Ugly Duckling to Sissy Princess

I should have been grossed out by this. It should have made me want to vomit. But, instead, I wanted to taste her mouth.

Once inside her dorm room, I pushed her to the bed, and pushed her down on the bed. I grabbed both of her arms and I gave her a passionate and penetrating kiss. I tasted the cum in her mouth and savored it until no trace of it was left.

Why did I do such a disgusting thing? I don't know why! Was I curious about the taste of the cocks she was sucking? Or, was the crossdressing making me gay?

Then, I turned Carol over and pulled her ass up toward my groin. I lifted her skirt and tore off her panties. She screamed a little, but, I did not care.

For about ten minutes, I slapped her ass, pulled her hair, and pushed her face down on a pillow, while I fucked her as hard as I could with my little dick. I had never treated her like this.

I noticed she was breathing hard touching herself.

We both came!

Afterwards, Carol ran to take a shower.

When she came back, I was surprised to see a deep disappointment in her face. I did not understand.

"What is wrong?" I asked her.

"You have always been tender and sweet with me. But, just now, I felt like a piece a meat to you. Like you lost respect for me!" She explained.

"What? But, you finally came with me!" I exclaimed.

"I came, because, there is a dirty side to me that likes to be manhandled. But, you are my boyfriend. I want you to be tender and sweet with me. I want you to worship me like a princess." She explained with tears in her eyes.

She said, "I thought you understood my conflicting needs and I thought we had found the right balance to resolve it."

She continued, "If you treat me like the other guys do, then, I have no boyfriend left. All I have is a bunch of guys that like to treat me like a cheap piece of meat!"

"Whenever I begin to feel cheap, because of my uncontrollable urges, I know I can come to you to feel validated by your love and tenderness. But, right now, you just used me like all the others." She said crying.

I thought to myself - This chick is really fucked up!

I am so pathetic for putting up with all this bullshit!

I said to her trying to console her, "Alright, baby, okay. - I just slipped this time. It won't happen again. Only tenderness between us." I kissed her on the forehead.

The crisis was aborted. We went to breakfast as planned and everything was fine.

I continued crossdressing and thought a lot about the taste of cum. Why had tasting cum revved me up so fast? Was I just curious or was I really transforming into a girly boy?

I had to talk to Ted. He seemed to know a lot about weird stuff like this. I wanted to ask him if there was a way to reverse the transformation.

I went back to the bar. I did not find Ted, but, I got his number from a bartender.

The next day, after my last class, I dialed his number nervously with my hands shaking.

"Ted?" I asked.

"Yes, this is Ted." His voice said.

"Hi, this is James, we met at Nic's Bar in Bay Shore." I explained.

"James? I don't remember any James, sorry. You must have the wrong number." He said.

I was crushed that he did not remember me, but then, I heard him burst into laughter.

"I'm kidding, of course I remember you James, little man. Sorry I offended you." He said.

"No, don't worry about it. Actually - strange things have been happening since that night."

"Oh? Like what?" He asked.

I paused and took a deep breath. "I went out and bought an outfit and tried it on. I don't know why I did that. I've never had the inclination to do that. But, as much as I hate to admit it, you were right. I look hot and it was fun to dress up." I confessed.

I added, "But, I have to stop. I need to reverse this thing that is happening to me."

"I wish I could see you dolled up." He said, and this made me feel awkward. Was he flirting with me? I blushed.

He added, "Why would you want to reverse something that is fun? Don't buy into social programming and social conventions. You need to strip away every last vestige of homophobia left in you. If dressing feminine rocks your boat, surrender to it! Eroticism is a gift to cherish in whatever form it manifests itself."

"I cum harder wearing a skin tight mini dress, than, when I have sex with my girlfriend." I confessed. "That can become a problem for our relationship." I said.

He responded, "And she cums harder fucking big dumb jocks. So don't feel bad about that."

He had a point.

He said, "Listen, you are just beginning on this new path. When you discover how much more fun you can have, your mind will explode."

