7 comments/ 107603 views/ 16 favorites Dressing for My Sister Ch. 01 By: monika333 This is a large jump in the "Mark's sister" series, but couldn't wait to write! All of these stories are true with different names and we were both over the age of 18 when it all happened. My sister Lisa was a very beautiful girl! As we grew up we had shared some moments together, and at now 21 years old, and Lisa at 23 we had very active sexual lives! But something was about to happen, nothing anyone could have imagined! Lisa loved wearing fancy, sexy lingerie! She was always dressed up when she went out to the clubs, and she always looked beautiful! She had large firm breast's. She had a d cup in size, and a thin waist. She was very athletic so her legs were very strong and firm! She had shoulder length strawberry blonde hair, and a wicked beautiful smile. I was so attracted to her, and she had to know it! When my parents left the house and she would go out, I would go to her room and look through her pantie drawer. All her pretty panties and bra's!I kind of had a fetish, I would put them on and look at myself in the mirror, trying to look sexy. I am 5'9, 155 pounds; skinny, but toned! I looked very good in her clothes. She also had very sexy dresses. Long black licra dresses that cling to all of body. She had garter's and stockings, it was just the best time dressing up in her things. One day I heard my sister yelling. I think she was started to catch on. She noticed that her underwear drawer was all messed up, and that some of her panties were stained. I didn't know what to do. So I stopped dressing in her clothes. Man I didn't want to do that, but if anyone found out..... I would die! 6 months went by, and I was really getting the urge! I was so horny and wanting to dress. Everyone was gone one night, and my sister was going to stay over at a friends house after the club. First I had a long bath, shaved my legs, and my cock. Right down to the skin.Then I went to her room and was ready for action! I had time to dress, get off, and wash her clothes! As I was digging around I found some new items of clothing.... A red lace thong and matching bra. She had 4 new pairs of stockings in the package... should I dare open one up? Of course I would, I couldn't help it! I was so aroused by the thought. A matching red garter to the bra and panty set... wow, I couldn't believe the score! A nd with a little bit more digging, I found a new toy. She had a dildo, and I had never seen it before. Right beside the toy was some lubricant, and a book on masterbation. I was swimming! What should I do with this? Should I try it? I was really not sure, so I left it in there. I looked in her closet and she had a stunning long black stretchy dress with a high cut on the side. I was ready to go, and it was only 10 pm, lots of time to have my fun! My parents shouldn't be home to at least 3 am. I went downstairs and put on my favorite movie. Beautiful girls with toys. I lay my clothes on the floor. First thing I put on was the garter. It was lace with a little satin in-lay. I did up the clasp in the front and spun it around, mmm the feeling was out of this world! I open the pack of new stocking's. They were black with a lace top to match the outfit. I pulled the into my fingers; bunched up , so I could roll them up my leg. I put my toes in and slowly pulled them up my clean shaven legs. Wow what a feeling! I fasten the clasps on the garter and then clid the red lace thong pantie over my freshly shave cock. This was heaven! I slid the dress over my head and felt ready.... I look in the mirror, and mmmmm fabulous! I sat down, watched my movie, and enjoyed a couple of glasses of red wine. As the movie went on, I grew larger and larger. The wine went down faster and faster.... I think It's time! But as I was rubbing my cock threw my slippery dress and lace panties, My sister's new toy was up in my head. After all, the girls on the movie were enjoying there toys. I started to imagine my sister Lisa using that toy, and man was I liking that thought! After a good 10 minuets of dreaming this fantasy I took a little detour back to my sister's room. I went back in her drawer and moved her underwear aside and stared at that beautiful dildo. It was about 8 inches long and 1"1/2 thick. Not too big, but big enough. I picked it up and noticed it was obviously used. It had her dried juices all over the long pale tool. I was so high on the thought of this big toy being inside her.... if she can only see me now. All dressed up with her dildo in my hand. I looked at the toy, then smelt it. She had a