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I've been dressing as a woman for many years, starting out with just trying on my mom's bras and stockings and high heels while she was out. Then as I got older, I began ordering things on-line and having them delivered to my post office box downtown. It's amazing what you can order, and no one knows.
I've established quite a closet full of sexy things for play time...skirts, dresses, suits, stockings and thigh highs, high heel shoes and boots, corsets, bras, slips, and a whole lot of make-up and wigs. I've become quite good at dressing up and looking like a woman. I have to admit thou, that most of my outfits are skanky, slutty looking, which I love. Nothing more hot than to be in a short, tight skirt, thigh high stockings with garters, and 5" high heels to turn heads. Yes, turn heads...I've been dressing and walking around town as Amanda for quite some time. It's so exciting pretending to be a hot slut, or prostitute, and having men...and women...take a look at me. I don't even care if they can tell I'm a man under my clothes...it's fun, and I do it.
One day while just finishing putting on a finishing touch of my lipstick before going out to walk around, my older sister just walked in the door and we met in the hallway of my house, face to face. She just stood there, with her mouth open, looking at me, up and down. I just stood there too...wondering what she was going to say. It seemed like hours, but it was just seconds. She finally found the words, and said, "wow, you look great". I couldn't believe what I just heard. I replied, "thank you, I've been practicing for quite a while". She said, " I can tell, and you look fantastic".
Now, my sister and I don't live close to eachother, and when we do get together for family functions, we do give eachother kisses and hugs, and we do love eachother, just like brothers and sisters do. I've always thought that my sister was a good looking woman and have had dirty thoughts of having sex with her, but thinking of it was a long way from reality...besides, it's taboo and I think against most state laws.
Anyway, my sister then walked up to me and kissed me...on my painted lips, and gave me a hug, saying, "it took you long enough". I didn't know what she meant, but she explainded that she had always known that I was a crossdresser from early on, and thought it was cute. She asked if i was bisexual or gay, and I said that I'd had bisexual thoughts, but that I liked women. She then asked if I was going out, which I replied, yes, I was. She asked where I was going, and I told her that I was just planning on walking around town for a bit. She responded that two sexy women should be going to a bar for some fun, not just walking around. I was shocked...she wanted to take me to a bar? She told me that she routinely goes to a gay bar because she can be left alone there, unlike a regular bar where men are always hitting on her. She told me that since I looked so good, and that I've had bisexual thoughts, that I should go to a gay bar and have some fun. I agreed, although I was a bit nervous...I've never been to a public place dressed as Amanda before and didn't know how it would go.
We arrived at the club, walked in, and made our way to the bar and sat down. I was immediately eyed by most of the guys in the club, and some of the other crossdressers that were also there. They just looked at me and smiled...which made me feel good and accepted. I looked at my sister and smiled, and said, "this should be fun". We ordered drinks and began to look around. My sister said that there are some pretty good looking guys here, and said that she wanted me to pick one out to take home. I said, "what, you want me to pick one out to take home? Are you nuts?" She laughed, saying that she was serious, and that she wanted me to go all the way with this crossdressing thing of mine and feel what it's like to be a woman, sexually, blowing a guy and to have him fuck me. I told her, "no way, I'm not doing that". She laughed again, saying that she would divulge my secret to the rest of the family and my co-workers if I didn't do this. I couldn't believe she would be so mean, but there was no way I wanted anyone else to know what I did for fun, so I agreed. We then both noticed a nice black man by the pool table who kept eyeing me...or us...I couldn't tell, and before I could say anything, my sister got up from the bar stool and began walking over to him. I was mortified...she was serious about this.
When she reached him, she whispered something in his ear, and then they both looked in my direction, and smiled. They both walked over to me, and he grabbed my hand and led me out of the club. He walked me over to his car, which was next to ours, and he said that I was going to be his date for the night. I didn't know what to say. My sister pulled up next to us and said, "follow me". We followed her to my house and we all got out and went inside. My sister told me to go upstairs, freshen my lipstick, and take everything off except my high heels, thigh high stockings and bra and get on the bed. I just stood there, not wanting to do anything, but she reminded me of what she was going to do if I refused. I went upstairs and got undressed and got into bed. I could hear both of them laughing and getting a drink. Moments later, I heard them coming up the stairs, and then they walked into the bedroom. The black man sat on the edge of the bed, while my sister began undressing. I asked her what she was doing, and she just said, "don't worry about it, just lay down and relax".
I laid down, and immediately felt my sisters warm lips around my cock. I sat up yelling, "what the hell are you doing?" She laughed, pushing me down, and continued. I sat up again, at which point, the black man got up, came over to me and held me down, telling my sister to continue. My sister gave me the most unbelievable blow job I ever received...or maybe it was just so exciting that MY Sister was doing it! The black man just watched and smiled, all the while playing with his cock that was sticking out of his down zipper. My cock was rock hard in seconds as my sister continued to blow me. She then stopped, asking me how that felt. I told her it was amazing, and asked her what the hell was going on? She said that she always thought I was a good looking guy, but that I made an even more amazing looking woman, and said that she just wanted to give me an experience that I wouldn't forget...adding, it's just sex, so take it easy. I was trying to take it easy, but just couldn't believe what was happening.
