Sister Helps Brother Cross Dress

I am 18 and just graduated high school. I live at home with my Mom and older sister. My sister has been lusted after by all of my geeky friends, as she is the opposite of me. I am 5'7", 130lbs and a nerd while my sister Debbie is 5'9", 130lbs, very toned and 34a breasts. I know because I look through her things all the time.

I love to dress when I am alone in either my sister's or mom's clothes. Since my Mom was going out of town to visit family and my sister was spending the weekend camping with her boyfriend, I was imagining the fun I would have alone until my 2 friends called and said "Let's get some beer and porn movies to watch Friday night." I agreed not wanting to seem like more of a loser than I already am.

Joe and Tim showed up with beer and whiskey and we started drinking. Since I am so small, the alcohol seemed to hit me quicker. I put in the first porno and we watched the girls and guys go at it. We were all getting noticeably horny and Tim said let's pull out our cock's and stroke them. We quickly pulled down our shorts and I noticed that I was the smallest and Tim was the biggest. Tim said, "I wish your sister was here."

I guess it was the alcohol and being so horny but I said "Just wait a few minutes." I ran upstairs and found Debbie's mini skirt, panties, thigh high stockings, low-cut top and bra. I went to my Mom's room and found a blonde wig she had bought for Halloween. I looked in the mirror and I looked pretty good without makeup so I didn't even attempt any. I started to attempt putting her high heels on but with my drunken state I couldn't even begin to walk.

I headed downstairs slowly. I started wondering what the guys would do but my horniness and drunken state made me push on. I walked around the corner and the guys saw me, and Tim said "What the fuck dude?" I blushed

Then Joe said "Dude you are almost as hot as your sister." Tim patted the cushion beside him on the couch and motioned for me to sit down as I blushed and walked over. Tim grabbed my hand and moved it to his crotch and I did something I have always wanted to do. I started stroking his 6" cock and my other hand reached over to Joe's 8" cock. Tim leaned over and gave me a big kiss on the lips and I felt his tongue probing my mouth. I was so turned on I thought my 4" cock was going to explode in my sisters panties.

After the kiss, Joe directed my mouth towards his cock. As my lips wrapped around the his large shaft I realized I had always wanted to do this. Joe was moaning as I kept moving my mouth up and down and using my tongue. Joe said "This is better than when Amanda gave me that blowjob last year." I heard Tim walk away and come back as I felt the skirt lifted and panties pulled aside.

I felt a cold liquid on my ass and a finger probing my ass. I wasn't sure I wanted this but I loved being their slut and it turned me on knowing my sister was watching. As Tim squeezed his cock into my virgin ass, I felt Joe's cock swell in my mouth and his cum exploded down my throat. I swallowed as fast as I could but it just kept coming. Some ran out of my mouth and down his shaft as I came up for air. He looked down and said "Lick me clean slut" and I proudly did.

Tim pulled me tightly against him as his cock penetrated me. He started moving faster and faster giving me the fucking that I now know I have always needed. As with Joe in my mouth, Tim did not last long in my ass. I felt his cock grow slightly before the spasms and his grunts as he filled my bowels with his cum. He slumped back onto the couch as I looked over and noticed that Joe's cock was getting hard again. Tim said, "Joe you need to fuck that little slut."

Joe replied, "I am not into that and pushed his big cock back into my mouth." Tim was quickly getting hard again so he moved right up behind me and easily slid his cock into my cum filled ass. He grabbed my hips and kept thrusting harder and harder.

I was sucking Joe's cock with wild abandon and I felt him getting close. Tim said, "let's cum all over her face." They pulled out of my holes, I knelt in front of them with my mouth open as they both started squirting cum everywhere. It was in my mouth, on my face and down the top. They both went to make another drink and I passed out on the couch.

I woke up early in the morning to my sister tapping me on the shoulder and saying "wake the fuck up cum slut." I jumped up still in a drunken haze and all I could do is ask what she was doing home. She said "I dumped my cheating boyfriend and came home to see my brother dressed in my clothes and covered in at least several guys cum." I tried to explain and she said "I always knew you were trying on my clothes but I didn't know you would go this far." She asked me who it was and if they were still there. I told her Joe and Tim as I blushed and explained the porno and drinking. I told her how big Joe's cock was and how he only let me suck him. She was instantly interested and said let's go find Joe.

We found Joe passed out on Debbie's bed and she saw his snake of a soft cock. She said, "Go back to sleep or sit out here and listen, I am going to have some fun in here". She shut her door, I heard whispering of her clothes sliding off.

I hear Tim say "what the..." and he must have realized it was Debbie. I stood there listening to the grunting and groaning and playing with my little cock. I heard Debbie climax and shortly thereafter Joe. I heard Debbie getting out of bed and I hid my cock.

She opened the door and came out and said "I am glad I found you here, I brought you a present". She handed me the cum filled condom and I looked at her questioning. She said "You love cum, so here is your dessert".

Later that week our parents were home and Debbie came home late from a date. She snuck into my room and reached into her panties and pulled out a tied and very full condom. She said "sissy bro, I have been keeping this warm for you." I opened the condom and gobbled it down like a hungry puppy dog.

Over the next few months, my sister brought me home condoms almost nightly and she would give me her worn out clothes to add to my collection. I decided to go to the same college as Debbie. Somehow, I managed to score a single dorm room which was smaller than most. It was 2 weeks into college and all of the frats and sorority parties and hazing was in full swing. It turned out her sorority had lost a bet with a frat house and the prize was her sorority picking a girl to sit behind a gloryhole and take care of all of the frat house boys. None of the girls wanted to do this. It was mentioned by Debbie that she liked to dominate me and make me dress as a girl and I was going to college across town. They all quickly agreed that I must be the one to do this for them. I was promised all sorts of prizes like seeing the girls of my choice naked, free girl clothes, etc and I reluctantly agreed. Later that night and laying in bed, I worried about how many guys this could mean.

