31/M/Heteroflexible XDresser - Honest and detailed answers!

[Crossdress_Bitch]

I'm feeling fairly open (maybe in more ways than one? hehe),
so why not ask me a question?

Can be any topic you like, I've nothing to hide here*

*except my name and address


Thanks!
I hope you enjoy my thread

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[Guv'nor]

Rank the types of panties, from your favourite to wear, to least favourite. Explain why for each type.

What do you enjoy about crossdressing?

Have you ever had to service a man whilst crossdressed?

[Crossdress_Bitch]

Wow, straight in with some great, potentially deep and very fun questions. Thank you, sir! I will try my best to be thorough in my replies!

Originally Posted by Guv'nor

Rank the types of panties, from your favourite to wear, to least favourite. Explain why for each type.

1) I'd say my personal favourite is French cut/cheeky/boy short, whatever people want to call them, like I am wearing here. This is because they comfy, yet sexy, and the slight slide of the material into the crack is a nice reminder that you've got them on, even when going under boy clothes. Plus they flatter my ass, hehe

2) Next I'd probably go for a fuller cut, a bit like I'm wearing here. The reason I go this way and not for something smaller is because I like the variety on offer (favourites would include anything satiny for the feel, or anything lacey/meshy for the look and femininity) and also like having more feminine material to feel against my skin, not less. Plus I'm just a sucker for classic, "classy" looks.

3) I also quite like the recent popularity of backless knickers, like this. I have a few varieties of these, but no pics on GD of me in them (yet?). I like that these have the combo of being able to have my cock encased in some nice, usually satiny material, but also give me the chance to show off my ass in a different way. Plus, well, easy access without taking them down, which is great to allow to keep feeling those soft sensations throughout play

4) Next would probably be thongs and I do have some nice ones I really like (there aren't really any losers in panties. I love all sorts, haha!) and my butt looks good in them, but it's just not as much my style for dress up.

5) Finally, I guess the least fave would be strings. Not as flattering on the butt, and generally too small to be comfortable in when you're packing guy parts! That said, if it weren't about looking or feeling feminine, but purely about embarrassment as a man in that moment, that's certainly an angle that can be fun in its own way.

Originally Posted by Guv'nor

What do you enjoy about crossdressing?

Now this is a big question, with a multi-layered answer even I wouldn't know all of. It is, of course, like all kinks, a visceral instinct that I can never fully understand, but I'll try my best! In a previous thread I wrote that "it makes me feel naughty and kind of sexy at the same time. Hard to explain. I enjoy feeling feminine sometimes just as much as I like feeling masculine at others - except feeling feminine also turns me on. I guess you could say I'm a self-appreciating male lesbian." Which remains true, but I think there's more elements than that.

So, first all, I just like the materials and the feel. Second of all, I enjoy fashion and like being able to embrace its varieties. Third, I admire and am attracted to femininity and, for some reason, in me there is an arousal link there to experiencing that femininity myself. I find the idea of dressing up fun and arousing, I find being dressed up fun and arousing, and it helps that I also feel I can be quite good at it, and find the results attractive and arousing. Yes, even though it's me. I can look at my own pictures and think "wow, that's sexy, I can't believe it's me", which only makes it more exciting to me. I believe it's a form of what is called autogynephilia! Additionally, there's a bit of exhibitionism at play because, after I'm pleased by it, I feel this rush that I want others to see too. Hence sharing photos whenever I can

Beneath that, I expect there is also a psychological layer linked to my enjoyment of submission and (though I don't necessarily know if I like that these stereotypes may exist in my brain) a subconscious awareness of society's traditional gender roles. When I am en femme or thinking about being that way, I feel horny, but I also more suggestible - more willing to submit. However, I'd like to think this isn't just an ingrained misogyny society has put in my head and that there is more of a subversion at play. You see, I almost always want to submit to women. So my feeling and hope is that this isn't just "it's humiliating because you think a man to be put in the position of a woman is degrading, because women are less than men" (which I don't believe!), but can be interpreted as an role play power inversion of these traditional positions. That a strong, powerful woman who in fact is her own confident person and not submissive or coy at all can have fun putting me in a position to say "ha! This is what we had to put up with, now who's the so-called weaker sex? Do those chores, rub my feet, do as I say and come over here for a fucking."

