Taking the Plunge Bk. 02 Pt. 01

(Hi, dear readers, girls and Daddies! Thank you for all the kind feedback from Book 1. It's been so much fun getting to know some of you and I wish everyone a fun, sexy time on their own journey.)

*

I dressed soon after he left the hotel, leaving my cage on, and I departed the suite, but not before scouring it for anything I might be leaving behind - so many little items of clothing and sex play all over. I marveled at what a mess a Daddy and sissy can make over 24 hours on their first hotel date.

As I stepped out of the door, I looked back into the suite, just remembering everything from my first night ever as the sissy I always wanted to be, and suddenly aware of my sore, pink assho....I mean my sissy pussy....which had taken Daddy's cum inside three times. It felt, I don't know, accepting and feminine somehow.

I pulled my rolling carryon packed with all of my slut clothes, now dirty with the remnants of our pleasure, out of the elevator and into the lobby. I saw myself in a giant wall mirror there, dressed in boy clothes for the first time in a day. Wow, I don't know what's real about me anymore......don't look, trisha, don't look.

Honestly, it was painful, and my gender confusion came back with a bang, reinforced by the way I was addressed, standing there staring at some ghost of a man who seemed to be fading away before me.

"Sir, may we call you a taxi? Sir?"

Oh fuck, he's talking to me.

"Yes, thanks. I'll wait at the front."

'Sir.' If only he knew the real me. What I had been doing - and loved doing up there in the big suite.

I stepped outside and closed my eyes for just a second and took in a deep breath to calm myself. I have to remember what Daddy told me when I had my little panic attack last night:

"'I want to talk to the man inside of you, just for a moment. I just want to tell him that I know he's there, I appreciate the time that he's giving us to play, and I promise to always be good to you, Trisha. I want him to have as much of a good time as we are having, but he has to stay out of the way and let us enjoy the ride.'"

I smiled, remembering just how tender he was with me in my most insecure moment. It was just all fun, wasn't it? I mean it was so so hot and incredible, and even the sissy 'shame' that's like, part of the fetish, is just kinda all for fun when you accept that you like it, I guess. I still didn't have the answers standing there but I was calmed down by Daddy's words and the knowledge that it was just fine. I just had to figure it out for myself.

I took a cab ride back to my apartment in Brooklyn. The ride was one of those wistful 'morning-after' ones in New York, with a too-bright blue sky and all the Saturday activity of the city.

My mind was bouncing between the fun we had, and the other thing that Daddy had said: "if we meet again, it's the beginning of the end for [my male name]". I knew, from our internet chats before meeting, that he wanted a willing sissy to feminize, and I know that's what he meant. Now it's up to me to take the plunge. Oh god, I need someone to talk to!

I spent the rest of the day online reading as much as I could about feminization, the steps, what it's really like to be a female in the world, everything from accounts of just being a part-time CD to full trans SRS and the whole spectrum. It helped me greatly to realize that being a sissy is different from being trans. I don't feel 'like a woman' all the time, and didn't steal my sister's panties or anything. It seemed that, for me in particular, being a sissy is a sexual kink. Not that that's bad - it's the most intense thing I've ever done and maybe my sexuality is feminine but my 'being' in the world is male?

I didn't know. Fuck, I was confused and I just wanted to talk to Daddy some more about it, about what he wants, and what I want, and and and....

Our date was much more intense and emotional than I had expected. I needed some time to process everything. It's probably a good thing that he's going away for a week, to be honest, I thought. But I'll be damned if I'm not going to see him again, and be Daddy's eager slut for that beautiful cock and ohhhh fuck get it together, trisha.

I decided to text him in the morning, Sunday, and tell him 'yes' I couldn't wait to see him again when he gets back from Europe:

"Hi, Daddy. May your slut please see you again? Please, Daddy?"

"What's your address, princess? I'm going to send you a little gift before I leave."

"[my address]"

"Good whore. It will come Monday night so hurry home after work and text me when it arrives."

"Yes, Daddy. Thank you, Daddy." I put in a few pink and purple emoji hearts just to be extra innocent and slutty for him. I may be a confused guy, but Trisha knows exactly what she wants.

I didn't see him at work Monday, I mean the building is huge, and who knows if he was even there, but you can bet I raced home. I waited, waited, and almost jumped when I heard my buzzer go off. I sprinted back up the stairs with the rather large box that wasn't as heavy as it looked. I ran into my bedroom and locked the door - roommate wouldn't be home yet for some time. I texted Daddy.

