I crave to be penetrated like a real woman

Hello Mrs. Loving,

I think your site is fantastic.  I love the way you help and encourage us sissies to embrace who we are and encourage us to realize what we desire.  Over the past few years, I have had an incredible opportunity to explore my sissy persona with “Mistress X” in SF. It has been an amazing exploration.
 
I started wearing panties regularly as a sophomore undergrad. At the time, my desire was mostly to be dressed in women’s lingerie – I thought they were sexy – and wear make-up (why should only women wear it?) and only had the occasional thought of what it would feel like to be fucked. But, I always imagined that the person fucking me was a woman wearing a strap-on.  Yet the more I started to dress, the more I became excited by the idea of being a female and turning him on – feeling his cock and making him cum.
 
It was only after moving to the bay area, I really began to explore my female identity, i.e. buying clothes, not just panties, getting makeovers, and going out en femme.  Still it was almost 5 years later when I started training with “Mistress X” that I began to entertain the thought of pleasing a real man. My past play with Mistesses had involved strap-on play but it was more about me acting out a role, but I never saw it is a prelude to me wanting a real cock. In the 5 years, since I first met Mistress X, I have gone from a boy who fantasized about gender play to a sissy slut who craves cock. By the time Mistress X had asked her sissies if instead of a strap-on, did we desire a real, hot, throbbing cock, she had gotten in my psyche so much that I had become sissy cock craving whore who only wanted to please her.  I needed cock in my mouth. I wanted to take a man’s cum down my throat. I desired to feel his cock as  it penetrates and plumbs the depths of my virgin sissy pussy.
 
Ultimately, I would love to find someone like you who understands how I feel as a sissy.  I become tremendously excited about the idea of being forced feminized.  As I live in the east bay, I hope to one day to have you help me bring out my true inner sissy.

When did you first feel like a sissy?  How old were you?
I was young when I first felt a desire to dress as a girl. When I was young, my parents often made me stay with my grandparents. My cousin lived there with my aunt. Instead of sleeping in my pajamas, I liked to sleep in her nightgown.  

What were the first sissy clothes you wore?
While I guess there was only one first time, there were many first that standout in my mind. The first clothes I wore were my cousin’s nightgown and panties.  When I was in upper school, I stayed home one day just so I could wear my mother’s clothes and make-up. My senior year, some guys on the cross country team opted to dress as cheerleaders for spirit day. It was mostly for fun, but I was secretly excited about dressing in female cheerleader attire. I was immensely excited to have a reason to wear panties in public. It wasn’t until I was at university that I bought my own panties – a 3 pack of Jockey for Her. I know one pair was red and the other 2 were striped.  I remember the first thing I did was shave my little clitty; when I put those panties on, I felt like a porn star.
 
What does it feel like to know you’re a sissy?
It is liberating but it wasn’t always like this. As a university student, nothing could have prepared me for what happened the first time I wore a bra in addition to my panties.  It was early spring but because I was wearing a bra, I opted to wear a sweater. I was a little warm but tremendously thankful I was wearing the sweater when the younger sister of a friend of mine from high school stopped to hug me. To this day, I am not sure if she felt the bra beneath my sweater.  Except for work, I regularly wear women’s clothes and even then I at least wear panties.  I love expressing my femininity in dress and deeds and love it when people appreciate me in my femme persona.

 What are your deepest sissy desires and needs?
I would love to meet and be with a woman who wants to take me on a ride of forced feminization. I would love to meet a woman who can embrace both the male and sissy in me.  On some level, I desire to be taken out and forced to demonstrate what a good cocksucking cumslut I have become. More than anything I wish I had breasts.

What are your sissy sexual fantasies and dreams?
I have many fantasies. I crave to be penetrated like a real woman. I desire to meet a woman who embraces the sissy in me. To meet a woman who continues to prepare me to be penetrated like a woman. She will teach me to relax and to enjoy being fucked for the first time by a real man. I imagine she will enjoy introducing me to a man. I imagine he will kiss and caress me, nibble on my ears, and lift my nightgown to expose my breasts for his mouth.  All along, I can feel his cock growing in my hands. In my ears, I hear her repeating, “you want his throbbing cock, deep inside of you, you want to feel him as he penetrates and fucks you.”  As I lay on my back, he spreads my legs, raises them up on his shoulders before penetrating my hole. His strokes are long and deep. Together, they will teach me that this will be the only way I am allowed to cum.
 
I also have thoughts of cuckoldry chastity. When I am in chastity, I feel most emasculated as if there were just a hole waiting and wanting to be fucked.  These thoughts grow  stronger as I get in touch with my inner sissy. My mouth will be available for his pleasure, to get him hard before they screw each other. When they finish, I imagine that he fucks my mouth as they both tell me, “taste that you little sissy, that is the closest you will ever get to pussy. I bet you wish you had a pussy like that. Taste that pussy. Suck my cock, you little sissy.”  Or maybe he penetrates me with his pussy soaked cock.   
 
I also like the idea of being fucked in both holes. On my back, with one leg and my other being held up by a guy as he fucks my sissy hole while another has his cock in my mouth.

Sissy,
Morgan

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