The Desires Within

Story Info
Past experiences come back to life.
1.7k words
4.54
17.1k
12
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

This is a special piece for a fan of mine. Thank you for your feedback and I had a blast exploring this new type of work, you know who you are. Thank you.

*

Hello, my name is Neil Shepard, I'm a thirty year old accountant from Michigan and this is the story of weird (as some people believe) yet satisfying sexual journey. Even at the age of thirty, I'm still pretty good looking, I haven't gotten any bigger and try to get to the gym four times a week. My black hair doesn't have any grey going through it and I don't have wrinkles yet.

Anyway this story started when I was nineteen, I was still living at home to save money while going to school. My father left was always on business trips so I was the man of the house so to speak. Growing up I had only my mom and we were extremely close, I'd often spend my time before school sprawled out on my mom's bed while she got ready for work. She would sit at her vanity dressed in her red kimono dad had brought back for her and do her makeup while I watched. I didn't watch her dress or anything, just doing her makeup or her hair, she would prattle on about nothing in particular unaware I was mesmerized by the way she did her make up flawlessly yet effortlessly.

Sometimes when she was at work and it was just me I would sit at her vanity and try to apply makeup as she did, which never worked out. She caught me using her makeup when I was nineteen, when she walked into the room I was terrified she was going to kick me out of the house. Her reaction surprised me, she put her things down on the floor and walked over to me while she shook her head, "Oh dear, red is not your color sweetie. You should try a subtle pink. Let me show you." I smiled at her and moved over on the bench to make room and she showed me the basics.

After that day if dad was away on business I wasn't Neil, I was Natalya. Mom loved having a daughter and the best part was that when I was made up nobody could tell the difference. Mom often took me shopping or to the nail salon, I enjoyed our little outings but what was about to come was much better.

I was dressed in a pink blouse and lovely black pencil skirt the day that our sexual relationship began. She brought a friend home from work, his name was Mason. Mason was a fit and handsome black man, the moment he walked in the door I melted and felt my cock twitch in my silk panties. Mom smiled at my reaction and gave Mason a curt nod before leaving the room. I was shoved to the floor and in an instant a hard dick pressed against my lips, on instinct alone I opened my mouth to say something only to have my mouth filled.

Mason's large hand found their way to my hair, holding my head in place he began to thrust, fucking my mouth. At first I was unsure how to feel about what was happening but as I got used to the feeling I started to like it. It wasn't at all what I expected, it wasn't gross nor did it taste bad, it was a musky yet sexy taste that I can't accurately explain. I started thinking of blow jobs I had received and things that I liked so I started pressing my tongue to the bottom of his cock as it slid past my lips. Mason's groan was all the approval that I needed, I began bobbing my head to meet his thrusting hips and my hands came up to cup his heavy balls.

I hummed happily as I closed my eyes and enjoyed the new sensations washing over me. Keeping one hand on his balls I use the other to reach up my skirt and rub my hard on through my panties. I moaned loudly around the thick shaft in my mouth, Mason let out a roar and stopped moving. I was fearful that I had hurt him when I felt his cock twitch and hot salty liquid spilled down my throat.

That wasn't the last time I would be Mason's cum dump and as time went on I became his sissy. He took what he liked from me and I'm not ashamed to admit that I loved every second of it. When I moved out of my parents place I saw less and less of Mason until his visits ended all together.

While I was working at an out of town bank I met a temp named Lisa who is now my wife. After six years of marriage I have become bored with our sex life. Lisa and I don't have children or anything like that, I just find myself missing what I had discovered with Mason. My wife was nearly always home, as she got off work before me, so I couldn't even do my make up or dress up on occasion. I felt as if I was losing a part of myself.

I sighed and got out of my car as I pulled into my driveway, as I walked into the house a shock ran through my spine and my cock jumped to attention. I was standing face to face with Mason. He smiled but frowned as he looked me up and down, "Go get dressed sissy."

"Mason, how did you get in here?"

"Did I stutter sissy? Go. Get. Dressed. You know what I like, " I shivered at the command and took the stairs two at a time to my room. I quickly got out my makeup and pulled out Mason's favorite outfit, a mini skirt, sheer halter top with a colorful bra underneath, pantie hose and pair of spike heels. Walking in heels for the first time in years felt heady.

At the bottom of the stairs I paused at the sight of Mason standing gloriously nude in front of me. He hasn't changed despite the years; he is still beautifully sculpted and leanly muscled, "On your knees Natalya."

