After taking it up the “hoo-ha” from Lizzie’s boyfriend, I wondered if she might finally have had her fill of tormenting me. Those fears were quickly extinguished when she approached me a week later.
Focused on her blog, as well as accommodating her followers, Lizzie started to show up with very specific demands for me. They often included props, increasingly ones that were inserted into my anus, as well as particular phrases that I was required to say.
Most of our sessions were limited to whatever items Lizzie could gather from around the house. She had a part-time job, but since neither of us had a lot of money to spare, she had to be creative. I did manage to spring for a bottle of sex lube, which made the insertion of whatever vegetable that would be given to me that week a bit more comfortable.
Then, one week in particular, Lizzie showed up with a new-looking pair of string bikini briefs and a bra top. Each had the word “Sissy” proudly displayed on both of them. They looked to be designed for a guy to wear, or more specifically, someone with a penis and no breasts. They fit me perfectly and I looked awesome in them! After getting all dolled up, I put on a great show for Lizzie. Then I lay on my back and tugged on my dick until I sprayed my load all over myself. Afterward, I ate all of the cum, just like a good “sissy” would do.
Once the show was over, Lizzie told me to keep the outfit. She explained that since she didn’t get any sort of financial return from her blog, she decided to set up an Amazon Wishlist so that her followers could purchase items for use on the blog. She wasn’t asking them to buy her a new iPad or anything like that. Her vow was that if a follower purchased an item from her list, she would either use it on me or make me wear it. The results would be posted on her blog and the contributor would get some additional media that wasn’t shared with anybody else.
The following week, things seemed to have returned to the basics. Lizzie made me put on one of her thongs, before sitting me down in a chair for extensive hair and makeup work. She applied a ridiculous amount of makeup to my face, making me look like an absolute tramp.
When she was finally done, she instructed me to bend over the edge of the bed. With no idea what she had planned, I expected her to pull out some sort of anal toy considering the way she had me positioned. Instead, she produced what I would generally call a flog. It was simply a handle with a cluster of leather straps hanging from it. Judging from the look she gave me, I could tell that she was going to enjoy herself.
Lizzie told me that I could make all of the noise that I wanted to, but I wasn’t allowed to move or protect myself. The first few strikes didn’t feel like much as the straps harmlessly splashed off of my backside. It didn’t take long, though, for the strikes to grow in intensity. Certainly, Lizzie was putting more effort into it, but there was also a cumulative effect from the repeated lashings.
She worked that entire area of my body over pretty thoroughly. Thankfully she had dressed me in that thong, which gave my balls just a bit of protection whenever her strikes landed that low. Although I couldn’t see how red my backside was getting, I could certainly feel how warm and sensitive it had become. Unable to stay still any longer, I rolled away from Lizzie’s assault.
Furious is the best way to describe how Lizzie responded to my attempt to avoid any more punishment. As usual, Lizzie had already anticipated how weak-willed I would be and brought a solution. She pulled out a pair of pink fur-lined handcuffs and waved them at me. After turning me onto my stomach, Lizzie climbed onto the bed and drove her knee into my back. At that point, she easily pulled my hands behind my back and engaged the handcuffs. She had one additional surprise as a ball gag with an elastic strap was stuffed into my mouth and slid into place.
The lashings got more intense from that point on. Any effort I made to get a break from the barrage resulted in my being kicked back into position. I quickly reached the breaking point, causing fluids to pour from my eyes, nose, and mouth.
Lizzie finally stopped her assault. Although she had already taken a lot of pictures during the process, she took great effort to detail the aftermath. I felt her fingers slide inside the back of the thong as she yanked it down to my knees. More pictures were taken as she documented the tanline-like discoloration on my backside from where the thong had been.
Although it seemed like a strange end to our session, I was thrilled that there was some direct interaction between Lizzie and me. Little did I suspect that she was just getting started.
“It’s your turn, Baby!” Lizzie squealed.
I wasn’t fooled this time, I knew exactly who she was referring to. Mike walked through the door just as I stumbled to my feet. I was positive that I knew what would come next. Mike was certainly going to slam-fuck my ass while he peppered my butt with slaps. I wasn’t looking forward to it, or anything else involving Mike.
“Get on your knees, Panty-Boy!” Lizzie ordered.
Since I already believed that I knew what was coming, I got down on my knees and slowly lowered my upper body to the floor, ready to take the next round of punishment.
“Look, Baby! He wants to feel your big, fat cock inside him again so bad that he is offering his boy-pussy to you!” Lizzie cackled.
