Becoming My Sister Pt. 05

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Things take an unexpected turn for ‘Aimee’…
3.6k words
4.77
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Part 5 of the 10 part series

Updated 01/21/2024
Created 11/30/2023
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Part 5

Chapter 9

As I looked up he turned around and what I'd first thought was Brad was in fact his father, Jim!!! OMFG! What the fuck was he doing here?

"Hey, Aimee," he said as he turned around. I could see the surprise on his face and of course he knew instantly it wasn't his son's beautiful girlfriend. And I knew that too! I watched as his eyes moved from my face until he was looking me up and down. A few moments before I'd been reveling in how I looked and enjoying my femininity knowing that Brad accepted me for what I was. But now I'd never been more self-conscious about all the things I'd just been so confident about!

After a few of the most uncomfortable seconds of my life a broad smile replaced the previous puzzled look on his face. I think he must have figured out who I was and what was going on between me and his son! OMG! Now there was someone else who knew my secret! Until yesterday evening this had been my own private fantasy world which I could escape to. Now there were two others who knew my secret! I was cool with Brad knowing as he had treated me nicely but his Dad maybe totally different and as he was older less accepting of what I was. What did his smile mean? Was it a mocking smile? Did he look at me and think how ridiculous I was? I had the answer almost immediately and it wasn't what I was expecting!

I was stunned as he just continued as if I was Aimee! Was I dreaming? Surely he knew I wasn't the 'real' Aimee? Was Brad's father just mocking me before he burst out laughing at me? I'm sure my jaw dropped as he said, "Brad said something had come up and he can't meet you now like he promised. He dropped his phone in the sink and it's totally screwed so couldn't text you as he couldn't remember your number. I was on my way out and said I'd be passing so offered to drop by and let you know. He told me not to and it didn't matter if he left you hanging. I couldn't believe that he could be such an asshole to you so I insisted. He was so mad when I told him I was going to drop by. I'm very glad I did now as I can see you're disappointed as you've made so much effort to look good for him. I'm sorry my son is such a jerk."

"Oh, ok, not to worry. It's so kind of you to let me know. I'm very grateful," I said with my disappointment so obvious. "He was gonna take me to lunch but I guess I'll go hungry now," I said smiling at his Dad. Jim must have been mid-40s but was still very good looking. I'd seen him a couple of times before but had never spoken to him. He still had a full head of hair which was greying at the temples and obviously worked out. He was 6'2" like Brad and equally well built. He had the confidence that exudes from successful middle aged men. Confidence was something that all girls including me found very attractive. As I looked at him I could feel my cheeks flushing red as I played with my hair and he returned my gaze and smiled at me. I quickly looked away...damn, how could I make it so obvious that I found him attractive!

"Say, do you mind if I grab a glass of water? It's so hot today," he asked still checking me out.

I came to my senses and still blushing said, 'Sure, of course. Come on in. My parents are away for the weekend," I said and then wondered why I'd even mentioned my parents. What was I thinking! I'd told this gorgeous older married man who had figured out exactly who I was and who was totally checking me out that I was home alone. It was like I was daring him to hit on me! How could I do that? I'd let his son fuck me yesterday and was due to meet him today. Now here I was flirting with the very next man I met! What was I like!!! I totally felt like I was betraying Brad!

"So, how are you enjoying college? Hope you're having some fun but also studying hard?" he said with a twinkle in his eye. OMG! He was continuing to act as though the real Aimee! A shiver went down my spine and I felt goosebumps on my arms at the thought of being treated like a girl by a man like this. I decided go play along as it was too exciting not to.

"It's great," I said excitedly flashing him my big white smile. "I've made some great new friends and although we study hard, we also party hard too! I've joined the volleyball team and it's cheerleading try outs next week!'

"Sounds like you're having a ball," he said as he looked into my eyes as he sipped the water. "I'm surprised you even bother to come back home given the way Brad has treated you and let you down today. If I was 20 years younger and you were my girl, I'd make sure you were treated like the Princess you obviously are," he said totally checking me out and not seeming to care that I noticed!

I giggled and pushed my long blonde hair over my ear as I reveled in the attention I was getting from this wealthy, older, confident married man! "So cute," he said.

I looked at him and said, "What's cute?'

