4 comments/ 459346 views/ 42 favorites Caught By My Sister By: popeyey2k I come from a pretty well off family. Dad is a successful lawyer and mom is a accountant for a big Fortune 500 company, and I grew up getting pretty much everything that I wanted. I've got a sister who is a little over 2 years older then I am and she too got about everything she wanted except a guy who knew which end was up. What I mean to say is that my sister Teresa usually picked the wrong men to fall in love with. At seventeen she ran off with a full time drunk that liked to slap her around. They got married , lived together for about a year then he beat her up real bad one night and home she came. After she got her divorce, she took up with guy that wasn't much better then the first husband, cept the fact that he was very bi-sexual, something that sis didn't know till coming home from work one day and catching him in bed with another man. The fact that they had my sisters frilly nightgowns on didn't make her very happy. She immediately started scream at him to get out and he hauled off and hit her, something that we never thought he would do. Just before this happened my mom and dad decided to go on a second honeymoon. Secure in the knowledge that Teresa was happily married(they thought) and me being 18, they let me stay home alone for the very first time. I had rented some x-rated movies and I was sitting in front of the TV watching some pretty heavy fucking and sucking when the doorbell rang. I shut the TV off and went to answer the door. I got to the front door and asked, "Who's There?" "Its Teresa, Dan" I opened the door and there stood my big sister holding 2 suitcases and sporting a major shiner. The first thing I asked her was, "Who gave ya the black eye?" She then told me about what she had walked in on and what had happened. I was very visibly angry and ready to go over and really let the guy have it when she quickly told me that he was already hurting pretty good. Seems that his gay lover didn't take to well to a guy hitting a girl and beat the shit out of him after he hit my sis. Now, my sister is a dream of any man that sees her. She stands about 5'7 and weighs about 125. She has a figure that most porn stars would love to have, without having to pay for it. She has blonde hair and green eyes. And the kind of lips that look like they were made for sucking cock. She quickly came in and asked, "Where's mom, I really need to talk to her." I told her that they had left early that morning for a second honeymoon and she started to cry. I quickly took her into my arms and asked her if there was anything that I could do to help and she explained that she really wanted to talk to mom. She then said she was tired so she was gonna go up to her old room and take a nap. I told her ok, and that I will be there for her anytime if she need me to. She gave me a big hug and told me that I was so sweet and gave me a quick kiss on the lips and went up the stairs for her little nap. I watched her ass all the way up, man, if she wasn't my sister I would be all over her. Her ass in them skin tight jeans was just about the nicest sight I had ever seen. So I went back to the living room and started to watch my movies again. An hour or so had gone by and I was watching a movie that had my favorite actress in it. I had slipped out of my clothes and was slowly stroking my cock while watching the film. It was in a part where a guy playing April Summers brother was giving it to her good doggy style, when all of a sudden I heard a gasp from behind me. I turned to see Teresa standing there in just a t-shirt and thong with a big surprised look on her face. "Dan, what are you doing and what is that you are watching on TV?" I quickly covered my cock with my t-shirt and tried to tell her, "Just a little self abuse sis, nothing to worry about." "I thought you were upstairs sleeping and didn't expect you to come back down till morning." Her attention was on the TV and listen to April tell her on screen brother to give to her harder. "Do Mom and Dad know you watch this stuff." she asked. "No way, you know how uptight they are when it comes to porn." I replied. "Yea, I forget that sometimes, what is the name of this one." she asked. "My Little Sister, Thats April Summers getting fucked by her big brother on screen." She then asked me why I had to watch this stuff, and said that I was a good looking guy and should have a girlfriend to be able to take care of my needs. I explained to her that my girlfriend was out of town for the weekend. She then really surprised me when she asked if she could see my cock again. I took the shirt away and let her have a good look. She gasped and asked me, "How big is that thing, neither of my husbands were that big." I told her proudly, "It is exactly 8 3/4 long and 3 inches around." She then asked if she could touch it and of course being all heated up I told her to have fun. She then got down on her knees and grabbed me with her left hand and started to stroke me, and used her right hand to massage my balls. I laid my head back and groaned cause it felt so good. Then all of a sudden I felt something warm and wet around my cock and looked down to see that my sister had started to suck my cock. She was teasing the head with just her tongue and looked up to see me smiling at her and said, "You like that, watch this." She then swallowed the whole thing all the way to the base. I groaned and thought damn, she needs to teach the girlfriend how to do that. She then kept taking me deep into her throat and then letting the whole thing except for the head out of her mouth then plunging the whole thing back down her throat. After about 30 seconds of this I yelled, "Teresa, if you don't want a mouthfull of cum ya better stop. She looked up at me and said, "Shoot your cum in my mouth, I want to swallow every drop you can give me." So, never to be one to turn down a lady I let my cock explode in her mouth and she swallowed every drop that I gave her. She sat back and looked at me and asked how I like that. My answer was to slip down on the floor next to her and to lay her down and slowly slide that sexy little thong off her body. I spread her legs so I could see her pretty little pussy and gasped. She