Secret desire to Cross Dress

[AZeroticist]

I am an older male, married with kids. I have a happy life, but.......

My wife is very conservative and not into exploring any more. I have had several opportunities to be with another male and indulged.

I have been a bottom and have quietly desired to dress up as a woman and go out (I played Janet in Rocky Horror years ago)

To dress in a way that another guy wanted me would be the ultimate thrill...but I have fears and no idea how to start.

 

[Fifiboy]

Ohhh to be a gurl for a real man and be turned into a woman !! So hot !!

 

[AZeroticist]

The idea of him coming up behind me, while I wear a tight satin dress.....nibbling my neck and running his hands over the front
His hands wandering down to the bottom and then sliding his hands up again, up my silky stockings.....then as I part my legs, he flicks a thumb under the panties and then understands what his actions did to me

 

[AZeroticist]

I apologize if I offended you by overstepping....I was day dreaming my fantasy and it came out in words without thinking

 

[Iwishiwas69]

I apologize if I offended you by overstepping....I was day dreaming my fantasy and it came out in words without thinking

How is that offensive, it is a lovely fantasy. One that many 'guys' who want to 'cross' over into the crossdress scene would identify with. In one of my early days and inadvertently I might add, I danced with a woman who turned out to be a non-woman (lol) it was a close dance, very public dance floor, and for some reason I prematurely ejaculated into my own underpants. I was pretty young at the time (about 18) quite naive and never met a crossdresser ( I didn't even know the term then) but that has stuck with me , forever. I confess I have never done that a with a woman woman. Cheer up, your story is lovely.

 

[AZeroticist]

I appreciate your kind words.
One question I had was on shaving. I shave down below like my wife, but the stubble is rough when it comes back. I have thought about Nair Hair remover as it says it provides a longer time without regrowth.

Shaving is something I share with my wife. She has also been happy to peg me with a strap on and doesn't feel strange about it (though it adds to my previous fantasy).

What are your thoughts and what do you when applying make up? How does your wife not know?

 

[Iwishiwas69]

I appreciate your kind words.
One question I had was on shaving. I shave down below like my wife, but the stubble is rough when it comes back. I have thought about Nair Hair remover as it says it provides a longer time without regrowth.

Shaving is something I share with my wife. She has also been happy to peg me with a strap on and doesn't feel strange about it (though it adds to my previous fantasy).

What are your thoughts and what do you when applying make up? How does your wife not know?

I have been divorced for years and haven't lived with a woman for several. I like women. I just like being fucked like one and I like giving and receiving head like a guy. My exes didn't really give good head, although one loved swallowing -rapidly, (I like to keep it a little bit and then swallow) Make-up? only if I have a in-home date and then minimal, usually a light shade lipstick and perfume only. I am not now or ever had a desire to be a drag queen. I just love the sensuality of women's clothing and the the feel of a guy groping my butt and feeling his cock getting harder and harder. Shaving? sometimes, depends on the guy who iam seeing and the fantasy he brings to the table. I like a guy with both pubic hair and stubble.

 

[leftwantingmore]

To dress in a way that another guy wanted me would be the ultimate thrill...but I have fears and no idea how to start.

There are always fears when crossdressing. Start with one piece at a time. Wearing hosiery or panties is a good place to start. Take your time. Go slowly, it's easy to second guess yourself. And by going slowly, you get to enjoy every step of your journey to the max. The uiltimte thrill for me was when I was told by a man that he would masturbate and cum thinking of me, crossdressed.
As for shaving, a cream hair removes leaves you smoother and does last longer. Hair removal is a personal decision. I try to stay smooth from the neck down. I really hate ingrown hairs on my legs. If you wear hosiery with any regularity and do not shave your legs, ingrown hairs will be an issue over time. Staying smooth is a lot of work. I have to give woman who do maintain that smoothness a lot of credit and respect.

 

[AZeroticist]

You have certainly given me a lot of solid advice and I appreciate that. I live in AZ so the heat makes wearing pantyhose difficult except for January or Feb.
I like the idea of getting panties, but I am not small in that department, so more likely to make it look like I am going commando, lol.
Whereabouts in the States are you?

 

[PollyGons]

There are always fears when crossdressing. Start with one piece at a time. Wearing hosiery or panties is a good place to start. Take your time. Go slowly, it's easy to second guess yourself. And by going slowly, you get to enjoy every step of your journey to the max. The uiltimte thrill for me was when I was told by a man that he would masturbate and cum thinking of me, crossdressed.
As for shaving, a cream hair removes leaves you smoother and does last longer. Hair removal is a personal decision. I try to stay smooth from the neck down. I really hate ingrown hairs on my legs. If you wear hosiery with any regularity and do not shave your legs, ingrown hairs will be an issue over time. Staying smooth is a lot of work. I have to give woman who do maintain that smoothness a lot of credit and respect.

Excellent advice.

 

[leftwantingmore]

You have certainly given me a lot of solid advice and I appreciate that. I live in AZ so the heat makes wearing pantyhose difficult except for January or Feb.
I like the idea of getting panties, but I am not small in that department, so more likely to make it look like I am going commando, lol.
Whereabouts in the States are you?

Check out my profile, I am in NH, 17 miles from the Atlantic Ocean.
Women's panties are enjoyable to play in but feel confining and restrictive wearing daily. Getting a larger size gives me more room up front but makes me have a baggy ass. Not a good look. I look for womens styles with a pouch for comfort. I am not huge but I do need space.
To bad about the heat, hosiery is a great starting point and very arousing for most men. Silk is the best!

 

[PollyGons]

Check out my profile, I am in NH, 17 miles from the Atlantic Ocean.
Women's panties are enjoyable to play in but feel confining and restrictive wearing daily. Getting a larger size gives me more room up front but makes me have a baggy ass. Not a good look. I look for womens styles with a pouch for comfort. I am not huge but I do need space.
To bad about the heat, hosiery is a great starting point and very arousing for most men. Silk is the best!

Yes to all of that. A size up is a good move. I find the cut is important too. A good wide (or stretchy) gusset makes a big difference. Full panties my favourite.

 

[leftwantingmore]

My problem is I have a small bottom. I find that Silk Ice panties for men from Temu fit my ass nicely, a comfortable pouch and no seams. Great price and colors. I wear crotchless silky pantyhose and they fit so nice over my pantyhose and generally stay in place. Maybe give them a try.

 

[PollyGons]

My problem is I have a small bottom. I find that Silk Ice panties for men from Temu fit my ass nicely, a comfortable pouch and no seams. Great price and colors. I wear crotchless silky pantyhose and they fit so nice over my pantyhose and generally stay in place. Maybe give them a try.

Sounds delicious. I’m just imagining how that might look.