Hello, thanks for stopping by to read this. I will tell the story that started it all. The beginning of my spiral into depravity and becoming a sissy white boy. Names were changed for story purposes, but someone reading this might have been there and know who I am...

One day when I was younger and in high school we had off school for summer break one of the older girls named Madison from the neighborhood walked over to me while I was sitting in the yard and told me she wanted to walk in the woods but she was scared to go herself. She had this duffel bag with her around her shoulder but I didn't pay any mind to it. I said "Don't worry, I will walk with you" and she started laughing hysterically. She said, "What the fuck are you going to do, you are a pathetic little wimp!" Wow, talk about a blow to your ego.. watching this hot-haired girl insulting me.

I was a little embarrassed and I stood up straight and said, "I'm not a little whimper, I'll prove it to you!" That was my attempt to impress her, but she just giggled and said, "That's so cute and adorable, are you gonna be my little protector" as she laughed. I said, "Absolutely, I'm not scared!" She just glared at me with those crystal blue eyes and grinned. She happened to look down and see that I was hard as a rock and my shorts were standing up and she let out a laugh.

I felt a little uneasy as she just stared at me and then she broke the silence and said "I bet I can prove you are a little sissy wimp!" I said, "you are on, let's go!" We started to walk and then she stopped and looked at me with those crystal blue eyes saying "Don't walk next to me like we are equals, you walk behind me like a little sissy dog" while she was laughing. She said, "I really should have you on your hands and knees like the wimpy dog you are!" I didn't know what to say because I thought she was so hot and I wanted to impress her.

I just blurted out ah ok. She gave me this mean look and slapped my face so hard my ears were ringing and said "Don't yeah ok me, you call me Goddess or I'll slap your little sissy face even harder and make you cry." I just stood there in pain and disbelief and mumbled "Yes Goddess." She laughed and said, "See that's a good little sissy that knows her place!" I just looked at her puzzled in pain and disbelief and put my head down wondering why she just referred to me as she. She started walking again and I followed behind her not wanting to get slapped again. As I was a little dazed and confused she stopped again and I immediately stopped so that I was behind her. She could see I was conflicted and confused and she stepped towards me and said, "Awe look your little cheek is red" and leaned over and kissed the handprint on my face. I was brought back to life and fireworks were going off in my head. OMG, she just kissed me... I thought this was going to happen and it was worth the pain and the humiliation that just happened. Then she started walking again and I followed behind her with a smile and a hard-on!

She was beautiful with her long curly blonde hair, crystal blue eyes, tan smooth skin, and a newly forming teenage body. Her smile was mesmerizing and almost intoxicating especially when she had an evil grin. She highlighted her curves by wearing tight bicycle shorts and a tube top so every movement caused her curves to bounce for everyone to see. I was almost hypnotized by each of her movements.

I was a virgin and was just learning things of a sexual nature. I had jerked off to the mental images that I had of Madison and I practically drooled every time I was around her. I was always adjusting my shorts and she would catch me and just look at me with an evil grin and laugh. I would get kind of embarrassed and that seemed to make her laugh even more.

I remember thinking wow this is finally my chance with Madison in the woods... was she gonna tongue kiss me or maybe touch me? I started to get nervous because I didn't know what to do with girls and wasn't sure how to react. I didn't know how to kiss I didn't know anything. I was excited and thought this was my chance! The kiss that she just gave me on the cheek was the first kiss I had from a female that wasn't my mom.

I was dizzy from all the thoughts and excitement going through my head. Then I was quickly brought out of that hypnotic state when she stopped again turned around to face me and put the bag on the ground. She said, "Close your eyes and don't open them or I will bitch slap you again!" I did as I was told and I stood there on the walking path at the edge of the woods with all kinds of things running through my head. I couldn't figure out why she just abruptly stopped right at the entrance to the woods, but I stood there with my eyes closed because I didn't want to get hit again. I was surprised that such a beautiful girl could hit so hard.

I heard her open the bag and then I heard her moving things around in the bag and then she said, "There it is.. this is so cute." Then I felt her stand behind me and whisper in my ear "Are you scared now, wimpy sissy boy?" Her breath in my ear and her voice sent chills down my spine. Her words scared the hell out of me because of her tone and she now didn't seem like the innocent feminine beautiful girl that I had craved and jerked off to many times. I was quickly brought out of my trance-like state when she kissed my ear and then bit it. I was extremely excited and let out a yelp! I said, "he'll no I'm not scared" in a crackling voice which she heard in amusement and started laughing. Then I felt her put something around my neck and then I heard a buckle and felt some more movement. What the hell did she just put on me? I wanted to look so bad but was afraid of her slapping me again so I just stood there.

I heard her voice in front of me again and she said, "damn that looks so good." I thought.. what what looks good.. omg what did she do to me? Then after some silence, Madison said, "ok sissy boy open your eyes." I hated that she kept calling me sissy boy. I opened my eyes and saw that she was holding a chain leash in her hands and to my horror I followed it back and it was attached to whatever was around my neck and I reached up to see what it was. Madison slapped my face hard and I saw stars and I fell. She stood right over me with an evil glare and said, "Don't you dare touch that dog collar you little sissy bitch." "This is your last warning the next time I will beat you senseless you little bitch" she exclaimed in an evil voice. I just lay there in shock and horror. She said, "I told you that you were a little sissy bitch and I was gonna prove it and we haven't even gotten into the woods yet.

