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Introduction:

Nikki meets a man who she thinks is the one to bring out her sissy side and decides to meet him in person

I had been on the chatrooms and fetish sites for a while trying to find that special someone who could bring out the real me.
The 'me' everybody saw was a 20 year old student with brown hair blue eyes and a stature a little smaller than average and unfortunately a little chubbier too though it gave me a nice smackable ass
I would occasionally get an unrelenting urge to put on girly clothes and become Nikki my female self and because Nikki is a slut it would usually end in the usual self-loathing post ejaculation. Though up until that point it was great fun. I would usually toy my ass with increasingly thicker items from around the house and when the opportunity was available I would cam for gentlemen I liked through Skype. I would start these sessions in full gear; bra, panties, stockings, miniskirt, girly top and if the mood strikee high heels as well. All carefully borrowed from my female family members. The sessions would usually end however with cum on the gentlemen's webcam and me in a bra and stockings with one foot on the table my cheeks spread and a toy deeply embedded inside me. I'd love hearing their moans, dirty talk and affection for me.

This is how I found my special someone. We met on a fetish dating site and got to talking. He was in his 50's but a real stud. The more we talked the more I realised he was perfect for. He wanted a long term sissy to feminise, had connections to help me explore my sexuality and liked the idea of me calling him daddy which is one of my mindless moans during toying.

We got on so well and it turned out he only lived 10minutes or so away, I couldn't believe it. We talked for weeks and i played on cam for him a few times though I was reluctant to meet. Its a huge step to make, to me this was all still fantasy and I wasn't sure I was ready for a man to make me his sissy in case I wanted the normal life someday.we spoke about this and he told me we didntnhave to do anything just keep what we had and this made me feel he was the one even more.

After one particularly active session we were both exhausted and just talked. Eventually we got on to the topic of meeting and whether it was just right or the toy still inside me was making me feel all sissy i agreed it was time. We booked a hotel room in the city centre near the top floor to give us a romantic view. When I mentioned clothing he asked for my sizes and said he would take care of everything

The day before he sent me an email telling me when to arrive at the room and where to find the key. I was instructed to strip in the hallway and proceed to the bathroom where I would prep myself for the night and find my female attire. I was so excited I had my toy inside my ass within seconds and proceeded to cum all over the floor while in doggy position, I licked it up because I felt that's what daddy wouildve wanted of his little sissy

The big night...
I arrived early because I was so horny and went through to the room. There was a chair in the hallway with a note pinned to it to remind me to leave my male clothes on it and go to the bathroom so I obeyed
In the bathroom was a container of hair removal cream and an ready made enema which was still warm. I was worried there was no clothes and that I had come to early but I trusted him so I started with the enema because I thought it would be the mood-killer and the hair removal might perk me up. I was right, couldnt keep myself from touching myself all over afterwards. When I stepped out of the shower I was surprised to see a bag I hadn't noticed before and realised daddy must've came in while the shower was running. I got hard knowing he was so close by. On top of the bad was a list of items and the order he wanted them put on or in the case of the first item.....put in. It was a medium sized buttplug that from the looks of it vibrated though I couldn't find the switch anywhere and figured it must be remote controlled. I lubed it up and slowly worked it inside myself gently moaning. I was about to grab the bra which was next when I felt the sudden vibrations radiate through me and bring me to my knees. After I regained my composure I guessed he could see me dressing and thought I would give him more of a showI picked up the yellow Lacey panties and bent over and slowly slid them up my legs and settled them in place. I pushed my little balls inside me and moved my clit as daddy liked it called into place between my legs. I then put the matching bra on and it seemed like it was sculpted for me. It pushed my chest in to create sizable cleave at least a B cup. Black stockings were next and they felt magical on my hairless legs I could feel tingles running through me. Daddy wanted my heels on next. Omg I couldn't believe how cute they looked. They were a shiny red with a 3 inch heel. Once they were on I admired myself in the mirror briefly. Daddy has made me look better in 20 minutes than I managed in all my years. I must've taken too long admiring because I felt a sudden vibration that went as quickly as it came just to remind me he was waiting. Next up was a knee length black dress with a dipping neck line to show off my new cleavage. I slipped it on and smoothed out the dress before finishing up with a long hair wig in dirty blonde. Once again he had it perfectly sized. I could never have imagined how feminine I could look. I wasn't able to hold back any longer so I rushed out

