tagTranssexuals & CrossdressersUgly Duckling to Sissy Princess Ch. 02

Ugly Duckling to Sissy Princess Ch. 02


(Continued from Part 1)

My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy clothes to tutor them, and after the "tutoring sessions", she looked sweaty and exhausted, like she had been forced to run through a tough military obstacle course.

I evolved from being a humiliated, jealous and resentful boyfriend, to finding the one positive thing about this arrangement. It removed all the pressure on me to give her the hard pounding a woman needs. I had always felt insecure and inadequacy about my diminutive equipment. I'm a small short white guy with a tiny pecker. I just don't have the tool to give her pussy a deep hard pounding.

But, I did not have to worry about that anymore. All she needed from me was tenderness and affection, which did not require a big cock. I loved and worshiped her and was her boyfriend and best friend.

After the initial shock of discovering her infidelities and reluctantly accepting this, our relationship evolved rather smoothly. Oddly, instead than being repulsed by her when she had just gotten through a fuck session with other guys, knowing she had just gotten a rough pounding from another guy got me more turned on. Why? Maybe because I felt I less pressure to perform in bed, because she had already been pleasured; or maybe, the thought of having a slutty girlfriend turned me on; or maybe, I developing some weird fetish for sloppy seconds. Who knows.

I always knew it when she had just been fucked, because, the hard pounding caused her to walk funny, and, she would look beat up, like she had been slammed against a wall. When I saw her like this, I would walk back to her room with her. I wouldn't let her shower or clean up, I would initiate make-out sessions that led to love-making. Her pussy would be sore from being fucked by big jocks and this soreness made her feel my little dick, which she would not otherwise feel inside her.

I did not even mind tasting cum in her mouth. That was another very odd thing. The taste of cum in her mouth was a major turn on for me. I know how gross this sound, but, it is just the plain truth, and I cannot deny it nor explain it.

While Carol was exploring her slut side, I was secretly exploring my feminine sissy side.

In part 1 of this story, I explained my strange first encounter with Ted, a 40-something athletic professional black man that owned his own marketing firm. I was drinking in a bar and we started to chat. He could tell that I had been through a very rough day, and he asked me about it. I should have kept my mouth shut, but, I was so upset and depressed and the buzz of alcohol made me want to talk and confide in him.

I told him about the sorry state of my life - that my girlfriend had confessed to being a slut behind my back to clear her conscience. She admitted that she could not help herself and could not stop, because, her libido was going crazy The jocks that she was tutoring were hot, and after being seduced by a big, rough and aggressive jock, she became addicted to rough sex like it was heroin. As a feminist, she could only love a man like me who treated her with the utmost love, respect, tenderness and admiration. But, apparently, inner slut was an altogether different creature. A dominant big strong jock would trigger her inner slut, and she became an eager fucktoy that like to be pounded on the walls and fucked like a porn star.

Instead of dumping her ass, I told her I would look the other way. Why? Because, she is hot and I am not. She is smart and nerdy like me, but, she has a hot petite body that turns heads wherever she goes. She could easily be lingerie model.

Me, on the other hand, I am short, skinny white guy with a small dick. Carol is 10 times out of my league, and I may never ever have a girlfriend that hot again. I do not want to spend the rest of my life jerking off to my pictures of her - so looking the other way and keeping her was the only sensible option.

Besides, I love Carol deeply and I cannot entirely blame her. If the shoe was on the other foot - if I was the one getting chased by hot and horny young babes, I may have reacted the same way as Carol.

I explained all this to Ted the night I met him at the bar and he sensed how low my self-esteem. He heard me complain about how I loathed my body, because I was short, small and had a small cock, and he told me I could change my life by repackaging myself and identifying a niche new market that finds me attractive.

It turns out that he was talking about me becoming "repackaged" by crossdressing! He said I had a very feminine petite body and a pretty face, and that I would look very hot as a crossdresser! I thought - what the fuck! I wanted to punch him in the face, but, I just walked out the bar. I was very offended by his statement, yet, this perverse idea somehow stuck in my head. I could not get rid of it.

How would I look in a dress and heels? Would I be hot? - These questions haunted me. This curiosity grew and intensified, until I could not ignore it anymore.

