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  • Tranny Tales Ch. 08: Driving Miss Daisy

Tranny Tales Ch. 08: Driving Miss Daisy

12

Please note-- this story contains graphic sex descriptions between participants who are over the age of 18. All sex scenes described are consensual.

*****

Tranny Tales #8--PreOp Tranny Sub Gets Gang Banged

I wasn't always gay, or a Tranny for that matter, although it's turned out that way for the moment. I dated in college, even pinned a girl named Roberta Dikeman, who as a result allowed me to have missionary position sex with her. She promised to give me her red Mustang if we got married. I can't say the sex was very frequent or desirable.

Roberta was a large woman, not thin but had a pretty face, blue green eyes slightly hooded so that at times she looked like a female bald eagle, although she was not bald. In fact she was covered with hair. Her under arm pits were a disaster. Even her nipples had a few hairs breaking through. But she did have a clear complexion, two big boobs and enough coarse curly hair on her pussy to make it look like a muskrat pelt. Sex with her was like fucking a brillo pad. But something never seemed right. I kept wishing Roberta was really Robert. In fact, I made that Freudian slip more than once while we were having intercourse, at the moment I came she said, "I love you David." And I responded, "I love you Robert----a."

I was trying to be the son my father had raised but I still felt like a little girl, in fact my mother often dressed me in my older sister's clothes. The sex with Roberta was ok, mostly I loved playing with her breasts, but fucking her was nothing like the thrill of getting my bottom fucked by one of my fraternity brothers, so drunk he didn't even remember it the next day, and I didn't remind him. Butt fucking a frat brother was enough to get you expelled from the frat house so I kept it cool.

I guess it was after that night when I began to suspect that all my life I was moving in a certain direction. I wanted to be a girl. I realized exactly where I was headed when Roberta and I attended the costume Halloween Ball. Roberta went as a mountaineer and dressed me as Daisy Mae. My hair was always a mousey brown, but she dyed it a honey blond and I liked it. She lent me a pair of high heels that were tight on her but fit me fine. I sewed an old plaid tablecloth into a short one- button mini skirt and stuffed an old bra of her's with foam. Everyone thought I looked great, a few guys even asked me to dance and when they held me close I could feel their erection. They all loved my legs and even made passes at me, one squeezed my ass several times and that really excited me.

I've been through a lot in preparation for my sex change operation. I've lived like a woman full time for 3 years, undergone sex change or gender reassignment counseling from a psychiatrist and a social worker, changed my name from David O'Day to Daisy O'Day and I've had my breasts enlarged to a 36D just like Marilyn, my idol.

As much as I miss getting fucked down at the gay bath house, once I had my tits installed they no longer made me feel welcome; although Andre, the cashier said to me in his cute Mexican accent, "Honey we don't do tits here but if you wanna get fucked, I mean any old time, I do you." I tipped him an extra two dollars that day but I haven't been back since. I thought that was very nice of him but he'd fucked just about every guy in the place and behind his back they all called him "pee-wee."

My shrink felt I should continue work in my chosen field, I was a Social Science major at Ball University, the famous midwestern teacher's college. Yes, we all thought the name was inappropriate, but it was named after the Ball Brothers, those two guys who invented the jam jars with the two piece gilt vacuum lids. I was offered a fencing scholarship and I accepted.

There were only about eight of us in the program. A Hungarian Grand Master was our trainer. If you know anything about Fencing, and I'd been doing it since I was 8 years old, my skill was based on the fact that I was of medium height, 5 foot 9 inches but my arms were a little longer then most fencers my size. I was also very fast and as Gregor would say, "light on your feet like humming-birdy."

Our exercises were somewhat like ballet exercises, a lot of squats and quarter squats that gave me a very firm shapely ass. The Hungarian Grand Master was always trying to get me alone to practice what he had in mind for me, I finally let him have his way with me in the few days before graduation. I guess it was a kind of thank you mercy fuck.

Gregor was in his late fifties, an age I thought was very attractive for a man. He was very strong, had a great ass and a nice cock covered with shaggy grey hair. He pinned me against the thick gym mat that hung from the wall, pulled down my fencing pants and really took my ass by force, but I figured I owed him. I don't think he ejaculated inside me but his expression afterwards implied he'd orgasmed. I felt warm and moist but mostly dry except for the lube he rubbed on his cock. When I asked him if he came, he mumbled something about his prostate but he was still happy enough to write me several letters of recommendation.

