Date: Mon, 24 Feb 2014 16:33:55 -0500 From: Charles Anderson Subject: Sissie boy Alex and David 9 These stories are fiction, they are based on my real life events that occurred back in the 1990s, names, places, timeline and events have been altered in order to protect the actors, the story is about an 11 year sissy boy and his sexual adventures . If that idea does not turn you on, or if it is illegal in your area, then you do not need to read further. If you are under 18 please leave the site. Characters: Alex(is), Little Marissa; 11 year old sissy boy(me) - 4 feet 7 inches, 82 lbs, 32 chest, 25 inch waist, 34 inch hips, long straight blond hair to my shoulders, and a butt cheeks that most girls would envy, and very hairless body, totally smooth tanned skin. Marissa: Alex's Brazilian mother, divorce and supportive of Alex sexual orientation – a cross between Salma Hayak and Kin Kardasian. Alex inherited her looks. Christina: Marissa's best friend and mutual friend of David, also encourage Alex to seduce men, a Sissy boy needs a mature cock, Christina is a Pre-Op transsexual! Stewart: Service Man – Drives a White Service Van Bruce: Marisa's Boyfriend David: 53 year old man who has a boy fetish, and is Marissa's landlord and next door neighbor, friends of Christina. Story takes place in Florida in the late 2000s. Part 9 The weekend got interrupted with Mom coming back from her trip a bit early due to bad weather in Key West. I got to spend time with Christina and learned a lot about feminization and how tease men, she also taught me the proper way to deep throat, I practiced on her after we left my house, and went back to her apartment. She was very good teacher showing me how to control the gag reflex and showing me how to open my throat by sticking out my tongue as far as I could and how to caress the balls with the tip of tongue as I got a cock all the way down my throat, also she remind me to breath deep before getting the cock down my throat and how to hold it in. Christina was extremely sexy, she had beautiful C cups breast not to big not to small, and she had, a tiny natural waist, and a nice round Latin booty. I asked her when she found out I was a sissy boy, and how mom had taken the news about her being a tranny. According to Christina mom new from the beginning that Christina was a Tranny. When they first met it was a through a common friend in a party. Christina had been attracted to mom, and she made a move, mom told her she was not interested in Women, and Christina told her she had a cock. Mom that night got a bit drunk, and end up in bed with Christina, So Chris had fucked mom, and that is how they became such good friends, now it all made sense why Christina would stay with mom overnight, she kept mom sexually satisfied and without commitments. Mom told Christina from the beginning that I had very strong girlish tendencies and that she thought I was going turn out to be a sissy boy. She also asked Christina to help me. Christina told mom, the only way a sissy boy is happy is by having men cocks up their asses and inside their mouths, and that sissy boys preferred men, not other boys. Mom agreed that Christina was going to guide me to become a true sissy boy and find happiness. It was good to know why Christina had from the very beginning given me fem clothing, I was like her little project. I did like to wear fem clothing but I also like to be a boy. I found out in these few weeks that I had become active that not all men like boys dressed like girls, some like boys to look like boys. I was fortunate that could pass for a girl or a boy depending on how I fixed my hair or if I wore make up or not. Being in Florida wearing tiny shorts and little clothing was the norm. Boys wore longer shorts than I did but most men who liked boys like a nice round booty and that I had and I could always show. Like I said earlier Mom came back early from her trip to Key West, she joined us in Christina's condo and we spent the night there, we had a typical day with mom and Christina, we took care of our skin, we did our nails and talked about mom's trip. She told us about her new boyfriend, I still had not met him, I started to wonder if mom, was hiding him from me, was I a threat? I would never go after Mom's man. So I asked. "Mom, when are we going to meet your new boyfriend?" Mom seemed uncomfortable with the question..."Well baby I will bring him over when I think is appropriate, right now we are just getting to know each other and I am not ready to bring him home" she said. Christina said.. "Do you think he would like us? I mean does he know that Alex ... well you know what I am asking" Mom, smiled and said "I have been totally honest with him, I have told him my best friend is a transsexual and my boy is sweet, and he is ok with that, he is eager to meet both of you, I am just taking my time" Mom said. Christina smiled and caressed me and said you see my baby Alex everyone wants to meet you baby". With