Date: Thu, 06 Feb 2014 17:03:04 -0500 From: Charles Anderson Subject: Sissie Boy Alex and David Part 8 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 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 8. After the wild party of Friday night, Christina and I spent time Saturday morning talking about how to properly conceal my cock when dressed as a girl, we also took time to take care of our skins, we did a facial, and took baths with baby oils and she told me all about how to walk in heels and other secrets about feminization. I was in awe to know that Christina was at one point a man, she is a beautiful woman very sexy with a very large cock that I have no idea how she conceals it so well. For me it will be easy too concealed given the fact I have a small 3 inch cock. We had a very light lunch, a good sissy boy needs to watch his figure, and look as feminine as possible. After lunch, Christina told me she had to do some errands and she was going to be gone most of the afternoon. She asked me if I wanted to go with her, stay home or if I had any plans. I really had no idea what to do in her area. Christina, besides working in the same company as mom also was a make-up artist, and she had a fashion show to work on. The fashion show was near Tampa City Park. I remember that in that area there was a Target store and other shops, and I wanted to go shopping. Mom had given me some money a few days back and I had not spent it. So I told Christina if I could ride with her to the area and that I would go to Target, and then I knew how to take the bus to my house and she could pick me up later that night when the show was over. She loved the idea, and we talked about what to wear for the afternoon. She gave me a pair of shiny electric blue hot pants, they were amazing I put them on, and they were very tight fitting, and very, very short, my butt checks came out from the shorts a little bit but they hugged my butt cheeks nicely. Christina also gave me a sexy hot pink one shoulder t-shirt that came down right above my belly button. She also had bought for me a pair of nice sandals, blue and pink that matched my outfit. She also put a little eye liner, and a glossy coral lipstick, and very light age appropriate make up, that a teenage girl would wear. Christina was very good with the make and it made me look very natural, I looked like a 13 -14 year old girl. She fixed my hair on a single pony tail to one side, and we left for the show. Getting back to Bayshore side takes a good 45 min from Christina's Apartment. We chitchatted about men all the way to near the city park. Christina was running a bit late so she dropped me off a few blocks from the city park and gave me quick directions on how to get to Target from there it was really a straight way to get there. So I took Gandy Blvd and started walking, according to Christina it was a 10 min walk maximum. I had brought along a small backpack purse, with a sweater, my wallet and makeup case. I walked along West Gandy Blvd, I crossed S. Himes ave, and I could see the Shell gas station in the corner, Publix behind it and then Target. It was a sunny day and so I had my sunglasses on, and my headphones on, and I was listening to some classic rock. As I crossed the street and walked through the Shell gas station, I noticed a man filling up a Service Van, he looked in his late 50s, with thick biceps and service uniform. I could not read well what the Van said could be a plumber or electrician, but I have seemed to caught his eye as well as he looked at me as I crossed the gas station and winked at me. I smiled back but did not talked to him and continue walking towards Publix's parking lot. I was about 2/3 through the parking deck when I hear a car approaching right behind me, I moved myself to the left to let the car pass, as the car Passed I see is the same Van that was filling up at the gas station, as he passed next to me he lowered his window and started talking to me which I could not really tell what he was saying because I had my headphones on. I stopped walking and turned to him took my headphones off and said "Sorry I could not hear a word you said Mister, I had my headphones on and music loud" "Hi, I said You are too cute of a little girl, to be walking alone, I saw you back on Gandy Blvd when I was driving towards the gas station, do you need a ride anywhere is hot and not very safe for a girl your age to walk alone, I could take you where ever you are going" "Well, I am going to Target, which is just over there, so I think I am fine, thank you Mister you are very nice" I said. "Hop on I can take you there so you won't