Ugly Duckling to Sissy Princess

All names have been changed to protect the guilty.

*****

Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls.

I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful, sexy, sweet and I worshiped her, and treated her like a princess.

We lost our virginity to each other. I was always gentle and tender to her during our lovemaking.

She overlooked my shortcomings, because she appreciated my warmth, intelligence, respect for the dignity of women, and we had many intellectually stimulating conversations about art, politics, history, literature, philosophy and feminism - because, she was a feminist.

Carol was my beautiful angel - my pride and joy. Every day I held her in my arms felt like I had died and gone to heaven. Life was perfect.

And then, - heaven collapsed and turned into hell, the day she confessed her infidelities to me.

She tutored stupid jocks in biology, which was her major. There were many reasons why I would have never suspected that she would sleep with any of them. Sure, many girls are attracted to big, strong and athletic jocks, but, my Carol was different. She was an intellectual and a feminist. She was offended by the way most jocks treated women. She was attracted to smart men, like me, and the jocks were the antithesis of that.

But, most importantly of all, we were profoundly in love with each other. I trusted her 100%, because, it was inconceivable to me that she would betray my love.

When we celebrated our third year anniversary at Serranos, a fancy Latin restaurant, I notice that she was anxious and depressed, but, she would not tell me what was wrong.

When I brought her back to my dorm room after the restaurant, she told me to sit down, because she had something to tell me and it would not be good news.

"Are you breaking up with me? You are everything to me, Carol, how can you leave me?" I asked teary eyed.

She started crying and said, "No, baby, I would never leave you. It is you who are breaking up with me - after you hear what I have to tell you."

"That is ridiculous!" I protested.

"I need to tell you something, and then, you are going to dump me. - And, I deserve it." She explained wiping tears from her face.

She told me she was sick with guilt, and had to make a confession. She then confessed to having cheated on me with five jocks over the past year. She said she was extremely ashamed. She explained that she had uncontrollable sexual urges that had defeated her better judgment. She said she was not even attracted to them, but, that something sexual had ignited in her each time. She had succumbed to blasts of urges that were too powerful to resist.

I was never able to make her cum. My dick was too small and it would just slip out of her when she was on top, and, she hardly felt it when she was on the bottom. Because of my size, we were limited in the positions we could use. She had been too kind to ever make an issue of it, but, here was concrete evidence that I was inadequate and her sexual urges had turned elsewhere for sexual gratification. She did not point this out to me, but, she did not have to state the obvious.

She repeated many times how ashamed she was. She said these boys treated her like a piece of meat. She explained that, even though she has always found such treatment of women very offensive, - there was something perversely pleasurable in being treated like that - being picked up and slammed against a wall and taken in a savage and rough manner. She could not fight the raw urges to be manhandled like that.

She was very apologetic. She wailed and stated that she did not deserve my love and that I needed to dump her and find someone that could be loyal to me.

I asked her if there was anyway that she could stop giving in to these urges. She replied, "Honestly, I don't know! I want to tell you that it will never happen again. But, I can't stand lying to you anymore. Every time I cheated, I felt a profound sense of shame, guilt and disappointment in myself. I swore to myself it would never happen again. But, then - a blast of hormones and urges clouded my judgment each time. I am like a heroin addict! I'm defeated and I'm worn out from the fight and the guilt and the shame!"

My head slumped. I asked her, "What are you saying? You are giving up? You will not going to even try to be faithful to me?"

She looked down, held her face with her hands and sobbed.

She said, "You deserve better. I've been acting like a slut! I AM a slut!"

I asked her, "Do you think they gave put something in you drink? Could they have drugged you?"

She answered, "No, nothing like that. I am just going through a crazy spike in my libido that floods everything else in my brain. I need to sort out a lot of things. But, I cannot live with myself the way I have - betraying you."

I wanted to scream. - I wanted to kick her out the door and out of my life for ever, but, - my life would be pointless without her. If I lost Carol, I might spend the rest of my life alone, stroking my little dick. Carol had made me a pathetic cuckold, but, at least I was having sex with her, and she was hotter than any girl I could ever again hope to have.