The black man then stood up and got undressed. When he took off his underwear, I almost shit myself. He had a cock that was huge...must have been at least 11" long and about 5" around. It was like something from National Geographic...I kid you not. My sister was also amazed, but didn't hesitate to go over to him, push him onto the bed, and begin to suck on that monster. I just laid there in amazement, watching my sister give this guy's cock a working over. It was so hot. I just played with my cock wondering what the hell was going to happen next. I didn't have to wait long to find out. My sister stopped blowing this guy, and told him to relax and watch. He sat on the edge of the bed again and continued to play with his monster of a cock. My sister crawled over to me and kissed me passionately, while jerking my cock...it got me sooo hard having my sister's lips on mine, and her tounge going in and out of my mouth. It was like a dream..but a good one. My cock was so hard. She stopped kissing me, and got up on her feet, straddling me, and then squatted down right over my cock. I couldn't believe was was happening...my sister was sitting on my hard, throbbing cock. She moaned as she sat all the way on it, smiling at me all the while, asking me how it felt. I just smiled back, saying, it felt amazing. She started to ride my cock, lifing her body up and down on it, pushing me to the edge...I told her that she should stop because I was about to cum and that I didn't think I should cum in her pussy...there was just something wrong with that. But then I thought, this whole thing was wrong. She agreed and dismounted my cock.
My sister then turned towards the black man, saying it was his turn to fuck something. She laid down next to me and he mounted her and shoved his huge cock deep into her pussy and began to fuck her like there was no tomorrow. She cried out in pain and pleasure and he continued to fuck her. She grabbed my hand, squeezing it hard with every thrust of his body. She yelled at him not to cum inside of her, and he immediately stopped, saying that he as just about to explode. She told him that he wanted him to fuck Amanda and he said that he couldn't wait. I yelled, "what? Are you kidding?" They both looked at me and said, "no, we're not kidding. If you're going to dress like a slut, you're going to be treated like one too." At that, my sister reached into her purse, pulled out some ky jelly and squirted it on to and in my ass. I tried to get up, but the black man held me down, laughing, saying that I'm not going anywhere until he gets what he wants. He then came over to me, pushed my high heeled, stocking legs high over my head, which lifted my ass up, and pushed his monster of a cock against the opening of my ass. I screamed to my sister that I didn't want this to happen, but she just laughed, coming over to me and pressing her lips against mine, muffuling my screams. With her face in mine, and her tounge inside my mouth, I couldn't see the black man, but felt his huge cock begin to press into my ass...the head of his cock then popped into my tight, unwilling ass, and I again screamed in pain. My sister yelled at me, and said that this wasn't going to work. She told the black man to hold me down while she tied my hands to the bed posts and shoved her panties into my mouth. She told the black man to continue what he was doing, and told him not to be so gentle this time. My sister then wrapped her lips around my cock again, while the black man started to push his cock back into my ass.
I eventually just gave up, started to cry, and felt the most intense pain as the black mans cock pushed its way into my ass, all the way to his balls, and all the way to my stomache. The pain was too much to bear as he began to wildly fuck me...driving his huge cock in and out of my ass, almost lifting my whole body off the bed with each thrust. It was unbelievable. My sister contined to blow me as he fucked me. I was almost ready to pass out in pain, when I heard the black man yell, "I"m going to cum". I didn't want this guys to dump his cum into my ass, but what was I going to do? I couldn't move, and my sister certainly wasn't going to help. I then felt his huge cock begin to swell, and he stopped fucking me. His cock began to pulsate while in my ass, and then I felt it. Stream after stream of hot cum was being squirted into my ass...the black man was straining and moaning in pleasure as he continued to dump load after load of his seed deep into me. I began to worry about diseases and things, but there wasn't anything I could do. My sister was bobbing up and down on my cock and that was too much to handle. I felt my cum beginning to boil and tried to move away from my sister's mouth, but it was no use. I exploded into her mouth, and she stayed right on top of it, sucking and swallowing every drop of her brothers cum. I still couldn't believe she was doing this to me.
After I finished cumming, the black man slowly pulled his cock out of my ass and came over to me. He removed my sisters panties from my mouth and shoved his wet cock into my mouth. He pushed so hard, that his cock went right down my throat, choking me...and his balls were right on my chin. He began fucking my mouth, and I began to wonder if he was going to cum again. I didn't think so, since he just dumped about a quart of his cum into my ass. My sister stood up, and just watched as the black man continued to fuck my mouth. I could feel his cock begin to get bigger, and I couldn't believe it. He began fucking my mouth faster and faster and what I thought couldn't happen, did happen. He yelled out that he was cumming again, and he began to dump another load into my throat. It was alwful...his cock tasted like my ass and now he was shooting his cum into me...all i could do was swallow every drop since he certainly wasn't pulling out. My sister just laughed, saying, "now you know what us women put up with.".
The black man pulled his cock out of my mouth, got off the bed, got dressed and left the bedroom. My sister got dressed, went to my bag and got my lipstick out, reapplied it to my lips, and told me that was round one. She then tied my legs to the bed posts with a pair of her stockings making it impossible for me to get up. She then came to me and whisperd in my ear, "I'm going back to the club to find you another date. We've got all night. Be back soon Amanda."