Becoming My Sister Pt. 06

Story Info
‘Aimee’ goes further down the rabbit hole...
2.9k words
4.77
12k
24

Part 6 of the 10 part series

Updated 01/21/2024
Created 11/30/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Chapter 13

As I felt Jim's cum flow down my throat I shivered with pleasure as I looked up at him. He was smiling down at me as he scooped his cum from my chin with his finger and offered it to me. My eyes closed as I slowly sucked his finger, all the way down over his wedding ring, cleaning it before looking up at him, practically begging for more. I took his slowly softening dick in my right hand and licked round the now ultra sensitive head which made his body convulse with pleasure. I hoped my makeup wasn't too ruined but I had a feeling he wouldn't mind given what I had just done but knew he would want me looking perfect again very soon!

"That was amazing, Princess," he moaned as he stroked my pretty young face. "One of the best blow jobs i have ever had. You're a very very talented girl for one so young," he continued. I moaned with pleasure and entwined my fingers with his other hand, wanting him to feel my false acrylic nails on his skin. "Did you enjoy sucking me?" he asked.

"Oh, fuck yes!" I said enthusiastically. "You have a beautiful thick dick. I loved how hard it was. It tasted of...experience! And your cum was delicious! So much of it too! I've been a very lucky girl in the last 24 hours. Brad was good but you...oh wow...you're so gorgeous...my perfect man, my Daddy," I moaned as he took my hand and helped me to my feet. It was so amazing to me that I was still fully dressed and he was completely naked. He held me in his strong arms and we kissed deeply in front of the big mirror, our hands all over each other....Daddy and his new blonde Princess!

He said he needed the bathroom and I used those couple of minutes to redo as much of my makeup as possible, focused mainly on my lipstick. 'When did you say your parents were back, Aimee?" he asked when he returned. He noticed my redone lipstick and by his look I knew he really appreciated my effort to look good for him. I resolved that I would never leave him in any doubt that I'd always make maximum effort for him.

"Not until Monday," I said noting that it wasn't even 1.00pm on Saturday yet and I already swallowed a nice load of cum and was sure there would be more where that came from! Is this what happened all the time when you were a girl? Of course I knew that it was so easy for girls to get sex whenever they wanted it and pretty much from whoever they wanted it! Most men were dogs and would happily fuck anything given the opportunity. Oh god, could I get sex from any man I wanted? Well, probably not but I reckoned that if I offered a blow job there would be few men who would turn me down if I made the effort to look my best! Jim had totally given me the confidence that I could 'pass' as a girl and I was so grateful for that!

"So we have plenty of time to get to know each other even better, if you want that?" he said as he ran his eyes all over me. "Tell me, Aimee," he said his voice now much more dominant in tone.

"I'd like that very much," I purred unable to resist, the feminizing effect of his male cum on my mind becoming more and more apparent. All I could think about was the pleasure that I could give him and that his thick, hard, older dick could give me. I was acting like a bitch in heat and could feel my tiny thong was slick and sticky with my precum. "But what about your wife? Won't she be expecting you home soon?" I asked and then wondered if I should have mentioned her. All I wanted was to know if I'd have him for just another hour or so or for longer.

He cleared his throat and beckoned me over to the chaise-long at the foot of my sisters bed. He had me sit on his knee with his arms around me. It made me feel just like a real girl! "I can sense your concern and you're thinking that you wished you hadn't mentioned my wife? Right? Don't worry, Princess! Errrr...how shall I put this...my wife and I have come to an arrangement. She is fully aware of my 'tastes' and I am of hers. The young guy who cleans our pool is due round this afternoon so she will be 'busy' with him for most of the day and most of the evening too probably. He keeps her happy and off my case and she enjoys spoiling him with my money. It's a win win situation for both of us."

I was a bit shocked at how matter of fact he was about their arrangements even though they were married. But he explained that in public they are the perfect couple and both act out that role dutifully. No one had any idea that they live almost completely separate lives in private and haven't shared a bed for years. He said his wife would never leave him as he is the wealthy one and she has got too used to the life of luxury he provides for her. And as long as she gets an unlimited credit card and as much younger dick as she wants she is happy with that.

He explained that left him free to have his fun...and although he didn't say it explicitly, that meant beautiful younger sissy gurls. He said he mainly used escorts and had had a couple of longer term arrangements with them but that he now wanted a bit 'more' in terms of a relationship and had been looking for the 'right one' for some time. He looked into my eyes and asked me, "Would you consider being 'the one?"

I held his gaze as my stomach turned delightful and exited somersaults at the thought of being his 'girl'. I bit my soft red lip and asked, "Are you sure I'm what you want? Am I pretty enough? Girly enough? Sexy enough to please you? What about Brad?"

