How I Learned to Stop Worrying and Love Crossdressing

[Wageslave]

I don't think I'll ever get to experience that.

Don't do yourself down, you're a sexy and good looking gal

 

[muycurioso]

hot story

My dressing began in earnest with my ex. One evening she asked if she could do my hair I it was shoulder length at the time) and put makeup on me. I saw no harm and let her do it. When she finished she looked at me with surprise and said I would make a pretty woman. The following weekend she asked if she could do it again but wanted me to also put on one of her dresses. again i agreed. I found the experience so arousing that it just took off from there and I have never looked back. I love to dress

looking back I dated I dated a woman who was divorced. We had a lot of fun together. She brought that subject up a few times. I should have said lets do it.

 

[muycurioso]

long stockings

like thigh high long are so hot and sexy. I currently don't x dress. That would prob be the last straw in my already shaky marriage. (hmmmm that gives me an idea), Anyway I messed up and put some white socks in with a purple/red shade of pants. Now I have some pink socks. They are like new, I am not tossing them. I have worn one pair. Baby steps I guess. I also always buy the absolute longest tube socks I can find (up to and maybe over knee) Not quite thigh high

 

[muycurioso]

internet and Lit are great outlets for fantasy

I hope I am not out of line with my own crossd-ressing story:
As the title of this thread states I love cross-dressing. It did not start at a young age for me, the seed wasn't planted until my late 30's. One night my ex wife and I were having sex in our living room. She stopped for a minute and said she would be right back, she then went upstairs and came back down with two pairs of pantyhose. I have never cross-dressed or even thought about it at that time in my life. She asked me to get undressed and put on a pair of the hose. I did as she asked and she put on the other pair. I do not know if she did this to embarrass me or if it turned her on. The sex was very exciting that night. We did not discuss it after that as we were not getting along and divorced shortly after. For me the experience was electric, I loved the feel of the panty hose it made me feel free, different and sexy. It wasn't until many years later when my present wife and I were on a cruise and we were getting dressed for dinner I asked her if I could wear a pair of her panty hose. She seemed rather shocked but said that I could, with that I wore them all night under my regular clothes. For me it was the start of my love of cross-dressing.
Unfortunately it has caused a lot of problems with my wife and I. I find cross-dressing so arousing I can't even explain how turned on I get. We have gone through years of arguing and purging and buying clothes over and over again. I wanted to have a four way with another couple where the husband also cross-dresses. At first she was willing but then backed out. Throughout the years she has helped me out with getting dressed and putting on polish on my nails and toes. At one time she even let me buy a wig and helped me with make up. Some where along the line the wig went out with of the many purges I went through. All I know is that the more I dress the more I want to suck a cock. I want to get together with a cross-dresser and experience getting dressed together and enjoying each others bodies in all ways possible. My wife right now has lost her desire for sex mostly due to age and physical problems. We have sex 2 to 3 times a month and most of the time it is very vanilla. She is not up for much in the bedroom. We have not had intercourse in about 12 years. I could easily have sex twice a week with no problem ( I am 70 so it takes a little longer to build up my testosterone levels), my wife could go a month or more with no sex at all.
I can understand my wife's problem with my desires as she did not marry a man to have him dress up as a woman and get turned on by it to the point that he wants to go suck cock. We did go to a counselor for a while and she brought up the cross dressing and he did not make a big deal about it and said it was just a fetish. She expected him to blast me for the dressing and when he did not she just shut down and lost interest in going to counseling.
I get a chance to dress up with her about once every month or so. I tell her how much I appreciate her letting me do this and I also tell her how it makes me feel. I tell her that I want to get together with someone who enjoys the dressing up as much as I do. She has reached a point where she says I should go find someone and do the things I want to do. She feels that her lack of sex drive is a failure on her part but she is not sure what she can do about it.
I have always been a take charge type person but when I am in the bedroom I want her to be in charge and that causes even more problems for her. When I dress up I get very submissive but I want to be submissive with another cross dresser not some macho type guy. I am not into humiliation or pain at all. I love looking at all the pictures on literotica and imagine sucking cock and licking ass holes. I don't know if I will ever get the chance but for now the internet is my outlet.

I like captioned pics the best.

 

[vizio]

looking back I dated I dated a woman who was divorced. We had a lot of fun together. She brought that subject up a few times. I should have said lets do it.