I quickly drop to my knees and wait for Mason to move in front of me and press the blunt head of his cock to my lips. As a tingle spreads down my spine I open my mouth and run my tongue over the head. A long hiss comes from Mason, closing my eyes, I open my mouth wide waiting for him to shove his cock down my throat.

As soon as his cock comes to rest on my tongue my mouth closes around his thick shaft and my tongue starts to rub back and forth along the bottom of the shaft. Mason's rough hands fist in my hair and he starts to thrust in and out of my mouth rapidly. At one point it hits the back of my throat and I swallow around it, allowing the thick cock to slip down my throat. He holds his cock so deep down my throat that his ball rest against my chin and I stick my tongue as far as I can to lick his nuts. Mason pulls his cock from my mouth and I cough and sputter causing a deep laugh from him.

Giving myself a break, I pump his cock with my hands and suck his balls into my mouth one at a time, "Okay Natalya, enough foreplay. Your cunt has to begging for cock." Reaching down Mason pulls me to my feet and pulls me flesh to his body. "I think your wife wants me to fuck your tight little cunt," he whispers.

Shocked at the mention of my wife, I turn and see her with her dress hitched up to her hips, her feet on the edge of the couch, her long legs spread and two fingers deep in her trimmed pussy. My gaze travels to her face and I see a dreamy look in her eyes, catching my eye she bites her lip and nods her head.

I look down at the coffee table in front of me and bend over, bracing myself on the table. Mason's slippery finger as my entrance and he pushes in. I gasp at the intrusion and the pain; it's been too long since I fingered my ass. Mason doesn't take long to prep me before the latex covered head of his cock presses against my ass, "Okay sweetheart, I want you to know I ain't going easy on you. I'm going fuck your little cunt like never before."

I shiver with anticipation, "Please fuck me." I don't need to ask twice. Just as the words leave my lips Mason thrusts his cock deep into my ass. I scream and one had flies to my erection, jerking it furiously, "Move please."

Mason grips my hips, "I want you to look at your wife while I fuck you. I want her to see what a little sissy you are."

I look up at her and see her cheeks heat as she rubs her clit, Mason starts to move, slowly at first, and then he begins to pound into me. My groans fill the air and mingle with the moans coming from my wife and the sound of his hips slamming into my ass. "Yes," Lisa breathes huskily. "Yes Mason, fuck his pussy. He's a dirty little sissy."

Lisa's words causing my eyes to roll back in my head as my hand strokes myself to orgasm. I moan loudly, my ass clamping down on Mason's big hard cock as I shoot my cum over the floor. "Oh fuck! That's it sissy, squeeze my cock. Oh fuck, I'm going to cum."

He pulls out of my ass, turning me around, shoving me to my knees and ripping the condom off before jerking his cock into my mouth. Behind me I hear my wife make herself cum and then I hear a loud roar just in time to open my mouth. I swirl his cum around my mouth and saviour the taste before I swallow his load, "Mhmm, good sissy. I'll see you next week."

I watch as Mason dresses and walks out the door before I turn to my wife, "How did you know?"

Lisa stands with a smile on her lips and motions for me to turn around. I spin and see my mother standing in the kitchen doorway, "That was hot Natalya."

"Thank you mommy," I smile.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
Little_panda2412Little_panda2412almost 6 years agoAuthor
Reviews

Hello, when I wrote this story originally I had planned it to be a one shot, however with you guys asking for more I have decided to give it to you and continue the story. It will be a little while before I do post the story but I hope you enjoy it.

AnonymousAnonymousover 6 years ago
Intriging

There is soo much more that is untold.

I have more yanking to do .

PLEASE --- more

AnonymousAnonymousover 6 years ago

I'm not usualy in to stories like this but this was hot! But where was the incest? That was the reason i actualy started reading the story. Is there a second chapter coming where the mom and wife get involved?

300bowler300300bowler300over 6 years ago
ONLY ONE WORD "HOT"

THIS IS A STORY THAT I HOPE THAT THERE IS MORE AND MORE TOO IT...! BETTY jo xoxo

Share this Story

Similar Stories

A Husband Named Cathy A husband's dream comes true. He becomes Cathy.in Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
Wife's Idea Wife teaches Hubby new tricks.in Group Sex
Wife Converts Husband Ch. 01 She finds out he's into kink.in Transgender & Crossdressers
Husband's Transformation Ch. 01 Husband caught wearing panties and changes begin.in Transgender & Crossdressers
More Stories