Lizzie nudged me with her foot, “I said to get on your knees you cock-hungry slut!”
Once I struggled back up on my knees, Lizzie pulled the gag free and it dangled around my neck.
“Now you are going to suck Mike’s big, fat, manly cock,” she commanded.
Mike approached me, holding his erection in his hand. I tried to lean forward, but it was hard to maintain my balance with my hands still tied behind my back. His cock was neither “big” nor “fat” and I didn’t want to suck it in the least. Precariously leaning forward, I wrapped my lips around the head and attempted to bob on it slightly.
“Do it, Baby!” Lizzie shouted.
Mike immediately grabbed hold of my head and began to fuck my mouth aggressively. Even his modestly sized cock was difficult for me to handle and with my hands restrained behind my back, I could offer no resistance to his efforts to dominate me. As his cock closed in on the back of my mouth it made a clicking sound as it sealed off my throat, sometimes causing me to make a “glugging” sound as well.
I tried my best to breathe through my nose, but it felt like I was running increasingly short on air. Mike’s aggressive handling of me was also causing sporadic interruptions in my breathing. I started to panic as I feared losing consciousness, but just as it felt like I was in real peril, Lizzie ordered Mike to stop.
Initially, I thought she felt sorry for me, but she had simply made him stop so that she could take another round of pictures. I gasped for air as strings of saliva trailed from my mouth to Mike’s cock. As Lizzie held her phone in front of my face and reversed the image, I finally got a good look at myself.
The perception I had previously had of what Lizzie was trying to achieve had been way off. My hair was a tangled mess and snot and saliva were dripping off my face. Most of all, though, all of that makeup and mascara she had applied earlier was running down my face. I looked like one of the girls from a “face-fuck” video.
My reprieve would be short-lived, though. Mike jammed his cock into my mouth, once again, and seemed even more aggressive than before. His flabby belly mashed against my face as he efforted to stuff every bit of his cock inside my mouth.
“I have taken all of your holes now, Panty-Boy!” Mike gloated.
Again, I quickly found myself running out of air. As a panic state returned, I was sure that I was going to blackout this time. Mike grabbed my head and held his cock as deep inside my mouth as he could physically force it. From then on, I was forced to feel his orgasm in intricate detail. His balls tightened as they pressed against my chin. My lips could feel the flow of fluids inside Mike’s cock as his load was already on the move. Most of all, though, I felt the warm, thick splash of his cum as it coated the back of my mouth and trickled down my throat.
Just as Mike pulled away I gasped for air and sucked some of Mike’s cum into my airway. I coughed aggressively as an amalgamation of our bodily fluids trickled down from my mouth. Lizzie and Mike laughed as she continued to document my distressed condition.
Once Lizzie had her fill of this particular scenario, she placed her foot against my back and kicked forward. I crashed awkwardly to the floor, narrowly avoiding landing squarely on my erect cock (Yes, I did enjoy it in some twisted way, despite Mike’s involvement.) Lizzie handed Mike the keys to the handcuffs and he unhooked one of them and left the key inside. They left together, laughing about how pathetic I was.
Fortunately, as Lizzie started to receive more packages from Amazon, she was increasingly less dependent on Mike to help with her blog content. I waited for Lizzie to show up in a sexy outfit or a strap-on harness, but that never happened. In typical “Lizzie-fashion,” all of the items on her wishlist were for my use, or use on me.
Still, I held onto the hope that we would finally have a real interaction one day. Until then, I was forced to do things like model one of those butt plugs with an animal tail hanging from it along with some furry ears.
On a personal note, I really did enjoy my sessions with Lizzie. Even if most of the stuff that I had to do was humiliating, or wasn’t really what I would have chosen to do, it was still fun and it always made my cock hard.
I even made a new female friend at work. Her name was Mackenzie but she went by Kenzie, or as her name tag said “Ken Z.” She was incredibly short and petite, with brightly colored hair and a few random freckles. I think she was a natural redhead, but since her hair was always dyed it was hard to tell. Kenzie used colored contact lenses as well, which she would use to offset her look. She looked like a real-life anime character and was every bit as sexy.
One day, I even worked up the nerve to ask her out. Okay, I didn’t really ask her on a date, it was more that I asked her if she wanted to get Chipotle with me after work. It was a little bit awkward at times because we were both pretty shy. We did find some common interests, though, and I think that our meal ended a lot better than it started. I felt a lot more comfortable afterward and it gave me the confidence to eventually ask her out on a proper date.
