Princess on the Balcony

Story Info
A willing CD is forced into blackmail by two young men.
10.5k words
4.68
24.6k
43

Part 1 of the 3 part series

Updated 06/10/2023
Created 06/04/2021
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I was loving my new condo in Pennsylvania, in my home town of Easton. I am a web designer and I decided to move out of New York City and move back home. The best decision I ever made. I had twice as many clients as before and with the space I had, I did all of my work from home. The place was perfect. I was on the top floor, 4th, of a row of about a dozen units and the back yard was all Greenlands with plenty of trees, as far as the eyes can see. I especially loved my wrap around balcony, not only was it wide and long it was also pretty private.

Being a crossdresser, since I was young, I loved having my own place to dress up. Finally at 26 I had a place of my own, no parents and no roommates. I even had 2 bedrooms one for my male self and one for Sabrina my female alter ego. Lately I have been spending much more time as Sabrina, which was wonderful.

I loved lounging around in all my female finery on the balcony, posing and taking pictures. The light of course was perfect. My favorite thing in the world was to dress up and feel the wind through my long hair and the breeze on my nylons. I would get so excited I would have to run back in my room and take care of myself. One day I envisioned strutting through the park or shopping in the malls, in my impossible high heels and short dresses. It's such a small fantasy, just something, I'm sure, most of us have.

The condos were full of families and couples that I would see throughout the week. My mother's friends, the Hamilton's live on the second floor of my building and I would be the recipient of some fine muffins or cookies that they have been baking. I also ran into a couple from college that I knew, and even my old boss from a Deli I worked in when I was in high school lived here. I didn't realize moving back home would bring so many acquaintances back into my life again. I even started dating Leeza, a girl I went with while I was a freshman in college, she lived about 3 miles away. We didn't see each other often, she was always quite busy. Usually we hung out on her side of the town, and I didn't tell her about my crossdressing of course. Also on the first floor was a number of retail stores and business's, I became the keeper of four out of five of those websites, when I told them I lived right here in the building. I very rarely visited them in person, but with them and my other clients from NYC I was very well off and had plenty of work.

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Sometimes when I would dress up, late at night, I would put on my dark sunglasses and I would take the backstairs to my car. The stairs were dark and out of the way and no one ever used them. The best thing was at the foot of them was my parking spot. Once off the stairs it was only 4 steps to the inside safety of my car. Usually I would just drive around, reveling in the feel of my heels on the gas pedal. Then I would find a quiet parking lot and just hang my stockinged legs out of the car. I was way too nervous to get out and walk around, but I loved the night air. The feeling inside me was wonderful, I was just another woman out on the road. When the excitement got too much I would head back to the condo to slip into something even sexier and talk to friends and sometimes men on social media.

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The Christmas holidays came around and the units were buzzing with children and adults home for the week. My neighbors on my floor must of had 20 people in their unit, I heard them partying most nights. I didn't mind I just stayed in and practiced walking in my heels, most of them 5 inches or higher. It was a fantastic way to release stress.

I remember this Christmas Eve, I was all by myself. My mother, who lived nearby was with her family. My Father died 12 years ago and she remarried and moved a little further away. Leeza went to New York to visit relatives, and even the Hamilton's were visiting some friends out of town, though they did leave me some cookies. So I decided to stay home and try on my new dresses that I purchased online. One I especially couldn't wait to get into was a red sequined dress with gold sandals.

I started in the shower, shaving all the hair off once again. Leeza never really saw me completely naked, so she was never that surprised in my hairlessness. Next I used lots of lotion and put on my 36C breasts from the Breast Store. Where were these all my life? Looking in the mirror I wished they were real, and I loved the feeling of them on my chest. Next came my hip pads, beige corset and bra, and then my nude Sheer Elegance pantyhose. I loved my red toenails shining through my nylons. My reflection in the mirror showed a cute 5'8" blonde with a nice feminine shape. I exercise a couple of times a week to showcase my female form. I even take online dance lessons to help shape my legs, butt, and waist. They also give me slightly more confidence in my movements and gracefulness when I walk. My other bedroom was filled with exercise equipment and I even had a stripper pole here next to my vanity. My wall of closets had floor to ceiling mirrors on them so I can watch myself dance and strut.

