Bobby Becomes Pussy, The Babysitter free porn video

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Bobby Becomes Pussy, the Babysitter Part I By Tammie Latte "Bobby, how would you like a job working as a babysitter for a week or two?" my mom asked as I entered the kitchen wondering what kind of cereal I was going to have for breakfast. "Aunt Julie has a friend who has to go away unexpectedly on business and needs someone reliable to watch her little boy until she returns. It pays big bucks and Aunt Julie is willing to help out whenever she can. The job is yours if you want it," she added. I was getting terribly bored with summer vacation and I really needed the cash, so I quickly accepted the offer. Mom was amazed I agreed with so little coaxing, but to me it was no big deal as long as Aunt Julie would be there for me if I needed help. After breakfast, Mom called Aunt Julie to tell her I was interested in the job. Aunt Julie was glad, but she wanted us to leave soon because her friend, Ashley, needed me right away. Although she wouldn't be leaving for a few days, there were lots to do before I took over as babysitter. It didn't take us long to pack my bags and be on our way. The two hour ride to Aunt Julie's was lots of fun. Mom told me about some interesting babysitting experiences she had when she was my age. Some of her stories were outrageous because, as a teenage babysitter, she was always getting into trouble for entertaining her boyfriends after the parents left the house. She said some of the dads would even hit on her while driving her home, and that she lost a few jobs because their wives became suspicious. Such revelations didn't shock me one bit. My mom's very sexy and loves to tease - she even kidded me about having plans of my own to entertain boys at Ashley's house. "That's probably why you're so eager to take this job, isn't it?" she said. "I bet you're planning to show all the boys in Aunt Julie's town a good time and you're using this babysitting job as an excuse to meet new guys." "Mother, don't even say such things," I retorted nervously, knowing she was half serious. Mom had every reason to tease me because she had recently caught me in her clothes acting like a slut. She get home early from work a few weeks ago and caught me videotaping myself in a hobble skirt. I was so horrified that my mom caught me prancing around her bedroom in a platinum blond wig, five inch heels and a dress reminiscent of Marilyn Monroe's birthday song gown that I locked myself in her bathroom, vowing to never EVER come out again. I was totally humiliated and told Mom it was the first time I had done such a thing and promised never to do it again. Of course she new I was lying when she made me show her the entire videotape, revealing the truth: that I have been crossdressing for years and that I am a sissy fag. I have been videotaping myself en femme since Mom got me a camcorder for my twelfth birthday three years ago. Fortunately, Mom was very understanding and even expressed a desire to support me in my efforts to further explore my feminine side. She said she thought I looked really cute and that I could wear any of her things whenever I wanted. Since I was petite for my age, I could easily pass for a teenage girl or even a young woman in her early twenties. And then there was last weekend. Mom insisted I help her clean house dressed like a girl. She put my hair up in a pony tale and held it in place high in the back of my head with a pink skrunchie. I wore pink lace panties under a pair of short cutoffs that zipped up the side. I was pleased how the outfit highlighted my pretty round ass. Mom gave me a set of falsies to wear under the cute floral halter top she selected to show off my tiny waist and unusually unmuscular arms, neck and shoulders. Mom applied a little bit of pink lipstick to highlight my pouty lips. "You really are a doll, Pussy", Mom remarked as she put the tube of lipstick back into her purse. "Why don't we get you all dressed up tomorrow and take you out in public for fun. I'm sure no one will ever suspect you're a boy." I'm sure Mom meant well by suggesting this, but I turned down the offer. I told her I was afraid people would recognize me and think I was a pervert. She told me I shouldn't care so much what other people think, and that I would ultimately have to get over such silly inhibitions if I ever wanted to enjoy the pleasures of womanhood. That's when she started calling me "Pussy". Mom likes to tease me; I guess it's her way of getting me to lighten up. I did, however, enjoy doing the housework dressed up like Mom's teenage daughter and loved the new relationship I was forming with her. I especially loved engaging in girl talk because I could share things with her I never could before. Fashion and glamour weren't the only things we talked about. We also discussed relationships and Mom's sexual exploits as a teenager. I told Mom I was attracted to several boys in my class and that when I see sexy pictures of women in magazines, or see them on TV or in videos, I'm envious of them. I want to wear their clothes, to walk and talk like them. I want to BE them, and not the boring teenage boy that I am. Mom was very understanding and, in turn, told me some secrets about herself and my dad, who was killed in a car crash when I was ten. Dad and Mom were swingers and each enjoyed having wild sex with multiple partners of both sexes. My Mom loved getting ganged banged, but my dad loved it even more. I was happy to hear that my dad was also a very attractive cross dresser who loved sucking cock and taking it up the ass like a slut-bitch-faggot-whore. Mom said Dad was very popular and always a big hit at parties. I'm so glad I learned the truth about my parents. Perhaps my fondness of women's clothing and my interest in boys are purely genetic and just a natural part of who I am. When we arrived, we were warmly greeted by Aunt Julie. As usual, she hugged and kissed us both, then led us by the hand into the living room to chat. "I'm so happy you can help my friend Ashley out, Pussy. She really needs your help," my aunt said. When I heard her use of the nickname, Pussy, I gave my mom a stern look. "It's okay, Pussy," my mom reassured me. "Aunt Julie knows all about your crossdressing and has no problem with it. In fact, that's why she thought you would be the ideal candidate for this babysitting job." That's right, Pussy," she added. "Ashley's little boy, Billy, feels very uncomfortable with male babysitters. Since there are no girls in the neighborhood mature enough to do the job, we all agreed you could dress up like a girl and Billy wouldn't know the difference. You'd be doing Ashley a huge favor." "But Auntie," I protested. "I didn't want anyone to know about my crossdressing. It's personal!" "Nonsense," she replied. "Why should anyone care. You're not into something weird like sports or violent video games. Besides the only people who will know about it are your mom and I, my friend Ashley and her husband Brian." "Her husband Brian! No one ever said anything about a husband!" I objected. "Relax. You won't even know he's there. Besides, he's really looking forward to having you around. You'll like him; he's lots of fun and very cute. All the girls adore him." "Auntie!" I protested, "I'm not a girl!" "Now Pussy, I had no idea you'd be so ungrateful," Mom interjected sternly. "Ashley really needs your help