Unfortunately, Roberta walked in on us just as he nailed me and she shouted,

"Oh my sweet Jesus, you're a gay fuck,"

"Not exactly," I corrected her, "I'm being gay fucked."

"Sure," she said, "that's why you've got such a big hard on."

And with those parting words she turned and left and never spoke to me again. She returned my fraternity pin by special delivery the very next day. I felt very bad about the whole thing but I knew it was for the best, for both of us.

Moving this story back to the present, I'm now three years out of college. I have my teacher's license with my name changed in court to Daisy and the Teacher's Certification Office accredited me in three subjects, English, History and Basic Math. That I could never figure out, I was a terrible math student.

When I went to apply for a teaching position I was told that it was the middle of the term and my chance of gaining full time employment would have to wait until the few weeks prior to the close of the "track," as they now call the public school semesters. The teacher placement interviewer suggested in the meantime I sign up for substitute teaching to get some experience and get known in the system. "If they like you they can ask us to hire you." That sounded like a good idea.

A few days later, I got the call early in the morning, around 6 a.m. They offered me the chance to work as a substitute over in East L.A. I knew that's kind of a tough area but what the hell, I was once a man, now "I am woman, hear me roar." I just love Helen Redding. I felt I could do anything. I was scheduled for my sex reassignment change surgery in six months so I could use the extra money. They don't re-gender you for free.

I drove my little red Fiat through heavy traffic over the bridge that takes you to East L.A., arrived at the High School a few minutes early and I parked in the teacher's lot. On my way to check in at the office I passed a group of Chinese girls playing a novel circular jump rope game. They seemed to be having a good time. Some of the boys on the lot looked too old to still be in high school but I would do my best.

"Now Miss O'day," said the Principal, Dr. Gobi, who spoke with a quasi English accent, maybe he was a Pakistani,

"We are going to start you in the study hall rotation. You should have a peaceful day. If you see some of the bigger kids sleeping at their desks, my suggestion is, don't wake them up. That may seem strange but no need to rock the boat. Your last period are the students who did not graduate, they are 18 years old and at the end of this track they get another shot at the graduation exam. If they don't pass they just get a diploma based on attendance."

Winding down, Dr. Gobi said, "I'll have Waldo Johnson show you to your room, he's our head maintenance man who doubles as a school warden. If you have any trouble with the kids just call down to my office and we'll send him up to help you out."

I sat outside the Principal's office on an uncomfortable wooden bench, assorted initials and profanities in several languages had been carved into it, in about seven minutes Waldo arrived. He was a huge black man, probably over three hundred pounds and about 6'2. Overweight? You would think so, his shirt had no chance at being tucked in. He walked me up to the third floor, room 305, and handed me a worn yellow key.

"Now don't forget to leave the key when you check out, the Principle gets really pissed if you don't return it. There is a cafeteria on the main floor and your lunch break is 5th period. There is a teacher's closed eating section at the back of the cafeteria, eat there. They don't like teachers mixing with the students."

"Thank you Sir," I was trying to make a good impression.

"Aw, lady, don't take this the wrong way but next time you come here you'd best wear a longer dress and a looser blouse."

"Thanks you for telling me."

" Well you should be ok today, just watch out for those older kids in the 7th Period," and with that he left, leaving the hall door with a small glass window, opened.

A bell rang and a sleepy bunch of students, little by little, trickled into the room and took their seats. I took the attendance roll fifteen minutes into the period. Most of the kids were well behaved. One girl asked me to look over her English composition, which I did, helping her to correct her misspelling and we rewrote a few of her awkward sentences as well. Then the bell rang, the kids filed out and in ten minutes the 2nd period started with a new group. "This will be a snap," I thought.

The hours passed slowly but aside for some students who conversed quietly, all went well. In the 4th Period I helped a stuttering boy answer the questions at the end of his History Book's chapter. I had lunch, met Mr. Rainy, the gym teacher who was a dream boat and a few catty hippy type woman teachers, who were not my cup of tea but I didn't staff the place.

