Cross dressed, fucked, and loving it!

I heard them knock at the door a few minutes after seven. I would normally just think showing up a few minutes after the scheduled time appropriate. However, knowing what I was getting myself into I was a wreck. Hoping they would show up a little early so I wouldn’t have to keep thinking about everything that may or may not happen. I was doing it though, I told myself, doing what I had been fantasizing about for years now. I am a twenty three year old male, about six feet tall, brown hair and green eyes, and for a while now I had been fantasizing about being dominated by a woman. I don’t know when I started fantasizing about this, but I found myself more and more looking at dominatrix porn, and reading dom stories. I particularly like the ones where the women dress a man up like a girl and start referring to the man as women. That really does it for me, when they will call the man a slut, and talk to each other like he isn’t even in the room. These stories inevitably lead to the women fucking the man with strapons and what not, or the women will bring the man out into public and find other men to fuck him. I wasn’t particularly into those parts of the story, but I still enjoyed reading them. I was a good looking guy, and didn’t have a problem getting laid, but I never met a women who could really turn me on like when I’m watching or reading dominatrix porn. I thought it would forever be a fantasy, then one night me and some buddies were out having a couple drinks, and we decided to go to the strip club. After being there for a couple of hours, we were all pretty far gone, and a girl came up to me asking if I wanted a private dance, I agreed. When we were in the back room I must have asked her to act out a dom seen, I can’t remember, but I know when I woke up the next day I found a card in my pants that the striper had given me that said, “Be ready next Saturday at 7:00 to really be treated like a girl, I’ll bring some friends”. She had kissed it too, as there was the obvious lipstick mark. I didn’t know if she had my address or not, but my mind was going crazy all week, and now here it was, Saturday night at seven and someone was at the door.
I opened the door to see two really attractive women, a blonde and a brunette, definitely C cups, and dressed to show them off. They must have been wearing four inch plus leather heels that went up to the knee, tight short skirts, and tops that didn’t leave much to the imagination. I was rock hard and they hadn’t even said anything yet. Both of them were carrying two huge suitcases, and when the blonde saw me look down at them she said, “Oh, were going to have so much fun tonight!” The brunette then spoke up, “Cindy he is cute, he looks a little nervous though! Is this your first time hun?” She asked me. I was still a little in disbelief at the whole situation and it took me a while to comprehend that I was just asked a question. I managed to spit out, “Well, not having sex.” They both started laughing hysterically, and the one name Cindy said, “This is going to be so much fun Ashley!” and they both walked past me into the apartment.
I followed Cindy and Ashley into my apartment, at least I got there names I thought. “So, would you ladies like a drink?” I asked. Ashley turned to face me and said, “Let’s get you ready first, then you can make us a drink.” She walked towards me while she was saying this and started essentially feeling me up. Touching my abs, arms, shoulders, then reached down between my legs and grabbed a hold of my rock hard cock from the outside and gave it a good squeeze. Her eyes flashed as she did this, holding a stare at me the whole time. “Were going to have to get this softened up before we dress him Cindy,” Ashley said, still staring at me. Cindy then walked up next to Ashley and cupped my chin in her hands and looked at Ashley, “He won’t be needing that tonight,” then looked at me, “well, maybe later, if you’re a good girl.” I nearly came in my pants right there and then when she said that, and I must have looked like it got me going to, because she said, “okay, get in the bathroom and calm yourself down. Ashley and myself need to get ourselves together and we’ll be in when we’re ready. You need to be completely naked when we come in, got that?” She was still holding my chin and nodded my head up and down for me, when I didn’t respond she pulled my head down a little rough and repeated herself, “Got that?” “Yes, yes.” I replied and she let go of my chin saying, “yes ma’am.” “Yes ma’am,” I responded, and I walked to the bathroom. Ashley gave me a spank on the ass as I walked away, I wasn’t expecting it so I jumped a little and Ashley said, “He’s going to be such a good little slut.”