Daddy was sitting on the chair now looking directly at me. I saw a smile spread across his face
"Nice to finally see you in the flesh Nikki"
"You too sir, thank you for these clothes"
"That's OK sweetie, I'll be getting my moneys worth out of you. For starters a simple trade"
"What do you mean"
"I've placed your male clothes in the rooms safe, its one of the keys on this chain" he held up a delicate chain with 3 keys on it
My heart was beginning to beat. This man had me trapped en femme now with no way out. "Can we take them out?"
"No sweetie sorry. At least not until the uses of all 3 of these keys have been revealed to you, lower your panties"
I hesitated out of nervousness but one glance from him told me I was his so I did as told. He stood up and came close to me and kissed me hard on the lips. His tongues invading my mouth, melting my resistance. He reached under my dress and grabbed my male bits
"I'm gonna lock these away in a cage, youre gonna be my sissy sweetie tonight and I don't want you to get any ideas of manliness"
He must've practice's the movements beforehand or been very experienced because the cage was on in seconds and the second keys use was revealed before he slid the panties up my legs back into place. I could swoon from this amount of domination"Sweetie its time you learnt how to suck a cock, unbuckle me"
My nervous hands went out and fumbled with his zip and freeing his hardening cock. I'd seen the photos but it was nothing compared to this 7inch and thick sculpture of masculinity. I leaned over and kissed the tip gently just to satiate my curiosity and was overwhelmed by all these new experiences and had what felt like a mini orgasm inside my abdomen. I breathed out slowly and took him into my mouth. I had been practicng four years or cold unforgiving objects but they couldn't compare to his warm relenting piece. He moaned and placed a hand on the back of my head.
"Good girl, I see all those lessons on webcam were well spent"
I hummed around his cock and moved my head back and forth while gripping its base. I was frantically roving my tongue over his helmet stimulating it all trying to ring a trigger point for him and then I found it. At one point just at the top of his helmet his moan grew louder and his grip on my head momentarily tightened. I pressed forward focusing on this point till he tightened up and spilled his load into my mouth
His fave was slightly contorted but I could see his smile spread like his orgasm. He let of my head and o went back on my haunches. I looked up at him and smiled revealing the cum in my mouth before swallowing it
"Little slut" he bemused
I had tasted my own cum but his felt better, maybe it was just the effort needed to receive it.
He collapsed onto the chair resting his elbow on its armrest and his face in its hand. Looking at me like I was for sale.
"Take off the dress and bra, I have a corset for you"
I couldn't take off the dress fast enough. He placed the beautiful black and pink corset on me with its attached short pink frilly miniskirt. He went to the back and pulled the laces. Oh god was it tight but it raised my bust till it looked like a respectable C cup. I then heard a click and a jangle of keys, I had forgotten the third key
"What was that daddy"
"Just a lock sweetie, you can't be released from this corset now unless I allow it"
"Daddy I'm a little scared"
"Don't be, I'll take care of you" he brushed my cheek with a finger.
"Lay on the bed sweetie"
Wasn't long on my back before I felt gentle cuffs placed on my wrists and then I knew I was all his. He walked to the phone and spoke so softly I couldn't hear, not long after a rap at the door and he disappeared. He came back with a satisfies smile
"The plans underway honey. I just gave the key to room service and told them to post it to my house, should be a few days. I have spares of course but they're at my house already. In other words you're leaving here with me tonight"If it wasn't for the chastity cage I'd have been rock hard. He was perfect for me, I had made the right choice.
"I'm not sure if I should go all the way daddy but I need it inside me, I'm desperate"
"The perfect little sissy then" he smiled
"Will you put it in then decide what you want. If you want to keep me then take me otherwise pull out, I just need to have felt a mans cock in my ass"
Daddy stood up and stripped naked. He moved towards me and kissed me hard before reaching into my skirt and pulling my panties down my legs. This was the moment I had been waiting for. He gripped the butt plug and slowly worked it out of me. The slowness was exquisite agony, I could savour all those sensations.
"You look beautiful sweetie"
I felt a warmth I've never felt. To be wanted sexually was something I hadn't known in my life till now and I loved it. My ankles were raised and placed on his shoulders. His once again solid member was lubed already and placed against my virgin entrance.
"Daddy wait"
"What's wrong sweetie?"
"This is such a big moment, I'm scared to through with it"
"That's why you chose me, I'm not"
my entrance gave way, he slipped inside me. That glorious warmth spread through me. I couldn't hold it in me and moaned so loudly and shockingly to myself very femininely. I was loose enough from the butt plug that he was in me to the built within moments. The moment had come. I opened my eyes and looked into his. He knew as well it was either take me as his forever or leave now and go our separate ways.
"I love you daddy"
"I love you too sweetie"
He kissed me gently and started moving out of me. I was about to speak just as helmet was about to pull out and it started gliding back in. I was beaming with happiness. He started slow. Removed the cuffs and picked up the pace. He leaned in close and I placed my arms aroundnhim to hold him to me as he plundered my insides. I was moaning like a slut
After a fe minutes of this his breathing became heavier and I sensed he was getting close to finishing.
"Breed me daddy, make me yours"
Between ragged breaths he spoke" you're already mine.....I'm just marking my territory "
It was then I could feel him fill me up. It was a new, welcome and hopefully soon to be repeated experience. There was so much in me by the end that when he removed himself I began to leak. He quickly corked me with the butt plug like a wine bottle.
I lay there spent but somehow he had the energy to move. He started to get dressed and halfway through he threw me a pink dressing robe.
"What's this for?"
"Put it on were leaving to go home"
"I can't leave like this people will see me"
"You look so beautiful no one will recognise you as male. The dressing robe is to protect your modesty. In case you've forgotten you have no male clothes so you're leaving here somehow. Best with me sweetie" he smiled a slightly sinister smile.
I couldn't deny he had me trapped and with his cum inside me I felt like i was his. I wore the robe and we quickly made our exit. I was as nervous as hell until we made it to the elevator. Though we would have a long ride down I knew at this time of night no one would interrupt us and see me. I might just make it out unnoticed. Daddy pressed the button for the ground floor. Just when I relaxed he grabbed me and removed my robe pressed a button for a floor near us reached under my skirt and removed the plug again and threw it out the doors before eshutting them again.
"What the hell?"
"Sweetie you're a sissy. You had better get used to people exploring your filthy side"
His cum was once again running down my legs. I moothee the mini skirt as low as it would go which wasn't far as we reached the ground floor. He placed his arm around me and manoeuvred me out into the lobby. The check in girl recognised me as I had spoken to her earlier. She smiled and winked and I could see her hand move under the desk and could only assume she was touching herself. Daddy opened the doors and ushered me outside

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