I got there on Friday night and the girls all helped in making me pretty. I went into the gloryhole booth, which was a bathroom with a modified door. The other girls first sent Debbie in to take pictures and video of me in action. The first few guys were nervous pledges who didn't last long before filling my mouth with their cum. I was on a cum high as I turned around and smiled for the camera showing my cum filled mouth before swallowing. Debbie had brought in some alcohol to help me wash it all down. As the night went along the guys kept showing up. I know I sucked guys from about 5" to about 9" and I was getting pretty drunk. My jaw was pretty worn out when the last cock came through. I just grabbed some lube and a condom that I saw earlier on the counter. The guy started to complain as I put the condom on until his cock was directed towards my tight ass. His 6" cock was very long lasting and he pumped away for what seemed like hours before cumming in the condom in my ass. I peeled the condom off and drank down the cum while Debbie watch through her video camera. I collapsed on the floor but soon the door was opened and the girls all stood there thanking me for being such a trooper. I was led into the front room where the girls as promised disrobed including my sister. My little cock was hard in my panties and a girl named Tina noticed it. She said, "You look like you could use some relief, do you mind." I blushed and shook my head as she came forward. She noticed and pointed out that my panties were already very cum filled and I must have enjoyed being the cum slut. Tina used a couple of fingers to stroke my little cock, which she called cute. I came in under 30 seconds all over her hand. Debbie told her to feed it to me and I gobbled it down while 25 girls looked on.

The girls decided it would be fun to have me move into the basement room. The rule was I had to be dressed as a girl there but could leave for class in guy clothes. Over the next year, I had many cum filled condoms from all of the girls. The rule was they had to keep it warm by tying it and storing in or near their pussy. I felt in heaven as I licked the outside fist tasting their pussies before filling my mouth with the salty cum. One night towards the end of the school year, Tina was very drunk and she came into my room. She said, I forgot to use a condom with my boyfriend but I still have cum for you. She pulled down her panties and first let me lick them clean which I loved this vs the condom. Then she climbed up and sat on my face. I was in heaven licking pussy for the first time and especially since it was filled with cum. I am pretty sure she came three times and I know that my little cock came twice while she rubbed it.

After that night, it became a regular thing for Tina to come in and have me lick her clean. It was all from her boyfriend and I was amazed at the differing amounts and taste from the same guy. Unfortunately, school came to an end and Debbie graduated with many of the other girls including Tina. I knew that things would be changing as Debbie was moving away and the sorority house was changing as well. I accepted an offer from another college across the state.

I ended up finally dating a girl in my senior year and she decided that she wanted to save herself for marriage. About a year after graduation we finally got married and our wedding night was a disaster when she realized how small my cock was. She was not a virgin so she knew there was bigger and longer lasting guys out there. She didn't say anything but the coldness was there.

Several years into the marriage, I knew she was cheating on me and the only thing that bothered me was I wanted her to do it in front of me but was too scared to bring it up. I would confide in my sister during phone calls. Debbie also knew that I would still dress in women's clothes when Anne was out of town.

Debbie got married to a very rich guy and it wasn't but 6 months into the marriage that she knew something was wrong. She called me up one night and asked if I could come for a visit, as she needed a favor. I asked how she would repay jokingly and she said, I have a plan to help you. Debbie explained that she had found out her husband was visiting the local TS and crossdresser bar. She had a feeling that he was going there, picking them up and fucking them.

I arrived and she took me to a seedy motel near the bar. She had rented the room for the last week and paid a guy to install hidden cameras. Debbie helped me me get dressed in some skanky but sexy clothes. I went over to the bar on Wednesday which was one of the nights that Carl visited. I wasn't in there long and there were guys trying to buy me a drink. I saw Carl come in and he seemed to notice me and made a beeline for me as the new girl in the place. He asked if I was from around here and I said no, I was visiting friends and staying in the hotel across the way. I told him that I loved getting away so I could dress freely and get my urges out. He had me out dancing and grinding his crotch into mine and thrusting his tongue into my mouth. I told him it had been years since I had been with a guy and asked if he would like to come over to my room. We quickly left and got comfortable in the room. I left most of my clothes on as I undressed Carl and started sucking his cock. He let me keep going until he came in my mouth and I was amazed that he stayed hard afterwards. He manhandled me over and put on the condom. He grabbed my lube from the table and slid his big cock in quickly making me gasp. He started pounding away at my ass calling me names like sissy slut and bitch while slapping my ass. After about 20 minutes, he pulled his cock out and peeled of the condom. He flipped me back over and said jerk me off bitch. I did and within 10 seconds ropes of cum splattered my face as he got up and quickly dressed and left.

My cell rang seconds later and it was Debbie instructing me to get cleaned up and changed. She said, I have another room for you on the other end of the building in case he comes back. I moved hotel rooms while Debbie confronted Carl. Carl moved out and promised to change.

I was hanging out with Debbie the next night as she called Anne. She told Anne that that she wanted to chat about our sex life. I could hear the silence on the other end when Debbie told her she knew Anne was disappointed with my penis size and ability. Over the next hour they discussed me thinking Anne was cheating on me, my want to be cuckolded both watching and not, my want to eat cum and wear women's clothes. I know several times Anne was ready to divorce me but in the end Debbie convinced her that this will be best and the most fun for everyone.

I can't wait to get home....