And I, of course, will obediently say "yes, Miss, you are superior."

Originally Posted by Guv'nor

Have you ever had to service a man whilst crossdressed?

I have not. In fact, as it currently stands, I have never serviced a man at all and, up until as recently as a year ago, I would have confidently stated that I never will. But something seems to have changed in me recently, even at this age...

I credit subDanni's excellent story "what happens to horny sissies" with helping to trigger this awakening. It was so well written and tapped into my turn ons so perfectly, that even though it quickly gets into forced bi material that I previously wouldn't have had interest in, I just couldn't stop reading. I found it all so, so arousing to me! I think it was the fact that it was written in such a way, that a Mistress was always the leading power figure, so all the things done were to please her. It got me thinking "hey, if I was all dressed up and a Mistress wanted to train me to suck cock and service men for her amusement and pleasure, I could really be turned on by that" - which is something I never thought I'd think!

Whilst I still don't count myself as bi-sexual, owing to the fact that men in and of themselves never turn my head in the street (I have never had a crush on a man, or seen one and thought "whoa, I fancy him!"), the idea of a cock and what I could do to one (or what it could do to me! Eek!) has become a regular part of my fantasies. Often when I see a blowjob in porn or on a webcam now, I have hard time deciding which role I'd like to be in more that day, haha! And I'm not averse to the idea of being fucked either. Particularly, as I say, if a beautiful woman were willing it to be so. As such, I now feel comfortable and confident referring to myself as heteroflexible (or bi-curious, since I haven't tried yet), where I previously would have identified purely as straight.

But why so curious, Sir... are you asking? Hehe.

Thanks again for your questions. I hope I answered well!

[Crossdress_Bitch]

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PS: I promise not all my answers will be quite a long as those!
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[Guv'nor]

Thankyou for those amazing answers! Why am I asking? As I enjoy torturing sissies and crossdressers, obviously! :P

Have you ever been crossdressed in public?

Have you ever been in chastity? Would you? Why/Why not?

What sex toys do you have?

[Crossdress_Bitch]

Originally Posted by Guv'nor

Why am I asking? As I enjoy torturing sissies and crossdressers, obviously! :P

I meant more were you hinting at wanting a servicing yourself?

Either way, carry on torturing, by all means! That's what I'm here for.

So, onto the answers...

Originally Posted by Guv'nor

Have you ever been crossdressed in public?

Under clothes, loads of times! Fully though? Yes, but only on a handful of occasions spread over many years.

The first couple were nights out to different bars/clubs when I was about 18 or 19 where it had been advertised as a bit of a jokey theme night. Myself and some other friends did it very casually on these occasions (no wigs, no heels, minimal makeup). I doubt they would have been into crossdressing in the same way I was and this wouldn't have come across to anyone as anything more than some guys having a laugh. On both these occasions, barely anyone else turned up actually crossdressed at all though! Haha.

Next was when I found my first reason for a full on solo outing. Also during university, I set up a charity page where the more people donated to the charity, the more I would dress up for an outing to the pub (where I took a collection bucket and gathered more money for the charity). It was like: if I raise X amount, I'll wear a dress, if I raise Y I'll also wear heels, if I raise Z I'll wear a wig and makeup and if I raise the highest possible I'll wax my legs for the occasion. I raised the highest possible! This was my first full on view of myself looking as female as I had ever looked at the time. It was fun!

After this, there have been two occasions where different female friends have helped me dress up and we've gone out. One was for a club that put on themed (but pretty mild) "fetish nights". It was "Under the Sea" and we both went as sailor girls. Another was just a night out in a normal club in a city my friend lived in and I didn't. She went as a man in a suit and I went as a flapper girl.

