Ron was opinionated about everything (humor and cross-dressing)

Dan was very opinionated about everything

Matt, a cross-dresser, tries to correct his friends about misconceptions about cross-dressing

Author's Note:
This story is the property of the author. It can be downloaded
for personal reading pleasure or sending to a friend, but if
you wish to re-post them at your site; please contact the
author for permission.
You may contact me at [email protected] if you like.
All flames will be ignored.

Another Fiction by
Cindy Will
Copyright 2017 Cindy Will All Right Reserved

Please show your support for by donating to keep stories
like this possible. This story is shared with and its readership.
I do not claim to be a grammar expert, in this story, you will find some grammatical errors in this story. The errors can be switching tense, spelling, or typographic errors. I ask if you find an error, please let me know by email, to allow me to correct and make the story enjoyable for others.
This is a story of fiction based on facts researched from the Internet.
This text file contains sexually explicit material. If you do not wish to read this literature, or you are under age Eighteen, PLEASE DELETE THIS FILE NOW!

[email protected]

Ron was opinionated about everything; despite any amount of facts, he would never admit he was wrong. Ron, Bob, Rich and I (Matt) were at a sports bar on a Friday night. I was not sure who mentioned the subject of cross-dressing, but Ron said, “All fucking cock sucking cross-dresser are fags, queers.

Bob and Rich laughed at what Ron said, with Bob saying, “Yeah, but they have tits. Chicks with dicks. Yahoo.”

Rich chimed in, “Yeah, a crossdresser is a guy who likes to eat, drink, and be Mary.”

Bob smiled and added, “What’s the biggest crime committed by cross-dressers?” Pausing for effect. “Male fraud.”

What was being said made me mad. These guys were my friends, but they were wrong about cross-dressing. I should know, I am a crossdresser. Today, cross-dressing is taboo, an activity that people joke about. I am not sure how to react to the stupidity of my friends. I could just sit here and pretend to laugh or get up and walk out.

Ron added, “A man told his shrink, “Doc, I had the worst dream of my life last night. I dreamed I was with twelve of the most beautiful chorus girls in the world, blondes, brunettes, redheads. All dancing in a row…” His psychiatrist interrupted, “Hold it, Andy. That doesn’t sound so terrible.” “Oh yeah?” replied Andy, “In the dream, I was the third girl from the end!” Everyone was laughing.

Rich told this joke, “Child asks his Mom, Mom, can I ask you something?" "Sure! What about?" replied the mother. "Well, I'm already fourteen and. I think it's just proper that I should own one." "Own 'one' what?" the mother asked suspiciously. "Could you buy me a push-up bra?" The mother quietly replies, “No.” "But my nipples are already prominent, and it catches attention." The mother voice is defiant, "Nope." "I think it would be just proper at my age..." The mother raises her voice, "I said no way...!" "But all my friends wear.......!" The mother voice is thunderous, “Johnny! “How many times must I tell you that bars are for girls?"

Ron said, “I don’t believe that men should be allowed to parade around our society in female clothing. I know that all the men we see cross-dressing are gay. They should be charged and taken to court for doing so.”

I had enough of these crappy jokes. I could not keep quiet any longer I was going to tell Ron off. On second thought, maybe I can provide some facts about cross dressing to educated my friends.

I spoke up with authority, “Ron, I read those cross-dressing men are usually not gay, and most are married or in a 70% were in a heterosexual relationship. Less than 10% of cross-dressers consider themselves bisexual, or homosexual. The stereotype that cross-dressers are gay comes from the false assumption that femininity exists to serve masculinity. Let us assume the reason women wear dresses, makeup or heels are to gather the attention of men. Within this sexist sociological framework, people can believe any man who dresses as a woman is doing it to gain attention. Of course, this isn’t the truth at all.”

Ron, Bob, and Rich all stared at me with questioning looks on their faces, but no words came out of their mouths. My statement caught everyone off guard. No one said anything. I felt it was necessary to add, “It's true that on occasion women do dress up to impress a man. Most of the time women dress to look pretty for themselves, to feel better about themselves, not to impress one another. Cross-dressers are the same; they wear because it feels good to them and not necessarily to attract the attention of men.”

Ron swanks, “Good Matt looks who knows all about queer men dressing up in woman’s clothing.”

My temper was rising with the stupid words coming out of Matt’s mount. I had to reply and point out, “Ron, you would be amazed how many successful men are a closet cross-dresser. Coming out is hard to do in our society, because of all the common misconceptions the public has about men expressing their feminine side. There is perhaps in the US alone 5% of the adult male population have cross-dressed.”
Ron said, “We all know, Hover was in the closet so cross-dressers must be pretty fucked up to want to be a woman.”

