A Secret Admirer Pt. 01

I had always been the classic introvert. I had struggled with social interactions for my entire life. I was perfectly happy spending my evenings gaming, instead of heading out to the bars. On the off chance I did agree to go out and hangout with friends, I found it exhausting.

So while many people struggled with the isolation of quarantine, I was perfectly fine. Fortunately I had the ability to work from home, so I didn't have to go out for things other than the essentials. It also allowed me to indulge into both of my guilty pleasures, gaming, and crossdressing.

I had been dressing since my teenage years off and on. But in the years after college, my dressing had become much more frequent. I loved coming home after a long day's work, stripping out of my clothes, pouring a glass of wine and running a hot bath. Soaking and shaving my body, before sitting down and applying my make-up. Then picking out some sexy lingerie or outfit for the evening. All tarted up, I would sit down at the console for a long night of online gaming. I had even created a gaming profile for my crossdressing persona, where I would occasionally stream in dress and my followers would send me money. Sometimes, this would devolve into me just playing with my cock or fingering myself on cam. But it provided me with a nice supplemental income that helped fund my girly habits.

After a couple of weeks of isolation, not much had really changed with my life. Life at home pretty much allowed me to live as a girl full-time. Other than the regular video conference for work each week, I was in dress 24/7. I had even ordered takeout one night, and answered the door in a slutty little school girl outfit. I gave the delivery boy an eye full when I bent over in front of him.

I had come to enjoy my life as a girl quite a bit, even to the point that I was slightly dreading going back to real life.

Soon the weather began to improve, and regulations around the city began to lift a bit. This allowed me to get some much needed exercise. After a run one morning, our doorman had stopped me to tell me that I had received a package. I found this strange, since I couldn't remember ordering anything as of late.

The box was addressed to the occupant of Westwind tower apartment 1420. That was indeed my apartment, however there were no other discernible markings on the box. There wasn't even a return address. Not thinking anymore, I gathered up the box before heading up to my apartment.

I sat it on the table before heading for the shower. I needed to shave, as I was planning on dressing up and streaming later tonight. The whole time I was touching up my legs, ass and cock, my mind took me back to the strange package.

I quickly finished showering before getting out and ready rather quickly. I grabbed the box, and sat down on the couch to quell my curiosity.

I quickly opened the box and peeked inside. The box was neatly packed with three other packages, and an envelope on top. The envelope had a simple message written on it, "From a Secret Admirer."

A secret admirer? Who could it be, I wondered to myself.

Inside the envelope was another surprise. The letter was filled with money, $2000 in total. Now I was really confused. This had to be a mistake. There was no way this was meant for me. I dug further into the contents to try to discover something about the sender or who this box was intended for.

I then opened one of the other gifts to find a lingerie set. White lace panties, pushup bra, and stockings. They were very pretty, and very high quality. Much better than the few bargain store pieces that I owned. I sat those aside and returned to the box.

The next package contained a small pink vibrator with a bulbous head and a small bottle of lubricant. Now things were getting strange.

Last was a small little box. I opened it to reveal a cellphone. No explanation, just a cellphone.

Now I was completely confused. What the hell was going on?

I sat the phone aside for the moment and surveyed the haul. The lingerie wasn't all that unusual. Guys were all the time sending me lingerie when I gave them the link to my naughty, secret Amazon wish list. But the money. No one had ever sent me money. This had to be some mistake, I thought to myself. I searched the packages frantically for some source of information about either the sender or the destination. Try as I might, I found nothing.

Then I thought about the cellphone, maybe it contained some intel about the origin of these things, or who they were intended for.

I quickly booted up the cellphone. Once booted up, I noticed there were only two programs. A contacts app, and a camera app. I opened the contacts app to find one solitary name "Daddy."

I pressed the name, and began typing out the message: I received this package by mistake, I was hoping to either return it to you or the person it was intended for.

I sat the phone down and began packing the various things back into the box as I awaited a response.

About a minute later I heard the phone buzz on the coffee table. I quickly grabbed the device and opened the message.

"Oh, no my dear. Everything is for you" it read.

For me, I thought to myself. Who the hell is this person, how do they know who I am and know my crossdressing secret? Then my mind began to churn, and not in a good way. Did this person mean to do me harm? But if they intended to out me or embarrass me, then why the gifts and why the money.

After considering my reply I wrote back, " thank you very much but to be honest I'm a little confused?"

"I was afraid you might be but I thought the suspense might be hot," the return message read. Swiftly a second text came in, "know that I mean you no harm. Consider me a Secret Admirer of yours. I've observed your journey from afar. I meant for the things to be a token of my gratitude to you."

A secret admirer, I never shared my address with guys online that I streamed with. And this package hadn't come from the carrier. I wrote back quickly, "have you been spying on me?"