that we headed out for some shopping and then we had plans to get home, the long weekend had gotten shorten for me. With mom at home I had little chance of getting out and do some teasing or getting some cock. I knew David was out of town until the following week, man I missed David, his wonderful smell, and his delicious cock, just thinking of him my cock gets all hard and the taste of his cock is so vivid inside my mouth. Mom, Christina and I got dressed and we headed out for the mall, I wore a pair of jean white mini shorts, white sandals and a white t-shirt, and I got my hair on a pony tail and wore a white baseball cap. We drove to a mall near our house and spent some good quality time shopping, I bought mostly panties, and some boy clothes and a couple of teasing shorts and leggings. Mom, thought I should dress as boy when I meat her boyfriend so we also bought a couple of boy shirts. Mom wanted to go and buy some lingerie and Christina and I headed out to the back of the mall to a pharmacy, where she bought me a couple of tubes of lube and she also bought me some light make up. While at the pharmacy I got a couple of texts by Stewart my blue collar man. Stu Martin (2:31 PM) – Hi baby just trying out messaging you, please let me know if you get this! Stu Martin (2:33 PM) – Are you there baby? I am hard thinking of your ass baby, when can I fuck you again, yesterday was the best fuck I had in years, I want to fuck you soon, I hope you are well, please let me know if you get this! I was so excited, I usually do not receive texts my cell phone had very little texting capabilities so I replied quickly! "Call me, you have my number" Within seconds my phone rang! "hello" I said "Alex? This is Stewart how are you baby? Is it a good time to talk?" "yes, hi how are you, I got your texts but I am not good texting, and my phone has limited capabilities, my mom is buying me a new one soon that has text and email and all that called Blackberry, so it is better to call, if I answer is that I can talk, so how are you?" I said "Oh Alex, since I dropped you off at home yesterday afternoon I cannot stop thinking of how good it felt to fuck you, when can I see you again, I cannot believe that you are a boy, when I first saw you on the boulevard I was sure you were a girl, but that ass of yours is too good to pass up, I don't care that you have a cock, it was kind of exciting to fuck a boy, so when can I see you?" he said "well, mom came back earlier from her trip, and I am out with her at this moment, is there a way to contact you if I have an opportunity?" I said He told me to text him and he would call me back as soon as he could, so we agreed on that. Christina, was nearby and was questioning me with her look, I winked at her and said "Yesterday's Service Van guy, wants some of this" and I padded my ass! Christina said "wow, you are an insatiable sissy boy my dear." We met Mom at the food court, we had lunch and then we headed home. Christina left and Mom took a nap. I decided to catch up with my homework and then go for a bike ride around the neighborhood. I finished homework around 4:30 pm and I put on spandex shorts, and took my bike to the park, I left a note to mom that I was out biking around the neighborhood and would be back before dinner. Before I left the house, I texted Stewart and waited for his call down the street from home. I stopped at the corner of my street and Swann Ave. to wait for Stewart's called, He called me within 2 min of my text. "Alex, where are you?" he said "I am on my bike, on Swann Ave, I am heading to Old Village Shopping Center do you know where that is?" I said "Yes, I am actually not that far from you babe, I am doing installations all this week at the Hyde Park Hotel, I can be there in 15 min, how fast can you be there?" he said "I can be there in 5 min, I will wait for you at Swann and S. Dakota You cannot miss me I will be there with my bike, do you want me to park my bike there? Or does it fit in your Van?" I said. "Leave it there, on my way see you soon baby" he said My heart started pounding it was almost 5 pm and I had to be home by 7 pm, I was hoping we had time to do something. I got the Old Village Shopping Center within a few minutes. I found a bike rack and tied my bike to it and sat at a near bench, where I could see the corner of Swann and Dakota. Within 2 minutes I saw the Service Van at the corner, I quickly got up from the bench and approached the corner, Stewart signaled me to wait where I was he made a right turn into S. Dakota and stopped right in front of me, I opened the passenger door and jumped in the van. Stewart was already hard, his big dick was making a big bulge on his crotch, my eyes were fixed on it. He closed the tinted windows on both passenger side and driver side and he reached for my head pulling me towards him, and he kissed me passionately, then he opened the zipper on his working overalls and pulled out his cock, and he guided my head