A Secret Admirer Pt. 02

The next week went by like a flash.  Mr. P kept sending me daily tasks that I eagerly completed. 

We were nearing the one week anniversary of our arrangement, and I was looking forward to my next gift from Daddy.  I found myself daydreaming about what it could be. Maybe some new lingerie, or a couple sexy outfits, possibly a new toy or two.  

I had just completed my task for the day, a voice training lesson he had sent me, and sent him the audio. A few minutes later I received a text from him.

"Thank you for completing your task, I have sent you a small gift early.  You will need it for your task tomorrow."

As I finished reading it, a sharp knock at the door startled me and caused me to jump.  

I wasn't expecting any visitors or deliveries today so I wondered who it could be. But when I looked through the peephole, there wasn't anyone there.  I slowly opened the door, peeking around the door to reveal a relatively large pink package with a large white bow.  I looked down the hallway but there was no one there.  On the package was a note, "To Rachel, From Daddy."

Slightly embarrassed, I gathered up the package and quickly brought it inside.

I untied the bow and sat it aside. Then I began to unwrap the pretty pink paper.  Once unwrapped, I opened the box to reveal the contents. 

The box contained girly workout gear.  A pair of pink running shoes, a pair of pink yoga pants, a black padded sports bra and a pink top. There were 3 workout videos also: The bootylicious workout; sexy yoga; and the beginners lap dancing workout. In the bottom of the package was a letter.

The letter was from Mr. P and said the following," Daddy requires that you stay in tip top physical shape. Your task for tomorrow is to go for a run wearing the following attire. I'm well aware that this might be your first time out in public dressed, but I feel you are ready for this push. Make sure you snap a couple pics of your cute ass on your run! When you return you will complete one of the following workouts and video it.  From this point forward you will complete a workout a day as part of your training. "

What the hell, I thought to myself. He expects me to go out like this? 

I had no trepidations about completing tasks this past week.  But this is the first time I was seriously considering not following through.  It was true that I enjoyed the thrill of dressing in women's clothes but that was in the safety of my own home.  Even during my cam sessions, I was in front of complete strangers.  Going out in public here was a different story.  What if I bumped into someone I knew? 

Well in reality, I didn't know that many people.  

But what if someone from work ran into and recognized me? 

Well almost everyone I worked with didn't actually live in the city. Those that did, lived in other parts of the city. The chances of bumping into someone would be slim to none. 

But...but..., to be honest I was losing the argument with my own logic. Masks were still required outside. No one had really ever seen me with long hair. Add in a little makeup and even in the off chance I did bump into someone on my run, it would be extremely unlikely I would be recognized. 

So I formulated a plan, I would get up and out early.  I could use the back door to the building, to avoid the doorman, and I could pick my path through the park so that I could avoid most other people.

It was getting later in the evening at this point, so I finished the rest of my day and then began getting ready for bed. I knew I was going to have an early morning!

I awoke to the sound of my alarm. It wasn't even light outside yet, which was unusual for me. But I wanted to get going as soon as it was light out so that I could lessen the chance of being caught. 

I got up quickly and proceeded to get dressed. I threw on the leggings and sports bra first. Stuffing the cups with stockings to give me a little more volume up front. I tossed on the pink top and then stepped into the bathroom to finish getting ready. 

I applied very subtle makeup before quickly brushing out my hair and throwing it into a ponytail.  I grabbed a mask and put it on.  I took a step back to look at my reflection to see if I could pass. I indeed looked like a girl, except for one thing.. my bulge!

The tight fitting leggings did little to hide my "package."  Everyone is going to notice that. No this wouldn't do at all. 

I ran into the kitchen and quickly found some tape. I hadn't tucked since I had done some cosplay pictures about a year ago, but I hoped I could make it work. I pulled down my leggings and did a quick tuck job, before pulling them back up. I returned to the mirror to double check. 

The results were good enough. I wasn't flat, but there wasn't a pronounced bulge either.

By this time, it was already light outside. I quickly threw on my shoes, grabbed my head phones and quickly snuck out into the hallway. The back stairwell was my idea. It was the 14th floor, so not many people took the stairs.  Plus the stairwell opened up next to the rear door of the building.  

