Ego Vs. Desire: A Sissy Transformation

Part 1

I wasn't always like this. Growing up I was always attracted to girls. Sure, there were some moments with friends, but that was just part of puberty and growing up, right? It's hard to really put a finger on when things actually took a turn, but it's safe to say that they did.

I'd tell you my name but it doesn't really matter at this point, that person is gone. I no longer have a name. Don't get me wrong, I am called a lot of things; sissy, bitch, pussyboy, snowbunny, and whatever else my masters feel are appropriate at the time; however, I can at least tell you what I look like. I'm a 20 year old, 5'4", white sissy, which is about 120lbs, with long dark hair that has been dyed blonde. Oh, and brown eyes. I've been told that I have a bubble butt, and despite what the internet says I have a below average size penis of just below 5 inches.

This entry will be the first of a number of instances in my life. Since this is the first I suppose it makes most sense sharing how I first met my masters.

Being a single 18 year old can be frustrating. Being a single 18 year old who was a kissless virgin is even worse. I tried talking to girls in high school. I tried talking to girls on facebook, tinder, and instagram. I even tried joining those dating sites. It didn't matter. No matter how many times I messaged I never got a response back. I wasn't bad looking either. I was actually a pretty good looking guy to be honest. The only thing I could think of was my height. Girls like to say guys are shallow, but how many girls want to be with someone shorter than them? At 5'4" the female options were limited and even then the girls shorter than me all wanted someone around 6 feet. My standards began to go lower and lower and lower.

I was desperate.

I was so frustrated I started copying and pasting the same message to every girl I saw on my dating site. I didn't even care what they looked like. I just wanted to see who would actually respond. I spent what must have been 2 hours doing this, and then sat for another couple waiting for a response. Finally, just as I was about to call it quits and go to sleep a new message was received. I couldn't believe it. I was almost scared to look, but I clicked on the new message and began to read:

"Hey, what's up? You're kinda cute :)"

Before responding I clicked on her profile to look at her pictures....annnd she was perfect! She was short like me, very petite, pretty green eyes and blonde hair. I couldn't believe it. I immediatly replied back and Gianna and I talked back and forth the rest of the night.

After a few weeks of getting to know each other we finally made a date to meet. I was going to pick her up at her house and then go grab some food and maybe a movie. These dates went on for a few more weeks and things were really taking off. I of course wanted to have sex with her and she knew it but she said it was too soon and I didn't want to fuck up a good thing so I didn't pursue it too much, until finally she asked me if I wanted to go with her to watch over her uncle's cottage a few states over. We'd be there the whole week with zero TV or internet. The only thing there really would be to do is have sex, and she knew that too. It was basically implied that this is what that trip would be about, so of course I went on board. I took a week off from work and made preparations for our little get away.

The day finally came to leave. I mean this was it. I finally had a girlfriend and I was finally going to lose my virginity. Gia told me that she didn't care that I was virgin and that she didn't want me to jerk off for at least 3 days leading up to it. She wanted me to feel amazing and didn't want me to feel ashamed if I came too soon. I was so comfortable with her, I actually decided to not cum for the entire week. My balls were aching by the time Friday came along. I'm used to cumming at least once a day, so this was torture, but I knew it would be worth it. I loved this girl and she loved me, plus we had the whole week for me to prove to her how much of a man I could be for her.

Upon our arrival I was so excited that I almost came in my pants walking to the door. Once inside she wasted no time. She grabbed me by my belt and pulled me into the master bedroom. She pushed me to the bed and began to remove my clothes. Once naked she started at my feet and kissed and licked her way up to my balls. She took a deep breath and "mmmm'd" to herself. I was has hard as diamonds as she began to lick and suck on my balls while gently stroking my penis with her hand. My balls were huge from not cumming in such a long time and so sensitive. Every stroke of her tongue sent waves of pleasure throughout my body. She plopped one of them into her mouth and sucked just hard enough to make it hurt a little bit, then she put the second one in and did the same. I was in heaven, but at this point my penis needed some serious attention and she must have sensed this because she began to lick the bottom of the shaft and make kisses all the way to the underside of the head. She sloppily kissed here and it drove me wild. I wanted to cum so badly but she wasn't giving me enough friction. She knew what she was doing.