just smiled and said, "That no good for nothing ex of mine asked me to do it so I did." There in the middle of her pussy, which was shaved bare was a gold ring. I just answered her by wrapping my mouth around that ring and sucking it deep into my mouth. Sis threw her had back and screamed, "Oh, god." "Dan, if you keep that up you better get ready to get a face full." Of course, I kept going while sliding a finger into her and finger fucking her while I sucked her little gold ring which just happen to be through her huge clit. She screamed out in orgasm and thats when I found out that my big sister was a squirter when she came. She must have squirted a gallon out of her and I couldn't keep up with it. After she came down she sat up and kissed me sticking her tongue deep into my mouth to taste her own juices that were left there. By now, my cock had gotten it second wind when she told me to fuck her like they were in the movie. Sis got on her knees in front of me and I slowly slid my cock deep into her tight pussy until my balls were resting against her ass. I thought, man she was right about me being bigger the both her ex's as she had the tightest pussy that I had ever been in. I was fucking her from behind when she notice that the movie had April riding her brother. She then told me she wanted to do that so I laid back on the floor and she sat on my cock with her back to my head. She then started to watch the movie and do what ever April was doing on screen. Now if you have ever seen April Summers in action, you know that I was getting the fucking of my life. Teresa was riding my cock like a women possessed. I didn't know how much more I could take when she all of sudden she spun around so she was facing me. She laid down and looked me in the eyes and told me that I had the best cock that she had ever felt inside her. I was touching her in places that no man had ever gone. She was riding me so hard that I thought she was gonna put me through the floor and into the basement. Then, all of a sudden she screamed she was cumming and her pussy started to tighten up on my cock. Then all of a sudden I felt her squirt all over my balls and that was my limit, I groaned and pushed my cock up into her as far as I could go and exploded deep inside her. After we were done she laid with her head on my chest and we were trying to catch my breathe when she told me we should have done this years ago. She then started to cry, I asked her," Sis whats wrong." She then looked me in the eye and said," Silly boy, its a happy cry, cause after all these years I finally got to be with the one man that I have always loved in the deepest way." This was a welcome surprise, as I have always love Teresa that way, just never ever dreamed of letting her know this, let alone making a move on her. I then told her, "Teresa, you have just made me a very happy man, and I will never leave you nor will I ever hit you." She then reached up and kissed me and told me she loved me. Then she looked at me and said, "My brother, my lover, take me to your bed and make love to me all night long." So I did, but thats another story. Caught By My Sister My little sister Sarah and I have always been close to each other, best mates as well as siblings and it only seemed natural that when she got a job near where I lived she moved in with me. We got along like a house on fire and confided in each other about everything and I was glad she was around when my girl friend dumped me. Then one evening things took a very unexpected turn. I'd never looked at my little sis' in a sexual way before that evening god only knows why though as she's a fit young brunette with slim hips long legs and a nice pert ass. The glow soon faded from her new job to be replaced by the dread and exhaustion I feel about my job these days. Sarah came home from work threw her suit jacket over the TV as I was watching it and slumped down on the sofa next to me "Hey just throw your stuff any old place!" I said grumpily. "I've had a hard day pay me attention." Sarah said in her most spoilt voice I sighed I knew she wouldn't go away unless I humoured her so I asked what was wrong. what followed was ten minutes of her yapping on about her boss, work mates, the size of her office, the severe lack of gratitude everyone had for the work she did etc,etc,etc.... I pretty much tuned out about there as her jacket slipped off the TV to reveal the porno I had been watching before my sister came in, I had muted it so she wouldn't hear it and as Sarah didn't usually come into the lounge so quickly when she came home I usually would of had time to eject the DVD and put it away but not this time though. Sarah's voice trailed off I thought she was about to go nuts but instead she began to laugh and needle me about it like she used to do when we were kids and I was caught doing something wrong by our parents "Danny's watching porno, he's not had it since he got dumped by his girlfriend nah, nah, nah, nah, nah …" This seemed to make her forget about her complaining at least. She began to pinch me and tickle me "What's the matter Danny need a good seeing to?" she asked as if talking to a baby. "Fuck off sis." I said my face turning bright red with embarrassment. Then the worst (or looking back maybe the best) thing that could have happened… well happened Sarah's eyes suddenly locked onto my crotch, she went into a stunned silence and her mouth opened wide. I followed her gaze down to where she was looking and could have died of embarrassment right there and then. Not only had my hard on from watching the porno not yet subsided but I had unzipped my jeans and forgotten to zip them up again before Sarah had come into the room, My little sister could see a bulge pushing my blue boxers out through the open zip Sarah brought her left hand up to cover her open mouth and I knew she would never let me live this down... ever. I quickly zipped myself up and put a cushion over my crotch. For the first time in her entire life Sarah was speechless and to me that made it worse than if she were teasing me about it. She just sat there staring at the cushion over my crotch then she began to giggle like a schoolgirl who had seen into the boys locker room "It's not funny Sarah, all men do