My New Babysitter - Part 3 free porn video

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I even discovered that our maid Simone was part of the debauchery going on at our mansion. One afternoon while I was bored, I was feeling horny. However, my mom had gone out to lunch with friends so I couldn’t turn to her. I saw no other opportunity than getting my old collection of porn magazines out from under my bed and wank over these like I used to. I discarded my clothes, lay on my back on my bed and started jacking off while looking at some of my favourite pictures.
I was just getting into it when there was a knock on my door. As far as I knew nobody else was at home save Simone, so I assumed it to be her. “Just a second!” I yelled. I quickly stuffed my magazine under my pillow, grabbed pants and a shirt and hurriedly put them on. “Come in,” I said.
The door opened and Simone walked in. “Hello, Joey,” she smiled, “what were you doing?”
I was surprised to hear her ask that question. What business of hers was that?
“You were jacking off, weren’t you?” she asked, with a weird smile on her face.
“Err, no, I wasn’t,” I stuttered.
“I bet you were. Your pants are on the wrong way.”
I looked down at my pants and saw that she was right. In my haste, I had put them on the wrong way. I felt trapped and blushed. This was embarrassing, being caught wanking by the maid, even when it really wasn’t any of her business.
“I don’t mind, Joey,” Simone smiled, “in fact, why don’t you just continue? I would love to watch you wank.”
I was stunned. Our maid was saying to me she would like to watch me jack off? However, after all the recent developments I wasn’t as shocked as I normally would have been. I gave Simone a good, long look. I realized I had never really looked at her before. She had always just been the maid, always around, always friendly, but I had never looked at her as a woman. Now that I did, I found that she wasn’t as unattractive as I had always assumed. Sure, she wasn’t very young – fifty-two, as I later learned – and her face wasn’t very pretty. Her nose was sharp and too large, her lips were too small, her eyebrows were uneven and her chin was too pronounced. Her make-up didn’t really distract from that, but her face was surrounded by beautiful, long black hairs.
Her body looked better, upon closer examination. She was not too tall, a bit stocky and most of her body was hidden from view by the outfit she always wore – long white skirt and wide white shirt – but from what I could make out she had a pretty decent body. Her breasts seemed fairly large, though smaller than my mom’s and certainly smaller than Debby’s and her ass looked fine as well. So I thought, what the heck, if she wants to watch me wank, I’ll let her.
“Okay,” I said, “if that’s what you want.”
I dropped my pants and took hold of my still half-erect dick, starting to stroke it slowly. “You like that, Simone?” I asked, “watching me beat off?”
“Yes, Joey,” she said, “I like it. Now come on, do it faster.”
I creased my wanking pace while Simone began to take off her clothes. She unbuttoned her shirt, revealing a large pink bra. “You like watching me take off my clothes, Joey?” she lewdly asked, licking her lips.
“Yeah,” I panted, stroking my hard cock faster and faster, “show me your tits.”
She seemed happy to comply, taking off her shirt and lifting her breasts from her bra. They sagged quite a bit, but the sight aroused me further nevertheless. Next, she pulled down her skirt, revealing a pair of skimpy pink panties.
She came up to me, massaging her breasts. She knelt in front of me. “Give it me,” she said, “come on, give it to me.”
I jerked my prick faster and faster while Simone put a hand in her panties and started playing with herself. Already on the brink of coming, I couldn’t take anymore and experienced a fierce orgasm. I shot my load all over Simone’s tits, splattering my young semen all over her boobs. Needless to say, I fucked Simone’s brains out afterwards, gaining a new appreciation of our trusty old maid.
Altogether, I was having the time of my life. The only thing I regretted was not having seen Debby again since that wondrous night. That was going to change soon, or at least I hoped so, since my mom had told me that there would be another meeting of their ‘circle of friends’ next weekend. I knew Debby, as well as her parents, was part of that circle.