At this point she got up and asked if she could tie me up. I obliged without even thinking. She pulled some of those frilly cuffs from her suitcase and attached my wrists and ankles to the bed posts before going back to working on my dick. She swirled her tongue around the head and pushed her mouth to my stomach. I could feel the start of the back of her throat as she held herself in this position till she couldn't hold her breath any longer gasping for air as she pulled away from my throbbing cock leaving what looked like gallons of spit behind. I felt like I was in a porno. I felt like the man. Maybe it took 18 years for this to happen, but it was worth the wait!

I was just about to cum but then she stopped and started to undress herself. She turned around and began to unbutton her blouse. She slipped it off the back of her arms revealing a tiny pink bra strap which she also let fall to the floor. She then unsnapped her jeans and dropped them to the floor while bending over showing off her beautiful pantied ass. She turned around slowly began to pull off her frilly panties to reveal a tiny little penis underneath.

I couldn't believe it. She's a he! How could this be? I didn't believe it. I didn't want to believe it. This couldn't be happening to me. Things were so perfect. I kissed this girl...or guy...I-I just had my first sexual experience with this person!

"What's the matter baby? You don't like it?" She asked while bouncing it in the air

I couldn't speak, I was at a loss of words.

"It's ok baby. I was scared at first too, but you will learn to like it just as I did. Now, you stay right there. I'll be right back."

She tapped the tip of my still hard penis and left the room. What the fuck was going on. What did she mean I'd learn to like it? How did I even get myself in this position in the first place? I should have known it was too good to be true. Fuck!

She was only gone for a moment before reentering the room but this time she wasn't alone. There was a huge black man following behind her. He must have been 6'5" and 240lbs, and ripped.

Gianna began to speak; "This is Daddy, baby. Don't be shy. He knows all about you and me. He's been with me helping me respond to your texts and online messages since that first night a few months ago that we messaged each other."

Just as I was about to protest, this black man interrupted.

"Shhhhh! Don't say anything. It's ok. I know you must be confused. No need to speak. Just listen," He said. "You don't know it yet, but you are mine and have been my little sissy for a long time, but I can't believe you don't recognize me."

As embarrassed and humiliated as I already was this was the icing on the cake. I know this person? I don't know this person at all...

"Here maybe this will remind you"

Gia then dropped to her knees and fished this man's huge black cock from out of his basketball shorts.

"Still nothing?," the man asked, "Gia."

All he had to say was her name and she began to stroke and suck on his cock. It didn't take long for him to get hard, but once it did my heart skipped a beat. I can't believe I'm admitting this - that I recognize a penis - but I did recognize him now. How could I ever forget a cock like that. This was Jamichael! I had chatted with this man on craigslist for a few weeks back when I was really horny. We talked about all sorts of things - things I am too ashamed to admit.

"Haha! I knew you would remember me. Now, don't be shy or scared. You know me. You know I'm not going to hurt you, and neither is little Gia over there. We had some pretty intense conversations a couple months back didn't we?"

I tried to play dumb and act like he had the wrong guy. I mean I never sent Jamichael photos of my face, he could have the wrong guy for all he knows.

"C'mon don't be like that. Here let me read some of my favorite quotes by you. See if you remember after that. Let's see where to start, hmmmmm, ah ok how about this. You don't remember saying this? C'mon man you gotta remember saying, "my penis is so small I sometimes wonder if I was supposed to be a girl" or "whenever I don't cum for a few days I start to really get turned on by the idea of sucking a black cock"

I began to turn beat red and at that moment he knew he had the right guy. I was fucked. In more ways than one. I didn't know what to do.

"Hey Gia, baby, you done good. What has it been? 3 days without cumming?"

He was asking ME that question. Oh my God. Gia specifically told me to not cum because of this very reason, and I blindly did what she said.

