I had been chatting online with Christina for a few months and was looking forward to meeting in person. We shared an interest in kinky sex and planned to spend the weekend in a cheap motel room. Though we didn't live in the same town, we were only a short drive away if we shared the distance so we met in a smaller town at about the half-way mark.
I made the short drive in good time and checked myself into the motel. I sent Christina a text to let her know which room I was in and got myself settled. I brought several of my favorite toys with me and had already given myself an enema before I left my place. I had also shaved off all of my pubic hair, leaving my penis and asshole smooth and soft to the touch.
Though we both liked to switch, Christina was more dominant so I agreed to start things off as the submissive. I stripped off my clothes except for a silk thong that I purchased just for the occasion. Christina thought the thong was hot but I felt somewhat emasculated in it. I was to leave the door unlocked and slightly open so she could walk right in while I waited on my knees facing the door in only the thong. Anyone could have opened the door and seen me there and the idea both scared and excited me since they surely would have assumed I was gay. After a few minutes I started to have second thoughts about the entire meeting. My experience with women was limited and I had never explored any kind of kinky sex with a partner. My mind kept on this course until I was just about to chicken out and leave when the door flew open.
Christina walked in looking stunning, just as in her pictures, and immediately took control. Shutting the door behind her and dropping her backpack on the floor, she grabbed me by the hair and bent me over the bed. Pulling my thong slightly to the side, she worked her tongue up my ass as far as possible. It was the first time anyone ate out my asshole and I loved it. While she worked her tongue, she reached around my waist to squeeze my cock and balls through the silky pouch of my thong. It didn't hurt, but it emphasized her control over me.
"I thought you were a switch, but you seem more like a submissive little bitch to me" she teased. I responded only with moans to her licking and squeezing. I didn't want to admit it but I loved the degrading way she was talking to me. "Let's see what you've brought for me to play with. Stay where you are and don't turn around."
Christina rummaged through my bag for a minute, examining my small collection of dildos and butt plugs. "You didn't bring any lube! Good, I didn't plan on letting you use any anyway." I heard her move to the other side of the room and open her own bag. "The first thing we should do is make sure you can't get away." The next thing I knew, Christina was securing leather cuffs to my wrists and a leather collar around my neck.
I was now keenly aware of my near nudity and prostrate position while Christina was still fully dressed in jeans and a button down shirt and standing over me. She produced a chain which she looped through the rings in my cuffs and then padlocked to the head of the bed. There was plenty of slack, but it was clear that I wasn't going anywhere until she decided it was time for me to go. "You definitely won't be getting out of those until I decide." She dangled the key in front of me for a moment from a chain and then pulled it away quickly and secured the chain around her neck, the key dangling neatly between her breasts under her shirt. It seemed that I had completely lost control of the situation and my playmate for the evening had become my dominatrix.
She spanked me hard a few times. "Ouch," I objected.
"I just want you to remember who's in charge here," Christina retorted. "Now open your mouth." No sooner had I complied than she shoved a black rubber dildo into my mouth. It was long and thick with a handle on the end that my self-appointed mistress was holding. "That's good, pet. I suggest you get it nice and wet unless you want this next part to hurt a lot."
It did not take me long to figure out what she meant so I did my best to slobber all over it before she tired of this part of the game. Withdrawing it from my mouth she stepped behind me and wasted no time in pressing it to my asshole. Thankfully it was still moist from her licking because she didn't even try to ease it in - rather shoving the entire length in as hard and fast as possible. The size was shockingly large in my ass and I couldn't help but scream but almost as soon as I opened my mouth, it was filled with a rubber ball gag, which Christina quickly strapped around my head. Obviously, she had this all planned out and if it was not clear before, then it was clear now that I was totally at her mercy.
"I'm going to need you to keep the noise level down, pet. Comfy?"
I shook my head to indicate that I was not and had no desire to be gagged like this.
"Good," she replied and resumed her vigorous fucking of my ass with the big black rubber dildo. "I do love this ass of yours, so tight and pretty, almost like a girl." She spanked my twice as she said this. "You're my pretty little bitch, aren't you?"
The way she was fucking me was painful at first but then started to feel good as my ass started to get used to the assault. Eventually, my anal mucus started flowing in response to the relentless dildoing. Christina noticed and exclaimed, "Oh my god! You're ass is getting wet like my pussy! I didn't know that could happen! You really are a little bitch, aren't you?"
