Chronicles of Heather Maureen Ch. 08

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The life of one transvestite from start to present.
2.6k words
4.57
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Part 8 of the 13 part series

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

My paranoia about being seen or recognised going home was needless worry as I made it into my place without notice. Would anyone have cared even if they had seen me? Friends or family maybe but who else, my neighbors? I smiled ruefully as the thought crossed my mind that for the first time I'd just suffered thru the 'walk of shame'!

I rushed to change back to male mode and make it to my classes on time. I thought about George a lot during the day, wondering why he was so timid and why I found that so endearing. I felt more in control of things with him but was more used to being told what to do or just having it done to me. Did that mean I was less of a Sissy? (It didn't mean I was less of a slut as I hadn't gone to George's for the conversation!)

When the day was done I had a nap and really planned to just stay home. Once I was awake and moving tho I found myself doing my face, polishing my nails, styling my hair and dressing to go back to the park. Tonight it was the schoolgirl look. Pigtailed hair in ribbons, mostly hot pink colored make up and nail polish, extremely short plaid wrap around skirt, unbuttoned white cotton blouse tied between my breasts, ruffled white nylon panties that were on display if I was bent even slightly or was sitting, mid thigh length sheer white stay ups and two and a half inch heeled black sandals with ankle straps. I had a white lace breast halter on to make the most of my small breasts and my rouged nipples were prominent thru the thin blouse.

George was waiting when I got to 'my' bench! He smiled at the school uniform and told me I looked very lovely and very sexy dressed in it. I smiled, lit a cigarette and sat beside him. I teased him about being there two nights in a row after telling me he didn't come here very often. He smiled and told me he would have if I'd been here before. I rolled my eyes but smiled at the compliment. He wanted me to come back to his place right away and I considered it. I did want to stay for an hour or so at least after dressing this way I told him. He said he understood but looked disappointed. His hands found their way into my panties and eased them down. I gasped as his lips sucked my clit. Already overly excited from dressing this way I didn't last too long. George seemed very pleased with himself. He kissed my forehead and told me to enjoy myself, he'd be back in an hour or so.

As soon as he left a mid twenties male moved out of the shadows he'd been watching us from. He was already stroking his cock.

"That was hot watching that old guy blow you." His eyes moved up and down my body. "So you're a sexy little schoolgirl, are you? Stand up sexy little schoolgirl so I can get a good look at you."

I shivered and stood up slowly, feeling my knees becoming rubbery under his gaze. I had to keep one hand on the back of the bench to steady myself. His eyes continually moved up and down my body, undressing me of what little I had on and making me tingle all over. I felt more naked then last night somehow. My nipples throbbed and ached, my belly undulated as I gasped for air and my whole body shook as he inspected me.

He continued to stroke his cock with one hand the whole time. Quickly reaching out with the other he tugged at the loose knot of my blouse and it fell open. His smile widened as he stared at my small breasts and the swollen puffy pink nipples atop them. Taking one nipple between finger and thumb he tugged it out then rolled it roughly between them. I spasmed slightly and closed my eyes as I gasped. I gasped again when he did the same to the other nipple.

"You are such a naughty little schoolgirl, letting the boys see you dressed so slutty and leaving so little to their imaginations. You're such a wicked, naughty, slutty little schoolgirl showing your titties off to your teacher like this. Did you think I'd raise your grade to a pass for this?"

He stopped stroking his cock and both hands squeezed my breasts or tugged my nipples out a bit painfully, jerking my body forward slightly. One hand dropped down to tug at the velcro tab of my skirt. With a slight ripping sound it easily came undone and he stood there with it in his hand. He chuckled and threw it on the bench.

"So that's what my little schoolgirl slut wears under her uniform when she's trying to improve her grades?" He grabbed me by one arm and pulled me away from the bench then walked around me, inspecting me again. "Take your panties off little schoolgirl slut, take them off NOW!"

Shaking and trembling I managed to slide my panties down my legs and stepped out of them.

"Oh my god. What do we have here? You're not a little schoolgirl slut, you're a naughty little schoolboy slut dressed like a girl! You could be kicked out of school for this you know. Pretending to be a girl and teasing all the boys with the way you dress and look. Oh my! I just don't know what to do now. I just don't know what to do with you."

I was going to give you a bare bottomed spanking to teach you not to tease the boys by dressing like this all the time. You're always looking so naughty, so slutty and sexy and making it hard for them, and your teachers, to concentrate in class! Now to discover that you aren't even really a girl, even if you do have such nice titties. I should tell the principal and have you kicked out immediately!

I don't want to have to do that. Tell you what, I'm not going to say a word if you can manage to pass the two make up exams I'm going to give you."

Smiling he sat down on the bench and told me to face him. I turned and stood there trembling with my head bowed and my hands clasped behind my back. He shook his head from side to side, still smiling widely.

"Whether you pass or not is up to you but either way you still deserve that spanking. Get over my lap, NOW!"

Sitting on the end of the bench he swiveled so his legs were sticking out from it and I wouldn't be on it at all. I lowered myself down across his lap, feeling his very hard cock press against me. His hand rubbed each cheek roughly then suddenly SWAT, SWAT, SWAT, SWAT! His hand delivered two blows to each cheek. I jerked and jumped at each swat, biting my lower lip to muffle my cries as I felt each cheek turning red. He rubbed each cheek slowly again then SWAT, SWAT, SWAT, SWAT. Two more to each cheek. I squirmed and flinched from each swat but this time I let my cries out.

I could feel the heat rising from my cheeks now! He continued swatting , two swats to each cheek then a quick rub till he had delivered ten to each. My cheeks were fairly numb after the second set and so I didn't cry out any more. I could feel the heat from my cheeks spreading thru my belly directly to my crotch, my nipples throbbed and ached and my pulse pounded in my throat. After the first two to either side he emphasised his words with every swat.

