Chronicles of Heather Maureen Ch. 09

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One transvestite's life from start to present.
2.1k words
4.43
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Part 9 of the 13 part series

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

While I was waiting in bed last night for George to join me he had gathered up my clothes and purse then locked them in my car to make sure I'd spend the day with him. His clothes would fit me like a tent and his wife's merely like a pup tent so they were no help. I resigned myself to staying here and inside for the day. He made breakfast for us with a big smile on his face and I did the clean up after. Then with nothing else to do I made the bed, swept the floors and dusted the place; something George hadn't done for a long time.

He watched me and read the paper, still smiling. I started to open the curtains and windows to let in some fresh air, peeking out to make sure I wouldn't be seen first but George came behind me closing the curtains. He didn't want anyone peeking in to see me running around naked. I jokingly asked him if he was ashamed of me.

"No, I'm not embarassed being seen with you, I just don't want the neighbors seeing you this way. I want you all to myself today!"

"And how would the neighbors seeing me cleaning your house without any clothes prevent that?"

"It would detract from my enjoyment."

I rolled my eyes a bit but didn't argue or point out that I only opened the curtains when I'd finished a room and was moving to the next. It's funny but I felt comfortable being nude in front of him even tho he was fully dressed. Somehow it just felt right.

It took all morning before I was finished only because it was a small house. I showered as he made lunch. The place looked and felt so different now but there was still lots to do. His wife's room should be emptied of her things, the basement should have all the hoarded things cleaned out, old newspapers, stuff stored there but never used anymore, that kind of thing.

George said I'd done enough tho so we sat together and watched television with his arm around me. I did manage to get him to bring my purse in so I could do my face finally. He'd thought I could use his wife's leftover make up but it was all so old it wasn't usable. Some of the powdered eyecolors might be but that was all. I felt better with my face done, more feminine again. I'd been flashing sort of back and forth between each side of my brain all day due to George's size, which made me feel so much smaller and more submissive. Now the feminine side was firmly in control.

Yes he did a bit of fondling and carressing with lots of kissing and hugging and I had to remake the bed twice after he got worked up enough to carry me in there to gently, tenderly make love to me. We showered together after each time. He told me it was a first for him and I believed him.

He didn't want to let me return to the park that evening. I felt like I should go even if just to 'achieve a passing grade from my teacher', LOL. Finally he sighed and got my schoolgirl outfit from my car and left the keys on the table. He made me promise to return before he let me out of the house.

The 'teacher' was waiting at the bench when I got there. He smiled widely as he looked at me then shook his head.

"Not only are you late for your exam but apparently you learned nothing from last night's reprimand about your mode of dress!"

He stood up and walked around me.

"Perhaps you'd learn it better if I made you stand in the corner naked or tied you there for the boys you seem to like teasing so much to relieve themselves! Is that what you want? Very well take off your skirt and blouse, NOW!"

I jumped at the forcefullness of the last word and stood there frozen for a few seconds before slowly removing my blouse and skirt. He walked around me again.

"That's better but I said you'd be naked for them, didn't I! Take off that ridiculous bra and your panties."

I undid the bra and set it atop my skirt then slid my panties down and stepped out of them. I tossed them on the pile and stood up straight again.

"There now all the boys can see that you aren't really a sexy little schoolgirl slut. Turn around slowly for them so everyone can see that they have been lusting after a little Sissy schoolboy slut dressed like a girl. Take a good look boys! Yes he has nice titties and a nice firm round butt but is he really a girl with that thing between his legs?"

I was getting so much into his fantasy that I could practically see my classmates, see their stunned looks, feel their eyes on me, hear their jeers and catcalls, their ridicule and taunts as I blushed in my humiliation. Under that stimulus I cowered and started to try and cover myself with my hands but he grabbed them and pulled them behind me.

"No, Missy, don't try to hide anything. They deserve to know what you are, what they've been lusting after and wanting all year. Don't you agree, Missy? Don't you want them to know you're really a little Sissy Schoolboy Slut who is so submissive he will take his clothes off in front of them when told to? Hmmm, yes that should be enough. Your stockings and heels can stay on, they just accent your nakedness and submissive feminine nature. "

I felt so humiliated, so embarassed, so ashamed at that moment. He held my hands behind my back with one of his and had a loop of rope tightening around one wrist before I knew what was happening! Tugging me around to face the bench he wrapped the rope around the bottom rung on the back of the bench and then my other wrist, snugging it firmly before tying it tightly.

"Now boys I am going to show you exactly how to treat submissive little sissy sluts. First you make sure they are bent over like this. Then you check to make sure they aren't too tight by fingering them with first one finger, yes it's sliding in easily; then a second one, yes still fairly easy to do and even a third one, yes she's stretched open enough."