He walked over to me and said, "The way you do this," and lifted his hand and pushed the blonde hair over my other ear. "I could watch you do that all day," he whispered softly. I felt my knees go weak as he touched my hair. This was the kind of male attention I always fantasized about. "So pretty," he said. "I totally see why Brad talks about you all the time. He's a very lucky guy to have you."

Chapter 10

At that moment I was incredibly conscious of everything that contributed to my femininity...the feeling of the bra gently digging into my soft skin, the feeling of the lace of my thong on my skin, the tightness of my dress, the straps of my wedge heels around my ankles, the taste of my lipstick as I subconsciously licked my lips, my long false red nails, the blonde hair that kept falling in front of my face...and equally conscious of everything that contributed to his masculinity...the deepness of his voice, the hint of stubble, the smell of his cologne, the expensive shirt with 2 buttons undone to show a hint of chest hair, his broad shoulders and strong arms, his wedding ring, the confidence that oozed from his every pore...

I looked up shyly into his deep brown eyes, my body trembling as his fingers tips moved from my ear and down my cheek. "Just perfect," he moaned as he lifted my chin with a finger. "Do you wish I was 20 years younger, Princess?" he asked.

"Isn't age just a silly number?" I replied totally flirting back at him.

I felt his other hand take my left hand and watched as he lifted it to his lips and kissed each of my red nailed fingers so tenderly and gently. "I couldn't agree more," he said and I thought my heart and head were going to explode as he leaned in to kiss me so softly and gently. I felt my body unconsciously move to press against him, my hips pushing up into his. OMG! Only yesterday I'd been in bed with my sister's gorgeous boyfriend and now it looked like I'd be going to bed with his even more gorgeous father!

Oh Jesus! Is this seriously what it's like being a beautiful young girl? Men of all ages constantly hitting on you? They don't seem to even care if they have a girlfriend or are married or about the age difference! Oh. My. God! All they seem to care about is getting you into bed!

I moaned with pleasure as I felt his strong experienced hands run down my sides before gently grabbing and squeezing my ass. I draped my slender arms around his neck as we kissed more deeply, our tongues dancing as our bodies pressed together. I felt his hand in my long blonde hair as I dug my long false nails into his back a little but being careful not to mark him as I knew he was married! I could feel his big hard bulge pressing against me and I loved that I was able to do that to him. "Show me your room," he moaned into my mouth and I eagerly pulled away and led him by the hand upstairs to my sister's bedroom knowing he was totally staring at my pert ass!

Chapter 11

As we approached my sister's bedroom, I felt his left arm around me and he bent down, wrapped his right arm round my legs and lifted me up into his arms. Instinctively my slender arms draped round his neck for security but I need not have worried as he picked me up as if I weighed nothing at all! I squealed with delight, my eyes wide and staring into his as he grinned and walked effortlessly down the corridor to my sister's bedroom as I softly kissed his cheek which brought contented moans from him. Oh god, he was so taking control of me like a total alpha male. This had all happened sooooo quickly and I realized that I just loved the feeling of literally 'being swept off my feet' by a dominant alpha male. It made me feel so weak and helpless and incredibly feminine and girly and my head was spinning with the thoughts of what this gorgeous older married man would do to me over the next few hours! He'd have waaaaaay more experience than his son and I was hoping he would share all that experience with me and teach me even more!

As we entered my sister's bedroom he gently put me down and I stood pressed against him in front of the big full length mirror. I turned my head and stared at myself in the arms of a gorgeous much older married man! Yet another of my biggest fantasies was coming true! "Soooo beautiful," he moaned as he too looked over at the mirror. "You look like you were made for me. Everything about you is just perfection," he said as my eyes closed and I bit my soft red bottom lip and moaned with pleasure at his words. I tilted my head back offering him throat as he kissed, licked and them gently bit it which made me shiver with pleasure and my red nails grip his hair tightly. I could feel I was totally leaking into my beautiful powder blue thong, staining it, but I was so happy that I was still completely limp! Again I wondered if that was what Brad's father wanted or would he want me to get hard? I'm sure I'd soon find out as he was so confident and would let me know exactly what he wanted!

I moved my fingers to unbutton his shirt and he looked down at my long false red nails. "Mmmmm, I wish my wife had nails like yours," he groaned as they undid another button and I dragged them slowly over his chest which brought more moans from him.