All I could reply was by moaning as she fucked me even harder since the gag in my mouth prevented me from saying anything comprehensible. Eventually Christina tired of this game and pulled out from my ass. I felt suddenly open and empty without the dildo there. I tried to turn my head to see what was happening but my mistress had ducked into the bathroom. I heard some rustling and continued to wait with my ass high in the air. After a minute, I heard her return and turned to see her still fully dressed but now sporting a huge strapon dildo on the outside of her jeans. It was significantly thicker and longer than the dildo she had just been using.
"Your ass is still gaping wide open and leaking ass juice all over the bed so I don't think you need any warming up for this big boy." And with that she positioned the new dildo against my asshole and started to press it in. Unfortunately for me, it was a little bigger than my hole and caused significant pain. I screamed into my gag. "Hmm, perhaps I misjudged the size of this thing. Don't worry I'll get it in." My eyes were as big as saucers as she pushed even harder. I could feel my anus slowly stretch to accommodate the new toy and eventually it popped all the way in. "Yes! I knew I could get it in," she boasted.
Christina started fucking my ass in earnest now. I thought I would tear in two from the size of it but she showed me no mercy. On and on she fucked for at least 20 minutes. It seemed that she never tired of this game. Chained to the bed as I was and gagged, I had little choice but to take what she gave me. It was an intense mixture of pleasure and pain. Eventually my asshole started to spasm involuntarily as I tried with all my might to push the giant dildo out of my ass. Finally, Christina tired and pulled out. She moved to my head and removed my gag. "Did you like that, pet?"
"Yes mistress," was all I could get out as I tried to catch my breath and regain my senses.
"Good. Now it's time for you to get to work. My cock is dirty. Clean it up, bitch."
I looked at the dildo still attached to her waist. It was covered in my own ass juice and a small amount of shit. "But, but..."
"But nothing! Suck that cock, fagot!" I was so shocked by the sudden forceful order that my jaw dropped. Wasting no time, my mistress pushed forward and popped the cock right into my mouth. It was disgusting! I could taste my own ass and shit as she now fucked my mouth. "That's right, slut. Lick it all clean. You're going to like what I have planned next."
Once I had sufficiently cleaned her strapon dildo, she moved back behind me again. She grabbed my cock and balls through my thong pouch and gave it a good squeeze. Her other hand started rubbing my ass tenderly. "I hope I didn't ruin your asshole forever. It's much larger now than when we started. In fact, I bet I could fit my whole fist in there now. Let's find out!"
"Oh please God no!"
"Oh, it pleases your God yes," she quipped.
She started with four fingers easily enough and then tucked her thumb in beside them and started fucking me with five fingers for a bit. "Things are getting a little too dry back here so I'll do you a favor and let you lick my fingers." Into my mouth went her fingers as she gave my balls a more forceful squeeze to let me know that she was not interested in what I wanted. I drooled as much as possible all over them because I knew that her fist was going in one way or another and I preferred not to have my own blood used as the lube.
Moving back behind me, Christina spit a copious amount right onto my asshole and started pushing her hand slowly but surely into my asshole. She worked it in and out for a bit and then gave one big shove popping her entire fist in. I cried out in pain and she just laughed.
"I love having my own anal slut to play with! I could do this forever!"
It seemed to last forever as she twisted her hand in my ass feeling my most private places and then pounding my ass with her fist over and over again. It stretched my asshole to the limit and just when I thought I could not take it anymore, Christina stopped and pulled out.
"Wow, I'm exhausted! I need a break," she announced and moved to the bathroom to wash her hands leaving me on the bed panting and exhausted myself. Just as I had caught my breath, Christina returned from the bathroom. "Now, let's see what I've been squeezing all this time." And with that, she pulled my thong down and immediately started laughing. "Wow, that is the smallest cock I have ever seen!"
"What? No, it's average size."
"Sure, for a 10 year old. Look, I know I said I would have sex with you but I was expecting you to have something between your legs. There is no way I could get any pleasure from that. I need a real man's cock to get off."
I couldn't believe what she was saying. My heart sank as she insulted me. All I wanted to do was crawl away as soon as possible and hide but almost on queue there was a knock at the door. "Oh, they're here," she said.
"Who's here?" I asked.
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