tagTranssexuals & CrossdressersMale or Shemale, Still a Slut

Male or Shemale, Still a Slut

byyeaimbored©

So this is a 2 part story. Part 2 is strictly shemale and takes place a few years after Part 1. Part 1 is how Brandon became Brenda, although without the "I took bath and did my nails and shaved" stuff because that's not my thing. It's more tranny sex than anything, so if you're only looking for full on shemale skip to Part 2, they're pretty much standalone stories, I just wanted to submit them together as they are linear and use the same characters. As always, feedback is greatly appreciated, positive or negative!



Part 1

My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond of anal, so some of the guys were more than happy to take care of me. Most of the guys actually. The fact that my schools nickname was "bi-high" means I was never left without a dick to suck or (much more rarely) a pussy to fuck.

It wasn't just the students who were "fond" of me. My english teacher, Mr. Roberts, took a liking to me as well. He always stared at me during class, to the point that I swear he was eye fucking me. I actually really enjoyed his attention. It got me better grades, and he was pretty damn attractive. Mr. Roberts was an ex-marine and definitely kept in shape. Despite our mutual attraction, I doubt that anything would have come of it if he hadn't walked in on me blowing another student in the stairwell.

It was about halfway through the second semester of my senior year, and things were really winding down. I didn't have much work to do, and I did only a small portion of the work I was assigned. As such, I had quite a bit of free time. On the day in question, I was making use of that free time to earn a bit of extra cash doing what I do best: sucking and fucking. That found me on my knees in a stairwell cause the football team captain was unable to wait to get home and blow his load.

Right as the captain was about to blow his load, Mr. Roberts walked in and saw us. The captain pulled out and busted across my face as he hurried to put his dick away. He damn near sprinted out of the stairwell, hoping Mr. Roberts hadn't seen him. I wasn't so lucky. "Well well, interesting situation we have here, Brandon." Mr. Roberts said as I tried to wipe the cum off my face.

"Well sir, I can explain..." I replied.

"No need, I've seen all I need to," he interrupted me with, "You have detention with me tomorrow after school. 3 PM, don't be late." With that he left me trying to wipe the cum off my face.

I wish I could say I spent the next day dreading detention, or that I felt guilty, or something along those lines. But I can't. I assumed I'd go in and sit there for a while and Mr. Roberts would think about fucking me. I was wrong. I walked into Mr. Roberts' room to find it empty, until the door swung shut behind me and I spun around to find Mr. Roberts stroking a rapidly hardening cock.

I would have yelled if it weren't for two things: 1) I was almost hypnotized by his large cock, definitely bigger than anything I'd ever seen, and 2) our school cancelled band the year before, and Mr. Roberts ended up with the old band room. The sound proofed band room. "Both of us know that you aren't sorry for your actions and that no amount of detention will make you sorry. I figured we could both enjoy this time. So, why don't you drop down into the position I found you in and get to work?"

Before I could reply he put both his hands on my shoulders and forced me to my knees. I think I was still in shock a bit, because I did what he asked and grabbed his dick and began to stroke it. Soon it was it's full length, easily 8" and thick. He put his hands on the back of my head and guided it into my mouth. The instincts I'd been honing the last few years took over and I began to suck his dick like a pro. He let out a bit of a moan as I began to flit my tongue over his cock, enjoying the copious amounts of pre-cum leaking out. It was obvious he'd been looking forward to this.

In no time at all, or so it seemed, I could feel his cock begin to throb in my mouth. He began to shoot load after load into my throat, although it was definitely more than I could swallow and it began to spill out and down my chin.

"Clothes off, bitch," He said as he withdrew his cock from my mouth.

"Yes sir" I replied, removing my clothes as he walked over to the cabinet at the side of the room. To my confusion, he withdrew some clothes and began tossing them to me. I looked down at them and realized they were women's clothes, slutty ones at that.

"I'm gonna fuck you, but I don't want you looking like a guy when I do. You're going full bitch today. Put that shit on." He ordered me.

