I have to admit it, this is my biggest fantasy right now. The idea of getting this to happen in real life keeps playing in my head over and over.

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We stumble upon each other online and start chatting. It takes me a while to feel comfortable and open up for you. You’re my first and you’re patient with me. Willing to take it slow and help me be my true self.

After some time chatting online we meet and get to know each other, and once we feel safe, we set a date. Not a real take me out to the movies and dinner date, we book a hotel room. You tell me I’m not allowed to bring any boy clothes.

I keep a packed suitcase full of my sissy toys at my place. I grab my suitcase and head up to the hotel room ahead of you. There are none of my boy clothes in my suitcase. Only girl clothes, with all of my sissy toys and accessories, the things that make me feel pretty and feminine.

Once inside the hotel room, I rip off my boy clothes I was wearing, and hop into the shower. I quickly go over everything with a razor to make sure I’m smooth for you. I lock my clitty up, and put a plug in my sissy pussy. I paint my fingernails to match my already painted toes and put on a set of lingerie I got just for this occasion. I’m only going to lose my virginity once, so I have to do it right. I add in some breast forms to fill out the bra and give you something to grab onto or play with. I slip on some thigh-high stockings.

My hands are shaking as I do my makeup, lipstick and a wig to complete the look. I’ve been practicing for days to get it right. I slip into a dress and some heels, and splash some perfume on me. If everything goes to plan, you’ll be taking the dress off in a few minutes.

You come up to the room and knock. I hesitate, take a deep breath and then walk over and let you in quietly. We both know what we’re about to do. You push your body against me and leaned me back against the wall as you kiss me. I slip off the heels in anticipation as we kiss, then you push me down to my knees. As I unbuckle your pants you take off your shirt, I smile. You’re about to make me complete.

I pull down your underwear, and look up to see your cock. A real mans cock. I’ve never seen or touched a real cock before. It’s large and intimidating. I smile up at you, trying to hide my fear, and lean in to kiss the head. I reach up to grab the base of it and start stroking it. I start to suck on it, and try to work my mouth around it. I eventually get a handle on things with some practice, determination and direction from you. I work to worship it, and your balls, this is what I am made for. I remember to worship the balls when I am sucking your cock. A good girl always remembers the balls. You put your hand on my head and start to fuck my mouth more and more with your cock.

My mouth starts to get tired, and thankfully you pull me up from my knees. You take off my dress. I push you back onto the bed and climb on top. I’m continuing to hold your gifted cock in my hand and jack it off. I understand where the desire comes from now, I am basically living for this cock. After a few minutes of more cock sucking you tell me its time. I’m ready for it. I roll a condom onto your cock, add some lube, and get on my hands and knees on the bed. You grab my panties at the waist, and slide them down, revealing my plug I’ve had in the whole time. With a pop it comes out at your insistence, and leaving my empty sissy pussy waiting. You slide into position behind me and place the head of your cock at the entrance. I look back and ask you to “Please take my virginity.”

With a push, the head of your cock slides in. You pause for a moment and then start slowly inching forward. Eventually, after what seems like forever, you’re completely inside of me. I’m no longer a virgin and you’ve made me into your sissy. You pull back and start to thrust into me. You go slow at first, but then you start to pick up the pace and use my pussy. The metal of my chastity cage and lock clank together as you thrust into me. I can’t hold it in anymore and start to moan and thank you. I reach back to spread my ass cheeks as you continue to fuck me. Then I reach to rub my clitty, only to find the cage and remember that this isn’t about my pleasure, it is about yours, and that I was getting pleasure by your cock in my sissy pussy.

You push me down onto my stomach, and start pumping away faster and faster. You’re using me like I was made for you. You’re getting close. You push off of me and your cock pops out of me. You take off the condom and I turn around, you shoot your load on my face. I reach up to pick up the cum on my finger and put it in my mouth. I savor the taste. I have become a complete slut for you. You pull me up, and turn me around, I submit completely. You pick up the plug, add some lube and put it back inside of my willing sissy pussy. You pull up the panties, smack my ass and tell me to go clean up.

I get up and gingerly walk to the bathroom to clean myself up, I grab a warm washcloth and come to clean you up. After I clean you up, I go back to the bathroom to fix my makeup and reapply lipstick. As I’m fixing my makeup, I hear you order room service. A steak for you, and a salad for me. I don’t get to have any meat other than yours. I put on a new set of lingerie and a new nightie and slip under the covers of the bed. You turn on the game while we wait for room service.

Room service arrives, you collect our meals and dismiss them. As we start to eat, I think back to a few short hours ago, to all the hesitation I had, and then I remember how good it felt to submit and be yours and to have your cock inside me. I can still taste your cum as I eat. We finish and I collect the dishes and head to put them outside the door. You slap my ass as I walk by. I look back with a knowing grin.

The next morning, I awoke to see you have already left. The night already feels like a distant dream. I remember vauge pieces where we continued to fuck long into the night after we had room service. My jaw was aching. As I got out of bed and ran into the shower to clean myself off of the sticky mess we apparently made, things started to come back. My sissy pussy was raw to the touch, I had definitely been rode hard last night, but that’s what I had asked you for. A gentle start, but a hard ride to make sure I would always remember it. As I got out of the shower, I looked around for my boy clothes I had worn into the hotel. I swore I had put them on the shelf in the bathroom. I couldn’t find them. In its place was a pair of leggings, a pink bra and panties and a shirt, with a note from you. As I read the note I couldn’t help but smile:

“I’ll be in touch. Wear these home. Good girl.”

I put on my clothes, did my makeup, and walked out of the hotel a new sissy girl who had found herself.

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I’m super hot and horny right now, out of town away from all of my sissy toys and wanting to get back home. I ordered a fucking machine and a new set of plugs so I can continuing training to make this a reality, My new toys will get there in a few days, a day after I get back. Thankfully. I'm starting to accept this is who I am.