"Let's not call it spying, how about that you caught my eye and I've become a fan," they replied.

I had a peeping Tom it seemed. But instead of being creeped out I felt a tingle of sexual excitement. It catered to my kink of exhibitionism.

I finally returned a message, "well I guess that's OK and I really appreciate the gifts, but the money is too much. I would like for you to have it back."

"I'm glad you liked the things but the money I insist you keep. Do with it what you wish, buy yourself something nice, payoff bills, donate it to charity if you wish. Consider it a down payment of sorts."

"Down payment?" I replied.

"Well I have a bit of a proposal for you my dear, if you would be willing to consider it?" The next message read.

Down payment? Proposal? Whoever this was had my attention. My curiosity got the best of me and I replied, "tell me more."

It took several minutes before the phone began to vibrate again. I opened the app to see I had received several rather lengthy messages.

"First know that my intention is not to out you or humiliate you, unless you're into that. Consider me a wealthy benefactor, in need of an outlet for his attention and money. I helped train another girl like you a few years ago and thought we might come to a similar arrangement. I see you have a lot of potential and wish to help you reach it."

He then continued," Second, if you do decide to continue our arrangement, know that if at any time you wish to walk away you have the freedom to do so. Any gifts that I may give you are yours to do with as you wish. I will never try to use any conversation or material shared between us to defame, blackmail, entrap you. I will never ask you for any identifying information, or your real name or number. If at any time I am out of line just tell me, I can be demanding yet I do know the meaning of no. I will always respect your privacy, and I also hope you will respect mine as well."

In the next message he explained our "relationship" further. "Now onto the fun parts. If you agree so far, I will send you daily tasks for you to complete. Tasks can be simple things like take a picture of yourself in some sexy lingerie or maybe more ambitious tasks. You can choose to complete or not complete tasks that you don't feel comfortable with. Upon completion of any tasks you will receive a gift the next week. That gift may be something small or something larger depending on how many tasks are completed and how pleased I am with you. As stated before, you can walk away from our relationship at any point with no ill will."

I read and then re-read every word,while I contemplated the offer from my secret admirer. While a little out of my normal sexual comfort zone, I had to admit I was intrigued. I had been feeling that over the past couple weeks that something was missing from my dress up sessions. While I still got off on all the horny comments from other guys and girls during my streaming sessions; I needed more. Maybe this was the universe speaking to me. Maybe I was ready for the next step.

So I decided to jump, "I think I'm in," I replied.

He messaged back,"I was hoping you would. So task #1: take a few pictures in the pretty little lingerie set I bought you. If you're feeling extra naughty maybe a couple with the toy.``

"Got it!" I added.

"Good girl," he responded.

It was later on in the afternoon by this time. I decided to try and do some work. However my mind kept drifting off to my new arrangement. My dick stiffened in my pants thinking about the idea of being directed to do things. I had never considered myself to be submissive but it was quite titillating relinquishing control to another person. Another man, no less.

After about an hour, I finally gave up and went to get ready. I grabbed the gifts off the coffee table and went to my room to get ready.

I quickly stripped out of my boy clothes and threw them into the hamper. I then sat out each piece of lingerie onto my bed. The bra and panties were white lace with little crystal studded about the lace. The panties were open backed, with two thin white straps that looped up to the waist band. The stockings were sheer white with lace tops.

The panties were the first to go on. The small lace patch at the front did little to cover my stiff cock. It just smashed it up against my body. The straps nestled neatly underneath my butt cheeks leaving my entire derriere exposed. My guess that was part of his plan

Next came the bra, which thankfully fit perfectly. That is except for the empty cups that jutted out away from my flat chest. Quite the pair of boobs could be squeezed into those empty cavities, I thought to myself. Maybe I could use some of that money to buy a set of fake breasts. I had always wanted a pair but never could justify the money for a nice set.

Then came my favorite part. The stockings! I had grown to adore the feeling of stockings on my shaved legs. I sat down on the bed and carefully pulled the first up my leg, savoring the feeling of the fabric gliding across my smooth skin.

After I was dressed, I sat down to apply simple make-up. Just the basics, but I decided to go for some bright red lipstick. I teased my shoulder length, brown hair into a more feminine style quickly as well. For the finishing touch I got my bright red pumps from my closet and stepped into them.

I stepped in front of my full length mirror to observe my work. I had to admit it wasn't my finest work, but I still looked hot. The white lingerie made me look like a bride on her wedding night. Maybe that was my admirers' intention.

I got set up and started snapping photos. I tried to take several in different poses. I left little to the imagination, making sure to get a few of my bare hole for him.

