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Deep down, he'll like it. It'll be super fun. We agreed that we're not going to laugh at him or make fun of him. He will be our servant some of the time, and he will be 'punished' if he performs poorly (spanking our little maid if she screws up), but we're not going to torture him.
I did bring up the idea of him 'servicing' us, we're still unsure as he's my boyfriend, but we'll talk about it more (friends are all single). We will demand that he strip for us and dance naked.
I can't wait to show him off at the mall.
I can't imagine anyone finding this "all in good fun".
The OP sounds like she's taking it a few clicks past "good fun", to the point of humiliation..... I suspect some man hating issues.......
I wouldn't never occur to me to do the things she's talking about him doing.....
Yeah I don't know. I wouldn't even do these things to someone I dislike. That's why I'm just brushing this off as a first time poster and a one hit wonder. lol
I hate to be the one to talk as though I am raining on the OP's upcoming parade here, but to put it candidly, some of the behaviors described show a distinct lack of boundaries and a serious lack of respect for your boyfriend
Dancing the "full Monty" for you and your girlfriends? Intimately *servicing* you and your girlfriends together all at once? Forcibly making him dress as and roleplay a female French maid? Spanking? Dumping tubs of food and beverages all over him? I'm sorry, but some these things that you are asking him to do are not only shocking, degrading, and humiliating, but are also simply very wrong and taboo. (For example, can one reasonably equate "servicing" as the equivalent of a "group orgy"?) Seriously??
If I were hypothetically in your boyfriend's shoes, I would literally not walk, but run away from you and your friends, as quickly as possible, and never look back. What you are doing to your boyfriend is simply *not* love!!
OP: please re-consider what you are doing!!
To be honest, yes, I would do this if the roles were reversed. I would dance naked. I would service him and his friends in that kind of situation. I would love to have food dumped over me and to get pied; it sounds hot. Frankly, it's all a turn-on.
Actually, the bet has already started. He came home early today because I told him to (it was fine since vacation is starting). I told him right away that he will be a woman for the next week and have to wear the clothes etc., that he's going to be a sexy french maid, that he's going to have to go out with us shopping etc, that he may service us if we decide.
Ya know what?
He's ok with it. Yes, he's a little shy and nervous, but I can tell from his reaction and his naughty smile it will be ok. I already took him to the spa. He was a good boy while getting his full body waxed (barely screamed); fortunately he doesn't have too much hair. He even seemed to enjoy the mani-pedi and kept looking at his pink nails with a smirk. he was quite the talk of the salon; all the manicurists and some other ladies there thought it was fun. I think he liked the attention. After, we picked up a wig, and he was willingly trying them on in the shop. I bought him a gorgeous blonde shoulder length wig; it looks super-real, as if it were his hair.
After we came home I gave him the first outfit and told him to put it on. He did so after a little nervousness. I then put makeup on him.
I'm not gonna lie; he looks awesome and is pretty convincing as a woman. It's almost kinda surreal how much he looks like a woman; only if you get face-to-face do you see some of the differences, but even then...
I showed him the mirror (his first time to see himself). After a big gasp of surprise, we smiled and started turning and checking himself out. He was enjoying it. He gave me a nice old kiss on the lips.
I told him to go relax; so he's watching tv now in his new outfit while I'm here updating you guys.
I talked to my girlfriends. They LOVE the idea. We're gonna take him shopping, have him serve us as a French maid, take him to the spa, give him a name.
What should his girl's name be? We will call him this all week. A real and feminine name is best (nothing silly or outdated, please).
I found the PERFECT french maid outfit. It's from Australia, so I called my old friend who lives there, she went out and bought it first thing and sent it rush delivery. Should be here Saturday morning. Here's a pic French Maid Outfit - Bras N Things
I already have my preparations planned. Tonight, Friday, after work I will take him to get waxed from head to toe, get his mani-pedi etc. Then we will go pick out a wig (I found a nice quality shop with real human hair wigs; pricey but worth it).
Saturday, the girls and us will go shopping at the mall. I already picke dup one outfit that he can wear when we go shopping (it's just a cute grey top top and a fun blue skirt from Forever 21 plus bra and panties). We'll shop til we drop. My friends and I are going to treat him to a new wardrobe (they all wanna pitch in) so he can have at least one outfit per day, and maybe more.
What kind of outfits should we buy?
What kind of lingerie should we get him?
The rest of Saturday he will serve us in the french maid outfit. Sunday we might go to the beach with him in a bikini.
It's going to be an awesome week.
I smell a [male] troll with an over active imagination - maybe a bit too many Penthouse Forum letters!
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Forcibly making him dress as and roleplay a female French maid? Spanking? Dumping tubs of food and beverages all over him? I'm sorry, but some these things that you are asking him to do are not only shocking, degrading, and humiliating, but are also simply very wrong and taboo. (For example, can one reasonably equate "servicing" as the equivalent of a "group orgy"?) Seriously?? 
