Princess on the Balcony Pt. 02

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CDs life gets better with the help of her first boyfriend.
12.9k words
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Part 2 of the 3 part series

Updated 06/10/2023
Created 06/04/2021
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Princess on the Balcony, Part 2 Life With Charles

'Sorry this has taken so long. It got a little out of control, I now have a part three which is kinda crazy. If anyone reads this one I will publish it. Thanks'

***

(Catch up, Sabrina gets discovered by two young men. She agrees to give them head so they won't tell anyone about her. They tell everyone. They go away on vacation and introduce her to one of the fathers. Okay caught up.)

It was Friday night July 5th, I was on my balcony looking out at the Greenlands behind my building. The balcony itself just got a major upgrade, reinforced walls, a retractable awning, and even indoor-outdoor carpet. I was dating a man in construction and I just had my first orgasm of the weekend.

Even my walk-in closet got a make-over, and in it, I had two different sets of outfits. The left side was for the world and the right side was for Charles. Charles was behind me right now as I held onto the metal railing surrounding my balcony, and it never squeaked anymore but I did. Tonight I had on a pink short sweater tied with a little string right in the middle of my boobs. I had a short full pleated white skirt hovering somewhere below my crotch showing off my barely-there crotchless pantyhose. My heels were my favorite items I owned, they were the best one hundred and thirteen dollars I have ever spent. I had on my clear 'Pleaser' seven-inch, double strap, slip-on with a white platform, phew. Six-inch heels were always my go-to, but since I discovered that extra inch there was no going back.

Charles, or Charlie as I rarely called him, was behind me. His hard eight-inch cock was sliding around my ass cheeks, rubbing against the nylon. I had to spread my legs to get my 'pussy' lower, because the heels made me so tall, otherwise his cock wouldn't have been able to penetrate me so easy. With my Pleasers on I was one inch shorter than him, he was 6'4" to my very feminine 5'8" in stockinged feet. I loved a tall man and I now loved a hard cock, who would've guessed. He would tease me as his hands reached around to my breasts. I just had a boob job. Charles said it was the best kind of job after a no-show one. My breasts were DD-cups and they hung and swung so beautifully as his cock started to enter me again. This was only the third time we had sex since I got implants and the first with me standing and swaying. I could get used to this.

"Ohh, Sabrina you feel amazing." He moaned as the length of his cock made its way into my waiting 'pussy.' Fucking has been so much easier after my initial cherry popping, about two months earlier. He pushed in and out of me as he grabbed hold of my hips. My hips were a little wider, Charlie told me, than when we first met. I think it was his imagination though, I had only been on HRT for three months. I felt his hands on my skirt-covered hips and then he moved his lips to my neck. My sweater was low in the back and made of pink angora. There was plenty of room for him to lick and kiss my neck and shoulders, even my hair wasn't in the way.

I decided I needed a major change in my life since HRT was underway. I cut my hair. I have always had long hair, sometimes down to my ass, a wig of course when I dressed up, but now it was all me. I had no extensions, no falls, just hair, Sabrina's hair. I was very happy. Now my blonde-streaked bob was blowing in the slight wind. The length ended a couple of inches below my chin and curled in towards me. I also had bangs reaching right down to my long lashes, I was constantly brushing them out of the way. I loved when Charles watched me, I would sexily play with my bangs and fluff up my hair, I was so girly now.

As he pushed in and out of me I felt my orgasm starting to build. Charles had a way of aiming his cock in different directions inside of me, fucking me differently every time. I couldn't understand how he could find some crazy erogenous zone that I didn't even know existed. He told me he never made love like this before, but now he was never going back, this was it. I was glad. I started to moan when he shot his jism inside me. I felt it, it was wonderful. I always came myself when he shot into me, just the idea of his sperm making its way through my body was enough to take me over the edge. Hopefully, only the Greenlands heard me scream.

Second orgasm down, a multitude more to go.

***

Friday night was date night for Charles and me. That was the night he slept over. I usually could convince him to stay another night. He always teased me that he was so busy, he had to go home, he had things to do. I would pout, "Okay Charles if you have to. I will miss you something terrible." Actually, now that I think of it, he always stayed until Sunday. Hee hee.