I hate to admit it, but that turned me on more than anything had before. As my cock sprang to life I began putting on the clothes he'd thrown to me. I realized that it was one of the girls cheerleading outfits. To my surprise, it fit me perfectly. There weren't, of course, panties to go along with the outfit, but I tucked my boner up so it didn't make my skirt stick out.

"Damn, you look even better than you did before! Now bend over my desk, I'm gonna make you regret being such a slut in public." I bent over his desk as ordered and as I did I noticed a mirror placed so I could see him fuck me. I got a good look at myself as I bent over and had to acknowledge that if I had tits (I had one of those haircuts that could be for a guy or girl) I'd fool even myself!

I was jerked out of my reverie as Mr. Roberts slapped my ass and flipped my skirt up. He poured some lube he grabbed out of his desk onto two his fingers and began to push them into my ass. I think he was surprised at how easily they entered because he soon added a third, then a fourth. It was definitely not my first time getting it in the ass, so I was more than ready for his fingers.

Soon enough he withdrew his fingers and pushed his cock into my ass. Between my spit on his cock and the lube in my ass, it entered without too much trouble, even with his rather impressive girth. Soon he bottomed out and I felt his balls slap against mine. He stayed like that for a minute, enjoying the view of his large cock splitting the ass of his student. I, too, was enjoying the full feeling his huge cock was giving me.

After a minute or two, he began to fuck me using full, deep strokes. His balls slapped against mine every time he pushed into my ass. I was really happy we were in the band room, because I think my moans just about rivaled the band in volume. He fucked me over his desk for a few minutes, then sat back into his chair, pulling me with him. I knew what he wanted and began to ride up and down on his cock.

"Oh yes Mr. Roberts!!!" I moaned, "Fuck me! Fuck your students tight little cheerleader ass!" This must have sent him over the edge because he grabbed me and forced me the whole way down onto his cock. I could feel it throb inside of me as he began to shoot his load deep in my ass. I thought the load he blew in my mouth was big, but this eclipsed even that! I felt his cum begin to squirt out of my ass around his cock.

Incredibly, he was still hard! He waited a few minutes (with his throbbing cock still in my ass) but then began to fuck me again! This time he picked me up, spun me around on his cock, and put me back on his desk, but on my back. As he fucked me, he used his fingers to scoop up some of the cum that had squirted out of my ass and made me lick them off. I was horny enough and he was fucking my ass well enough that cum began to dribble out of my cock, down the back of it and my balls, and onto his cock. This acted as more lube and allowed him to fuck me even harder and faster.

By this time, I was basically just constantly moaning. None of the cocks I'd sucked or fucked during high school came close to the size and stamina of Mr. Roberts. I was in cock heaven. The addition of the cheerleading outfit was just the cherry on top. Right there, as Mr. Roberts exploded into my ass for the second time, I knew that I wanted to be a slut. I wanted to dress like a slut and take cock like a slut. It was what I was made for.

Part 2

3 years later

High school was fun and all, but I had no idea how much better it would be after. I'm sure I'll tell more stories about my life immediately after high school some other time, but I wanted to skip ahead to something more recent. It turns out that Mr. Roberts (or Derek as I've come to know him) is a millionaire! Apparently a few years ago he won the lottery, then started teaching cause he got too bored. Thanks to his rather large fortune, and his fondness for me, I've been doing whatever I please since high school.

Immediately after I graduated I moved to a different town across the country with Derek. I'm not going to spout some classic nonsense about how we were in love or anything like that. No, quite simply I was his slut, and he was my "sugar daddy". Once we moved, he payed to turn me into a real girl. Well almost. I still have a cock, but thats the only way you can tell I used to be a guy.

My hair (now blonde, Derek likes blondes) is down past my shoulders. My butt, which was decent before, is now one fine looking round ass that regularly draws stares. Well the stares that aren't directed at my amazing 34DD tits. I also had the little body hair I had laser removed. Long story short: I'm a god damn shemale bombshell.

In return for paying for all that, I'm at Derek's beck and call 24/7, and I love it. His cock is still amazing to me, although it's far from the only one I see. He's changed professions and is using his lottery winnings to start a business. He often uses me as a bargaining chip when he is negotiating business deals. The first was a few months ago...