He slid his fingers in as deep as possbile then wriggled them inside me. I squirmed a bit and moaned softly.

"This little sissy slut doesn't seem to mind being fingered, none of them should really, and you can see how easily my fingers slide inside. She must have used some lubricant earlier just for this it's so slippery and easy. "

He lightly slapped my thighs so I'd spread them further apart then he removed his fingers. I heard his zipper being undone, felt the head of his cock slide between my cheeks and gasped as it popped inside. He stopped there for a minute. I pressed back to take more of him inside but he moved with me and left just the head in place.

"Aren't you going to ask me to fuck you little sissy schoolgirl slut? Aren't you going to beg me to fuck you? Don't you want more then just the head of my cock inside you?"

"Oh yes please, please put your whole cock inside me Sir. Please, please fuck your little sissy schoolgirl slut! Please sir, please fuck me, please, please Sir!"

" See how nicely, how submissively, how prettly she begs me to fuck her boys? Remember that boys, make them beg for it and when they have you know they want it so bad you can do whatever you want to them! Only then should you slide your cock in as deep as it will go, like this."

Holding my hips he pressed his cock deeper then slid it out before plunging deeper and deeper with each thrust till his balls slapped against me. Gripping the back of the bench with my bound hands I did my best to rock my bottom back to meet him, gasping and moaning constantly. My breasts bounced and swayed as my body was slammed back and forth.

George's tender gentle lovemaking during the day had been great and I'd cum every time with him today but this was so much more exciting. I spasmed as soon as his balls first slapped against me then a second time when he slapped my cheeks before he finally spurted inside me and sent me into a third orgasm.

What was so different? What made it so much more exciting right now? Did I need or want to be humiliated, to be forced to admit my submissiveness, and made to go thru the exhibitionism? Did I prefer a touch of roughness for some reason? What was wrong with me? Was anything wrong? I struggled to catch my breath feeling sated as those thoughts flickered thru my mind.

He withdrew from me and I heard his zipper being pulled up.

"You passed your in depth exam admirably Miss. Are you up for some extra credit now? I wasn't just lecturing you, you know. I have two friends hiding in the shadows who always wanted to meet a shemale in real life. Let me introduce you.

Fred, Allen, come over here and meet the young lady."

His two friends came out of the bushes and stood in front of me. He started to introduce us to each other then realised he didn't know my name. Heather Maureen I told him and he finished the introductions.

"I'd shake your hands gentlemen but I'm still tied to the back of the bench."

"UM, yes about that. I wasn't sure you wouldn't run off if I untied you and then sprung this on you. This way I knew you'd stay here long enough to meet them at least. If you're willing I'm sure they'd like to do much more."

I smiled up at the two of them from my bent over position, thought about it for a few seconds and figured why not. After all this was why I came to this park! I replied sure but could I be untied first? And what was it they wanted to do?

They didn't have any idea as they hadn't quite thought that far ahead, not really believing their friend when he'd told them about me. Teach untied me and I stood up straight and stretched. I walked behind the bench to where they were standing, not bothering to try and dress then undid their pants, freed their cocks, sank to my knees and started to suck first one then the other, going back and forth between them.

Neither lasted very long. I managed to swallow one load but the other sprayed out over my face, shoulders, chest and breasts before I could. One offered me a hanky to wipe myself off and seemed amazed that I used my fingers to wipe up as much as I could and licked them off first. (I only did that to be as sluttish as possible in front of them and whoever else might be hiding out of sight watching us.)

Standing up in front of them I used the hanky to finish cleaning myself as best possible and smiled at them, welcoming their rapt gazes. I moaned softly as first one then the other reached out to cup and fondle my breasts, flick their thumbs across my swollen puffy nipples and moaned softly as the sensations lit firey trails inside me. My body trembled as they each leaned forward to suckle, nibble and kiss my nipples. Their hands cupped my lower cheeks, caressed my thighs, moved over my smooth body, making me tremble and sway as my knees became rubbery. Impossible as it seemed to me I was becoming sexually excited again.

Teach knelt and took my clit between his lips. I lost control from all the sensations flooding my brain so it wasn't long before he swallowed what little was left in me. If they hadn't held me up and sat me on the bench I would have collaspsed on the ground. We chatted a bit as I recovered then they left as I stood up and started to get dressed.

I'd sort of agreed to meet them tomorrow, if possible, in the park again after it got dark. Another guy came along but I told him I had to get home and walked away saying I might be back here tomorrow if he showed up a bit earlier. He said he might.

I had promised George I'd return but I really needed to go home, shower and change first, if nothing else. But when I got home I was too tired and after sitting down to rest a bit fell asleep on the couch still in my schoolgirl uniform.

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