I got naked in the bathroom as they told me to do, I could barely hear them out in the living room, I couldn’t make out any words, but they would laugh every so often. It was a little cool in the bathroom so it wasn’t hard for me to let my erection go down. I did have to think about something other than what just happened though, every time I did I could feel my cock begin to grow. My leg already had some dried pre-cum on it from earlier, I was a little embarrassed and hoped they wouldn’t notice. Time went by and I sat on the toilet, it was about 20 minutes before Cindy and Ashley came in. Any attempt I had earlier to get my erection down was instantly lost, they both had on red girders that let the tops of there breasts really pop, black frilly panties, heels that put them several inches taller than me, and the suitcases from before. “Stand up, stand up,” Ashley said, “and turn around.” I did as I was told, “What did we say about your dick bitch!?” Cindy said in an uppity tone. I didn’t say anything not thinking it was a question as much as a statement. Cindy repeated herself, “I asked you a question slut.” I answered, “You had asked me to calm myself down.” “Don’t be a wise ass bitch, now Ashley and I are going to set up the bathroom for your makeover, now let us know when your soft again.” I stood there with my back to them for several minutes, hearing them open the suitcases and pull things out, I didn’t dare speak, at least not until my erection was down. After a couple minutes of hard concentration I was soft again. “Okay, I’m ready,” I said. Without much warning, Cindy came up behind me and clasped this plastic thong looking thing on me. I looked down to see what she was doing, with my dick soft, the plastic thong compressed my dick and balls up into me, and lacing going around my legs held it firm. It was skin colored, and if you didn’t know any better, you would think you were looking down at a women’s pubic area. Cindy turned me around and looked down at me, cupping my head again, smiling, “How does that feel?” she ran her hand down my cheek, and then down my naked hairy chest, down to where my cock would be if it wasn’t being constrained by the chastity device. She started rubbing it, and I could feel my dick straining beneath it trying to get hard, but unable to in its restraint. “Feels good doesn’t it?” Her voice was soft and reassuring, “Knowing that your really just a little slut, a little girl who does what she’s told.” Cindy pulled a stool around, “Sit down little girl.” I sat down and looked over at all the items Ashley was still setting up. It essentially looked like a beauty parlor, shaving razors, blow dryer, wigs, nail color, everything a girl would use to look sexy. My heart was racing, the reality of the situation was setting in, and my dick was still straining in the plastic thong.
What followed was something every girl would probably love to have done; Cindy and Ashley were giving me a full blown make-over. They knelt down and pulled my legs up, Ashley begin working my toe nails, cutting them, polishing, and then grabbed a bottle of hot pink nail paint and started painting my toe nails. Cindy was covering my legs in shaving cream and began taking any and all hair off. The whole time the girls chatted about me like I wasn’t even really there. They commented on my body, how good I was going to look when they were done, how much fun the night was going to be. The whole time giving me gentle but assertive instruction when they needed to have me move or stand up to get to another part of my body. By the time the first phase was done I was completely hairless, even my head, and had hot pink nails. They told me to stand up and look in the mirror. I couldn’t believe what I looked like without all that hair, and I knew it wasn’t over yet. Ashley stood next to me and caressed my body and said, “She’s coming together Cindy.” Cindy just gave a sigh of agreement and began caressing me as well. The image of the much taller women caressing my body, with their gorgeous huge breast almost face level, and me only feeling the smooth absence of a cock between my legs, made me feel like a huge pussy. There dominance then was palpable.
