Sissy Dream Come True

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans.

Today I wore my red lace panties under a pair of black break-away running pants with white stripes down the side. Along with a plain black tee shirt that fit tight against my slender figure. A simple outfit that wouldn't draw any attention at work but still let me feel sexy underneath. Today should be an easy day anyway. I just have to go inspect a machine and let my company know if it's worth buying. If it is, I close the deal and go home to start my fun.

As I reached the top of the four mile dirt road of a driveway to get to the seller's house, I pulled up to the big vibratory compaction roller I was supposed to inspect. I got out of my car and was immediately greeted by an outstretched arm ready for a handshake.

But on the end of this arm was a giant, strong, mature hand with fingers the size of sausages and a palm so large my dainty hand nearly disappeared as it closed around me. It immediately reminded me of a time two years ago when I invited a silver daddy I met on Craigslist to my hotel room for a night of fun. He had the same large hands. After I sucked him off while he stood in the window of my 20th floor room he showed me how powerful those hands were when, on my request, he slowly and gently worked those mighty fingers and eventually the entire hand into my achingly hungry sissy hole. I remember howling in lust-filled delight, and begging him not to stop. It was the most amazing feeling I ever felt and we enjoyed each other all night, but as morning came he left and I never saw him again.

I snapped out of my flashback and looked up to see his face, but I couldn't recall if that was really him or not. And I'm here to do a job, so I better stay focused. We introduced ourselves and he walked me over to the machine he was looking to sell. I climbed up into the seat and fired it up. All seemed to work fine. It was a large roller like you see paving roads. I drove it back and forth a bit before turning on the vibrator function. Then the entire machine shook wildly. It was jarring at first but as I continued to test drive it I found a thrilling sensation as the large machine shook me hard and vibrated my ass cheeks. I stopped the machine and climbed down. As I did I noticed I had a fully erect sissy-clit attempting to poke out of the front of my pants.

The gentleman shot me a concerned glance and I instinctively replied, "I'm sorry daddy." But he said nothing in return. Instead he merely turned around and beaconed me to follow him inside to his home office. My face was bright red as I followed him inside. I can't believe I said that at work!

Once inside we agreed on the sale price and I arranged for transport to come pick up the machine. We finalized the deal and shook one last time.

Again I was captivated by his manly hands. The way his knuckles bulged, and the thickness of his skin. The thick veins running down the back of his hand. It was apparent he's worked hard with them all his life. But still, I'm pretty sure this is not the same wonderful stranger who showed me so much pleasure that night in Reno. Regardless, I'm sure they would make for a wonderful time. He breaks in by asking, "Is there something wrong with my hands? You've been staring at them for quite a while."

Oops! I was still holding his hand during my entire inner monologue.

A little embarrassed I attempted to slyly test the waters. I asked if he ever has trouble getting into tight spaces with those large hands. He said, "I haven't found a space too tight yet."

That's it! I can't take it anymore. I have to see if I can take this anywhere. I raise my hand and spread my fingers and ask him to do the same. I hold our palms together and my finger tips barely reach his first knuckle. I tell him again how huge his hands are, then, grabbing his wrist and turning my back toward him I place his palm against my warm, firm ass. I tell him it's amazing how his hand even makes my ass cheek look small. While standing there, turned away from him, I hold his hand there a few seconds waiting for a response. Hoping it will be an affirmation and not an explosion of anger. And I am rewarded for my risk by a firm but quick squeeze. It felt nice.

I turned around to see him now smiling. He asked, "Did I feel lace?" I nodded yes, then pulled the waist of my pants down far enough for him to see the front of my panties.

I whispered to him "A good sissy ALWAYS wears panties, daddy."

His smile grew even bigger.

We walked to the kitchen, his hand still pressed against my ass cheek. He invited me to take a seat at the table as he went to the fridge and got himself a beer and me a watermelon wine cooler. He opened them both, handed me mine and asked, "Have you ever been on Craigslist? I met a slender little thing like you on there once who also called me daddy. I'm not sure what all you sissies do, but I can tell you that little sissy could do some pretty amazing things."

