Date: Tue, 17 Dec 2013 11:11:48 -0500 From: Charles Anderson Subject: Sissie Bo Alex and David. This story is a story of fiction, based on my real life, names, places and events have been changed in order to protect the willing actors, the story is about a 11 year sissy boy and a 53 year old man. 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. I hope you enjoy the stories. Characters: Alex(is), Little Marissa: 11 year old sissy boy (me) Marissa: Alex's Brazilian mother, divorce and supportive of Alex sexual orientation. Christina: Marissa's best friend and mutual friend of David, also encourage Alex to seduce men, a Sissy boy needs a mature cock. David: 53 year old man who has a boy fetish, and is Marissa's landlord and next door neighbor, friends of Christina. Mr. Parker: Math teacher at Alex school, Friend of David and also one of his lovers. Barry: Online Chart friend – 58 years old has a boy fetish. Part 5. It was 5:30 in the morning when Mom woke me up; I had over slept half an hour. I was in the shower when Mom knocked my door. "Babe you have phone call from David, when can he call you back?" she said, I asked her to tell him to call me in 10 min, I was so happy to hear back from David after one day of silence. After 10 min David called back, I was sitting next to the phone waiting his call like a good sissy boy waiting for his man to call. "Hello David, how are you? Oh I am fine, You missed me? Good to hear! I missed you too, I have to be at the bus stop at right at 6:15 so I am not sure I can go to see you now, Oh you can drop me off at school, ok, let me tell Mom and I will be there in 15 min. I cleared with Mom that it was ok for David to drop me at school, I finished dressing in school uniform, blue shorts, white short-sleeve shirt, blue tie, blue sucks to the knee, I took my book bag and ran to see David. He asked me in and as soon as closed the door he grabbed by the waist and brought me close to him and gave me a very passionate kiss, we must have kissed for a few minutes, his tongue playing with mine, his lips sucking my lips, his hands grabbing my bubble butt, his fingers caressing my butt crack, I was already hard, and I could feel his dick getting bigger and bigger I brought his zipper down and I put my hand inside without saying a word, and I grabbed his delicious cock. I pulled it out and he pushed my head down, so I knelt in front of him and I opened my mouth and started to suck his dick slowly. He was enjoying it, "mmm, Alex I missed your wet warm mouth, mmm how good you are sucking cock, oh yes baby suck it, swallow my cock" as I did what he asked me, he said "I heard Mr. Parker asked you if you want to meet other men?" I took his cock off my mouth and said "Yes David he asked me" and he pushed his cock back inside my mouth. "Ok, I am ok with that, but you have to be careful who you meet, and you will need precautions, not every Daddy out there is good for you baby, and I promised Christina I will take care of you" he said. "MmmmJJJJMmmm, I said still with his cock in my mouth, he just grabbed my face and said "but you are first My boy, and will always take care of my needs first" I took his cock out of my mouth and said "yes David I am your boy first", it did not take long when he said "ready for my load baby? Drink it all..." I opened wide, and he let me have a delicious white creamy thick load of cum. After that he took me to the office as he gathered his papers for whatever business deal he had that day, and then we got on his SUV and we drove to school. "So, David" I said " How do I know who to go with? Do I need to get your approval for seeing another man?" He laughed and said "no, just be careful, get to know him first, if Mr. Parker introduces to one, or if I do that it should be ok, but do not go with the first man who wants to fuck that gorgeous ass of yours." I was glad to hear that, I wanted to make sure I understood our arrangement. He dropped me in front of the school, before leaving his SUV he asked me to give him another Blow Job, so we parked a block away, he unzipped his pants and I put his massive cock in my mouth taking my time to tickle his cock with my tongue, and sucking on the head, I pulled his foreskin all the way back and sucked on the head tasting his pre-cum and enjoying the wonderful smell of cock. I must have sucked him for a good 20 min because we heard the bell ringing from the school just when I was swallowing the last bit of cum. MMmm delicious, so cleaned me up, gave me a kiss in the mouth and sent me to class. During first period, Mr. Parker asked me to come to his desk as the others worked on a math problem, he told me he had discussed with David and I had the green light to meet other men. He said he would arrange for me to meet them at his place, right after school. The rest of the day was uneventful, played with other kids, and was anxious to go home