and, besides, you've already agreed to take the job. You can't back out now." I thought it over briefly and decided I really was really being a baby. In truth, the idea of dressing like a girl 24/7 appealed to me, so I decided to apologize and go along with their plan. "Okay," I announced. "I'll do it. And I'm also sorry for being such a little brat. I'll do everything you say. I promise. I hope you'll forgive me." "Of course we'll forgive you, Pussy," Aunt Julie said giving me a great big hug. "But we must get started right away. Your mom has to drive back home, and we don't have much time. You have an appointment with my hair stylist this afternoon and we've been invited to Ashley's for dessert this evening... and you're still in your ugly boy clothes! Now say good-bye to your mom and march right upstairs and get the bath water running. We haven't a moment to lose." Mom wished me luck and gave me a kiss on the cheek. "I'm very proud of you, Pussy," she said as she slung her purse over her shoulder getting ready to leave. My mom and my aunt watched me as I ascended the stairs, rolling my ass provocatively form side to side. I felt very lucky to have such a wonderful aunt and mom who understood me and wanted to help me so much. Most people think my mom and Aunt Julie are sisters because they look so muck alike. Aunt Julie was really my dad's big sister and her striking resemblance to my mom is purely coincidental. They are about the same height and weight, except my mom is a brunette and Aunt Julie is a redhead. They even have the same taste in fashion and wear the same perfume. For women in their mid-thirties, they both look super hot. Men are constantly hitting on them and commenting on their beautiful asses and big tits. Once I overheard a man in a restaurant tell his friend he liked my mom's dick-sucking lips and wished she would suck him off sometime. Believe me, Aunt Julie's lips are just as dick-suckingly luscious as my mom's. My mom says I've inherited their features. I also have a nice ass and a tiny waist, and she assures me that someday men will want me to suck them off too. As soon as Mom left, Aunt Julie came upstairs to help me get ready for my appointment with Roxanne, her hair stylist. My aunt bathed me, then removed my body hair with Nair. I loved how silky my body felt when she finished. Then she taped my chest and applied a touch of make up between my boobs to create the illusion that I had cleavage. Next she inserted D-cup silicon breast forms into my bra. Mom bought them for me, along with a gaffe, to smooth out the bulge between my legs. I was delighted how beautifully my boobs bounced when I walked and how realistic my crotch looked in the gaffe. After she put my make up on, I could feel myself getting aroused. My little cock was still limp, but I could feel my nipples starting to get hard. The rest of the outfit included, tight fitting jeans, a powder blue tank top that nicely showcased my cleavage, and a cute pair of white platform sandals. Aunt Julie also gave me a platinum blond wig and clip on earrings just to wear to the hair stylists, where I would have my hair and nails done and my ears pierced. I suggested that it might be unnecessary to perm my hair, and that I could wear a wig instead. Aunt Julie said I would understand later why a perm was a must. "A wig takes half the fun out of it," she said. I'm sure you'll see why tonight when you meet Ashley and her boys." I think we were both amazed how pretty and sexy I looked. "Pussy, I think you're the cutest little 15 year old cunt in town," Aunt Julie remarked while playfully fondling my ass. "Just wait till Roxanne works her magic. Any guy I know, who isn't a pansy, would want to take you right on the spot... and some girls I know too. We're going to have so much fun!" she exclaimed with glee. Then, to my surprise, Aunt Julie slapped me hard on the ass and said, "Enough day dreaming, Pussy. Grab your purse and let's get going." I took the purse she had prepared for me; it contained all the things a girl like me needs when venturing out in public. On the way to Roxanne's, Aunt Julie told me some secrets of her own. "Your mom told me you know about your dad and some of his exploits." she said. "Did you know that I used to fuck your dad too? Your parents and I would often go out together and pick up guys at clubs and bars. Later we would all end up fucking one another- and your dad, the little slut, would take us all on. Our dates would end up fucking him up the ass and in the mouth, and so would your mom and I with strap-ons," she said with delight. "Your mom said it was all right for me to tell you," she added. "Aunt Julie? What was my dad's girl name?" I inquired. "Don't you know?" she said with amazement. "We called her, Pussy." "What a coincidence!" I said with a smile. "Yes it is, quite so... Pussy," she replied. My nipples were rock hard by the time we got to Roxanne's and I was very much in the mood for further pampering. It was obvious that Roxanne was looking forward to my makeover. There was a gleam in her eye and she gave me so much attention. I truly felt like a princess. Hours later, when I was finally permitted to look myself over in the mirror, I was so moved by my appearance I started to cry. My bleached hair looked so sexy in long curls, my ears were pierced and my toenails and fingernails looked so cute. I felt like a total pussy - and it showed. "You're every bit the beauty your father was, Pussy," Aunt Julie whispered in my ear. I can't wait until Ashley and Brian get to meet their new babysitter. They'll be ecstatic!" she said. Roxanne handed me a Kleenex to dry my tears and clean my mascara. After retouching my make up and spritzing me with perfume, Roxanne asked Aunt Julie if she minded if her daughters came downstairs to meet me; Roxanne lived with her two girls in an apartment above the salon and she wanted to show them how beautiful I looked. Aunt Julie said she didn't mind, so while she paid the bill, Roxanne called her daughters on her cell phone to invite them to have a look. I could hear them hurrying down the stairs to check me out and felt a bit apprehensive about teenage girls looking me over. Aunt Julie, however, seemed very amused by my predicament. "Pussy, I'd like you to meet my girls Karen and Melissa. Girls, this is Pussy. What do you think? Pretty cute for a fifteen year old boy, isn't she?" she said. Roxanne's girls shook their heads in disbelief. "Shit Mom, that's not a boy!" Karen exclaimed. "Don't try to fool us. Look at her ass - it's bigger and rounder than Melissa's. We know a girl when we see one," she added. "No, no she's really a boy," said Aunt Julie. "Pussy, bend over and spread your legs so the girls can feel what you have between your legs." she instructed. Obediently, I did as she said. The girls groped me for a few moments but failed to feel my little nuts and cock, which were tightly tucked up my crotch. "Do you feel anything, Melissa?" questioned Karen, the older of the two girls. "It feels like a cunt to me," replied the sixteen year old to her sister. "Pussy, get out of those jeans and panties and show them why they can't feel anything." Again I did as she said, peeling the skin-tight jeans down around my buns and slipping my panties off to reveal my tiny, pathetic twinkie. What they saw made them crack up hysterically. Karen said she had never seen anything so small on any boy older that ten