Friday night at six he would show up all showered and shaved, dressed to impress. I told him if he wore a jacket and tie I would let him make love to me. He always wore a jacket and tie on Fridays, and I always dressed from the right side of my closet. We never went out, we saved that for the rest of the weekend and the few too times during the week. This night was for us. I was hanging on his neck before the door was even closed.

"Did you miss me as I missed you?"

"I did, I start to miss you as soon as I'm leaving and I hit the elevator."

"I will walk you down to your new Jeep from now on." I giggled. I loved walking through my building all dressed up, usually on Sunday nights clicking in my heels. I had to slip on a robe or a coat, I wouldn't want to excite any of the tenants, the way Charles excites me.

I have been living here in Easton, PA for ten months it was the best move I have ever made. Back then I was afraid to even look through my peephole in a dress, but now I walk around the building and the town constantly. Everyone now knows me as the girl with double DD's in 4D. I met Charles this past April, now it was the beginning of July. Ninety days ago.

I was friends with his son, Jason. His nineteen-year-old, he had three other children. His wife was sadly gone and all of his kids have moved out, he only had Jason home now. I was also friends with another teenager, Eddie. The two of them took it amongst themselves to introduce me to Charles. They were bright kids, and they knew me so well. They showed him my picture. He thinks I don't know he still has it but I have seen it hidden in his glove compartment in an envelope.

Charles was perfect for me. I was twenty-six and he was exactly twenty years older, I was ready for an older man in my life no more students for me. But it took me more than a couple of weeks to realize it.

Charles didn't know it when he entered my life, at how new being a girl was to me. I had been in a relationship with a woman, Leeza, right before we met. It was boring and so unsensual. I ended it when I realized how little I actually liked her, and how little she liked sex. Dressing as a woman was so much more exciting, if I only had that, even alone, I would be fine. Right after I broke up with Leeza, and right before I met Charles, I decided I would start dressing full-time.

It was the beginning of April when Charles knocked on my door. I was surprised, I was waiting for Jason and Eddie and wasn't expecting a man. He took me out to lunch and showed me off to all the other customers. He wanted to introduce me to the world but I wasn't really ready yet. I didn't even think I was ready to be introduced to a MAN let alone the world.

***

"What's the plan for tonight?" I asked him between kisses.

"I was thinking some wine. I ordered food from Marchella's too it should be here soon. But first I want to see this outfit, how can you look so amazing every time I see you?"

I stepped back and gave him a little twirl. My pantyhose was barely white and I could tell he loved it. I put my hands on my hips, my long pink nails close to my exposed belly, and I pouted. He loved that. I would make believe I was sad and it was his job to cheer me up. Once I met Charles I was never sad, usually, I was overexcited and sometimes ecstatic but never, ever sad.

He handed me flowers. "These are for my big girl." My smile came back. He then hugged me with the flowers between us.

I shifted on my heels, "Okay go pour some wine, I will put these in water." And I minced away in my Pleaser heels, one hand up to keep my balance.

He was on the couch as I walked in and slipped on his lap. He was so big and I felt so dainty against his body. "What time are we leaving tomorrow? I asked.

"We can leave at noon. Are you sure about this?"

"I am, the boys need a surprise they have been gone for almost three months, and I miss them so much."

We were going to pick up Jason and Eddie at the airport. They were coming home from Florida where they spent their last semester as high school students. They left men, hopefully, they would come back not so sunburned, and even better men.

He kissed me on the lips, "You are such a romantic, you know that?"

"Mmm, I do. Now start being romantic yourself." Charles had his hands on my breasts when the food arrived. We ended up back on the couch after, I didn't mind cold Italian food but I had to have my man hot.

***

We were in Charlie's Jeep, I was sitting in the passenger seat wearing a black faux-leather miniskirt and a sleeveless off-white lace top. I had on nude thigh highs and my nude six-inch pumps. You could just make out the top of the elastic from my stockings when I sat. This was my type of outfit for the rest of the world, I was always feminine but never trashy. I had to learn, now that I was with Charles. I had on big gold hoops hanging low below my hair, and my lips were dark red matching my long nails. I was dressed for a day out, I was dressed to see my boys again.