straight for it, I could smell his cock, smelled like a man, the type of smell a sissy boy goes crazy for, I was trembling with desired, I wanted to taste that cock, he started to drive away, and said " suck me while I drive babe" I did, I took his cock with both of my hands and slowly started sucking I got down on the floor of the passenger side to have better access to his cock, from that position no one could tell I was down there sucking this blue collar worker. He was moaning in delight, I could see how excited he was by amount of pre-cum he was producing. I was really loving this, the danger of moving through traffic as I sucked him made my boy hole itch, I wanted this to never end, I was socking the head and pumping the shaft with both hands, I would stop and suck on the balls, we drove about 15 min until he pulled up into the back of building. He stopped the Van, and asked me to seat on the bench, I did. He reached for me and started to kiss me, first my mouth, then my neck, he took my t-shirt off my, and kissed and liked my chest stopping at my titties , and sucking and gently biting my nipples, I he was driving me insanely hot. Then he started sucking on my belly button, pulled down my shorts and exposed my small cock , he continue sucking belly button as his hands fondled my ass...he loved my ass, he buried his face on my crotch and started to suck on my small cock, taking balls and cock at the same time, and putting a finger or two inside my boy hole. I guess he was going to fuck me in the Van! He continued to suck on my cock and fingering my ass, he was now putting 2 – 3 fingers inside, it felt so good as he sucked me. When he stopped and said," I am working on this hotel renovation and I have access to a few rooms, do you want to go inside?" He pulled up m shorts, and handed me my shirt and took me by the hand and we got off the Van, we went inside the back of the building and he picked the first room to the left. The rooms were all finished but the electricity and other details were not installed yet. But in it there 2 beds, your standard double occupancy hotel room. He locked the door, closed the curtain picked me up and put me on the bed, he then with a fast move flip me over so I was facing down the bed, he pulled my shirt and shorts off, I was now totally naked laying on the bed, he grabbed two pillows and put them gently between the bed and my crotch to raise my ass up, he spread my legs and bent them in, so I would have my cracked completely exposed. He then took his working overall and underwear off, and he stood naked behind me jerking his cock to ensure a very hard and stiff cock before he buried it inside my ass. "Alex, I love watching your ass baby, do you want my cock as much as my cock wants your ass baby?" he said with his manly voice. I was fucking horny I wanted that cock inside me, my mouth wanted it, my ass wanted it, my hands wanted it, I wanted to feel him on top of me, dominating me, making me his boy slut, "Oh Stewart I want you so bad I am feverish with desire for your cock, your mouth, your body on top of me, I love when you dominate me and fuck me hard like yesterday" He lowered his face and buried it in my ass crack, he rimmed me, making my ass wet, he tongue fucked me putting it deep inside me ( I was so glad I had done my cleaning ritual before leaving home), he was loving my ass, spanking me at the same time he was eating it, my ass was so wet, I did not need any lube, he spat on his cock and he asked me to grab his cock and guide it into my rose bud, I took his cock with my right hand, it was so big my hand barely covered the total circumference of his cock and placed the head right at my ass, and he grabbed both of my wrist and pulled me closer to him as he thrusted his cock deep inside me...Ohhhh I knew it was going to hurt at first but them the pleasure, he did not stop pushing in until all of his cock had disappeared inside my ass. He then grabbed my hips, and got on the bed on his knees, and started pumping me as he also slapped my ass with every thrust. "Ay Ay Ay yes fuck me, fuck me , fuck me , Ah Ah Ah Ah Ah yes yes deeper deeper, mmmmm yes make me your boy, I want you Stewart, fuck me" I moaned in pleasure "Call me Daddy boy slut, I own your ass little fucker, I will fuck you today until you beg me to stop" he said "oh Daddy Daddy fuck me Daddy, yes give me that cock, I want you to cum inside me, in my mouth, I want to taste your cum Daddy...Ah Ah Ah Ah yes fuck me fuck me fuck me..." I moaned He was so now pushing my back with one hand and lifting my legs together I was kneeling on the bed with my ass in the air my head and shoulders on the bed He was standing on the bed and burying his massive cock deep inside me as he pushed in and pulled out he would spit my hole to add more lubrication, he was truly banging me hard, I had both hands parting my ass so he could put his dick all the way in...he fucked me for that way for about 10 min, then he pulled