melt in this heat" He said as he opened the passenger side door. "No, it is ok I like the heat, and Target is just around the corner, thank you, you are so nice!" I said He insisted "Please let me take you, If something happens to you and I see it in the news I would never forgive myself, I promise I will take you to target and leave you at the door." With that he handed me a grape lollipop, I smiled at him took the candy which it is my favorite candy and I went around the front of the Van and climbed in. I closed the door and he asked me to put my seatbelt on, and he said: "Where are you coming from, I saw you walking almost from Bayshore Blvd, do you leave around here" I said "Actually I was coming from the city park, my friend Christina is doing a Job there and I am going shopping while is working then she will pick me up at my house and I will spend the night with her, because Mom is out of town this weekend and She is taking care of me" "Oh I see" he said, "and what is your name? You are a stunning girl, and I love what you are wearing, you remind me of my daughter, she is about your age, what are you 14-15?" "Thank you, you are so kind, and you are so handsome yourself, you are a strong man, you caught my eye when I crossed the street near the gas station, I am actually 11 years old and my name is Alexis" I said. With that he pulled right in front of Target and said "Well as promised here you are safe and sound, you see I did not kidnap you, even when you are so darn cute and sexy" I opened the door, and turned around and said "It would not been kidnapping, you are hot yourself, I am controlling myself not to throw myself into your arms and kiss you.. hahahaha" With that I got off the Van and turned around and blew him a kiss. He stared at me until I disappeared inside Target. I shopped for about 45 minutes and I was hoping to take a bus line and go to Britton Plaza and go to Marshalls and buy something for Christina as present. I bought some sexy panties, and also a pair of nice jeans and 2 tops. I got out of Target, and started to walk towards the bus stop, when I hear someone in the parking lot yelled "Alexis, do you want a ride?" My surprised it was the same handsome service man who had giving me a mini ride from Publix to Target and obviously was waiting on me. I turn around as I took my pony tail out and quickly ran my hands through my hair and said "Hiiiii, wow were you waiting for me, you are so sweet", as I walked towards the van playing the innocent sexy teen. He said "Not every day a beautiful girl tells this old man that he is handsome, I wanted to talk more with you, so where are you going now?" "Oh you are not old, you are matured, I like mature men, they know what they want and how to get it, I was thinking of going to Briton Plaza and do some more shopping, why? what do you have in YOUR mind?" I said and I seductively put my index finger in my mouth like if I was sucking a lollipop. I could see his eyes growing and as he smiled and winked at me. "Do you want me to take you where you going?" he said. "Sure, or You can take me where YOU Want to take me" I said passing my tongue by my lips, I was in full seduction mode, I wanted this man, and I was scared but very excited, I was about to pick up my first blue collar worker, just the thought of his bulging arms made my little cock excited. He opened the van's passenger side door and said "get in". I walked slowly around the van looking at him directly at his eyes. I climbed in the van, closed the door and put my seatbelt on. "Let's go" I said. He accelerated the van and we got into W Gandy Blvd. His van had a bench rather than bucket seats, so I got near him and said "God you are handsome, strong, and smell so nice, what is your name?" He smiled and said "I am Stewart, you are pretty forward aren't you little girl?, So let me be forward too, what DO YOU want to happen here?" I got closer to him and put my hand near his crotch and said, "you wanted me since we locked eyes while crossing the street near the gas station, or maybe even before when you saw me walking along Gandy Blvd. So, tell me, what do you like about me? and what do you want to do with me?" as I said that my hand was caressing his thigh, going from the outside to the inside towards his crotch. He had also placed his right hand on my legs and was caressing my inner thighs. "Well, you got me! yes I saw you on Gandy blvd, I loved your legs and how you moved your ass as you walked, those shorts make your ass look amazingly hot, and then I saw your beautiful face, and I got even more excited. But I have never picked a minor before, I have a