My Desires to be a Woman

Reads: 241  | Likes: 0  | Shelves: 0  | Comments: 6

  • Facebook
  • Twitter
  • Reddit
  • Pinterest
  • Invite

Status: In Progress  |  Genre: Non-Fiction  |  House: Where Beautiful Love is Made

This is a personal essay about the author's search for understanding of his sexuality.




It all began early, in middle school probably.  I enjoyed being a kid growing up in Brooklyn, doing guy things.  I was a die-hard Yankees fan, I loved fishing and boating with my Dad.

But deep inside, somewhere I felt so soft, so absolutely warm and safe when I was thinking about women.  Was I normal?


And what IS normal anyway?


I wanted to hold a woman, not a girl. A mature woman.  I was maybe 14.  When I discovered women who loved other women and this was called lesbianism, I was appalled that this was forbidden!  Why?  Women kissed other women all the time in these times.  It was still the early 1960’s and Jackie Kennedy was our mournful, high-class widow.  She set styles by buying things and making trips to stores and events. European women kissed their counterparts all the time! What is going on?


I was a follower. I sat in the back seat of cars as my older friends drove around looking for girls to watch!  I ‘d fantasize about the all the women making love to other women behind the curtains and yellow-lit lamps in the windows of Brooklyn as we drove around.  I dare not share my fantasies with any of these guys, for they would laugh me out of existence or shun me as a faggot.  This was ironic because all I thought about were women’s breasts, vaginas, arms, and their thoughts.


Pure lace, almost any color, soft and well designed on a nice dark stocking, used with a garter and some warm lighting made my erections come to a nice state of hardness. Lingerie.

A woman kissing another woman’s neck then her breast.

Her soft panting as the other woman slowly touches her arm, then her breast.  Two fingers pinch and caress a stubble of skin, an aroused areola.  A nipple taut in the cool air of the night surrounded instantly by a warm, wet tongue. 


Two women who desire to meld into one, they intertwine their muscular, well-toned legs as one rubs her wetness on her lover’s thigh.  Loud moans, cries, yelps and finally a roar of endorphins flowing through their bodies as they coalesce into a magma of lovemaking and climax together.


It’s always been a vicarious experience for me.  As much as I’ve fantasized about being able to watch two women make love to one another, I’ve never come close to it.  So I live in my mind. I try not to let it ruin my day but sometimes my fantasy addiction does create chaos and scatter my other duties to shatter like glass hitting a cement floor.


 There are some women, in their mind's eye, so intensely serious about their vanity and their sexual appeal, but with only faux breasts and flaccid penises who walk down the avenues and streets, looking for validation and money for their decision to make this very difficult transition.  We call them transvestites or trannys and they get ridiculed for so many things.

  In Paris, once I was drunk on cognac, on my way home through Pigalle and I solicited a woman.  I knew. I had a special sense.  She was black as night and very muscular. Probably Algerian or West African.  She took my 40 Francs, we went up to her shared flat and she wanted to suck my hard cock but I wanted to caress her unbelievable breasts. When she realized how respectful I treated her, she demurred a bit and let me touch her anywhere. 

She was obviously aiming to be rid of her amazing hard cock someday I was sure.  I was as confused as I was before I walked in, but that was how my life was back then.

She let me fuck her from behind and I remember holding onto her arms and lovely breasts as I came in her.  I stroked her hardness too, but she refused to let herself go.  She loved it and wanted more but I left.  I left in a hurry, the shame rushing back into my consciousness, of doing this so close to my theatre and taking chances with my health in a foreign country.


Breasts signify Life to me.  Yes, the womb and vagina are essential to bringing human life into being, but for me, breasts represent nourishment and Life.


My mother had lovely large full breasts.  I m sure I was not sucking on them long, as she believed in nursing with

artificial means.  No matter.  In the course of puberty and life, I observed her nice body more than once.  My father was a lucky man and he probably knew this too.


Somewhere during puberty, I became fixated on wanting to see as many naked breasts as I could to categorize the millions of variants of shapes, sizes, and textures of the female breast.

That, of course, is quite normal for a young boy going through puberty, becoming aware of the opposite sex and her body parts.


But I wanted more, much more!  I wanted to feel two women hugging and kissing one another, showing love and affection without any guise of guilt, shame or fear of retribution.

 This indescribable desire to want to be a lesbian was intolerable and led to the explosion of my full-blown sex addiction to buying and collecting pornography.  But I only wanted pictures of women making love. Everything else was thrown away quickly.  Men’s erect cocks between breasts always titillated me of course but if there were two women in the shot, I kept that image longer.


As an adult in the safety of my own apartment, I would look at some images, fantasize about them, and dry hump my bed till I  came.  Sleep would ensue and sometimes I’d dream of being a woman with the body I just saw, holding another woman in my arms and kissing her all night long.  I’d dream of licking her pussy and smelling her luscious scent, massaging her clit with my tongue till she climaxed in my mouth. I soon realized that lesbians enjoyed sucking on toes, so I dreamt of that and anything else I could to identify with being a woman in love with women.


Some men love to dress up.  For me, fashion is a planet I will never visit!  I do love the feel of fabrics and the look of certain sexy lingerie on women of course, but I know nothing about fashion.  I was not going to put on lipstick, shave my legs and

Try to wear a bra. Not me.

Anyway if I did, I would look WORSE than Jack Lemmon did in

“Some Like it Hot!”


My mother took me to the movies when I was young.  We’d go in the middle of the day.  She took me to see “Some Like it Hot!”

I will NEVER forget that movie and own a DVD of it.  But I watch it to see Marilyn move and act as well as Jack, Tony and all of Billy Wilder’s greatest moves as a director.