it, and it's no big thing." I said. As the words came out of my mouth I knew I had said the wrong word. Sarah burst into hysterical laughter and to be honest I thought it was funny too so I laughed as well Sarah patted the cushion and said "Don't you listen to the nasty man I'm sure your big enough." She spoke as if talking to a pet "Christ Sarah it's not a dog" I said surprised. "So why were you petting it then?" She asked all smart aleck like. "Very funny sis... Say isn't it your turn to make dinner. I'll have that pizza I bought yesterday." I said changing the subject. Sarah rolled her eyes she was always trying to get me to eat more healthily "Fine I'll leave you and 'Rover' to play together." She said as she got up and left for the kitchen. I breathed a sigh of relief as I removed the cushion. Still noticing I was hard I wondered when I'd get a chance to relieve myself. (If I only knew the answer to that question then) Twenty minutes later we sat down at the kitchen table together me with my pizza and a beer, Sarah with her salad and glass of red wine. Under the table my erection was still raging in my jeans with no sign of going away it was the longest time it had ever been hard but with my sis there I couldn't exactly just pull it out and toss off over her salad ( salad dressing jokes here please). Sarah who was sitting opposite me was quietly munching away on her salad. She wore a tight fitting light blue skirt that went to about mid thigh level on her; yet wasn't too short so she could wear it to work and a white blouse, she was sitting in the fading sunlight so it shone through the thin material I could make out the white lacy bra she was wearing. My cock throbbed in my jeans at the sight. I looked away quickly ashamed at being aroused by my own little sister. I tried to take my mind off sex by annoying my Sarah. I cut a slice of my pizza and lifted it up from the plate with one hand and wafted the aroma at her with the other "Mmm real food Sarah, hot, yummy cheese pizza. Full of all those calories you're so desperately trying to avoid." I teased. She looked up from her meal as I waved the slice in front of her and I could tell she was tempted but would she bite I wondered? "Pizza sis, I know you like it. Just one slice, it won't hurt." "It won't work Danny I'm happy with my salad thank you very much." She said as she turned her attention back to her meal. I took a big over exaggerated bite from the slice and rubbed my stomach as I chewed and swallowed "Mmmmm Sarah this is great it's like manna from heaven." I kept on teasing. I could tell by her face her resolve was weakening so I waved my beer at her as well knowing she liked a drink too "Come on sis one little bite of the forbidden fruit." Sarah's resolve broke and she grabbed the beer and pizza slice from me before I could even react. She sat back in her chair and ate up the slice and washed it down with the beer "Fuck it I can always start the diet again tomorrow." She said. We shared the rest of the pizza and drank a couple of six packs of beer each as a bet to see who would give up first. I won as Sarah got up from the table and staggered back through to the lounge "I win" I shouted through to her. "I let you; now bring the bottle of wine I opened through." She replied. I was drunk I had to admit it because it took me five minutes to find the bottle and stagger through to the lounge "Glasses?" Sarah asked. "No I wear contacts." I replied which made me laugh. I slumped down on the sofa next to Sarah, handed her the bottle and watched her take a big drink. For some reason as she swallowed I imagined I was standing over her and the bottle was my cock, spurting my seed down her throat, by this time I was so drunk I couldn't really be bothered to stop my cock from springing to life again. Sarah passed me the bottle and I took a drink as she fumbled down the side of the sofa for the TV remote control "Time for my TV show to come on." She said. As intelligence goes my sis isn't the brightest spark when sober but drunk she's about as bright as a blackout and the silly cow somehow hit play on the DVD part of the remote instead of the channel she wanted to watch. Up came the image of a guy taking some blonde bimbo doggy style on the floor of a church of all places Sarah began to giggle "Oops silly me." She slurred Sarah was about to turn the DVD off when a wicked smile spread across her face "I know let's watch this instead" She slurred "What? It's a porno sis" I replied. "What's the matter Danny? Afraid Rover might mess your boxers?" She giggled as she eyed the bulge in my jeans. Great I thought now my little sister has a pet name for my cock that was all I needed. "Hey I've never cum early in my life before and never will." I told her trying to protect my male pride from her teasing. Sarah looked at the screen just as the man shot his load over the blonde's ass "Well that's a waste of cum. I mean if your gonna fuck a girl you might as well have the decency to spurt inside her." She said I was surprised and a little bit more aroused by her words I'd never heard Sarah talk like that "It's called a cum shot Sarah Your meant to see it, it's a turn on." I told her "Well I knew that." She said trying not to sound too naive. "You've never seen a porno?" I asked suddenly realising. My sister shook her head. A chance to corrupt an innocent I drunkenly thought. I took the remote from Sarah and unmuted the sound just in time for the next scene to start "Well sit back and watch sis." I said. Sarah did as I said and we watched together as the scene started started. It was set in a school classroom with a male teacher talking alone to a 'schoolgirl' who was obviously over eighteen the plot was the girl was behind on her studies and the teacher offered to give her 'tuition'. Soon the girl was on her knees sucking the mans long hard cock like a pro. Out of the corner of my eye I watched my sister as she shifted in her seat she was obviously turned on by this but sitting next to her brother made her a little uncomfortable so I handed her back the wine bottle and she began to drink it as she watched. Soon the 'schoolgirl was bent over a desk and the man was pushing up her pleated skirt and ripping off her panties "Please sir