daughter your age, but you are so fucking hot and that ass of yours was tempting, so you ask what I want to do with you, well I want to fuck you, but I am no rapist, or a freak that hunt young girls, so anything that happens should be what YOU want as well" He said. I continued to move my hand toward his crotch as I felt a cock a few inches down his crotch on his right inner thigh, when I passed my hand he moaned, "Oh baby don't tease me" We were still driving on Gandy Blvd, passed the exchange to the Selmon Expressway, When I said "what will you do if I tell you, I have been with older men before?" "You are not a virgin at 11? Wow, Who fucked you, your teacher? "No, another Older Man" I said as I continue to caress his cock "oh my, is that why you are dressed like this to attract men, are you a hooker?" he asked "No I am not a hooker, and I do like to dress like a girl from time to time" I said waiting for his reaction. "Oh Ok, so what do you want to do, do you want to suck my dick here in the truck? or do you want us to get a room?" he said ignoring completely the fact I had just told him I was not a girl in so many words. "I don't feel comfortable doing anything in public, a room would be best" as I said that we were passing an Inn, Stewart just made a quick U turn and pulled into la Quinta Inn. He asked me to stay in the Van, as he went inside the registration office and 10 min later he had a pair of card keys on his hand. He said let's go and pick some supplies before we go to the room, we left the Inn and ½ a block we got into a drugstore he picked lube, and condoms, and also some beer, and we headed to the room. We parked right outside the building where the room was, we came thru the side door and took the stairs up to the second floor, I walked ahead of him, and I could feel his eyes fixated in my ass. When we got to the last step I turned around and said "I think you are going to enjoy fucking my ass" and took his hand and planted it right in between my butt cheeks his fingers landing right at the crack. I looked down at his pants and his cock was hard as a rock and I could see the bulge through his pants. We got to room 204, he opened the door, and asked me in the room, I walked in and went directly to the window and closed the curtains, and turned up the air. He came behind me and I turned around. Me at 4ft 7 my head was to his chest, he was at least 6ft 1inch tall, arms of steal. I thought about the fact he thought I was a girl, and I feared that he would get angry at me when he found out I didn't have a pussy. He hugged me and put both hands on my ass and parted it as he pulled me close and bent down to kiss me. I had to tell him I was boy before we kissed. I put one hand on his crotch and I squeezed his cock, and the other hand I put it in between his mouth and mine, and said. "Before you kiss me, you have to know, I am not an 11 year girl, I am an 11 year old sissy boy, I don't have a pussy, I have a 3 inch cock, I love mature men, and I like to please them, if you do not want me after knowing that I am ok, I will pay you for the room, and you can leave" "he looked at me lowered my hand that was in between our mouths and pulled me closer and kissed me, he was in heat, he did not say anything just French kissed me and squeezed my ass. He started kissing my neck and all of a sudden he picked me up and carried me to the bed. He put me gently on the bed facing down, with my face towards the edge of the bed, he took his shirt off and undo his pants and they fell to the floor, he pulled his boxer shorts off and showed me his 9 inch cock uncut. It was not extremely thick but it was a good size to grab with my 11 year hands. The foreskin pulled back all the way and the head was very white, not matching his obviously tanned body. He stood right in front me and said "Suck it little girl, show me how you please men" I took his cock and slowly started licking his shaft and balls and moved to the head and with both hands I pulled the foreskin back on top of the head and then grabbed the shaft and moved him closer to my mouth as he entered my mouth I pushed back the foreskin as I sucked the head and also flickered my tongue as he penetrated my mouth all 9 inches making me gag at first. He bent over and started to caress my legs as he pumped my mouth. "Oh fuck yeah little girl, suck me, o fuck yeah, hmmmmmrrrr yeah oh fuck, eat my cock little whore, you bitch, you love cock don't you, you do, you love seducing men like me that don't get sex at home, so now eat my cock all of it, eat it you little bitch", as he said that he started spanking my ass, Oh!!! the pain, every slap