That Saturday morning my father George, my mother Nastya, Simone and myself got into my dad’s SUV for the drive to Debby’s parents’ house, where the meeting of the ‘circle of friends’ would take place. It would be about a two-hour drive, since Debby’s parents lived on the opposite side of the large city where we lived.
My dad was driving. He was wearing one of his expensive business suits as usual, with the exception that he wasn’t wearing a tie. My mother sat next to him, looking as stunning as always in a short, low-cut purple dress. The dress was somewhat transparent and the dark blue lace bra she wore beneath it, containing her massive boobs, was clearly visible through the dress, as was her matching string. Simone, sitting beside me on the back seat, looked a lot less spectacular, wearing simple white skirt and similar shirt as always.
While we were driving, I was thinking about the debauchery that awaited me. Even though I’d had about as much pussy as I could handle over the past fortnight, I had never experienced an actual orgy and the prospect really excited me. Not to mention the fact that I was going to see – and hopefully fuck – Debby again.

When we arrived at Debby’s parents’ house, the first thing I noticed was that it was a huge mansion, even bigger than our own, surrounded by an enormous lawn. All around the lawn, high iron fences were in place. These people were obviously very wealthy.
We passed through a gate in the fencing that was opened and gave access to a brick-paved road leading through the lawn to the mansion. My dad drove the car down this road and then around the house itself to a large area behind the mansion that was obviously intended as a parking place, as it was already full of some twenty cars. Most of these cars were rather expensive-looking, something that didn’t really surprise me.
My dad parked our car and we all got out, walking back around the mansion to the main entrance. My dad rang the door bell and a moment later the door opened, revealing a classy-looking woman probably in her early fifties. She had short blond hair and intelligent eyes. She was tall and quite slim, but not skinny in any way. She wore a short white skirt and a very low-cut brown shirt, showing off her large breasts and revealing ample cleavage. She also sported an expensive-looking necklace and matching earrings. She wasn’t wearing a bra and I could see her erect nipples through her shirt. Apparently she was looking forward to the meeting as well.
She obviously knew my parents and Simone, greeting them warmly. Then my father said, indicating me, “this is our son Joey. He’s come with us to a circle meeting for the first time.”
“Ah, Joey,” the woman said, smiling warmly, “nice to meet you. Debby told me all about you. I’m her mother, Denise.” She gave me a kiss on the cheek.
“Nice to meet you too, Denise,” I said politely.
Denise smiled again and turned, leading us into a large hallway with a huge dome-shaped ceiling and a shining marble floor. She then led us up a big, winding marble stairway. Though I was used to huge, luxurious houses this mansion still impressed me.

Arriving on the first floor, we walked through a carpeted hallway that had paintings on the wall everywhere. They were all done in a classical style and almost all of them were of a decidedly erotic nature. Near the end of the hallway, Denise opened a door and we went into a large room. There was a luxurious, thick carpet on the room’s floor but there was little furniture, save for a few velvet couches along the walls and a few tables that were laden with food and drinks. The room was already full of people. Looking around, I figured there were some forty or fifty people there, all merrily eating, drinking and talking to each other.
We crossed the room towards the tables with the food and drinks. My parents and Simone were greeted by the people present, whom they obviously all knew, introducing me along the way. There were so many people, though, that I forgot most of the names of the people introduced to me almost instantly.
I noticed that there were roughly two generations present: mostly couples in their late thirties, forties and fifties, like my parents, who made up about two-thirds of the party I guessed. Then there were the people in their teens and twenties, whom I assumed to mostly be the offspring of the couples.
There were lots of attractive mature women as well as quite a few gorgeous young girls and even when I had a hard time keeping my eyes off some of them, I was concentrating mostly on locating Debby. It didn’t take me that long to notice her, standing in a corner talking to a distinguished-looking older man. She looked stunning in a tight, short and low-cut red dress that comprehensively showcased her enormous boobs. Though still not an image of conventional beauty, Debby looked a lot more glamorous and less girl-next-door-like compared to the first time I had met her. Her reddish brown hairs had been styled and were hanging loose around her face, more attention had been paid to her make-up and she wore large, beautiful silver earrings. As soon as I spotted her, I walked over to her. When she saw me, she smiled. “Hello, Joey, nice to see you again.” She hugged me and gave me a wet kiss on my mouth. “Great to see you again, too, Debby,” I said.