I sat at my vanity and put on my wig then makeup. My wig was always first. Even though my hair was quite long, I loved the look and feel of my even longer strawberry blonde wig blowing in the breeze. Feeling the hair all the way down my back.

I relished the time I had to put on makeup. When I was young I was never able to afford the time do it correctly or even had any idea how to do it right. Watching YouTube tutorials changed my life and now my makeup was perfect and somewhat effortless. I loved putting on my false eyelashes and painting my already full lips. Next was my press on nails, one day I would get real nail tips but for now these were easy and always looked great. The longer the better.

I then stood in front of my mirror and slipped on my short sleeved red sequin mermaid dress. With the hip pads I had a perfect curvy shape. I sat to strap on my gold five inch sandals, and almost fainted when I saw my complete self in the mirror.

"Oh my God Sabrina, you have outdone yourself tonight."

I put on my big thin golden hoops, which almost touched my shoulders, then my matching choker. The choker not only made me look exquisite but it hid the seam of my breast forms. Lastly I added a couple of rings and a small watch on my left arm. A little spray of J'Adore perfume, a quick brush through my hair, and I grabbed my red clutch and made my way to the balcony. Whenever I dressed up I was always completely dressed.

It was still early and light out around 6 O'clock. I heard parties going on next door and below me, wishing that I could be at one of them. It was a cold night but I wanted to get a little time in the December air, relishing my time outside in the world. One day Sabrina would walk into a party in this beautiful dress and all the men's and women's eyes would be on her. I always wanted to scream, "Here I Am." to the trees, but I was so nervous someone I knew would see or hear me. For some reason I always felt that I needed a little push to go further. I felt like I was in neutral just waiting for that one more notch to make it to drive.

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Waking up my first Christmas morning in a nightgown, in my own home, was wonderful. All the little rituals were so much better as a woman, making coffee, checking the weather, even brushing my teeth. Being able to see a beautiful woman staring back at me was an amazing feeling.

I hung around all day in another Christmas outfit that I bought at a major chain store. It was a costume for a Sexy Santa's Helper. I always considered myself a sexy helper anyway so it was perfect for me. All it was, was a stretchy lo-cut green body suit with a snap crotch, and a green matching Santa hat. It had a black belt and a neck wrap with jingle bells on it. I paired it with my 6 inch red velvet pumps, which matched my red nails. I had to tuck myself in good to show my perfect female crotch, and once I was tucked in I looked incredible. I then slid a short red skater dress on, I was a little uncomfortable showing too much below the waist, even by myself. The outfit just reeked of sex and I couldn't get much done because I looked way too good. I came twice in as many hours.

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While I was relaxing reading one of my romance novels, I heard a commotion outside in the hall. I shared the landing with 3 other apartments so it wasn't that uncommon. I did think I heard someone right by my door so I waited 'til it was quiet and I looked out the peep hole, then opened the door. A small Christmas wrapped present was on the floor. I was thinking it must be from one of the neighbors so I slipped my delicate hand out and took it in. I didn't want anyone seeing me in my green Danskin, that's for sure.

The box was small and wrapped rather crudely, but I guess it was the thought that counted. The gift tag attached said, "To the Hot Girl in 4D"

"Shit," I gulped as I sat down and opened it up. I was completely shocked when I saw the package contained a thumb drive, a 64 gig one. I placed it in my laptop and saw there were over a dozen mov files and a folder. I got suddenly nervous.

I got up and took a shot of Schnapps, to calm my frazzled nerves, and went to open one of the files. This could not be good.

I clicked on the first one and it looked like drone footage of the trees behind the condos, 12 minutes of it. The next one I clicked on was footage higher that before, and then I saw my building. As the camera got closer I saw myself on the balcony in my Christmas dress. The wind blowing my hair, I looked so content. The other files were a little too dark, but if you looked closely you could see a woman, walking on the corner top balcony. Obviously it was my condo. I could have had a visitor last night for all anyone knew anyway. I took a deep breath and opened up the folder. In it was over 20 picture files and a notepad file. All the pictures were of me on the balcony, taken from below, some with my wig and some without. I was in a different dress in each one, almost my complete wardrobe. There was no way I could say it wasn't me. There was even one of me in just my heels, nylons and panties as I walked passed the window. Then I see that there was some of my male self. Obviously it was someone who was watching me for some time.