on my ass was done stronger, he was mad, yes he was mad I seduced him as a girl, and I am a boy... he continued pumping his cock inside my mouth, my mouth was overflowing with precum, his cock was wet and slimy, he was grabbing my head now and pumping hard making sure I could not move, he was dominant and I was excited, afraid and Horny. He fucked my face for a while, as he continued with the verbal abuse... "You little whore, I will fuck that ass, until you beg me to stop, and then I will make you eat my cum... you little tease, bitch that moved that ass for me to see it and I could get horny and seduced me, I fell for it, so now I will fuck you until you beg me to stop" He had me on a face lock he was putting all 9 inches down my throat, and keeping it inside until I could not breath, and then he would pull out so I could breath. When he pulled his cock out he said "Spit all the precum on my cock" So I did. He ordered me to strip... he picked me up from the bed and put me on the floor standing in front of the bed. He said "Strip, take your shirt first, slowly" So I did... he pulled me closer and started to kiss me again, and started to kiss my neck and then lowered himself to suck on my puffy nipples... then he unbuttoned my shorts and lowered them, he turned me around and lowered my panties, exposing my bubble ass. He pulled me closer and started sucking my butt cheeks and parting my ass, and then he started fingering my ass and rimming my ass... "God you are beautiful little girl, I may just found the best fuck in Tampa" he said. With that said he accommodated himself on the bed, he sat at the edge, spread his legs, he took some lube and with two fingers he lubed my ass, putting first 2 fingers in and then 3 then 4 my ass felt so good with his fingers in, then he lubed his cock, head and shaft, then he asked me to slowly lower myself and seat on his cock. He guided me slowly and made sure the head was penetrating me, and then he put his arm around my waist and pushed me down ramming all 9 inches inside of me! It hurt so much at first I moan with pain..."Oh god god god...oh yes yes" "Oh Fuck baby your ass is so tight, what a perfect ass you have baby, I will fuck you good, I will fuck you until you had so much cock inside you, you will beg me to stop, and I won't until I fill your hole with cum...Oh baby your ass is perfect for a day long fucking" he said Once my ass was used to his cock inside me, I started moving myself up and down and side to side to give him maximum pleasure, we slowly moved inside the bed, he was laying on his back and I was laying on top of him, my back to his chest, he grabbed me from behind my knees and pulled my legs towards him, my boy pussy fully visible in the full size mirror in front of the bed and he started pumping my ass, first slowly, then fast and faster... I started moaning... "oohhh ohhhh ohhh ohhh, yessss yess yess Stewart fuck me daddy, fuck me, fuck me hard, oh I love your cock inside my ass, fuck me daddy, fuck me hard harder harder" I was getting an amazing fucking this blue collar worker was starving for sex and I was getting all his wrath... I continued moving my hips side to side and up and down I pulled myself up with my arms to allow his cock to go in all the way to his balls, I could feel his cock expanding with every pump, I thought he was going to cum faster than I wanted to, so I pulled him out of me... He was moaning and grunting I turned around and sat on his cock my chest to his chest I grabbed his cock and put on my crack and I grabbed his hands and I lowered my face to his face and kissed him with all my passion he was humping my crack as he kissed me he let go of my hands and started parting my ass and looking for my boy pussy, he found it and put his cock back in, and put his arms around my waist and started pumping me. "Grab your ass and open it wide" So with both hands I reached for my ass and opened my ass chicks as he continued fucking me... "Oh daddy yes stewart, make me your girl, I want you inside me baby all the way, fuck me, Stewart fuck me, make me ask for more... give me all your cum" I said. He was about to cum so he pulled out... fast and I rolled to the side of the bed and put myself in all 4s knees and elbows touching the bed head on resting on the pillow my hands opening my but cheeks... "Stewart, come fuck me baby, give me more, I want to feel you inside me, give me more baby, I want you in me..." I said. Stewart stood on the bed with me under his legs and he spat on my boy pussy he put more lube on his cock and lowered himself, mounting me from the back, and lowering his torso so he was also