The other occasions have all been Halloween. One time I went to a sing-a-long showing of the Rocky Horror Picture Show and went as Columbia. That same weekend I went to a party as a zombie Marilyn Monroe. And just the other year I went to a party as one of the skull-faced aliens from the film They Live, but because I'm very into Halloween and thought going as a male one was too easy (essentially just a 1980s rich man in a suit with a mask I could take on/off), I went as a 1980s rich woman instead with my face made up for her "human" appearance and the mask for her alien one. A bit like this.

Oh, and last Halloween I went as Old Gregg from the Mighty Boosh. Anybody that's seen that will know he's kind of... in between genders?

I think the next time I go out, I would like to for it to be at a proper, full on fetish night, or perhaps even a sex club. I'd need to be with somebody that could help me get ready and give me the support I needed to feel brave enough to go though! Photos are my main outlet for now... I can control my body language and posture more in them anyway

Originally Posted by Guv'nor

Have you ever been in chastity? Would you? Why/Why not?

Chastity is something I never really enjoyed, but have grown to find kind of sexy and thrilling for short periods... never anything longer so far than abut 7 - 10 days, and I'm not sure I'd ever want to go further. This normally works as somebody I'm going to have sex with (or online/distance fun with on occasion) setting the time period as a challenge with the promise of release with them on a certain date. If it didn't have that end date in place and with a level of trust where I know they might tease a bit on the day, but probably wouldn't actually say "no, not really, wait longer", I probably wouldn't like it and would just grow to resent it. For me, there always needs to be a realistic chance of release, or it's just not something I'd want to be involved in. That said, I also like the idea of "you won't be released until you complete [insert embarrassing or degrading task here] for me" - earning my release if you will. That's hot.

If you mean literal chastity tools, I don't often use these, but I do have a cock cage that I wore for around 5 days once at an ex's command, but I was working mostly from home at that point and didn't have to worry too much about the fact they can be quite bulky and uncomfy under modern men's clothes (slim jeans etc). I was mostly popping to the supermarket etc, which is fine, but now I have a proper job where I'm always interacting with people, I probably wouldn't risk it. Plus if it goes wrong and something suddenly gets caught or painful whilst you're out, you're kind of screwed! That said, I do have a CB clear plastic chastity device now too, just for the fun that it might get used in some context some day!

Originally Posted by Guv'nor

What sex toys do you have?

Gosh, just let me try to remember!

In addition to the two chastity devices mentioned above, I have:

- a spanking paddle
- a flogger style multi-tasselled whip
- clothes pegs and candles for pain play
- a small/medium sized buttplug with a jewel on the base and jiggling ball inside
- an inflatable, vibrating plug that starts off medium/large and gets, well, bigger!
- an Aneros Helix Syn anal toy that is meant to allow hands free super orgasms, but I haven't quite mastered it. Still fun though!
- realistic size 6 inch dildo with balls and suction cup
- a strap on harness for couple play, which can be used with the dildo above, or this kind of prostate probe it came with.
- I had a couple of mini vibes that as well as being good for female partners to use, could be used to stimulate my cock as if it were a clit, but I think the best of these has been left with my ex.
- wrist cuffs
- blindfold
- lengths of bondage rope (more for couple play)

I think that's all I can think of! But if I remember anything else, I'll let you know!

