Reminiscing on My Sissy Life

Things have gotten wild since my ex-wife mistress first took control.

I've done everything she has requested of me. And with each accomplished task she only adds more challenges.

I've never failed her yet, and yet she never ceases to ramp things up.

In case you aren't caught up just yet, this all began one day when she stumbled across my secret fetish: I craved to be a sissy fuck slut. She found my dildos, my buttplug and my girly clothes. She then used them on me in a violent manner that makes my clitty drip precum just thinking about it.

She made it her goal to break my ass, and I have never been happier!

Tonight I'm sleeping with my large buttplug. A few months ago it would have been far too big to fit comfortably enough for me to sleep, but thanks to my mistress, tonight feels wonderful.

I continue to ride a big rubber dildo in the shower every morning like she said. It's a refreshing way to start the day. Then I slip into panties, and sometimes a plug, before heading off to work.

Sometimes she texts me before lunch with a new task. That task usually involves having me meet her at a truck stop to earn my "protein-shake" lunch from a driver she's been flirting with. She doesn't actually care for truck drivers herself, but she found its an easy source of cum to feed me. Just find an occupied sleeper, flirt a bit, start a hand job, and ask if her friend can suck his dick and eat his cum. They all say yes. Even when they find out it's a man, by that time they don't care.

I remember the first one I sucked. He was Mexican, shaven, cut, and about 5". I remember pushing my face all the way down into his crotch, my nose pressed against his pelvis with his cock pressing into the back of my throat. I could smell his manly balls so I sucked them, but I must've been too eager cause he made me stop since I was sucking too hard. I remember the feeling of his meaty head on my lips and my tongue. It was wonderful finally having the chance to enjoy a man's penis.

The rest were all pretty similar. Some were larger, a lot were smaller. Some cut and some uncut. But the flavor and musk of an unwashed, uncut man's cock drives me absolutely wild. That first minute of sucking is absolutely divine. And then of course they all cum. I noticed many men will push your head down all the way into them as they cum, shooting straight into my throat. But I prefer the ones who blow it in my mouth, so I can taste it and swish it around for a while before I get back to work.

The cum is the biggest difference i noticed. And not just load size, but flavor. Some cum tastes nutty, some a bit sweet, but my sissy tongue loved every drop I was allowed to have.

But that's about the only time I'm not dressed when she plays with me. We both prefer I look girly before any games begin.

We usually focus on size fetishes, but she also gets some good ideas for other kinky areas to experiment with as well.

For example, have you ever eaten really spicy food and your insides burn? Well, one day she greeted me with two movie tickets and said we had to hurry to get there on time. But first she reached into her purse and pulled out a bag of habanero peppers. I was confused at first, until she had me bend over and pushed six of them inside my boipussy and capped it off with a buttplug. But surprisingly it didn't burn. Not until we walked from the car to the theater and sat down. I don't know if it was the walking or the sitting, but when the peppers broke open all hell broke loose! It burned so fierce, my face was sweating as I winched and whined through the entire movie. She told me I had to be good and sit through the entire show and she would reward me afterwards. So I obeyed.

It's a different type of hot, not the same as it in your mouth. It's bearable, but feels like you cannot maintain control of yourself. And the heat stays. It does not dissipate with time.

After the evening matinee (to this day I have no idea what movie it was), we returned to my house where I was allowed to purge. The relief was instant and felt amazing. Things began to cool, but a constant heat feeling remained. Not burning, just really warm. I returned to the bedroom to find her waiting with a bucket of large ice cubes.

We were about to go to the next extreme. By comparison, I'll take the ice any day. But never before have I felt such extreme sensations of temperature on my boipussy. It truly was a thrilling experience. But one we never need to repeat...

Except one time an ambitiously girthy icicle hung from the eve, which just begged to play a role in a spontaneous fantasy. She pretended to be the ice queen. I was her servant. She broke off the tip and had me suck the end until it was rounded and my lips were numb. I was strapped to the bed and she slowly slid it deeper and deeper until I swear my chest got cold. It felt the coldest against my sissy pussy lips. The inserted length could not be felt as much. So when my boipussy could no longer feel it from the cold she would remove it, tongue my frozen hole deeply, and warm me back up. But only to then reinsert the frozen shaft, and repeat until it was melted and I was laying in a puddle.

But like I said, primarily it was about size. The larger dildos about the girth of a soda can began to feel natural and comfortable as she bent me over with the strap on in our now natural routine.

She figured by this point I should be able to handle about anything and had me get online to find daddies to tame my constantly hungry fuck-hole. I did a good job of attracting horny men. I made it no secret my intentions were to be their willing, personal sex toy. Everyone wants pics. Many want video. Some want very specific video.

All the attention from men wanting me to pose for them as they described the terrible things they wanted to do to me made me feel so special and oh so horny!

One online daddy in particular had a fetish for seeing how big I could go. My biggest buttplug wasn't enough. My biggest dildo wasn't enough. Two dildos at once just spurred him to demand I sink my hand all the way down to my slender, delicate wrist. I was able to comply. Then he said something truly shocking. He wanted to see me fuck a baseball bat!

So I went out and bought a youth-sized bat, went to the bathroom and slowly squatted down over it. As i slowly lowered all my weight down on it my hole began to give way and opened enough to just barely fit around the wide end of the bat. I continued to slide down the shaft as deep as I could, and as I scare-crowed myself on the baseball bat my soft clitty began spewing load after load of sweet cum. It was an indescribable sensation. I met my toughest online request and had the most amazing orgasm doing it.