"The delivery is here Daddy. I haven't opened the box yet, Daddy."

"Open it, you dumb bitch." My knees almost buckled in lust from his demeaning me. Why is that so hot?

"Yes, Daddy."

I didn't just open it; I tore the box open like a kid at Christmas expecting just what he asked for from Santa.

My eyes and hands could hardly believe it.

I reached in and started to pull them all out. Counting 1, 2, 3, 4, 5, 6,.....a dozen lacy pink, lavender, purple and white panties of every style, most silk, some thongs, hip huggers, boyshorts, low rise. Underneath them were two babydoll nighties, both sheer pink in different styles, one open front fly-away and the other ending just above my clitty, frilled with soft pink faux-fur. Both were absolutely totally femme and girly and so cute. Omg.

I stared down at my bed, suddenly looking way more sissy than it had ever looked. All of these beautiful soft sexy panties and the nighties...oh Daddy. Daddy! I was so enraptured that I forgot to text him back as I turned the panties over and over in my hands marveling at their softness and variety.

"DADDY! DADDY! DADDY! THANK YOU SO MUCH DADDY!" I finally responded.

"Yvw, babygirl. Before we meet again, only panties. No underwear ever. Understood?"

"Yes, Daddy, only panties only panties 24/7 Daddy."

"Every morning till we meet send a shot of you in that day's panties. Every night before bed in a nightie. I'll get texts in Europe. Two pics each day."

"Yes, Daddy I will I promise"

"Put pair on now and show me, slut."

You never saw anyone take their clothes off as fast as I did right there and then. In mere seconds I was naked, my eyes scanning the bed...which one?? What's the most submissive, girly, slutty pair? Oh, they are all.....wait that one, hot pink silk tanga with embroidered pink hearts, very thin line of black lace around the waist and leg openings and a little baby pink bow in front. That's the one.

I pulled the pair up over my ass and suddenly she was back inside me. Trisha I mean. "Oh, Daddy," I moaned in her high femme slutty voice, as I felt myself up, staring into my mirror. I took a quick couple of pics from the belly down, turning slowly and running my hand over my ass with a playful spank, and sent them to him.

"Very nice, baby. Fit ok?"

"Perfect, Daddy. Perfect, thank you Daddy."

"Every day, and every night, bitch. Don't forget."

"I won't Daddy I promise."

"Are you going to do anything else for me while I'm gone?"

Oh......he had told me to get my nipples and belly button pierced. That's a big step, isn't it girls? But...oh fuck it why not. I mean I'm going this far with him and it's so, so hot.

I texted him back nervously:

"Nipples and belly button pierced, Daddy."

"Good girl. Send pic when done. Use this place."

He texted me a link to a webpage for an upscale salon in Chelsea catering to men.

"Yes, Daddy. I can't wait, Daddy."

He was silent, and I took the time to look over the panties again, dreaming of putting each of them on, drawing them slowly up my legs, and posing for him, while my hands were gently pinching my nipples and belly button wondering what that's going to feel like.

He texted again after a few minutes.

"Trisha, PAY ATTENTION: if you ever get scared again, text me. I've looked for someone like you for a while and I think you are special. Remember, I'll never hurt you and I want us to both be happy."

My eyes filled with tears - the tears from having someone accept me finally and stripping the guilt away from my desires. How does he know? How does he know? When I look back on it, he was so smart, giving me something reassuring that I could read over and over again, and just putting it all back into perspective.

I texted him back:

"Thank you thank you, Daddy. I'll text you Daddy and I won't run away Daddy, I promise."

"I know you won't, princess."

A few hours later, before I climbed into bed in my new ultra femme pink silk babydoll nightie, I took another short video for Daddy. I was beyond horny again for him; I had never slept like this before - in a babydoll, so soft and submissive against my skin.

As I filmed myself, I whispered "Hi, Daddy. Thank you for my beautiful nightie." And even though my face was out of frame, I slapped my right cheek hard twice just because it was fucking hot, and whispered "I'm Daddy's fuckhole," and I knew it would turn us both on.

After a few minutes, he texted back:

"Look what you did, bitch."

And he sent a pic of his giant cock, rock hard, and ready to burst.