clean pussy, it was a beautiful smell. I put my mouth over the cock shaped toy and began to slowly lap all the dry pussy juices my sister had all over it. MMM She taste so good! I wanted more! I licked and sucked the whole toy dry tasting all of my sister's love juice! I went down stairs. I just had to try this thing out. If not to see if it felt good, but to just know tht I am fucking myself with the same toy she uses! First I use the lubricant. I put a little on my middle finger and insert it in my ass. I keep the process going until it feel slippery... but I have to tell you, I don't know if I am going to like this. It kind of burns. Just when I feel like I am ready, I go to put the toy in. At first it won't go. It's sliding out, it's just so big for my virgin ass. After a few minuets........ WOW! Here she goes! That beautiful cock went in like a glove! And was I ever wrong... it felt amazing! It was the best feeling I had ever felt, and knowing this was my sister's toy cock made this fucking ever so sweet! In and out I fuck myself, pulling up my dress and feeling my ever so hard cock through my lace panties. My cock head seeping clear cum as I go.... so much leakage I just had to indulge! I kept tasting myself and fucking myself.... faster and faster! MMM This cock feels so good! And just as I am about to cum. "What the fuck do you think you are doing you weird fucker!" Busted! It was my sister Lisa. She was not supposed to be home till tomorrow, and now here I am dressed up in here clothes getting off on her dildo. I am so fucked! "Answer me you little weirdo! What the fuck are you doing? Why are you wearing my clothes? What are you gay?" I was mortified! I didn't know what to do? "I don't know" I cried. "I was just curious, I'm not gay I was just curious...." I was done! I have nothing, no excuse, no reason..... I am now scared of what she is to do to me? "Just leave me alone! I will fix this I promise!" I am in tears now, and at this point she starts to calm down a bit. I think she sees that I am truly sorry. "Just wait Mark. Don't worry, I just don't understand why you are doing this to yourself? It's weird! Just plain weird! I don't know any guy that would ever do this? What is the matter with you?" I really had no answer for her, at least not a good one."I just love your clothes. I wanted to see how they felt? I mean, you wear these sexy clothes for a reason? So why can't I?" "I am a women. I am supposed to look sexy and feel sexy! Guys look and feel sexy in other ways.... this is just not right!" Now I know I am screwed. I stand up and the dildo fell to the ground. I go to pick it up and as I grabbed it Lisa grabbed it too. I was stunned! I look up at her and she said "So what exactly made you want to use this?" I felt a lump grow in my throat. "I don't know, I seen it in your panty drawer and I was just curious?" "Did you clean it? I have used this thing you know. "At this point I didn't know what to say. I couldn't tell her I cleaned it with my mouth! How I licked all of her dried pussy juice off the whole thing. "Yes of course I cleaned it! I washed it with soap in the bathroom." "I bet you did." she looked at me like I was full of shit. What does she know? "Can I get dressed now? You are making me feel very uncomfortable. I am so sorry I have done this! It won't happen again." Just then, this evening would take a turn. I don't know what happened but she stood up and...."get up!" I then stood. "Let me smell your breath!" "My breath? Why?" I was starting to feel uneasy about all of this. "I smell wine. That is obvious." and then she moved in slowly, closed her eyes and took a long deep inhale."I smell my pussy!" Wow was I in shock! How did she know? "Don't try to lie my little brother! I know you sucked all of my juices off that toy. I saw you! I have watched the whole thing you little perve!" My heart dropped to the floor. What next, my friends walk in and see? What was she up too? "I have to admit little brother, you look very pretty in my things. I don't know what made you want to wear my clothes, but you wear them well. And for my toy. What will we do with you? You seemed to have enjoyed it. Did you?" I was lost for words! Was she coming on to me? "Did you? Tell me how much you enjoyed it!" "I really enjoyed it. It hurt at first but then it started to feel nice."She looked at me with a wicked smile."Well then lay down sweet brother. Let your big sister finish the job for you. I was speechless! I lay down on my back. I look at her, and she kneeled down on the floor. She opened my legs and from my left knee to my inner