not too hard" Pleaded the girl but you knew she'd be ignored I looked back at Sarah, she was now rubbing a finger over her left nipple which still lay covered under the thin blouse and her bra, she licked her lips as the man entered the 'schoolgirl' from behind and began to fuck her hard. Inside my jeans my cock was straining at the material wanting to get out, I knew my sister could see the bulge so I put a hand over it as if to cover it up but really as an excuse to touch myself. As the porno progressed Sarah unbuttoned the top three buttons of her blouse and slipped a hand in and pulled out her left breast so she could tease her nipple with her fingers, I couldn't believe how turned on she was making me, I began to rub my crotch slowly to see if Sarah would object but she didn't so I turned my head to get a good look at what she was doing. Her earlier uncomfortable ness had obviously disappeared as she looked me in the eyes as she said "Let me play with rover now." Her right hand went to my crotch, unzipped my jeans and pulled out my rock hard cock "Ooo Danny you're so big." She said as she moved her fingers over my length. This was wrong we both knew that but at that moment we weren't going to stop for anything. We leaned toward each other and kissed passionately. Sarah was no beginner and was as good a kisser as any girlfriend I'd ever had but she soon broke it off as she had another idea in mind Sarah took off her blouse and led me back into the kitchen "I've always wanted to fuck in here." She said as she cleared the table with a swoop of her hand I bent my little sister over the table and began to kiss the back of her neck and shoulders "But I'll bet you never thought it would be your brother you'd fuck in here though huh?" She laughed and pushed her hips back making her ass rub against my cock, it felt so good. "Please sir not too hard" She said imitating the porn star on the DVD. I needed no further encouragement and pushed her tight skirt up over her ass revealing a white lacy g-string and her pert little ass, I ran a hand over it "Fuck sis you've been hiding this from me all this time?" I pulled her G-string off and Sarah spread her legs enough to reveal her shaved pussy and puckered asshole. I lifted one of her legs up onto the table and got down on my knees ready to lick my sister out, the smell of her quim was intoxicating I ran my tongue along the length of her pussy lips and flicked her clit with the tip which made Sarah quiver and purr with pleasure. The taboo taste of my sisters' pussy was like no other I'd ever tried maybe it was because she was my sister (or the beer I'd had) but she tasted like honey. I tongued her pussy for a few minutes until Sarah's whole body began to shake and quiver and she was moaning wildly with pleasure as she began to orgasm, I clamped my mouth over her hole and pushed my tongue as far inside her warm wet cunt as I could just in time for her to climax and flood my mouth with her sweet juices. Once her orgasm had subsided I stood back up and leaned over so we could kiss again, she lapped her tongue at her own juices that covered my lips. I took her bra off and turned her round, her breasts weren't too big or small but just the right size and her nipples were rock hard, I squeezed them between my fingers before sucking on them "Oh Danny that's so good, suck my tits." Sarah moaned. As I sucked on them Sarah undid the button on my jeans and pushed them and my boxers off my hips so she could slowly wank my ten inch cock and rub my balls "I want you in me" She whispered in my ear as she rubbed the tip of my cock along her pussy lips "I'll fuck you soon enough...." I teased "… Now get on your knees and suck my cock." Sarah got down on her knees and took my cock in her mouth, her warm wet lips glided effortlessly over my length until she felt the tip hit the back of her throat with inches still to go "Not such a big mouth after all then huh sis?" I teased But my sister was never one to turn down a challenge "I'll take it all Danny don't you worry." She said looking up at me with a devilish grin as she put my cock back in her mouth. She moved herself so she was sitting open legged on the floor and low enough for my length to go down her throat. Being deep throated by your younger sister for the first time is quite an experience the little minx was more experienced than she let on and was sucking my cock as if she were a porn star. Sarah would lick my entire length then take me all the way down her throat before slowly letting my length back out all the time playing with my balls with one hand while playing with her pussy with the other. All too soon I felt my cock about to explode but I desperately wanted to fuck my sister good and proper as afterwards this might never happen again so I got her up onto the edge of the kitchen table and opened her legs wide and took in the view of her bald cunt glistening with her juices. It was at this point that a little common sense entered my drunken brain "Should I get a rubber?" I asked her. "Don't bother I'm on the pill." She replied rubbing her pussy invitingly Without further delay I placed the tip of my cock at the entrance to her love hole and slowly eased into my little sister, we both moaned in unison at how good it felt. My sister was tight but wet enough to allow me to fill her to the hilt with little difficulty; I felt my balls rub against the skin between her cunt and asshole and took that as my cue to start fucking Sarah at a steady yet firm pace. Sarah lay back on the table rubbing her tits and moaning softly, as I began to speed up the pace I also began to rub my sisters clit which made her body begin to shake and her groans become louder "Fuck me Danny fuck your little sister." She urged. I didn't need any urging though I was soon fucking Sarah as hard and as fast as I could, my balls began to tighten as they slapped against her and I knew I was going to cum in minutes so I quickened the pace I was massaging her clit at and Sarah closed her legs around me. Soon enough we were both coming my cock twitched inside her as I shot spurt after spurt of cum into my sisters pussy and her cunt muscles clamped round my shaft as Sarah orgasmed. I collapsed on top of her gasping for breath