He continued speaking, "All the things that you hate about yourself, you just need to learn how to love them. You hate that you are a tiny boy with a tiny dick, - yet, in the world of crossdressing boys, you will be envied, because, you can wear sky-high heels. In the world of crossdressing sissy boys, a little dick is a treasure. Many boys use chastity devices to shrink their dicks."

"Ted, I don't know anything about the strange world you talk about, but, let me make one thing clear. I will never have sex with a man." I said.

I continued speaking, "If you are trying to talk me into this to make me your crossdressing bitch, that is not going to happen, ever!"

He laughed.

I explained, "I am a little curious about this crossdressing world you describe, but, that is it."

He said, "If you are wondering whether I have any ulterior motives with you - absolutely not. - Although, quite frankly, I would love to fuck you. - But, there is no agenda to lure you into my bed."

I was glad he could not see me blushing.

I asked, "So why all the pressure for me to crossdress and experiment with my sexuality?" I asked.

He explained, "Let's just say that I have unconventional urges myself and I know how painful life can be, until you sort it all out, and accept who you are. Also, one of my clients is the promoter of special parties that cater to crossdressing boys and the people who love them. Because so many young crossdressers are still in the closet, it is imperative to encourage every potential crossdresser I run into to join our parties."

He paused for a second, then, continued, "Listen, James, I have to go to a meeting now, but, speaking of parties, - we are having one on Friday. It will be invite only, at a very nice private estate. There will be boys like you, and they will be dolled up and looking gorgeous."

I asked him, "There will only be crossdressers at this party?"

He answered, "Um, no. Other guys will be there, but, they are very friendly and supportive."

I was curious, "Supportive? How are they supportive?"

He answered, "Well, the men encourage the boys to dress up. Some of the men will buy the boys sexy outfits and help them with money, and work, and other things like that. Sometimes, they form sexual relationships, but, only if that is mutually desired."

I said suspiciously, "That sounds like prostitution or like a sugar daddy relationship."

He replied, "Well, sure, there may be some sugar daddy relationships, but, they are entirely consentual and mutually pleasurable. Nobody is coerced into anything."

I thought to myself - Oh my God! - I just wanted to chat with Ted, but, he was already inviting me to some crossdressing party! He was already trying to pull me into a parallel universe. Things were happening too fast!

I wanted to say no to him, but, the truth was that I was very intrigued and very curious.

I thought to myself - maybe I could visit this strange new world one time. - What harm could come of it? I was very curious to see what such a world was like - a world where tiny boys with tiny cocks were objects of beauty and desire, - and, a world where dressing up like a girl was supported.

"Well James, are you interested, or not?" Ted asked.

He discerned my internal conflict.

He said, "Why fight it, James. You just want to have some fun dressing up, not kill anyone. Listen, you called me for a reason. You are curious. I am giving you the chance to discover something new and exciting."

He was very persistent, "James, for one night, you will be like Cinderella. - Not the inadequate and pathetic cuckold whose girlfriend is sucking and riding other cocks. - No sir, You will be a young, gorgeous and mysterious girly crossdresser that turns all the heads and captivates everyones' attention!"

I giggled and said, "I think you are over-selling it. - Yeah, I look a little pretty in a dress, but, spare me the heavy load of bullshit!"

He laughed.

He continued to pitch his party, "Seriously, James, it is a night that you will feel very sexy and desirable. SO WHAT, if the attention comes from men? - Minor detail. - You will be flattered none the less, and, you are under no obligation to do anything you don't want to do."

He gave his final pitch, "I promise it will be a lot of fun and a very safe environment."

I finally yielded, "Okay, as long as you stay with me the whole time. I don't want to be sitting alone, not knowing anyone there."

He sounded excited, "Great! I will pick you up at Nic's Bar at 7pm on Friday. That gives us a few hours to shop at some friendly stores, and, you will get your make-up done, and everything, to look absolutely sexy and stunning! It's all on me." He said.

Thank God he could not see me blushing.

"Um, okay. See you Friday." I said and hung up.

Oh my God! This was surreal! What had I gotten myself into?

I felt like the world was spinning. I was both nervous and excited!