so I could get online and talk to Barry. Just the thought of seeing him cum so much made me horny. I wanted Barry. I got home around 2:15 like I always did, when I got home I found a note from Christina "Honey, I heard about the wonderful weekend you had with David, I thought I give you a gift to celebrate your new Sex life, I know you will look sexy in those, let me know if the size is right, and remember LUBE is the key to good anal sex, I hope you use it and enjoy it...remember what I always told you, your ass baby can drive any man crazy use it well...sissy boys need man cock, and you will always get your way, love Christina!" I ran upstairs and on my bed I box with a pink bow, I opened it, it there was a see through black baby doll, black stockings, a pair of crotch-less panties, garters, and fishnets thigh highs, and a pair of 6 inch heels, with it a little make up case with blush, red lipstick, and other make-up. I was thrilled. I loved to feel all sexy wearing those. Then I noticed there was another bag. In it there were 2 small hipster mini shorts and a couple of t-shirts that showed my belly button, a bottle of shimmery oil, and more lip-gloss. Wow Christina had gone shopping and she had bought me some nice things to wear. I looked at the clock and it was almost 2:30, I had agreed to see Barry online around 2:30 so I took my clothes off, ran into the shower and cleaned myself well, and put baby oil all over my hairless body, my butt looked very delicious, I went to mom's room and took one of her panties. It was red with white dots, small thong style, with wide lace and satin in the front, wide enough to cover my fully erected 3 inch cock. The band came high to my hips and then arched back into my butt crack showing my butt cheeks nicely. I put on a small t-shirts, combed my hair towards my left side, put some lip gloss and turned on my laptop, I placed the laptop on my desk made sure I showed full body if I got up from the chair. I logged into the site, my heart was pounding, then a bunch of alerts showed up on my screen, I had closed to 100 messages from different men, I guess my profile was being viewed by many horny daddies, I also found, requests to connect, I was really exploring the site, I was about to open my some of the notes I had received when I got a message from Barry; "Hello baby", "My cock has been missing that gorgeous body of yours, I cannot wait to see you on cam baby" with that I received a Webcam request, which I accepted immediately. I fixed my hair and prepared to see Barry. "Hello Doll" he said when he saw me..."Hello Sir" I said ...Barry responded "Sir? Please, call me Barry or Daddy, do you want to call me Daddy? My beautiful boy!" I must have blushed there was something about Barry's voice that made me very horny, he could fuck me anytime, I melted every time I heard his voice. I responded "I like the idea of calling you Daddy, you know I don't have a Daddy, and you make me feel so warm inside, I would like that". Barry came on camera, he was totally naked seating on a sofa, the camera showing him full body. He had his massive mushroom head in full view, his cock was so thick and yummy. I liked his looks he was a Daddy type for sure. You could tell he did not work out on regular basis, he had at least a 40-42 inch waist, thick calves, and thighs, nice bubble ass, and broad shoulders, he was tall but I could not gauge exactly his height so I asked " Daddy how tall are you?" He quickly responded" I am 6 feet 3 inches tall, I am 260 pounds, 41 inch waist, and my dick is 8 inches cut baby, do you like Daddy?" with that he got up and walked towards the camera, showing me his cock up close. I was still sitting down at my desk with the camera on my face, I realized my mouth was opened, and I was day dreaming of sucking that cock. Barry said " Baby get up and show me that lovely body of yours, I have been dreaming of that gorgeous body specially your delicious ASS baby, and that cute mouth, I can see you wrapping my cock with your full lips and tasting my cock" I quickly Got up and made sure he could see me and said "Oh Daddy, I would love to suck your cock, and I want to be in your bed, feel your body next to mine, I want you Daddy, since I saw you yesterday I have not stopped thinking of your cock spraying so much cum on your lap and the floor, I want to be with you... when Daddy...when?" Barry was stroking his cock... "Oh baby you are such a beautiful boy, take your shirt off baby, I want to see you just with that sexy panty, take it off now!" Barry was a bit dominant... I loved that..." take it off baby now" So I did, as I took it off he was stroking hard and fast, his purple cock head was expanding even more. "Oh baby...I love your body I want to fuck you so badly, when you ask...if it was for me I would fuck you today baby...but you are at home and I am here, do you think you trust me