I Thought I Wanted It Rough... Ch. 02

I had just been fucked for the first time. I couldn't believe what I had just done. Some stranger had just used my ass for their own pleasure. Someone had stuck their dick INSIDE me. What was I doing? What kind of slut would do something like this? I didn't even know this guy, and I agreed to meet him, and let him pound my virgin hole.

Before I had made up my mind that I was going to go through with this...I had convinced myself this would be a one time thing. I would live out my fantasy of being controlled and fucked, and call it quits. I had more fantasies...but they were all so freaky, and I didn't want to be a slut. This would be an experience that would let me live out my fantasy, but limit my humiliation.

However, after having just been fucked hard, and rough by this stranger...I was scared by how much I liked it. I had imagined this as being an experience that would be intense, and probably very painful (which it was a little bit), and something I could jack off to for the rest of my life. But now, walking into the bathroom, I realized that I was more turned on than I had ever been in my life. I had even agreed to extend the session past what we had originally agreed to.

I looked at the floor of the bathroom at everything he had laid out. I guess to put it generally, it was a schoolgirl outfit. After all the transsexual porn I had watched in the past, I had a real fascination with cross-dressing. I had never done it, and certainly didn't expect to ever do it in front of someone else. But, after what I had just been through, and how it made me feel...I knew there was no way I wouldn't go through with this. I now looked more closely at exactly what he had left me. There was a small white shirt, a black skirt (that looked extremely short), white panties (a thong in fact), and white stockings. Sitting on the lid of the toilet was a gag that had a small dildo facing inward on it (it looked like it would literally make me gag), and a butt-plug that at its thickest point, was quite a bit thicker than the cock that had just fucked me.

My legs were a bit shaky as I stood at the door. I became vastly aware of my own cock for the first time tonight as it began to grow at the thought of what I was in for. Suddenly the door opened (knocking into me from behind). My owner (as I'll choose to call him, as I never got his name), looked at me with a disgust. "What the fuck is taking so long?" I just stared back at him not saying anything. "Fuck it...I'm going to go get some beer....hurry up and get everything on, and then put these on (as he sat the handcuffs in the sink). "

Just as suddenly, he shut the door. I quickly started toward my new wardrobe. I pulled the thong up and realized a small problem as my hard dick wasn't making this easy. I decided the best route was to pull my dick up towards my waist...then pull the thong up high so the waist band ended up around my belly button. This also resulted in the back of the thong sliding deep into my crack...likely disappearing. I pulled the shirt on, even though it was extremely tight. Next was the skirt, which presented a new problem. The skirt was not long enough to cover my entire ass. Either, I had to pull it down a little low, exposing the top of my ass crack...or pull it up higher, exposing the bottom of my ass cheeks. I chose to expose the bottom. Finally were the stockings, which really made me feel like a slut as I pulled each one up to mid-thigh.

The thought of being a slut, the feeling which I was hoping to avoid when this all started, only turned me on more at this point. Now it was time for the accessories. I grabbed the butt-plug and examined it. It was not long at all, but its thickest point was nearly as thick as my wrist. My face became flush at the thought of forcing this inside of me. I sat the plug on the toilet seat, and drooled liberally onto the tip. I then used my hand to make sure every inch got covered. I used the same hand (still with a little of my saliva on it), to reach for my hole. I pressed 2 fingers against my hole and was shocked as they slid easily inside of me. In the past, this sort of penetration was always extremely tight. Now, as they slid in, there was no resistance, and I could hardly feel them inside me.

I put my legs on either side of the toilet and lined my hole up with the toy and slowly lowered myself. I reached down and grabbed the base with my right hand as I continued down...contacting the tip with my hole. The first inch and a half went quickly, and the next inch felt incredible. The smooth plug was stretching my hole, which felt amazing, but only to a certain point. I was down about as far as it felt comfortable, when I reached up with my index finger of my right hand to feel how much was left. It was only about an inch, but I began to fear the pain I was going to have to accept to let this inside of me. I took a deep breath, and then released all the air from my lungs. In unison with the breath, I pushed hard with my ass muscles, and finally lifted the weight of my body off my feet, causing me to crash down on the dildo...impaling myself. Immediately I regretted this tactic as the waves of pain passed through my ass. Tears actually welled up in my eyes. I sat there for several minutes before the pain finally began to subside.

