Chronicles of Heather Maureen Ch. 05

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One transvestite's life from start to present.
1.1k words
4.37
12.6k
6

Part 5 of the 13 part series

Updated 06/08/2023
Created 06/02/2016
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My Life with Marty

I spent a lot of time at Marty's over the next couple of years. He explained to mom that his 'son' had trouble making any friends and he'd been so glad when I became 'Jason's' friend after meeting him at school. Thus Marty and mom got to know each other thru the frequent phone calls asking if I could stay over or spend a weekend, again. Mom was happy enough that I had a good friend, Marty was happy to have a Sissy to play with and I was overjoyed to have a place I could be feminine and dress openly. Winner, winner, winner!!

After that first excursion in the park Marty kept slowly increasing the amount of risk I was forced to take. I loved the rush it gave me, both during and after, no matter how risky it became; in fact the more risky it was the more I enjoyed it! From full lingerie', to topless with the breastforms glued on at first then later just topless, to stay ups and panties with a sheer or transparent babydoll or longer nitie, to higher and higher heels that I could barely walk in, let alone run in if I needed to, all the way to heels and just panties! From secluded parks to more open ones, to walks along country roads at night, then during the evening, then during full daylight, and finally to 'deserted' city streets during the evening or nights! More than once a car suddenly appeared from around a corner and a startled driver suddenly applied the brakes to make sure of what they'd seen or there'd be someone up with the lights off but looking out their window for some reason who'd maybe give me a wave. I'd blush a bit, shiver inside and wave back with a big smile on my face. I thrived on it and Marty always loved the results after. Then there were elevator rides inside some building where either just security or possibly everyone in the building could be watching on their TV. He'd press the floor and step out and I usually had to walk back down the stairs, if I could find them. Some nights my panties would get so wet I'd have to change them three or four times.

Displaying my lingerie clad, semi clad and barely clad body out of the house was one thing; displaying it inside the house another. The initial rush of someone seeing my body covered in only a mist was exciting at first when Marty's friends dropped over for a night but the rush wore off in awhile. What kept me excited those nights was the sudden feel of one of their hands along my thigh, cupping or running over my lower cheeks, tweaking my swollen nipples or the small breasts I was developing now that Marty's Doctor friend had started prescribing hormones for me. I did want real noticeable breasts but wanted to be able to hide them at home. What a quandary it made! I'd have loved to be fully developed but ... I had graduated so there was no problem with phys. ed. classes anymore. A couple of the guys had looked at me strangely just for being hairless in the showers; what would they have thought or said if I'd been developing at that point.

Removing the cups from a couple of my bras to make them breasthalters did a lot to accent and round out my breasts to A or A+ cup size at that time. Marty liked both the look and sensitivity. So did I but they were possibly too sensitive. More than once Marty or one of his friends had proven that they could literally remove whatever I had on while they sucked, nibbled or even just played with my nipples and I wouldn't know it till after they stopped! Now they all delighted in doing that to me. Marty kept an eye on his friends to make sure they didn't go too far without his permission; after all I was his Sissy. That didn't mean that I didn't have to suck or get laid by one or the other from time to time, or even have to do several of them in a single night if Marty felt like it. I discovered that I could ask Marty without repercussions but there was hell to pay if I didn't and get a yes answer or didn't ask!

I might have lost control when Leroy played with my nipples, I might have been too excited to say no when he first entered me but at some point I should have fought him off I was told before Marty placed me over his knee, pulled my panties down and gave a sound spanking that made it hard to sit down for the next week. I learned not to give in so easily very quickly and watched myself after that! To help me with that Marty insisted that I start wearing a chastity device only he had the key to. It wasn't just to cover and control my clit but covered my anus as well! I had to ask politely every time I needed to use the washroom or become very, very messy!

Learning to be Marty's feminine, submissive, exhibitionist Sissy wasn't all that he taught me. After a few months spent learning those lessons Marty asked me if I trusted him enough to let him tie me up. When I agreed he first just tied me to the bed and teased me mercilessly until I was ready to promise him anything for sexual release, begging and begging him to fuck me as I struggled against the bonds. He'd just listen and play with me some more until I was quivering and spasming on the edge of release then stop, again! When he finally did relent and allow me to orgasm I'd come near to passing out it was so intense. Later he'd made a 2x4 square he'd tie me to in the living room and tease me mercilessly there both during and after making me watch Transvestite pornos for hours. Once in awhile he'd use me as a centerpiece or wall ornament when he had friends over or threw a party while tied in it.

All in all my life as Marty's Sissy was quite the learning experience, quite the revelation about my needs, my inner desires and myself and quite the focus of where I'd end up in life. Marty got transferred while I was in my second year of university and there was no way I could go along. None of his friends quite fit the bill of what I wanted and those few that came close either had a Sissy or didn't want one full time. I fell back into my old humdrum life spending less and less time dressing and feminising myself and plunged more into my studies. Eventually I started dating a girl and for a time suppressed my transvestism, exhibitionism and submissiveness; but it was only suppressed not gone from my life.

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AnonymousAnonymousalmost 8 years ago
the weekend

It would've been nice to include the weekend camping trip that was mentioned in an earlier chapter.

cali_fraecali_fraealmost 8 years ago
The end?

Ive enjoyed the 1st 4 parts of your story but it felt like this was more of a summary/epilogue. There was definitely enough points of intrest in this last chapter that you couldve expanded upon to make it as good/long as the previous parts buts thats just my opinion.

Im hoping that the reason you wrapped things up in this way is that you feel your done with the Marty time in Heathers life & wish to write about the rest of her experiences, if so i for 1 will be reading.

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