I was completely set in my role as a shemale. I slept in Derek's bed at night and we often fucked for a good part of the night. This night, however, was different. He left me pretty much alone, only saying that he had a surprise for me the next day. I was excited to say the least, I almost always enjoyed his "surprises".

I accompanied Derek to work the next day, I often helped as a sort of private secretary for him. As usual I was wearing something revealing and completely unfit for an office environment. I had on a very short gray skirt, black fishnets, high black heels, a gray jacket, a white blouse with an extra button unbuttoned and a matching set of a lacy bra and black thong.

When we got to the building I drew the same appreciative stares I always did. I'd fucked most of the guys in the office (Derek also used me as a sort of prize) and they all knew about my extra "equipment". I was just young enough and hot enough that none of them cared. When we got back to Derek's private office, I went and sat at my desk, knowing if he wanted anything he'd come ask.

Sure enough, a few hours later Derek called me into the conference room. Assembled there were 5 men from the board of Derek's biggest competitor. I knew Derek had been trying to push a deal with them, but he also said they were driving a hard bargain. It seemed I was there to sweeten the deal.

"Brenda [my new name], these men have been working with me all morning. I think they deserve a bit of a break, don't you?" Derek asked.

"Why of course Derek, I'd be more than happy to provide them with anything they need," I replied with a wink. As I looked around I could tell that most of the men had boners already. These were the new breed of business owners: young, fit, and good looking. Horny too, by the looks on their faces.

"And with that, I have some work to get done. I hope you all enjoy your 'break.'" Derek said as he walked out of the room. For about half a second after the door closed the room was completely still, then there was a flurry of movement as they surrounded me and began stripping, their clothes and mine. Thankfully Derek must have warned them about my package, because nobody gave it any second thought.

I immediately got down onto my knees and began blowing the men. I tried to keep it even, constantly rotating between cocks, but it was a lot to take care of, even for me. The ones that weren't getting sucked or jerked off would slap or finger my ass, or squeeze my nipples. Sometimes it got a little rough, but I just began to blow the rough one and he'd settle down. One of the guys, a geek by the looks of him, blew his load into my mouth the second time I put it in. He stepped back from the group, but I was sure he'd come back for more.

It didn't take long for the other guys to realize I had another hole they weren't using. I was promptly bent over the couch in the back of the room (a couch that had been brought in expressly for this purpose I realized) and had my legs spread. I'd worked my ass out and lubed it up before leaving the house that morning due to Derek's warning of a "surprise". I was thankful for that because the first guy didn't even finger me. He just slammed his cock right in.

"Damn this bitches ass feels nice!" He exclaimed as he began to fuck me. He definitely didn't have the biggest cock, so I wasn't even getting much pleasure out of it. I could feel his cock begin to throb, but before he came he pulled out. "Not gonna cum too soon" he said.

Another cock that was pretty much the same size soon replaced his. On second thought, I realized it was actually the exact same size. I looked back and thought I was seeing double. There were twins!! Twin two began to fuck my ass, although at a much faster pace than Twin one. I didn't have time to reflect on it for long because a much larger cock was begging for my attention. The guy in front of me began to face fuck me. I gagged on his cock as he slammed it into my throat. The fourth guy still hard (other than the geek) guided my hand to his cock which I began to jerk off.

Twin two did much the same thing twin one did, and pulled out immediately before he came. The guy that I was jerking off moved to my ass as the big one continued to fuck my throat. "mole" as I was thinking of him (due to a mole next to his cock) didn't seem like he'd last long. Less than a minute into fucking my ass he began slapping my ass and groping my tits and before too much longer he began to spray the inside of my ass with its first load of the day. He pulled out, and before I had time to do anything "the big one" moved from my mouth to my ass. I could tell from blowing him that he was bigger than Derek and Derek was the biggest I'd ever had, so this would be interesting.

As "the big one" began to push his huge cock against my little ass I realized just how much bigger he was! Even with the three poundings my ass had already received it was still not loose enough. Not caring how it felt for me he began to force it into my hot shemale ass. I moaned, loud, as the head popped into my asshole. I wanted to tell him to wait, but knew it would do no good.