"I'll always have perfect nails for you if you like them that much?" I said in hope that this would encourage him to want to see me again but that was obviously dependent on how much I pleased him this afternoon.

"I'd gladly pay for them, if you would let me?" he said as he reached round to his back pocket, took out his wallet and threw two $100 bills on to the bedside table!

"OMG!" I said, "That's very generous," I said as I fluttered my long false lashes for him.

"Oh, I'm sure you're going to be worth it," he said slowly. "I think you should also get those beautiful lashes of yours done too," he said as he threw another $100 bill down. "And there's plenty more where that came from. I've been looking for the right girl to spoil rotten for such a long time. All of Brad's other girlfriends just weren't my type, if you get my meaning," he said in his deep sexy voice.

"I think so," I whispered in my sexiest girliest voice as thoughts of being spoilt rotten and showered with gifts of beautiful sexy dresses, shoes, lingerie and everything to make me look and feel as feminine as possible. I continued to unbutton his shirt and after the last one I slowly kissed down his chest, bending down to kiss his stomach before I got on my knees and looked up at his smiling expectant face.

I could see his big hard bulge sticking out and as I ran a red nailed finger over it very slowly, I looked up at him as I bit my bottom lip again. I watched him lick his lips, his eyes wide as he let out a soft sigh of pleasure. I fluttered my lashes for him again and moved my red lips until I was almost touching his bulge and slowly flicked my tongue out, dragging it all the way up to the end of his bulge. I felt his fingers in my long blonde hair and as he stroked it he said, "Mmmmmm, just perfect. A perfect blue eyed blonde Princess. I've waited soooo long and now I think I've finally found the one."

I moaned and then kissed his bulge through his trousers. He gasped as he saw the red lipstick staining his trousers but I just carried on and he groaned out loud and gripped my hair hard. My red nailed fingers moved onto his belt and I unbuckled it slowly, a smile on my face as I pulled down the zip and tugged his trousers down. They fell down around his knees and I then kissed up and down his bulge through his white boxer shorts. The kiss marks I left all over them looked so hot. I think Jim agreed as all he could say was, "Oh my fucking God, Princess!"

I giggled and I just couldn't wait any longer. I licked my red lips as I slowly pulled his boxers down and his hard 8 inch much older married dick sprang free...so hard, so proud, so delicious looking! I looked up at him and held it softly against my palm and pulled the foreskin back with my thumb as I gently squeezed it with my red nailed fingers. Jim moaned out loud as I slowly stroked him up and down, my eyes drinking in his beautiful dick, breathing in its scent...I could already smell his precum! I traced the tip of my tongue round his head, my beautiful red nails stroking his smooth shaved balls making sure I maintained eye contact with him, fluttering my lashes for him. "Next time you see me my lashes will drive you crazy," I purred as I kissed and licked all the way down to the base of his rock hard dick as I pressed it up against his stomach. My tongue lapped at his balls like a hungry little kitten lapping up fresh milk...I hope that very soon I'd be lapping up his delicious fresh married cum!

I kissed back up his rock hard shaft and paused with my red lips slightly open as I fixed my eyes on his. Then I slid my soft lips slowly over just the head, pulling back the foreskin so I could focus my gentle sucking on the most sensitive area. His head tipped back and he let out a long moan of pure ecstasy as my tongue lapped the underside as my lips worked over the top. All those straight male/female blow job porn videos I'd watched were now being put to use as I hopefully gave this gorgeous, wealthy, older, married man the best blow job he had ever had! It certainly felt like that as my fingers gripped his shaking thighs and his groans of pleasure filled my sister's bedroom. I wondered how often he'd looked at my sister with disappointment that she wasn't the same kind of 'girl' as me? I bet Brad had only ever bought 'real' girls home and wondered if yesterday was his first experience with a girl like me? It probably was but from how much he obviously enjoyed it I think he'd be thinking about it for a long time! Like father like son I mused as my young, soft, warm, wet mouth drove his father crazy!

Chapter 12

Slowly, inch by inch, my wet mouth slid down over him. My red lips stretched wide by his beautiful thickness. I gagged a little as I knew that guys loved that...it made them think their dicks were huge and I wanted to make every man feel like a King when I was with them! Especially this one! I moaned as he held my head firmly in place as saliva dripped over my chin. I looked down as he pulled out and could see my red lipstick smeared all over his hard, wet dick. I giggled as I flicked my tongue over it, licking my lipstick off him, cleaning him, before sliding him deeply in my mouth again. "Ohhhh, fuck yessssss," he moaned as he watched me lick the red lipstick off him.