But as much as I love the online attention, getting a real man to dominate you in person is actually kind of rare from the online groups.

The first trick is to get a hotel room. Men feel much more comfortable meeting you in a hotel.

So one night I lined up 2 men. The first was a pretty generic blow and go. He was maybe 4 inches. I sucked him in my pink panties and a big buttplug inserted. He wanted to fuck me, so of course I let him. I couldn't really feel his cock in me so I clenched my hole, but he slapped my ass hard and yelled at me, telling me not to make it tight, he wanted to fuck a loose slut! He got his wish, and he finished inside me. But I was able to get a little ass-to-mouth before he put his pants on and walked out of the room, leaving me on my knees craving more.

About an hour later the main event started. A silver daddy who knew just what he wanted. I answered the door in sissy attire, plugged, showed him the large dildos laid out and told him he's free to do whatever he wants. He dropped his pants by the window overlooking the city (about 10 stories up) and I pulled down his underwear to see his limp dick and shiny silver pubes. I put his soft silky penis in my mouth, hands behind my back and started sucking him as he enjoyed the view from the window. I think we were both hoping someone on the street would see us.

He was about 5" erect, cut, and trimmed balls. I asked him in our emails if I could suck him for as long as I want and he agreed. So I took my time and enjoyed sucking his dick at the window for about 30 minutes before he took me to the bed, on my back, with head hanging off the edge. I opened my mouth and he thrusted into my face like he was fucking a pussy. His balls slapped against my face as his cock pushed to my throat. It was a great position for anyone who likes to be dominated. Then he flipped me around, removed my plug, rimmed me then looked at my dildos in disbelief that I could take them. So just as I did before the first time my mistress fucked me, I took each toy and showed him I was a cock whore, then let him take over. It didn't take him long to fully realize there were no limits in this room. Nothing taboo. That's when he got that sadistic, dominant look as he stood over his helpless, willing sex slave, and the fun really began!

He decided to shove a double dong in at the same time as the biggest dildo. The stretch from the double anal penetration felt amazing, and with him controlling depth and speed, my eyes rolled back and I squealed like a girl as he fucked me hard, with no regard to what I felt. He wanted to see how fast and deep he could move those dildos in my ass. And that was his right. The fact that he gave no consideration to this sissy's feelings as he used my body for his own entertainment was a huge turn on.

When he finally stopped and pulled out I was a rutting whore, begging to be fisted. (After all, I had done it once before.) My daddy had huge sausage-fingered hands and wrists larger than my ankles, so he was skeptical, but he lubed up and did it anyway. He made a cone shape with his hand and pushed into my already gaping hole. I could feel as my ass got tight again his knuckles reached my lips. I was afraid he wouldn't be able to fit so I began pleading for him to "Please please put it in. Please put it all the way in me!" And he kept pushing until he forced his whole hand, all the way to the wrist, inside my hungry quivering hole. I was on cloud 9 at this point. I screamed in ecstasy as he moved his hand all around, back and forth, in and out of me. He informed me I was bleeding. I figured I would be. I'd never gone that big before. But I didn't care and it never deterred him from exploring just how loudly he could make me squeal. At one point he even reached up with his other hand and gripped my balls, squeezing them until my sides hurt as he continued to force his hand quickly in and out of my ass, trying to make more and more of a fist each time.

I was completely unable to get hard but I still cummed all over the bed. My cock truly was nothing more than a useless limp clit on a fuck-whole slut, just like I had always wanted. Finally he tired and withdrew his hand one last time. I lay there with my whole body quivering, unable to move. He grabs my head and has me suck his dick to completion, and I swallowed.

I then got off the bed, limped to the bathroom and washed my hole as he turned on the tv. I returned to the bed and he let me nestle between his hairy legs, with his now limp dick in my mouth. I was allowed to suck on it and enjoy it for over an hour, until he finally said he had to go. But before he left he called me a good slut, and said if he's every in town again he wants to film all the amazing things I can do.

For the rest of the night I lay there with the taste of cum still in my mouth, and with every clench of my gaping asshole shooting hornies all through my body again. I put my big plug in and went to sleep feeling completely satisfied.

That was by far my best experience with a daddy, and my mistress was right to make me wait until I had widened myself enough before doing so. When a sissy offers herself to a daddy, or any dom, she needs to be prepared for no limits action. Cause that's the best part about fucking a sissy.

Soon after my mistress upgraded me to the Great American Challenge dildo, but not without first parading me around the store, loudly clarifying for anyone else in the store that the whore she was leading around on the leash was going to take the entire thing in her ass. I felt proud she had that confidence in me. And I had no difficulty with the girth. But now she says I really need to focus on depth training. I agree.

She has since upgraded the size of my daily shower dildo, and i've taken on a new role as her toilet slut whenever she comes over or spends the night (Or in an outhouse, or camping, or wherever). Nothing too bizarre, she just doesn't use toilet paper when I'm around. Instead tells me when she needs to potty and i follow. When she's done she stands up, turns around and spreads her cheeks to allow me to lick her holes clean. The trick is to always end with the butthole.

If she wants an extra-long cleaning session she will make it clear by reaching back and placing her hand on my head. My Goddess should never have to wipe herself with rough paper. And i love every opportunity she gives me to taste her.

Well, like I said. Tonight I'm just laying in bed with my boipussy comfortably plugged. Reminiscing on how I got here and all the wonderful sexual experiences I've been able to enjoy thanks to my beautiful, loving mistress. Goodnight.