An Open Letter to CD Cindy

Story Info
CD Cindy helps me grow into a cross-dressing sissy.
2.7k words
4.36
10.9k
10
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
eviltwin52
eviltwin52
1,710 Followers

My Dearest Cindy

I'm writing this letter to you to try to express my gratitude for your kindness in understanding me and your help during my growing pains. Before I met you I was a young man with a wife. As you know, soon after we wed, she and her lover taught me the art of sucking his cock. Not only the art, dear Cindy, but the responsibility of a small dicked male like me to pay homage to superior cocks. But I was lost in my own little world filled with doubt and fantasies. Your patience and experience guided me through the angst and turmoil so often encountered by newly minted sissies such as I.

And yes Cindy, you were so right. There is an art to cock sucking as you well know. You have assisted me in my time of need, helping me to finely tune my oral skills. But you didn't stop there. It was you Cindy who showed me that kneeling naked before a dominant male and taking him in my mouth needn't be a thoughtless task. "There's an art in pleasuring real men," you said. "Be content in knowing you have freely given of yourself the best and only way you can when the recipient of your cock sucking skills rewards you with his sperm."

You said that I could find peace when burying my face in his balls. "Lick that place behind his scrotum, johnnie. Let him think you're going to tongue fuck his anus." Girlfriend, you were so right. What used to be sighs of pleasure as Tom emptied his balls in me, instead, became grunts and groans that accompanied his almost violent thrusts. I knew I had truly satisfied his lust, thanks to you. As you said, my dear friend, "It's all in the technique."

I remember how ashamed I was to be put in panties by my wife and her lover. I cried when writing you, sharing details of that most humiliating moment when Tom first pulled the wispy thin garment up my newly shaved legs only to discover that my 5" erection. My little hard dick in panties was a source for their amusement. Oh, how they laughed at me as the front panel of my new panties became moist with my leaking pre-cum.

You took your time to comfort me as I wallowed in abject misery. It was you who pulled me out of my deep despair when you suggested I wear my panties with feminine pride. You told me that despite their laughter, my wife and her lover considered my cock sucking talents worthy and that I earned those panties. "Be thankful, johnnie. Wear those panties like a good sissy knowing that your spouse and her lover recognize something special in you and are willing to nurture it."

"They didn't force you into panties," you wrote. "You could have run away. You didn't. you stayed and let him panty you. It was you, johnnie who had demonstrated superior skills and talent to take a large cock into your throat. It was you who knelt naked, your hands behind your back, graciously allowing that real man to skull fuck you until he pumped his load into your gullet. "Deep within you, you wanted to have your wife and Tom put you in panties. You deserve to be in panties. It is now entirely up to you to show them you have what it takes to wear pretty panties."

You were right, Cindy. After reading your advice, I found that I was more than merely comfortable in panties. They were and are a symbol of my progress, my evolution. I have learned from you, dear girl that panties on a sissy are what real men expect. I went to my wife and her lover and thanked them sincerely for recognizing me for who and what I am. After I gratefully sucked him off, Tom was so proud of my acquiescence that he posted photos of me in various panties on my facebook account for all to see.

I was a bit concerned about people, you know, my family and friends seeing me in panties but I remembered you words of wisdom. "Sissies should quickly shed themselves of pride and dignity." Cindy, once I accomplished that, and it was no easy feat, I realized you were again right. What good is pride to a sissy when that sissy is prepared to open her mouth to any real man who needs a place to relieve himself of his sexual tension?

"There is no shame in a job well done," you wrote me. "Cherish those times when you are called upon to clean cum from your wife's pussy or breasts. Treasure those memories. You are doing for your wife that which her lover will not do. Always remember johnnie, real men do not eat cum. And by no means are you considered a real man; not by your wife or her lover and nor should you ever consider yourself a real man."

"Use their verbal abuse to your advantage, johnnie, you wrote. "Don't just accept the humiliations, find excitement and joy in them. Be sexually aroused in your humiliations. Pleasure yourself in them. Humiliation and subjugation are mental stimuli for cock suckers who know their place, johnnie. When slurping his cum from your wife or his cock, ask permission to masturbate."

"Let them see you jack your little dick, " you wrote me, Cindy. "Make eye contact and try to maintain that contact until your orgasm washes over you. Forget your silly pride. There is almost no degradation that a sissy cannot relish."