We had two stops to make before we headed to the airport, we had plenty of time.

***

We were at gate twelve waiting for Jason and Eddie, the flight was a couple of minutes late and I was looking over people's heads to see if I could spot them. I saw their smiles before their eyes and they rushed up to greet us. Of course, they grabbed and hugged me first, I discovered I was always the priority with them.

"So glad to be back," Jason exclaimed.

"And I'm so glad you picked us up. I missed you." Eddie kissed me and smiled.

"Well," I said. "I have a little surprise for you, let's go get your bags." And with Charles and I in the lead, the boys followed. Hopefully enjoying my long legs.

When we first got to the airport Charles and I scouted out the area. We found this nice quiet lounge, with lots of places to sit and stretch out. There was almost no one here and it was well out of the way. No passengers even passed by. This is where I wanted to bring Jason and Eddie.

"This way gentlemen." I turned and looked at the two of them. They did change a bit. I was happy for them, they were becoming real men. They both seemed taller and stronger, and they both had immense smiles on their faces, they really didn't know what was coming.

We made one more turn and slowly walked through the sliding doors.

"Jason!" Amber yelled and ran to him. Monica did the same to Eddie and the four of them were hugging in the quietness of the lounge.

Amber and Monica were their girlfriends. I know they had a little too much fun down south but now it was time to start working on a relationship. The two girls absolutely adored their boyfriends, and now I made them get dressed a little sexy for them. I'm going to bet they have never even seen their girlfriends in heels or a skirt before. There was so much testosterone and estrogen in the air, and so much kissing going on that I grabbed Charles and we did the same. I ground into him, he was so hard, he wouldn't last long.

***

After everyone was taken care of back in the lounge, we headed to the parking lot.

The four of them were in the back of the Jeep. I could tell the boys were happy. The two girls' skirts were so short and the two of them were almost on their laps, bare legs over bare legs. Charles didn't know, but I knew what growing boys wanted.

***

We dropped the kids off at their respective houses. I actually have never gone into Charles and Jason's home before, I was too embarrassed. Charles was constantly inviting me over but I felt funny about it. I was afraid his other kids would come home to visit and I would have to explain who I was. I didn't want to be put in that predicament.

His wife has been gone for two years and I heard through the grapevine, actually the cleaning woman Rene we both shared, that the kids weren't ready for Daddy to start dating someone much younger than him. Besides Jason, he had a set of twins Roger and Rachael, and the eldest Teena. All of them except Teena were slightly younger than me. They were all married and out of the house but visited once too often. Sometimes they would come and stay for the entire weekend.

"You would love my house." Charles would tell me. "My backyard is like a resort, you could sit by the pool and pose in your bikini."

"I don't have a bikini."

"No?" He looked at me and smiled. "Well I have a cabana at home that is full of them, I still have all of my wife's clothes too, they are clean and in plastic tubs and I would love if you went through them." He told me she liked to shop.

"I don't think your kids would like me to wear their Mother's clothes." Even though I used to love to wear mine. My mother had excellent taste in bras.

"Well one day you are going to have to meet them, and all of you are going to be very happy about it. Whether you all like it or not." I gave Charles a pout, it was the first time I ever gave him a real one.

***

On the other hand, I was very happy in my Condo, I never had to leave. Having a boyfriend around to fix and change things was a godsend and everything was now exactly the way I wanted it.

I had so many men over the last couple of months hammering and putting up shelves, and that's not a euphemism. The biggest change of course was the balcony, but my bedroom also got an overhaul. I now had a huge walk-in closet, all my shoes, and accessories right in the middle, and then two open areas on both sides with all my clothes. I also had plenty of room for more.

The closet is so big that Charles and I have had sex in it numerous times. He told me it was a good idea to explore different areas of the Condo, to work out kinks and christen them, and see if I needed to upgrade. I remember blowing him when the construction team was working on my living room. I know they heard our moans while they banged away on the walls. When he first suggested it I was apprehensive, I wasn't interested in sharing our love life with anyone.

I had an island in the middle of the closet and I would make Charles sit on top of it. It was the perfect height now.