I reached for the gag as I continued to sit on the plug. It had some sort of harness that wrapped around the back of my head to secure it in place. The gag was in fact a dildo, that when I slid it into my mouth, ended up being just short of touching my tonsils. There was no way to make any noise at all, except the slightest moans as this fake dick filled my entire mouth.

As I stood to reach for the handcuffs, the butt-plug made me again aware of its presence...shifting inside of me, and actually making me feel a bit of a tingle over the radiating aching. I grabbed the handcuffs and opened the bathroom door. As I walked towards the bed, I clicked them into place behind my back.

I sat on the bed and my mind began to race. What was his plan? Cross-dressing in itself was hot, but was there going to be anything else new about what was next? Why did he give me such a huge butt-plug. He wasn't all that well endowed, and I began to doubt if I could even feel him inside of me after this thing had stretched me to its full girth. Then, I realized something else that was very strange/concerning. My clothes were no longer on the floor where I left them. What would he possibly be doing with my clothes?

My heart never stopped racing for the 30 minutes I was left alone in that room. Was he coming back? Was I going to be stuck here until the next morning, only to be found by the maid? The only thing I was certain of was that something was definitely wrong. My eyes shot to the door as I heard the key being inserted. My fears were realized when my owner was followed into the room by two black men. My eyes widened in fear...what had I gotten myself into?

From the moment the three men had entered the room, I was trying to think of a way out. Unfortunately, there were several problems with any plans I could come up with. One of which was that fact that I was handcuffed...behind my back. This left the obvious problem of attempting to open doors or driving home. Next, was that fact that I was in women's clothing. I didn't look anything like a woman, just a complete idiot dressed in really tight, revealing woman's clothing. What was I possibly going to do even if I was able to get out of this hotel room?

So, that left only one option...I had to tell my owner that this was too much, and I was no longer interested in continuing. Well...there was also a little problem with that. I had voluntarily put a gag in my mouth that made it impossible for me to communicate...just as I had voluntarily put the handcuffs on my wrists. I began to sweat, which I tend to do when very nervous.

"Hey slut, meet a couple of my friends," My owner said as he had a big smile on his face. He sat a brown paper bag down before coming over towards me on the bed.

I looked over at the two black men as they stayed standing near the door. Their proportions immediately got my attention. One of them seemed to be about my height (6 foot), but was enormously thick. I couldn't tell whether he was overweight, or extremely muscular, but he looked to be at least 250 pounds. The other man stood out as well, but not because of his thickness...but because of his height. He had to be a basketball player. He was easily 6 inches taller than his friend. I was visibly trembling at this point.

My master roughly grabbed me as he reached the bed, pushing me face down. I didn't know what to do...there was nothing I could do.

"Let me be honest with you slut," he said as he spanked my skirt-covered ass aggressively...his hand coming in contact with the base of the plug. As a quick note here...I had mentioned spanking in one or two of our e-mails. However, I didn't really intend for it to be this aggressive...more of just a slap on the ass while I was getting fucked, just to show who was in charge. I never wanted it be painful, which this was. The fact that he was hitting the base of the plug was just making the sensations all the more intense and overwhelming.

"I had a little more planned for today than I led you to believe in our e-mails." All through his talking he continued to spank my ass. The loud smacking of his hand against my skirt-covered cheeks (and the base of the plug), was making it difficult for me to hear exactly what he was saying. I think the heat of my red ass, the pain, and the sensation of the plug moving abruptly with each swat was also impacting my ability to focus on what he was saying.

Nevertheless he continued his swats, while revealing more of his plan. He told me that he worked with his friends over in the corner. He told me that they were both married, and that neither of them had ever had the opportunity to fuck an asshole before (their wives wouldn't let them near theirs). He said that when he showed them the e-mails I had wrote, with my kinky fantasies...they both were interested in getting involved.

I quickly regretted everything. Why had I been so graphic in our e-mails? I had exaggerated a lot of stuff with the assumption that they would never happen. I truly never thought I would be in a group situation, and had definitely gone overboard in describing what I wanted. I think I even described it in one of the e-mails as me wanting it to be similar to a prison gang-rape...each guy using my ass to get off, not worrying about whether I liked it, or if they were hurting me. I remember saying that I would pretend to struggle to make it more authentic, but I would really be loving every second of it. My God, if these guys had seen that e-mail, I was in for a horribly rough ride.