You should have the sex is very intense

 

[muycurioso]

we had a lot of fun

You should have the sex is very intense

I probably should have married her. Her and I were fine, there were other issues

 

[AddyB]

Yes, I purged my lingerie, but I never forgot the intense love for wearing it! My wife and I enjoyed a good sex life for many years, but I was missing my lingerie. About 10 years ago my diabetes screwed things up, I developed E.D! It sucked big time! My cock didn't work. I started taking testosterone. Shots first then a rub on formula. Then about a year ago I was really horny. They told me to take a larger dose and I was cranked up, but I still couldn't get hard. Well on the way to town one day I decided to tell my wife how horny I was and that I wanted to wear panties because it made me hot all those years ago! So we bought some panties and I would wear them every couple of days. Still couldn't get it up, but I've always had a pleasing way with my tongue. My wife appreciated that immensely! My wife and daughter went into town one day and asked if I needed anything? "Yeah, could you pick up a pink sports bra for me please?" She did. Then I bought panties from Adore me and her room. I bought a bustier from adam and eve. Heaven! Now I have stockings and garter belt, chemises, panties galore, (as a matter of fact I'm wearing my VS panties as I write this) and I have to say I absolutely love crossdressing! Next time I'll tell you about how my wife pegs me! Oh I loved to be screwed! It's fabulous!

 

[cuckoldbill]

Yes, I purged my lingerie, but I never forgot the intense love for wearing it! My wife and I enjoyed a good sex life for many years, but I was missing my lingerie. About 10 years ago my diabetes screwed things up, I developed E.D! It sucked big time! My cock didn't work. I started taking testosterone. Shots first then a rub on formula. Then about a year ago I was really horny. They told me to take a larger dose and I was cranked up, but I still couldn't get hard. Well on the way to town one day I decided to tell my wife how horny I was and that I wanted to wear panties because it made me hot all those years ago! So we bought some panties and I would wear them every couple of days. Still couldn't get it up, but I've always had a pleasing way with my tongue. My wife appreciated that immensely! My wife and daughter went into town one day and asked if I needed anything? "Yeah, could you pick up a pink sports bra for me please?" She did. Then I bought panties from Adore me and her room. I bought a bustier from adam and eve. Heaven! Now I have stockings and garter belt, chemises, panties galore, (as a matter of fact I'm wearing my VS panties as I write this) and I have to say I absolutely love crossdressing! Next time I'll tell you about how my wife pegs me! Oh I loved to be screwed! It's fabulous!

Great story. Looking forward to the next chapter

 

[BlackSatinKnight]

I’ve been through that cycle; buy something sexy, wear it, hook up, regret, purge, many times. I don’t get the opportunity to dress often but I still love it. Luckily for me I’m now teleworking with an empty house and I just slid into a plum colored thong and a pair of pantyhose. I still need to keep them covered under my street clothes because of video chats, but I love the feeling of wearing something smooth and sexy.

 

[meowjennie]

I hope I am not out of line with my own crossd-ressing story:
As the title of this thread states I love cross-dressing. It did not start at a young age for me, the seed wasn't planted until my late 30's. One night my ex wife and I were having sex in our living room. She stopped for a minute and said she would be right back, she then went upstairs and came back down with two pairs of pantyhose. I have never cross-dressed or even thought about it at that time in my life. She asked me to get undressed and put on a pair of the hose. I did as she asked and she put on the other pair. I do not know if she did this to embarrass me or if it turned her on. The sex was very exciting that night. We did not discuss it after that as we were not getting along and divorced shortly after. For me the experience was electric, I loved the feel of the panty hose it made me feel free, different and sexy. It wasn't until many years later when my present wife and I were on a cruise and we were getting dressed for dinner I asked her if I could wear a pair of her panty hose. She seemed rather shocked but said that I could, with that I wore them all night under my regular clothes. For me it was the start of my love of cross-dressing.
Unfortunately it has caused a lot of problems with my wife and I. I find cross-dressing so arousing I can't even explain how turned on I get. We have gone through years of arguing and purging and buying clothes over and over again. I wanted to have a four way with another couple where the husband also cross-dresses. At first she was willing but then backed out. Throughout the years she has helped me out with getting dressed and putting on polish on my nails and toes. At one time she even let me buy a wig and helped me with make up. Some where along the line the wig went out with of the many purges I went through. All I know is that the more I dress the more I want to suck a cock. I want to get together with a cross-dresser and experience getting dressed together and enjoying each others bodies in all ways possible. My wife right now has lost her desire for sex mostly due to age and physical problems. We have sex 2 to 3 times a month and most of the time it is very vanilla. She is not up for much in the bedroom. We have not had intercourse in about 12 years. I could easily have sex twice a week with no problem ( I am 70 so it takes a little longer to build up my testosterone levels), my wife could go a month or more with no sex at all.
I can understand my wife's problem with my desires as she did not marry a man to have him dress up as a woman and get turned on by it to the point that he wants to go suck cock. We did go to a counselor for a while and she brought up the cross dressing and he did not make a big deal about it and said it was just a fetish. She expected him to blast me for the dressing and when he did not she just shut down and lost interest in going to counseling.
I get a chance to dress up with her about once every month or so. I tell her how much I appreciate her letting me do this and I also tell her how it makes me feel. I tell her that I want to get together with someone who enjoys the dressing up as much as I do. She has reached a point where she says I should go find someone and do the things I want to do. She feels that her lack of sex drive is a failure on her part but she is not sure what she can do about it.
I have always been a take charge type person but when I am in the bedroom I want her to be in charge and that causes even more problems for her. When I dress up I get very submissive but I want to be submissive with another cross dresser not some macho type guy. I am not into humiliation or pain at all. I love looking at all the pictures on literotica and imagine sucking cock and licking ass holes. I don't know if I will ever get the chance but for now the internet is my outlet.