"This is to TEACH you NOT to show up for school dressed like a NAUGHTY SLUT to tease the boys the way you do. This is to TEACH you NOT to be the kind of SLUT who thinks SHE can show her TITTIES to her TEACHER to get better grades. Your SEXY little SCHOOLGIRL looks and TRICKS aren't going to help you in the REAL world, especially since you aren't even a REAL GIRL!"

He dumped me off his lap at the end and with a big smile said I'd better do good on the 'oral' exam. Rising to my knees I opened my lips and started taking that 'oral' exam. The previous stroking he'd done, the roleplay and giving me a spanking must have made him very aroused. I'd barely managed to make my way down to the bottom of his shaft before he exploded! I swallowed as much as I could then licked the rest up from his lap and cock before I cleaned my face.

"MMMMMMMM Yes, You'll be getting an A on your oral exam. Ha ha ha! Nice to know I am that good a teacher, as you didn't have much time to prepare! There's still another exam I'll have to put you thru before your grades will be high enough to pass my class but it's a, um, more penetrating and in depth test of your abilities. You have tonight to get prepared but be here at this time tomorrow for that exam, Miss!"

I smiled and nodded. He got up and walked off and I put my things back on. I was surprised when I noticed a small group of men had been watching from the shadows around us. George was one and he came over quickly, took me by the arm and said the hour was up so now I should come over to his place. I was just getting started really but my ass was sore from the spanking so I went with him. Again I followed along behind but this time he made me park in his garage, more discrete he said.

Inside he made coffee for us and we sat at the kitchen table facing each other. I sat gingerly on the edge of the chair as my ass was a bit tender. George looked a bit troubled as he told me he hadn't gone far before circling back. He'd enjoyed watching me with the other man at first until he told me what to do. Then when I was being spanked he'd been tempted to rush over to stop it until he saw the look on my face and realised I must be enjoying it. He didn't understand that but accepted it.

Did I really enjoy that kind of thing? I'd smiled and sort of jumped then quickly did whatever the man had told me to when he had barked at me, too. Did I enjoy that? I had to stop and think about what to say before I could answer.

I did my best to try and explain that I had been Marty's Sissy for nearly two years and Marty had enjoyed controlling me. I had either learned to be or enjoyed being controlled I'd discovered! Marty seemed to understand what I wanted and needed better than I did right from the start. He was the one who had showed me just how much dressing the way I did and becoming the slutty Sissy exhibitionist he enjoyed using excited and aroused me.

George sat there sipping his coffee for a minute then asked me if something like that was what I really wanted or more of a normal relationship. Avoiding the question I asked him why he'd stayed in the relationship he described between him and his wife. He'd never been a forceful man and it suited him. It hadn't always been that way, at first his wife had been more of a normal wife but as time passed things slowly changed, she didn't enjoy sex as much, she started bossing him around a bit and he put up with it because marriage was sacred. Towards the end they'd grown even further apart. He could never look at another woman while she was alive and going to the park to be with another man wasn't really right either, but when they were dressed like women it was different somehow. Doing that he wasn't with a man or a woman really, it was just different.

Then when she passed away he didn't want be with a woman anymore, too much trouble, so he kept going to the park, content just to enjoy those that liked to dress like women. He still seemed very thoughtful as I cleaned up our mess, washed and dried the cups and said I should be going.

No he said, I want to hold you again tonight, all night. I slept the best I have in years with you beside me. It's the weekend and we can sleep late, have breakfast and just be together for awhile. I started to say I still should go when he stood up and pulled me close to kiss me. Kisses and nipple play were my two great weaknesses. I melted against him as his tongue found its way into my mouth.

A slight tug and my blouse was open and being gently slid off my shoulders. Another at my waist and the small velcro tab holding my skirt closed gave up the ghost and it dropped to the floor. George fumbled with the hooks of the breasthalter then slid it off me before sliding my panties down and off. Kneeling he undid my heels and rolled the stay ups off to leave me totally naked.

I was trembling slightly, feeling so small, vulnerable and weak next to him he was so much larger. He stepped back and looked down at me, then told me to go get into bed while he checked things for the night, he'd be right in.

I got under the covers and waited. George was only a few minutes behind and soon holding me against him again. I snuggled tight and kissed his neck. He tilted my face up and kissed me again, and again, and again, as his hands lit small fires in my throbbing nipples, along my sensitive thighs, thru my belly and crotch.

He rolled above me, sliding easily between my legs and smiled down as he positioned himself. I was pre lubed from the butt plug I'd inserted and removed earlier so he had no problem sliding his cock into me. I pushed up to meet his thrusts and moaned softly as he slid deeper and deeper inside me then wrapped my legs around him. Still holding himself above me on his hands he was in no rush as he plumbed my depths with long deep thrusts of his hard cock and smiled down.

"It's been a long, long time since I did this to anyone. A very long time. Thank you for letting me make love to you."

That sounded like the old George and I smiled back as I moaned a bit more loudly at the sensations flooding my mind. The first few times with Marty had been somewhat painful but I'd come to enjoy the sensation of having a hard cock inside me and absolutely loved the feeling of a man orgasming inside me. The spurts from a cock always sent me over the edge now and this time proved no different.

When George came every muscle in my body tightened and stretched, my legs pulled him deeper and my nails dug into his back as I orgasmed with him. I felt him soften inside me, keeping my legs wrapped around him to hold him there longer. I didn't want him to pull out, but all good things must end sometime. He rolled off me but kept an arm around my shoulders and held me close. Tender kisses to my neck and lips were bestowed on me before we fell asleep.

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