“This is my father, Lucas,” Debby said, indicating the man she had been talking to. “Dad, this is Joey. He’s George and Nastya’s son.”
“Ah,” the older man said, “good to meet you, Joey.”
We shook hands and I said, “good to meet you, too, sir.”
Debby’s father laughed. “Don’t ‘sir’ me, Joey, we’re all friends here. Call me Lucas.”
I smiled. “All right, Lucas.”
“So,” I said, “when does, eh, when does the party start?”
“At noon exactly,” Debby said, “that has become sort of a tradition.”
I glanced over at a large clock on the wall. It was two minutes before noon. Looking around, I now noticed a growing sense of anticipation among the people present. When there was one more minute to go, most of the party stopped eating and drinking and diverted their attention to the clock. Conversation subsided. I looked around eagerly at all the attractive women, wondering how many of them I would get to fuck today. I decided to stay close to Debby, though, hoping she would be the first of them.
When there were twenty seconds to go before noon, to my surprise all of the guests began to count down. “Twenty . . . nineteen . . . eighteen . . .”
Hesitantly, I joined in the counting, without even looking at the clock. My eyes were still glued to Debby.
“Five . . . four . . . three . . . two . . . one . . . go!”

Everywhere around me, people began touching each other and removing their own or each others clothes. Within moments almost all the guests, spread through the room, were partially dressed or completely nude and engaging in all kinds of sexual acts. I didn’t really know what to do, being new to all this. I turned to Debby, but she was already busy exchanging saliva with a man in his mid-forties whose name I couldn’t remember. He was certainly eager, though. While they were kissing he was freeing her huge tits from her dress with one hand while his other hand was busy between her legs. I couldn’t blame him, though.
Before I could ponder any longer on what to do, Denise suddenly appeared in front of me.
“Hello Joey,” she smiled, “would you like me to suck your cock?”
“Sure,” I said, still feeling a bit insecure, “please.”
Denise laughed. “Don’t worry, everybody feels a little out of place here the first time. You’ll get used to it soon enough.” She took me by the hand and led me to one of the couches along the walls. “Now, take those clothes off and sit down.”
Denise, who herself was one of the very few people still completely dressed, helped me get out of my shirt and pants. My dick was already fairly hard because of everything that was going on around me.
I sat down on the couch and Denise knelt between my legs. She took hold of my cock and engulfed it with her mouth. She started out gently, slowly sucking the head of my prick. She then increased her pace until my rod was rock-hard. While she was blowing me, she lifted her tits from her shirt. They were nowhere near as big as Debby’s, but large and beautiful nevertheless. What I found most noticeable were her nipples though. These were very large and really hard, sticking out proudly.
After blowing me for a while, Denise let my prick slip from her mouth and put it between her breasts. Putting her hands on her tits, she wanked my stiff cock with her boobs.
While I was enjoying Denise’s attentions, my eyes wandered around the room. Debby was leaning against a wall and getting pounded from behind by the same man I had seen her kissing earlier. With every thrust her giant boobs swung against the wall.
My dad was sitting on one of the other couches with a cute dark-haired girl about my age on top of him. With her sizeable tits in his face and his hands on her gorgeous ass, she was violently riding his huge cock.
Simone seemed to be enjoying herself as well, being pleasured by two teenage boys She was on all fours and she was getting fucked from behind by one the boys while she was sucking the other’s cock.
My mom was in the middle of the room, a centre of attention, something that didn’t surprise me. She was on her back on the floor, with one leg up in the air, while Debby’s father Lucas was fucking her hard. Two other men were kneeling on either side of her and she was taking turns sucking their pricks. While she was blowing one, the other would rub and slap her huge boobs with his cock.
