Chronicles of Heather Maureen Ch. 13

Story Info
The life and times of one transvestite through the years.
3.2k words
4.65
9.8k
6

Part 13 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

Friday Eva asked me how the doctor's appointment had gone. Fine I told her, aside from the idea that I'd have to choose between becoming more feminine overall or becoming more masculine. Apparently I had remained static for as long as I could.

Rick joined in and said he didn't think I'd ever truely be happy as a male, or I wouldn't have started dressing femininely in the first place. I did seem to enjoy being feminine. I smiled a lot more then I did when I'd been coming in as a male, I looked happier, listened to what I was told better and was a lot more pleasant to be around. Eva agreed with him.

Still it was my life and I was the one who had to decide how I was going to live it! It wasn't like I felt like I was a female trapped in a male's body. I just enjoyed being dressed femininely and being treated as a female most of the time.

For me it was relaxing to spend at least part of my time as a male. I didn't have to do my face, worry about my hair and nails, pitch my voice properly, fuss over what to wear. It wasn't anywhere near as exciting sexually and didn't have anything like the incredible thrills I got from exhibitionism while dressed and done up.

Was it merely because I was raised as a male? The fact that I had to think about it at all inclined me more towards staying male and trying to shed this obsession of dressing femininely. Would I be able to?

As all this ran thru my mind Rick made it clear that as long as I worked in the office I would still have to dress femininely for work. I smiled as I nodded yes while wondering why I did it so quickly and smiled so widely.

The part of my mind that controlled the feminine side of me had lurked more in the background for since I'd started dressing daily for the office. Now it came out of hiding and took control again! After work I ended up going to a drug store to get the prescriptions filled, whether I wanted to or not. The pharmacist gave me a strange look when he read them then asked me if I was transitioning. I nodded yes and smiled at him. He shook his head and soon I had the vials of pills in my hands.

I made it all the way to the front counter where I paid for the bottle of water I'd grabbed before I took the first pills. I felt my breasts tingle, my nipples crinkle tight and throb, my whole body shiver and come alive as the pills slid down my throat. I smiled and giggled and wrapped my arms around myself in a hug as the male side of my brain figuratively shook it's head at it's inability to stop my doing it.

At home I stared at my nude body in the full length mirror trying to find signs of increased femininity before I slipped into my bubble bath, both hoping and dreading that I'd see some. Were my nipples a bit fuller, a touch more sensitive? Was my butt a touch more rounded? No, taking one round of pills couldn't affect me more then physcologically, I knew that, yet I kept looking.

The only thing I knew for sure was I felt more excited and sexually charged then I had been in a long time. I'd become more conservative in the way I dressed since sort of settling down with George and dressing for the office after Rick and Eva had gotten back. My inner slut may have been tamed for awhile with being nearly constantly dressed, spending time with George and the phone line, even if only at home now, but now she was back!

I couldn't stop myself from dying my hair a brighter orangey red or styling it high and wild after. My eyes and lips stood out a lot more then what had become normal lately and my nails flashed more now that they were a very bright glossy red. Long dangling fake diamond earrings matched the choker around my neck and the bracelets on each wrist. Dressed in only a sheer light green babydoll nitie with sheer black stay ups under my coat and five inch come fuck me heels I drove to the nearest adult store.

I'd promised George I wouldn't go to the park, but this wasn't a park the slut side of my mind reasoned. Still I stared at the entrance for a few minutes, working up the fortitude to get out of my car.

Taking several deep breaths to try and calm myself down I finally opened the door and stood up. My legs were wobbly as I started across the street and went into the store. The calming didn't last long, if it happened at all. I was so extremely excited my body was trembling helplessly as I went inside.

I had to stand in the entrance for a minute or two before I could go any further; feeling my belly convulse, my nipples crinkle tighter and start to throb maddeningly, my body spasm lightly and my legs barely managing to keep me upright. The amused stare of the clerk made me blush as he watched me stand there helplessly trying to get myself together.

The click of my heels and the pounding of my heart were the only sounds I could hear as I slowly made my way further inside. I took more deep breaths as I seemingly surveyed the racks of movies and looked around. Yes there was the curtain leading to the peeps with the big sign telling you to buy tokens from the clerk; just as I remembered it from when I'd bought my first sex toys here.

My arrival had been noted as men were coming out of the peeps, spreading out around the store as they looked me over. Oh yes, yes this was what I needed and wanted the slut side of my brain shouted inside my head. Even with the added realism I added to the phone calls I took I never felt so fantastically excited as the thought of all their eyes seemingly seeing right thru my coat at this moment made me!

I smiled and stood up straighter, thrusting my breasts out as much as possible. Then my mind went completely blank as the sensations flooding my mind overwhelmed me so much that my body became more of an automaton. My male side stayed silent and hidden and the other side didn't care as long as it held these men's attention.

