11 comments/ 66196 views/ 16 favorites Ray Finds Himself in a Skirt By: ReyLin64 At 18 I was not what you would call a manly man. I was 5' 5" and about 130lb long red hair, which I had let grow down to the middle of my back. I guess you could say I was a short skinny red haired hippy. I did not have a lot of friends and mostly smoked a lot of pot and watched TV. This drove my mother crazy. My dad had left us when I was about 3 and she had been trying her best to keep things together working 2 sometimes 3 jobs to put food on the table. Looking back now I can say I was a real shit. I did not make things easy on her at all. My mom and I look nothing alike; I am told I look a lot like my dad. My mom is about 5'9" and about 185 with dark hair and eyes. She has big tits and a little extra around the middle, but she is a very sexy looking woman. The only thing I get form my mom is my mouth we both have full lips. I have been teased quite a bit growing up that I have dick sucking lips. My life really changed just after my 18th birthday. My mom had come home from working a night shift and the house was a wreck, I had left dishes in the sink and had not done anything to clean up at all. When she walked in she flipped out at me. I was not in the mood for this shit, so I told her that I was not cleaning up the house that it was for a woman to do and I was a man, she could go fuck herself and stormed out of the house. I spent all day out just hanging out at the mall and getting high with Gary one of my few friends. It was not until around 7:00 when I got home. I walked in and the place was still trashed. It was even worse than I left it. My mom had ordered take out in it was all over the living room. I was just standing there not knowing what was going on when my mom walked in. She told me that things were going to change around here; she was not going to have any of this macho bull shit in this house. She said that we were going to start by getting me clean up. She literally grabbed me by the hair and dragged me to the shower. My clothes were off before I knew what was happening. I was standing there butt ass naked in front of my mother. I could feel my cock starting to get hard and was thinking oh please not now. Then my mom really blew my mind she striped out of her clothes and turned on the shower. All I could do was stair at her big beautiful tits. She had the biggest brown nipples I had ever seen. My dick was now so hard it was slapping against my stomach. She proceeded to throw me in to the shower wash me from head to toe. When she washed my cock she said it I came she would rip my little dick off. Then she shaved my legs, arms, under arms, cock and balls. My chest and face are smooth so that was no issue. After the shower she rubbed lotion all over me and again threatened me if I even thought about cumming. After I was clean, shaved and lotion down she pushed me down the hall to my room. Well it was my room when I left this morning. Now it was a barren room with a bed. All my stuff was gone. I mean all of it. My dresser was empty; walls cleaned there was nothing in my room. I was speechless; when I turned to my mother she said "say one word and I will slap the shit out of you"! Then she handed me a bag, inside there was some white lacy panties, matching bra, black skirt and a white blouse. Put them on she said! Ok, no! She slapped me so hard I was knocked on to my bed. When I got up I started to pull on the panties and bra. My mom stepped up to help but I thought she was going to hit me so I put my hands up. She said if I was a good girl she would never have to hit me. As my mother helped me get dressed she told me that I would be her little girl from now on. I would learn to cook, clean and everything that a good little girl should know. After I was dressed she took me to her room and did my makeup and hair. When she led me to her full length mirror I was shocked, I looked hot she had put small little pads in my bra and my legs looked so sexy. My lips where full, bright red, my hair was done in a cute pony tail and I loved it. I could not help that my cock was hard as a rock and pushing out against my skirt. My mother pushed me back down on to her bed and said that "this would just not do". I was afraid she was mad because my cock was hard, but she told me to relax and she pulled up my skirt and pulled my hard cock from my panties. As she kneeled in front of me she started licking the head of my cock then slid her wet juicy lips over the head. Now I have a small dick hard it is only about 4 inches long so she was easily able to take me all the way in to her mouth and flick her tongue against my balls. I going crazy I had never had sex in my life and here I was