from, my exertions and I could feel Sarah's chest heaving for air as well, my cock was now waning inside my sister but I didn't pull out, I wanted to be inside her a little while longer. Sarah put a hand on the back of my head and stroked my hair "Rover's well trained I see." We both began to laugh. It was then I knew this wouldn't be our only time together. Caught by my Sister It was 10 o'clock on a Friday night and I was all alone in the house. My Mom, Erica, who was in her late 30's and recently divorced was enjoying her new found freedom by going out with he girlfriends. My sister, Jane, was out with her friends for the night and that left me alone as usual. My name is Brian and I am an eighteen year old high school senior. I don't have a lot of friends so I often end up home alone on the weekends. I am 5'6 with short light brown hair and a medium build. Being a swimmer, I have a slim, toned physique and broad shoulders. This particular night was not unlike any other Friday for me. I waited until my mother and sister left for the night and then had my own fun. I'm not sure when it started, but I love dressing up in my sister's clothes. Don't get me wrong, I've always been attracted to girls but I love the soft silky material of her underwear pressed against my hard cock. When I am lucky enough to have a whole night with both of them out of the house, like tonight, I usually go all out in my sister's room. Tonight I chose my favorite pair of her silk panties. They are dark red with black lace trim. I love sliding them up my bare legs as I stand naked in front of her mirror. Since I am a swimmer I have been shaving what little body hair I have for years. Recently, I also started to shave my pubic hair so my balls are completely smooth. I couldn't believe how good her panties felt against my bare balls the first time I shaved. I almost erupted into her panties as I rubbed myself through the soft material the first time. I picked out a pair of black thigh high stockings and slowly slid them up each leg. Next I pulled out a pair of her high heels and slipped my feet into them. I liked to practice walking around in heels while wearing stockings. I liked the way that they made my legs look and also how the cool air felt as it flowed over my stocking clad legs. I was standing in the middle of her room when I heard the door knob turn. I froze, unsure of what to do. Jane walked into the room and stopped dead in her tracks when she saw me standing in her room dressed in her panties, stockings, and high heels. My hard cock was visibly straining against the soft panties when I noticed her staring at my crotch. "Brian! What the fuck are you doing?" "I'm so sorry, I thought you went out for the night." "So that makes this ok?" "No, I just didn't..." "I always knew you were a pervert, but this is insane! I come home to get ready for a party and I find my baby brother perving out in my panties." She stormed across the room and stood in front of her full length mirror. As she looked herself over I saw a wicked grin appear on her face. "Well, I can't go out looking like this and neither can you." She turned to me and said "Get out of here so I can get ready. I'll deal with you when I'm done." I was stunned and embarrassed standing there. I could barely think straight, and didn't have any reason to argue with her. I turned towards the door and started to leave her room. "And don't you dare think about changing!" I looked over my shoulder and looked at her as I left. It was hard to tell but she didn't seem as angry as I thought she would be. I walked down the hallway to my room and sat on my bed to wait for her. About a half hour later she appeared in my doorway. She looked stunning. Jane is a little shorter than me with a similar frame. She is athletic but very feminine. Her breasts are not very large but are very perky, she often goes out without wearing bra, and has shoulder length blond hair. Tonight she was wearing a tight white t-shirt that was thin enough to clearly show off her black lace bra underneath. Her skirt was short and loose around her hips with a hem that fell several inches above her knees. To finish off her outfit she wore a pair of tight black high heel boots that came up to her knees. I always felt guilty when I would check out my sister before she went out for the night. I knew that she was a slut, everyone in my high school knew that, and would take advantage of the fact that she always wore skimpy outfits around the house. "Come on, we don't have much time." She waved her hand at me indicating that I should follow her and led me back to her bedroom closing the door behind us. I noticed that she had laid an outfit out on her bed. "Since you like to dress up so much I thought it would be fun to show you off." What was she talking about? I've never even thought of leaving the house dressed in her clothes before. "What do you mean show me off?" "Well, since you never get out of the house I thought that you might want to come out and party with your big sister." "I don't know about this." "You don't have much of a choice. Either you do what I say or I'm telling everyone about you." Shit, she had me. "There's no way that this will work. If I go out wearing that everyone will know I'm not a girl." "Don't worry, I have it all worked out. Come over here and turn around." I felt her hands reaching around me and realized that she was putting a bra on me. After she snapped it into place I turned and looked into the mirror. "How is this going to help anything?" As I said that I saw that she was walking towards me with something in her hand. As she stuffed something into each cup of the bra she told me that she bought these inserts years ago because she was jealous of Becky Anderson's boobs. After she was done adjusting me I lifted my hands up and squeezed my new chest. I couldn't believe it. I had breasts! The bra that she chose for me was a black strapless padded bra that completely covered the inserts so that it actually looked like I had natural breasts. She pushed my arms up over my head and wrapped a black silk corset around my chest. I felt her struggling with the back and then she pulled it tight. All of the air was pushed out of my lungs as she tied it closed. She