Thanks again for your questions!

~~~

[Guv'nor]

Once again, thankyou for those fantastic answers. You really do go into detail very well.

Me? Wanting to be serviced? Amazingly not! Well, I assume you want more questions? Either way, you are getting some.


How many sexual partners have you had?
Have you ever had sex in a public place?
What are your hobbies?
Do you buy your crossdressing clothes in person or online?
Has anyone ever asked why you are buying womens clothes? What did you say?

[Crossdress_Bitch]

Originally Posted by Guv'nor

How many sexual partners have you had?

Ignoring a bit of fondling about with one or two other people, I have had a total five sexual partners. Some would say that's not many someone my age, but I was never really one for one night stands (few reasons: partially a lack of interest/connection in having sex with a stranger, but also a lack of confidence/awareness of how to make one come about) and so often have dry spells between relationships.

To summarise:

1) lost virginity at 19. That relationship lasted a year with breaks. Then I had a 2.5 year gap of no sex.

2) Then had my longest relationship: over four years with my girlfriend (and sometimes Mistress) who also used to post with me on this site (though I was on here before her). Sexually my most rewarding relationship, but sex, of course, isn't everything and can't last forever without other factors. Unfortunately by the end, things weren't good and it had grown slightly toxic between us.

3) Had a long distance but very fun relationship with a polyamorous girl who I got to see once or twice a month. This lasted six months. Recently, after two years apart, she became my girlfriend again (just mine this time, monogamously) for around 10 months and we started living together. That sadly ended in June.

In between the two spells with #3 were:
4) my one and only one night stand, and with a woman around 17 years my senior! And, to my surprise, it was actually a very fun experience!

5) An on-and-off, very confusing and emotionally taxing 9 month friendship/relationship that had its fun moments, but also plenty of crazy, shitty ones I still don't understand. I try not to think about that one so much!

Originally Posted by Guv'nor

Have you ever had sex in a public place?

Not really, no! Maybe a bit in a shared hostel room once with other friends sleeping etc, but it was just a bit of fun and we didn't finish. Though we did later have sex in the bathroom of that hostel room whilst everyone else was out.

Originally Posted by Guv'nor

What are your hobbies?

I don't really have any active hobbies like sports or the gym, though I really should start. Nor do I have many that require talent, haha. As such, my hobbies are mostly films (going to the cinema and collecting blu-rays), TV/Netflix etc, music (collecting records and going to gigs - I don't play anything myself, unfortunately), and sometimes books and comics, though I don't read as much as I wish I did! Also drinking different beers, tasting different foods and trying, when I can, to visit different cities and take in different places and cultures.

I am also very into Halloween, so once a year for the month of October, making a costume for that is pretty much my hobby whenever I'm not at work. I am pretty good at dressing up (as perhaps my lady pictures show... I hope?) and each year normally find I have new ability I didn't know I had... whether it's creating my own props out of scrap and painting them up, altering clothes, doing a decent make-up/facepaint job, or making a mask out of clay. This year though I will be at a wedding on Halloween weekend and sadly it's not themed, so for the first time in years, I will be on hiatus!

Originally Posted by Guv'nor

Do you buy your crossdressing clothes in person or online?

Sometimes online, but quite often in person, actually! Even when buying man clothes, if I can get a look at something before I buy it, I prefer this. Though I don't try women's clothes on in stores unless it's just a t-shirt or something. I have previously taken them to nearby public bathrooms to check the size after purchase before taking them back and swapping them out if I've got it wrong though. I've bought plenty of underwear in person too.

Oh and last year I bought some faux leather trousers with plans to wear them to punkier/gothier gigs and outings on occasion, which I found in the ladies section and tried on in store, but I took them to the men's changing rooms and was deliberately buying them slightly big to get a size that fit more like a men's pair.

Originally Posted by Guv'nor

Has anyone ever asked why you are buying womens clothes? What did you say?

Funnily enough, it's never actually come up! Though it has been a fantasy that I might go shopping (particularly for lingerie maybe) with a girlfriend and we might make a dare/embarrassing game out of it becoming apparent that we're actually buying for me, not her. As of yet though, it hasn't happened!