on all fours, with me under him and he pushed his cock ball deep inside me... "Ohhh fuck, fuck me baby, fuck me hard Stewart" I said "Oh baby your ass is so good so tight, squeeze it baby, squeeze my cock with your ass as I fuck you baby, I want to give you my cum baby" he said " I want your cumm in my mouth baby, oh yeah, like that, fuck me like that, yes, yes, yes, there fuck me harder...mmmm, deep baby ,I am you brazilian whore, fuck me baby, you can fuck me whenever you want..., fuck me please, more, more, yes, yes, fuck me baby..." The more I asked him to fuck me the faster and deeper he penetrated my boy pussy, I was on fire I wanted to have his cum...now He pulled his cock, and asked me to open my mouth, and suck his cock... "oh yes baby suck it oh yes baby gooooooood mmmmmmmmm yessss suck it stroke it baby, and suck on the head I want you to eat my cum baby..." with that he screamed "I am coming" I felt his cock expand on my hands and inside my mouth the head expanded, and then I felt a gush of cum, so much white thick cum, I had my mouth full of it, he sprayed my face, my nose, he was still cumming he ordered me to show him the cum in my mouth and then Swallow, which I did, then he turned me around and he rammed his cock deep inside and gave me another round of cum.. I had cum dripping from my ass, my mouth, my hair, my face. He pushed me to the bed, and got on top of me and started kissing me, tasting his on cum, we passed cum back and forth between our mouths playing with the tongues. He knelt on the bed and spread my legs, and started sucking them, kissing them, until he got to my cock, which he took on his mouth and started sucking it. My 3 inch dicky was so hard; I started to feel like something was going to come out of it! He was sucking it hard. He then spread my legs again and rammed his cock inside my ass and continued fucking me until he gave me another gush of cum... once he took his cock out, I looked at him and said "thank you for fucking me daddy" He was exhausted he collapsed on the bed...I followed next to him. We must have slept for about an hour, I woke up when I felt something getting inside my ass; He was fingering me as I slept. "Hi, we fell asleep" I said, he said "yes baby we did, wow I cannot believe you took my cock without any problems, you like fucking men don't you?" I asked him if he was angry at me for making him believe I was a girl, he looked me in the eye and said "I was not angry only surprised that boy would be so feminine and fucking hot, that ass and legs of yours I am sure are the envy of 16 year old girls in Tampa, I never thought that I would ever be with another man worst a boy, but I had to fuck that ass, and kiss your lips, you are the most beautiful boy I have ever seen, and I loved fucking you" I smiled, he kissed me, we caressed each other for a while I held his dick on my hand and gently stroked him as we kissed some more, he wanted to fuck me one more time but I looked at the time and it was close to 6 pm. Christina would be looking for me in less than half hour. And I was still in bed with a man. I explained that I had to get home, and he gave me his phone number, and we prepared for him to take me home, during the drive home I told him part of my story, how We had come from Brazil, how mom encourage me to be the sissy boy that I am, how she supported that I have sex with mature men, she knew that would make me happy and that is all she wants that I am Happy. I also told him that I wanted to see him again, and he could call me my cell phone anytime he wanted to. He was very happy to hear this. By the time we got home, Christina had not arrived yet, Stewart's van pulled in the driveway, but before I got off his van, I mounted him and we French kissed, he pulled my shorts down and fingered my ass, he loved my ass, he asked me if anyone could see us, I told him, that David my Neighbor was out of town, and there was no one in the house in front. I invited him in, but he felt uncomfortable. So we continued making out and him fingering my ass, I stroked his cock with my hand for a good 10 min. I got off the van, and reminded him to call me after 3 pm weekdays, and told him, I wanted to see him again soon. He drove off as Christina arrived to me pick me up. She saw me at the door, and from the car she asked me, "was anything wrong with the Cable? I just saw a Cable service van drive away..." I said "no, all ok he was looking for an address and I flirted a little" "Oh Alex, you are not ready for blue collar cock yet..." she said as she patted my ass. If she knew the fucking I had received from that man, she would be jealous.