"Yes, you are totally and exactly what I've been searching for! And don't worry about Brad. He knows the arrangement his mom and I have. We give him such a big allowance he'll forgive us anything. Why do you think he didn't want me coming over here today? He probably knew exactly what would happen when I saw you!" he said reassuring me. "He's probably off spending my money on some expensive hookers to prove to himself he's not gay after what he probably did with you yesterday! And he still has your sister doesn't he?"

I giggled at his comments about Brad and he kissed me softly. He said, "I've been thinking about this for soooo long. I have soooo many things I want to do with the right girl. It's all mapped out in my head...all I need is a beautiful, young, slim blonde girl to join me on the journey! I can guarantee you won't regret a single second and you need never worry about anything including money ever again! I'm not sure you realise how wealthy I am and you don't really need to know...but let's just say if there is anything you want, and I mean anything at all, you only need to ask and it shall be yours."

"Sounds wonderful, and I want it more than anything," I said softly. The first things I thought about were all the beautiful, expensive sets of designer lingerie, dresses and high heels I'd ask him for. And then the time and space to be able to live like a girl 24/7 and have a good looking man to appreciate me and the effort I made for him. That is every sissy's number one fantasy and I was on the cusp of having that dream become a reality! I dragged my nails over his body and dropped to my knees between his legs.

Chapter 14

Before I could take him into my hungry grateful mouth he stopped me and said, "Let me see your beautiful body in all its glory," and reached down to make me stand. "Show me what I have to work with. Don't be embarrassed about anything. Show me everything you have," he said eagerly.

I stood and looked down at him and turned so he could unzip the tight black dress which I slowly pushed down, wiggling my hips to work it down and over my thighs. I heard him moan and then felt him softly kiss my firm, pert ass and along the thin lace straps of my thong. I stepped out of the dress and unhooked the bra which I casually threw to the floor and turned around to show him my slim, smooth body. I knew he would be disappointed at my lack of breasts but he didn't show it and pulled me towards him to kiss my toned stomach as his hands pushed my thong down. My soft, shrivelled but leaking dick fell free but he didn't touch it. Instead he lent forward and undid the straps of my wedge heels and removed them.

"Turn round for me slowly," he said, "Let me see you. Oh Jesus you have sooooo much potential," he moaned as I slowly did as he asked. "You're the perfect blank canvas on which I will create a masterpiece for the whole world to admire," he said as he led me by the hand to my sister's bed, his big thick dick standing up so proud and erect for me!

We climbed on to the bed and I could feel his hardness flick over my limp dick before it pressed on my flat stomach. As we kissed deeply before he shuffled round behind me, his experienced fingers stroking and caressing me. "I need you to be completely naked for this first time," he said. '"In future you will always be dressed up for me but I like to start this way and then turn you into the goddess I know you want to be for me!" I felt him rub his hardness over my ass cheeks and then he laid it on me as he wrapped his strong arms around me and kissed my neck. "When I've finished your transformation there won't be a man alive who wouldn't want you in their bed!"

I tensed as I felt his head press against my pussy. He stroked me and told me to relax as I felt his weight press forward just like his son had done yesterday. I cried out as I felt the head pop inside me, stretching me wide as I heard his moans of pleasure as his shaft slid slowly inside me. I could tell he had so much more experience than his son. The way I felt him circling his hips slowly, so that he opened me up and stretched me sooooo deliciously. I tilted my head back, my back arching as he gripped my slim waist and gently began to pump his beautiful married dick in and out of my 18 year old body.

"Oh, fuck! You're soooooo big," I moaned. "So much bigger and thicker than your son. Please don't stop," I begged as I pushed myself back against him. I heard him moan out loud and hoped he loved my dirty mouth. Encouraged I said, "You fuck so much better than Brad. I bet you can go all night too. I hope you can because I need a man who can fuck me from sunset to sunrise." The rhythmic slapping of his balls against my ass was amazing and I felt his strong, experienced hands all over my body...stroking, squeezing, caressing, exploring me as his perfectly timed strokes opened me up over and over and over again.

"Your body is perfect," he said as he drove his hard dick into me. "So soft, so young, so tight...my dream come true," he almost growled as he slowed his strokes. Long, slow, intense, deliberate strokes...each one must have taken 5 seconds to enter me and then 5 seconds to slide out, leaving just the head inside me before he re-entered me, making me gasp with pleasure each time. OMFG! This guy knows how to fuck I thought to myself, I'm such a lucky girl to have met him! I moaned as he pushed my face down into the pillow, his hips circling round to stretch me one way then the other. I felt him lean forward and press his chest on my back as he kissed my shoulders, lifting my long blonde hair to gently bite my neck, his strokes still perfectly timed to meet my response.