The relentless spanking finally stopped as he had finished explaining everything. I had shut my eyes at some point, overwhelmed by the sensation. I opened my eyes, my head facing toward the door...but the two black men weren't there. I quickly turned my head over to find both men standing on the other side of the bed...naked. They were both masturbating to the sight of my ass-beating. My stomach turned over when I saw what they were masturbating.

The shorter man...which I guess could now be called the muscular man, was not exceedingly long. In fact, he was likely only an inch longer than my owner who had fucked me earlier. However, he was enormously thick. He was thicker than the plug in my ass. It basically looked like he was stroking a beer can. I was in shock. I could very easily describe what the tall black man was stroking. It looked like a beer can, with another half of a beer can stacked on top. It had to have been at least 9 inches, but probably more...I'm not that great at estimating the size of things that I have never seen so big.

There was no way I could go through with this...I had to get out. I truly believed that I would die if they tried to fuck me with there huge cocks. Without the use of my arms, it really limited my ability to do anything, but I had to try. I quickly slid my knees up to my stomach...then lifted my head. My next move was going to be to walk on me knees off the other side of the bed and head for the door. This didn't quite work out.

The tall black man grabbed the back of my neck as soon as I raised my head up. His hand was huge, and practically wrapped ¾ of the way around my neck. With this grip, he violently slammed my head down into the bed, He removed his hand from my neck, and used it to grab my leg and pull it straight out again...then pulled it out wide, towards the side of the bed. The other black man had moved to the other side of the bed while this was going on, and grasped my other leg, spreading it out wide like his counterpart had just done. This left me flat, face down on the bed...my legs spread wide open on either side of the bed, with the black men both having a firm grip on my ankles. With the handcuffs, I was completely immobile.

My owner chuckled. I felt the bed shift as he made his way between my legs. He pushed my skirt up to my waste and pulled the string of my thong to the side. He grabbed the plug that was in my ass by the base, and began rotating it in circles, and spinning it. It was touching places that it hadn't touched before (hell, nothing had probably touched before)...and while it wasn't painful, it was a little uncomfortable. He then grasped the base and began to pull. The plug had been inside of me for quite awhile at this point, and was not releasing it easily. It felt like my ass was getting pulled off of my body as he continued.

Finally, it released...with more than a little pain. But, before I could dwell on it, he began to push it back against my hole. He was applying a lot of pressure, and it was just inevitable. It pushed back inside of me with a pop. It wasn't an audible pop, but my hole somewhat popped as it pushed back inside me. As soon as it was in, he again started to pull it out. He continued to push it in, and remove it for several minutes. The duration of this time found me squirming and writhing from the onslaught. By the time he had stopped, there wasn't any pain, but definitely a dull ache all around my definitely looser hole.

At this point, my owner got off the bed and headed across the room towards the bag he had dropped off when they entered earlier. I heard him rifling through it, clearly searching for something specific. When he found the package, he headed towards the bed, ripping it open. He pulled out what looked to be cuffs, that had long rope connected to them. He wrapped the cuffs around my ankles tightly. The black men pulled me by my legs to the bottom right corner of the bed.

In this position, my upper body was still fat on the bed, all the way down to my dick (which was smashed between me and the bed). My feet were both now touching the floor, on opposite sides of the corner. My owner then grabbed the rope connected to my left ankle and tied it to the bottom right corner bed leg...he tied it tight enough that my leg was stretched straight out uncomfortably towards the right bottom corner. He then grabbed the rope connected to my right ankle and tied it to the top right bed leg in the same manner. This left me with my legs tied so tight that they were slightly off the ground. I basically was part of the bed now.

The tall black man got onto the bed, on his knees in front of my face and began to stroke his enormous cock. I was actually thankful to have the gag at this time. He taunted me every couple of strokes by hitting my face with his hardness. I felt two big hands pull my ass cheeks far apart and then a large amount of saliva landing directly on my hole. Accepting my fate, I quickly allowed my hole to open, and the saliva to slide inside of me...knowing I was going to need every bit of lube I could get.

"Oh, they aren't going to use condoms," my owner announced. "They are married, and you're a virgin, so it's all good."

"Break this bitch in...get her tight ass ready for me," the tall black guy encouraged his friend.

I felt the thickness as it slid up my crack, making contact with my quivering hole. I prayed that the plug had loosened me up enough. I prayed that these guys were clean. I prayed that it felt good. I prayed that I could please them. I prayed that I stop being such a slut.

Then he began to push...