Why not try crossdressing one time just to satisfy my curiosity and move it? It could not be so bad, right?

The day I finally took the step of standing in front of my mirror in my new girl clothes was the day I got hit with a bolt of lightning! I wore five-inch black heels, opaque black thigh-high stockings, black skin-tight mini skirt, and a set of red corset, panties, and garter belt.

Dressing up like this was like dabbling in powerful black magic. It was intensely powerful and electrifying! I had never experienced anything so erotically charged in all my life!

The girl in the mirror was beautiful, sensual, and happy with her reflection. I had never before experienced this elation and pride!

Weeks later, I was becoming more and more infatuated with crossdressing, and, I was beginning to develop feminine fantasies.

I was glad that Carol spent so much time with her fuck buddies, because, I loved having time alone to crossdress and enter the world of feminine fantasies.

I had no intention of becoming a lifestyle crossdresser and I did not identify as a woman trapped in a man's body. Yet, for whatever freak reason, getting dressed up as a girl and allowing feminine fantasies to carry me away gave me the most powerful arousals and orgasms of my life!

I love how sexy and attractive I became in girl's clothes. I enjoyed watching myself in the mirror as I dressed up. For the first time in my life, I felt attractive. My favorite part of my crossdressing ritual was putting on pantyhose and high heels. I left this for last and did it slowly, watching myself in the mirror. I used black opaque pantyhose and tights, because I had not shaved my legs.

Even though I began fantasizing about being touched and used like a girl, I did not consider myself gay, because I did not want to do this in real life. They were just taboo fantasies. I also poked and probed my asshole with pens, and discovered a dimension of physical pleasures, but, I was too scared to try ramming anything thicker than a pen inside me.

I got Ted's telephone number from the bar where we met, and I called him on the phone. I confessed to him that I had started to experiment with crossdressing. I only called him because he seemed to know about this stuff and it was new to me and I was so clueless. He was friendly and invited me to a crossdressing party hosted by one of his clients. I was reluctant to agree, but, curiosity got the better of me, and I accepted his invitation.

I spoke to Ted, again, one day before the crossdressing party. I told him that, although I was curious about crossdressing, I would never do anything sexual with a guy. I wanted to make that absolutely clear.

"Why not?" he asked.

"I don't know. I just think it would be irreversible, you know, like once you go down that road, you are a cocksucker and will always be a cocksucker." I explained to him. I also said to him, "I don't think Carol or any other girl would want to marry a guy that has sucked a cock."

Ted laughed and said, "When you marry a girl, the best thing to do is to don't ask and don't tell. Your wife may have been a dirty little slut that enjoyed gangbangs in college. Don't ask about her sexual past. Most women do not disclose everything they've done, anyway. So, you don't have disclose everything you've done."

"But, still - I don't know, I just couldn't be with a man! That's just too much change for me!" I said. "I have been heterosexual all my life. Changing that now would be to throw myself into an identity crisis that could have many negative consequences. I want to have a little fun, but, I don't want to get in too deep." I added.

"James, you need to understand that I will always respect your boundaries, and everyone else in our community is extremely respectful of personal boundaries. But, damn it! I was hoping you would suck my cock after the party!" He said comically.

I was glad he could not see me blushing.

The truth is, I had developed an elaborate fantasy involving Ted: I am in a biker's bar in a very sexy outfit - short red leather mini skirt, sheer black nylon pantyhose, 5-inch black stilletos and a tight white satin blouse and white bra underneath. Five big strong rough-looking blue-collar biker guys flirt with me and buy me drinks, and, I love the flattery and attention. But, then, things get a little ugly. They ask me if I am interested in gang-banging them in the back alley. I do not want this and I try to leave, but, two of them pick me up and carry me out of the bar and into the dark alley. I am dropped on the dirty ground and they take turns slapping cocks on my face and I get pre-cum splashed all over my face. Then, just as they are about to use me as their little fuck toy, Ted suddenly shows up to rescue me. He fights them off, then, picks me up and takes me to his nice city condo. After I clean up my face we watch TV on his couch. I show him my appreciation by moving my hands sensually on his pants over his cock. I feel the rise of a big snake, and I pull down his zipper to release his black anaconda. My jaw drops when I see it. It is black, big, long, and fat; an intimidating reptile, but, I do not falter. I gently kiss its head and sides. I tease the head with my swirling tongue. It oozes pre-cum, and, I lick all of it. Then, I open my jaw wide to give him the best blowjob of his life and swallow half of his monster cock down my throat. He moans, grunts, trembles, bucks his hips, and then, erupts like a powerful volcano. He cums deep in my throat filling my stomach with his warm milk.