As I lie in bed staring at the walls, my hands unable to stop feeling the delicious silk covering my smooth body, feeling those pink feminine feelings course through me, I reassured myself: 'Yes, yes, I will. I won't be scared. I accept, I accept myself. Thank you, Daddy, thank you Daddy...'

It was hard to sleep that night, then it became very, very easy.

——————————————

That was Monday night. By Tuesday afternoon at work, I was a mess. Horny beyond belief, unable to concentrate, my mind caught in some electrical storm bouncing between the clit-melting feeling of my second pair of silk panties worn under my boring office chinos and thoughts of him, Daddy - everything about him coming back to me in sexual flashes:

the first taste of his cock there on my knees in the hotel,

the taste of the base of his cock holding my mouth open when he forced himself into my wet, gagging throat,

the feel of his dominant body slamming against mine as he took me from behind,

the throb of his cock as he emptied his cum inside me again and again,

the curves of his muscular frame as I massaged him on the bed,

the incredible, expert, painful flogging that sent me into a state of complete submission,

and the sting of his open palm against my face and my ass, owning me, controlling my pain and my desire.

I think this is what they used to call being "swept off your feet."

I realized that for the first time in my life, one of those sissy 'dreams' was coming true: I hadn't slept in or worn any boy underwear in 24 hours. It was all femme underneath, all the time. It had made me crazy with desire, along with sending Daddy pics and posing for him while he was away.

Tonight I wanted to do something special for him, to surprise him the way he surprised me. From our months of internet chat, I remembered Daddy's deep, wonderful denim fetish and berated myself for not paying it enough attention.

'Don't be such a fucking selfish whore, Trisha, all wrapped up in your own doubts: Daddy's pleasure is first,' I told myself, trying to bury my bubbling self-doubt in my overwhelming sissy lust for him.

To surprise him, I decided to go shopping after work for my first pair of girls' hip-huggers, extra lo-rise, the way he likes it. But what size am I in girls' jeans? Omg, I have so much to learn. I'm going to feel ridiculous at the shop, but whatever - I can't be the first guy to shop for them, and it's not for me really. I mean it is, but it's for Daddy....all for Daddy.

The shopgirl was so kind, after I robotically blurted out a sentence I had practiced over and over on the way there:

"Hi! I'm looking for a few pairs of distressed very lo-rise hiphuggers, but I have no idea what size I am. Can you help me?"

She gave me a knowing look and asked, "How tight do you want them?"

"Pretty tight," I replied without hesitation.

"Ok, turn around for me. Bend forward slightly. Good, wait here."

She brought me four pairs, two different styles in two sizes each and took me to the dressing room.

As I pushed my leg into the first pair I thought 'these are way too tight, I'll never fit' but to my shock the jeans just sort of hugged my body, making room for me and accenting my calves and thighs, and...oh wow, they are perfect over my already rather femme ass that never really fit in men's jeans. And they close so sexily at the front, sitting so low under my belly button. Holy.....

At that moment, seriously from that moment, I've never wanted to wear men's pants again.

I stared at myself turning back and forth in the mirror, marveling at the leg and butt-enhancing properties of the jeans but more so at how they made me feel. These are Trisha's jeans; they are made for her, for me. They make it real in a different way than the slutty, playtime clothes that I had brought to the hotel.

This was something more frightening to me: 'everyday' clothes, which felt like a new level of self-acceptance. But they are so sexy - and I was so horny for Daddy. But if I get these, I'm taking another step deeper.

What am I doing? Who am I really? Is this me? Oh god, don't freak out, I told myself as I started hyperventilating slightly. My hand moved involuntarily to my cellphone, wanting to text Daddy and yell "Help me! help me come back to you Daddy".....not here, trisha, not here! Breathe!

"How do they fit?" I heard the shopgirl call out.

Thank the stars for the kind people of the world. I was immediately brought back to reality and my breathing slowed and I popped open the door to the changing room and stepped out with a little smile, not saying a word.

"Wow!" She exclaimed, stepping right up behind me. "You have a great butt, and they look amazing on you!"

"I bet you say that to all the....all the....um.....really confused guys," I joked, and we both laughed, breaking the tension.

"No, seriously, You have a great shape already, and they really work on you" she told me, but she didn't have to. My mind was made up.