could tell that I was having a hard time breathing and said "Don't worry you look great. You'll be able to breathe just fine." Next she knelt down in front of me and looked up at me as she slid a loose skirt up my legs. I was lost in her eyes as her hands moved up my thighs to position the skirt. Her face gently pressed against my crotch as she reached around my waist and zipped me up. Before I knew it she was standing in front of me again. Her lips were inches away from mine as she stood there looking into my eyes. I was in a trance I was so hot right now. I felt her take my hand and pull me over to her bed and told me to sit. She pulled up a chair and started to apply makeup. After a few minutes she pulled out a set of fake nails and glued them on. After she finished with my nails, she reached out and put a small black necklace around my neck, she called it a choker and said that it should cover my adam's apple. She told me not to move as she sprayed a mist of perfume all over me. The final piece of my new outfit was a dark red wig. She spent a lot of time making sure that it was straight and I could feel her clipping it into my hair in several different places. "We don't want this coming off tonight, now do we?" She said as she gave me a sexy wink. She sat there admirering her handiwork when I heard a car honking outside. "Perfect timing. It's our ride. Come on Bria... How about Suzy. Come on Suzy, it's time to party!" Jane got up, grabbed her purse and headed for the door. I moved in front of the mirror and looked at myself in awe. I wasn't a shy teenage boy anymore. I was now a sexy woman. I couldn't believe how hot I looked. My cock was straining against my sister's panties. I heard another honk and ran down the stairs. It wasn't until I walked out of the front door that it finally hit me. I was about to go out to a party in drag. If anyone found out my life would be over. Jane's friend Amy was waiting in the driveway. They both looked anxious so I quickly locked up the house and hopped into the back seat of her car. "Amy, this is my cousin Suzy from out of town. She is staying with us for a little while and wanted to have some fun." "Hi Suzy. I love your outfit. You look very sexy!" I couldn't believe it. She actually thought I was a girl. I was about to open my mouth when I realized that my voice would be a dead giveaway. I cleared my throat and made my best attempt at a high pitched female voice. "Thanks, you look great too." Jane turned back and looked at me from the front seat with a big grin on her face. "Don't forget to pick up the boys Amy." "Don't worry, Jarred's house is on the way." As we drove across town I was starting to feel a little more comfortable in my new role and made a few brief attempts to join in the conversation to test out my new voice. We pulled up to a house and two guys came running out. One of them walked around the car and they each opened a door to enter. I didn't have much of a choice and slid to the middle seat as they both pushed themselves in flanking me on both sides. My sister turned around and introduced me to the boys. "Jarred, Alex this my cousin Suzy. She is staying with me for a little while. Oh yeah, and she's kind of a slut!" A big grin spread across her face as she said the last line and then turned around. The guy on my right side turned to me and said "Hi Suzy, my name is Jarred. You smell great." "Thanks." The guy on my left side held up his left hand and took my right hand in his. "My name is Alex. I love your outfit." He let go of my hand and his right hand moved onto my left leg. He gently caressed my thigh through the stockings as we drove away. My head was swimming. I was getting hard while another guy was touching me. Does this mean that I'm gay? Since the backseat didn't have a lot of room I ended up putting my left hand on top of his as he continued to caress me. I could feel Alex leaning into me and push my hair away from my neck. His warm breath against the nape of my neck made my whole body tingle with excitement. "Mmmmm, you really do smell nice." He moaned into my neck as his hand slid a little further up my thigh. I squeezed his hand nervously as I felt his wet lips pressing against my skin. My head rocked back and I let out a little moan. The car came to a stop on a quite street lined with dozens of other cars and Amy said "We're here!" All of a sudden the doors flung open and everyone poured out of the car. Alex still held my hand in his as we walked up to the house. My sister came in close to me and whispered into my ear. "It looks like you were enjoying yourself back there. Just be careful, you can only go so far. We don't want anyone to find our your little secret do we. Have fun tonight!" She gave me a peck on the cheek and grabbed my ass through the skirt before breaking off to catch up with Amy. I was thankful that I had spent so much time practicing walking in heels, but I was still having a hard time keeping up with everyone else as we walked up the long driveway. The party was in the "rich" part of town and the house was gigantic. It took us nearly five minutes just to walk up the driveway. As we approached the house I could hear loud music mixed with laughter pouring out of the open windows. Thankfully, I didn't recognize most of the people at the party as we worked our way inside. The lights were dim and most of the people were dancing in the front room. Jane and Amy led us right to the kitchen where the drinks were. Amy poured a round of shots while my sister mixed up drinks and passed them out to our group. Everyone held up their shots and drank them together. I've never really drank before so I followed their lead. The shot burned my throat but I noticed everyone else drinking their mixed drink after the shot. I again followed their lead and found that the sweet drink helped wash the shot down. "Let's do another one!" Alex shouted as he slipped his hand around my waist and pulled me into him. I was starting to feel a little warm after the second shot. Alex again slipped his strong arm around me and pulled me towards him. I held my drink in one hand and wrapped my other arm around his waist. He held me against his tight stomach as he leaned in and kissed me. I was surprised at how