Ted's joke about me sucking his cock triggered this daydream about my fantasy and I forget that we were in the middle of a telephone conversation.

"Hello?" said Ted. "You did not hang up on me did you? I was just joking, James." He said apologetically.

"Its fine, Ted. I know you are a pervert. You can dream about me sucking your dick, but, it will never happen!" I said to him.

I wondered - Why do I have Ted stuck in my feminine fantasies? Why do I fantasize each night about sucking his cock? I guessed that it must be like what some patients feel towards their therapists. In a way, Ted was like my counselor. He had opened a new door for me and was guiding me in this new journey.

Ted explained to me that young crossdressers are sometimes referred to as "sissies" and "femboys" in parties, but, I should not not take offense to these names. When a man and a sissy would hook up, the man would call the sissy his "sissy slut," "sissy slave," "sissy fuck toy," etc. Ted also explained that most sissies enjoyed some submission and humiliation.

After talking to Ted, I wondered - Was it really a good idea to go to this crossdressing party? Crossdressing in the privacy of my room was one thing - it was safe. But, taking my crossdressing outside and sharing it with strangers was terrifying.

Friday, the day of my first crossdressing party finally arrived! Ted had explained to me that his assistant, Bernice, would be picking me up at about 7:00 pm to take me shopping and get me ready for the party. Ted said he would pay for everything.

The meeting place where I would meet Bernice was Nic's Bar, the same bar where I first met Ted. I arrived and sat at a bar stool. I ordered a Tequila shot.

God, I needed some liquid courage tonight! What was I getting myself into? I was extremely nervous. I thought I would vomit.

For the first 5 minutes, my eyes were glued to the door. Every time the door opened, my heart dropped to the floor.

About 15 minutes after I arrived, a beautiful young woman in her early 20s walked in and scanned the room. She was unbelievably stunning! She was white and European-looking - I'd guess Italian or Spanish, with beautiful blue eyes and long dirty blond hair.

She wore dark eye liner and dark red lipstick - like a hot goth chick that grew up, but, retained a slight remnant of her goth attitude.

She was dressed classy sexy. The length of her dark purple mini skirt was short enough to cause men to stop whatever they were doing to stare, but, long enough to stay on the classy side of classy vs. slutty.

She wore a designer tight white button blouse and black boots, which, I later learned were Christian Loubitins.

She had a thin waist, but, nice curvy tits and ass. The top two buttons on her blouse were open to show a little cleavage; a hint of the fine set of tits on this girl.

I stood frozen. Shit! I can't go shopping for girl clothes with a hot chick like this! She would intimidate the hell out of me! Time stopped when she looked around. All the men in the place were gazing at her, wondering who was the lucky bastard she came looking for. She made eye contact with me and flashed me a big smile.

Oh my God, it is Bernice! I looked away nervously.

I heard her foot steps as she walked towards me. "You must be James. You are exactly as Ted described you."

All eyes at the place where on the two of us.

She was quite a bit taller than me - the boots added about 5 inches to her, but, even without the boots she was probably several inches taller than me.

I extended my hand to her to shake her hand, but, she ignored my hand, choosing instead to wrap her arms around me and give me a big bear hug. Then, she kissed me tenderly on the lips and made an "mmm" noise!

Holy shit!

I could hear people murmuring.

When she stopped kissing me on the lips, she said in a loud and excited voice, "Let's go, baby! Now! I can't wait anymore!"

I said nothing. I just pulled out some bills from my pockets to pay for my drinks and I stood up. I noticed the bartender staring at us with his jaw wide open.

Bernice grabbed my hand and pulled me to the door.