He lifted my head and turned it to kiss me. I moaned as our tongues danced and then I said, "I love that you're married." It was like he read my mind as he moved his left hand round so I could kiss and lick his wedding ring.

"Maybe I'll give you one of these for yourself one day, if you're a very very good girl," he said teasingly before pressing hard and deep inside me. The thought of wearing a wedding ring and his deep long stroke sent me over the edge and my still limp dick spilled its seed all diwn my thigh and over the bed sheets, my body shaking with pleasure as he slowly fucked me. "You like that, Princess? Like the thought of being my young blonde trophy bride?" he said and I could sense the excitement in his voice too.

"I can see you now in a beautiful, classy, elegant, white gown approaching the altar nervously as everyone looks on thinking how beautiful you are! The white flowers in your amazing light blonde hair..the sound of your beautiful 5 inch white Jimmy Choo heels clicking on the stone church floor. Your soft delicate hand shaking as I slide a 24 carat white gold wedding ring on your finger, over your bright red nail, resting against the big diamond engagement ring I bought you. Then taking you to a luxury 5 star Caribbean resort for our honeymoon where I will totally show you off to everyone! Imagine the looks you will get...all the other men who are jealous of me...all the other women jealous of you when they see your beautiful expensive dresses, heels and jewelry...all this gorgeous local black guys who would do anything to fuck the beautiful young blonde trophy bride! Do you like the sound of that, Princess?" he said as his perfect strokes drove me crazy! "My beautiful blonde teenage bride. God, how I'd love you to take my wife's place and give you everything she has," he moaned and I felt his strokes reach a new level of intensity, his fingers digging hard into my waist before he cried out in ecstasy and I felt his cum shoot through his rock hard dick deep into my young body over and over again. It would seem that the thought of taking me as his young, blonde, trophy bride excited Jim as much as it did me!

Chapter 15

A couple of days had passed since my amazing first meeting with Jim. We had been texting regularly and they inevitably ended up being totally erotic...I loved how he talked to me and treated me like I was 100% a real girl. On Wednesday a small parcel arrived for me which I signed for. I didn't recall ordering anything and when I was in my room I opened it. OMG! It was from Jim and in it was an American Express card in my name with a $10,000 limit, a new IPhone and a set of keys for a swanky apartment block in the city. There was also a note from Jim telling me wanted to see me tomorrow evening at the apartment in the city and that I should go there in the afternoon. He would then pick me up at 7.00pm and take me out to dinner.

OMG! This was beyond my wildest dreams! I'd obviously never had such a lot of money. There was already a text on the phone which read, 'Hi Princess, hope you like! See you at 7 tomorrow xxx'. I excitedly texted Jim to say thank you from the new phone. He was very matter of fact about it and said it was what I deserved and how his girl would always have the best of everything! That made me feel so good. He said that the card was just to be used for make myself look and feel good, both for myself and for him. There were a few things at the apartment I might like but if there was anything else I needed then that was what the card was for. He said he'd sent me an email with some helpful details. I opened the email app and there was an email for 'Princess_Aimee@hotmail.com'...my new email address! Wow!

In the email were a list of stores where I could shop for lingerie, dresses, shoes, makeup, a nail and hair salon...everything a girl needed to look good for her man...and that if I asked an assistant in every store for help and said that 'Jim has sent me' they would be incredibly helpful and that there was no need for me to be hesitant or embarrassed about buying girly things! OMG! I'd always fantasised about being able to go and shop like a real girl rather than have to buy things on the internet because it would be too embarrassing. Now my dream could come true!

To be continued....

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
Tinnie2024Tinnie20243 months ago

I am normally a man of very few words, I normally don’t comment On the stories that I read, but I must say I have absolutely enjoyed reading these stories about Aimee and her journey

K_stone19K_stone194 months ago

This story is so hot. Please keep writing it. Part of me wants for Jim to pay for her to get implants and hormones and the other part just wants her to stay how she is. Can't wait to find out 😉

Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Man That Converted Me A young man is snowed in & turned out on a mountain getaway.in Transgender & Crossdressers
Becoming Mommy Ch. 01 I was just going to meet my girlfriend's family.in Transgender & Crossdressers
Comforting Pete Consoling friend reluctantly agrees to help in other ways.in Transgender & Crossdressers
Eric or Erica? Pt. 01 Eric is saved from near death but his rescuers are different.in Transgender & Crossdressers
A Sissy for A Bridesmaid His sister needs a new bridesmaid, and the dress fits him!in Transgender & Crossdressers
More Stories