thigh, she racked her long red painted finger nails firmly up my stocking covered leg. "Wow you are very sexy." she said in a deep sexy tone."You have nicer legs than me." I was so aroused by what she was saying to me. I kept staring at my sister woundering what was to come next. "Let me help you." She moved my panties to the side, and started to rub my already loose asshole."MMM Looks like you are all ready aren't you?" I looked at her and she smiled. I couldn't believe my own sister was just about to fuck me with her love toy! She slowly slid the toy in and I gasp. Looking up at the ceiling with my eyes closed for a second. I was in heaven! Lisa slowly worked the toy back into me growing faster in speed, turning the cock shaped toy in half circles up and down twisting and stroking.....mmmm I was almost going to cum without any touching of my so very hard cock! And just as I was about to cum...... Lisa pulled the toy out, and put in in my mouth."Here you go you little perve! You suck my juices its time to suck yours!" I didn't hesitate. I let her put the worked over toy in my mouth, tasted all of my ass juices.... and I even enjoyed it? She put it back in my ass."That is a good little boy. You like tasting your ass?" I looked at her; my eyes glazed, almost confused I was so much in enjoyment! "Yes Lisa! MMM It taste sooo good!" She pulled it out again and then she started to slowly suck it, staring at me. Gazing deep into my eyes, sucking that cock deep and hard. Getting all of my ass taste off that big rubber cock! "MMMM I like the taste too! Have you had enough? Or do I get a turn?" I couldn't believe my ears? She wants to have fun too? Lisa was wearing a white satin blouse and a pair of tight black dress pants with pin strips. She looked sexy as all hell. She stood up in front of me and undid her front button. Her pants had a wrap around to the side with a zipper. She unzipped her pants, looked at me and slid them down. She had a small black satin thong on and from how close she was standing I could see, and smell the wetness all over her pretty panties. She stood on the edge of the couch above me, and right in front of my face she pulls aside her underwear and slowly inserts the toy inside her. "AHHHH!" she moaned. Staring into each other's eyes she began to get hard and nasty with her rubber cock! Deep and hard... stroking it in and out fast and furious! She was screaming..."Ahhh Fuck! Watch me you sissy bitch watch your sister cum!" I put my hands down my panties and began to finger my ass. I put 3 fingers in and fucked my self at the same pace as my sister. She pulls out the dildo, sucks on her pussy juice.... puts it back in, takes it out and feeds that cock to me so I can taste her again! She did this for a while as I continued to finger my ass! This was unbelieveable! I was soooo close to cummin! Just then she puts her hand above me against the wall, screaming and yelling..."Fuck Mark! MMM YES FUCK YES LOOK AT ME YOU SISSY WHORE!" And then she came! She was sooooo fuckin wet she came all over me. I have never seen this from a girl before? There was as much cum as I would cum? "Now your turn" she said."I am going to make you cum so hard little brother.... mmmm your sister wants! And she wants her little girly brother bad!" She put the pussy filled toy back into my already fucked ass. She was taking no time giving me a good fucking. She went closer to my cock, slowly rolling her tongue up and down my pantie covered penis. Licking all the pre cum tasting and moaning! "MMM You taste so good!" She pulled down my panties and put her mouth deep along my raging hard cock! Dildo in my ass and my sister sucking me off; what a dream! "Ahhh Fuck LISA I AM GOING TOO.... AHHHH AHHHH..." and then I came! All over her face and her dress.... that I was wearing. She began to lick up my warm juice and clean off her dress. She slowly slid up my body, smiled and kissed me. My sperm now in my mouth and before I could say a thing she kissed me deeper, sliding her tongue inside forcing my cum down my throat! "You like that didn't you?" What was I going to say....."Fuck ya!" She stood up, put her pants on and said,"Mom and Dad will be home soon. I want my clothes clean and put away where you found them. But I do have to say Mark. I had a lot of fun! I have got a few ideas floating inside my head, but I really need to sort things out. Are you willing to continue our little lesbian fun little brother?" I was in a trance. I couldn't believe what she was proposing! "Yes Lisa. I can't wait! When and how...." She looked at me and said,"You will find out soon little bother! And let me tell you, you better be ready for what I have in store for you! We are going to have some fun!" To be continued Dressing for My Sister Ch. 02 After that night I couldn't stop thinking about what had taken place. How did things turn out so perfect? I mean I was dressed up in my sister's clothes and playing with myself, using her dildo..... how did she enjoy that? No matter, I was swimming in excitement! Lisa said she had some plans, I wasn't sure what that meant but the anticipation was thrilling! 