Vulvasailor

My Fantasy

24 posts in this topic

Sex is fabulous but even that can get monotonous and boring after a while so how many of us truly explore our fantasy.

My real desire is to be dressed up as a woman by a WG. Wig, make up the lot. I need to look good not like Lily Savage. It would involve social scene, therefore a meal and a stroll around town. I could not do stilleto heels but would quite happily shave my legs, get false tanned and whatever. The emphasis would be on the WG making me look how she wanted me and then when get in the bedroom I roger her silly but I'd be very sub and do whatever she told me to do.

I've dressed as a woman in a group of lads before and thought it quite hilarious but very sexual. Women were falling at our feets - honestly. This is not a fantasy I could conclude with a non WG but only with a WG and I'm just about thinking what the hell go for it. I'm virtually certain this would occur then I'd never punt again.

Would be interested to hear what WG's think. Is this common theme ?

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Sex is fabulous but even that can get monotonous and boring after a while so how many of us truly explore our fantasy.

My real desire is to be dressed up as a woman by a WG. Wig, make up the lot. I need to look good not like Lily Savage. It would involve social scene, therefore a meal and a stroll around town. I could not do stilleto heels but would quite happily shave my legs, get false tanned and whatever. The emphasis would be on the WG making me look how she wanted me and then when get in the bedroom I roger her silly but I'd be very sub and do whatever she told me to do.

I've dressed as a woman in a group of lads before and thought it quite hilarious but very sexual. Women were falling at our feets - honestly. This is not a fantasy I could conclude with a non WG but only with a WG and I'm just about thinking what the hell go for it. I'm virtually certain this would occur then I'd never punt again.

Would be interested to hear what WG's think. Is this common theme ?

I cant see that will be a problem for any WG.

However: would you be prepare to pay an hourly rate (£100 p/h at least) for her time to dress you, make up, make your hair/ fit the wig, etc. You might not look like Lilly Savvage, but not far off (after all most of the guys dressed in women attire do, apart of Gary Skyner). Never mind, its irrelevant, and I am sure many girls would not even charge for this part. (money for an old rope and all that, lol)

Ok, I understand thats you consider it to be quite a good craic while you doing it in the company of your mates. Totally hilarious: semi inherbinated girls on the street or in the bar gripping your crotch, balls, pinch your arse, smooch your lips and so on. After all: you would not be able to get all that, if you will be dressed like an ordinary guy. ;-)

What I don't understand, why do you think if you going to be dressed by WG and somehow make an impact in public, going to cure you from the punting?

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However: would you be prepare to pay an hourly rate (£100 p/h at least) for her time to dress you, make up, make your hair/ fit the wig, etc. You might not look like Lilly Savvage, but not far off (after all most of the guys dressed in women attire do, apart of Gary Skyner). Never mind, its irrelevant, and I am sure many girls would not even charge for this part. (money for an old rope and all that, lol)

Yes I'd happily pay. Where are these happenings common place though? I wouldn't classify myself as a tranvestite or a cross dresser of sorts. I am certain there are women, most likely some WG's who would instantly moisten at the sheer thought of it. It's very bizarre.

Ok, I understand thats you consider it to be quite a good craic while you doing it in the company of your mates. Totally hilarious: semi inherbinated girls on the street or in the bar gripping your crotch, balls, pinch your arse, smooch your lips and so on. After all: you would not be able to get all that, if you will be dressed like an ordinary guy. ;-)

No and I suppose a group of lads dressed as roosters would have the same effect.

What I don't understand, why do you think if you going to be dressed by WG and somehow make an impact in public, going to cure you from the punting?

Maybe cure is the wrong word but nothing would ever live up to that afterwards. The plateau of sexual realisation is within grasp.

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Maybe cure is the wrong word but nothing would ever live up to that afterwards. The plateau of sexual realisation is within grasp.

I'm not convinced. If you do get the high you are expecting, I suspect you will try and get that high again, and maybe take it further than the time before. It is just human nature.

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Hehe I presume that this booking would include a shopping trip, I doubt very much WGs have all that stuff in their wardrobes??

The ultimate last punt!

I agree with WayTooTall for many it is all about pushing their boundaries and once completed the next thing is planned where does it all stop??

S x

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I cant see that will be a problem for any WG.

*Puts hand up !

Each to their own but I wouldn't be seen dead trapsing around Harvey Nicks with a ropey tranny in tow.

Edited by Helen Jones

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Sex is fabulous but even that can get monotonous and boring after a while so how many of us truly explore our fantasy.

My real desire is to be dressed up as a woman by a WG. Wig, make up the lot. I need to look good not like Lily Savage. It would involve social scene, therefore a meal and a stroll around town. I could not do stilleto heels but would quite happily shave my legs, get false tanned and whatever. The emphasis would be on the WG making me look how she wanted me and then when get in the bedroom I roger her silly but I'd be very sub and do whatever she told me to do.I've dressed as a woman in a group of lads before and thought it quite hilarious but very sexual. Women were falling at our feets - honestly. This is not a fantasy I could conclude with a non WG but only with a WG and I'm just about thinking what the hell go for it. I'm virtually certain this would occur then I'd never punt again.