enough to tell me where you are, I could pick you up and bring you here, we could play, I will respect your wishes if you want me to stop I will, and when we are done I will take you back home, but it is up to you I do not want you to get in trouble with your mom" Barry said. "Oh Daddy I want you so much I do want to go with you, let me call mom and let her know I will be going out and also call a friend to ask her something, and I will give you my address...you can pick me up " I said. Barry interrupted me and said "Give me your address now, so I can tell you in how long I can pick you up" With that said I gave him my address, and we agreed he was going to pick me up in 20 min. We disconnected, and I ran to call Christina... she answered the phone, and I explained to her that I had met a man online, and I wanted to meet him, I explained he has said he would respect my boundaries, and he had also said we would not do anything I did not want to do. She asked me where he lived, and I told her. She said that he must be rich, because that is a very affluent side, then she asked me what I wanted to do. I said I wanted to go, so she said "Call Marisa, tell her you are going to play outside, I will cover for you, I will take Marisa for some drinks after work, just make sure you get back home before 8 pm. Hey wear something sexy for this Man, and remember LUBE is the secret to good Man-Boy sex, take good care of yourself Alex." I got ready put one of the short t-shirts and mini shorts that Christina had given me, I put on a pair of gold sandals, fixed my hair to one side, and looked myself in the mirror, I looked very sexy, m shorts were very sexy and you could see the bottom half of my butt cheeks and you could see where my thong panties buried inside my butt crack. I looked very sexy, I wanted to be as sexy as I could be for Daddy Barry. I looked at the clock and it was 18 min since I had talked to Barry, so I called mom. "Hi Mom, I wanted to let you know I will go out and play in the neighborhood" Marisa responded; "Ok honey, have fun, I will be home late, Christina has invited me out after work, so eat something, don't wait for me, not sure what time I will be home, go see David, I am sure you will like that, make yourself pretty and pay him a visit, I won't come looking for you so if you want to spend the night, just let me know, bye". I put the phone down when I heard a car pull up the drive way... to the door and signal him to wait. He stayed inside the car I picked my keys, and closed the door behind me. Barry was driving a late model Mercedes Benz S Class very nice car with dark Windows. I went to the passenger side and opened the car door. Barry was wearing a t-shit, shorts, and loafers. "Hello beautiful boy "he said... "Hello Daddy" I said... he was checking me out from my toes to my head. "Wow, you are more gorgeous in person than in camera, I must be the luckiest man in the world" "Are we ready?" he said. I said "Yes Daddy I am ready, but I would love a kiss from you before we go" He leaned towards me and was going to give me a kiss on the cheek when I moved my face and opened my mouth inviting him to French kiss me" we kissed for a few minutes, he was a very good kisser, soft tongue and lots of tongue action. When we stopped he said "Mmmmmm, Alex you are a dream of a boy" with that we left my house and drove about 6 min and we were at his home. We lived about 6 streets away from each other. We drove into his drive way, Barry had a large estate, very nice home, he opened the garaged and went in to the house, it was great very discrete. When we went inside his home, Barry took me by the hand and we walked to the second floor. We went into a very large bedroom. His bed was the largest bed I had ever seen; the room had a large sofa, the computer desk to one side. I recognized the sofa from our web cam sessions. His computer was connected to the Webcam site. His house was very large, and nicely decorated. " Do you live all alone in this big house Daddy?" I asked "Yes, my dear boy I do, do you like Daddy's place?" he said. I responded by nodding my head. He then proceeded to take me to the sofa, he said "seat my boy, are you comfortable?, what do you want Daddy to do?" I sat motionless seating in front of him, his pant's zipper at my eye level, I reached with my hand and lowered his zipper and opened his belt, his pants fell on the floor, he cleared them out of the way, I could see through his briefs a very fat bulge, he asked me " Do you want to suck my cock baby?" and he caressed my face and put his thumb on my lips, which I caressed with my tongue and sucked he pull my face up from my chin, and said "Look at me" his was so commanding I shivered in heat. I loved his dominance. I looked up, and he lowered his face and French kissed me, then he said " Lower my briefs and take my cock and suck It slowly baby, take your