dressed like a girl and my mother was sucking my cock. I thought I was going to lose it right there. The next thing I knew I felt her finger pushing against my ass. She worked one than two fingers in to my young tight ass. It hurt a little but at the same time it felt incredible. She had hardly started to finger fuck me when I let go of my load. She contended fingering me as she milked my cock of every last drop of my cum. With her fingers still in my ass she kissed me deep pushing her tongue in to my mouth so I could taste my own cum. When I finely pulled myself together my mother told me to run along and start cleaning the house like a good girl. My head was still spinning as I walked out of her room to start my new job as her little girl maid. I could tell that life was going to be very different around the house, but I thought I just might like it. Ray Finds Himself in a Skirt Ch. 02 I was still in a bit of a fog I made my way into the completely trashed living room. As I looked around it was even worse than I remembered it. There where takeout boxes, dirty dishes, and random crap everywhere. I figured I had better get started before my mom came in and slapped the shit out of me again. That was something I could do without. So I started cleaning like my life depended on it. I would be mom's little house maid bitch if that would keep her from slapping me silly. As I worked around in the living room I could still feel were my mom's fingers had fucked my ass. Just thinking about this made my little cock hard again. I wended to stop and start jerking off right then and there, but I figured it really would piss mom off if she caught me. The fact that I was wearing an incredibly hot little maid outfit did not help much. I had never thought about dressing up like a girl, or maybe down deep I did; all I know is that it made me horny as hell. I really liked it; I loved the way I felt as I cleaned the house. I did not stop at the living room; I cleaned the house room by room. The only room I did not clean was my mother's room, there was no way I was going to disturb her. When I got to the bathroom I found my mom's gym bag. I was going to take out her gym cloths and wash them, but when I pulled out her still sweat soaked panties I could not believe how good they smelled. The mix of her sweat and pussy juice was like heaven. I took a deep smell and my hand immediately went to rubbing my rock hard cock through my silky little panties. I quickly put the rest of her cloths in the wash and made my way back to my room and closed the door. I lay on my back with one hand stroking my hard little dick and the other one pushing my mom's wet panties in to my face. As I stroked my cock I thought about earlier how my mother had sucked me off and finger fucked me at the same time. Just the thought was making me crazy. Rolling over I put my face in to her panties and slid one finger in my ass and jacked my dick for all I was worth. In no time I felt my nuts explode with load after load of my hot cum all over my bed. Existed I collapsed onto the bed my face still in my mom's panties and me in a puddle of my own cum. I awoke to a shock of pain across my bare ass. In utter shock I looked up to see my mother just as her second smack hit may ass. I tried to scramble away but she caught me by my pony tail, and held my head back down on to the mattress. "You little bitch, no one told you, you could jack you little dick off, and what the hell are you doing with my dirty nasty panties?" my mom said in a less than pleased tone. I tried to explain that I could not help it that her panties smelled so good and that I had gotten so hard it hurt. "You like the smell of my pussy you little sissy bitch?" she replied. "Yes mama" was all I could say. "Good, then lay back and clean me up. Let's see just how much you like the taste of it". Mom said. My mother then pushed me back down on to the bed and straddled my face. I promptly went to licking her sweet hot pussy. My tongue was all over the place, in and out of her slit then tracing around her big throbbing clit. I could tell I was doing a good job as she started grinding on my face. "Yes Reylin that's it baby lick momma's wet fuck hole. Lick my clit baby, don't stop make momma cum" She moaned. I could feel her legs shaking as she was rocking in my face, and then I felt a gush of her sweet tangy juice all over my face. I licked and sucked every drop I could. As she slumped forward I reach down to touch my cock, I was so fucking turned on that I felt like my balls would explode. Unfortunately my mother saw this and I felt her hand smack me across my cock and hand. "I never said that you could touch yourself! You will learn, that you are only allowed to cum