Thank you for sharing. I think it's great that you've been able to be open with your wife, even if she doesn't necessarily approve. Many crossdressers dress in secrecy and when caught, it's the deception that hurts the partner the most, not the actual crossdressing.

A gap in sex drive is fairly common in older couples, as is a reluctance for women to engage in a dominant role in sex, so you are definitely not alone in that regard.

I'll only add that people sometimes—especially when feeling frustrated and powerless—give permission but secretly hope that the permission is never taken. I'm certain you know your wife better than anyone and whether she actually meant it when she gave you permission to open up your marriage, and I trust that you'll properly weigh sating your curiosity against your wife's feelings.

Best of luck!

-Jen

 

[richgo50]

Enjoying crossdressing

Thank you for sharing. I think it's great that you've been able to be open with your wife, even if she doesn't necessarily approve. Many crossdressers dress in secrecy and when caught, it's the deception that hurts the partner the most, not the actual crossdressing.

A gap in sex drive is fairly common in older couples, as is a reluctance for women to engage in a dominant role in sex, so you are definitely not alone in that regard.

I'll only add that people sometimes—especially when feeling frustrated and powerless—give permission but secretly hope that the permission is never taken. I'm certain you know your wife better than anyone and whether she actually meant it when she gave you permission to open up your marriage, and I trust that you'll properly weigh sating your curiosity against your wife's feelings.

Best of luck!

-Jen

I think you are probably correct about her giving me permission. I know she feels real bad about her lack of sex drive and also being leery of trying anything out of the norm, whereas I am open to just about anything. If I ever did try to get together with another crossdresser, I would have a good honest discussion with her to make sure she can really handle it.
Thank you for your input on what I wrote.

 

[CrossdressingChat]

Love of crossdressing

I started cross dressing at around age ten. I was inexplicably drawn to a pair of my mother’s satin panties that I found in the folded laundry. I felt them and instinctively started to rub them on my penis. I came (dry) for the first time and being sheltered sexually it was an unexpected surprise, as was the second time when I produced a little cum. Soon, I was sneaking into my parent’s bedroom to wear more of her clothes. I often wore a satin half slip and a satin blouse she had, plus a long string of pearls. I would roll around on their big bed and it felt so sexy and good. I was almost caught once by my dad, but luckily he did not come in and left the house. That would have been very bad. I also found that I developed crushes on a few especially pretty boys and many, many girls. I cooled it for my high school years but as a reached adulthood I began to purchase Penthouse and Variations magazines and would quickly check them for cross dressing and bisexual stories. When I found them I would make my cock sore with jacking off while reading them again and again. As a young adult I started dating a girl and I began to share my magazines with her. I admitted to her which stories really turned me on and she said they turned her on too. We both admitted to being bisexual and we had nights of fun renting VCRs and porn tapes (remember that if you are old enough?). We would do role reversals where she would dress me in a corset and stockings and she would pretend to fuck me, grinding on me until she came. We would mutually masturbate and tell each other our bisexual fantasies. She was not the brightest bulb, however, and I, unfortunately, lost interest in her, especially when she started smoking, yech! I did not dress much for a number of years until I met my wife and married her. For a decade I secretly “borrowed” pieces of lingerie of hers for jack off sessions. She once threw away a pair of pantyhose in our bedroom garbage can that rarely got used and rarely was emptied. I repeatedly pulled those out, wore them, and put them back in. I also wore her satin nightgowns and slips but could not fit into most of her clothes. Unfortunately, she kept throwing away the pieces that I wore. We have a good sex life and one time I had her put on pantyhose, then tied her up and blindfolded her then put on pantyhose as well and fucked her good. This, as you can imagine, led to a discussion where I admitted to her that I was a crossdresser and bisexual. She didn’t mind, but did not want to see it. I am very unpassable and she just didn’t want to see or incorporate it in our lovemaking...she likes manly men, which I usually am. She has allowed me to purchase several pieces of lingerie for my alone time, thank goodness and a few times she has allowed me to do the tied and blindfold scenario. As with many men on here, I have become more and more interested in being a sissy bottom for a man. My fantasies and jack off sessions are almost exclusively gay cross dressing and gay fantasies now. Pretty women still excite me in two ways: I want them, and want to BE them.