2 weeks went by, and nothing was done. She just went about her days as did I. We talked like normal and everything was just fine, but I had this feeling that something would change, and change it did! My parents were to go away to Mexico for 2 weeks. I had a feeling something might happen at that time line; or should I say hoping, but she said nothing! 2 days before my parent's left, I received a package from Sears? It was a large box and very heavy. I was thinking,"I didn't order a thing???" My mom gave me the box and asked me what the hell it was "I ordered some electronics from sears... it was on special." It was a horrible cover up, but I had no idea what was in the box! My room was in the basement so I brought the box downstairs and put it on the foot of my bed. I open the box and looked inside.... and what I saw. "Can I see what you got hun?" My mom asked me. I closed the box quickly and told her. "No!" She looked at me. "What the hell is wrong with you?" I told her that is was a gift for her, not electronics, and she couldn't see. My mom looked at me kind of funny. "Whatever son, you are up to something and I don't know if I like it?" My mother left and went up the stairs. I quietly went to the box and opened it up. It was full of women's clothes and lingerie! Beautiful dresses and panties.... bra's and garter's.... stockings and shoes... even had some breast inserts. I couldn't believe this! And in the bottom of the box was a sealed letter. I opened it up. "This is a gift for not only you, but for me. I purchased these things for you to wear and for me to enjoy. I have though about that night every day and have been thinking of other ways that we can make this situation special for the both of us. Please know this is just the start. I will be sending you other packages as we go along with our fun games. The packages won't be as large but just as special! I have a lot of ideas of things we are going to do, but first thing is first. I want you to find a secret place to store our new clothing. I want you to take care of them, have them clean and ready to wear as I direct you... is this understood? Do NOT tell anyone of what we are doing here! As soon as something happens that I am not happy with, this game ends! Do you understand? Good! Mom and dad leave Friday morning. I am hoping you do not have any plans. I have taken 2 weeks holidays, and have a few things in store for the both of us. I advise you to cancel all plans and gear up for one unbelievable 2 weeks!" I didn't have much to do, I do have a job, but getting time off was a non issue. I called my boss and asked for some days off, I said I had a sick family member out of town and didn't know when I would be back. He was cool with it all and now I was set! I was feeling quite scared! I didn't know what my sister was to do with me? But at the same time; I have to tell you, I am so aroused! I was so hard just thinking of the things that could happen! The unknown was so inviting! I live in a finished basement, and down there is a closet. I went shopping for a latch and a lock to install on the closet so nobody could see inside. And all this time in the 2 days since my package arrived my sister has been absent? So that friday morning came I said goodbye to my parents. Lisa wasn't there to say goodbye? Where was she? As soon as they left I grabbed my box and started to hang my clothes. Inside the closet I had put some plastic drawers to fold my lingerie. I hung an asortment of dresses. Some long, others short. Some tight and others not as tight. Most of them were black, 2 red and a real sexy cream colored one! There were 3 pair of pants, a few blouse's and some day wear. The bra and panty sets were to die for! All colors and styles, I couldn't believe! This must of cost her a fortune! We both lived with our parents and did not pay ant rent. This was so we could properly save to buy our own house one day. All this clothes folding and hanging was getting to me! I wanted to dress up so bad, but where to start. Just as I was about to start tying things on the phone