I blushed. Then asked him where he met that last sissy who could do amazing things. And when he said Reno my heart skipped a beat! I exclaimed, "Oh Daddy! I'm sooo glad you enjoyed me! I haven't stopped thinking about you since that night. The things you did to me, the way you made me feel I will never forget."

Daddy seemed to be just as happy as I was. He leaned across the table and gave me a big kiss, pulling my head towards him as he slipped his tongue into my mouth. I gratefully sucked his tongue as tears of joy rolled down my cheek. The kiss continued as I moved around the table to him and he grabbed me firmly by the ass and pulled me into him.

He asked, "How long until they come pick up the machine?"

I replied, "Monday."

Daddy said, "Good. That gives me three days. Are you ok with staying here until then? There's something I really want to show you."

I replied, "Yes, of course Daddy! I will stay as long as you like.."

As we continued to kiss I reached down and stroked his erect cock through the denim of his jeans. I pulled my head away and look down at his crotch. He gave me an approving grunt. I dropped to my knees and freed his swollen manhood. It was just as I remembered. 6 inches with silvery pubic hair that carried the musky scent of a real man.

I made daddy cum before he could finish his beer and I greedily swallowed his warm seed. When I stood up he fed me another drink of my wine cooler, set the bottle back on the table, then firmly grasped my ass with both hands as kissed me again.

He gave me a sharp squeeze as he asked if I'm still able to take him like before.

I excitedly replied, "Yes!"

So he sent me off to the upstairs bathroom to prepare while he said he needed to get his room ready.

I spent nearly an hour in the bathroom vacating and flushing, to make sure there will not be any mess. When I came out wearing just my panties I saw daddies cock twitch. I told him before we get started he may want to take advantage of my fuckhole pre-gape. He agreed and laid me over the bed on my stomach and entered me from behind. Daddy's dick felt wonderful inside my ass, and he grasped my neck as he pulled me towards him with each thrust. I moaned for him as he fucked me, and eventually he rewarded me by shooting a hot load in my eager ass. I liked how tightly he squeezed my little neck the entire length of his orgasm. It made me squirt a little from my sissy clitty onto his bed spread. I immediately apologized and licked it up best I could.

Now he got the Gun Oil out and as he lubed his hand and my hole he asked if I'm just as tight as I was last time.

I took this time to explain to him how ashamed I was that I was barely able to take his hand last time. I was too tight, and my hole bled as he forced his way into me. But at that time I had barely started taking a dildo about the girth of a soda can during practice sessions at hime. So after our encounter I was determined to stretch and improve myself. I needed to be a better sissy. I bought bigger plugs and dildos and started every morning riding a big Dick Rambone 14" rubber dildo, suction cupped to the floor of my shower. and each time I increased a plug size, I always slept with it the entire first night. I spent most weekends with headphones and big dildos, reenacting each scene of 2-hour all-anal gangbangs as i watched them, and binge-watching sissy hypno videos.

I tell daddy it should be obvious about now that all the training has paid off. I can now take things the girth of a baseball bat with relative ease.

As he began probing me with his fingers he said, "I can see you've been a very good gurl. You've made some great progress. I'm proud of what you've accomplished with your slutty hole."

I said "Thank you daddy."

He continued, "I'm glad you've made this progress, but admittedly I'm a little disappointed knowing it won't be the exact same sensation as you felt before. But then again, you can only claim a cherry once.."

I thought about it and realized he was right. If I'm expecting to feel the same sensation he made me feel before I am going to be disappointed. What made our first encounter so memorable was the pain and ecstasy that came with breaking past my limits and having daddy completely own me all night.

Thinking of this I said to him, "Daddy, please take your fingers out of my pussy. I don't want you to stretch and prepare me. I don't want a gentle gliding hand. I want to feel you force your way into me once more. I want it rough and dominating. Please."