Madison pulled on the collar as hard as she could and it was choking me so I jumped to my feet. She said, "Let's go sissy bitch wait till you see what I have planned for you." What the hell was she talking about? She said planned and that means she has been thinking about this for a while and I got nervous. Then I thought about the bag she was carrying.. omg what else does she have in there? Then I was brought back to reality as she yanked the collar hard again and I tried to keep up with her. I could just imagine what that looked like to any passersby.. a beautiful teenage blonde girl in a revealing outfit pulling a boy around on a dog collar and a leash. I was embarrassed and hoped no one was watching or seeing it. What a pathetic sight I must have been.

We made it into the woods and she stopped by a tree. She looked at me and said, "Wow, you are brave!" Then she said lean with your back to the tree and I did immediately. I remember thinking omg it's gonna happen right now. I completely forgot about the events that led up to this moment and could only think about how hot Madison looked and I was about to be rewarded for my bravery. She walked right up to me leaned up against me and kissed me on the lips.. I almost passed out with excitement because everything was getting to me. What a great kiss and I couldn't believe this just happened and I just lost control and blew my load in my shorts. She started laughing hysterically and said, "Omg did my little sissy just cum in his pants from a kiss?" "That is so pathetic she scolded" and I put my head down in shame.

She then put both hands on my face and said, "It's ok my little sissy you can't help that I excite you beyond control!" "It's not embarrassing it's hot and has my panties all wet." OMG did she just say I got her panties all wet? Then she looked right into my eyes and said we should switch panties so you can feel how wet I am and I can feel all of that cum on me." Did I just hear that right.. she said panties but I wear boxers and she wants me to put her panties on so I could feel how wet they are and she wanted to feel my cum.

Without hesitation, I said yes Goddess not wanting to be slapped again. She said, "OK take your panties off, and then I'll take mine off." I quickly fumbled with my shorts and boxers and had them off faster than I have ever taken them off in my life. I didn't even realize what I had done because all I could think of was I was going to be able to finally see Madison naked. My dreams coming true! Then reality hit me like a ton of bricks she broke out laughing and saying, "What the hell is that, it looks smaller than my pinky omg that is a pathetic-looking tiny dick." She said, "Actually it looks smaller than my clit" as she laughed. I stood there in humiliation and disbelief as she laughed and teased me. Then she looked me in the eyes and said, "OK close your eyes and I will take my panties off." What.. did I just hear that right she is going to take her panties off even after this.. oh no she said close your eyes so I'm not going to watch her. That was disheartening, but I thought at least when I opened my eyes she would be naked. So I closed my eyes and I heard some movement and then after what seemed like an eternity, she told me to open my eyes.

I opened my eyes immediately and saw that she had put the tight shorts back on but she was holding a pair of frilly bright pink panties. She pulled the panties up to my face put them right on my nose and said, "Do you smell how wet I am?" I took in a big sniff and was intoxicated by the smell. Then she said, "OMG you are so messy from cumming in your shorts let me clean that mess up" and she bent down and let out a loud laugh. Then I felt her start wiping the cup from my body. Then she stood up and said, "Open your mouth" but I guess I didn't do it quick enough because she grabbed my balls and squeezed. She squeezed so hard I let out a loud cry and she shoved the cum soaked panties in my mouth and laughed. I can't believe this just happened.. omg the taste is nasty no no.. she then tightened the leash around the tree so I couldn't move my head. I couldn't believe the situation I was in. Completely demoralized and confused about what was going on and why Madison enjoyed this so much. I was humiliated and felt helpless.

She then said, "Omg I'm sorry, I forgot the panties were covered in cum.. that is nasty so let me take them out of your mouth" as she pulled them out. Then she bent down and said, "Lift your leg" I did and then she said, "Now the other" and I did. She said that's a good girl now look at you in those bright pink panties, they make you look so feminine." To my horror she had the cum soaked bright pink panties on me. Then she said to me, "Get on your knees as I lower the leash." I did what I was told and I was on my knees she reached into the bag and pulled out a rope and before I knew it I was on my knees tied to a tree in the woods. Then she reached into the bag and pulled out some lipstick and makeup and started applying it. I tried to turn my head and she stuck her foot right on my balls and said, "If you move again I will stomp them until they burst!" I didn't move an inch and after a bit of time, she said, "Alright I'm done and now you look like a cheap hooker" and just laughed.