 

[meowjennie]

I started cross dressing at around age ten. I was inexplicably drawn to a pair of my mother’s satin panties that I found in the folded laundry. I felt them and instinctively started to rub them on my penis. I came (dry) for the first time and being sheltered sexually it was an unexpected surprise, as was the second time when I produced a little cum. Soon, I was sneaking into my parent’s bedroom to wear more of her clothes. I often wore a satin half slip and a satin blouse she had, plus a long string of pearls. I would roll around on their big bed and it felt so sexy and good. I was almost caught once by my dad, but luckily he did not come in and left the house. That would have been very bad. I also found that I developed crushes on a few especially pretty boys and many, many girls. I cooled it for my high school years but as a reached adulthood I began to purchase Penthouse and Variations magazines and would quickly check them for cross dressing and bisexual stories. When I found them I would make my cock sore with jacking off while reading them again and again. As a young adult I started dating a girl and I began to share my magazines with her. I admitted to her which stories really turned me on and she said they turned her on too. We both admitted to being bisexual and we had nights of fun renting VCRs and porn tapes (remember that if you are old enough?). We would do role reversals where she would dress me in a corset and stockings and she would pretend to fuck me, grinding on me until she came. We would mutually masturbate and tell each other our bisexual fantasies. She was not the brightest bulb, however, and I, unfortunately, lost interest in her, especially when she started smoking, yech! I did not dress much for a number of years until I met my wife and married her. For a decade I secretly “borrowed” pieces of lingerie of hers for jack off sessions. She once threw away a pair of pantyhose in our bedroom garbage can that rarely got used and rarely was emptied. I repeatedly pulled those out, wore them, and put them back in. I also wore her satin nightgowns and slips but could not fit into most of her clothes. Unfortunately, she kept throwing away the pieces that I wore. We have a good sex life and one time I had her put on pantyhose, then tied her up and blindfolded her then put on pantyhose as well and fucked her good. This, as you can imagine, led to a discussion where I admitted to her that I was a crossdresser and bisexual. She didn’t mind, but did not want to see it. I am very unpassable and she just didn’t want to see or incorporate it in our lovemaking...she likes manly men, which I usually am. She has allowed me to purchase several pieces of lingerie for my alone time, thank goodness and a few times she has allowed me to do the tied and blindfold scenario. As with many men on here, I have become more and more interested in being a sissy bottom for a man. My fantasies and jack off sessions are almost exclusively gay cross dressing and gay fantasies now. Pretty women still excite me in two ways: I want them, and want to BE them.

Thanks for sharing. Fantasies and fetishes aren't a problem until they begin to affect "real life" in negative ways. But unsatisfied fantasies that are continuously reinforced through sexual release can, as I'm sure you can imagine, eventually reach a tipping point and lead to rash action.

If you are confident that your fantasies can remain fantasies indefinitely, then great. If you are even slightly concerned that this isn't the case, then I would urge you to consider speaking with your wife candidly.

Best of luck!

-Jen

 

[pussycatmeowth]

I had a boyfriend years ago, who loved to let me dress him. We'd spend ages getting him ready in lingerie and make up and as I'd clip his suspenders in or straighten the belt, I'd let the back of my hand brush against his cock, now and again, feeling him stiffen under my touch.

Eventually he'd be ready and I'd lead him to the bed, lie him down and climb over him into the 69 position and we'd suck each others cocks up and down. The build up was so intense the actual sex was usually over in seconds, he'd always come very hard and sensing my mouth filling while tasting his spunk on my tongue, would bring me to a huge climax, my big balls emptying a huge load into his willing mouth.

 

[vizio]

Half the fun of crossdressing is sharing pictures

 

[vizio]

One more

 

[NickyKidman]

Hi everyone, I have just joined this forum, and Jennie’s initial post really resonates with me. I have been questioning my gender and cross dressing all my life, and I am now in my late forties. It started when I was four or five years old, and I remember praying at night that I would wake up in the morning as a girl. I would sneak into my sister and mother’s rooms during my childhood and try on their underwear, dresses and shoes. I did get caught once, and was so badly told off that a real sense of shame was associated with my feelings.