I was as shocked as everybody else in the bar, but, I acted like this was very normal for me.

As we walked out of the bar, the guys in the bar were giving me the thumbs up or holding up their drinks up as to salute me.

Why did Bernice decide to put on this show at the bar? Did she think I was a pathetic little guy that desperately needed something like this to lift his sorry little ego.

Was this her 'random act of kindness', her act of charity?

"Why did you do that? I have a girlfriend you know." I said when we were outside.

"I don't know!" She said giggling.

"Everyone was staring at us in there. We had to do something to provide them a little entertainment." She said.

"And, I like to kiss, so sue me!" She added laughing.

I did not know what else to say to her. I was so intimidated by her looks. I followed her to her car, a red sporty little Volvo convertible.

It occurred to me how surreal this was. This smoking hot girl was going to help me transform into a sissy!

We got inside her car and she started to drive.

"Ted was right. You have a beautiful face and a beautiful feminine figure." She said, trying to compliment me.

But, rather than accept her compliment, I felt very slighted by this. "I see. I am pretty like a little girl, but, you would never look at me as a man that you would fuck, right?" I was surprised by my own rudeness and regretted it instantly. She was only trying to be kind.

But, she did not take offense by my rudeness. Instead, she giggled and said. "I'm going to make you look so fucking hot, and maybe, I might fuck you! - But, be very careful what you wish for!"

She must have noticed the stunned expression on my face and she laughed some more.

She explained, "I'm a lesbian. I fuck hot girls, and, I have fucked a little sissy here and there. But, Bernice always DOES THE FUCKING!"

"You won't be able to walk straight for a week after I fuck you!" She laughed demonically. She winked at me and reached with her hand to feel my knee, like a guy would do to a girl. I blushed. She was having her fun at my expense.

We got into a more serious conversation about ourselves. I told her I was in college studying political science.

She told me she had studied psychology in college and went on to graduate school. Now, she worked closely with Ted in marketing and publicity.

She also told me that during her graduate studies in psychology, she paid her tuition and living expenses by working as a professional dominatrix. She explained to me that being a dominatrix did not involve sex with her clients, but, if she wanted to fuck one of them, she made exceptions.

"Providing dominatrix services is the best type of psychotherapy there is." She said. "My job was to discover the repressed taboo fantasies of my submissive clients, and then, I would force them to do the sexual activity they repressed. Forcing them to do it gives them plausible deniability. I was like the devil, they blamed me for forcing them to do what they've always wanted to do really bad."

She continued, "For example, let's say you wanted to suck Ted's cock. Maybe, you cannot admit that to yourself, and maybe, you will never have the courage on your own to go up to him and beg him to stick his meat in your mouth. But, if I get involved, I will command you to get on your knees, unzip his pants, whip out his dick and suck his cock like a baby suckling on his mom's tit for milk. Then, you can blame me for forcing you to suck Ted's cock and deny how badly you wanted it."

I was upset that she had used this example. I snapped at her, "That is a really bad example. I do not want to suck Ted's cock!"

"You don't?" She asked. "Every other sissy I know does." She said giggling.

I told her, "First off the bat, you need to know that I am not gay!" She looked at me, and said, "Of course you are not gay! You are you, which is the journey of discovering and becoming you. This cannot be reduced to a single word."

The next couple of hours were very bizzare.

She took me to an upscale wig shop. She tried many wigs for me to see how they looked. My favorite was a short black wig with straight hair and bangs.

When no one was looking, I tried it on and she said it was perfect on me.

She also picked out two long curly hair wigs, one in black and one in my natural dark brown color.

Then, we went to a spa where all my bodily hair was removed. It was an excruciating process, but, Bernice made it more bearable by exposing her tits to me in times of pain to give me a lot of encouragement.

I felt very strange putting my clothes back on without my body hair.

Bernice kissed me on the lips and said with a wink, "You are already looking so feminine and sexy." I was really enjoying my time with her.

The next thing we had to do was buy women's clothes. I told her that my girlfriend had a few Bebe dresses and I loved how sexy they looked. I wanted a short and tight cocktail dress for the party.

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byJHouston© 7 comments/ 37833 views/ 28 favorites

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