years old, and Melissa just stood there laughing. Everyone agreed that I could never satisfy a women with such an insignificant cock. Karen started to play with my pecker and Melissa felt up my nuts still in disbelief. "They feel like tiny grapes," said the pretty sixteen year old. "No wonder we really thought Pussy was a girl." "And look at the Pussy's nice big ass," said Roxanne as she fondled me from behind. All this attention was starting to give me a hard on, causing my prick to swell to it's full length of three and a half inches. When my admirer's saw how little my erection was, they began to laugh uncontrollably, immediately causing my manhood to shrink back down to its original limp state. Again I started to cry - this time from humiliation. "Girls, stop making fun or Julie's sissy faggot. Imagine if your big tits were the size of little plums. Would you like people laughing at them? Pussy is beautiful and very sexy and we should accept her as one of us," Roxanne proclaimed. Karen and Melissa apologized for making fun of my little prick and told me they thought I was really hot looking. I said I knew they were just having some fun and that I didn't care about the size of my prick. I just wanted to be one of the girls. "You do have a nice big ass, Pussy," said Melissa. "Has it ever been fucked?" "No honey," Aunt Julie interjected. "She's still got her cherry." "But not for long, I bet," said Roxanne. "Let's hope not," replied my aunt. I put my panties and jeans back on and thanked Roxanne for her help. Karen and Melissa told me to call them whenever I wanted. They said they liked me and would like having me as a friend. They even said they knew lots of guys who would like to "break me in", if I liked. As I minced my way to the car, I no longer felt timid about going out in public en femme. In fact I wanted everyone to see how hot I looked. Finally, I looked like the lovely, sexy babe I always dreamed about being; the one that lived inside of me but could never get out. "Holy fucking shit!" Ashley exclaimed when she answered the door. "I knew your nephew was a sissy, but I had no idea she looked like Pamela Anderson!" she added. "Hi Ashley," I said sweetly. Her comment about my looking like Pamela Anderson was certainly an exaggeration, but greatly appreciated. Brian got up from the couch where he had been playing with Billy and walked over to greet us. By the look on his face, he was pleased with the appearance of his new babysitter. "Oh yeah!" he exclaimed as he slowly slipped his hand around my waist, drawing me close to his muscular body. "Pussy, you're a doll. Welcome," he whispered in my ear, gently kissing me on the cheek. "Thanks you, Brian. You're so sweet," I answered coquettishly. "I'm looking forward to being your babysitter. Thank you for considering me for the job," I said. "I'm sure you're a little inexperienced, but I'm sure Brian will break you in just fine," Ashley added. Billy, who was in his PJ's and ready for bed, was sitting on the couch playing with a teddy bear. I walked over to talk to him to give him a chance to get used to me. He smiled when I talked to him and giggled when I touched his tiny toes. He lifted up his arms to signal he wanted me to pick him up. Ashley said that was a good sign, because he typically starts to cry when he meets someone new, especially boys or men. I held him for a few moments happy I passed my first test, then Ashley said she and I should take Billy upstairs to tuck him in for the night. Brian and Ashley seemed awfully nice, and Billy was as cute as a button. After we said good night to Billy, Ashley gave me a tour of the house and outlined my babysitting responsibilities. She also made it clear that I would also be expected to be Brian's surrogate lover in her absence. "Brian needs to have constant sex," she explained. "If he doesn't have someone to fuck at home, he'll go looking for women on his own, and who knows what rags he'd bring into the house. It's better this way. I hope you understand, Pussy. You're so sweet and Brain has been asking for a sissy lately, so you're perfect." It all made perfect sense to me. "Oh yes, I understand... but I'm still a virgin," I admitted shyly. "Then you're in luck," she said. "Brian is as gentle as a lamb. He's just the right guy to pop your cherry. Trust me," she said. "I do trust you, Ashley... and don't worry about your boys. I'll be a perfect substitute wife and mother. I'll do everything I can to make them happy," I added reassuringly. Ashley put both hands on my hips, drew me closer and whispered, "Brian's a very horny boy and he'll want to fuck you night and day... and so will his friends. You know you're so cute and sexy, I can't really blame him." Then she kissed me gently on the lips and slid her hands down around my ass, which she continued to fondle for a few tender moments. When we returned to the living room, Aunt Julie was sitting across from Brian on the couch. "How are we doing girls?" Brian asked. "Just fine, Honey," Ashley answered. "Are you ready for dessert?" He inquired with a grin. "Sure thing. Let's have some right now," she said. Ashley led me by the hand to the couch where we positioned ourselves like ducks in a row; Ashley on the left, me on the right, and Aunt Julie in the middle. As soon as we were seated, Brian stood up and approached the couch, undoing the zipper on his jeans along the way. Suddenly I realized what he meant by "Dessert". I was going to get my first glimpse of Brian's manhood, and more than likely, a taste of it too. Brian stepped out of his jeans, exposing his throbbing ten- inch dick for all to admire. After stroking it a few times, he began rubbing it all over his wife's pretty face, making a real mess of her makeup. When she turned her head to glance at Aunt Julie and me, he poked his cock into her ear. The sensation made Ashley shiver. "He's such a tease," she cooed. Grasping his balls in her delicate hands, she began kissing the tip of his prick, then she licked the shaft from top to bottom. Soon she was sucking on the head and massaging his cock with both hands, making loud slurping noises as she sucked. Aunt Julie and I watched with great amusement. "Would you like some, Julie?" she asked. "Oh yeah. Give it to me baby. Put it in my mouth," she answered in a low, sultry voice. Brian moved over to my slut aunt and stuffed his huge prick into her eager mouth. Aunt Julie took the whole thing down her throat, then she started rocking her head back and forth, massaging Brian's cock with her lips, tongue and throat. Saliva escaped from the corners of her pretty mouth and dripped down her cheeks and chin. "Brian likes it wet," she said glancing my way. "I'll have to remember that," I said. Aunt Julie continued pleasuring Brian for a while, then she looked at me and said, "Now it's your turn, Pussy." I smiled nervously, then placed my virgin lips around the head of his cock. I did my best to apply the same techniques, but had some trouble deep throating him like my aunt. Brian gave me lots of help by grabbing my hair and forcing his cock all the way down my throat. I started to gag at first, but eventually got the hang of it. "You see, Pussy, that's why you shouldn't wear a wig. A wig would come right off you head," Aunt Julie said. I grunted in agreement. Years trickled down my face smearing mascara down my ckeeks. Soon luscious gobs of cum filled my mouth and Brian's cock started