tagTransgender & CrossdressersA Surprising Change

A Surprising Change


This all started several years ago, as I finally turned 18 years old. That was when I discovered it, and it completely turned my life around.

I had graduated high school the previous spring and my birthday was the first weekend after I moved into college. Now it's safe to say I wasn't the most popular kid in my high school. Fuck, I don't think anyone anywhere was less popular than me.

I was just under 5 foot 2, with no muscle, a slim frame, no athletic ability, my grades were just ok, and I had absolutely no friends. Literally not even one. I was so unpopular that I didn't even get bullied cause the bullies didn't know I existed.

So even though I didn't get into my dream school, I was pretty happy to get in somewhere with a half decent scholarship so I could move forward with my life. And that takes us to the beginning of the real story.

As I mentioned, it was my 18th birthday, just a week after I started school. Already my life was totally different. I was living away from home for the first time. I had already made a bunch of good friends, especially my roommate, Jamal. As a 6 foot 5, extremely dark-skinned African American basketball and football star, we could have been more different, but still it was like we were destined to be friends.

I even had a girl I was getting to know. She lived a floor below me and I met her by accident when I was moving in. I got off the elevator of our building on the wrong floor and showed up to her room instead of mine, she being in 415 and me in 515. Her name was Lisa and she was incredible. She was thin, but with an extremely curvy, tan body, long black hair and an absolutely gorgeous face. Plus at 5 feet flat she was shorter than even me!

So yea, life was good. For my birthday, Jamal said he could get me into the basketball team's party, which I was thrilled about, so around 11 that night we finished pregaming and made our way there. It was awesome. I had been there for an hour and every time someone heard it was my birthday they handed me another drink. I was beyond drunk.

Then I received a text from Lisa asking if I wanted to come to another party she was at. I don't think I've left anywhere faster. The party was only 3 or 4 minutes walking from where I was and I made it in less than 2.

I quickly found Lisa and we spent the rest of the party together. I couldn't have been happier in that moment, or so I thought. Around 2 she asked me if I wanted to go back to her dorm because she had to give me a very special birthday present.

I tried my best to play it cool but I could tell she saw right through it. We left and headed back to her place. As soon as the door of her room closed she pushed me back on her bed and dropped to her knees in front of me. I really couldn't believe this was happening! One of the most beautiful girls I'd ever met, on her knees in front of me! It was a dream come true!

Then I realized something. Even with all this going on, I wasn't even a little hard yet, and my fears continued when she took me in her mouth and still nothing happened. It was a nightmare. This goddess-looking women taking my cock in her mouth, the first time any girl at all has even given me a little attention, and I'm too drunk for an erection. After another 30 seconds or so she seemed to realize.

It was strange though. She didn't seem upset or disappointed though, but I played it off to me being self conscious. Let's be honest, this was probably the first time a guy WASN'T hard just being inter presence. But she sat next to me on the bed and began to comfort me. After her holding me for a few minutes she told me she could finish with my present tomorrow and I began to feel less embarrassed.

About 20 minutes after that she asked if it was ok if she went to take a quick shower. She said I could hang out in her room and spend the night since her roommate was gone for the weekend, and I didn't really feel like going back to my place that night so I said yea.

She faced away from me, slowly and teasingly stripped off everything except her panties, allowing me to fantasize over every curve of her body, then threw on a robe before I could get a glimpse of anything else. Next, she slowly removed the panties from below her robe and did that coy little thing girls do where they have their panties on one finger while they playfully bite their finger on the other hand. She then let the panties drop and my eyes followed them to the ground. As they were falling she left for the bathroom and I heard her say she'd be back soon.

And that was when it happened. To this day, I still can't tell you what made me do it, but as soon as the door closed I knew I had to.