I knew then what I should do for him. I stood up and walked over to my sister's dresser and reapplied my red lipstick and drenched my lips with shiny wet look lip gloss for him."Do you like this?" I asked as I moved close to to let him inspect my lips, pouting for him, making my eyes so big for him. "Do you like red lipstick?" I asked. "I bet you do. The brighter and redder the better? Look how it matches my nails! Does that make me look pretty? Or does it make me look like a slut? Matching lipstick and nails make me feel soooo super sexy," I purred. "Is that what you want me to be for you, Daddy? Your super pretty sexy slutty little Princess? Tell me what you want me to be for you," I said as I dropped to my knees again.

I could see the excitement in his eyes and the pre cum oozing from his dick as I looked up at him. "Oh yes, I want you to look like this for me 24/7, 365 days a year. I want you perfectly made up for me always. Your nails and lipstick should always match! Your eyelashes should always be long and false. Oh and I want you dressed up for me. Oh god, I want you dressed up for me! I want you to dress up and display your perfect young body for me. I'll buy you the most beautiful sexy dresses and high heels and then after you have given me a fashion show I want to take you out on my arm and show you off and display you. You're too perfect not to be seen and desired by other men. I want you to make them all jealous of me," he moaned excitedly.

This was what I'd always fantasised about. I would finally actually feel what is was like to be my sister. To dress up to display myself to men knowing that I would get so much attention from them. To know exactly what they were thinking as they looked at me and talked with me and flirted with me! And all the time I would feel safe and protected on the arm of a gorgeous, wealthy, older man. A man confident enough to take his girl out and show her off to other men...I would be his young, blonde trophy! Yes, yes, yes. Yes please!

As these amazing thoughts ran through my mind my soft shiny wet red lips slid soooooo slowly back over his beautiful hard dick. I took as much as I could, forcing my mouth over him until I left a bright red ring 2 inches from the base of his dick. As I pulled my mouth off him a thin string of saliva stuck out connecting my mouth to his dick. Oh fuck, I knew how hot that must have looked as I looked up at him. I was rewarded as he thrust his dick back into my mouth, held my blonde head and began to fuck my mouth, his balls slapping on my chin.

I felt and heard his breathing quicken and felt his precum begin to flow. I could taste more and more of its saltiness on my tongue as his thrusts became faster and faster. I dug my red nails into his ass and he let out a cry of pure joy as his beautiful, thick, older, married dick exploded, filling my mouth with delicious, warm cum. He grunted loudly with ecstasy each time his dick spasmed and shot more cum into my hungry eager mouth. I swallowed greedily. "That's it, Daddy. Fill my mouth, show me how much you want me, make me your yummy cummy Princess," I moaned as his cum spilt from the corners of my mouth, over my chin and stained the beautiful tight black dress I was still wearing...

To be continued...

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6 Comments
AlyssaPageQTAlyssaPageQT3 months ago

Your stories have made me want to become a girl more than anything in my life ever has, and i've been a closeted sissy for over a year now, embarrassed to admit it to anyone i know. I would completely give myself into being a girl for the characters / alpha males you show in your story. God I want to be Alyssa more than anything now.

SissyBoy1WarszawaSissyBoy1Warszawa4 months ago

In a very interesting way you develop the increasingly sexual aspect of Aimee's brother's life and changes, and the greater perception of yourself as a girl. Revealing the secret about his transformation to another person and, consequently, having another sex with a man and older - Brad's father.

What will be the fate of Aimee's brother "Princess Aimee", what other experiences will he gain and will he find his love? Will Aimee, the sister of "Princess Aimee", find out about everything and how will she react to it? Will she be very angry or will she accept that her brother is now her sister?

ps. Sorry for any errors and linguistic inaccuracies, I don't speak English.

SissyBoy from Warsaw, Poland. 👩🏻‍🦳⚧️❤️🧒🏻⚧️👧🏻♀️👨🏻.

AnonymousAnonymous4 months ago

Lingerie please!

AnonymousAnonymous4 months ago

Scrumptious

AnonymousAnonymous4 months ago

He falls down the rabbit whole fast.

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