I hid this all, and met a lovely woman, and got married and we have raised our wonderful children together. It all came out twenty years ago, when I asked if I could wear her stockings during love-making. She agreed and went on to buy me clothes and heels, and helped me do my make up.

But she started to see it as a threat to our marriage, and the last twenty years have been a rollercoaster of emotion, with the gender thing coming between us.

I currently have a lot of opportunity to dress as I work from home, and half the clothes in my wardrobe are female. I cannot describe how wonderful I feel when I put on a dress, tights and heels, and make myself up. I know this is not something that will ever go away, and I hope that my marriage can survive the tension it can cause.

Thank you all for reading this

 

[meowjennie]

Hi everyone, I have just joined this forum, and Jennie’s initial post really resonates with me. I have been questioning my gender and cross dressing all my life, and I am now in my late forties. It started when I was four or five years old, and I remember praying at night that I would wake up in the morning as a girl. I would sneak into my sister and mother’s rooms during my childhood and try on their underwear, dresses and shoes. I did get caught once, and was so badly told off that a real sense of shame was associated with my feelings.

I hid this all, and met a lovely woman, and got married and we have raised our wonderful children together. It all came out twenty years ago, when I asked if I could wear her stockings during love-making. She agreed and went on to buy me clothes and heels, and helped me do my make up.

But she started to see it as a threat to our marriage, and the last twenty years have been a rollercoaster of emotion, with the gender thing coming between us.

I currently have a lot of opportunity to dress as I work from home, and half the clothes in my wardrobe are female. I cannot describe how wonderful I feel when I put on a dress, tights and heels, and make myself up. I know this is not something that will ever go away, and I hope that my marriage can survive the tension it can cause.

Thank you all for reading this

Thanks for sharing. Tension from a female partner is basically expected in most cases, because crossdressing provokes insecurities that cause them to feel like their very womanhood is under attack. Specifically:

1) Negative stereotypes about crossdressing perpetuate the myth that all crossdressers are closeted gays or bisexual who want to transition to becoming female, which results in her feeling "deceived" about your sexuality, worried that you aren't or will stop being attracted to her sexually, or concerned that you want to transition. In reality, crossdressers come in all genders and sexualities.

2) Women with a binary view of gender may feel that you seek out femininity because she doesn't offer enough of it, i.e. "You're doing this because I'm not woman enough for you." Of course, it actually has nothing to do with them and is an internalized desire that began long before she even entered your life.

3) The overwhelming amount of "sissy"-oriented material on the internet may lead the uniformed to believe that all crossdressers are sissies who are into kink, BDSM, chastity, humiliation, group sex, etc. when in reality the vast majority of crossdressers are very vanilla and very heterosexual. Basically an all squares are rectangles but not all rectangles are squares situation.

Open communication is crucial to overcoming any challenge in a relationship, and I would encourage her to learn more about what crossdressing actually means instead of just going with what she's heard. My blog post on common crossdressing myths might be a good place to start.

I do hope that most female partners will come around and at least tolerate if not necessarily enjoy their partner engaging in crossdressing once they learn a bit more about it, but the unfortunate reality is that for some women, it is a dealbreaker no matter what. In those cases, it's time to consider if crossdressing is right for you.

Good luck!

-Jen

 

[pantomike]

Half the fun of crossdressing is sharing pictures

Wow looks great

 

[pantomike]

Half the fun of crossdressing is sharing pictures

Wow looks great

 

[CD_Bree]

Half the fun of crossdressing is sharing pictures

Omg love that key hole skirt. So cute

 

[CD_Bree]

I finally started to embrace dressing years ago! I haven't looked back. My wife has been great support to me. She helps with makeup and clothes tips. When we go out of town I take stuff with me. She got my ears pierced recently . Tyring to get passable so we can go shopping together! Here's a little pic!

 

[bimori]

I finally started to embrace dressing years ago! I haven't looked back. My wife has been great support to me. She helps with makeup and clothes tips. When we go out of town I take stuff with me. She got my ears pierced recently . Tyring to get passable so we can go shopping together! Here's a little pic!

You look so sexy in that outfit love.

 

[richgo50]

I finally started to embrace dressing years ago! I haven't looked back. My wife has been great support to me. She helps with makeup and clothes tips. When we go out of town I take stuff with me. She got my ears pierced recently . Tyring to get passable so we can go shopping together! Here's a little pic!

Good luck, I hope you get there. You are a lucky gurl.

 

[richgo50]

One more

You are simply beautiful. Luv your pictures.