My hands were still shaking a bit as I bent down at the waist to look at a lower row of movies. I knew the back of my coat would rise high enough to uncover the tops of my stay ups, the smooth bare patch of thigh above them and the nicely rounded bottom half of my lower cheeks with my lacy French cut panties tugged high and tight enough to nestle between them.

Seeming not to notice any of the men watching me I swiveled and turned, rocking from one heel to the other then straightened up and moved down a few feet to do it again. One thing I knew for sure was that if I had been born female I would have had to be a stripper!

I bent at my knees to examine the bottom shelf. Heels together under my cheeks and knees spread wide. My coat may have covered the outside of my thighs from just above mid thigh up now but the insides and the bottom half of my sheer panties and crotch were fully exposed now. Again I turned from side to side to make sure they all got a good long look.

Standing up I smiled as I noticed several of the men trying to look innocent as they pretended to be looking thru the movies themselves.

I faced the rack to try and hide what I was doing as I unbuttoned my coat. I shivered and my belly undulated a few times as I felt it flare open while I walked over to where the toys were on display; holding a few up and turning to make it open wider while seemingly seeking better lighting to read the descriptions.

Setting the last one back on its hook I straightened up and put my hands on my hips to make sure my coat was wide open as I turned to look up and down the rows of toys, watching their reactions from the corners of my eyes in delighted fulfillment and tingling excitement.

Yes, yes, yes this was what I needed, what I wanted. I could feel every inch of my skin as their eyes roved over me. My nipples crinkled even tighter and started to throb. My pulse beat in my throat maddeningly. Yes, oh yes, this was what Heather Maureen had needed and wanted. An appreciative, willing audience to her exhibitionism!

The click of my heels was still the only sound in the place as I went to the counter and bought tokens. I made it halfway to that magic curtain before I turned back and asked the clerk to hold my coat for me. Sure he said. He took a good, long, look at my body, licking his lips. He fixated on the sheer front of my panties as I shrugged it off and handed it to him.

I hardly made it inside the back before being grabbed and pulled aside, groped untill I was moaning softly then told to kneel down to suck his cock! The quick spasm of my body told me how much I'd missed being sexually submissive as I knelt quickly.

I wrapped my lips around it eagerly, hungrily and so, so greedily. I tried to swallow it whole and managed half before my lips slid back to the tip and my tongue swirled around it! Yes this was the reason Heather Maureen existed; to show everyone what her body looked like in the frosting of lingerie' and to serve them sexually after! It felt like I had barely started to suck him before he exploded down my throat and I swallowed it avidly. He pulled it out as soon as he finished, did himself up and left the back quickly.

Several other men had been watching but none came forward to use me. I got to my feet and walked down the hallway, looking into the available private booths on either side, till I reached the small theater at the end. I sat in the middle of the front row and stretched my spread legs out.

Almost immediately someone sat on my left. I stared at the screen watching two TV's make out as his hand started to stroke my thigh above the stay up and over the front of my strained panies. He turned towards me and his other hand pushed up beneath my babydoll top to cup my breast and flick my nipple.

I moaned softly and rolled my head towards him. He kissed me deeply, his tongue pushing my lips apart as it slipped into my mouth. I flicked the tip of mine against it and held his head with my hands. Both his hands slid under my babydoll top to cup my breasts and I moaned a bit louder.

Someone sat on my right andI felt him lift the babydoll top over my head from behind then down each arm and off before kissing my neck and nibbling my ear. Leaning back and turning my head I kissed him as the first guy started to kiss, lick and nibble my breasts and nipples. Unable to control myself any longer my body convulsed and I gushed into my already wet panties!

Soon a third set of hands was tugging my panties down and off, leaving me in my jewellry, stay ups and heels only, before his lips closed around my clit. Every nerve ending in my body was on fire, my mind was lost in a sea of sensations flooding my brain, making me moan continuously and turning me into their sextoy to use however they wanted.

Gasping for air, belly convulsing continuously, body spasming helplessly I sucked cock after cock, felt my cheeks parted again and again as men filled my hungry hole, felt their spurts splattering on me everywhere from my hair to toes without coming out of the daze I was in until they were sated and done with me. Even then I wanted more, desperately looking around for someone, but I was alone in the theater.

My babydoll top was soaked with cum, my panties had disappeared, my stay ups were ruined and nearly every inch of me was covered in cum. Yet slut that I was I still wanted more. What was wrong with me? Was I the type of nymphomaniac slut that would never be completely satisfied?

I know my male side was crying inside as I made my way to the washroom to at least get the worst off of me. My make up was ruined. running down my cheeks and across my face, my lips had lost every trace of lipstick, and my hair was a coated mess the cracked mirror attested to me, yet I wore a contented smile even if I did want more.

I cleaned my face as best I could with just water and paper towelling, washed my body and did what I could for my hair with the paper towels and no comb or brush! I rinsed out my nitie top as best I could then carried it over as I peeked out the curtain and tried to get the clerk to bring my coat over.

