ANSWERS: 35
  • you pay a gay guy $50, and tell him to standby. then you meet with this boy and tell him if he doesnt wear a dress, youll get the gay guy to frenchkiss him. if he still refuses to wear the dress, he's gay. so, now, you pay a girl $50...
  • Tell him you're going to a costume party and that if he really loved you he'd let you dress him
  • My step sister had a guy who really had a crush on her. She told him to wear a dress and she'd go out with him. He did. She didn't.
  • Take him somewhere to try on clothes. Once he gets undressed take all his clothes from the dressing room. Bring him some girl clothes and tell him he has to dress like a girl or go home naked!
  • Well, apparently my brother is doing it this year just because he wants to. So, I guess if you just leave it up to them, they'll figure it out themselves.
  • You don't.
  • hypnotize him
  • Some boys you can trick other boys will let you dress them like a girl if you ask, most boys will do anything for a girl, so you can trick a boy to dress like a girl just by asking him. jk
  • Hide all of his underwear and pants, then replace it with skirts and panties. This usually works if you live in the same house as him. Bet him something that he thinks he can win, but you nkow you can win, then make the steaks high. Take him somewhere to get changed, tell him to hang his clothes over the side, thgen replace all of his clothes with girls clothes. Be ready with the camera. This works especially well if he is changing underwear. Play truth of dare with him, and dare him to do that.
  • tell him if he will trade clothes with you, you will change infront of him.
  • trick? you cant trick him i would guess he'd have to be willing... maybe say its a costume party and everyone is going as the opposite sex
  • get them very drunk and bet that they wouldn’t!
  • Alot of alcohol.
  • I would bet you back for a specific amount of money and then go shopping with you. I'd just buy a pair of jeans and a tshirt in the women's department. No biggie and I'd be ahead some cash w/out being embarrassed. No tricks required.
  • Offer him money.
  • Oops... wrong box!
  • get him drunk
  • Watch the movie "Sleepaway Camp" and you'll see...
  • Hide all his clothes and replace his entire warddrobe with beautiful skirts, lehenga, feminine dresses, nighties, earings, wigs etc.., Force him to wear these clothes for one day and tell him that he looks so nice and beautiful in pink skirt. tell him to wear nighties during sleep. Tell him it's a WOMENS WORLD.Make him wear a beautiful satin dress and take photos. Slowly make him to wear all girls clothes, take him to all girls party dressed as a girl. Treat him as a girl, make him to walk, talk, cross legs, behave as a girl. Sheenal
  • Tell him you will have sex with him. Take off your clothing and hand it to him -to put on. Once all is exchanged he can take it off. :)
  • If you are the girlfriend/wife just tell him either you wear what I put out or I won't put out! I would almost guarentee he'll agree.
  • ake your time first do pan and work your way up. a recent poll showed 88% of boys would or will wear dresses or skirts.
  • Tell'em the draft has been reactivated!!!
  • Offer to take your clothes all off if he'll put them on.
  • i love to wer that clothes if sheenal offers me
  • pressure
  • Tell him that it really really turns you on, and if he does than you will do him!!!
  • just call me and i will
  • Take him capming bring all your cloghs and camras tell him u will pack his stuff 4 him ( pack nothing 4 him ) and when u get to the camp sight get him dirty and and when he changes he has no choce then go home or when he falls asleep hide all his cloghs in your room replace it with ure cloghs or pay him $100 ( Evan U Dount Have The Mony ) Or hide All His underwear make him Pee Him self Put Some of Ure Most Girlyest Underwear in His Underwear Drowr then Pance him infount of his girl friend ,mom and dad, Or Friends or make a bet in wich he thinks he can win ( But He Cant )and every time he loses the bets he has to put on 1 gily thing 9 make sure u say And U Cant Quit ) Or tell him the hole school is making guys wearing dresses and making girls wearing boy cloghs Ps sorry a bout Grammer
  • Get A Bunch Of girls And Force all the girl stuff on him 1 boy Vs 7 girls ya the girls will win
  • Get him drunk first.
  • With the help of a bunch of girls, something like a 6 or 7 girls you can do it!!! My favorite hobbie is put my boyfriend in girls clothes, from head to toes, almost all the weekends I transform him in a beautiful woman, first a pink frillie panties, a pink garter belt, sheer stockings, pleated miniskirt, nice top, open toes high heels, a wig, full makeup, with false lashes, false red nails, earrings. and sometimes for fun, I invite other women to dress him, the last time we dressed him like a french maid, and with his outfit on, we went to a lingerie store, and with the help of the sales girls and costumers, we did a lingerie pageant, taking turns to undress and dress him in different lingerie outfits to see what is more femenine for him, and in the end, we take turns to touch and masturbate him. Now, my friends, do the same to their boyfriends, brothers, or cousins, and we help us to do this, because is more easy with 5 or 6 girls to put a man in girls clothes and is very fun.
  • Give him to the wrong parents.
  • If you were to check out the mister polls a lot of girls would find out that boys from age 7 to 107 would wear dresses, skirts, and the like. Most don't even have to tricked, but would do it almost willingly, with a few exceptions. If possible, either thru petition or whatever there should be a national crossdressing day.
  • when he is taking a shower, turn the heat on so mist covers evrything. then replace his shirt with a girly one, pants with skirt, shoes with girl shoes (if he uses chapstick, replace it with lipstick) (if he uses a thing so he doesnt bite his nails (i used it once) replace it with nailpaint) etc.

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