out and stood up on the bed.. and he ordered me to get on my knees and suck his cock... "Come here boy slut, suck my cock, taste that delicious ass of yours, and make me cum" he said, I did as told. I knelt in front of his cock took it with both hands , inserted the head inside my mouth, and I started to deep throat him like Christina had shown me..."OH FUCK BABY you are so fucking good cock sucker...mmmm" as he said that he grabbed my head and pushed his cock even deeper, I could feel it expanding my throat, I did not have time to gag, he was way inside down my throat, he started to sway back and forth and started to face fuck me, with every pull I had a chance to breath, and then he would push his cock down my throat and keep me there for a few seconds, and pull out. He was really loving it, I was too... "FUCK ALEX I COULD FUCK YOU ALL DAY LONG YOU LITTLE SLUT" he was yelling what I thought as anger last time now I know is passion ...he is a loud lover.. .he then took his cock out and started slapping me with his cock on my face, here little slut feel my cock.. I grabbed it with to hands... and started to suck it as hard as fast as I could, he was face fucking me hard, and then... He Yelled "FUCK ALEX I AM CUMING" and I wrapped my lips around his cock and pumped It with my hands as I felt the warmth of his cum hitting the ceiling in my mouth and filling my mouth a huge load, he pulled his cock out of my mouth and cum was still gushing from his cock, he continue jerking his cock he asked me to get on the floor on my knees, head on the floor and he buried his cock 6 times on my ass as he continued coming, I had swallowed most of the cum, but I still had some on my face, once he had finished cuming he slapped my ass and with one foot pushed me down to the floor where he got on top of me and forced his cock down my throat.. "taste your ass baby and my cum.. this is what you will get every time we meet, you like?" I nodded yes as well as I could he had his on my crack and pushing his fist in, I started to panic, I was scared... he realized that and he ease up on the fisting, he took his cock out of my mouth, put on the bed got next to me and started to kiss me... we rolled in bed kissing furiously , he was liking all of my body, and sucking it he took my cock in his mouth and sucked me, I was sooo fucking hot I felt a spasm and I trembled and I felt feverish and then I exploded in his mouth.. My first CUM... I had finally cum... He swallowed it and looked at me ... "WELCOME TO MANHOOD" he said, I was twitching, I felt feverish and tingly all other my cock was sensitive I could not even touch it... We lay in bed for a few minutes, he brought a wet towel and cleaned me up.. asked me to get dress he sat there naked with his cock still hard looking at me dressing, when I was done he brought me to the bed he was sitting on the bed with his legs open I was standing in front of him, he brought me closer, he had both hands on my ass and asked..." Well do you want to see me again?, do you like rough sex, or do you want me to be more tender?" I said ... yes Daddy I love how you fuck me, even though you do scare me sometimes. But I enjoy 99% of it. When can I see you again, when can you fuck me again" "Ohh now you are asking me to fuck you!!! You have my number you call me when you want that ass filled with cum" "Thank you mister... Daddy...Stewart...for fucking me..." "You are welcome my little slut son" Stewart took me back to the Shopping center and I got off the van, my ass was really hurting he had fucked me really hard and I was a bit in pain, I walked my bike home. When I got home I found a note from Mom " I decided to bring Bruce home tonight, shower and put whatever you want to wear, I want you to look beautiful even though, I am sure Bruce will love you no matter how you look" MOM I ran upstairs and took a shower; I decided to wear a pair of tight yoga Capri pants, a pair of sandals and short tank top. I used the flat iron and straighten my hair. I put some soft perfume and went into the family room and wait for mom and Bruce. 15 min later Mom arrived with Bruce...he was a very masculine man, 6ft5 well built, about 260lbs, in his 50s, he was wearing a nice pair of designer jeans and white shirt, nice shoes.. very large shoes!!! We had our introductions, we chitchatted and then we had dinner... he was very nice with Mom, After dinner we sat in the sofa and watched a movie, Mom and Bruce were cuddling and I was sitting next to Bruce but not very near, movie was great but I was tired, I started to feel sleepy, Bruce noticed and with one arm he pulled me closer to him and said "Come her Alex rest on my chest, I am not going to bite you" I looked at mom and she nodded... I lay my head on his chest and I closed my eyes, it felt nice, his hand was resting on my hip, as he started to caress it and moved down to my back and grabbed my bum...I fell asleep... Please send me feedback at CharlesAnderson1980@mail.com