to get limp. I carefully licked the last few drops of cum from its shrinking head. "You're a natural-born cocksucker," Brian proclaimed approvingly, releasing his grip from my newly coiffed head. "Yes, you really know how to use those beautiful dick- sucking lips," Ashley agreed. "Just like your cock-loving father," Aunt Julie added. Ashley and Brian wanted me to return the next day for lunch ready to stay for the remainder of the week. Ashley wasn't leaving until the following day, but they wanted to take me out to get to know me better. They really were both so nice. When she greeted Aunt Julie and me at the front door the following day, Ashley was wearing a short yellow sundress with white high-heeled sandals and a pretty white ribbon in her hair. The lowcut neckline revealed a pair of big tits that seemed to defy gravity. "Good morning girls," Ashley said in a cheery voice. "Good morning Ashley," Aunt Julie answered, "That's a cute outfit you're wearing," I said, noticing how beautifully she was package. "Thanks," she said. "Brian likes sundresses because they provide easy access to my cunt and ass," she said flirtatiously lifting her dress for all to enjoy. She wasn't wearing panties, so we enjoyed the glimpse of her pussy and lovely round ass. Then she led us to into the living room, where Brian was sitting on the couch, wearing nothing but a satin robe, which he invitingly had left open to expose his beautiful erect cock. "Billy's taking a nap and Brian was just fucking me. I hope you don't mind seeing him undressed like this?" she said. "Oh no, we don't mind a bit, but please don't let us interrupt," Aunt Julie said with a smile. Hi girls," Brian said stroking his one-eyed monster. "Actually we were just waiting for the two of you to get here. Would you like to join us?" he inquired. "If you want to know the truth, Pussy," Ashley said, "Brian played with himself all night thinking about you. You see my horny hubbie was very disappointed he didn't get to fuck you up the ass last night. No matter how much I fucked him and sucked him, I just couldn't satisfy my poor horny baby. He really needs to get his fat prick up your faggot ass soon, or he'll explode." "Oh my, I'm so sorry, Brian," I said. "Is there anything I can do to help you now?" I asked with a smile. Without saying a word, Brian stood up, and took me in his powerful arms and gave me a long passionate kiss. I could feel his prick poking my tummy; one hand squeezed my ass and the other caressed the back of my head. I seemed to lose all strength in my knees and instinctively sank to the floor before him. Lifting my face and turning my eyes upward to meet his, I opened my mouth wide and stuck out my tongue, waiting for him to insert his cock. I began sucking him off with great devotion, slowly at first, then faster as he gyrated his prick in and out of my sissy mouth. I could taste the sweet juice from Ashley's cunt, which he had been fucking just a few moments earlier. It felt like heaven being at his feet, pleasuring him in such a way in front of my sex aunt and his horny wife. I was on fire. I continued to suck his dick awaiting further instructions. "I need to fuck you now, Pussy," he said. Then he sat down on the couch and told me to straddle his body and give him a long kiss. He looked into my eyes and said, "Please be my wife while Ashley's away. You're the most beautiful sissy I've ever seen and making love to you every day would make me very happy. Please be my faggot princess." I looked into his eyes and could see how loving he was and that he needed me so much. Aunt Julie spread some lubricant on my asshole and started to work my hole open with her middle finger. Soon I felt Brian's stiff rod probing me from behind, trying to gain entry into my faggot ass-pussy. "Oh yes, Brian. I want to be your little pussy. I want to love you, to fuck you all day and night. I'll do anything you want darling... anything. Oh yesss... yessss... yesssssss!!! I'll be your faggot princess. Yeeesssssssss!!!" I moaned. I wanted his cock, but frankly I was afraid that his huge prick would be more than my tiny virgin asshole could take. "I'm afraid, Brian. Please be gentle," I begged. Brian kissed me lovingly. He pressed the head of his dick against my willing asshole, sliding it in and holding it still until I could get used to his enormous cock. "You're beautiful, Pussy," he moaned as he began to penetrate me further. "Do you want to be my bitch?" he asked. "Oh yes, Brian. I want to be your bitch," I panted. Within moments the pain subsided and all fear was gone. Soon I relaxed and started to enjoy Brian's skillful thrusts up my virgin hole. Brian fucked me in a variety of positions while Ashley and Julie took turns lapping each other's cunts and assholes. Later I was told to get on all fours so that the ladies could do my with strap-ons. Aunt Julie entered me first with a rubber dick roughly the size of Brian's cock. "I'm going to fuck you hard, like I used to fuck your sissy daddy," she said. "I want to see who's a bigger faggot, you or your dad." Then Brian moved to the front and rammed his cock down my throat before I could respond to my wife's comment. The taste of the shit on his dick was intoxicating. I never thought that I could be such a pig, but I was... I really was. Ashley fucked me next with a black dildo that was bigger than Aunt Julie's. As she slipped the massive cock up my ass she said, "So you want to be Brian's wife? You little bitch, you'd better like fucking and sucking if you want to be like me," she said slapping me hard on the ass. "Yes, I want to be like you," I screamed. When I turned my head, I could see her big tits and curly red hair bouncing behind me as she rhythmically fucked my fantastically firm faggot fanny. "You love this, you cock-sucking little assfucker, don't you?" she chided. I could hear her body slap up against my ass cheeks as she pounded me mercilessly with her enormous black dildo. Finally, Brian removed his now clean dick from my mouth and told me to lie on my back and to spread my legs wide. He positioned my legs over his shoulders and slowly inserted his cock. He banged me faster and faster until eventually he shot his hot load up into my sissy ass. Having Brian's seed deep inside me made me feel like a total pussy. It made me feel happy and complete. We could hear Brian upstairs crying because it was time for him to get up from his nap. As I began to get up off the floor, I could feel cum leaking from my ass. Aunt Julie took a tampon out of her purse and told me to insert it in my pussy to keep me from dripping all over the house. Then Ashley told me to go up to my room, put on a robe, and bring Billy down to the living room. When I greeted Billy, he called me by my name, "Sussy." How cute. I did as she instructed, bringing him down after I changed his poopy diaper and changed his clothes. What a sweet little boy. "I can't wait to take care of Billy. When do I start?" I asked. "Not for a while," said Ashley. "We've decided Billy should spend a few days with his grandma so that Brian and his friends can have more time to get to know you better. You don't mind entertaining Brian's friends too, do you?" she inquired. I glanced over at Brian for reassurance. A sly smile and the huge prick he held in his hand were all the reassurance I needed. "Oh no, I don't mind," I answered. "I'd be happy to." I added coyly. TO BE CONTINUED...