Sure enough he immediately began to force it deeper into my ass. I began to hyperventilate the feeling was so intense. Soon though, my ass relaxed enough that he was able to begin to fuck me properly. Not only did he have a big cock, but DAMN did he have stamina. He was still fucking me when the twins had cooled enough to have me blow them.

After a few minutes of alternating between the two of them, one had the idea to flip me over on my back and fuck me on the conference table. "The big one" was still in my ass, but now one of the twins was titty fucking me while I continued to blow the other. Once again, the twins nearly blew their respective loads, but stopped. Again, it was just me and "the big one".

All the sudden, without warning, he began to pick up the pace even more. He reached down and squeezed my tits HARD as he began shooting cum deep into my ass. It felt like he came forever, it just kept flooding my ass. Finally, however, he stopped. His cock began to soften and shrink, then finally popped out of my ass.

The twins were still cooling off, and there was a slight lull in the fucking. All of the sudden, "the geek" was on his hands and knees in front of me, asking to get fucked. Now I love anal, but I really don't like giving it. Not to guys anyways. They're only there for their dicks. But I told Derek I'd do whatever these guys told me to, so I got down and started rimming the geeks ass. While I was rimming him, "mole" came up behind me and slid his cock into my ass. After "the big one", "mole"'s cock was absolutely nothing. I began to finger the geek's ass, and was surprised to find it a little loose. It seemed someone was a switch hitter.

One of the twins handed me lube and I used it on the geek's ass and my cock. Somehow through all the hormone therapies my cock had remained a respectable (for a shemale) 6". I began to feed all 6" into the geek's ass as I was fucked in my own ass by "mole". We continued like this, with "mole" setting the pace for everyone's fucking until I felt mole begin to tense up. I reached around and began to jerk the geek off so that both him and "mole" came at almost the exact same time. The geek crawled away from me as "mole" pulled out of my ass and forced me to lick the geeks cum up off the floor.

After I licked the cum up I looked up and saw one of the twins laying on the conference table. He beckoned for me to get onto his cock, so I did, of course. I got into the classic cow girl position with my DD tits hanging down into his face and his cock up my well lubricated (with cum) ass. No sooner had I leaned down than I felt another cock at my ass. I knew almost instantly that it was his twins. "Take it slut!" he said as he began to force his cock into my ass alongside his brothers.

"Yeah, take it!" His brother echoed. I felt more full than I ever had before. My ass was screaming in pain/pleasure. After slowly working it in, the twins got their cocks as far as possible into my ass and let them sit there for a few moments. With that I'd done one of the things I'd never thought I'd be able to do as a shemale, have a true dp.

I didn't have long to enjoy my moment, however. The twins were desperate to get their rocks off and began to fuck in and out at the exact same pace. They say twins have some sort of connection or something, and these two must have. After a few minutes of fucking they began to cum in sync with each other, double filling my not so tight hole.

After pulling out, "the big one" brought a champagne glass over and put it under my ass. He had me push all the loads that had been blown into my ass out and into the champagne glass. After getting as much out as I possibly could he had me lay down on the floor next to the couch on my back and put my ass onto the couch. Then he had me open my mouth and poured the cum into it, but wouldn't let me swallow. I could taste my ass in the cum, and honestly, it tasted pretty good.

"Listen up, I want you to hold those loads in your mouth while you jerk off. When you cum, lift your legs up and cum onto your face and into your mouth. Once you scoop all your cum into your mouth, then you can swallow." "the big one" ordered me.

I did as he asked and began to jerk myself off. While I jerked off, "the big one" fingered my ass and the geek began to slap my tits and pinch my nipples. With all the attention, it didn't take long for me to begin to cum one of the biggest loads I've had in my life. I completely covered my own face with my cum and began scooping it into my mouth. When my face was clean I showed all the guys their loads and then swallowed.

The men then allowed me to get dressed again, and I walked out. Derek was waiting outside with a smile on his face.




I'm not sure whether or not I will continue this story at all, and if I do whether it will continue in two parts like this or just add on to one part or the other. Let me know what you all think! As always your feedback is most welcome and enjoyed. Oh and if you have any ideas you'd like to see, or any fantasies you'd like to hash out, send me a message!

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