Thanks again for taking interest in my thread! I appreciate all your questions and have fun answering them

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[andrew_b]

I absolutely love the story you wrote about charity night, takes balls to be that confident with it

[Crossdress_Bitch]

Originally Posted by andrew_b

I absolutely love the story you wrote about charity night, takes balls to be that confident with it

Thank you! Although as was said when I first wrote about that night on gD (waaay back in 2007 - wow!), it was actually easier to get away with because it could be played off as making myself look silly simply in order to raise more money for a good cause. People were entertained by it and respected me for it. Little did they know I kind of just wanted to do it in the first place, simply for the excitement!

Obviously I'm really glad and proud I raised (if I remember right) over £600 for charity, but it doesn't feel as brave as I feel I had to be on other public nights where I didn't have an "excuse" to fall back on. I'd love to do more public outings, but the fear of embarrassment and judgement is much higher when you've nothing to disguise that you just want to do it for fun!

[kila]

£600 for charity? Wow! That's amazing! Also, you have a nice ass and cute panties! I just have a couple of curiosity questions so I hope you don't mind

Which of your PM dares is your most favorite?

What would you say is the most humiliating task you have done?

Other than the leg shaving for the charity thing you've done, what else have you shaved/what is the most you have shaved off?

What is your favorite kind of hairstyle to wear when you crossdress?

What do you enjoy to roleplay as? Have you done it in real life?

[Crossdress_Bitch]

Originally Posted by kila

£600 for charity? Wow! That's amazing! Also, you have a nice ass and cute panties! I just have a couple of curiosity questions so I hope you don't mind

Thank you for the compliment, Miss. You've got me aroused already, so of course I don't mind answering your questions!

Originally Posted by kila

Which of your PM dares is your most favorite?

This might be predictable, but as far as my current PM dares go, I think I have to go with PANTIES. A bit of secret panty wearing can't be beaten for a simple, sexy secret to keep me horny and excited throughout the day, reminding me constantly of what a naughty slut I am...

Originally Posted by kila

What would you say is the most humiliating task you have done?

This is a tricky one! A few years back, my girlfriend/mistress used to be very good at degrading me - both in person, and with long distance tasks.

Some favourite examples I can think of off the top of my head would be:

- the solo task described by my story in the first post of this thread.

- then it would be a toss up between the multiple dom/sub sessions we had together. It's been a few years, so a lot of these blur together in my mind now, but two I can refer back to with the help of my pics and their captions would be this one and this one . Both super degrading. Both super, super fun.

- As for tasks from other people, the bully dares I received from Sexy_Sandra and Lop747 were two of the best I ever did from this site. Simple and achievable, yet with a little length and detail to them. Really naughty and humiliating, but also really enjoyable. Just a perfect mix. Oh, and they should also go toward answering your question about examples of roleplay, hehe!

Originally Posted by kila

Other than the leg shaving for the charity thing you've done, what else have you shaved/what is the most you have shaved off?

It was actually WAXING for the charity thing! Eek! The one and only time I've done that. Not because it was painful, but because it took literally about 3 months for my leg hair to grow back! haha.

That aside, I have shaved my legs on a handful of occasions - sometimes for my old Mistress, sometimes for dares and photo shoots (but not always... I didn't in my recent ones). I've also shaved my armpits and upper body lots of times, which I don't really mind. I sometimes just do that as a guy anyway when I fancy a change!

Not really shaved my pubes much... but then again, a lot of girls don't either! I always try to keep it neat. I mostly fear shaving it because, when I have in the past, this is the one where I'll ALWAYS get razor rash. Not a good look or enjoyable time! And very unflattering for lady looks. It also went wrong on my legs last time, which was a first. Think maybe on that occasion I forgot to use a fresh, super sharp blade! Oops.

To be honest, the shaving I probably avoid most is actually my face! In my day-to-day life as a man, I much prefer myself with a beard, so in recent years I've only really had a window to be fully feminine about once a year (usually around Halloween as I'll often shave for whatever costume I'm doing). Otherwise I tend only to shave if I get really, really committed to wanting to go "full lady" - like either for a photoshoot I just feel I *need* to do, or if I was ever to get opportunity for a public outing.