After a low calorie cherry yogurt and a bottle of water, I really don't like to eat much for lunch, I went back up to my room. This 6th Period group seemed sleepy, no one asked for help. Finally Period 7 arrived, this time the kids looked older and tougher, only the first two rows were filled. But we got through the 45 minute hour without a problem and then the final bell rang.

"That's it for the day," I thought, "my first day." The room emptied out but five of the bigger guys were grouped at the back of the room talking. I called back to them, "Oh guys, the class is over --goodbye."

Instead of leaving they came up to me.

They seemed more like men, I asked them how old they were and they were all over eighteen, seems they'd failed the graduate record exam and were doing an extra year hoping they could graduate with a real diploma.

A tall muscular Latino kid picked up his books and started to leave, when he got to the door he pulled it closed.

"Please leave the door open for the other students. What is your name please?" I shouted to him, but he put his books on the desk nearest the door and walked over to me.

"My name me Carlos."

My eyes were focused on him, when he got within a few feet of me he slowly unzipped his fly and a very large cock flopped out, he shook it twice and it filled with blood and was erect.

"You like this teacher?" he slapped it hard on the table in front of me. It made a thumping sound.

I don't know what came over me but I reached out and held the firm cock in my hand.

"Oh yeah lady, I thought you'd go for it." Then he turned to the fellows from the back who were were now grouped around me.

"Come on guys, teach is going to play with us".

I had made the terrible mistake of being entranced by his huge cock, now I was going to pay for my error. A tall lanky student came up behind me, reached under my skirt, and in a second had pulled my pink panties with the little cat emblem down to my ankles. Momentarily I felt trapped, then I heard a snap, the flicker of a knife blade and I realized he must have slit my panties in two, because I now felt free, my legs were no longer trapped.

The boy with the big cock, that to my surprise I was still holding onto tightly, spun me around and bent me over the desk. He lifted my skirt and as I looked back I saw he'd unfastened the chain he wore around his neck,

"Oh I knew you had a pair of these, and with his hand he coarsely grabbed my balls and held them tightly,

"What a big pair of "cojones" the teacher has got," he said aloud. He wrapped his chain tightly around them.

"What are you doing?" Carlos was obviously separating my testicles from my cock as he tightly wound the chain around my balls and...

"I just make sure you don't go anywhere." he said as he tied the other end of the chain tightly to shank of the pencil sharpener that was screwed into the desk

He bent over and spit on my ass hole, "Nice and clean teacher."

"Thank you," I stupidly responded, thinking, "I always wash my ass with some damp toilet paper when I'm finished. He then spit into his palm and cradling the sputum he rubbed it on his cock,

"Wait Carlos," I shouted, wanting to tell him I had lubed condoms in my purse, but I didn't have a chance.

See Professorina, you no have a pussy so we gonna hafta fuck you in your sweet ass," and at that he smacked my ass very hard and for some reason, I started to twitch my ass, which must have sent the wrong signal.

"Wait Carlos!"

Oh no babe, I ain't going to wait, you don't really want me to wait to you do you?"

My libido must have taken over because at that moment, I shook my head, I was too carried away by the sheer sexuality of the moment and then he took my breath away when without any hesitation he thrust his cock head right up my ass as if he was shooting pool, his shaft took me by surprise and he didn't take long, within 30 second he grabbed my ass with both hand and shouted something in Spanish and he might as well have pissed inside me, his wet watery cum filled and spilled into me like a douche.

As Carlo pulled out, another student, I didn't know which one, replaced him, this cock was smaller and rode the cum load like a lube dose, he took longer and smacked my ass repeatedly. Carlos, who had just pulled out came around to the other side of the desk and stuffed his soft cock directly into my mouth. His dick hardened and to my surprise within another minute he shot another load deep down my throat but he kept pumping ever afterwards.

Just as I began to wonder if he would ever stop, he stepped back, his big cock bouncing off his thigh and another student lifted my head and pushed his fingers, that tasted like hot sauce, into my mouth. He was taller so he lifted my head by my blond hair, all the while his comrade kept slapping my ass as I tried to yell for him to stop. My head was now at the level of the cock of the hot sauce kid, he pulled out his fingers and thrust a cum crusty cock into my mouth.