I found it really horny to look at all these people having sex all around me, but turned my attention back to Denise when she stopped massaging my stiff prick with her tits. She got up and, reaching behind her, unzipped her skirt that she subsequently let fall to the floor. Stepping out of it, she revealed her beautiful legs that were clad in stockings and suspenders. She wasn’t wearing panties so I could see that her pussy was covered with a small, nicely trimmed patch of pubic hair. Without bothering to take off her shirt she climbed on top of me, grabbed my rock-hard pole and guided it into her wet cunt.
Throwing her head back, she began riding my cock really hard, groaning loudly while doing so. At first her vigour took me off guard, but before long I was matching her moves with my body and we were fucking in perfect unison. She bent over, moving her head towards mine. “You like this, don’t you?” she hissed at me between groans. “You like fucking an older woman, fucking her and making her your slut. Make me your slut! Fuck me!”
To hear an upper-class woman like Denise utter such foul language while she was enthusiastically riding my cock, aroused me even more than I already was. There was more to come, though.
“Spit on me,” Denise hissed, still riding my prick like a madwoman, “spit on my face! Spit on my tits!”
I thought that to be a peculiar request, but complied nevertheless. I spit in her face a few times and then spit on her boobs. Denise obviously enjoyed this, licking my saliva from her cheeks with her tongue and rubbing my spit all over her tits with her hands. Looking at her doing that, I had to admit this was kind of horny. Getting into it, I spit on her face and breasts some more. Denise continued to ride me hard and I could feel she was getting close to coming as she was groaning louder and louder. When she climaxed, she screamed “oh yeah” dozens of times and so loud that she almost completely drowned out all the orgiastic noises surrounding us.
Her orgasm subduing, Denise sank back on my cock as far as possible, gently rocking back and forth. I could feel her buttocks against my balls. She bent over me, pressing her tits against my chest and gave me a rough, wet kiss on my mouth. “You’re a good boy,” she smiled at me, “now give me some cum.” She climbed onto the couch next to me and lay across me, pushing one of her legs against my face and pressing her tits against my leg. She grabbed my cock and started stroking it slowly, then faster. While she jacked me off, every now and then she bent her head towards my prick and licked the head. It wasn’t that long before I felt I was on the brink of coming. Sensing this, Denise stroked my stiff rod even faster until I finally erupted. A load of thick semen shot from my prick, splattering all over Denise’s hand and boobs. She kept stroking my dick until she had milked the lost drop of cum from it.
“Ah, yummy man-goo,” she grinned and began licking my sperm from her hand and my dick while she rubbed the sticky substance all over her breasts with her other hand.

When she was done licking, Denise opened her mouth and stuck out her tongue at me. It was full of semen. “Now,” she said, “I need a charming wench to share your elixir with.” She looked around, and then said, “Sabrina! Come over here.”
In an instant, the cute dark-haired girl whom I’d seen riding my dad’s dick earlier, appeared in front of us. “Yes, aunt Denise?” she said, the lascivious look in her eyes in stark contrast to her apparently innocent smile. She looked at me with approval. “Who is the young stud?”
I couldn’t help but be flattered by the cute young naked girl referring to me as a ‘stud’.
“Sabrina, this is Joey, George and Nastya’s son,” Denise said, “Joey, this is my niece Sabrina. She’s a horny little slut, but I assume you already figured that out.”
We all laughed. “Now,” Denise said to her niece, “I have some delicious man-goo in my mouth and on my boobs, as you can see. You no doubt want to share this semen with your old aunt.” Denise turned to me. “Feel free to watch. Maybe the two of you will get a chance to fuck later.”