Without even thinking, my body just acting on its own, I went to the panties, picked them up and sniffed. It was incredible. The smell was unbelievable, and without any thought, I had to put them on. They were pink lace boy shorts, with a little pink bow on the front. As soon as they were up and around my waist, my cock sprung to action and I was rock hard. I was amazed. 25 minutes ago I couldn't get an erection with a beautiful girls lips wrapped around my cock, but here I was, rock hard from wearing panties.

And then I heard the door slam shut.

"I fucking knew it!" Lisa said.

I spun around, and covered my crotch as if that was gonna hide anything.

"Lisa it's not what it looks like! Its-"

"It's exactly what it looks like! The second I laid eyes on you I knew you were a little sissy bitch! Did you really think a girl as hot as me would really be interested in a loser like you? Look at yourself! You couldn't get an erection with this sexy mouth sucking that little dicklet off but throw on some women's undies and it's harder than diamond!"

I was completely at a loss for words. I stood there, stammering, trying to think of anything to say in my defense, but she beat me to it.

"This is what's gonna happen. You're gonna do every last thing I tell you to do, no matter how uncomfortable or degrading it may seem, and you won't say no to a fucking thing. As long as you do that, I won't take the video that's recording even as we speak to any family and friends, the dean of the university as well as the police. What do you say bitch?"

"Ye- yea, ok Lisa," I stammered out. All I was thinking was how the fuck did this get here? From me receiving a blowjob to me being blackmailed by the same girl while standing there in her panties.

"No, I'm not Lisa to you anymore. You will call me Mistress from now on as well as any of my female friends when they're here. For my male friends, they will be Master to you. Understand bitch?"

"Yes Mistress."

"Good bitch. I'll go through all the rules with you later but for now you need to be punished. Get down on the floor on all fours bitch."

I didn't know what else to do so I just obeyed. Without another word, she straddled over me facing towards my ass and proceeded to begin spanking me. Not the fun, sexual type of spanking, but hard thwacks that made me lurch forward and whimper in pain. Counting out loud, she went until she reached 50 on each cheek. When she was done I had tears running down my face and my ass was on fire. I knew I'd struggle to sit for at least a few days after this sort of abuse.

"Good bitch. Now for part 2 of your punishment. Keep looking forward. And don't even think about turning around."

After the first part of the punishment, I had absolutely no intention of doing anything that would upset her so I stared straight down at the floor, trying to control my sobs. I heard her rummaging through a drawer behind me and heard the loud thump of something being put on her desk behind me. Next thing I knew I felt a blindfold pulled over my eyes and my world went black.

Then a moment later she pulled her panties down around my knees and I heard her door open and close. "Mistress?" I said, "Mistress are you there?"

No response. My first reaction was to remove the blindfold and see if she actually left but I realized that's exactly what she would want me to do. Either she was still in the room watching how I'd act or she'd watch the video she said she's recording later to make sure I didn't move, so I stayed put.

After what felt like an hour, although it was probably only a few minutes, I finally had my answer, as I felt what had to be the biggest dildo ever, although looking back now it probably wasn't half as big as some I've experienced since, penetrate me at full force. No penetration, no warning, just a massive rubber dong shoved balls deep into my asshole as hard as my little Mistress could push, which believe me, was very hard for someone her size.

I began to cry out in pain but immediately I felt her hand cover my mouth and muffle my screams. She began slowly, methodically pistoning the dildo in and out of me while she whispered softly in my ear, "That's a good little bitch. Take Mistress's cock all the way to the balls like the good little slut you are."

At this point all the pain I had felt had evaporated and was replaced with a deep sense of pleasure I could feel spreading through my groin. I even heard myself begin to moan from how good it felt. As she pulled her hand away I heard my moans become even louder and I noticed they even sounded a bit girly.

"You love taking my cock don't you bitch? Tell me how much you love it."

"I love your cock Mistress! It feels so good fucking my asshole!"

"No bitch, that isn't an asshole anymore. That's a sissypussy now and it's made for taking cocks. Understand bitch?"