time, show me how good a cock sucker you are" As he said that I lowered his brief caressing his thighs and calves as I lowered the underwear, when I looked up I saw the massive pink mushroom head ready for me to suck... I dropped on my knees to have a better angle, My had was a bit lowered than his balls... I opened wide and with my tongue I started to caress his shaft and suck on the shaft, going from the outside in, making it wet, and he was guiding my head making sure I was making all of his shaft wet..."mmmm Alex baby that feels so good, are you ready to suck my balls?" as he said that I grabbed his balls and started sucking on them they felt so big inside my mouth I could put only one at the time... he was moaning, "SUCK MY DICK, baby show me what you can do" he commanded, I opened wide and took his massive pink head slowly inside my mouth, caressing it with my tongue, swirling my tongue all over his head, and grabbing the shaft with both hands , I tilted my head backwards like David had taught me, and I slowly allowed his cock to enter my throat, I started to gag and I pulled out a little and sucked on his head to taste his pre-cum and use it as throat lube and again I tilted my head backwards and I pushed in allowing his cock to pass beyond my palate without gagging and his head was tickling the back of my throat..Barry moaned " Ooooohhhh baby this is amazing your throat is so warm, I want to fuck you forever..." as he said that I started to pull and push my head deep in his cock my throat expanding with every push, he was in a frenzy, he grabbed my head deep inside and pushed his dick as deep as he could, I had his balls on my chin, he started to pull out and push in slowly then faster, I needed to breath, he realized that and pulled out, I took a big gulp of air and followed his cock and put it back in this time not as deep, I grabbed his cock with both hands and started sucking going in half way and jerking his cock with my hands, he was spewing pre-cum, it was dripping from my chin, at that moment he pulled his cock and said.. "spit that pre-cum in your and baby" so I obeyed... He took his shirt off and he stood naked in front of me. He said "time to fuck you my boy... come let me seat in the sofa, and I want you to get naked for me...do not wipe that pre-cum from your hand we will use it as lube for that gorgeous ass baby". I started by taking my shirt off, then I started to pull my shorts down. He stopped me and he said he wanted to do it. He began by caressing my legs, then turned me around and sucked on the half of my ass cheeks that were coming out of my shorts. His tongue was all over my ass. He pulled the shorts off and buried his face on my ass caressing my rosebud with his tongue, and then he ordered me to spread his pre-cum on my rosebud. I was in heat, I wanted Barry more than ever, I turned around to face him he was totally naked seating on the edge of the sofa, I was standing in front of him only wearing mom's panties. He had a look that said I want to fuck you now... I pushed him softly so he would lay on the back of the sofa I climb on top of him with my knees on the sofa around his waist, my ass sitting on top of his erected penis, his hard cock parting my crack, my face in front of his face, and I started French kissing him, caressing his shoulder and chest, kissing his neck, going back to French kiss him, he was parting my butt chicks with his hands and placing that massive head right at my sphincter, if he had pushed down on my shoulder his massive head would have entered me easily. But I wanted to eat more cock so I slowly went down on him kissing his check, belly until I drop myself to the floor, and knelt in front of his cock and started to suck him slowly taking most of his cock in...Barry was in only moaning "oh baby you are the best fuck I ever had, never stop baby suck me until I cum" I wanted to taste his cum...but I also wanted for him to fuck me , I wanted Daddy's dick inside me. I must have sucked that delicious daddy cock for a good 20 minutes I really took my time savoring his pre-cum, taking his cock all the way down my throat, socking on his big mushroom head like a lollypop.. he was so relaxed as I sucked his cock. Edging him to almost climax and then climbing on him and letting him taste his cock by French kissing him. But he was ready to fuck me: "Stop" he said "On your knees facing away from me... part your ass with your and rest your head on the carpet, spread those butt chicks as wide as you can I am going to eat your ass and then fuck you boy..." I obeyed..turned around facing the computer and my ass facing him, I got on my knees, rested my head on the carpet, both shoulders touching the carpet, and with both hands I parted my butt cheeks...My rosebud, my fuck hole, my boy's pussy pulsating inviting Barry to fuck it. He got behind me also on his knees , he bended and buried