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Introduction: Cute babysitter seduces a single mother The Babysitter She gave a light tap on the door, knowing that there was a baby in the house probably trying to sleep. The tapping was loud enough to alert the childs mother who was sat in her living room. The house had been silent so the sound startled the young mother who, up to now, had been playing through the infinite possibilities of the night ahead in her mind. The more she thought about it, the more nervous and edgy she made...

2 years ago
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Engaging The Babysitter

I opened the door and saw her through the glass storm door. She just smiled and waved for a few seconds, and I had to return the favor. I opened the storm door too. "Hello, Alli, you are looking well." "Hi, Mr. Fonpolous, thank you," she replied, strolling into the house. "How are you doing? Has the dating life been decent since the divorce?" "It has been okay, Alli. It is tough out there though, and please, call me, Rex," I corrected her, failing to part my eyes from her while...

2 years ago
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Propositioning the Babysitter

Jack Niles was married for the last twenty years. He and his wife were best friends. They were each other’s soul mates. They had a healthy sexual relationship and pleased one another. Jack also had secret desires which he didn’t share with his wife. Jack was obsessed with breasts. His wife had a small chest. He begged her to get implants, however she was scared about her health. She would get real mad at her husband for ever suggesting that she needed implants. Jack’s obsession with breasts...

2 years ago
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Sunbathing Babysitter

Introduction: Our babysitter seeks answers about sex One of the things my wife and I loved about our house, the first time we saw it, was the neighborhood. There were kids playing outside, and everyone seemed to know each other. Since the house was also best of all we had looked at, we bought it immediately. While the house does have its issues, it has a lot going for it, too. First, it sits on a huge lot. Its actually nearly two full lots, meaning we have a huge backyard. It also has a great...

3 years ago
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Bobby Jo

We first met just after I started junior high school. I had entered the seventh grade like many others, in that I was awkward, felt alone and out of place most of the time. Miss Bobby as she was called singled me out on my first trip to the library in search of a research book. Even at that moment in my backward way I felt she had strange and wonderful things planned for me. What they would be was beyond my comprehension but I still felt they would be wondrous. When I noticed her watching...

1 year ago
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Bobby

Boston with its many old neighborhoods is as varied as its people. In the older seedier parts of town many people live and carry on in a world much different from the clinically clean and proper suburbs. On some streets there are rows and rows of the monotonous dark brick two, three, five or six story apartment buildings many exactly like the one next to it and just like the ones across the street. Other streets, while somewhat rundown, have a funky array of different buildings each one a...

2 years ago
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Bobby Sue Showed Everybody Her Breasts

Bobby Sue was young and wanting to please men.  Her mama didn’t like the way she dressed and told her to act like a lady and not like some cheap slut.  However, her mama wasn’t around to see how Bobby Sue was acting with the boys.Bobby Sue was eighteen and was always showing the local boys her breasts.  Her mama’s boyfriend was always looking at Bobby Sue like she was a model.  Her mama said if she caught him and her daughter together she’d throw him out of her trailer.  She'd been in a...

Interracial
4 years ago
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Bobby and Lee meet each other with me in the middl

After I dressed up for Lee a few days later i dressed for Bobby. We would fuck and suck and i would dress up but i was watching more porn and was wanting to take it further. My step dad had a video in not with the others in the box under his bed it was in a shoe box in his closet I glued one day when I was getting some of my moms clothes to wear and Fuck Bobby. The shoe box had 2 videos in it Gangbang girl 9 and Backdoor Desires, condoms, lube, and a handcuffs with a key. I watched both movies...

2 years ago
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Bobby and Spanky II English

Introduction: This is the second part of the story… enjoy. Bobby and Spanky II By Lamia Lobato After Bobby and Spankys last visit, nothing has been the same in my life. The first night that they came I left my bedroom windows open all the way whishing with all my heart that Bobby appears there while I was masturbating, but it did not happened and I did not see him. His light remained off all the time. Still, I imagined that, hidden in the darkness, his curious child eyes watched me and he did...

3 years ago
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Bobby And Friends Visit

It’s always an exciting time when Bobby, my wife’s stud lover, calls and announces he is coming by with a couple of young friends. It’s time for us to to prepare!We both take great care in getting ready for their arrival. She knows what he likes: seamed stockings with a garter belt, fuck-me heels, crotchless panties, and nude above the waist except for a pearl choker. She tops this off with eye shadow, bright red lipstick and dangly earrings. Boy, does she look slutty and fuckable!She is so...

Bisexual
2 years ago
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Bobby And Friends Visit

It’s always an exciting time when Bobby, my wife’s stud lover, calls and announces he is coming by with a couple of young friends. It’s time for us to to prepare!We both take great care in getting ready for their arrival. She knows what he likes: seamed stockings with a garter belt, fuck-me heels, crotchless panties, and nude above the waist except for a pearl choker. She tops this off with eye shadow, bright red lipstick and dangly earrings. Boy, does she look slutty and fuckable!She is so...