Would be interested to hear what WG's think. Is this common theme ?

As a 100% hetero, I find it difficult to identify with this fantasy but hey, each to.........!

What I find interesting is the assumption or implication that girls and in particular the WG here might be 'turned on' by being shagged by a transvestite ( albeit dressed to her liking ) !! Is there something to this ?? Have I been missing something? Should I consider buying a dresss ??

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May be useful in Primark - holding back the crowds...

*Puts hand up !

Each to their own but I wouldn't be seen dead trapsing around Harvey Nicks with a ropey tranny in tow.

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What I find interesting is the assumption or implication that girls and in particular the WG here might be 'turned on' by being shagged by a transvestite ( albeit dressed to her liking ) !! Is there something to this ?? Have I been missing something? Should I consider buying a dresss ??

It's a matter of taste - I'm sure there are lots of women not into it at all, and lots of women who think it's the hottest thing ever. We're not all the same ;) I've never been with a transvestite but it's something I've always quite fancied trying - I'm bisexual and it just seems like a great way to get the best of both :D

That said, I wouldn't be up for the challenge of dressing and making over a stranger. I have a few friends who are spread over the transvestite/genderqueer/transgender/transexual spectrum and have done a few makeovers on physically male people - but I knew them well, and I was confident that I'd be able to make them pretty (they had fantastic bone structure!). I would hate to do a bad job.

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I trained as an actor and as a 22 year old did a part in drag- not drag queen but gender ambiguous. I was supposed to look pretty and feminine and I did- as I was quite slim then with better eye lashes than the girls! I spent a lot of time off stage in drag with the girls and they would forget that I was male and say things in front of me that men would normally be excluded from.I really fancied one actress who had long brown hair and beautiful brown eyes. After the first night party we had wild sex together and I really think she fancied the feminine side of me but wanted the sex she couldn't get from another actress.

It's a matter of taste - I'm sure there are lots of women not into it at all, and lots of women who think it's the hottest thing ever. We're not all the same ;) I've never been with a transvestite but it's something I've always quite fancied trying - I'm bisexual and it just seems like a great way to get the best of both :D

That said, I wouldn't be up for the challenge of dressing and making over a stranger. I have a few friends who are spread over the transvestite/genderqueer/transgender/transexual spectrum and have done a few makeovers on physically male people - but I knew them well, and I was confident that I'd be able to make them pretty (they had fantastic bone structure!). I would hate to do a bad job.

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Sex is fabulous but even that can get monotonous and boring after a while so how many of us truly explore our fantasy.

My real desire is to be dressed up as a woman by a WG. Wig, make up the lot. I need to look good not like Lily Savage. It would involve social scene, therefore a meal and a stroll around town. I could not do stilleto heels but would quite happily shave my legs, get false tanned and whatever. The emphasis would be on the WG making me look how she wanted me and then when get in the bedroom I roger her silly but I'd be very sub and do whatever she told me to do.

I've dressed as a woman in a group of lads before and thought it quite hilarious but very sexual. Women were falling at our feets - honestly. This is not a fantasy I could conclude with a non WG but only with a WG and I'm just about thinking what the hell go for it. I'm virtually certain this would occur then I'd never punt again.

Would be interested to hear what WG's think. Is this common theme ?

Its great that you've shared this with us. I'm a trannie and there's so much you fun you can have with dressing up and fantasy. I love playing around with gender stereotypes and roles. It's very moreish so I'd be surprised if you stuff punting after doing it once, tho.

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Sadly there are some WGs that don't take it well when you dress up "differently". This has happened before. When she sees you undress and then notice you are wearing something guys normally don't, she tries to contain herself from laughing and it goes downhill from there.

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I offer a make-over/feminization service and have met several clients who

welcome finding a lady who is comfortable with this.... which in turn of

course makes them comfortable and not self concious.

However I had to end meetings with one young man ( who actually looked

quite stunning when feminized ) as he kept asking me to go out with him

in public... shopping etc while he was dressed and made up.

Discretion would have gone out of the window so I had to say no and I hope

he found a lady who obliged him.

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It's stirred some debate and some interesting replies.

It's no taint on my sexuality as I am 100% hetero. What turns me on is the mischief factor and that some women find it a turn-on. Perhaps the public aspect is a step too far and one that would have to go by the by.

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It's stirred some debate and some interesting replies.

It's no taint on my sexuality as I am 100% hetero. What turns me on is the mischief factor and that some women find it a turn-on. Perhaps the public aspect is a step too far and one that would have to go by the by.

Vulvasailor, I have to say your a brave man to share this with us and I applaud you for such candor. I have a similiar fantasy where I like to dress as a middle ages Witch, Mrs Diva then takes on the role of the village Squire and proceeds to 'cleanse' me in the home made witching stool we have built over our hot tub. Another ones is Mrs Diva dressed as a female Gestapo officer, this time I play the role of a female SOE operative dropped into the French Countryside in 1942, my mission is aborted and I am captured by Mrs Diva and 'tortured'. As I only achieved a C in my GCSE French I soon blow my cover and starting singing like a bird.