when I say so. Do you understand me young lady". She said with a demanding voice Again all I could say was "Yes mama". With a satisfied look on her face, and a bit of a grin she said "Good, now roil over on all fours and stay that way until I get back". With that she left the room and I quickly got on all fours and waited for her return. Which was not long, she came in the door with what I thought looked like a strange dildo of some sort. Turns out it was a butt plug for yours truly. Mom slipped the butt plug in and out of her dripping wet pussy to lube it up, then without warning slid it in to my tight young ass. I groaned, but I really don't know if it was from pain, or pleasure. My dick was dripping precum like crazy, and I wanted so badly to cum, but I know mom would slap me if I even tried. "Now" my mom said. "Get up, and clean yourself up so we can go shopping. You did such a nice job on the house last night that momma wants to treat her little girl to some new cloths". Go out I thought, oh hell no. It was one thing to be dressed up like a sexy little girl at home, but to go out in public is a whole different ball game. I started to complain, then looked in to my mother's eyes and thought I had better not. So I got up and made my way to the shower. With every step I could feel the butt plug moving in my ass and precum dripping from my rock hard cock. I am not sure what to make of all that was happening; but I figured if I knew what was good for me, I would be the best little girl mom could imagine. Ray Finds Himself in a Skirt Ch. 03 Over the last few weeks Rey's life had changed drastically. After years of him being lazy and disrespectful Rey's mom had said enough! She had come home from work one night and found Rey as usual sitting on the couch doing nothing and the apartment was a mess. When his mom asked him to get up and start cleaning up, Ray had told her to go fuck herself he was not going to do woman's work and stormed out. When he returned home his mom had been waiting for him. She slapped him around and basically told Rey that from that point on he was going to be her little bitch, and if he was a good little girl things would go well for him. On the other hand if he did not do exactly what she said, she would slap the shit out of him. In the beginning Rey had been slapped around a few times. Rey's mom was not a small woman. At 5'9" 185 lb she was a full figured woman, she had nice D sized breasts, thick legs and ass, and a little extra in the middle. Rey on the other hand was 5'5" 130lb soaking wet. So mom had the upper hand so to speak. The drastic changes had come in the first few days. Rey's mom had literally striped everything out of his room and made him start over from scratch as a girl. She had thrown him in to the shower washed him, shaved his pubes, pits, chest and legs. If he even hinted at protest his mom would slap him right across the face. It did not take too many of those smacks to realize it was better to just play along. Before Rey knew what was going on he was fully decked out in a maid outfit and looking like a sexy little girl. The up side of all of this is that he had opened a whole new world for him. Before this started the highlight of Rey's sex life had been jacking off while looking at online porn. Now his mother had unlocked things in him he never knew he even liked. If Rey did as he was told and did everything his mom said, she would reword him with blow jobs that where mind blowing. While mom was sucking on his hard cock she would finger fuck the shit out of his ass. He had never thought he would like this, but now Rey so looked forward to feeling her fingers deep inside of him. Every day was a new sexual adventure with his mom. Rey was at her beckon call to lick, and suck her pussy on command. One of the down sides of this was that Rey was never allowed to jack off without his mother's permission. She made him keep a butt plug buried in his ass all day which gave him a constant hard on all day long. By the end of the day after doing all of his chores around the house Rey's cock would be soaking wet with pre cum. This made him all that more ready to please his mother in hopes of some sort of relief. The first time Rey was made to go out in public dressed as a girl he was freaking out, he just knew that someone would know that he was a guy, but the more he and his mother went out the easier it got. They had shopped for cloths; gotten their nails and hair done, and the entire time all he ever got was comments on what a beautiful young girl he was. His mom would only call him Reylin now and did everything she could to mold him in to her perfect little girl. As Rey reflected about the last few weeks he nervously put his