The moment didn’t last long, Cindy snapped her fingers behind me, and I turned around to see her outstretched hand pointing toward the bathtub. “Get in,” she said assertively. I did as I was told and stood in the tub. Ashley gave two points with her finger to the floor, “on all fours girl!” Naked on all fours in the bathtub, I couldn’t see over the tubs edge, but I heard the girls pull something out of the bag and then the sound of running water in the sink. After about a minute or so on all fours, Ashley came up behind me and whispered, “Now just hold still okay little girl.” Anxious for what was going to happen, I felt Ashley slip a nozzle into my ass. The nozzle tip was rather small, but then I felt something warm in my anus. Oh shit! She’s giving me and enema! I had read about this in the dom stories. The women would do this to ensure the asshole was nice and clean before doing anything with it. I didn’t think they actually did it in real life! The pressure in my anus kept building and building until it was almost painful. Finally the bag of what I know knew to be warm water was empty. Before Ashley pulled the nozzle out though, she said I had to keep all the water in until they told me I could release it. After I agreed Ashley pulled the shower curtain closed. How long was this going to be!? Time seemed to stop as I waited and waited, Cindy and Ashley began chatting lightly about random topics. It felt like I was waiting so long, and the ease with which Cindy and Ashley were talking made me think they had forgotten about me in the tub, I was just about to release myself when the curtain flew open and Ashley told be to get on the toilet. I moved as fast as I could while keeping my asshole shut, once on the toilet I looked up at Ashley for permission to let myself go. Her eyes widened as she nodded, as if I was stupid for not knowing what to do. I let all the water come pouring out; it was such a relief when I was done. “Okay, back in the tub little girl!” My eyes shot up to meet hers, she read exactly what they were saying, and replied in a condescending tone, “Yes, you have to do this a few more times little girl, before your ready.” They gave me an enema two more times before it was finally over, by the end of the last one, to my surprise, the inside of my anus was stretched enough that it was not so painful, and I felt very clean on the inside.
Then there was a knock at the door, my heart leapt, who could it be? I made sure that no one would come by tonight, then Ashley said, “That must be our guests.” She gave me a wink and said to Cindy, “Do you think you can take her from here?” Cindy smiled and nodded as Ashley left the bathroom, shutting the door behind her. I strained to hear what was going on, it sounded like several people, women from what I could tell, had entered the apartment.
The rest of the make over Cindy said almost nothing, only swatting me with her hand now and then when I wasn’t moving fast enough, or getting in her way. Cindy pulled a pair of black panties out from a suitcase and slid them up my legs, they were a little tight, and with the plastic thong on completed the image of a female cunt, I can’t say I wasn’t impressed. I was oozing so much pre-cum that I swear it was going to start leaking out the side at some point. Then Cindy pulled out what looked to be a half-bra from the suitcase, fake tits. She picked up a bottle from the vanity and poured some of the solution into her hands. She then rubbed it on my chest, it was some sort of adhesive. She positioned the fake tits on my chest, and when they were where she wanted them, pressed them firmly up against me. The glue dried quick and Cindy was back in the suitcase again, as she was rummaging through the case, I reached up and felt my new fake breasts. They felt surprising real, and were holding up nicely. Cindy saw me feeling them and asked if I like my new breasts, I nodded. “Well enjoy it slut, because those are the only pair of tits your going to be feeling tonight,” and she began fitting a black frilly bra on me. Then she slid a pair of pantyhose on my freshly shaven legs. I have to admit these articles of clothing felt really nice on my body with the fresh shave. After the pantyhose she put a really short black skirt on me. It barely covered my ass, and it felt really weird knowing how exposed my body parts were. She also tightened a girder on me to help give me a more ‘feminine shape’. Cindy turned me around to put on a red see through blouse. When she did, the movement of my legs finally squeezed out some of all that pre-cum and I could feel the panties getting wet and smearing in between my thighs. I was really embarrassed and hoped Cindy wouldn’t find out. Cindy applied more of the glue to my bald head, and put on a very blonde wig, with hair going down to my shoulders. The last of the clothing was a pair of black high heels. I was only standing in them for a moment before Cindy sat me down again, but I could barely stand in them as it was. Back in the chair, Cindy began applying make up to my face, toning my eyelashes and putting lipstick on. When everything was said and done, Cindy leaned back with a big smile on her face and told me to stand up and look in the mirror. I was completely blown away by what I saw. I didn’t look like myself at all, if you had taken a picture of me and shown it to myself, I would have thought you were showing me a photo of a really attractive blonde, who was dressed like a raging slut and looking for some dick to suck. Cindy ran her fingers through my fake hair, “what a little slut you are! Wow, I keep getting better and better at this!” She then reached around and put a leather collar around my neck with a metal ring in the front. She pulled out the last remaining item from the suitcase, a leash that she attached to my neck, and to my horror, a camera which she quickly snapped a shot through the mirror of what appeared to be a slutty whore with a leash attached to her neck.