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I have some empathy with you Vulvasailor but for slightly different reasons.

Firstly, I broadly have the same fantasy but I think you would be very brave to go out in public. Having seen two work colleagues in the past become tranvestites, it can be very tough emotionally to expose yourself to potential ridicule in the outside world. I would first think about trying it behind closed doors.

I once had an experience of spending two hours being dressed in drag and made up by several young attractive women (for a work related event.) I found it very stimulating and thought about exploring it further. My fantasy would be to have a similar dressing up session but then to have sex with a dominant woman/mistress - preferably with a nice large strap on...

Edited by pvcman

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I always fancied the idea of being taken advantage of. This could fit many scenarios including female boss etc but it emanates from way back in my teens when I used to fancy a couple of the mothers of my friends, one in particular. I perhaps would be caught doing something I shouldnt,anything, something I would not want the authorities or my parents to discover. The lady would use this hold over me to have her way with me, to sexually blacmail me.

She would get me over to her house when hubby and family members were out.As she had a position of power she would would wear outrageuosly seductive clothes,perhaps changing a couple of times whilst ostensibly seeking my opinion but obliging me to masturbate in front of her to prove how attractive she was. She would then require me to bathe her properly and afterwards when she had put on the hottest heels you could imagine, she would then lead me downstairs to her drawing room and recline on on a luxurious chair, make me kneel in front of her and after some body worship, would order me to lick her vagina for hours until she came and came and came.She might also ring her husband to chat about a few things , whilst unbeknownst to him, I continued to lick her vagina and to rim her while she talked to him.

Unfortunately, I can never act this out with a WG, as the whole premise of the fantasy is that the lady is genuinely deriving intense sexual satisfaction from ' using ' me. In a paid sex scenario this can never be fully relied upon.

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Ok, I understand thats you consider it to be quite a good craic while you doing it in the company of your mates. Totally hilarious: semi inherbinated girls on the street or in the bar gripping your crotch, balls, pinch your

Xenia, I would genuinely miss you if you weren't here on the board. From who else would I learn words like "inherbinated"? :D

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Mmmmh, I have a sneaky suspicion that the women who fell at the OP’s feet in his get up of femme fatale were probably pissed as newts rather than overcome with genuine desire :rolleyes:

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*Puts hand up !

Each to their own but I wouldn't be seen dead trapsing around Harvey Nicks with a ropey tranny in tow.

I would not like that also, Helen! (but then if you paid for it, you after put up with it).

But if choosing of the lesser evils: I would rather been seen in public with a client dressed and made up in the a woman drag, then when he is totally natural with bald patch, chinos and kind of shoes which your Geography teacher use to wear when you was in school. :-)

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Mmmmh, I have a sneaky suspicion that the women who fell at the OP’s feet in his get up of femme fatale were probably pissed as newts rather than overcome with genuine desire :rolleyes:

Without a doubt, although when inherbinated we do tend to somewhat lose our inhibitions.

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I would not like that also, Helen! (but then if you paid for it, you after put up with it).

Not for all the tea in China Xenia. At least I could say my Geography teacher was a disabled special needs patient and I was a carer, showing him how to cope with the Chavs in Primark :D

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Sex is fabulous but even that can get monotonous and boring after a while so how many of us truly explore our fantasy.

My real desire is to be dressed up as a woman by a WG. Wig, make up the lot. I need to look good not like Lily Savage. It would involve social scene, therefore a meal and a stroll around town. I could not do stilleto heels but would quite happily shave my legs, get false tanned and whatever. The emphasis would be on the WG making me look how she wanted me and then when get in the bedroom I roger her silly but I'd be very sub and do whatever she told me to do.

I've dressed as a woman in a group of lads before and thought it quite hilarious but very sexual. Women were falling at our feets - honestly. This is not a fantasy I could conclude with a non WG but only with a WG and I'm just about thinking what the hell go for it. I'm virtually certain this would occur then I'd never punt again.

Would be interested to hear what WG's think. Is this common theme ?

I have seen someone who came to see me dressed as a man then changed into womans clothes and put full make up on. I was aware before he came that this was going to happen so no shocks there. It turned out a really fun sexy appointment, like you say the norm can get a bit monotonous sometimes so there is nothing wrong with adding a bit of fun.

Shelly

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I have seen someone who came to see me dressed as a man then changed into womans clothes and put full make up on. I was aware before he came that this was going to happen so no shocks there. It turned out a really fun sexy appointment, like you say the norm can get a bit monotonous sometimes so there is nothing wrong with adding a bit of fun.

Shelly

This isn't an uncommon fantasy, and I too have entertained cross-dressers(correct me if I don't use the correct terminology!). The going out in public bit would be difficult in my small town.

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