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I've recently been talking to a guy online who will let me come over to his place so I can dress up. He says he likes people like me. I don't really fancy guys although he seems quite nice - I'm so mixed up. He says he wants to let me spend the weekend as a girl and i really want to do this. Help...?
ilikedresses ilikedresses 16-17, T 5 Answers Jul 10 in Dating & Relationships

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well if your young person and they are older be cautious ... There isnt anything wrong with dressing up in girls cloths, Embrace yourself no matter what.

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he's 30. thank you for your advice

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He is getting around that age where he might be liking younger. And i am 30 as well so I can kinda guess...You say he wants to let you spend the weekend as a girl kinda hints towards more... spending a entire weekend with someone that you might not fully be aware of the intentions can be risky...If you wanna spend a weekend dressed as a girl that is great :3 and not being into guys that way is fine as well, as to the relationship of you and him, besides he lets you do this, I dont fully know so to offer more advice in regards to the other guy id have to understand more about it..If i take it as completely null in the sexual department and hes just giving you a place to be yourself that is ok, is he buying things for you or taking pictures might be a indicator

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I know he wants more but understands that i am not sure about it. we've been talking for a while now and yes he has also said he will buy me some clothes - enough for the weekend anyway so i dont have to take any of my sisters with me.

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Make sure that if you decide to go that you know where it is your going and let someone know, even give a call to a friend or something now and then to let anyone know your ok .. If i could id go with to make sure nothing happens but that wont likely happen, just make sure you think it through and if you find yourself uncomfortable dont feel bad saying you wanna go home
Does he also dress up with you?

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that sounds like a good plan. no he doesn't dress up at all. he just likes girls like me.

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Well by the sounds of it his intentions are leading to a place we probably dont wanna go.... But then my question would be ... What if it does go there? Are you ready to handle it?
Why do you not let others know (besides online as it appears XD) that you like to do this ? You could gradually ease into it... Hell my own mother gave me girls stuff because she figured it would look good on me, now i got a very male face but slender body that most would kill for, but she started with stockings when i was at work cuz i would freeze she said they held heat better... to some degree it was true...for awhile there my job forced me to handle a lot of female clothing, which i loved the feel of some of it and after awhile I took my own curiosity to sort of a spending spree (once i got a steady job) buying all types of things. I dont see a reason you can ease in ether

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I think i am ready to try some stuff.

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Well, If i may .. How did you meet him? like was it 1st online then in person, from a forum/chat etc or like a friend of the family

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Without going into massive details he's not quite a random stranger.

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with that quite there means ya have not exactly known him long ....Just remember do what is in your comfort zone if you remotely feel a entire weekend is a bit much specially in a unfamiliar place...You could just dress up and spend a weekend (as your intention is) even out each day going home at night. or head out into public areas like out to a movie place, bowling and what not... I just dont wanna see em head the way of forcing something that your not 100% on(as you said you dont really fancy guys, and sometimes its the nice guys you gotta watch out for)...
Well be prepared :3

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hi there - thanks for that. i'm going over tomorrow to spend the day but won't stay the night just to see how it goes.

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have fun :3

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Hi. Just to let you know i am back home now. Had an amazing day.

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Thats good .. What all did ya do? anything special or fun?

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He'd bought me some clothes and make up and left me for a while to get changed. We watched some films, had a meal and just really spent the day together. Loved the way he treated me

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What he get ya :3 ?.. also what movie(films) XD ... Did he make the meal or was it something like take out (delivery)?

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He got my some undies, a skirt and top and a dress as well. Some nice sandals to go with everything. We just watched the hunger games. No he didnt cook it was take out

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so more like a mid summer outfit... I have not seen the hunger games yet, Im told its a good one..Awe thats too bad it was takeout but hay its better than nothing :3 did ya plan to do it again?

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Yes hunger games was good and so was the food. Yes we are going to do it again. It was amazing

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Perhaps ill watch it... I take it he is going to keep the outfit, since your still shy about it at home :P

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yes he is keeping the clothes for me in his spare room.

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Well , hopefully you fallow your instincts ... Just remember the danger is always out there ..humans are naturally violent, so be cautious.
But i still root for your happiness ;3

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yes i will do - thankyou. x

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niceeeeeeee

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so its something i should do?

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I would say if you have to ask someone if you should ... then your hearts not fully for it.. Dont leave your own comfort zone :3

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