Someone must put Ron in his place, and I could not hold my tongue. Again, I had to correct Ron’s misunderstanding, “There are those who dress for erotic reasons, those that like the feel of female clothing, and those who wish to go out dressed as a woman just like one of the girls. In almost all cases they are not usually gay and do not prefer men as sexual partners. They are normal men when they are not dressing up, and they do not want to be a woman full-time. Dressing up is purely an expression of their feminine sides. Most cross-dressers are ordinary men who discovered a feminine aspect of their personalities. They need to transcend the narrow stereotypes mandated by conventional society”.

Ron would not stay quiet and blurted, “Ordinary men expression of their feminine side my ass. I heard that cross-dressers have an illness and cross-dressing can be cured.”

I know that what Matt said was a misunderstanding people have about men that cross-dress. I had to tell Ron the truth about cross-dressing and responded, “Ron, cross-dressing is not an illness and since it is not an illness why would there be a cure. No treatment is necessary as cross-dressing not considered an illness”.

Ron commented, “Well you never catch me in a dress.”

What a comeback Ron I thought. I was furious, and I looked at Ron in the eyes saying, “Cross-dressers come from all walks of life, races, creeds, and economic backgrounds. The cross-dressing dates back many thousands of years. In some cultures, especially some Native American tribes, they were highly respected as shamans. Most cross-dressers are well educated and come from traditional family backgrounds. The clear majority are heterosexual, and most are or have been, married. Most are happy in their masculinity, and only a small percentage opts to live as women full-time.” I was pleased with my response and standing up to Ron.

Ron said, “If a man cross-dresses and the wife catches him it is grounds for a divorce.”

I was on a role and corrected Ron again, “Cross-dressing is rarely a cause for divorce. A couple can compromise by granting time for the activity. In most cases, cross-dressers stay married. Most differences can be worked out to the satisfaction of the couple.” I should know because when my wife found out that I cross-dress, she wanted to understand why I would do such a thing. It took a while, but she knew and accepted my cross-dressing fetish.

Ron could not take the facts I was providing a had to say, “Cross-dresser are perverts. Who in their right mind would want to cut off their dicks to look like a woman?”

I had all the facts because if the research I did to figure out why I enjoy cross-dressing. I also had facts about cross-dressing when my wife and I sat down and worked out her accepting me being a crossdresser. Again, I could not remain quiet and said, “Ron, come on now. A clear majority of cross-dressers do not identify themselves as transsexual or identifying with being born into the wrong body. For most cross-dressers, their feminine feelings and expressions are limited to wearing clothing, makeup, and wigs.” I was doing well and continued, “Unfortunately the society we live in comments very limited roles for both males and females. When it comes to dressing codes, men are much more limited. Some guys grow up resenting this, much the same way that some girls grow up resenting wearing dresses and choose never to wear them. A lot of times, people, just like many women, are exhausted by their prescribed role in society. They just want to find some “balance” by expressing something different from masculinity.

Ron said, “I just do not understand why a man would start cross-dressing.” Ron must have been tiring in this conservation or was honestly open to my comments.

“Ron,” I respond, “Cross-dressers usually start dressing up as a child or in their teens. In very few cases it can start later in life.”

Ok, Matt” Ron rebutted, “You are so smart, why do boys start to cross-dress. If I caught my son cross-dressing, I would spank him”.

Right Ron,” I responded, “Probably out of a sense of childlike curiosity. Some cross-dressers may have sisters or a babysitter who may have dressed them up as girls either for fun or punishment. With some cross-dressers, the dressing is purely a fantasy. Dressing can relieve the stress involved in living up to the perceived male role model as a terrible, problem solver. Pretending to be a girl may provide him with a release from male peer pressures. Many times, cross-dressers will start dressing up in lingerie or silky clothing, like panty hose or stockings purely for the feeling of the fabrics on their body. Cross-dressing often will progress as time goes by to include complete dressing up, applying makeup and wigs, even mimicking female walking and talking.

Ron questioned, “Matt are you telling me that a boy can start to cross-dress, quit for 40 years then starts to cross-dress again?”

By now I had a few beers and realized I was running off at the mouth. I was disturbed what Ron was saying he was spouting off at the mouth and did not have any of the facts, just heresy, I stated, “When a man reaches the mid-twenties or later, social and economic pressures start to surface. Children, a mortgage, car payments, and education worries can play a role. Undoubtedly, the biggest cause of a man’s stress is through his job. The pressures of family life and the reduction of sexual activity as his marriage matures can contribute to his cross-dressing. Life stresses can build up, causing the dark memories of his cross-dressing past to resurface. He will start to cross-dress again to relieve his stress and the daily pressures.”

Ron said, “His wife, family or boss should tell him to quit.”

I know what Ron was saying was wrong, I know I had tried to stop but found that I was depressed when I tried to quite cross-dressing and was the happiest when I was dressed. I responded, “This is probably the worst thing anyone can do. Forcing them to stop and purging their feminine side could have disastrous outcomes. Most likely he would binge later as the cross--dressing urge would be even stronger. Besides, the pressure will still be there and could lead to violent breakouts or emotional distress. There is no “cure” for cross-dressing, and most crossdressers do not want one!”