I tool a deep breath, "Carol, I feel punched to my stomach right now. My heart feels like it has been ripped out and put through a shredded. My ego feels like five guys have taken a piss on it. But, I can also see how conflicted you have been and I understand that you are going through something and you need to ride it through. Maybe your hormones will return to normal in a week or a month."

I had to swallow my pride and accept that leaving Carol would be a worst fate.

"I know your heart belongs to me - and, my heart belongs to you." I said.

I told her my decision, "I am not going to leave you. I am going to look the other way while you get this out of your system. You don't have to fight with yourself or feel guilt about it. Just please - be careful."

Carol looked at me startled. She could not believe I was giving her carte blanche to fuck any guy she wanted. But, what choice did I have?

A pathetic cuckold with a hot girlfriend is still better than pathetic with no girlfriend. - Isn't it?

She stopped crying and smiled with relief. "I don't know what to say. I betrayed you and you should have kicked me out on the curb. I was sure you would dump me! Oh baby thank you for forgiving me and understanding!" She said, wiping her tears.

We kissed tenderly - but, I was not in the mood for sex that night. I told her I had to go to bed early, because, I had an exam in the morning.

I felt dead inside. I was a zombie. Even though I was somewhat touched by Caroline's confession and the agony that she had gone through, I felt a profound resentment and hatred towards her.

Even though I was angry, I understood her actions. If I had gorgeous dumb bimbos trying to rip my clothes and jump on my cock, I would have succumbed to the temptation. But, that would never be the case for me. I resented that Caroline was so beautiful and would always attract men, while I had no one else that felt attraction for me.

My depression was the most profound I have ever endured. I decided to go out to a bar. I drove on the main street for about 45 minutes, because, I wanted to get far away from the college scene. I did not want to run into any jocks and wonder which one of them was fucking my girlfriend.

I found an upscale bar about 45 minutes away and decided to give it a try.

The crowd was a little older. Mostly, upper middle-class professional. Some of the women were very attractive. After drinking a few cocktails, I felt the courage to talk to women. Perhaps there were some cougars in this bar and - who knows?

I talked and flirted with a very attractive women in her late 30s, and I felt like I was doing okay. But, then, the inevitable thing happened. Another guy came over to talk to her. I felt small and tiny standing next to him. She stopped talking to me, and later, she left with that guy.

I finally gave up. I took sat at a stool and ordered three shots of tequila.

"Rough night?" a guy asked. I looked at the guy that asked this. He was a tall and athletic black man dressed in expensive-looking casual business clothes - designer blue polo shirt, khaki slacks, and a navy sport jacket. He was probably in his mid 40s. Even though he was wearing a sports jacket, he looked like he was probably very fit.

I noticed he was wearing a Rolex watch. He smiled.

"Rough does not even begin to explain it." I answered.

We started talking. I assumed he was married, because, several women tried to start conversations with him, but, he showed little interest in them.

He told me his name is Ted. He had graduated from the same college I was going to, and then, he started his own advertising company and was doing very well.

After a few tequilas, I opened up to him and told him everything - yes, everything! I revealed to him all my insecurities and told him about my cheating girlfriend.

He said, "The most important thing that I have learned in advertising is that everything can be sold if you apply the right packaging and market the product to the right target group. Something that may be considered unattractive or inadequate to one target group, can be repackaged and made very appealing to another target group."

My curiosity was piqued by this cryptic comment. I wondered how this applied to me, so I asked him, "You think I can be repackaged and sold to another female group? Like what? Another ethnic group? Who? Asians? Latinas? Black girls?" I asked.

He just giggled.

"Listen, how open minded are you?" He asked.

"Would you agree that, if someone can give incredible sexual pleasure - more than you ever dreamed possible - this would be great, even if the sex was a little unconventional and taboo?" He asked.

What was he talking about? I asked him, "You mean kinky sex? BDSM? You think that if learned to spank or cane a girl, she would overlook my short stature and small package?"

"Not exactly what I was thinking." He said with a grin.