Mother’s milk can be a loving statement or a caress when we are down and lost. My mother was a woman who appreciated great art, music, and theatre.  She would’ve loved for me to teach music, but I wanted to play it.

I ‘m sure many men got nurturing about music and art from their mom’s but for me, it was something very special.  The flow of the pen on paper, the mark of a pencil on a sketch, the tone of an actor on stage was explained to me early on.

My mom would stand with me at the Museum of Modern Art in midtown Manhattan and ask me what I saw in the Cezanne and Van Gogh paintings.  She told me how a painter created images with points of color in the impressionistic style. I had so many outlets for my creativity early on it was mind-blowing sometimes.  I always went back to my fantasies of wanting to be a woman who loved women. How strange!

“No tree’s look the same Lester!” she’d instruct me as I tried to draw trees from memory.  The uniqueness of nature, the shadings of faces, the texture of a photograph all meant something to her.  I wish she could’ve painted longer. She was so judgmental of her work.  Her breasts were always close to me, she loved me unconditionally as she did with her older daughter.  She was a loving woman who gave her children the nurturing she could give despite her terrible upbringing to a mother who was mentally ill and unable to deal with the world turmoil of the 1930’s in America.


When I discovered the intricacies of pleasuring a woman by cunnillingus, I was taken to scents and textures I’d never experienced. I enjoyed it so much and it got me harder when a woman came, I sometimes didn’t need another orgasm.  Strange!

Until I realized how to stimulate a woman with the tip of my crown and rub her G spot, was I fully in control of my sexual appetite.

But for me, sucking a woman to completion was everything. Feeling her tremble under my mouth as I fondled her lovely body, or kiss her thighs.Unfortunately, I was so ugly and not adept at dating that I ended up going to prostitutes for the better part of my first 4 years after High School. It was totally embarrassing and shaming.


Despite so many stupid things I did, I survived college and my first music job on the road, but just barely. In 1974 I met a man walking on the street, we passed and checked each other out. By then, I knew that men were more attracted to me than women and to get off, I enjoyed being pleasured by some men.


Michel was a svelte, olive-skinned guy who befriended me for a short while.  I was sure he was planning to transition to becoming a woman at some point because of his innate femininity.  He was the only man I enjoyed kissing because he reminded me of myself and his nature was very gentle and erotic.

Shortly after we stopped seeing one another, I saw “Rocky Horror Picture Show,” with Tim Curry who reminded me of Michel.  The overt gay affect that was becoming popular along with some acceptance of gay lifestyle in the early 80s turned me off, and then, of course, AIDS ruined the sexual revolution.


Why are straight men so attracted to lesbians and lesbian porn especially?  Are women more loving persons? Of course, they are but that cannot be the only reason!

Men, of course, want to put themselves in between the two women to fantasize and somehow fulfill all their sexual desires!

Probably true for many, but this guy just wanted to observe, fondle himself and observe more!

I came to respect the love two women wanted for them. It’s not a show, but for men who paid for it, it was only a show.

I never wanted to pay for it that way and feel good about that to this day.


The female form is so wondrous when a truly sensuous woman puts on the air of seduction or wants to attract any attention to herself, men are going to take notice. When two women who are into themselves only, are really sharing love and compassion for one another, men demand to want to watch. WTF!??

 We all know these as given actions and we do not question motivations.

My closing point is that there are some men like myself who can respect all women for the loving, nurturing nature and want to give them ALL they are due.  If they want solitude I want to leave them alone!  If they happen to desire attention as they play and coyly attract more women into their circle, then I want to observe and respect their privacy till they say no more.’


I believe it's up to each man to respect and appreciate all gay women in our society.  They may be our teachers, lawyers, doctors or even our fire people.

Remember there is only one planet Earth, and we are all in this together.


(c) Sappholust 2020








Submitted: January 16, 2020

© Copyright 2021 Sappholust. All rights reserved.

  • Facebook
  • Twitter
  • Reddit
  • Pinterest
  • Invite

Add Your Comments:



Thank you for this story. I have had similar feelings about being a woman since the first time I saw one naked, if only for a day. I think ot is a hidden desire/fantasy for many men that they would never reveal or let anyone know about.

Thu, January 16th, 2020 4:45am


Personally I do not have nor have never had any interest in being a woman, but having been introduced to giving women oral sex as a teenager, I've been consumed with satisfying women that way ever since. I have, many times thought about how women who love each other and make love to each other share a special experience, not just sexually but emotionally. And I've envied lesbians because they know what pleases a woman and tend to share it rather than exploit it. Men, including myself, I think intend to drive a woman to the peak of pleasure too quickly because we're greedy ourselves, in the search for physical pleasure and completion.
My interests and experiences could only be with women; I have no interest in the male form. Your story here is intriguing and honest; very well done.

Thu, January 16th, 2020 2:34pm



thanks for your take on my essay. This came out quite suddenly and honestly. I am new to BooksieSilk and
am still wondering how much traffic the site gets. Any thoughts?
I also wanted to use the essay to introduce myself to this group, this house and hope BooksieSilk continues on! But I do have doubts...
Specifically, if the owners of this site want to be making money, and it fails to do so, then the site just disappears.... I always keep copies of my material anyway.

Literotica is getting very selective to the point of censoring some material they deemed "current events"
relating to political or environmental references I made in a recent story which they did not allow.
I am in the process of removing all my material (26 stories) from that site.

Thu, January 16th, 2020 8:01am

Other Content by Sappholust

Book / General Erotica

Book / General Erotica

Book / General Erotica