In the meanwhile, Lizzie was busy keeping up with the demands of her followers. Some weekends, we had to do two sessions since people had already paid for items and were generally short on patience. There were lots of outfits for me to wear and I was beginning to worry that my stash of women’s undergarments and lingerie was going to be discovered, not to mention the anal toys.
The sex toy situation took a steep step up in the size department on one particular weekend. Surprisingly, Lizzie didn’t want to dress me up on that occasion, she simply smiled as she held something behind her back. She seemed way too happy about what she was about to do to me. That was alarming, to say the least.
“I got you a real dildo!” She said enthusiastically as she presented it to me. “It’s even bigger than I thought it was!”
Holy fuck, that thing was big! Okay, it was probably average-sized in the world of sex toys, but it was twice as thick and long as anything I had ever inserted before. It was roughly ten inches long with a big set of balls and a suction cup at the base. The real kicker, though, was how thick it was. I could scarcely fit my thumb and forefinger around it. I couldn’t begin to fathom how I was going to fit that monstrous thing inside of my ass.
Fortunately, I was afforded a bit of time to psyche myself up. That was because the other part of this particular fantasy was for me to have all kinds of derogatory things written all over my body. Lizzie even had a printed sheet of paper with all of the stuff that the contributor wanted written on me.
It was obvious how much Lizzie didn’t want to have to touch me in order to write all over my body, but that’s what she signed up for. With marker in hand, she wrote all kinds of things on me such as “Free Use,” “All Holes Available,” “Cumdump,” and “Lizzie’s Bitch.” She drew the outline of a pair of panties on me, as well as the words “Panty-Boy.” I even had a dick drawn on my face, along with the word “Slut” on my forehead.
With all of the prep work completed, it was time for me to perform. Lizzie ordered me to get on the floor and ride the dildo. I slathered both the dildo and my ass with lube and I lowered myself onto it. Even with all of my weight on the dildo, I couldn’t get it to budge. After watching me try multiple times, Lizzie was already getting irate. I tried in several other positions, as well as adding additional lube, but I couldn’t even get it started.
Not surprisingly, Lizzie was getting increasingly pissed at me. She asked me if I needed help, to which I eagerly agreed. That probably wouldn’t have been a smart decision even if she would have taken me up on it. Instead, she called for Mike, and I quickly offered to take care of the situation for myself.
Again, I tried sitting on the dildo, as well as twisting it slightly. After what felt like an eternity, the head popped inside of me. I remember when it felt like Mike’s cock was going to tear me in two. This was that feeling times one hundred.
I think that my body went into a mild state of shock. I froze for a moment as I gasped for air. Once I gathered myself, I climbed off of it and backpedaled. I stared at that thing in disbelief, as I still couldn’t believe that I was able to fit it inside of me.
“Alright, I told you it would fit. Now quick fucking around and fuck that thing!” Lizzie barked.
At that point, I was even more afraid of putting it back inside of me. My legs trembled as I tried to lower myself onto it. After a couple of tries, I managed to get it to go. I tried to ride it ever so slightly, but the strain was too much to bear, and I had to climb off of it, once again.
By that point, Lizzie was fuming. I tried to explain that I was working up to it, but she had little patience or concern for my comfort.
Determined to give Lizzie what she wanted, I mounted the dildo and forced it inside me. After cautiously sliding up and down on it a few times, the pressure was beginning to build. I asked Lizzie if I could stop several times, the last of which sounded more like begging.
She laughed at me and continued to shake her head in disapproval. While she certainly couldn’t physically stop me from pausing the action, my desire to please her prevented me from doing so.
Eventually, the dildo stretched my hole out enough to relieve the most intense part of the pressure. There was still some discomfort, but I kind of liked it. I started to ride the fake cock with increasing enthusiasm. My rock-hard dicklet thumped against my midsection as I switched direction from ascending to descending.
I could tell that Lizzie had transitioned from taking photos to video recording because she made me call out demeaning things such as “I love taking a big cock deep inside my sissy-hole!”
Although I was barely more than halfway down the length of the dildo, I think I was taking it like a champ. It was clear that Lizzie had documented everything she needed because she gave me the signal to finish it off.
I wrapped my hand around my extremely rigid cock. As usual, it didn’t take long for me to ejaculate. As I came, I gave one last effort to force the dildo into my hole even deeper. I virtually ceased all hand movement and just held a little pressure on my cock.
The first couple of sprays splashed against my chin and I could immediately feel cum dripping and running down my body. Each successive blast landed a little bit lower than the last until the intensity waned and my body drifted into a blissful slumping position.
As I looked at Lizzie, she seemed shocked about something. After scanning my torso, I could clearly see why….