"Then, I don't understand." I said frustrated. "Just explain to me what you are talking about." I commanded impatiently, raising my voice a little.

He took a deep breath.

"Listen, you are a tiny white boy with a tiny pecker. I cannot sell you to girls - period." He said.

I sighed.

"But, if you shaved your body, put on a sexy skin-tight mini dress, sky-high heels, have a makeup person do your face, add fake tits and fake long hair, you would be stunning!" He said with some conviction.

He continued to speak, "You would have a new life. You would be very desirable and have your pick of sexual partners. And, - do you know that a prostrate orgasm is the most powerful type of orgasm on the planet? Once you get a taste for it, you will forget all about chasing pussy!"

I was totally stunned! I was flabbergasted! Was he joking? Did he just fucking tell me I was better off as a crossdressing queer?

When the shock finally wore off, I said, "Fuck you!" and I got up from my stool to leave.

Ted looked down at the floor. He said apologetically, "Damn! I was too abrupt. I should have been more subtle. I'm sorry, man! Don't go. Let me explain."

He spoke, again, "Listen - I'm just saying - you have a very cute face and a small feminine body. You should have been born a girl, and, you would have been smoking hot. - But, becoming a crossdressing girly boi is the next best thing, - hell, some men actually prefer that!"

I told him indignantly, "I am not fucking gay! I don't want to be a damn crossdresser! I want to be a guy that fucks lots of girls - not a crossdresser that gets used by guys!"

"Don't knock it 'till you try it." He replied. "A fuck is a fuck. If you can have your pick of lovers and fuck whenever you want - that is the path to take." He declared.

I was disgusted with this conversation, so I had to leave.

Ted took a business card out of his pocket and handed it to me. But, I refused to take it.

"Fine." He said. "You will think about what I have said, and, when you have fully process it, you WILL become very curious. Come back to this bar and ask any of the bartenders to give you my number. Ask for Ted Johnson." He said.

I stormed out of the bar, mad as hell.

But, Ted's speech did have an impact on me. For the next few weeks I kept wondering about whether I would look hot in women's clothes.

Ted said the next best thing to being an actual girl was to be a crossdresser girly boy. His comment that I would make a beautiful crossdresser was gross, - but, on some strange level, the idea of being attractive and desirable was very flattering and appealing. I was so desperate to be an object of desire.

Would I look hot as a crossdresser? As much as I tried to suppress this strange question, it kept haunting me.

Finally, a month after my encounter with Ted, I had to find out - What would I look like in crossdress?

I had to do it just one time. What harm could come of this? I just had to know if I would really be beautiful.

I visited a mall that was an hour away from the school campus. With a lot of trepidation and embarrassment, I walked into several stores and bought things at Bebe, Victoria Secrets, Fredericks of Hollywood, and Steve Madden. I told the store clerks that I wanted to buy something sexy for my girlfriend to celebrate our anniversary. I was terrified that they may see through my lie, but, I got through it.

I also stopped at Spencers and bought a long black wig, which was sold to be used as part of a witch's costume.

I spent all the cash I had, which was about $200. I put all these items in my backpack.

When I got back to my dorm room, I made sure the door was locked and the window blinds were completely covering the window and I took the items out of my backpack.

I was so nervous! My heart was pounding like it would explode! I had five-inch black high heels from Steven Madden, a black skin-tight mini skirt from Bebe, a red corset from Fredericks of Hollywood, and a red lingerir set of bra, panties, garter belt and thigh high stockings from Victoria Secret.

I felt a strange rush of eroticism putting these things on. Maybe, I was turned on by the fact that I was doing something very naughty and taboo or maybe it was the sensual texture of feminine clothes.

I stepped up into the heels and could not believe the transformation! I was almost as tall as an average guy. I noticed my body assuming a feminine posture to maintain its balance.

I walked slowly - trying hard not to fall.

I walked to the mirror, and - oh my God! I could not believe my reflection!

Ted was right! My body - which I had always hated so much - looked so feminine and pretty in women's clothes!

Shit! I looked hot! I turned and looked at myself from every angle.