his face in my ass crack, his tongue swirling wildly, spitting on my sweet ass, probing with his finger making me beg for his cock... "Oh Daddy, I love how you eat my ass, and finger me, put more fingers in Daddy, I want you to open me well, so I can take your cock deep in me..." I said. Barry was really enjoying my ass, he would put his tongue in as deep as he could, and the spit in my ass. He would push my back down and he would eat my ass ensuring it was wet and ready for his cock. He then asked me to turn around facing up...he pushed my legs back towards my chest, my knees hitting my chest, he placed a pillow from the sofa on the floor, and placed me at the edge of the pillow. He then pushed my legs backward again he was kneeling in front of me. He had his cock in his hand ready to plow it inside me... but first he lubed and greased me well. Then he lubed his thick man's cock, he pulled me from my thighs closer and pushed my legs back and said " I am going to put my cock in your baby, I will go slow let me know if you need me to stop" With that said I felt my sphincter expanding and big mushroom head went inside me.. I was in terrible pain but at the same time I wanted his cock so badly. " do you like it baby?" he said, I moaned..."mmmmm, YES daddy I can feel your cock inside me, fuck me daddy, fuck me deep, make me your little boy, fuck me all afternoon, fuck me all night if you want to, make me your little girl, your lover" with that he pushed his dick more inside as he pulled on my tits... he pulled me a little closer and I felt his cock get past my second sphincter, it hurt for a little while but the sensation of having his cock in was what I wanted So I started moving up and down he got with the motion and soon he was fully pumping my ass getting his cock as deep as I could take it I could feel his ball crashing on my ass as he pound me. He spread my legs held my ankles and fucked me deep..then he pulled out and with one swift move he picked me up and took me to the bed. He dropped me in the middle of the bed which he climbed and put me on all four legs and started fucking me doggie style, the deeper he got his dick in, the more I wanted him " Oh Barry Daddy fuck me, fuck me hard" I said. He was not talking just pumping my as he was dominating me keeping me on a submissive position head on the bed, shoulder on the bed, ass in the air, he was on top, so he could stick his cock all the way in. He was really enjoying it when he finally cried out " I am coming" at the moment he buried his cock inside me I could feel his cock pulsating feeling my ass with his cum, " I want some in my mouth" I yelled... pulled out still spewing sperm out of his pulsating cock and put his cock right inside my mouth, I had cum dripping from my chin, my nose and I was drowning in cum.. "swallow" he said ...I obeyed him and took a big gulp of cum down my throat, he pulled his cock out of my mouth and put it back inside my ass.. It went in easily my ass was gaping wanting more cock, he continued pomping me and pulling his cock out and putting it back in my mouth and spewing a little more cum every time he did that. He must have gone back and forth about 3 times before his cum stopped. I was drenched in cum, my ass was dripping cum, my mouth was dripping cum, my back had cum, my sides had cum, I turned to him and sat on the bed, took his cock and started cleaning his cock, eating every drop of cum Daddy was giving me. After a few minutes his dick started to go limp. We lay in bed, kissing, and caressing each other. He was a very caring man; he kissed me all over my body, and took my little cock in his mouth and sucked it, I was really enjoying him sucking me, when I looked at the clock and said Oh God it is 7 pm, we had started arrived at his house at 3 pm, and now it was 7 pm. He took me to the bathroom and we bathe, he cleaned me all over making sure to clean my ass well, was we were showering I sucked his cock one more time, he was in heaven, he kept calling me the best fuck he ever had. After we showered I told him I was not in a hurry to get home, that Mom was not expecting me in until late, he said he rather take me home so My mom would not be upset with me. I agreed. We kissed in the car in front of the house, and I pulled his zipper down and had a little taste of his cock, I sucked him to completion I drank all his cum, and headed to bed. Barry pinged me on the site the moment he got home. "you are the best fuck I ever had Alex, when can I see you again"... I told him I would let him know, but I did want to see him again. I was just turning the computer off when the doorbell rang. I ran downstairs, my surprise, It was David. Hello beautiful I said... want to come in? He looked at me and said... "Come to my house and service me before I go to bed. I need a good cocksucker". I could not believe it, It was going to be a long night...