She just stood there looking and I thought my torment was over. Then I heard her yell, "ok she's ready." I was wondering who she was yelling at or if she was just tormenting me more. Then I remembered earlier that she said she planned this and I got scared. Suddenly I heard footsteps and then other older teens from the neighborhood started appearing in my line of sight. I couldn't believe this was happening. I was surrounded by several of the neighborhood teens and then I noticed it was all white girls and all black teens. They were laughing and insulting me and I was so humiliated. Madison said, "See, I told you he was a little sissy bitch." "Just look at those girly panties that she is wearing and she came all in them because she was excited for what was gonna happen." I thought to myself she just said what's gonna happen, not what has happened does that mean there is more.. no please no. I'm so humiliated as it is.

Then I heard Madison announce to the crowd that now is when we get to see her turn into a sissy. I heard one of the older girls say, "No way he's not going to do it.. there's no way .. he can't be that much of a sissy." The crowd broke out in laughter. Then Madison said, "OK break out the money, and let's see. I will pay 20 bucks for every dollar you bet if she doesn't!" Then Madison leaned into my ear and said "You're about to make me some money bitch." Then I heard and saw a bunch of people passing money around and making bets. I was shaking in anticipation of what she was talking about and one of the girls said, "Look she is shaking with excitement.. she loves it!" The crowd erupted in laughter again.

Then Madison reached into the bag and grabbed a device and she started hooking pads to my balls. Then she whispered to me, "There's enough electrical current in this to fry your balls so if you hesitate I will turn it up.. do you understand?" I looked at her with fear in my eyes and she zapped me and I jumped and let out a scream and they all laughed. She said, "That was only on one and it goes to ten so you better do what I say without hesitation or I will turn it up and leave it on for an hour!" I immediately shook my head yes because the pain was so intense from the first time she did it I never wanted to feel that again. Then she laughed and said, "Good I'm glad we agree, but just in case I am turning it on and leaving it on the warm-up setting just to remind you." She turned it on and it hurt so bad I was bouncing around she laughed and announced, "Looks like Tyrone is in for a bouncy ride" and they all laughed.

Madison sat right next to me and said, "If you hesitate I will turn it up and if you learned anything today you should realize that I won't hesitate to do it." I just nodded yes. Madison said, "Here we go, Tyrone come on over and put your big black cock in her mouth." No.. no.. no what the hell is going on she is going to make me suck a big black cock and do it in front of the whole neighborhood... no way that is so humiliating and degrading. As he started walking over Madison looked at me and said, "Remember if you hesitate I will fry your balls and I will enjoy it." Just then Tyrone pulled out his massive black cock and put it in my mouth. The crowd went crazy with chatter and laughter. I could hear things like she likes BBC, look at that white sissy worshipping BBC, what a sissy faggot, I knew she liked black dick and this went on for what seemed like days as I sucked my first big black cock.
Madison leaned into my ear and said, "I am so proud of you my little white sissy bitch, I knew you liked big black cock." She also said, "I knew you were too much of a sissy to fuck me and you were using me to get to the big black cock" as she laughed at me.

Then she said, "When he is ready to cum you will swallow every drop or I will fry your balls" with a big smile on her face. She announced, "I told you she would worship black cock, now watch as she swallows every drop of black cum!" Then she turned the intensity up and I was bouncing like crazy because of the pain, but I must have looked like I was cum craved and would do anything to get his cum in my mouth as quickly as possible. Tyrone said, "I'm getting ready to fill this bitch's mouth with some black cum" and then let out a roar as he flooded my mouth. Everyone clapped as they saw me swallowing all the black cum I could handle. Then Madison turned off the electrical unit and said to Tyrone that was hot now let's go fuck. Madison and Tyrone left and I was sitting there slumped over.

One of the other black teens Malcolm came over with Becky and she said "If you suck his big black cock like you did Tyrone's I will let you out" as she patted me on the head. So I shook my head yes. I began to suck Malcom and I heard Becky say, "Would you take a look at this, she can't stop sucking black cock she loves it." Then Becky said alright the rest of the big black cocks line up for your turn. Becky said to Malcolm, where are your manners? I told her that if she sucked you off like she did Tyrone I would let her go, so you need to let all of these guys go first so they get to get their nuts off besides we don't want to deprive her of the black cup that she loves so much. I was so deflated and humiliated as I sat there and sucked BBC after BBC. It was finally over when Malcolm was the last black man to get his BBC sucked. He came in my mouth and I was so relieved that it was over.

As I waited to be untied I noticed that Madison was back with Tyrone and she walked up to me. She said, "Tyrone just fucked the shit out of me and came all in my pushy now I need you to lick it out. She put her well-used pussy to my face and I started locking all the cum out of her and she was saying things like yeah eat that black cum you sissy bitch, worship the black man's cum, welcome to your new life as a black cum sissy vacuum and other things. I thought to myself that I couldn't believe how far I have fallen, but at least I was able to eat Madison's pussy. Then she pulled away and said, "At least you are good at eating pussy, I guess it's because you are trying to get all the black cum out of it that you love so much." She then said, "We can't let you go home looking like a mess, hey Tyrone help her clean up." Then the next thing I knew Tyrone was pissing on me and everyone was laughing and teasing. As they untied me Madison said this is only the beginning you sissy faggot! I got up and ran home.

This was my first attempt a a story and I hope you enjoy it.
Please send your feedback to sissyslavejack@gmail.com