last finishing touches on dinner. His mother had told him that she would be bringing home a friend from work for dinner, and that she wanted him to go all out. Rey had spent all morning cleaning the house and making sure it was spotless. He had really worked his magic with the roast chicken with lemon and garlic, mash potatoes, and fresh asparagus. He had no doubts that his mother would be pleased. Looking at the time Rey figured he had just enough time to shower, do his hair and makeup before mom and her guest got home. So he quickly showered, shaved all of his necessary parts; making sure that his cock and balls were smooth was something his mother demanded. After drying off and putting on lotion Rey picked up his butt plug and worked it back in to his tight little ass, then he slowly started to fuck himself with it to the point of almost no return. Just before he blew a load all over the bath room floor he stopped, knowing that somehow his mom would know that had shot his load without her permission. Leaving the bright pink butt plug deep in his ass Rey put on his new outfit that he and his mother had purchased for tonight, and then did his makeup and hair. When he was done Rey looked in to the full length mirror and knew he was absolutely hot as hell. He had on a very sexy green dress that fit tight in his waste and showed off his firm little ass. His long red hair was pulled up off his face and laying in curls down his back. Rey had done his make up to give him a smoky eyed look and had a deep plum lipstick on. His stockings and open toed black high heels topped it off. Well his new French manicure and pedicure made him down right sexy. It was getting hard to hide his swelling erection even though it was only a whopping 4 inches when it was hard. At 5:30 Rey's mom came through the door with her friend. I don't know what I was expecting, but I know this was not it. "ReyLin this is Josh my friend from work, Josh this is my daughter Raylin" mom said with a bit of a sheepish grin. Josh was a twenty something black man; just over 6 feet tall with a very athletic build. Now when I say black I don't mean your light skinned Will Smith black guy, we are talking like charcoal. Now don't get me wrong in no way am I prejudice at all, just I never in my life heard my mother said anything about a male friend no less a young black guy. I am sure I was looking a little stunned but did my best to pull it back together. "Very nice to meet you Josh" I said in my best feminine voice. Josh looked me up and down and said "nice to meet you Reylin" with a hungry smile, then looking at my mother Josh smiled and said" Cindy you are right, she is an absolute knock out." Smiling Rey's mom looked and him and said "yes she is, and a good cook to". A little confused and not sure what to say next Rey said "well I hope you are hungry becouse dinner is ready". Dinner went well, mostly small talk and comments on how good the food was. Rey felt a little bizarre as during dinner both Mom and Josh kept looking at him like he was the dessert. As the three finished up Rey told his mom that he would clean up and that her and Josh should go in the living room and talk while he took care of this. "Thank you baby that is nice" said his mom smiling at Josh. It did not take Rey long to clean up and have the kitchen back in tip top shape. He made his way to the bathroom to touch up his makeup and hair. Looking in the mirror Rey was pleased. Then he walked back down the hall to the living room to join his mom and Josh. For the second time today he found himself presented with a scene that he really did not expect. Both Josh and Rey's mom were sitting on the couch making out, kissing deep, tongues exploring each other mouth. Josh had his hand in mom shirt rubbing and squeezing her big tits. Rey could hear both of them moaning. If that was not enough his mom was stroking the biggest black cock Rey had ever seen. Ok in all fairness you could count on one hand the number of reel black cocks Rey had seen. This being said Joshes dick had to be nine inches long and thick, I mean real thick. Rey could see the shiny wet glaze of precum covering the head of that big fat black cock. As Rey stood there in a complete state of shock his mom looked over at him and said" Reylin come over here baby and show Josh how you can lick mommy's pussy." Still in shock Rey new better that to show any form of hesitation, so he quickly said "yes ma'am" walking over and kneeling in front of his mom. As Rey pushed up his mothers skirt he could see that she was not wearing any panties. While his mother leaned over to take Joshes big black cock in her moth, Rey began licking her already hot wet pussy. Rey could hear a combination of