Meeting a stranger in a hotel room

Meeting a Stranger in a Hotel Room


A few weeks after my confrontation with Ron, my friends Bob, and Rich debating cross-dressing, I was depressed. I was depressed and knew that I would have to be Cindy soon to feel normal again. Dressing and doing my makeup always made me feel better and made me horny. I posted a request to meet a dominant man on a cross-dressing website where admirers were known to cruise. Within in a few days, I received several replies to my posting.


One reply was interesting because of his strange request. He wanted to meet cross-dresser in a dark room. He did not want to see the cross-dresser’s face or to be seen by the cross-dresser. He e-mails expressed his desire for the lights to be out and the door unlocked. He told me to dress only in my stocking, suspenders, and bra.


What he proposed was truly anonymous sex, which was something I enjoyed. I replied to him I would rent a hotel room and dress, as he asked. I agreed to be lying on the bed, pretending to be sleeping. He liked the arrangements and set the day to meet. I arrived early, dressed, and did my makeup. A few minutes before the stranger would arrive I placed the do not disturb sign in the doorjamb next to the lock allowing the door to be shut but not locked. Anyone could have pushed the door open to enter.


At seven PM, I was lying on the bed in the appointed position, the lights were off, and the room was dark. A few minutes later, the door opened flooding the room with light from the hall. The door closed making the room dark again. The stranger did not tell me much about himself, just he had never met a CD before, and wanted his first experience to be as anonymous as possible. I did not know whether he was black or white, young, or old. After the door closed the strange make no sound or could I hear any movement. I guess his eyes were getting used to the dark. After a minute or so, his hands touched my back then moved to my ass. In the dark room, he felt my body confirming I was naked except a bra, suspender, and stockings. Everything seemed to be as we agreed.


It happened so fast! His weight was on top of me, holding me down. I could not move anymore. With one swift motion, he had my hands by my side pinned by his knees. Positioned on the bed face down, helpless; I could not offer any resistance. I tried to yell. The stranger said, "Shut up bitch!" as he cups his hand over my mouth. His hand muffled all the sounds I could make. He removed his hand from my mouth, I tried to yell again but he stuffed something in my opened mouth. I heard duct tape being ripped from a roll. Quickly the tape was used to secure my mouth shut.


He grabbed my arms by the wrist, tying them with something silky like stockings or pantyhose. My hands were bound fast restricting my arms. The stranger slipped some material over my eyes and fastened it tightly around my head. Gagged, blindfolded and bound, I was a half-naked cross-dresser lying face down on a bed.


I heard the rustling of clothes, the unzipping of pants. He sat on the bed next to me. He touched me, starting with my shoulders, then the touch of his hand moved down my back. I tried to move away from his touch. His hand moved all over my back then moved to my behind. He felt the suspender, stockings, and the rest of my naked body. His hands moved to my waist then grabbed each cheek firmly.


Then whack, whack, I felt the pain of two slaps on my ass cheek. I assumed it was his hand. He said with a sound of power over me, "Cindy is a bad girl letting a stranger come into her room.” Whack, whack was the sound I heard, I felt the stinging on my backside. "That is why I am here, to punish naughty Cindy.” Whack, whack, each spank was getting stronger.
He began, "Fucking American Cunt, fucking every man who wants your sorry ass.” Whack, whack, "You like being a bad girl don't you, slut Cindy?" My backside was getting sore with each slap. My cheeks were bright red and warm to the touch. Whack, Whack!


I wondered whether anyone in the hall or other rooms could hear the misuse I was receiving. His hand slapped my cheek and pausing while his finger would explore my crack. His finger massaged around my hole. After the tenth slap, his finger violated my anus. He exclaimed, "Your cunt is taut your filthy bitch. I am going to give you something to think about the next time you post a personal advertisement on a Yahoo!” He stood and dragged me to the edge of the bed positioning the upper half of my body on the bed’s edge. He stood between my legs, spreading them farther apart. I felt him place one hand on my ass as he pulled my cheeks apart. He rubbed his cock down my crack seeking my hole. He found my man pussy and pushed his cock head past the first set of sphincter's muscles, causing some pain.


I thought, ‘ouch that hurts’. ‘He must be thick, relax, and accept his dick’ I told myself. I was glad I had put some lube up me arose before he arrived, or it would have hurt more. I squirmed pretending to move away from his dick but trying to get the lube to work. He laughed, "Oh Cindy you cannot escape from me. I am going to enjoy your sweet cunt.” He pulled on my hips, thrusting deeper.


The lube was working as his cock worked deeper into my cunt. I moaned into the gag as if I were in pain, I was not but it made the man think he was hurting me. Some men get off thinking they were hurting someone by forcing their cock into an ass. I know that a man's rectum is longer than a woman's pussy and men with large dicks like ass fucking better than pussy fucking. This stranger’s cock felt larger than a typical man. I am skilled at anal sex, but I have my limits of eight inches long and four inches around. This stranger’s cock felt longer than eight inches. His cock caused me pain when he pushed in deep. Then I felt pleasure when his cock would rub against the prostate. Large dicks are a pain but pleasurable. This stranger was becoming a pain in the ass. I sensed he enjoyed inflicted pain when he ass fucked a guy. He claimed with self-satisfaction his voice, "Oh Cindy you are such a whore. I love forcing you to take my cock into your fucking cunt.” My eyes were covered, I could not see him, but I pictured him watching his cock go deep into my body.


I tried to relax, allowing his cock to go deep inside me reducing the pain. Just when was used to this position, he stopped, rolled me over on my back and dragged me to the center of the bed. I was lying on my arms. He grabbed my ankles, raised my legs, pushed his cock deep into me, and fucked me in this position. Talking to me as if I am something to be used, he stated, "I am going to teach you to enjoy my dick. Do you like my cock fucking your sissy cunt?” I do not think he expected a reply with the gag in my mouth.