rang. "Hello, how are you?"It was my sister Lisa."Did you enjoy my gift?" "Yes I did! Thank you so much, but why?" Lisa stopped for a short second and began to explain. "I couldn't wait to be with you like we were the other night! But I wanted to do this a special way.... my way. Do you understand?" I hesitated. "No I don't, but thats fine sis. I will do what ever you want! I have the 2 weeks off so what ever you have planned is all good." My sister started to breath a little deeper and asked. "I want you to get dressed soon, but first I need you to clean up. I want you to have a shower and shave off all your body hair. I want all of it off completely! After you do that I want you to wear one of the robes I bought for you go to the front door and get a package I will leave for you there. Don't cheat, I will be watching and no more games for you little brother, you understand?" I was in the zone! "Yes I understand!" I can't wait! This game was starting to be fun! I went through my new closet to get a robe. She had purchased 3 of them for me, but there was one that stood out. It was a black satin robe, with sheer sleeves and a lace trim down the semi-low cut neck line, and lace trim on the bottom. It was very sexy! I went to the bathroom, drew myself a bath. I soaked and shaved, and cleaned myself with all of my sister's bath salts and oils so I could smell pretty. As I dry myself I notice how young I looked with all the hair off my body! I wasn't really hairy before but wow... what a sight, and feeling!. I put on my sexy robe and go to the front door. It was about noon at this point and I see the box about 30 feet from the front step. She is playing with me! I have to get the box and have everyone see me in a satin robe? I knew she was to watch so I looked around.... made sure nobody was watching. I walked down the sidewalk and grabbed the box, ran into the house and shut the door tight! Oh man, was that intense! I went downstairs and opened the box. Inside was a wig, and some make up. It was a blonde wig, just past shoulder length, with a bob cut hair style simular to my sister's hair. I didn't know what to do with the make up, so First I put on the wig, looked in my full length mirror and as I looked at myself I noticed creeping up to in in the background was my sister. She was wearing this black one piece jumper that was so very tight to her muscular body. At the top of the jumper it was white and black checker pattern, the zipper was pulled down to expose a large portion of her large d cup breast's. She was all done up, her hair, face, she looked outstanding! I was starting to feel warm inside. My cock was starting to twitch. "You look beautiful Lisa!" She walked up behind me put her arms around me and gave me a gentle kiss on my neck. "Thank you little brother, now it's time that we make you look beautiful. Would you like to feel beautiful Mark?" I stutter,"ye..yesssss. Please make me look pretty....." Lisa then started taking my clothes off. She went into my closet and opened some of the plastic organizing drawers I had put in to keep my lingerie. "You have done a great job with you new clothes baby brother. Now.... what to start you with. What will be the first thing I get you to wear." She pulled out a matching black panty and bra set. It was fabulous! The panties were mostly satin, but had a lace brazilian cut back on them. The bra was mostly satin also and with some lace trim on it also. She grabbed my breast inserts and handed them to me. She also grabbed a pair of nylon stockings with a lace top. They were stay ups so no garter was needed. "Put these on while I look for an outfit." I sat on the edge of my couch and started with the stockings. I rolled them up and pulled them around my toes. Slowly sliding them on I extend my leg out , pulling them up and feeling the warmth of the nylon hug my leg. I put my panties on, and wow! What A fit! They were not too tight but hugged my small round bum perfectly, and covered all of my cock, even as hard as it was! The bra fit well to. This was different than wearing my sister's stuff, she has large breast's and my bra's were only sized to a b cup. Although the cup size seemed small, when I put the inserts in, they fit and looked so real! I rubbed my hands all over my new breast's and looked again into the mirror. I still had my wig on and I really started to believe I was looking like a women! "Here, try this on." Lisa handed me a long black stretchy dress. I slid it over my head and Lisa helped me pull it on. The sleeves were long and flared out past my elbows, the dress almost hit the floor, and