Chronicles of Heather Maureen Ch. 04

Story Info
The life of one transvestite from start to present.
1.5k words
4.5
13.1k
6
0

Part 4 of the 13 part series

Updated 06/08/2023
Created 06/02/2016
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

An Evening with Marty

While I was changing to go to work Marty called mom again and asked if it was possible for me to along on a camping trip this weekend he had planned with his son. She agreed and he arranged a pick up time with her for tomorrow after school. He mentioned it to me as he drove me to work. I felt so different dressed back in my humdrum male things, without make up on and my nails bare. So plain and wallpapery. I hadn't even spent a full day as a female and felt saddened by the sense of loss. Marty cheered me up by telling me that ostentatiously I was going camping with him and his son so I'd have to be dressed femininely for the whole weekend. I broke out into a huge smile and wanted to hug him. He'd pick me up after work tonight and, if I wanted to, I could ride home dressed at least.

The night drug on and on and on. It felt like the clock was going backwards. I'd stuffed everything back into my backpack so, again, I managed to apply a foundation to my face, dress in lingerie' under my male things and generally prepare myself for a quick change. Marty was waiting for me when I finally managed to get out . Instead of stopping at a service station to change there I simply got into the back seat to change clothes and used the visor mirror to finish my face then slid across the seat to be closer to Marty. He smiled and put his arm around me then leaned down to kiss me deeply before slowly driving me home. I wished he was driving me to his place but knew I had to go home tonight and to school tomorrow.

Again I felt more alive and like things were right as I snuggled against him. He moved his arm from my shoulders, down to caress my inner thigh and I moaned softly as I spread my legs a bit for him. He drove aimlessly at first, or so I thought until he pulled into a park. Helping me out of the car he held my hand and we strolled along the road until we came to a path that led into the bushes and trees and finally to a small clearing. He kissed me again, several deep wondrous kisses and I barely noticed his fingers undoing my skirt and the buttons of my blouse. Soon I was standing there in just my lingerie' and heels, then I was kneeling there and staring at his cock as I stroked it. He smiled down at me and pressed my head forward. Eagerly I opened my lips and started to suck him, taking more and more of the shaft until I had all of it between my lips. My hands cupped and teased his balls and sac as I slid my lips up and down the shaft until he thrust forward and held it as he spurted deep down my throat and I did my best to swallow every drop. I licked him clean and used my fingers to wipe up what I'd missed, licking them clean.

Marty smiled widely as he picked up my skirt and blouse. Looking into my eyes deeply he told me to wait there till I'd counted to one hundred before I went back to the car. I started to reach out for my things and he smiled again and said no, you know I like to show my Sissy off. What better way then to leave you here in lingerie' and heels to make your way back. Both you and I know you'll enjoy it a lot. Now start counting. Shocked I stood there for a few seconds watching him turn and walk away, leaving me! Shaking, scared and nervous I started to count wondering how he could do this to me and why I was doing it? Was this some sort of a test? I felt so exposed and naked standing there and even more so when I'd finished counting and, hunched over, crouching down and using my arms and hands to cover myself started slinking my way back into the trees!

Feeling a bit more concealed there I still kept trying to cover myself but straightened up to make walking in the heels easier. I hadn't noticed how many forks there were in the path on the way in and blindly kept turning in the direction of the car. That may have been shorter but ahead I could see a campfire and soon after hear the laughter of several people. Oh Gawd! I turned back and took a different fork. It led thru the bushes along the road then went back towards the fire. Damn, damn, damn! Back again and the third fork curved to the right then out to the road. Was this where we came in? I was twisted around and confused. Looking carefully each way to make sure it was deserted I stepped onto the road and started along what I hoped was the way to his car. My heels clicked loudly against the pavement, each gasping breath echoed around me and my knees were wobbly as I walked slowly along. I'd have to pass the place where the fire was burning but if I stayed on the far side of the road I hoped they wouldn't notice me!

I was almost past it when one of them suddenly blurted out that he'd just seen a half naked woman walking down the road. I felt a shiver of excitement flash thru me before I pressed into the bushes and hid as he came down to look for me. His friends came down too and after looking each way asked him what he'd been smoking? I felt such a relief at not being caught I wanted to giggle but suppressed it as much as possible before that gave me away. I pushed out of the bushes and started back along the road, unconsciously starting back the way I'd come. I stopped and turned but felt drawn to parade past them again, maybe this time managing to let them all see me in my lingerie and heels! If I could have managed it without them grabbing me and discovering my secret I would have, but ohmigawd I wanted to so badly. I couldn't do it, I shouldn't do it, I, I, ohmigawd I was doing it!

This time I walked past the entrance slower and even stopped when one of them noticed me. Just for a second, the barest second till he had time to point me out to the others and they all stared at me standing there gloriously in just my panties, garter belt, nylons, heels and bra. Just long enough to feel my body spasm and shake before I rushed off along the road and ducked down the path to avoid their getting closer and grabbing me. I rushed along the path and past three forks, finding myself back in the clearing where I'd started out. I could hear them crashing thru the bushes along the road and starting down the various paths from it before they gave up. I could hear them telling each other how they'd be first when they found me and describing me and what I was wearing to each other, each differently then the others. I felt my body spasm again and again and while I didn't ejaculate I did realise I'd have to put on fresh panties whenever I managed to make it to Marty's car.

Marty found me there a couple of minutes later. He'd come looking in case something had happened and obviously something had from what he'd seen and heard on his way here. I didn't say a word just threw myself into his arms and kissed him deeply as I pressed myself as tight as possible against him. He seemed surprised but went with it. A few more kisses and I came up for air. He smiled when he ran his hand across the front of my panties and grinned when I undid his zipper and knelt again. I didn't eagerly suck his cock this time ... I devoured it whole. He lasted longer this time, not that he hadn't lasted awhile before, and I'd calmed down by the time he spurted down my throat.

"Thanks I needed that, gawd I needed that!"

"You're welcome Miss Heather. Told you you'd enjoy being here in just lingerie. Think how much more you'd have enjoyed it if you'd been wearing just your breastforms and not a stuffed bra like now. We'll have to do this again under those conditions."

He held my hand as we walked back to the car. Turns out I'd been going the wrong way. With him beside me I didn't care about being in just lingerie or worry about being seen. Unfortunately back at his car it was take the lingerie off, put my male things on, scrub off the make up and comb the body out of my hair so he could drive me to my place. He parked a short distance from my house in the driveway of an empty house and unzipped me then sucked me till I came, so I wouldn't be going home all 'worked up' and get mom wondering what I'd been doing.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

My First Time as Sara... Pt. 01 This is the story of how I became the girl Sara.in Transgender & Crossdressers
Becoming Joey Young man begins transformation.in Transgender & Crossdressers
Sissy Chantel, New Reality Ch. 01 Chantel finds sissy fantasy will become her sissy reality.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Snowed in with Aunt V Kelly gets snowed in with his sexy Aunt.in Transgender & Crossdressers
More Stories