I then opened up the note, and it read:

'Hi, cute blonde in 4D. We have been enjoying your pictures for a while. We think it's time we meet. We will be there at 2.'

"Oh my God, I can't believe this, how many of them are there." For years I have been crossdressing and I have never been caught. Living in a house with parents and 3 sisters wasn't easy, but I was always able to get away with my dressing. With 2 roommates it was more difficult, I always had to wait until they went away. I did have some extremely close calls, that's the main reason why I got my own place.

I had 2 hours to figure out a plan, unfortunately the first thing was to take off my Santa helper outfit, and revert to my male self. I guess I wasn't going to be a girl for the whole Christmas week. Once I removed my makeup and changed, I took another shot of Peppermint Schnapps and waited for my admirers.

I looked through the peep hole and then I opened the door, after the quiet knock, and outside stood 2 young men just slightly taller than me.

"Ah too bad," one of them said, "We were hoping to see you in your red dress from last night."

Of course I feigned ignorance. "What are you talking about, maybe you better go." I moved to close the door but the dark haired ones foot went into the threshold. "Wait hear us out, we got so many more pictures, not much video, I just got the drone yesterday."

I let them in fast and closed the door when I heard the next door neighbors getting ready to leave. All I need is anyone suspecting I'm a crossdresser. I don't know why I was always so paranoid about it, but it always made me extremely nervous about being found out.

They introduced themselves as Jason and Ed, and they lived about a quarter of a mile away. This building was in between their walk from home to the local school. Lucky me, I thought, how convenient for them.

Jason spoke most, seeming to be the more confident of the two, he was also taller and darker. "We were thinking maybe we can see you in some of your other clothes, you look like those influencers on Instagram, ya know."

I was speechless. I couldn't believe these two young, clean cut men were trying to blackmail me. "We can't do this," I squeaked in a low voice. "You have to leave now."

"Ya, know, we have some great shots of you in so many dresses, you are pretty hot. Do you look as good close up as you do from a distance? Jason started walking around the apartment. "You have a nice place here, we were thinking maybe we can come around once and a while to, you know, hangout."

"We won't say anything to anybody," the quieter one said, "We are just not that used to seeing someone in real life who dresses like that. Even my mother, she only wears a dress when she goes to weddings and funerals"

"Ha," Jason laughed. "Yeah this could be fun, when can you get changed? We were also hoping, I don't know, maybe something else. We can talk about that later."

"I can't do this, how old are you two?" I asked

"We are both 18, Eddie will be 19 in another month. How old are you?"

"I'm 26 and too old for you, and you know, I'm not gay."

Jason smiled. "Well neither are we, but we know a hot looking woman when we see her. And we know what we have been doing while looking at your pictures isn't gay."

"What have you... Oh my God don't tell me." I was suddenly embarrassed, these two young men were getting off on my pictures.

"You have been me and Eddie's fantasy woman for months now, as soon as we've seen you, you have been our only inspiration if ya know what I mean." Eddie laughed as he looked at Jason. "I'm sorry." He said, "Sometimes we watch pictures of you all night, there are no girls in the neighborhood who dress as sexy as that."

"Look," Jason finally said, "Think about it, we will come back in say a couple of hours, get real pretty for us and we won't tell anyone. No big deal."

The two of them headed for the door. "We are having dinner with the family, we will come over after, around six. You can come if you want." Jason smiled and then they finally left, lightly closing the door.

They really didn't threaten me, actually they were quite calm and nice about it, almost apologetic. But I really didn't have much choice. I wasn't ready to share my dressing with the building, and who knows what would happen with my business. So I decided I would introduced them to Sabrina and hopefully come to a decision we both could live with.