He did as I requested and removed his finger. I laid there a while with no response coming from behind me. Perhaps I overstepped the boundary. Maybe I even killed the mood... but then all at once I felt him reach forward and grip my clit and balls, pulling them back towards him as his other hand plunged quickly and forcefully into my ass. He got buried as far as his last knuckles before grinding to a stop. From there he leaned into it, quickly applying more and more pressure as I was forced open, and I felt every additional centimeter slide through my rapidly widening ring.

As he did this he also pulled back harder on my clitty and testicles with his other hand. I let out a high-pitched scream immediately followed by fast paced whimpers as he tore into me. I had no time to react as he took charge. It took a moment to really catch my breathe, and by the time I was pleading "Please daddy! Please go deeper!" He was already buried past his wrist. But that didn't prevent him from attempting to go even deeper.

The further he pushed the further I wanted him to push. I didn't care about the limits of the human body. If he could have throat-punched me through my stomach like you see in the futanari videos I would've gleefully welcomed it.

But bodies do have limits, and he went as deep as he could before he just couldn't penetrate me any further. As he did I came on his bedding again.

He withdrew his arm to the wrist and proceeded to close his massive fist. It felt enormous balled up inside me. He commanded me to roll over onto my back, his fist remaining stationary as I rotated myself around it.

While on my back I rested the soles of my feet on the edge of his bed. But with his free hand he pulled them off the bed, leaving my legs dangling over the edge. This dropped my ass and pushed his knuckles harder against my belly. I reached down and gently pressed on the outside of my belly, feeling his hand inside of me. I asked him to please stay like that for a moment, so I can hold his hand while he is inside. His hand felt comforting. It felt like it belonged there. I felt completely fulfilled and satisfied.

He began to withdraw his hand and I asked him not to. But he didn't listen. He pulled out of my chasm and told me to clean his hand. At this moment I was glad I was so thorough when I cleansed earlier. And delighted to have him command me to be the dirty whore I am.

One by one I sucked his fingers, holding eye contact the entire time. My ass juices usually taste ok to me, but right now they tasted delicious. After I had done as I was told I pleaded, "Please daddy, please put it back inside and come lay with me in bed. At least until I fall asleep."

He agreed, applied more lube to his hand and this time he slowly and gently slide his hand back inside me.

As we lay there (head-to-foot more or less) he asked me about the training I've done with my sissy hole. The largest things I've taken, etc. I told him I've taken the Great American Challenge dildo without much issue, but a big black thick viened hard rubber 12" may be my favorite. Well, that and my 14" shower dildo. Impressed, he said, "Wow, I cant believe you can take a big dildo 14 inches!"

I clenched my ass around his wrist and I went silent for a moment until eventually he asked if something was wrong.

I didn't want to tell him, since he's been so proud of me all night. But I had to correct him.

"I can't take 14 inches" I said. "That's just the length of the thing. After 8 inches or so I bottom out..." "I've seen people in videos taking all the length, but I just don't know how.." "I'm sorry daddy."

With that I felt his hand creep deeper inside me. He was feeling around and investigating, but I didn't understand why.

Finally he said, "You have a wonderful ass which has been well trained, but you only trained the first sphincter. You have a second one up higher in your ass that is preventing you from truly taking your big dildos all the way. Up until now you've been cheat-fucking. You never actually conquered a large 12" dildo, you've only ever fucked a part of it. That's cheating... and that's not acceptable." "Now rest up tonight because tomorrow we are going to take this talented little boi-pussy's second cherry!"

The next morning after a hot shower I couldn't find my clothes, but daddy said I'm not allowed to wear clothes this weekend so that's ok. I like that. It just makes it easier for daddy to access me. Daddy treated me to a light breakfast of yogurt and fruit, and I helped myself to a fresh-squeezed serving of yummy daddy cum. As I sucked out the warm, delicious treat I looked up at him and listened as he further elaborated on last night's discussion of my little 'inadequacy'.

He reasoned that a good sissy should be able to take any dildo of length to the hilt, or else that sissy cannot claim to be able to take the dildo at all. Daddy's reasoning made sense, and I felt more and more ashamed the more he talked about it.

After completing my meal I remained on my knees, gently filling my mouth with his wonderful hanging testicles. I enjoyed the way they felt rolling around in my mouth.