good it felt when his lips pressed against mine. I let my head fall back and my mouth open as his tongue worked its way into me. This was my first kiss and I had no idea what I was doing. His tongue swirled around inside of my mouth and I desperately tried to think of what I should do. I dropped my drink and brought my hand up to his neck. His skin felt warm and soft as we kissed. His hands reached around me and slid up my thighs under my skirt. He massaged my ass through my sister's panties while he ground his crotch into mine. Alex broke away from our kiss and pulled away from me. My skin felt cold as he took his hands away. He grabbed my hand and pulled me into the next room. The lights were all off and people were dancing all around us. He led me to the far corner and sat down in a chair pulling me between his legs. His hands against explored my legs and thighs, but I knew where he was going next. I could only think of one way out. I lowered myself to my knees and crawled up to him. He looked down at me a with a knowing grin and started to unbuckled his pants. He lifted his ass up enough to slid his jeans and underwear down to the floor. In an instant I was staring at his rock hard cock inches from my face. Up until now, my only experience with a cock was my own. I had never even thought of another man in this way before, but sitting here dressed up like a slut in my sister's clothes made me feel so sexy and feminine. I started out slow and let my hands rub his thighs. He felt warm to my touch and his skin was soft. I pushed his thighs apart and slowly inched myself closer to him. My hands moved up his thighs until I reached his cock. I slowly wrapped my hands around his balls and gently played with them as his cock stared at me waiting for me to take it. My right hand cautiously moved to the base of his hard cock and I wrapped my fingers around him. I could feel his shaft twitch to the rhythm of his pulse as my hand slid up his cock. I was amazed at how soft the skin was when my hand finally wrapped around him. I gave him a gentle squeeze as my left hand continued fondling his balls. I felt his hands behind my head pulling me into him. The tip of his cock was getting closer and closer. I closed my eyes and opened my mouth. The tip of his cock pressed against my lower lip as he guided me onto him. I opened my mouth wider and felt his hot flesh slide into my waiting mouth. My tongue slid along the bottom half of his cock as I continued to lower my face onto him. I closed my lips around him when I felt the tip of his cock brushing against the back of my throat. I moved my hands to either side of the base of his cock to balance myself and started to suck. I didn't know what I was doing but it felt good to me. I hoped that it felt good to him too. I moved my mouth around as I sucked him and then slowly pulled my head back up the length of his cock. I stopped with the tip of his dick resting on my tongue and swirled it around him. I could taste his salty pre-cum dripping onto my tongue and found the courage to continue. I slowly worked my mouth back down the length of his cock while I slid my tongue around as best as I could. I kept this up for a few minutes until I could feel him pushing his hips into me as his cock filled my mouth. My nose was pressed against his pubic hair when I felt his cock twitch and fill my mouth with his hot sticky cum. I swallowed as much as I could as it flowed into me stream after stream. I could feel it dripping down my chin as his cock slowly started to shrink in my mouth. I pulled my mouth off of him and collapsed into his lap. "There you are, I've been looking all over for you!" I looked up and saw my sister standing over me with a devilish grin. "Come on Suzy. I've got a friend I want you to meet." She pulled me up and led me out of the dark room. I followed her upstairs into a dimly lit bedroom. There was a tall guy standing in the corner. "Matt, this is my cousin Suzy. Suzy, this is Matt, don't worry I've already told him all about you." Matt moved over to me and took my face in his hands and pulled my mouth to his. Our tongues met as he passionately kissed me. His hands slid down my body and then moved back up my thighs pushing my skirt up. I loved that everyone wanted to rub my ass so much. I felt so sexy in his arms. "Suzy, Matt here has never has had sex before and I told him that you would love to help him out." My sister pulled me away from him and pushed me towards the bed. She turned me around and pushed my forward, bending me over onto the bed. I felt her pulling the back of the panties to the side as she rubbed something cold onto me. Before I knew it I felt her slip a finger into my asshole. I pushed my legs further apart and let out a soft moan, pushing my hips into her hand. She pulled her finger out of me and it was replaced by something much warmer. I felt it pushing into me and realized that it must be his cock. In the dim light he must not realize that he was about to fuck my ass. I was so excited waiting for him to enter me. He slowly pushed the head of his cock against my asshole teasing me. My whole body tensed up as he finally thrust his cock inside of me. My knees were shaking as his hard cock pushed further into me. His hands held my hips and pulled me towards him as he slowly developed a rhythm with his thrusts. I looked up and saw my sister positioning herself in front of my face with her legs spread wide apart. She pulled her skirt up around her waist as she slide her pussy under my face. I could smell her musty odor as she pushed my head down to her shaved pussy. My tongue reached out and licked her as Matt slammed his cock into my ass. My moan was muffled by her dripping pussy. I lapped at her pussy like a madman. She tasted so sweet as her juices mixed with Alex's cum in mouth. I moved my tongue back and forth until it slipped inside of her. I could hear her moaning as I pushed deeper into my sister's tight pussy. I could feel her clit rubbing against my tongue as I worked it in and out of her. Her thighs clamped down around my head as she came. Her sweet juices dripped out of her pussy as I tried to lick up every drop. Matt kept pounding my ass as my sister lay exhausted in front of me. Matt kept pumping