Josh moaning and the slurping of his mom going to town on joshes rock hard cock. Rey was licking, sucking and straight out tongue fucking his mother's sweet juicy pussy for all he was worth when she pushed his head back and told him to lie on his back. Rey quickly did as his mother told him. "Pull up your dress Reylin and show us that little cock of yours" his mother said. She still had Joshes big dick in her hand slowly stroking it up and down as she watched Rey lie on his back, pull up his tight green dress and pull down his already wet panties. Rey's little four inch cock was slapping his stomach it was so hard. His mom proceeded to get up off the couch, pull off her dress exposing her wonderfully full body and big tits, she than got on top of Rey in a 69 position rubbing her dripping wet pussy in his face. Again Ray went to town as the born pussy licker he was. He stopped in mid lick as his mother took his cock in to his mouth and started sucking and rolling her tongue around the head of his cock. After the initial shock he went back to work before his mother decided to stop sucking on his hard little cock. She lifted her head only long enough to say "fuck yes Reylin lick mommies Pussy that's it baby lick it good". The next thing Rey new he felt something pushing on his forehead. Taking a quick break from his mother's pussy Rey could see that Josh had positioned himself behind his mother, and was trying to work his big hard black cock in to her dripping wet pussy. Rey watched as inch by inch Josh slid his dick in to his mother. Josh reached down and pulled Rey's face back in to his mothers pussy. "Come on Reylin keep licking that pussy and my big black dick" said Josh with a rather demanding tone. Without much hesitation Rey went back to work sucking and licking his mother's pussy and now Joshes dick as it slid in and out of her. Rey could feel Joshes ball banging of his forehead as he started to pick up speed. Rey could feel his mother's legs shaking, as Josh now was fucking her like some kind of wild animal. Within seconds Rey felt his cock swell and he knew he was going to unload in to his mother's mouth as she sucked his cock with the same enthusiasm as Josh was putting in to her pussy. He let go and shot load after load of his hot cum in to her hungry mouth. She sucked and liked his cock around her grunting and groaning until she let loose with her own orgasm soaking Rey's face with her sweet juice. Rey did not think it was possible, but this just made Josh fuck even harder. "Fuck yes Cindy; I am going to cum in your fucking hot pussy OHHH fuck yesss" Josh said as he pounded Rey's mothers already dripping wet pussy. As Josh started to slow his strokes Rey went back to gently licking his mother's pussy. He was met by a deferent taste altogether, his mothers juices were now mixing with Joshes cum that was over flowing out of her over stuffed cunt. It was not a bad taste at all, not the sweat taste of his mother's pussy but in no way bad. Rey was again caught of guard as Josh finely pulled his big black cock out of his mother's pussy. Rey opened up his mouth to catch any of the mix of wonderful juice that may drip from his mother's wet pussy only to have Josh shove his cock half way down his throat. "Oh yea that feels nice suck and lick that big dick Reylin, you sexy little bitch". Josh said as he slowly slid his dick in and out of Reylin's mouth. After almost gagging on Joshes big black dick Rey really got in to it and tried to milk the last drops of cum out of the big thick dick. Eventually all three of them sat back and looked at each other; Rey sat there with a dazed look on his face still not sure what had happened. Cindy leaned over and gave Rey a deep kiss then licked a glob of Joshes cum that was running down the side of Rey's face. "Shit Raylin you are a mess, you need to get your ass in the shower and clean up". Rey's mother told him. "But first give Josh a kiss and tell him how much you enjoyed him coming over tonight." Rey slowly crawled over and kissed Josh, expecting a little peck on the lips. Apparently that was not what Josh had planned. Rey felt Joshes tongue slid in to his mouth and lock them in to an extremely passionate kiss. When Josh finely let go Rey just looked at him and in his small feminine voice said "it was very nice to meet you Josh I hope you enjoyed your visit tonight." Rey then got up and walked toward the bathroom, his dress was still hiked up; his little cock was hanging out, he had a 7 inch pink butt plug in his ass, and a mixture of some guy he just met and his moms cum all over his face. "Fuck could my life get any stranger" he thought. "I hope so" he said to himself as he walked down the hall with a smile on his face.