He came over but just to see if I'd give him a BJ behind the curtain. He wouldn't bring my coat over even if I did that I was told. I'd have to come up to the counter to get it.

"Like this."

"Yeah like you are. You didn't seem to have a problem walking in here before in practically the same state. You suddenly shy?"

"Not so much shy as, well you know."

" Ahhhhh not so brazen after you've had a few cocks and been satisfied, is that it? Well sorry but the boss likes to review the security tapes and I wanna have something for him to see."

He left at that point whistling and chuckling. I peeked out again and there were three guys looking around the store so I waited, rushing out as soon as the store was empty.

The clerk took his time getting my coat, hoping someone would come in I think; either that or making sure the boss man got a good show. I couldn't believe that I actually started posing and preening so he would before I was handed my coat.

He helped me into it then reached around to cup my breast with one hand to pull me back tight and hold me there as the other hand first held and squeezed my sac then stroked my clit! I couldn't stop myself from moaning loudly or responding eagerly! My hands slipped behind me to undo his zipper and reach inside to free his hard cock. A larger man he smiled as he lifted me easily to turn me to face the camera direcly. I barely noticed as he released me enough to tug my coat off and let it fall to the floor.

He played with my breasts and nipples, ran his hands across my waist and hips, went back up to pinch and tug my nipples out, driving me wild. His hands went down to spread my thighs wide as he lifted me and carried me over to place me facedown atop the counter. Keeping my legs spread he moved between them and pushed a thick finger inside me a few times, grunting happily as he discovered I was still fairly open and well lubed.

From the minute or two I'd stroked him I knew his cock was large but now as he pushed it into me I appreciated that more. It was the largest, thickest cock to slide into my hole tonight, if not ever. Briefly I wondered how many times he'd done this before to know that the counter was the right height before he managed to slide all the way inside.

OH migawd yes, yes, yes! I was sure he was probing depths that had never been reached before. As I started to moan and try to thrust myself back onto his wonderful cock a silly thought crossed my mind.

Does anyone remember the scene from Young Frankenstein near the end where Franks new bride first tries to fight him off then starts to sing as he gets it all in. I felt like that! Deliriously happy and completely female in every way poasible.

The counter shook and bounced with every thrust as his balls slapped against me. My nipples slid over the edge of the counter then back unto the counter as my body slid back and forth from his pounding. My thighs and legs were wrapped around his waist and he held my hips tightly as he plunged his cock into me.

Plunging as deep as possible he held it there and I felt my whole body strain as every muscle tightened. I nearly screamed as I felt his first spurt enter me. My body spasmed and convulsed then a fine sheen of sweat covered my body as my muscles released. I spasmed again weakly with every spurt then laid there limply as I gasped for air as he pulled his cock out!

I felt so empty but oh so sated and satisfied for the first time in a long time.

He slapped my ass lightly to revive me and when I looked up I noticed that we had had an audience of two, either that or they'd just walked in. A younger wide eyed couple were staring at me as he turned to see what they wanted while he put his cock away. Still unable to move I laid there catching my breath. Stopping to pick up my coat and throw it to land on my back as he walked out to help the couple.

With a final deep breath I slid back off the counter and pulled my coat on. My nitie was still in it's pocket so I knew my keys would still be there. I turned as I made it to the door and we blew each other a kiss before I stepped outside.

Starting the car I pulled out and began to drive home. Sated the female side left me and I started to cry. I actually cried all the way home and in the shower as my male side was solely in control again. I felt sick, revolted with myself and depressed by my actions. What kind of a girl was I? Whoa, when did I start thinking of myself as a girl? Oh gawd what was happening to my mind?

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
54btmguy54btmguyabout 6 years ago
Great series

I do like the 1 page series as they are short and lead right into the next part. If I knew then what I know now I am sure I would have transitioned except I know I would have kept my little clitty cock but I waited to long to realize I prefer the fem role and being submissive and love pleasing men.

doninpanties1doninpanties1over 6 years ago
great

they were amazing made me feel like I was him.wish I could be that much fun.

AnonymousAnonymousover 6 years ago
Damn, that was HOT!

Oh baby, you have got to keep this going. I am exhausted!

AnonymousAnonymousalmost 7 years ago
brilliant

Just read all 13 chapters. Loved them all.

Share this Story

Similar Stories

Women's Studies Ch. 01 A young man's odyssey trying to attend an all girl college.in Incest/Taboo
Caught Fishing in Bra & Panties Mark finds he likes sucking dick more than fishing.in Transgender & Crossdressers
"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
Sissy Chantel, New Reality Ch. 01 Chantel finds sissy fantasy will become her sissy reality.in Transgender & Crossdressers
My Obsession A young girl becoming a woman.in Transgender & Crossdressers
More Stories