"There are men only a couple of feet away." I would tell him a little nervously.

"Yeah? So I've been told." He would smile, his pants starting to retreat down his legs. "They won't mind."

First I would change into something sexier, Charles accused me of trying to turn on the working men with my outfits so I was a little more subdued when they came. I slipped on a velvet coca mini dress and matching heels. I would lean my ass into him first to make him harder and let him feel my hose. My pantyhose was tight and silky and made me feel incredible as I watched in one of the mirrors that were scattered around the closet. He would grab my hips and push me against his now hard cock. I loved the feeling of him rubbing against me. It made me so happy to know that I had a man I could just call to come over and let me suck his cock, or do anything really. All of these years denying that this was what I needed. Eddie and Jason's visit's made me love cock but it was Charles that made me love everything else.

I was so ready to move on. He came into my life at the most appropriate time.

I would turn around and then slowly pull down my dress. My very real breasts would bounce in my lace bra and I knew he wanted to get his hands on them. Just looking at him, excited to see me was enough to bring me to orgasm but I liked to wait until he came in my mouth. I would lick his cock 'til it was smooth and slimy. I then backed up and held my breasts together and slipped his cock under my bra sliding his hard-on between my boobs. The bra would keep it in a perfect position to start the mammary intercourse. They were big and firm and I was quite proud of them. I would lightly squeeze my boobs, giving his manhood the perfect amount of pressure, feeling him get harder and closer to my chin. I had to exert so much willpower to not start sucking him right away.

Before Charles could come all over my breasts I would then stop and take him into my mouth. I always wore Color-Stay lipstick so as not to get his cock rainbow-colored. I would push my lips and tongue against his now throbbing cock, catching his face in total ecstasy. Charles knew he never had it so good. His last couple of girlfriends were friends of the family and didn't know a thing about how to please a man. They still call him, one of them threatened me over the phone, she sounded nice.

As I brought him into my mouth and tightened my lips around his cock he would rub and play with my hair. Through the sound of drills and hammers, he would come streaming in my mouth. There was always so much cum but I would swallow it all, and then MY orgasm would hit. I never had to get untucked or even touch myself, just being in close proximity to his massive cock was usually enough for me. I would lick him clean as he would moan as I was finished up playing with his cock. I would then kiss his manhood one last time, a little thank you and wrap him back into his pants.

Then we would leave the closet in the pandemonium of the banging. I'm sure all the workmen knew. I'm almost positive Charles would tell them. Plus I always forget to change.

***

"Is there anything that you would like to do? maybe something you haven't done in a long time?" Charles was asking me.

There were so many things I would like to try and do, but Charles loved to take me out of my comfort zone and that's what made me worried. When I lived in New York City I used to love going to concerts, but being surrounded by thousands of people while wearing heels would make me uncomfortable. Going to a Broadway show and sitting next to other people for two-plus hours also would make me a little leary. I still wasn't comfortable talking to those I didn't know very well. He knew that but he was trying to change me.

Charles kept on asking me for some new goal, and I knew I would have to come up with something soon, otherwise, he was going to invent one for me.

I felt silly telling him my biggest thrill was trying on clothes and posing in the new mirrors he installed. I spent most of my free evenings putting together outfits and working on my makeup and hair. I could spend days on new looks and playing with color combinations. And I was always taking all sorts of pictures and videos. I had some collection on my computer.

Jason and Eddie always wanted new pictures of me but I stopped giving them any once they headed off to Florida and I started dating a father. I was in a mature relationship now, my first. Charles got most of my sexy pictures, but I know he was happier with the real thing.

When the boys were away I would send them pictures of their girlfriends. I would take them to the park and together we would pose in front of the various landmarks. Three girls all dressed up in Northern Pennsylvania was a rarity and we tended to get a little crowd around us. Amber and Monica's wardrobe became a lot more risque after they met me. I had the boy's old camera, and the video and the pictures themselves looked amazing. Afterward, the three of us would go out for lunch and decide which pics were going to find their way to the boys and Charles's inbox. I loved hanging with my girlfriends. I was only six years older than them but socially we were the same age. In my head, I was a teenage girl.