Originally Posted by kila

What is your favorite kind of hairstyle to wear when you crossdress?

The red wig shown in my photos is the one I use almost every time I dress up. It's a nice colour on my skin tone and a good fun style for looking a bit vintage and pin-up, which is clearly one of my favourite ways to dress, hehe. I also like the length, because even if it hasn't been stored properly, it only takes a few brushes and then it's ready to go again. It's very manageable!

I have a longer red wig that I'm keen to try and also a kind of purpley/pinky/grey "rainbow" wig, both of which I inherited from a female friend. They're good quality pieces, but I haven't made much use of them yet as I find the extra length difficult to brush out and get sitting right. I also feel like they cover more of me up and kind of take away from the fun and freedom of movement I can have with the shorter style. But we'll see - should probably try a change sometime!

If you were wondering about my real hair...

[whispers] I don't really have any

Originally Posted by kila

What do you enjoy to roleplay as? Have you done it in real life?

I consider most of what I do in my submissive mode role play. Whether it is the role of a slave and a sissy, or the role of real woman (like I am trying to emulate in my pin-up shots, or most times I am dressed for photos that aren't specifically related to sissy degradation).

As you can see above though, I also sometimes enjoy a little bit of an actual story, like with those highly arousing "bully" dares, where I played the part of a victim forced to submit to his tormentors.

Additionally, I have had a few photoshoot ideas and suggestions from friends that I've wanted to complete for a while, but not found opportunity. These include"

- "neatly dressed office girl comes home from work and turns into punk chick for the weekend"
- a playful cheerleader shoot
- a naughty school girl shoot
- a slutty secretary shoot

The first is more of a visual storytelling exercise, but those last three are roles I would gladly play in the presence of somebody dominating me as well

Oh and, bit of an obvious classic, but I've quite fancied getting myself a really nice quality maid outfit for a while, which would be great for photos, great for moments I decide to get kinky alone AND great for couple play if/when I hopefully next get involved with a dominant minded girlfriend or play partner



I hope that sufficiently answers your questions! I really enjoyed these ones, so if you want to know anything else, or simply to degrade me further in some way, please don't hesitate. Thank you so much, Miss!

<3

[Crossdress_Bitch]

Thank you for all the questions I have received so far. I have taken a lot of embarrassed and excited pleasure from answering them in such detail.

What’s the next thing getDare wants to know about me?

Maybe someone out there can really push me into territory that will make me squirm with humiliation?

Or maybe you’ll just ask me about pizza?

Hehe, let’s find out!

<3

[Guv'nor]

What was the best moment of your life? Why?

What do you want your last words to be?

Have you ever had a near death experience?

Do you ever go commando?

[Crossdress_Bitch]

Shorter answers this time as we discover that, outside of kink, I'm actually not all that interesting. Oops! Still, here we go...

Originally Posted by Guv'nor

What was the best moment of your life? Why?

I worry that my answer to this is going to sound rather depressing, but I really don't know! I've not had a bad life, but I honestly can't think of a moment that leaps to mind as the obvious best. Sorry!

I will, however, try to put a positive spin on it by saying that hopefully that means the best moments are yet to come!

Originally Posted by Guv'nor

What do you want your last words to be?

I think if I'm dying alone, but hopefully happy with my life, just something simple like "well, I enjoyed that," haha!

If I'm lucky enough to die with somebody by my side, be it a partner, a child or a friend, I would like to think my last moment would be spent looking at them and just saying "I love you", or simply "thank you."

Originally Posted by Guv'nor

Have you ever had a near death experience?

Again, I can't actually think of anything here to be honest, sorry! A few moments of stepping into the road without really looking properly maybe, but it's never been an actual dangerous situation. I feel so boring!

Originally Posted by Guv'nor

Do you ever go commando?

I have done! Sometimes if I have run out of clean laundry, other times if I've been dared or am feeling casual and it's just loose tracksuit bottoms I'm wearing or something. It's not too bad really, I don't mind it. Though as a fan of lingerie and looking feminine, I try not to go commando when in girl mode. What I've got down there's not really too ladylike

Thanks again for asking! Sorry I took so long to reply this time. Busy week!