"Well? How long has it been girl?"

He was calling me girl!

*SMACK*

Jamichael slapped me across my face before demanding that I answer him.

"I-It's been s-seven days," I said through the start of some tears

*SMACK*

"Seven days, what, GIRL!"

"U-ug"

*SMACK SMACK*

"I'm a nice guy. You know this, so don't make me have to do this. You will address me with respect going forward, and that means you will address me in complete sentences and refer to me as Sir - for now anyways. Now, seven days, what?"

"I-I haven't came in seven days...sir"

"That's better, and even better than I expected. Seven days huh? I remember you telling me that it only took you two days without cumming before you started thinking about getting down on your knees and accepting a real cock into your mouth. How do you feel tonight baby? Do you feel like sucking a cock?"

I was still in shock and didn't know how to answer. Everything he said was actually very true. Even though I was straight I could not help but think about sucking cock, especially black ones for some reason, whenever I hadn't came in a couple days.

"Listen, I know you thought Gia was your girlfriend and everything, but let's get this straight right now. Gia is my girl. You are not having sex with her. She is not going to put your tiny pee pee in her mouth ever again. You are not going to put your tiny pee pee in her pussy. Gia is mine and off limits. So, if you're thinking about saving that nut for her just know it's not going to happen. So, I'll ask you again baby...

Jamichael started to stroke my still hard penis

...Do you feel like sucking a big. Juicy. Hard. Black. MANLY. Cock. Tonight?"

I mean technically this was one of my fantasies, and it didn't look like I was going to get lucky with Gia, not that I even could seeing as she didn't actually have a vagina to lose my virginity with anyway, but my brain wouldn't let me submit.

"I'm sorry Sir, but I do not think I can suck on your cock. I don't think it's something I can actually do."

"Well, suit yourself. I'll just have this sexy bitch do it"

Jamichael laid down next to me as Gia crawled from the end of the bed between his legs. She began doing the same number on him that she was doing to me not even 30 minutes ago. I was actually really hurt. I know that Gia wasn't who I thought she was, but I had real feelings for her and I felt like she was cheating on me with this asshole.

Gia continued sucking on Jamichaels cock as he smacked her face, pulled her hair, and called her all sorts of horrible names. Every now and then he would reach over and stroke my cock and now blue balls just to keep me on edge. As Jamichael was getting close to cumming he asked me one more time.

"Are you sure you don't want this cock baby? This stupid whore did most of the work, all you gotta do is open up and take your medicine."

"No sir, no thank you. I would not like to take my...m-medicine," I said almost inquisitively

"Yes, medicine. Don't stutter. Trust me bitch, it will make you feel better...in case you didn't realize already, you're not allowed to cum till you take mine baby. UGHHHHHHHHHHHH Fuckkkk, that's right you stupid fucking cock sucker. Take all that Daddy nut you bitch. Don't swallow it, I want you to show my new girl what Daddy did to you. Look at her bitch. Look what a real man gets."

Gia came over to my face and showed me her mouth full of his hot thick cum. She began to swirl it around in her mouth with her tongue.

"And to think you thought that would be your cum in that pretty little mouth tonight. Sorry baby, but there are two types of males in this world. Those who give cum and those who take it. Guess which one you are?"

Jamichael began to stroke my penis and asked me again

"Guess which one you are baby, guess."

I was going crazy, I needed to cum so badly and I couldn't help myself as I spit out the words

"Ugh..ahhh..I...ugh...I am...ffffuck...take..cum...please"

"Haha, I'll accept that as an answer little one, but remember, you don't get to cum at all until mine is in your mouth, and I'm done for tonight, so maybe we'll try again tomorrow."

Jamichael got up and headed for the door

"Swallow"

Gia swallowed Jamichaels heavy load and then got up and followed him out of the room turning the light off behind me.

So many different thoughts and emotions were running through my head, but all I could think about was my still hard penis pathetically sticking up toward the ceiling. I wanted to cum so badly but there was nothing I could do. I was no longer in control, and I wasn't sure that it was a bad thing.