I flew down the stairs, and once at the bottom I tentatively peeked into the hallway. Once I was sure the coast was clear, I bolted out the door. 

Once outside I felt much better. Maybe it was running, which was slightly uncomfortable being tucked, or maybe it was the soothing voice of Katy Perry. But either way, I was much less on edge. There were only a few people out, and no one was stopping and pointing at me. I even got a little wave from a cute girl who was also out running. So far my first adventure outside en femme had gone flawlessly. So far.

I ran to the midpoint of my loop, and as I was in a place where there were no other people.  I quickly took out my phone and snapped a couple of photos for Daddy.  With my visual evidence taken care of, I made for home. 

The rest of my run was uneventful, and before long my building was in sight. Even to my surprise, the little old ladies weren't out walking their dogs next to the back door.  I quickly made my way up to the back door, and that's when terror set in.

"Oh shit, please tell me I didn't forget my pass," I mumbled to myself.

In my haste to get going this morning I had left the electronic pass that allowed entry to the buildings rear and side doors. I stood dumbfounded, trying to formulate some sort of plan. My first thought was to just wait for the next person to come out of the building and sneak in that way. But literally the only people that came in this way were building staff and the little old lady's walking their dogs.  I looked down at my phone and it was already 8:00. The staff would already be there, and the lady's would have already walked their dogs.  

The next idea was to try the side doors, but that was equally unlikely to work.  Really I had only one path forward, the front door.  That meant possible interaction with other people who knew who I was.  

I tried to calm myself down. I told myself maybe it wasn't that busy, I thought I was pretty passable, maybe no one would think twice.  I could tell the doorman I was Mr Jake's new girlfriend, yeah that might work. Maybe there would be an elevator waiting and I wouldn't have to linger down in the lobby.

I peaked around the corner, and to my delight the front doors were propped open this morning.  Trying to encourage myself I said, "see, things are going to be ok."

The coast looked clear so I took off for the entrance.  I entered the building at a good pace. The doorman tried to stop me to identify who I was, but I just quickly blurted out, "Mr. Jake's new girlfriend, forgot pass."

The sissy gods must have been smiling on me because as I entered the lobby at a trot, there was an open elevator waiting. I darted into the lift and quickly hit the button.

The doors closed, and I could finally breathe.  I had done it. I had gone out in public dressed. It was a thrilling experience, even though it was quite terrifying.  

The elevator reached my floor and opened out to my hallway.  I turned the corner to my apartment to see Alexa.

Alexa was my neighbor. She was also possibly the hottest woman I had ever seen.  If you looked up bombshell in the dictionary there would be a picture of Alexa.  Think fitness Barbie. She was tall, tanned and tight, with long, platinum blonde hair.  She sported a breathtaking, obviously fake but breathtaking nonetheless, set of tits and an ass carved by the gods.  I'm a little ashamed to admit that I had masturbated to her Instagram on more than one occasion.

Alexa was also terrifying. The few times we had interacted, she carried herself with this smooth confidence and oozed an aura of ball shriveling dominance.  I found myself cowering in her wake, every time we talked.

Luckily she hadn't noticed me yet.  I quietly made my way to my door, trying to avoid any interaction with Alexa. 

"Cute shoes girl," she shouted at me.

Startled, I dropped my keys. I turned to look at Alexa as I picked them up.  We locked eyes. Those piercing blue eyes saw through my girly facade.  I quickly grabbed my keys and opened my door, quickly shutting it behind me.  

My heart was beating about a thousand miles an hour. "Note to self," I stammered, "avoid Alexa."

The rest of the morning went smoothly. I completed the bootylicious workout video, which was hard as hell, and sent my proof to Mr. P.

I completed my work for the week early, so I was done with everything by early afternoon.  I was looking forward to an early weekend, when the phone buzzed.

"Daddy is pleased with your progress, your gifts will be arriving soon. Your task for tonight is to pick your favorite new outfit, and set up a cam session with me. I will give you further instructions then. Love Daddy."

I was giddy with excitement about the possibilities so I texted back, " Can't wait! Love you too Daddy XOXO."

