flirt. I decided to make Hubby more explicit in this and let Gary know that hubby knew I was calling him and that he would be in the same restaurant for our meeting buying all our drinks. He was okay this time but didn’t know how he would feel about it. Willing to try is good to me!

Trying to decide what to wear and then have Sissy dress me for my date before we leave.
Ohhhh, my...
Wear something low cut and slinky with plenty for Gary to see, and plenty to make a grand suggestions of eroticism. Make sure you whisper to him that you're wearing lace panties, And it's up to him if he wants to take them home in his pocket tonight.
 
Selected a pretty but not slutty dress. Going red underneath: satin bra and matching panties, garter belt and thigh highs. Only 3” heels, I don’t want to be taller than Gary. Hubby will dress me soon.

For hubby, he’ll be caged (of course), satin sissy panties with ruffles bows and “Sissy Entrance” written across the bottom… satin bustier with small breast forms that will mostly be hidden under his loose button down shirt… garters from the bustier to his own black sheer thigh high stockings…. Slacks and men’s shoes. His haircut is kind of pixie but unless he’s wearing a dress or all women’s clothing it registers as kind of unisex/kind of femme. He likes it and going to get his hair styled at the women’s salon.
Sounds femmed up!
 
Selected a pretty but not slutty dress. Going red underneath: satin bra and matching panties, garter belt and thigh highs. Only 3” heels, I don’t want to be taller than Gary. Hubby will dress me soon.

For hubby, he’ll be caged (of course), satin sissy panties with ruffles bows and “Sissy Entrance” written across the bottom… satin bustier with small breast forms that will mostly be hidden under his loose button down shirt… garters from the bustier to his own black sheer thigh high stockings…. Slacks and men’s shoes. His haircut is kind of pixie but unless he’s wearing a dress or all women’s clothing it registers as kind of unisex/kind of femme. He likes it and going to get his hair styled at the women’s salon.
I want to be your next date!
 
I want to be just like Megan when I grow up.
And of course dressed just like her.
 
I want to be just like Megan when I grow up.
And of course dressed just like her.
U cant grow up, now what if Megan wants a real man, like me?


KZjQSS9.jpg
 
Hi girls and boys!

Mmmm I had a lovely date with Gary. Supposed to be drinks but became dinner too (which Hubby paid for it all). Gary and I got to know a lot about each other. He had moved to town last year for a job at the university. Was married earlier in his life but is divorced now, no kids. Our tastes in movies are different but he also plays Dungeons & Dragons from time to time.

He was very complimentary and made me feel beautiful. We definitely were flirting. I was open with him about my past and current situations sexually including sleeping with women and my husband’s development as a sissy and as a cuckold.

He took it in stride I would say. Told me he liked women’s panties too. I had him wait at the table, stopped by hubby’s table to tell him what I was doing, went to the ladies, removed my panties, returned to the table and gave them to him. He tried to hide from others seeing him but I watched him sniff my panties deeply and he was quite turned on.

Even though I was quite aroused with him, I held off doing anything further sexually with. Let him build up his interest. ;). Told him to call me so we’ll see how long it takes.

Hubby very much enjoyed watching us and being forced to pay for his wife to date another guy.
 
Hi girls and boys!

Mmmm I had a lovely date with Gary. Supposed to be drinks but became dinner too (which Hubby paid for it all). Gary and I got to know a lot about each other. He had moved to town last year for a job at the university. Was married earlier in his life but is divorced now, no kids. Our tastes in movies are different but he also plays Dungeons & Dragons from time to time.

He was very complimentary and made me feel beautiful. We definitely were flirting. I was open with him about my past and current situations sexually including sleeping with women and my husband’s development as a sissy and as a cuckold.

He took it in stride I would say. Told me he liked women’s panties too. I had him wait at the table, stopped by hubby’s table to tell him what I was doing, went to the ladies, removed my panties, returned to the table and gave them to him. He tried to hide from others seeing him but I watched him sniff my panties deeply and he was quite turned on.

Even though I was quite aroused with him, I held off doing anything further sexually with. Let him build up his interest. ;). Told him to call me so we’ll see how long it takes.

Hubby very much enjoyed watching us and being forced to pay for his wife to date another guy.
Sounds like you had a great time, thanks for the update.

I'm sure Gary is thankful too, for your panties, that he's probably got wrapped around his aching cock right now, thinking of you as he jacks off.

Did your date leave you hot and wet? Gonna get some fun in with your Sissy, or have some masturbation fun tonight?
 
And when's the last time your Sissy had some cock - just that one time with your vendor stud? He needs another does of cock and cum. Maybe if things go well with you and Gary, at the least your Sissy can lick your well fucked pussy clean of his cum when you get home, as you tell him all the nasty details.
 
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