Cindy opened the door to the bathroom and said, “C’mon, let’s show you off to our guests!” My heart began racing again, I had know idea who was in my apartment, or what was going to happen to me. Cindy led me down the hall by the leash, and as she took the corner she stopped and said to whoever was in the room, “You ladies ready?” Several ‘yeses’ and giggles were heard from around the corner, and Cindy led me out into the living room by the leash. The room was full of six women, included Ashley who came with Cindy. All the women were half dressed in really sexy lingerie, and to my utter shock, they all had on nine inch strap on dildos. All the women exclaimed when I came around the corner, and began complementing Ashley and Cindy on the work they’d done. Several women said they wanted to see me up close, so Cindy led me to each women one by one by the leash. They all had there way with me. Feeling up under my skirt and pinching my ass, cupping my fake breasts, and to my utter embarrassment one of the women felt between my legs and her hands were instantly covered in my now pre cum drenched panties. She gasped as she pulled out her hand and all the women in the room began to giggle. “She’s so wet!” The women who had felt between my legs said. “What a little whore!” said Cindy and she pulled me down by the collar and said, “Don’t be impolite to your guests! Clean up her fingers!” Now up until this point in my life I had never eaten my own cum or pre cum, and the idea both shocked and aroused me. If I wasn’t so horny from all the evenings events I probably would have stopped the show right there, but I was so worked up and the lack of physical stimulus to my cock had my body aching for just about anything and everything. I opened my mouth and let the women slide her fingers in. She had a big smile and asked me if I like it, I simply nodded and heard all the other women start laughing and chatting amongst themselves. To my surprise the pre cum didn’t taste bad at all, it was pretty much flavorless with a slight salty taste. When I was done licking all my own pre cum Cindy pulled me to the next women, she didn’t waste any time and slid her hands between my legs and really got herself covered. I bent down to lick her fingers, but instead of putting her hand in my mouth she wiped her hand across my face. All the women in the room burst into laughter and one of the ladies said, “Joanna don’t be so mean to the little slut!” Cindy replied, “Please ladies, feel free to do what you want with her.” After the initial tour, Ashley said she would like those drinks I had offered earlier, and Cindy released me from my leash and said to me, “You are to bring every women here a glass of wine, and when you are finished you will let me put this leash back on you and you will kneel next to me. Understand slut?” I said yes ma’am and headed for the kitchen to get the drinks. It was tough walking in the heels, and it took me a long time to get all the drinks. The ladies commented on me the whole time, and would feel me up as I delivered their wine. I caught a glimpse of myself in a hallway mirror with the glass of wine, and if I wasn’t so afraid of what Cindy would do if I delayed to long, I would have stopped to check myself out. When I was finally done I went and kneeled next to Cindy and she put the leash back on me. The women then just chatted for a while, talking about sex, what positions they liked, all the while stroking there big strapons and shooting a wink over to me every now and then. After a while Ashley finally spoke up, “So who wants to pop our little sluts cherry?” My heart leapt, and the women named Joanna, who had wiped the now dry cum on my face, asked, “You mean she’s a virgin?” Ashley nodded and replied, “Yup, she’s going to be a tight one.” “I’m not a virgin slayer,” replied Joanna, “but I can get her worked up, come over here little girl.” Cindy stood up and said, “on your knees slut,” and led me over to Joanna. The short skirt rode up my ass being bent over, and one of the other ladies commented on my pretty black panties. The height of the chair that Joanna was sitting at put her fake cock right at face level. Cindy handed the leash off, and Joanna began running her fingers through my blond wig. I didn’t know if I was going to be able to handle all this, I certainly never sucked a cock before, and now I was expected to perform in a room full of women who were probably experts. “C’mon little girl, start by licking up my shaft and seeing how deep you can go,” I did as I was told, and licked up all nine inches of the strap on. The taste of rubber was evident, and when I got to the top I opened