About an hour later, I received a call from the front desk that I had a delivery that I needed to pick up. I threw on some boy clothes and went down to retrieve it.

The doorman was waiting on me when I got there. I blushed a little, remembering our run in this morning.

"Nice to meet your girlfriend this morning," he said.

I replied," yeah I forgot to tell the front desk she would be staying with me occasionally."

"Well you're a lucky guy, she's a cutie," he added and gave me a little wink.

I must have turned the brightest shade of red ever.  I quickly grabbed the rather large box and waddled my way back to the elevator.

"Tell her I'm looking forward to seeing her in the morning, and to not be a stranger!" He shouted as the doors closed.

I managed to get the package safe and sound back inside my place.  It was almost double the size as the first box he had sent me, and twice as heavy.  

I opened it up, like a kid opening gifts on Christmas.  Inside there were many different items. Skirts, blouses, and even a dress! My first dress. I was positively elated.  Along with some clothes there were a couple bra and panty sets, a cute turquoise baby doll and a couple new pairs of stockings. Then I saw it, a bright red corset! 

I had always wanted a corset, they always looked so sexy.  This one was bright red with black piping. It had 6 attached garters and matching stockings. Strangely there were no panties but I had made pairs that should match. 

There was another white box, and the envelope at the bottom.  The envelope had,"To Rachel, a little extra for being such a good sissy," scrawled on it.  

I opened the envelope to reveal it contained $4,000. Holy hell, that's nearly a month's salary for me. Mr P had to be loaded to be shelling out that kind of money. 

Last I opened the white box. Inside was a larger bottle of lube and a large silicone dildo. The dildo was about 7inches long, and about 2 inches thick. I had trouble wrapping my fingers around the shaft. At the base were a nice set of big balls and a suction cup.  The whole thing was ultra realistic, and a cinnamon brown color. I was going to need a lot of lube to fit this thing inside of me, graciously Daddy had supplied it!

I cleaned everything up, putting the clothing and lingerie away.  I ordered some food and had an early dinner so I would have time to get ready for my video date with Daddy.  

Time quickly approached for me to get ready. Then I took a quick bath and touched up shaving so that I was smooth. Next I worked on my hair and makeup. It still wasn't great but I had gotten a little better.  

Next it was time to get dressed. I knew as soon as I picked it out of the package that I would be wearing the corset, but the bewildering maze of clasps and strings left me stumped on how to put this on. I quickly searched how to put on a corset by yourself. I found an instructional video on how to wear one. With the video's help I was able to get the thing on. I wasn't able to get it tight enough to achieve the hourglass shape I coveted but it still looked good on me. I loved how it squeezed my body into a vaguely more feminine shape. Except for the bust that is.

I stared down at the empty cavity and sighed, " I wish I had boobs."

I stuffed the empty space with stockings again and returned to getting dressed. I pulled up the matching red stockings and attached the tops to the corset via the garter straps. I then located an appropriate color pair of panties.  Last I grabbed my red pumps and slipped my feet into them. 

I heard my laptop ding, in recognition that I had company. 

I grabbed my sex toys and lubricant and hopped on the bed to say hi to daddy.

I started my cam, and typed out, "hi daddy, I hope you like your purchase!"

Seconds later he replied,"You look delicious baby, but I think we can lose the panties."

"Oh OK," I responded before sliding them off and throwing them onto the bedroom floor. 

"You have such a pretty little sissy clitty," he typed, "did you like your dildo?"

"Oh yes Daddy, it's so realistic. I just don't know how I'm going to fit it inside of me?" I replied.

"Oh it will fit, we just need to get you warmed up," he texted. "Wanna know a secret?"

"What secret," I asked.

"That dildo you are holding is molded after Daddies cock," he replied.

A surge of sexual excitement shot through my body and caused my cock to stiffen.  "Really, that's sooo hot!"

"I'm glad you think so, should we get started?" He questioned.

I first lubed up my vibrator and inserted it into my hole.  The vibrations caused my cock to get rock hard and begin to leak. With the pink vibe securely in place, Daddy instructed me to begin worshiping the model of his cock.  