Bisexual
1 year ago
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Bobby and Spanky II English

By Lamia Lobato After Bobby and Spanky’s last visit, nothing has been the same in my life. The first night that they came I left my bedroom windows open all the way whishing with all my heart that Bobby appears there while I was masturbating, but it did not happened and I did not see him. His light remained off all the time. Still, I imagined that, hidden in the darkness, his curious child eyes watched me and he did the same with his huge cock. I told myself that I would ride a dick like...

2 years ago
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The Babysitter

The Babysitter She gave a light tap on the door, knowing that there was a baby in the house probably trying to sleep. The tapping was loud enough to alert the child’s mother who was sat in her living room. The house had been silent so the sound startled the young mother who, up to now, had been playing through the infinite possibilities of the night ahead in her mind. The more she thought about it, the more nervous and edgy she made herself. At least her 3 year old son, Callum, had drifted off...

2 years ago
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The Babysitter

The Babysitter She gave a light tap on the door, knowing that there was a baby in the house probably trying to sleep. The tapping was loud enough to alert the child’s mother who was sat in her living room. The house had been silent so the sound startled the young mother who, up to now, had been playing through the infinite possibilities of the night ahead in her mind. The more she thought about it, the more nervous and edgy she made herself. At least her 3 year old son, Callum, had drifted off...

Lesbian
3 years ago
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The Busty Babysitter

Rachel was just pulling her coat on when John came down the stairs. He handed Rachel her payment in cash."Thank you, Mr. Greene." Rachel smiled in gratitude."You're welcome," he replied. "You deserve every penny. Kathy and I are very happy with you. There is no one that we trust the k**s with more than you.""Thank you, that means a lot. I love them like they're my own. I would do anything for you guys." Rachel was starting to blush and was having a hard time meeting John's gaze. For his part,...

2 years ago
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Sara The Bad Babysitter

Mr. and Mrs. Crudele were going to have a much needed night out. Since the arrival of their little bundle of joy four months ago they hadn’t had a night out together and in fact they rarely had a few hours sleep in a row. But tonight they had plans for a quick supper followed by an evening at their favorite club. Mr. Crudele had obtained the name of a young woman from a subordinate at his company who said that she was very reliable and came highly recommended. He had called her and she was...

4 years ago
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The Babysitter

Introduction: A fifteen-year-old gets to babysit two incredibly hot twin boys My name is Mark. Im fifteen, with light brown hair and brown eyes. Im just an average kid, 57, 150 lbs. I think Im into guys, but Im not sure. I mean, I dont want to be gay, but sometimes I catch myself staring at some guys ass, and I think I might be. I know that younger boys turn me on. Theres one family across the street that has two of the hottest boys Ive ever seen. Theyre twins, and they look about ten or...

2 years ago
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Bobby and Spanky III

Introduction: English Bobby y Spanky By Lamia Fangs I never thought that a dog and a child could modify my life so strongly: I keep thinking about them, especially about Sally, she said she wants to come and play with us, I would be pleased to play with her, too since I love playing with the boy and his wonder dog. However, I must be careful, it would be fatal if things do not get out of control. They could charge me of rape, statutory rape, and pedophilia at least. However, the judges in the...

3 years ago
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Bobby and Spanky III

By Lamia Fangs I never thought that a dog and a child could modify my life so strongly: I keep thinking about them, especially about Sally, she said she wants to come and play with us, I would be pleased to play with her, too since I love playing with the boy and his wonder dog. However, I must be careful; it would be fatal if things do not get out of control. They could charge me of rape, statutory rape, and pedophilia at least. However, the judges in the court do not know that nowadays...

1 year ago
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Bobby takes a hint Ashley 2

Introduction: Constructive criticism welcome. I cant gey better unless I know whats wrong. I waved good-bye and watched my mom and dad drive away. As soon as they were out of sight, I pulled a cigarette from my purse and lit it. About a year and a half ago, my parents had decided that they needed a weekend away with no kids. It had been so much fun that they made a regular thing of it. Now, the second weekend of every other month was their designated alone time. That meant that my sister and...

3 years ago
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Bobby takes a hint Ashley 2

About a year and a half ago, my parents had decided that they needed a weekend away with no kids. It had been so much fun that they made a regular thing of it. Now, the second weekend of every other month was their designated 'alone time'. That meant that my sister and I had to find a place to spend the weekend. I usually stayed with my best friend, Sara. She lived four houses down from me with her mom, Angie, and older brother, Bobby. Sara's dad was long gone and her mom let us...

4 years ago
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bobby come home

It is Saturday about 3 p.m. and Bobby is due home from college any minute now.It has been about 6 weeks since I have seen him and I am looking forward toit.Doing my usual Saturday household chores, I have already changed the sheets onBobby's bed, cleaned his room and done the washing. Bobby always brings homesome clothes for me to wash.I hear Bobby come in the door and rush to meet him. I put my arms around hisneck and hug him tightly. He gives a superficial hug back. He has never beenone...

2 years ago
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Bobby and Spanky

La semana pasada estaba tomando el sol en mi jardin cuando escuche ruido en la cerca divisoria de un costado de su casa. Me di cuenta que el perro trataba de cruzar la cerca. No puse demasiada atención pues asumí que el perro era muy grande para pasar por entre las tablas así que volví a cerrar los ojos… pasaron unos minutos y volví a escuchar ruido mas cerca de mi, abrí los ojos y cual fue mi sorpresa cuando veo junto a mi al enorme al enorme perro con su lengua colgando y chorros de...

2 years ago
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Bobbys Mom

Alicia is a very special person in my world. She is a great many things to me. She's my best friend, my confidant, my girlfriend, my lover and my mom. Mom seems to really love her role as my own personal cumslut and is always there for me whenever I need to get off. Lately, I've been able to forget about my alarm clock because every morning I awake to the feel of warm, wet lips sucking my cock. Let me tell you, it's a great way to start the day!Mom and I live alone and there is no dad to talk...

3 years ago
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Bobby Radhika And Me 8211 A Bisexual Threesome

Hi ISS readers. I am Aakash, 21 years old from Kerala. I am sufficiently tall and I weigh around 90 kg. This is the first story I am publishing in ISS. I was a virgin until about 2 years back and I will publish all my earlier escapades based on the response I get for this. Please mail me your response – This story I am about to narrate is about my first bisexual threesome with a married couple which happened almost 1 year back. I had met a couple in a chat room who where looking for a...