Ron was still not listening, and he responded, “Well if my son or someone I knew were a cross-dresser I would force them to stop.”
At this point, I had to state, “Because of possible stress from families, jobs, and friends, many cross-dressers fetish is shrouded in secrecy. Burdened by fear and guilt, some cross-dressers deny their feminine side and purge of their clothing. Cross-dressers are further stressed by eliminating a significant part of their personality. Eventually, they return to feminine self-expression as a means of decrease of their stress. Some seek therapy, but as many therapists are not knowledgeable about cross-gender issues, they sometimes find themselves educating the therapist rather than getting the help they seek. Nor are psychiatric drugs of benefit.”

I wanted to go on, but Ron and Bob needed to go. I had my limit of beer and needed to sober up before driving home. Rich and I started to drink coffee. Bob was the designated driver for Ron, so they left.

Rich and I were now alone at the bar. The conservation was down to just Rich and I, Rich asked, “Matt where did you learn all that information about cross-dresser? You sounded so knowledgeable on the subject.”

I smiled at Rich saying, “Rich my friend, can you keep a secret?” Rich nodded his head. “Rich, I am a closet CD. I have been crossdressing since I was twelve years old. I stole my cousin’s panties and started to enjoy the thrill of under-dressing. The feeling I received from feeling the women's clothing was heightened by the feeling I get from the possibility of getting caught.”

Rich asks, “Matt what about your wife Sara, does she know?”

I told Rich, “Yes she knows but not as encouraging as I would like. She does not let me wear her clothing but will buy me a few outfits to wear. I underdress and have a collection of women’s panties I wear. Some are what are called sissy panties; they are full cut, made of silk, or satin and have lace and bows. I wear them around the house when Sara pretends to make me her sissy.”

By the look on Rich’s face showed surprise at what I was saying, “Damn Matt, you have me horny. Sara buys you clothes to wear then plays dress up?”

I have not shared my secret with anyone. I was feeling relieved talking to Rich and was feeling boastful and said, “Rich, my sex life has been incredible once Sara fully embraced my feminine side. When we have sex, it is more passionate than when I am not dressed. Making love to her is like we were two women, two lesbians having sex.”

Rich was leaning towards me listening to my every word. He said, “Matt, your lucky dog. So how did all this happen?”
I briefly told Rich how and why I started to cross-dress, “Started when I was twelve and needing something to jack off with. I stole panties from my cousin and jacked off with them. I stole panties and bra but had to put them to hide them. I rode my back home underdress and was so excited by feeling the material next to my body I shot off in my pants. I had a wet spot on my shorts and almost got caught by my best friend.”
I continued, “I almost got caught by my neighbor and when I went to the emergency room. I know they knew I would dress in panties and bra because they gave me more things to play dress up. I met a lovely lady at the Mall in the department store who gave me a corset, stockings and a wig.”

Rich asked, “Did you have sex with them?”

I understood Rich’s question was a misconception about a cross-dresser, “Rich, the only sex I had was with myself. My cross-dressing has been just for me, and I need to release my sexual tension. You know when you are a teenager you would try to find out how many times you can jack off, or wanted to see how far you can shoot your load. I did not think of sex with others, never entered my mind then.”
Rich was on his second cup of coffee, was wide eyed and had so many questions to ask, “So no one found out? Did your parents know?” He hesitates then asks, “Have you ever been with a man?”

These questions, I was wondering if telling Rich was a good idea, “Rich, my life as a cross-dresser has been a secret. No one I know knows and I hope suspects. My mother knew about the panties, but she never found the other I items I was given. At least she never said anything. I never asked, she never told. As for being with a man, when I was in college I became curious. I had some wild times. I had this term paper that I had to do research. The only way to complete the study was to dress up and pretend to be a woman. I have sucked a few cocks and been fucked too.”

Rich responded to my last statement, “No way. You mean you are gay.”

I responded by saying, “No Rich, I do not want to marry a man. I just like sex, and it does not matter if I am with a man or a woman. I am Bisexual.”

Rich paused a moment then asked, “Do you have any photos of you when you are dressed?”
I love posing for pictures and posting them to my Flickr site for others to enjoy. I gave Rich a link which he used to bring up my photos on his smart phone.

For the next five minutes, he stared at his phone, using his thumb to scroll between pictures. Finally, Rich said, “Damn Matt, your pictures made me horny. I would never have a guy suck me off, but I think I could if it was a cross-dresser. Do you any cross-dressing friends that I can meet?” “By the way, what is your cross-dressing name?”

I am responding with just one word, “Cindy.”

I was not sure where this conversation was going with Rich and if I wanted to tell him everything about Cindy. I had too many beers and was saying things that I have kept private all my life. I was talking about my secret fetish of dressing with a coworker who might not be someone I could trust. This colleague knows my wife, where I worked and now that I was a cross-dresser.

To be continued

If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
29 users have voted.

And please, remember to comment, too! Thanks. 
This story is 3152 words long.