I bought the two smaller sized pairs. But just before I left the shop, I saw another item in my fantasy list: it was the rack of girly belts. Oh wow, so many from black rock-n-roll style with metal studs to the cutest pink faux leather with rhinestone hearts all around. I went back to the counter with that one, and the shop girl gave me a sly, 'in on it' grin and she whispered, "Have fun."

My heart was pounding all the way back to my apartment, eager to strip off these horrible male office clothes and dress for Daddy, wanting put on a real show for him, now on his trip overseas and might have just landed.

I had a few hours until my roomie would be home, so I dressed quickly: today's panties were baby pink lace-back open crotch boy shorts. I peeled on the first pair of distressed hip huggers, so tight that they look almost painted on. Oh wow, they feel just as good as in the shop, so tight on my body, holding everything in place for Daddy.

I realized right there just how much female clothing is inherently submissive, or at least turns the power dynamic on it's head by manipulating male desire. The heels that could barely be walked in, and the tight jeans and skirts that restrict movement while inviting the male gaze and desires. I'm going there with you, Daddy, and for both of us.

Then, I put on my 5 inch clear platform stripper heels, and the new pink belt. The outline of the pink boy short panties was just visible under the hip-huggers. Omg. Seriously, if you just saw a pic of me from the waist down with all this on, I was all girl. I could hardly believe it, and it turned me on so much knowing he was was going to love it.

From my sissy stash, I pulled out the white bra and 'slut' crop top from our night together at the hotel, and my long very-sandy blonde wig, fastening two cute little pigtails at the top, with all-pink hair ties to match the belt. They dangled over my face innocently.

I couldn't do full makeup as I didn't want to get busted later by my roomie (looking back now, it was silly to even care about that) but I did carefully apply mascara and the same bright red lipstick that Daddy loved messing up so much last week.

And there I\she was again - Trisha - standing seductively before the mirror looking at myself and my new denim-enhanced curves. In just a few minutes, I had transformed from a boring office boy into Daddy's eager cumslut again. I need this more than anything; this is me and Daddy wants me, he wants the real me, the kinky me, the free me.

There's just one more thing I need for my photo/video shoot for Daddy. I walked around the side of the bed and picked up my blah male chinos from the office, and slipped out the 2 inch black leather belt from the loops. Now I can begin.

I positioned the camera on the dresser and set the photo app to take a pic every 10 seconds, and I started posing in my jeans. Everything from ass closeups to full body, draping the belt over me, then presenting it to the camera as if I was asking Daddy to use it on me, then pushing my tongue out for a dramatic licking of it, and on an on. After about 45 minutes of posing and editing it down to the best 7 pics, I texted him:

"Hi, Daddy. I hope an extra text is ok, Daddy. I couldn't help it, I went shopping for something to show you, just for you Daddy. " I added a few cute emoji hearts, and I sent him the gallery, nervously hitting send.

What do I do now, just wait? I decided to stay dressed as long as possible, it felt so perfect. I thought I would get maybe an hour in these clothes just prancing back and forth before my mirror, practicing sitting and standing like a sissy girl, talking to myself in my ultra high femme voice, enjoying the tight constricting denim accenting my curves. I even closed my eyes in a haze of lust and sucked my thumb for a few minutes repeating "Daddy Daddy Daddy Daddy" over and over again in my mind, even though I'm not into age play, but it was so hot to just be Daddy's little girl slut waiting for him to reply.

If he replies. He's probably asleep or in a dinner meeting or fucking some other slut and forgetting about.....

My phone gave a strange ring that I had never heard before. I raced back to the bed and picked it up. My eyes widened as I saw it "DDY requests FaceTime. Accept?"

I gulped. I really did it this time, Trisha. I took a quick breath to steady my nerves as I put my earbuds in. Yes, I accept - I accept FaceTime and I accept what Daddy wants and I accept myself.

I accept.

"Hi, Daddy."

"Well, well, well princess. Quite a surprise."

He was smiling slightly, apparently naked except for a large peach colored hotel bathrobe. My heart jumped hoping that I had pleased him.

I was holding the phone with one hand giving him a view of my body from the lips down, moving it slowly around to show him my curves, the heels, everything.

"Did you buy those jeans today, babygirl?"

"Yes, Daddy, I bought two pairs of them and I couldn't wait to show you, I wanted to surprise you Daddy."

"You certainly did. Are you alone?"

"Yes, Daddy for about an hour I think, then my roommate should be home, Daddy."