I softly kissed the tip of the dildo, then began to slowly lick the length of it as Daddy instructed.  After giving the molded dildo a tongue path, I pushed the tip of Daddies dick into my mouth. The girth filled my mouth.  The sensation of the rubber phallus in my mouth and the silicone vibrator in my ass, caused me to moan.  I continued to suck the fake cock, taking a little more of the cock in.  I managed to get about halfway down the shaft. Daddy seemed impressed, for my first time.  

He then instructed me it was time for us to try something new.  He had me get up and take things into the bathroom.  I stuck the dildo to the edge of the tub so that it would stand erect. I then situated the laptop so that Daddy had a front row seat.  

Then it was time to prepare the dildo. It was still slick from blowjob practice but I decided to err on the side of caution, and apply a generous amount of lube.  I tugged the vibrator loose from my rear and massaged even more lube into my hole.

It was now the moment of truth.  I positioned myself over the dildo and grabbed the shaft of the dildo.  I slowly lowered my body downwards until I felt the tip of the cock kiss my rosebud.  The cool lube caused my body to recoil, but I continued my descent.  

With the head of the dildo firmly resting against my entrance, I began to push slowly at first then harder.  I gained a little depth, as the pressure against my anus continued to build.  I felt like my body was slowly opening to allow access, but try as I might, I couldn't get the dildo to pop home.

I regrouped and re-lubed and tried again. But try as I might, no progress was made. I was now a little frustrated and asked Daddy for assistance.

He told me he thought I was almost there and to try again but this time when I felt like I wasn't making progress, to push with my sphincter muscles in a manner similar to using the bathroom.  

With Daddies advice in tow, I remounted the rubber cock.  This time I had hit the same wall as before, but this time I pushed just like Daddy instructed. Now the pressure built further, and I felt my anus begin to stretch open. I inched down slowly, forcing my body down and my hole open.  

That's when it happened. Without warning, my sphincter gave way to the pressure and the dildo broke free.  I winced in pain, as my anus spasmed trying to remove the invading rubber cock.

I held myself steady, yelping in pain, not moving a muscle to let my body begin to grow accustomed to the size of Daddies love stick. 

Eventually my pain subsided and I began to lower myself onto the dong.  I slid down the shaft until I was completely stuffed. The feeling of the plastic balls nestled between my cheeks was a wonderful feeling.  I gave myself a moment to catch my breath and for my body to grow accustomed to be full of a rubber cock.  

I braced myself on my heels and the tub, before beginning to move my hips up and down. Slowly withdrawing the cock from my ass, then reinserting it.  I did this a couple of times before I found a rhythm. As I bucked my ass up and down, the uncomfortable feeling began to fade, while the pleasure began to rise.  Due to the girthy nature of the dildo, it rubbed up against my p-spot just so.  

Before I knew any better, I was bouncing my ass up and down at a steady pace. I began to moan as the rubber dick stimulated my prostate. I began to lose myself in the act, and I had totally forgotten about the camera show I was putting on.

I was now really working the cock, riding it into submission.  The sound of my ass cheeks slamming against porcelain as I impaled myself, was met by my growing cries of passion. 

"Oh Daddy, fuck me, fuck me Daddy," I moaned over and over.

I found that as I withdrew the dick and slammed back down on it, that the bulbous head would hit my p-spot before plunging deep inside me.  The sensation caused my cock to spurt pre-cum.  

As my orgasm approached, I rode the dildo harder. My moans became screams as I eventually pushed myself over the edge. Cum shot forth from my cock onto the bathroom floor. My legs went weak, causing me to lose balance on my heels. This jammed the dildo deep inside me. My pummeled anus convulsed around the cock as cum leaked from my cock.  

Once I had caught my breath, I pushed myself up. The dildo fell from my body making a thud on the bathroom floor. I could feel cool air invading the inside of my body, through my gaped asshole.  I spun around so Daddy could see the conclusion of my work.

"That's a beautifully fucked sissy pussy," he wrote. "You put on quite a show."

"Thank you Daddy," was the only response I could muster in my post orgasmic stupor.  

I got myself and my mess cleaned up, got dressed up in my new baby doll, and settled into bed.  As I lay there drifting off to sleep, today almost seemed like a dream. The soreness of my violated pussy was the only indication that it was anything but.