After I finished getting the shots I wanted I sat down to look through them and select the best ones to send. That's when I remembered," If you're feeling extra naughty maybe a couple with the toy."

"Why not,?" I thought to myself.

I retrieved the vibrator and lube from my dresser and began examining it. It was bright pink and velvety smooth. It wasn't terribly large, probably only 5 inches in length and the shaft was roughly an inch in diameter. The head somewhat resembled a cock head, slightly bulbous in nature, but veered up slightly. The base was flared and contained three buttons. The first caused the whole thing to vibrate. The second button caused the shaft to move back and forth in a pulsating motion. The final button caused the head to flex back and forth in a waving motion.

I put on some porn to help set the mood. I quickly found a video of a cute crossdresser sucking a cock.

I wasn't completely new to anal play, but wasn't all that experienced either. I began carefully lubing up the toy before turning my attention to my own hole. I added a rather big dollop of lube to my entrance, then laid on my back and spread my legs. I grabbed the silicone toy and positioned the head at my hole. I snapped a couple quick pics, before I started to push. I pushed and pushed trying to insert the toy into myself but it wouldn't budge. I decided to try a different plan of attack.

I rolled to my side and sat the toy beside me. I then took my fingers and slowly started working my index finger inside of me. My wet digit slid past my opening and I used it to spread the lube around my entrance. Once I was a bit loosened up, I added the second finger. I massaged my hole with my fingers, slowly working myself open in preparation for the vibrator.

After a couple of minutes, I felt like trying again. I grabbed the toy and relubed it. I decided to stay on my side but just lifted my right leg into the air. This time my sphincter relented and the head popped into my opening. The toy slid the rest of the way in on its own. It scared me for a second thinking it had disappeared inside of me but the flared base kept it from getting lost. I grabbed the base and worked it in and out so I could take a few more pics with it. Each time I let go of the base it slid right back into place. It was quite the sensation of being full. It was strange, but quite pleasant.

I hit the first button on the base and the vibrator buzzed to life inside of me. I hit the button again and they got even more intense. I cycled through the modes finding the one I liked the best. Before laying back and enjoying the ride.

It was kind of nice that the toy was hands free. I had to do little but lay back and enjoy the pink vibrator pulsating inside of me. As I lay there, some deep inside of me began to feel good. And slowly the pleasure began to build. I noticed that if I moved my hips I could adjust the toy. As I rolled my hips, there was a spot where I felt intense pleasure, unlike I had ever experienced. I sat up, putting pressure on the toy, trying to further locate the pleasure point inside of me. I even started bouncing up and down, imitating the motion of a woman riding a cock. But the best I could do was occasionally bump into the spot occasionally.

Frustrated, I hit the second button. I instantly began to moan as the shaft began to pulsate. The pleasure was now higher, with little bits of euphoria as the convulsions hit my spot. I kept rolling my hips looking for release. I now felt like I was about to burst. I was writhing on my bed trying to find a way to push myself over the edge.

My hand found its way in between my legs and hit the third button. The waving function did the trick. Each time it hit that pleasure spot inside of me. I started moaning louder, shouting obscenities as the pleasure within my body began building once more.

Eventually the dam burst and my body began to orgasm. Copious amounts of cum shot from my cock. Spurt after spurt, not ceasing. My entire body convulsed and tingled as a wave of euphoria washed over me. I nearly passed out.

As I layed there trying to regain my composure, I thought to myself, " I don't care if I ever orgasm the regular way again!"

I eventually got myself up, and cleaned up the mess I had made. I changed into some dry clothes and put my lingerie in the wash.

Then my attention turned to completing my task. I sent the pictures that I had taken, to my admirer, and patiently waited for a reply.

Several minutes later I felt the phone buzz, "Oh my, you look like a little sissy princess. So heavenly."

He continued further, "I also see you had a little naughty time with the little friend I sent you too. Did you enjoy it?"

"I had an orgasm, hands free!" I replied.

"Wow, did you like that," he questioned.

"I've never had one before, it was amazing. I lost all control, it was the most powerful thing I've ever experienced," I explained.

"That is indeed exciting, it usually takes quite a bit longer for most girls to achieve orgasm. You must have a sensitive p-spot," he replied

I had never heard that term p-spot before but I felt like that must have been the point inside of me that gave me so much pleasure.

We chatted a little more back and forth before it was time to go to bed.

"It had just occurred to me that I have never asked you for your girly name," he replied.

"Well I've never had one," I replied,"but I've always liked Rachel."

"Rachel it is then, it kind of fits you," he added.

"What about you, how would you like me to refer to you?" I asked.

"You can call me Daddy, or Mr. P," he replied.

Thank you for reading A Secret Admirer Part 1. Stay tuned for Part 2 cuming soon!!!