I had to tone down the sexiness so I put on my white flowered dress, it was short but it wasn't that tight. It had cold shoulders and the front was high cut so I wouldn't be showing off my breasts. I put on nude pantyhose again and a pair of three inch heels. I put on my wig and a light touch of makeup, with pink lips. I had on thin dangling earrings and another choker around my neck to cover the seam of my Boobs. I was suddenly wishing I had smaller breasts, I can imagine them staring at them the whole time. Lastly I painted my nails white and grabbed my pink pocketbook. For some reason I never felt fully dressed without one.

I was very anxious as I waited for the guys to get here. I was sitting on the couch nervously bouncing my crossed legs. "This is so ridiculous, how did I get into this situation." I was going to tell them that this couldn't happen. I wasn't going to be masturbation material for two young men.

When the knock came I jumped, I was suddenly even more ill at ease than before. I just realized I would be talking to someone while dressed. Something that I have never done before. Even though I know I pass as a female, I had never had any interaction with anyone, except online.

I opened the door slowly and peaked out. "We're here, Merry Christmas," they both said as they entered the living room. "We thought you were never going to open that door." Jason said, "But wow, you are even more beautiful in person." Jason said. Eddie just stared at me and then he opened his backpack and gave me a present. "What is your name?" He asked. "Well my name, is Sabrina." It was the first time I have told someone my name, and I felt my face turn red. "We hope you are going to like this, and I hope it fits."

They both watched me open it with my long nails. I looked up and they had huge smiles on their faces. It was a box from Yandy Candy, whatever that was and once opened it revealed a black Playboy outfit. Including a fuzzy tail, a collar, wristlets and bunny ears. Every man's fantasy I'm sure.

"I don't know if I can wear this. I don't have real boobs you know." They looked at each other.

Eddie said, "It looks like you do."

I felt myself blush again as I pulled out the costume. It was tiny, I didn't even know if I could fit into it. The crazy thing was I couldn't wait to try, but not in front of them.

"Ya don't have to put that on now ya c'n save it for another day." Jason then picked up the wrapping paper and threw it away. "We wanted to get ya something ya didn't have, ha. We have seen a lot of you and your clothes."

The present sat between us as they pried me with information about my life as a crossdresser. I got them soft drinks and we talked for a couple of hours. They were quite pleasant boys, and were complete gentlemen.

"We were thinking," Jason exclaimed while Eddie watched on in trepidation. "Maybe with you all dressed up ya can give us... um... blow jobs?

"Jason, I don't think we should be discussing this, I told you I don't think I'm gay and I certainly have never given head before." Even though I have fantasized about it for years. I even had a 9 inch life-like dildo hidden in the bottom of my panty draw. I was hoping that they wouldn't press this issue further.

"We never had one before," Eddie chimed in. "And I know some of the guys we hang out with have."

Jason stood up and grabbed my hands to stand up. I was a number of inches shorter than him in my 3 inch heels. He looked at me and said, "I have to tell you sometimes that is all I think about, even in class. It's hard even just sittin' here smellin' your incredible perfume, and you have such beautiful eyes and lips." He gave me a deceptive grin. "How many have YOU had?"

I swallowed hard. "Um, when I was in college I got head from a couple of girls I dated. It has been awhile."

Eddie asked me from behind. "We see you sometimes bring a girl in here, doesn't she give you one?"

"You know I have a girlfriend?"

"Sure we know a lot about you, but why doesn't she give you head, she doesn't like it? I thought girls love to suck cock."

"I'm sure some girl's do, but Leeza my girlfriend isn't one of them," I sulked.

I looked at these two young gentlemen and asked. "It doesn't bother you that I'm not a real girl? You really want me to do this?"

Jason laughed. "Shit we didn't know ya weren't a woman for about a month when we first saw you, we don't care." He then kissed my hand. "Can you give one to us, maybe as Christmas presents? Please." I didn't know what to say, they were being so nice and respectful about it. I never would have imagined that this would have been my response, but wearing a dress and heels changes your perspective on all things sexual.

"I will on two conditions. One: Only one of you at a time, the other one will have to leave. And two: You have to talk to me like you were talking to a real women, like, don't bring up my girlfriend, or anything else like that, and everything below the waist is off limits. Treat me like you would any other woman."