my mouth and took in about an inch of it. At about this time I heard the click of a camera somewhere behind me, and my heart sank at the thought of more photos being taken of me, especially in this position. I bobbed my head up and down a couple times, not really knowing what to do, but I started to pull what I had seen girls do to me and tried to duplicate it. I pulled out and stuck out my tongue and swirled it around the fake head a couple time before going back down. “Not bad,” commented Joanna, and I saw out the corner of my eye that some of the other women in the room were fingering themselves beneath their strap on dildos. I went down a little deeper onto Joanna, and after only a couple inches the dildo hit the back of my throat and I stopped. Joanna said I needed to relax a little. I went down again and tried, but couldn’t get the dildo any further than a few inches. Then, on my next time down, Joanna grabbed the back of my head and pushed my head down. At first, the dildo didn’t go any further and my throat was beginning to hurt as it was naturally trying to stop this intrusion. Finally, Joanna pushed a little harder coupled with a thrust from her hips and my throat couldn’t take it anymore. It relaxed for just a long enough moment for the dildo to work its way down, and Joanna pushed it all the way in. My face was right up against her body and I started gagging. One of the other ladies gasped, clearly impressed with this feat, and Joanna slowing let me come back up. The dildo was almost back to the initial couple inches I could handle, when Joanna thrust the fake cock back into my mouth. I tried going in rhythm, but she had total control, and started face fucking me hard and long. I hadn’t breathed since she started, and the lack of oxygen coupled with the jerking of my head was making me light headed. Drool was coming out of my mouth, only lubricating the dick even more, and the pitiful sounds of me trying to breath filled the room. Right when I didn’t think I could take anymore Joanna pulled me off her fake cock, I gasped a thankful breath, thinking I was done, before Joanna threw my face back into her cock and continued to face fuck me just as hard and fast as before. Again, when I felt like I was about to pass out, she pulled me off. This face fucking routine went on for several minutes, with the sound of multiple camera shots going off in the background, before Joanna finally relieved me.
I was starting to sweat, and before I regained composer my head was pulled back by the leash, “over here slut, Erica wants a turn.” Cindy led me over to Erica, who was sitting next to Ashley on the couch. Light headed with dried pre-cum on my face, the women Erica just pointed to her strap on and said, “get to work ho.” I didn’t loose any time, and with my throat loosened up from the first pass, I was able to deep throat Erica without being face fucked, the feeling of that full cock in my mouth felt so good! I couldn’t believe how much I was enjoying it. I could feel the ever growing pool of pre-cum continuing to spread between my thighs. I ended up sucking every women’s cock for the rest of the hour, I learned the last three women were Katie, Cheryl, and Veronica. Most of the women began wiping there dicks between my leg to get it covered in pre-cum before having me suck it off. By the time I was sucking the last women’s cock, Veronica, I was looking forward to taking a break, but Cindy had other plans. She tugged me off of Veronica and stood me up, gave me a firm open palmed slap on the ass and brought me to the center of the room. “Get on the coffee table on all fours bitch!” I did as instructed and was panting from the past hours activities. “She’s panting like the bitch she is,” said the women named Katie, all the women laughed. Ashley then got up from her chair, “put her head down between you hands whore.” Ashley said it as if she was giving some good advice, and I listened saying, “yes ma’am.” With my head between my hands, I felt Ashley pull my skirt up over my ass, and push the panties to the side. Then there was the cold dap of lubricant on my ass hole. It felt like eternity for the next moment to happen, Ashley gently slid her dildo between my thighs, toying it around my ass hole. Finally, I felt the pressure of the dildo trying to enter my ass. “Relax bitch! Relax,” said Ashley. Believe me, I was trying. She slowly worked her dildo into my ass. Reflexively I tipped my head up and moaned as she continued to push her cock up my ass. I stared into the face of all the other women and saw their grinning faces as they were all fingering themselves as they watched me get fucked. When