Suddenly he stepped away, and my mouth made a wet popping sound as his left ball pulled out of it. Excitedly he announced he has a solution to my problem, and will ensure his sissy is the best sissy ever. He said he'd been working on it while I was asleep, and now it is time to get to work.

He lead me to a room downstairs with no windows. There was a big padded leather table in the middle of the room, and three cameras mounted to the ceiling, all pointed at the table. Along the wall were various mechanical linkages, hydraulic cylinder parts, and two large contraptions under sheets. It was carpeted, except around the table where it was smooth tile. There were also a few leather straps hanging from the ceiling and on the table. This was either a weird operating room, or Daddy has made the greatest sex dungeon I had ever seen!

My mouth was still agape in awe as he began to explain, "Do you remember the first time I had my entire hand in your pretty little ass?" "It was even bleeding a little it was so tight, and I said I wish I had a camera so I could film this remarkable ass of yours?" "Well now I do! I have cameras and so much more!" "So what do you say? Do you want to film you losing your second cherry this time?"

After a minute, standing at the door with daddy's arm around my naked body I stammered and finally found my words.

"Y-Yes daddy. I want you to film me becoming the best sissy I can be for you."

He had the cameras on with a few monitors in the corner, and next to the table was a large hydraulic sex machine with an unusual dildo attached. He invited me to climb on the table and lie on my back. I saw him smile as my limp clitty fell to one side. I know Daddy loves my clitty to stay limp, so he knows all my pleasure comes from my ass. I love it too.

With a large, wide leather strap he secured my chest to the padded table and did the same to my wrists with smaller straps. He put my legs in a sort of swing from the ceiling and hoisted them up until my butt was pulled off the table. He securedit in place then slid a wedge-shaped leather pillow under my lower back so it was resting comfortably.

As I'm laying there I look up to see two monitors mounted on the ceiling above my head. One seems to be setup with a constant feed of sissy hypno videos (which daddy knows are my favorite), and the other is a live feed from the camera looking at my now raised and spread asshole. I'm not sure which one is turning me on more, but now I am desperately trying to stay limp.

Now that I'm all secured and comfortable Daddy presses a button on a remote and the monitors in the corner turn on. I see the three camera feeds in one monitor, and I see what looks like chat boxes and men on their webcams on another monitor. Daddy sees me looking at the monitors and tells me, "I don't want to miss a thing this time, so not only are we setup to record, but we will also be live streaming this for free to multiple sites." "I want the world to know what an amazing sissy slut you are for me." "Isn't that what you want?" "Do you want to be the greatest sissy for me?"

I rest my head back on the table and respond, "Yes Daddy. Of course that's what I want. I want to be the greatest sissy you've ever had."

And with that I watch on the screen above me as he lines up my hole and his hand. He starts slow with a finger or two before easily fitting all four after last night's fun. He looks up and commends me for keeping my hole ready for penetration.

After he gets the thumb in he begins pumping in and out, and rotating his hand left and right. Gently coercing my sissy love-cavern to widen for him. And it does. Soon he is pushing the widest part of his hand through, and as he does this my sissy clit begins spewing cum down the side of my tummy.

I see the chat boxes in the corner are lighting up. Daddy gets his hand all the way in and my penetrated hole now grips tightly around his thick wrist. I now feel him moving his fingers around inside me, and he begins describing his actions to our audience. He tells me he is spreading his hand open to see how much room I have in there and if it needs to be stretched more with wider plugs or large enemas. Again the chat boxes light up, likely with suggestions or requests. But Daddy quickly changes the subject to focus on the matter at hand.

He reaches up deeper and I feel him reach it. He announces he's inserted a finger in my upper sphincter and is attempting to insert a second finger. I feel the pressure as he forces the second finger through my 'virgin' ring. After a bit of additional exploring, and a little fun tickling of my prostate he withdraws his hand. But not before first balling his fist and attempting to pull his hand out while maintaining as much of a fist as possible. And I watch with delight on the screen as my ass-pussy lips stretch and part with his hand's exit. He truly does have full control of me once again and I love it!