"Yes Mistress. Please keep fucking my sissy pussy. It's yours forever to use as you want." I moaned

"And anyone else I want to share it with too?" she asked.

"Yes Mistresses! Anyone at all!"

"Do you want me to tie you down over my desk bitch? Then I can really fuck you with this cock good."

"Yes Mistress please!"

I felt her grab me by the hair on the back of my head, bring me to my feet, and throw me over the desk. Then my hands and legs were bound down and I couldn't move, not like I wanted to.

A moment later and she was back in me, and this time it was even better. She was hitting pleasure spots I never knew could exist in a human body, the whole time telling me what a disgusting slut I was, how this was all I was good for, and it only made me more excited. After another few minutes I felt uncontrollable pleasure course through my groin as I sprayed my load all over the side of her desk. Immediately after I felt the cock plop out of me and it was like an emptiness, not having that feeling there.

Before I could dwell on it too long the blindfold was ripped off my face and I was met with Mistresses's phone inches from my face recording a video.

"How did you like that whore? It feel good to be fucked like the little bitch you were always meant to be?"

"Yes Mistress. I see now that my true place is to serve you and everyone else."

"I need you to prove it to me in one final way," she said with a smirk, "I want you to clean the mess you made on my desk with your tongue."

"Yes Mistress, whatever pleases you." The scariest part of her request to me was that it didn't scare me at all. In fact, it seemed natural that I should do that. She undid my restraints and I dropped to me knees and cleaned every last drop while my Mistress proceeded to film the whole thing.

When it was done I saw her stop recording and waited patiently on my knees while she did several things on her phone. Then she sat down and motioned for me to kneel in front of her.

"It's time to tell you the truth slut. I didn't know the first time I saw you that you were a sissy bitch like I said. In fact I thought you were cute and seemed like a nice genuine guy. My full intention tonight was to bring you back here, have sex with you, and then see where it went from there. Everything was like you thought until I went to go take a shower.

"Then when I came back was when things started taking a different course. I had actually just forgotten to take my towel, noting more. But when I saw you in my panties I realized you were just another pervy asshole guy and I decided to take advantage of it. I had no video of you trying them on, and nothing to prove you did. It would have been your word against mine. I intended to punish you with the spanking and then punish you further by fucking your ass with my dildo. I never imagined you'd actually enjoy that though. I'm glad I decided to video tape the whole thing starting from just before that. I didn't have any blackmail before but I sure as hell do now. And this one's even worse cause you literally fucking beg me for it. So back to what I said earlier. You do whatever the fuck I want you to whenever the fuck I want you to and I don't show that to the whole world. Tomorrow morning you will receive an email from me with more information about your new life and you will follow every rule to the letter or you will be severely punished. Now get the fuck out of my room bitch."

With that she slapped me across the face as hard as she could. I grabbed my clothes, too afraid to even put them on before I left lest she share that video, and bolted out the door. Thankfully it was still 5 am so no one else was awake. I made my way up to my room, wondering what the hell I'd gotten myself into, and fell asleep from sheer exhaustion before my head even touched the pillow.


Note: I have ideas for following chapters that I have yet to write. If you enjoyed the story let me know and I'll continue it further. If you have any criticisms I want to hear them as well so please comment them (without being mean about it of course!!)

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bychrissycockslut© 4 comments/ 20821 views/ 14 favorites

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by Anonymous

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Confusing and disorganized

This story was interesting to read, but I found it confusing, disorganized, and unbelievable. It seemed more like a first draft than a finished product. There was nothing leading up to the revelation aboutmore...

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by Anonymous07/08/18

good start...

this is a good start...when you took the time to introduce Jamal...I was hoping the story was going in his direction...maybe another chapter is forthcoming starring him...I hope...

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by Artificial_Int07/08/18

Hello there

My voting was 4/5 bcs of mistress not master. Maybe in next part.... Smirk

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by Anonymous07/08/18

To short

Was way to short. Needed much more action and a deeper description of characters

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