That was certainly an attractive prospect. For now, though, I was content to just lie back for a while and watch Sabrina and Denise swap my sperm. The girl held her head under her aunt’s and opened her mouth. Denise then slowly let my semen drip from her mouth into her niece’s. Sabrina let it roll around in her mouth before swallowing all of it. Then she started to lick my sperm from her aunt’s tits. While I was enjoying the sight of this, I suddenly heard Debby’s voice. “Hello there, Joey.”
I looked up. Debby was standing in front of me, still wearing her red dress. Well, it was more or less draped around her waist by now, leaving her boobs, legs, pussy and ass in full view. Her gigantic breasts were glistening with semen and there were also some droplets on her cheeks and in her hairs. I thought she looked magnificent, the epitome of raw lust made flesh.
“Hello, Debby,” I said, smiling up at her
She smiled back. “Did you enjoy fucking my mom?”
“Yes, it was great,” I said with utmost sincerity, “she’s very enthusiastic.”
Debby laughed. “That’s one way of putting it. I’d say she’s a mad sex-addict slut.” She smirked. “Like mother, like daughter, I guess. Want me to blow you?”
Without waiting for an answer – since obviously there was no need for an answer to such a rhetorical question – she bent over to me, moved her head towards my crotch and took my cock in her mouth, sucking on it eagerly. It was just as great as when she had given me my first ever blow job two weeks earlier. With Debby flicking her tongue over the head of my cock, scraping the length of my prick with her teeth and making loud slurping noises while doing so, my rod was rock-hard again almost instantly. I threw my head back, closed my eyes and just enjoyed the feeling of Debby expertly sucking my prick.
When I opened my eyes again and looked up, I saw my dad coming towards Debby and me, stroking his massive erect cock that was glistening with pussy juice of no doubt several different women. He halted behind Debby and smiled at me. “Enjoying yourself, son?” he asked.
“Yeah,” I moaned, “definitely.”
“Yes, Debby is one hell of a cocksucker,” my father grinned, “but she’s got a wonderful tight pussy as well, as you know.” My dad positioned himself behind Debby, slapping her wonderful ass with his hands and guiding his prick into her cunt. He immediately began pounding her hard, putting his hands firmly on her butt.
Debby began to rock back and forth because of the hard fucking my dad was giving her, but bravely managed to keep her mouth locked on my cock. It did make her cocksucking more erratic, but no less pleasurable and the sight of her giant, sperm-covered boobs shaking to and fro was a joy to behold.
My father was fucking Debby even harder now. Her tits were thumping against my legs and she clearly had trouble keeping my prick in her mouth, until she finally let go of it and grabbed it with a hand instead, stroking it fast and hard.

When I felt I was about to come, suddenly a bell rang several times. Debby instantly stopped stroking my stiff prick and I noticed my father abruptly halted his pounding as well, letting her cock slide out of Debby’s pussy. Looking around, I saw that all sexual activity had come to a halt. I saw Denise standing in the middle of the room, completely naked now, with a small bronze bell in her hand that had apparently been the source of the ringing. Everyone in the room turned to her.
“Friends,” Denise said, “it is great to see you all enjoying yourself and I am somewhat sorry to interrupt all this wonderful wantonness. But, as most of you, it is now time for the ritual known as the queen of the circle.”
Now that was a surprise. Nobody had bothered to inform me about this ritual. I wondered what it could be.
“Being the host of today’s meeting,” Denise continued, “it is my duty to appoint today’s queen.”
Applause followed. I was really getting curious as to what this was about now.
“I have watched many of the women in action, so to speak. It was hard to select today’s queen, as you are all such magnificent sluts.”
More applause.
“However, as always there can only be one queen. And today’s queen is . . . Nastya.”
Yet again applause followed and my mother came forth, joining Denise in the middle of the room. She kissed Denise on the mouth for a long moment, both women fondling each other’s tits and asses in the process. This was, of course, met by more applause.
When my mom and Denise let go of each other again, Denise spoke again. “Ladies and gentlemen, I give you today’s queen. Let the ritual commence!”
More applause yet again. I turned to my father, who was clapping like everyone else. “What is this about?” I asked.