You explained it so clearly, Cindy, that self-gratification is my future. You wrote that knowing and accepting that I am unworthy of pussy is a blessing. "Too many little dicked bois waste their time trying to be men," you said. You told me that I was special. I was part of a small percentage of bois who understood that their purpose in life is to be of service to those real men who have need of my talented mouth. "Service to others is reward enough," you patiently explained. "The occasional permission to masturbate for their entertainment and amusement is icing on the cake."

Once again you were spot-on correct. Their constant denial of my pleasure intensifies my orgasms, Cindy. What used to be a nice feeling when my weak sperm trickled from my dick has become fulfilling experience. So powerful are my orgasms now, after months of waiting for permission to cum, that I actually squeal and squeak when climaxing. So loud am I that I almost, but not quite, drown out their laughter. I have learned to turn the torment their ridicule once caused me into something positive. I smile at myself when I think about how I must appear to them as I hump and fuck my dainty hand while squealing like a girl.

I confess that one time I was so loud that Tom stuffed his underwear in my mouth to stifle the noise.

It was you Cindy who suggested I expand my horizons. It was you, my precious girlfriend, who urged me to grow my hair shoulder length, experiment with make-up. "Choose your lipstick wisely," you wrote. "No greater lure is there to attract large cocks. Pretty lips on a boi are magnetic. The world is filled with real men who have nice big cocks swinging between their legs. Go out and pleasure those cocks, johnnie. Give yourself to those real men who desire to dominate you, make you their sissy, and use you for their own sexual gratification."

Cindy, you were right. I followed your suggestions and have attracted many men and have enjoyed ingesting their seed. I tried several colors in my quest to "choose wisely" as you said I should. I finally settled on Frosted Bronze by "Runway Rogue". Like flies to honey, Cindy, I have my choice of cocks. White (pink really), black, brown, and Asian cocks, all have been landed between my succulent lips. But how, I ask you, can I tell the difference in color when I'm sucking cocks with my eyes closed?

"Seek out aggressive men," you wrote me. "Aggressive men know how to tame a faggot cock sucker such as you." My wife's lover, Tom, is not aggressive. Although I did enjoy his verbal assaults, taking your advice, I seek out those who are more aggressive. Cindy, my darling angel, once again your wisdom and experience led me down the path of fulfillment. I relish those times when a real man insists on using my long hair as a handle to guide me through the blow job I'm giving him. It is thrilling to me when he takes a fist-full of my hair and forces his cock dep in my throat. I kneel there submissively thinking of you and quietly thanking you for your sage advice as he fucks my face.

Many times I have been thrilled to be chosen, taken really, when a real man, without words or my consent, has forcibly taken me by my wrist and led me to the nightclub's men's room. Sitting me on the commode, they have opened their trousers and fed me their manly cocks not even bothering to close the stall door.

Their masculinity on full display and without complaint from me, Cindy, I have sat there as they slapped my face with their cocks. I have seen the enjoyment those men have watching me try to capture their cocks in my mouth as they rub them all over my up-turned face. No greater compliment can a cock sucker receive then to see a line queue up behind the man who was the first to make me his.

I remember so well the email I received from you when you said that panties and make-up are not enough. You said it was time for me to spread my wings and be all I could be. Even though I was frightened to take the next step you did not give up on me.

My heart skipped a beat when I opened the package you sent me. You knew my size and yet, the mini-skirt you sent me was too small for my generous bottom. You knew that didn't you, you wonderfully nasty bitch? Half of my red panty clad bottom showed below the hem of that denim skirt Cindy. Just like you planned, I'm certain.

My cross-dressing was too much for my wife and Tom. When they called me vile names and unceremoniously pushed me out of the home I'd provided for them, you comforted me. "There's a whole world waiting for you johnnie," you wrote. "When one door closes, many others will open for you. Go out explore. Give yourself to those who understand what you are and know how to treat a sissy faggot such as you."

"Don't be afraid to give up that sexy bottom of yours either," you encouraged me in your email. "Go bravely into that new world johnnie. Go bravely and proud."

Cindy, my sweet wonderful girlfriend, I went bravely into that new world. I brought you with me too. I imagined you watching the first time a real man pulled me out of the bar we were in and had me rent a motel room for us.

I could almost hear your voice directing me to get on my knees and remove his trousers for him. "Smile sweetly," you said. "Look up at him when you take his cock in your mouth and fluff him until he's fully erect."

You were there when he pushed me onto the bed face down. I saw your look of achievement when he raised my skirt, pulled my panties to the side, and stuck his manly cock in my boi pussy from behind.