There was no hesitation as he began pumping his dry penis hard into my mouth, he held my hair tightly in his fist. His dick was long and thin, the dried cum tasted sour and felt like sandpaper on the back of my throat. I tried to wet it with saliva as he ground it in and out of my lips.

"Can you taste it Lady," he said, "I jerked off this morning before I came to school, my Momina opened the bedroom door so I no have no time to wash it, but you Teacher, you do it for me."

I had no choice, nor could I answer as his cock was now so deep in my throat, then a hard shove from behind buried another dick into my butt hole, deeper than the one that was inside me before. I could feel whoever it was, quickly completed his rapid penetration, squirting a copious cum load inside me almost as soon as he reached bottom. Still eviscerating me, he was squeezing my tits very hard, timed with each pulsation of his cock, then he groaned and exited.

When he pulled his cock out of my ass, it was immediately replaced by still another student who slipped his dick in as smoothly as an Olympic baton pass. The crusty dick, still pumping away in my mouth all this time, finally barked a trickle of cum that I just let it drool out of my mouth, but no sooner was my mouth empty, then another fat red cock took its place.

Thankfully this penis was clean and I hate to admit it but it was just the kind of cock I always looked for when I was at the baths, about six or seven inches long and as thick as a half dollar. This guy took his time mouth fucking me as did the new guy in my ass, nether one was in a rush, after a few minutes of the old in and out, as if choreographed, they both came at almost the same time.

My blouse was open, my bra unhooked, my tits were sore from repeated squeezes, my nipples red and swollen. While those two were finishing up, a few new cocks materialized to find a warm place in my ass. Some of these dicks felt already familiar and I imagined they had fucked me earlier and had come back for second helpings and they took longer this time to cum.

While they busied themselves, the guy with the fat red cock, wiping his cock clean with my blond hair after spraying his jizz all over my face, leaned in so I could see his mustache and said, "You got nice tits Teach, next time I titty fuck you too." Then the room grew silent, finally the gang bang was over.

As I lay there, still bent over the wooden desk, I felt a cool breeze as the door opened, were there more to cum? No, the guys were gone but my balls were still chained to the pencil sharpener.

Through the door came heavy steps, it was Waldo, my savior.

"Oh Miss O'Day, Miss O'Day, Oh my God, what happened to you."

"Nothing Waldo, nothing, just some rambunctious students, just forget it." I didn't want this to go on my permanent record, if it did I never get another teaching job in the county.

"Just untie me Waldo, please"

His hands busied themselves and my balls were freed, but unexpectedly my rescuer had other thoughts in mind as he stuck his large finger, his fuck finger, right up my ass, his fingernail scratching me.

"Oh stop, your nail is hurting me."

Not surprisingly, without looking back, I realized what was about to happen and as he pulled out his finger he slipped in what felt like the biggest fattest cock I'd ever taken up my love canal. At the same time he cupped my tits, squeezing my nips and then grasped my hips and away he went; what I mean is, he really got down to business, the business of butt fucking, gyrating his cock like a whirly bird, scraping every part of the canyon. I couldn't help myself, I started to moan, to speak, to cry from the sheer joy of his love making,

"Oh, oh, oh, please , aww oh Waldo, be nice, oh Wald, oh yes Waldo and I felt a whoosh as if a rocket penetrated me. If I thought he'd put seven inches up my ass when he entered, I hadn't realized he still had four or five inches in reserve. A wild four or five minutes of his pleasure taking opened me up deeper than that one golden memory of Heinrich the German, the guy with the monster cock down at the bathhouse, but Waldo got much deeper and by the time he was done my asshole was so wide you could have stuffed a coke bottle inside and still have had room for a second prick.

Finally I could feel his vibrating cock as his dam burst, a flood, greater than any of the young men who'd defiled me in that last hour filled me completely. He was gentle even though he was huge. I could not help what I had held back when the boys were fucking me, maybe in part it was the chain around my balls, but I just could not stand it any more, I needed some relief, my muscles were stretched to the point of exhaustion and I just let it go. I came fiercely as Waldo's hot cum bathed me and my dick shot a load onto the side of the oak desk, leaking out over the table edge and inundating the corner of the roll book.

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