Chronicles of Heather Maureen Ch. 03

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One transvestite's life from start to present.
1.7k words
4.59
16.1k
12

Part 3 of the 13 part series

Updated 06/08/2023
Created 06/02/2016
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A Day with Marty

Somehow Marty had talked my mother into letting me spend the day with him and his 'son' and skip school. (I wasn't sure what I'd do if mom ever wanted to meet them but that a problem for later.) After asking me a few questions he now knew that I really didn't have a place I could openly dress femininely, only two actually presentable outfits, little experience with make up or with styling my hair. He decided we needed to do something about that. If I wanted I could come over to his place under the condition that I had to only dress femininely when I was there. If I agreed then he would help me acquire a proper wardrobe, find me someone to help me with my hair and make up and let me store my things here. I would be his Sissy / Gurltoy and there would be a few simple rules for me to follow but he'd explain them as we went along. It took me a whole minute to get over being stunned enough to agree. Grinning from ear to ear he led me his car by the hand. When I sat next to him at first he suggested that I move over more to my side, at least during the day, when we were in his car.

I have no idea how much money he spent but he took me to a couple of stores where he knew the owners. In the first I was fitted for silicon breastforms and shown how to properly glue them in place so they would stay there even if I went braless! The next was a lingerie' shop where he made me not only try everything on but wear it out to model it for him. I started off with a bra, garter belt and panty set. It was nerve racking to walk out of the change room for his, and everyone else in the stores, inspection. I was blushing all the way down to my toes and had a bellyfull of butterflys at first. By the time I had modelled three sets he had selected several fairly sheer babydoll nities, a couple of very sheer babydoll and mid thigh length and floor length ones and a few transparent ones as well. I felt so wicked and naughty and incredibly excited by the time I was finished modelling them, as he'd known I would. I had gone from embarrassed to brazen and the owner of the store told me to 'cool it' before someone passing by glanced in and complained to the police; though he smiled widely as he said it.

The third shop was for skater length dresses and skirts, as they are now known, ( back then it was mini or micro mini ). A couple of blouses and a mid thigh coat and a jacket for cooler days or nightsand we were set. He had an inaudible conversation with the owner at one point, the upshot of which was the owner pulling out a tape measure and measuring me every possible way. Finally it was high heels and even higher heels that left me wobbling all over the place. It would take practise I was told but, the more I wore them the easier I would find it to walk in them!

Back at Marty's we unloaded the back seat and he showed me what was ostensibly going to be 'my' room. He helped me unpack everything and set it away. The dresses, skirts, blouses and heels went into the closet and the rest in various drawers of the dresser. Marty set one of the more transparent babydoll nities atop the bed and smiled as he said that was for later! Then it was off again to a make up counter where he explained to the salesclerk that his 'daughter' required a makeover and a few lessons in how to properly apply make up to look more refined and cultured now that she was going to be living with him. (Living with him!) He left to wander about the store, dropping back a few times as the session proceeded then bought everything the girl suggested when it was done. I'd learned a lot; daytime make up, evening make up, special tricks to accent this or that, mostly my eyes and lips and others to help make flaws less obvious. I really hoped I'd remember even half of it.

During the silent ride back to his place I realised that all the doubts and confusion about myself and my sanity, the sense of immorality about what I'd done the night before that I'd felt at first this morning had evaporated and disappeared! Just as Marty had known I'd come to love the exhibitionism in the store he had been right when he stopped me from rushing out the door in shame the way I'd felt like doing. I also realised that at several points I had been in full control for short periods, not merely an observer of my body, and fully enjoyed what I was doing. Both were quite the revelations! I mentioned them to Marty and he smiled.

"Yes, it can take awhile before one can come to grips with discovering that what they want and need are so different from what they'd been raised to want and need. In my case the fact that I'd come to accept the fact that I enjoyed dressing femininely and being thought of as a girl when I had gone out dressed might have softened the blow a little, but he didn't think I was thru the woods yet. It would come back again and again to haunt me, just less severely then this morning. Now I'd be a bit better prepared to handle it when it did!"

I sat back and considered his words until we arrived at his place.

Over spiked coffees Marty asked me if I attached any special meaning to being called his Sissy Gurltoy. I shook my head negatively as I really didn't. Well as a Sissy I was expected to listen to him and do as he said. There would be certain rules for me to follow, such as when I was with him I'd always be dressed femininely, no matter where we were, with my face and nails done and only speak when spoken to. Here at home I would only be allowed to wear one of the nities he'd bought me, unless told different. He'd select the nitie at first, todays was the one set atop the bed in my room, until such time as I learned what he preferred me to have on for him.

When he had a friend or friends over he liked showing his Sissy; and if they happened to touch, stroke or do anything else to my body I was to let them, short of any type of actual intercourse, without his permission. I nodded when he asked me if I understood and accepted these rules. There would be others added but for now these would do I was told. He looked at me expectantly and raised an eyebrow as he glanced around while I took a sip of my coffee.

His meaning hit me and I jumped up to rush to my room, undoing buttons as I did. As quickly as I could I stripped off my clothes and slipped on the transparent black babydoll nitie and matching panties. Under them was a new pair of sheer black stay ups that I sat down to roll up my legs and by the foot of the bed was a pair of four inch black heels I stepped into. I checked my make up in the dresser mirror and teased my hair a bit for more body before really looking at my reflection. With the falsies still in place I looked very feminine! I felt so wicked and naughty as I stared at my barely misted body clearly visible thru the nitie. I might as well have been completely naked, but that wouldn't have been nearly as sensual.

With a lot more decorum that I'd shown going to my room I returned. I couldn't take my eyes off my reflection in the mirrored wall behind Marty, feeling even more naughty and excited as I walked towards him. With every step I fell into a more feminine stance, gained more feminine grace, gave myself a more feminine sway; or so I felt at least. I not only saw but felt my 'breasts' jiggle and sway enticingly from side to side with every step! Without either of us saying a word I stopped right in front of Marty, knelt down and undid his zipper. Freeing his cock I kissed the tip, closed my eys and started sucking him eagerly, taking as much of his shaft as I could cram between my lips. I glanced up to see his shit eating grin as I slid up and down his shaft and smiled around his cock, knowing that this was what we both wanted right now. I stopped for a second when I realised that this was me in control of my actions, I'd been so caught up in the sensuality of the sensations flooding my mind, the feeling of the nitie against my smooth skin, the jiggle and sway of my breasts, the overpowering sight of how feminine and sexy I looked that I hadn't thought about it until this second! This was really me kneeling here and sucking a cock! It was me, not someone or something else in control, and I was enjoying it!

I wondered if Marty knew why'd I'd stopped for those few seconds as I managed to finish taking his whole cock in my mouth. As I rose to the tip I'd swirl my tongue around the head then back down the shaft to lead my lips. I gagged a bit when he spurted, not quite ready for it, but swallowed automatically without thinking about what I was doing. Marty slumped back in relaxation as I licked him clean then cleaned the rest from around my lips before rising to stand in front of him. He pulled me unto his lap and kissed me deeply then held me close.

"Yes you are truly perfect in so many ways my little Sissy. I think we will have a lot of fun together."

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mumblegooseeggmumblegooseeggover 7 years ago
Great story so far

Your story inspires me with some very pleasant fantasies and dreams, probably because of the way you depict so well what Heather Maureen is thinking and feeling, and I let myself try out those thoughts and feelings for myself, seeking differences and similarities with how I am in real life. It's a very instructive and, dare I say, erotic activity!

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