1 year ago
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Bobby and Mom

Bobby went upstairs heading for his mother’s room. Half an hour ago he had seen her take several sleeping pills. He opened the door. He saw his mother Cindy lying on the bed fast asleep. Bobby came closer and sat down on the bed turning on the bedside lamp. He had been planning for this day for almost a week. He touched his mother to see if the pills had done their job. Cindy didn’t react and Bobby tried again. Soon he was sure that his mother was not going to wake up. He carefully pulled the...

Incest
3 years ago
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Naughty Babysitter

Introduction: OK readers, here comes a LONG story that I have been working on for a while. I dont think this will become a series unless I get requests for it. Tina comes home early and finds a surprise in her bedroom, the babysitter masturbating on her bed. She could just fire the girl, but decides to punish her, while living out one of her fantasies. Paul and Tina have been married for about 6 years, and have a 3 year old daughter. Instead of taking their daughter to a daycare, they have a...

2 years ago
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my new babysitter

The new babysitterAt this time i want to tell you a story of when i got a new babysitter.one evening my parents chatting and came up with the idea of going out on a romantic dinner for two being they were married for about 11 years and didn’t get the chance to go out much for some alone time for a long time now,being i was sick often and hadand therapy and other activities and a baby sister my mom had her hands full.my dad brought up the idea of perhaps having dinner just the two of...

2 years ago
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Bobby and Spanky IV

Introduction: English Bobby and Spanky (Phase 2) by Lamia Fangs I will continue my story avoiding useless details. So I will begin by saying that two days after our last meeting, the neighbors parents came to my house introduce themselves and to tell me that they were pleased to meet me, same as their kids, and to assure me not to worry if I notice that the kids spent too much time home alone. They know how to look after themselves. No doubt about it I answered. From that moment on, we, adults,...

1 year ago
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Bobby Invites Anne Carol And The Swinging Wives To A Party

Anne and Carol have received an invitation to a Girls Night Out Party at Bobby Vasquez’s estate. He also invited the wives from Dr. Carlos’s swingers group. He was there that night at the Lake. He is well known by the married ladies. There are two stipulations for the party. Plenty of food, beverage and entertainment provided. Bathing suits and wedding rings optional. My name is Anne. My best friend and co-worker is Carol. We have been invited to Bobby Vasquez’s estate for a Girls Night...

Group
1 year ago
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Bobby and Scott

It had been a couple of weeks since I watched Bobby and Scott in the woods. I called the number they gave me, and surprisingly it worked. Bobby answered it, and we made plans to meet on the weekend. I met them at the restaurant and we had a few drinks and a good meal. They followed me back to my house and had an other drink. Scott reached over and unbuttoned Bobby's shirt. As he did I sat beside him and unbuckled his belt and pants. Scott leaned back and gave me a kiss. As Bobby stood up we...

3 years ago
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Engaging The Babysitter

I walked towards the door and saw her through the small window. 'Oh, there she is the barely legal dazzling brunette I have babysitting my son. What I wouldn't do to give a ride, and I don't mean in my car. Shit, she is wearing a dress like that to a babysitting gig? Is she trying to turn me on now?'I opened the door and saw her through the glass storm door. She just smiled and waved for a few seconds, and I had to return the favor.I opened the storm door too. "Hello, Alli, you are looking...

Taboo
1 year ago
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BlondieDennis The Menace The New Babysitter

Blondie/Dennis The Menace: The New Babysitter (Or When Dennis Meets Blondie)by Sniper32One Friday night Dennis was introduced to his new babysitter, a nice younglady named Blondie Bumsted. She was a 35 years old friend of his mother, shewas a stunning 5'9, slimmed hipped, long legs, a nice ass and a perfect setof 38c breasts.Denise's parents Henry and Alice were going out for dinner and dancing fortheir anniversary and would be gone most of the night.Now as everybody knows Dennis is a handful...

2 years ago
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Bobby and Spanky English

Introduction: this is the englis versiion of my original work. Bobby and Spanky By Lamia Lobato Since few months ago, I have new neighbors in the house next to mine, they are a small family: both parents young and beautiful with two equally beautiful little children and a big and obedient dog which the kids take out for a walk every afternoon. The girl may be around 16 years old, tall and slender, with a young body but yet fully built with a round butt and a good pair of 34C boobs, and the...

2 years ago
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Michelles New Babysitter

       I love my wife.  One of her best qualities is how she let’s me treat her thirteen year old daughter, Michelle.  My first treat was when she informed me that I should be the one spanking her, and that she would be stripped first.  I went along and spanked her thinking it was just the way they did things in their family; the fact that I was enjoying myself I kept to myself.  Than one day I came home to see that my wife had invited all of her friends over and had Michelle in diapers on the...

3 years ago
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B Is for Babysitter

It's never easy for a child when his parents split up. Circumstances affect circumstances and usually for the worse. In Billy Bonds' case, his parents' impending divorce was all the harder because he knew deep down that, despite what they always say, he was the cause of it all. He wasn't, of course. But what's a 14 year-old boy on the edge of puberty and teenage defiance, painfully self-aware and utterly confused about everything supposed to know about life? You could say Billy was a...

4 years ago
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Bobby and Spanky IV

(Phase 2) by Lamia Fangs I will continue my story avoiding useless details. So I will begin by saying that two days after our last meeting, the neighbors’ parents came to my house introduce themselves and to tell me that they were pleased to meet me, same as their kids, and to assure me not to worry if I notice that the kids spent too much time home alone. — They know how to look after themselves. — No doubt about it — I answered. From that moment on, we, adults, became the best new...

4 years ago
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Bobby and Spanky English

By Lamia Lobato Since few months ago, I have new neighbors in the house next to mine, they are a small family: both parents young and beautiful with two equally beautiful little children and a big and obedient dog which the kids take out for a walk every afternoon. The girl may be around 16 years old, tall and slender, with a young body but yet fully built with a round butt and a good pair of 34C boobs, and the younger brother of about 12 or 13 years old with blond hair and blue eyes. He...