had a long slit up the left side. It felt amazing. She sat me down again, opened up the make up bag she had just bought me and began to make the finally transformation. She started with concealer, then eye shadow. I was getting so very hot while she was doing this to me. She was so transfixed on the task in hand, without a doubt I knew I was going to look beautiful! As she put on the lipstick she smiled. Looked at me and said, "Done! Take a look sweetheart!" She showed me a round mirror, and as soon as she put it to my face I couldn't believe it! I couldn't recognize myself! I was so pretty! I stood up and walked to my mirror and looked at the entire package. I was stunning! It is like I was meant to be a women. Lisa walked over to me looking sexy as all hell in that fancy jumper of hers, her tits looked so inviting. I wanted to touch. She looked deep in my eyes and gave me a deep long kiss! Our tongues tangled up, the taste of lipstick was just a dream to me! As we broke our kiss my sister spoke. "I have never wanted anything more than I have wanted this right now." I didn't know how to respond. She looked deeper into my eyes, "I have never felt this close to anyone in my life, this feels right.... you feel right! And not only are you my little brother, but you look like my beautiful little sister that I have always wanted!" Lisa just kept staring at me. "I feel the same way Lisa! You make me feel like nothing I have ever felt before. I feel sexy, and manly.. it is hard to explain, but all I know is I couldn't feel this comfortable with anyone else. And you look so perfect! I want to touch you and feel you....." As I was talking Lisa placed my hands on her breasts. Feeling the fabric of the low cut half way across her big round tits, I unzipped her jumper all the way down to her belly, and in an instant, her big beautiful tits popped out! I began to fondle them lightly touching her large nipples. I moved down to kiss them, squeezing her left breast as I kiss and suck on her right one. I place my tongue on her nipple and bit down on it. She gasped and looked at me with a grin. I continued to suck and bit tasting her skin feeling her heat. I unzipped the jumper down to her pussy, and thats were the zipper ended. She stood up and let me peel the jumper off her. She was wearing a black satin thong, very skimpy at best. She stood above me as I was sitting on the couch. Her feet beside my thighs, she pressed her panty covered pussy over my face. "Smell it, give it a taste." I slowly inhaled my sisters cunt. Light seepage of her love juice came through her panties so I place my tongue on it, licking all of her goodness!. "Mmmm yes little brother, lick my pussy... taste your sister's cunt!" I started to lap up all of her juices.I pulled her panties to the side and put one finger in her. I put my lips on her clit, sucking and fucking her. "Yes, fuck yessssss. Fuck it baby fuck your sister." She dropped onto my lap, now grinding on top of my full hard cock! She leaned in to kiss me, her breathing as heavy as mine.She began feeling my new breasts. "Wow what perfect little tits we have here. They feel so nice." She was really starting to hump and grind. Hard and slow. I so wanted to cum, but did not want this to end. Lisa continued to fondle my tits and grind into my cock. "Lisa I am going to cum. I am sorry but I think you are making me cum." I was getting close. She slid off from on top of me and went to the floor, she lifted my dress and licked my cock through my panties.... there was so much pre cum! She pulled off the panties and took the hard cock into her mouth. "Mmmm I love how you taste little brother! Your cock is so wonderful! Now licking the entire shaft, I look at her, feeling my breasts as my cock gets sucked by my sister.She begins to stroke it hard and fast. "Cum for me Mark! Cum in my mouth!" Her lips pressed to the tip of my penis, I continue to feel myself up, my beautiful dress, my perfect little tits! "Ahhh yesss Lisa suck me!" And then as my cock tensed up I let it go, and Lisa took all of it! She began sucking and jerking me off, eating everything I had! "Come give your sister a kiss." I lean into her and she kisses me deeply, tasting myself, loving my cum. "Come on Mark, lets get you cleaned up." I went to take off my dress and she stopped me. "No, no, no little brother! Do not take that dress off! We are not done! We have 2 long weeks of this, and I am not wasting a second! Come on I will clean you up and make some supper. We have a long night ahead of us!" This was to much! I couldn't wait.... well I wouldn't have too!