his throbbing cock deep into my ass as I noticed my sister reaching her hand down to grab my cock. My penis was aching to be freed but she just rubbed me through her panties while Matt fucked my ass. Her hand moved up and down the length of my cock faster and faster when he pulled my hips into him. He buried his cock deep inside of me and I knew what was coming. His cock twitched and swelled up inside of my ass. His hot cum shot deep into me, filling me up from the inside. The sensation of his cum filling me up while my sister stroked my cock through her silk panties pushed me over the edge. I felt my cock exploding into her panties as Matt continued to shoot his cum into me. He shot three large bursts of cum into me before finally pulling out. "Wow, you were right Jane. Your cousin is a great fuck." I heard a zipper and then a door close. "You did good tonight Suzy, but it's getting late. I called a cab for us, it should be here by now." Without missing a beat she got up and fixed her skirt. I followed her down stairs and out of the front door to the waiting cab. We both hopped in and the cab took off. She didn't say a word to me as we walked into the house. Before we even made it up the stairs the front door opened again and our mom walked in. Caught by my Sister She was clearly drunk but I was again gripped with the fear of being caught. Luckily Jane is a quick thinker and introduced me as one of her college friends who would be staying over for a few day while my apartment was being fumigated. "No problem. Any friend of Jane's is a friend of mine." Her speech was noticeably slurred as she said that. My mom was wearing an off white silk button down blouse with the top several buttons undone. She was also wearing a short skirt that barely covered her ass. I could tell that she was looking to have some fun dressed like that. My mom walked past us and gave Jane a quick kiss on the lips and then moved over to me and did the same. I have never had any sexual thoughts about my mother, but after the night I just had everything was fair game. My mother said she was going to make herself a drink an asked if we wanted one too. Jane said that she was tired and needed to go to bed. But I hesitate for just long enough for my drunk mom to say "That's ok, Suzy and I can have fun without you." With that my sister turned on her heels and said "Don't stay up too late ladies." My mom had already disappeared into the kitchen and returned with our drinks. She handed me one and plopped down on the couch. I took a sip and realized that it was just straight vodka. I looked over at my mom and saw that she had already downed most of hers. I moved over to the couch and saw that her head was slouching over and she was spilling her drink onto the couch. I put my glass down and took her hand to steady it. I could tell that she was out cold. I took her glass and put it down on the table and wondered what I should do. As I looked down at her I saw that her blouse was open enough for me to see the swell of her breasts. I could see that she wasn't wearing a bra. Her hard nipples were clearly visible through the thin material of her blouse. I reached down and gave her shoulder a little nudge to see if she would respond. Her head rolled a little further to the side but there was no other reaction. I lifted her head up from under her chin and her mouth gaped open as she sat there completely passed out. I let go of her chin and her head flopped back down. Feeling bolder I reached down and put my hand on her breast. She still didn't respond so I squeezed her and pinched her nipple through her blouse. At this point I realized that she was wasted. I reached out and unbuttoned two more buttons on her blouse and revealed her sexy breasts. I knelt down between her legs and moved my mouth over to her left nipple. My tongue flicked at it and made circles around it, which elicited a soft moan from my mother but nothing else. I saw that her skirt was already riding up her thighs and pushed it the rest of the way up. I can't believe my own mom isn't wearing any panties. Her light blond hair was matted down in tight curls around her pussy lips. I could smell her scent and was already getting hard again. I reached out with my finger and traced a line across her soft pussy lips. I heard another soft moan and nervously looked up to see her head was still flopped over to the side with her mouth wide open. Feeling more comfortable I pushed my finger into her pussy and felt how wet she was. I pulled my finger out and brought it to my mouth to taste her. She tasted sweet and salty, a mix that seemed familiar. I pushed her legs further apart and lowered my head to her crotch. My tongue brushed against her pussy pressing against her soft curls. I opened my mouth and began licking her. As my tongue pushed her lips apart I felt something dripping out of her. I looked down and saw what looked like cum dripping out of her pussy. I tasted it and realized that my mom had already been fucked tonight. I suddenly got an idea. I continued licking the strange cum from her pussy as her soft moans slowly increased. I buried my tongue into her pussy as I pressed my thumb against her clit. I felt her body tensing under me as she came. Her breathing was heavy but she still didn't make any moves. By now my cock was rock hard again and I needed some release. I remembered that one of the big fights between my parents was that my father wanted more kids but my mom didn't. She ended up having a procedure so that she couldn't, he never forgave her. I reached down and pushed my cum soaked panties to the side freeing my cock. I lifted myself up and positioned my cock right in front her waiting pussy. Slowly I pushed against her lips and felt my cock sliding into my mothers dripping pussy. Her exposed tits were shaking back and forth as I fucked her on the family couch. I felt my cock expanding inside of her as I came. I pulled my soft cock out of her and re-buttoned her blouse before heading back upstairs. After I got up to my room I saw that my sister had laid out one of her silk nighties and a fresh pair of panties for me to sleep in. I stripped my clothes off and slipped into my sister's nightie. I collapsed into my bed and passed right out.