2 years ago
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Bobby

It began with a cold wet April late night knock on my door. Bedraggled, wet, and wretched, clutching a small satchel, Bobby stood at my door. “I’ve been kicked out; can I come in?” Of course I let him in. He was a young man, whom I had tutored before his university admission tests. Bright, articulate, personable, but he did lack focus. Decades younger than I, I was never tempted by him, although there was no doubt he was attractive. He just seemed too young, although he was legally an adult. He...

2 years ago
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Bobbys Slut Male Multiple Orgasms

It was the beginning of May and the days were getting much warmer so I would sit out on the porch after I put the k**s to bed. A guy, that lived with his parents, next door, started sitting and talking to me. I felt so lonely and it really felt good to speak to someone.His name was Bobby. He was 22, not terribly good looking and was about 5" 8". But he was nice. This went on for about a week, He would always come right to the porch and sit next me and just talk, mostly about me, for a couple of...

1 year ago
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Bobby Again Fucked By Young Guy

Hi readers its housewife Bobby (just a name not real) again with continuation of my first part Housewife Bobby Fucked By Young Guy. Thanks for your emails comments. Before reading this please go through that story; since we have our first sexual session. After that just like lovers we were in bed kissing caressing and cuddling each other. Suddenly he got an emergency call so he went out leaving me at my sexual peak. I laid on bed fully naked thinking of those magical moments. Then next Monday...

3 years ago
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Abigail the Babysitter

This is my first try… Leave comments to what you think could be improved! * * * It was six oclock on Friday night when Abigail began to make her way down the street towards the OLachlan house. She grumbled under her breath. There were plenty of things that she would rather be doing on a Friday night that didnt involve babysitting two teenage brats. Her mother had pressured her into babysitting the OLachlans kids, though Abigail didnt see why they needed babysitting. The oldest, Jacob, was...

1 year ago
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Naughty Babysitter

Instead of taking their daughter to a daycare, they have a babysitter come in to watch her during the day. They had just recently hired a new babysitter, Jennifer, an 18 year old freshman at the local university. Jennifer only took afternoon and evening classes, so she was able to babysit until Tina or Paul got home. Jennifer stands average height, with an average build. She did play sports in high school, along with being a cheerleader. She was excited about finding the babysitting job so...

4 years ago
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Naughty Babysitter

Paul and Tina have been married for about 6 years, and have a 3 year old.Instead of taking their daughter to a daycare, they have a babysitter come in to watch her during the day. They had just recently hired a new babysitter, Jennifer, an 18 year old freshman at the local university. Jennifer only took afternoon and evening classes, so she was able to babysit until Tina or Paul got home.Jennifer stands average height, with an average build. She did play sports in high school, along with being...

2 years ago
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The Babysitter

My wife, Amy, had left to go see her sister for a few days, apparently her and her husband were having some marriage troubles and she wanted to be there to support her. That left me at home to watch our two little girls Sarah, who was three and Paula, who was five. They were good girls and helped Daddy as much as three and five-year old girls can. My wife was supposed to be gone for a week but maybe longer, it would depend on what happened with her sister.  I didn't mind her going, I try to be...

Taboo
2 years ago
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Ditz the Babysitter

In a sudden delusion caused by two simultaneous synapses crossing each other, I thought, "Gee, wouldn't it be keen to tell the story of how I, Harvey Marcus, got started with all of this screwing around. I mean, it didn't just happen out of nothing. Everything has a cause, a spark, an ignition. So, here's my first Official Retrospective. Appropriately, it is my Origin Episode, how I involuntarily got sucked into a campaign of accidental sex with all of the world's eighteen-year and older...

1 year ago
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The Babysitter

Falling victim to the fashion trend of the tight black leggins, left almost nothing to the imagination, as her legs, small hips, and the tiny gap between her thighs, were open-season for anyone who dared to view them for more than two seconds. She was not the first babysitter Mister I would have chosen to watch his k**s, since Teagan was just a k** herself, yet he also didn't dare to tell his wife that he found her to be somewhat of a distraction as well."The k**s love her," she always said,...

4 years ago
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Taken By The Babysitter

Chapter 1Chelsea, our regular babysitter for the last five years had recently left for college but recommended her younger sister, Angela, for the job. Chelsea told us that Angela had graduated high school a year early with honors but was taking a year off before she went to college on a full academic scholarship and would welcome the income, and she also loved kids.So, about a week ago, my wife Janice arranged for Angela to watch our five-year-old son for a couple of hours so that we could go...

Teen
2 years ago
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An Unexpected Threesome With The Babysitter

My husband and I were celebrating our wedding anniversary and we asked our babysitter to come over. Sandy is a young woman who’s nineteen, very reliable and always available to make some money. She’s so good with our children and we’ve had her babysit our children for the last few years. Our children just love her to death. Rex and I were celebrating our twentieth wedding anniversary. We always go to the same restaurant when we're celebrating special events. We both love Italian food and...

Group Sex
3 years ago
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The Hot Babysitter

(It is implied that all characters in the story are atleast 18, and at no point am I implying that any characters are under 18) https://youtu.be/zNtBUerpNcE ======================================= It was hot Saturday night in the fall, and your parents wanted to go out on a nice date. They wanted to get dinner and then go watch a show in the city, which meant you had a good 4-5 hours at home alone. You got really excited when you heard that. You just thought of all the porn you could watch in 4...

Teen
4 years ago
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My new babysitter

When I was a little boy, mom had just been mom, but recently I had begun to notice that she was also a gorgeous female and I checked out her amazing body whenever I figured I could do so unnoticed. Since my parents really weren’t really very prude, I had even managed to get a couple of glimpses of my mom in partial or full state of undress, in the bathroom for instance. Being a horny young teenage boy, I of course jacked off all the time and the images that were burned in my mind of my nude mom...

1 year ago
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Cosplayer babysitter

You're sitting in class paying close attention to the clock as it ticks down to the final bell. You were just seconds away from becoming free from High school. Everyone else in the classroom now seemed to be doing the same thing you were doing as you start to hear the class shout 10! 9! 8! 7! 6! 5! 4! 3! 2! 1! RIIINNNGGG! The entire class of seniors stands up and cheers as their 4 long years of High School were finally over. You get and smile as you walk out of class with your friend Joe. You...

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