With a little makeup on my face, I could give Caroline a run for her money!

I felt a surge of arousal and a strange boost of self-esteem washed over me. In some parallel universe, I was a smoking hot babe, extremely desirable!

I rubbed my hard cock through my sheer panties. I was so fucking horny! I wasn't sure if I was horny because I was turned on by that hot chick in the mirror, or if I was turned by BEING that hot chick in the mirror.

I am not gay - am I?

Then, something even more terrifying started to happen! I started to fantasize about Ted breathing on my neck and putting his hands on my bottom. And, I came harder than I had ever cum up to then.

The shock of all this was too much! I was alarmed by what I had just done and repulsed at myself. I peeled all the clothes off my body, placed them all in a garbage bag, and dumped in all in my garbage can.

I never wanted to think about crossdressing or about Ted again.

Unfortunately, the clothes did not stay in the garbage container for long. Thirty minutes after I had taken them off, I put them back on, and I masturbated furiously. I had never been so aroused in all my life! In this second masturbation, I fantasized that Ted was touching my face and lips with his fingers.

After I came the second time, I peeled all these clothes off my body, again - put them all in a garbage bag, again - and placed the bag in my garbage container, again.

This time, they stayed there for about two hours, when I was hit with the overwhelming urge to dress up and masturbate, again.

I fought the urge with all my will power. But, my will power was defeated. This time, I fantasized about Ted bending me over his knees and spanking me with his big black hand.

When I finished masturbating the third time, I realized that I was hooked on crossdressing, and that throwing all this stuff away was useless. I would end up spending another $200 to buy it all, again.

For two weeks I crossdressed and masturbated every day, sometimes, as many as three times.

I thought a lot about what Ted had said about prostate orgasms, and, I started probing my anus with small objects like pens and markers. This gave me intense pleasure.

The first time I came from probing of my butthole, I shot my wad across the room. I had never shot my wad that far. It usually just dropped onto the floor.

Ted was right! A prostate orgasm was more intense than cumming from stroking my cock or sex with a girl! I felt my butthole tighten and spasm when I came. WHAT THE FUCK? THAT MADE ME CUM SO FUCKING HARD!

However, I did not think I would ever put anything bigger than a pen in my butthole. Even a pen was painful to insert. Anything larger would be excruciating.

Meanwhile, my relationship with Carol was going very well. She seemed very happy and relaxed now. She had lost the tension and anxiety I had noticed before. I guessed that she was so relaxed now, because, she was having all the sex she needed on the side, and not feeling guilty about it anymore.

She had the best of both worlds: a loving boyfriend that doted on her like a princess and a stable of jock studs that treated her like a piece of meat - which apparently got her rocks off.

Because, I was too busy on a new sexual journey of my own, I did not obsess with what she was doing on the side.

Carol and I had sex frequently. I was afraid that sex on the side would leave her too exhausted to have sex with me, but, if anything, she was hornier than ever!

Even though she did not orgasm with me, I think she used me as a sex appetizer. She always had an excuse for having to run off quickly after making love, and, I knew that meant she had someone else lined up as her main dish. At least, I was not getting the sloppy seconds. Someone else was getting sloppy seconds. Ha ha!

Though, there was one time that I did get sloppy seconds. Carol and I had agreed that I would pick her up at her room to take her to breakfast on a Saturday morning.

I arrived at the door of her dorm room a little early and she was just getting back from somewhere.

She was dressed sexier than I've ever seen her - quite slutty, actually. Anyone could figure out she was just getting back from spending the night with someone.

"You are early!." She said, very embarrassed. "I need to brush my teeth, shower and change clothes before we leave." She said.

Seeing her dressed up in 'fuck me' high heels, a tiny pink mini skirt, and seeing her bra-less nipples poking through a thin baby blue t-shirt made me instantly and uncontrollably horny. I grabbed her and I brought her lips to my lips.

"No! You cannot kiss me right now!" She protested and covered her mouth. "Let me clean up, first!" She begged.

I quickly deduced that she had just finished blowing and fucking some dude.