Ashley was about half way in she started pulling out until the head of her cock was at my asshole, then she went back in, deeper. She continued this until all nine inches of the gorgeous cock was up my ass. It felt weird at first, but as my asshole loosened up it was feeling quite pleasurable. She slowly started pumping in and out of me, gaining speed. As the speed increased I could feel my fake tits swaying underneath me, despite the bra, and I was panting heavier and heavier as she continued. Eventually, she grabbed my hip with one hand and the leash with the other. She pulled my head up hard and with the other hand on my hips she really went to town fucking me. The sex organ inside the anus of both men and women was doing its job, I could feel by balls beginning to churn and I knew at some point I was going to cum in my panties. I can’t believe I’m about to cum by getting fucked by a woman! It was the best stimulus I had ever had. Cindy took a couple close ups as I was getting fucked, and then she put the camera down and moved in front of me. I was so exhausted from all the dick sucking and now getting fucked royally by Ashley that I just let my mouth hang open as Cindy shoved her cock into my mouth and began face fucking me. My dick was aching to explode with cum, and my ass cheeks began convulsing, my body trying anything to stimulate my constrained cock. Cindy and Ashley saw my convulsions and both got in sync and pumped all nine inches of fake cock into my mouth and ass at the same time, on the third full pump, I finally came like a rocket. I felt my dick explode two, three, four, five loads of cum and I could feel it dripping down my leg. Ashley didn’t skip a beat, she pulled her cock out of my ass and wiped my cum off my thighs with her dick and pulled me around with the leash, shoving her cum covered cock into my face. I was so high from the sex endorphins and exhaustion that I gladly sucked her dick clean. Unlike the pre cum, my cum had a unique texture and flavor, and moved around uniquely in my semen. I had to lick around Ashley’s cock several times to get it all, smearing it around my face in the process. “Hasn’t she turned into a wonderful slut!” Ashley exclaimed to Cindy, who nodded in agreement. While I was turned around, I could feel Cindy getting some more of my cum on here dick and she simply wiped it all over my face and fake cleavage. The night was far from over. The other women then took there turns fucking me, Joanna, Katie, Erica, Cheryl, and Veronica, someone always fucking me in the ass, the other fucking my face, all the while Cindy taking photos. I came three more times before the night was over, each time having to suck whoever’s dick had been fucking me clean. By the end my panties were completely soaked in my own cum, having spread all around my thighs and ass during the night of being fucked. My face wasn’t any better off; I had the constant smell of cum from around my nose, and the leftover taste in my mouth. To top it all I was drenched in sweat, and completely exhausted. I lay on the coffee table trying to recuperate as Cindy and Ashley saw the other ladies out, saying how they would have to do this again soon. The last thing I remember before passing out was Cindy taking another photo of me, and something sliding into my asshole again.
When I woke up the next morning my asshole killed, I could barely walk straight and the high heels weren’t helping anything. Cindy and Ashley were gone, along with all the makeup they had brought. I looked at myself in the mirror, I looked like a cheap whore with all the smeared makeup and cum dried on my face. I got undressed to take a shower, it took awhile, but the wig and tits came off surprisingly easily. My dick was glad to be out of the plastic thong. After the shower I dressed in regular men’s clothes and I put on a baseball cap to cover my now shaven head, when I walked back into the living room my friend Bill was sitting on the coach watching TV, he had something in his hand. “Hey Bill, what’s up?” Bill looked up at me, “Dude, this is fucking crazy, I can’t believe you paid to have this shit done!” My heart sank as I saw that he was looking through a photo album that contained all the pictures Cindy took last night. “I mean, this girl is hot! You must have paid a fortune, and where did all the other girls come from? Did you get a chance to tap that, or did you just have to watch and take photos all night?” I replied, “Umm, no I got in on it too…” I took the album from his hands and flipped through the pages, I had to give it to Cindy and Ashley, I looked good.

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