All I could answer was, "Ah, ha,” I tighten my anus muscle causing more friction giving him more pleasure in each thrust.


His fucking speed increased, as he announced, "Oh you are a fucking cunt, I am going to cum. I am going to pump you up full of my seed.” With one thrust forward, he impaled me as far in as he could. I felt a warmness squirt far inside me. I loved counting the number of squirts each man would deposit in me. With each squirt, I contract my anus muscle responding to the deposit. He tossed my legs aside, making me feel like a piece of meat. He left me on the bed, tied, gagged, blindfolded, used and dripping his seed dripping from my misused manpussy.


At this point, I expected him to untie me and leave. Instead, I heard a phone dial tone and the dialing of numbers, and he said, “Two-One-Seven.” Slowly saying my room number.


A few minutes later I heard the door opening, then the sound of footsteps entering the room. I felt the presence of several men in the room, maybe three or four. I thought this could not be good. A new voice asked, “What a fucking bitch, what is her name?”


The stranger said, “Cindy the slut.”


Another voice said, “I want a piece of that ass.”


A voice deeper than the others announced, “I need that fucking hot mouth on my cock.” I realized that I was going to be raped.


My mother uses to say, “When you are going to be raped, you might relax and enjoy it.”


The tape over my mouth was removed and the material in my mouth was removed. Someone whispered into my ear, “Cindy, now you’ll be a good girl and you will not be hurt. Otherwise, you will get punished. You will not enjoy the punishment, you’d better be a good girl, and do you understand?”


All I could answer was “Ah-Uah .” I had bondage fantasies about gangbang fantasies. Then I was not sure whether I was ready for what was about to happen.


I felt my body being moved and positioned on the bed. Pillows were placed under my chest allowing me to be kneeling on the bed; my face was on longer on the bed. The pillows allowed my face to be at an elevation that made allowed someone to stand and fuck my mouth and someone else to screw me. I steadied myself knowing my warm body would be used for the pleasure of horny men.


As my eyes got adjusted to the light, I got a look at the men in the room. One man was leaning on the dresser, a cigarette in his mouth and a bean? in his hand. Oh, shit, I recognized him. I knew him. Ron, a friend. Just a few nights ago, I met him in a bar and we had a long conversation about cross-dressing. I looked at the other two men, I recognize one was Bob and the other was Rich, two more of my friends were in the bar. Oh, shit, oh shit, so far, they have not recognized me as Matt, only Rich knew my identity.


I was tied up with duct tape and could not move. My body was positioned for a double assault. One man fucking my ass and another fucking my mouth, split roasted as my English friends would say and there was nothing I could do against it. Rich knelt on the bed, bent over, and whispered into my ear.


“Hey Matt, you look so sexy. After our conversation the other night, I wanted to know what it felt like to get oral from a cock sucking queer. Then Ron told me about an ad he saw on yahoo and I suspected it was you when the ad was signed Cindy.” Do not worry, I will not tell Ron that Cindy is Matt if you give me your best blowjob. Bob is going to fuck you know and does not know that you are Matt, so it will be our secret, right?”


I shook my head yes and whispered, “Yes”, Rich knelt next to my face.


Rich said in a loud voice, “Open your mouth bitch and suck my cock.” I did as he ordered.


I heard Bob’s voice saying, “What a fucking queer bastard, dressing up as a woman and letting me fuck him. I am going to enjoy breeding this cunt.” I felt the warmth of a cock between my cheeks where Ron had fucked me hard a few minutes earlier. I had lubed my ass but now I had Ron’s seed in me and dripping out running down my leg. Bob’s cock penetrated my ass with no pain. I could feel I had a cock in my ass, but it did not feel long or fat around. Bob was bouncing his body off my ars, slapping my ars as if he were riding a bull and yelling, “Yippee!”


Rich held my head guiding his cock into my mouth. I gagged when he forced his cock into my mouth. I guessed he had seven inches and was lucky his cock was not fat. Rich continued to fuck my face telling me, “You have a hot mouth bitch. Keep sucking you fucking queer.” I was not able to say no. This was one of my fantasies so far none of my friends to realize I was Matt.


Bob continued to pound away at my ass and Rich fucked my faced. After five minutes of this fucking, Rich said, “Oh yes slut, I am coming, I am going cum down your throat and you will swallow every drop.”


The Bob chimed in, “Oh yes, I cummings too. I will breed your ass you are a fucking queer cunt. I could feel the warm flush down my throat of Rich’s cum and felt Bob warm cum filling my ass. As both men pulled out of my body I looked at Ron, still standing naked leaning against the dresser and filming the split roasting of Cindy.


“Oh shit,” I said to myself. Now they might recognize me, and I will never live this down. I turned my head away. The duct tape was removed from my hands. I was pushed over on the bed, too tired and used to move. The three men dressed calling me names, like cunt, whore, queer, cocksucker, laughing about what they have done, raping a helpless CD. Only Rich knew I was Matt so far, he had kept the secret. As the men left the room, Rich leaned down and whispered into my ear. Ron has a video of you dressed and getting fucked while giving oral. By the way, great head you gave me. I will be seeing you again but for now, do not tell anyone what happens here tonight, or the video will be posted to the net wi0th your real name and home address. You will have horny men knocking on your door wanting to fuck a sweet cut and fucking your mouth.


With that, the three men left the room leaving me with the taste of cum in my mouth and cum dripping out of my ass, used and abused. I knew that in the days to come I was going to be used again but already thought how I can reverse my situation.