I imagined you being there, assuring me that the pain would ease, then turn to pleasure. I was comforted by your sweet smile as I grimaced and bit down on the pillow to stifle my screams of agony that first time my bottom was roughly plowed by that well-endowed stranger.

I could see you nodding approvingly when the pain subsided and I began to enjoy being made a woman.

I saw you clap your hands with joy as I humped my big bottom back at him and begged my new friend to fuck me harder. And Cindy, you were there as happy and satisfied as I was when he finished and used my hair to clean his cock.

How right you were when you said that I could expect no thanks of gratitude. My first gentleman left without saying a word. I watched him dress. Cindy, he never looked my way; not once. He just pulled on his pants and shirt, tied his shoes, grunted something unintelligible when he checked his wallet to see I hadn't stolen from him. Girl, he didn't even have the courtesy to close that motel room door when he left.

That opened door thing became a recurring theme. Every one of those real men who chose me, pulled me, either willingly or against my wishes, out of the gay bars I frequent to have me rent a room in some seedy hotel would simply fuck me and leave me lying there with the door still open. With their sperm seeping out of my bottom, many were the times when passersby would look in to see me still on my knees, my ass raised up, and a satisfied smile on my face.

You said I'd enjoy having cocks up my bottom. It's more than that Cindy. I've become an insatiable slut. If I had as many cocks sticking out of me as I have stuck in me, I'd look like a Chia Pet.

You inspired me to go out dressed in women's clothing. I did that. You told me to expect the unexpected which happens more frequently than you know. I did that too. I am very familiar with the sting of the leather belts some real men have used to tame me, to modify my behavior. Sometimes I pretend to fight them, to resist being fucked only to writhe in the glorious physical abuse that bends my will and fills me with passion.

I have, on many occasions, knelt with welts on my bottom and swallowed a cock in reverent thanks to the real man who took his time to show me the errors of my ways.

You would be so proud of me now, Cindy. As a submissive sissy slut, I love it when real men notice the hose I'm wearing under my extremely short skirts. I have perfected my "come hither" look I give those real men, and the lip enhancements I have treated myself to, well, let me just say that I am not a lonely boi.

Maybe I should have asked for your advice but I have begun hormone treatments which I get through the black market. One of my regular gentlemen callers suggested that I take those pills to shrink my already little dick and help me become more feminine.

There are advantages that come with hormonal treatments, Cindy. I have less bothersome hair on my groin, legs, arms, and chest to shave. My dick is a mere shadow of its former little self. My budding breasts are painful but I am happy to sacrifice my comfort so that others may find my body to their liking.

Your advice has helped me grow into my wonderful new persona. I am no longer the scared, doubtful cock sucker you first encountered in my emails to you. You helped me grow and nourished my desire to be more than what I had been. You've helped me bring out that cross-dressing slut you knew was hiding inside me.

Dearest Cindy. I know of only one way I could ever repay you for your indulgence and guidance. I am well aware of your predilection for dominant men but this submissive sissy wishes that when or if you and I ever meet in person, that you would allow me the honor of sliding my hands up under your skirt or dress, pulling your panties down and sucking that fabulous cock of yours until I finally blessed by the seed that comes from the balls of my wonderful cross-dressing girlfriend.

With love, hugs, and kisses, I remain faithfully your sister in life.

johnnie

eviltwin52
eviltwin52
1,710 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
petey377petey377over 2 years ago

hot hot hot love your stories!!!!!!!!!!!!!!!!!

eviltwin52eviltwin52about 3 years agoAuthor

My darling Cindy.

Like you girlfriend, I await those days when we can be together as a couple. I have learned so much about myself from you that it has become impossible for me not to follow your examples. Baby girl, I will strive to be what you want me to be always.

Love and kisses jennifer and I want those reading this that it was you, Cindy who honored me with my new name.

Jennifer

cdCindy1cdCindy1about 3 years ago

thank you so much for this story, Johnnie. It is wonderful.

I too hope that one day we can meet. It will be a wonderful hot sex session for the 2 of us. I can't wait.

Hugs & kisses,

cdCindy XOXOXOX

Share this Story

Similar Stories

"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
Roommate Dress-Up Straight guy is feminized by female beauty.in Transgender & Crossdressers
How Marissa Became a Woman Married CD experiences his fantasies with Wife's help.in Transgender & Crossdressers
Shemale Sister-in-Law Man gets massage from sister-in-law with shocking results.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
More Stories