“You’ll see,” my dad grinned, “and no doubt you’ll like it.”

Denise stepped away from my mother, leaving her alone in the middle of the room. She knelt down and looked around. “Well, then, gentlemen,” she said, in that horny lilting accent of hers, “give it to your queen.”
All the men stepped forward now, forming a circle of some twenty men around my mom. They were all stroking their cocks. While I joined them, standing in the circle between my father and a boy my age whose name I couldn’t remember, I was beginning to see where this was going to lead.
Before long, the other women turned their attentions to the circle of men, stimulating them by stroking or sucking their dicks. Denise turned her attentions to my father, slowly sucking his rod. Debby was masturbating a middle-aged man on the other side of the circle. To my pleasant surprise, Sabrina, the cute dark-haired girl whom I’d already seen in action with my dad and later with Denise, came up to me. “You want me to help you with that?” Sabrina smiled, nodding at my stiff prick.
“Please,” I smiled back, taking my hand off my member.
Sabrina knelt in front of me and started to suck my cock. It was obvious she wasn’t as experienced as Denise or Debby, but what she lacked in technique she made up for in youthful enthusiasm. I put my hands on her head and began actively mouth-fucking her. She coped very well.
While I was enjoying Sabrina’s blowjob, I couldn’t take my eyes off her nice big tits. “Hold it,” I said, “retracting my erect rod from her delightful mouth, “I want to fuck your titties.”
I grabbed my prick, slapped her boobs with it a couple of times and then stuck it between them. Sabrina pushed her tits against my dick, smiling up at me, while saliva mixed with my precum was dripping from her chin. Pushing my cock back and forth between her young fun bags felt great.

By now, it was obvious that a lot of the men were getting close to coming. The boy next to me, who was having his cock sucking by a charming woman in her forties, was the first who couldn’t hold back anymore. The woman, noticing this, let go of his rod and the boy stepped forward towards my mother. He reached her just in time before his young sperm spewed forth from his dick, hitting my mother in the face and splattering her nose, lips and chin with semen. My mom stuck out her tongue and licked some of it from her lips.
The boy was hardly done ejaculating before the next man stepped forward. It was the
man in his mid-forties who had been fucking Debby at the start of the orgy. He blew his load all over my mom’s gorgeous boobs, covering her tits with sperm.
Next was one of the teenage boys I’d seen fucking Simone earlier. He shot his semen all over my mother’s forehead, from where it dripped down all over her face.
Debby’s father Lucas stepped forward next, shooting a huge load over my mom’s boobs. Another stepped forward, then another and by now my mother was becoming coated in cum. Her face and boobs were almost completely covered with semen, but from there it was trickling down her whole body.
Now that her face and tits were covered, some of the men also began targeting other parts of her body. One blew his load on her belly, another one shot his sperm all over her magnificent ass.
I was still tit-fucking Sabrina while I was watching this spectacle and I felt I wouldn’t be able to contain my load much longer. I stopped fucking Sabrina’s breasts, grabbed my prick and, stroking it, stepped forward as well. My cum-covered mother smiled up at me, waiting for her son’s load to be added to the many she had already received.
Stroking my dick a few final times until I felt my orgasm coming, I aimed my rod at my mom’s tits. I exploded and ejaculated thick blobs of sperm that splattered against my mom’s already sperm-covered tits.
When I was done, I stepped back again, watching my father take my place. He was the last one to offer his semen to today’s queen of the circle, which was fitting of course since today’s queen was his wife. Aiming his prick, he shot a huge load of sperm on her cheeks and shoulders.
When he was done, he stepped back and my mom got up. Semen was now almost streaming down her entire body. It was a magnificent sight to behold.
My mom took a small bow and said, “your queen thanks you.”
This led to another round of enthusiastic applause.
Denise stepped forward again and stood next to my mom. “Friends,” she said, “this concludes the ritual of the queen of the circle. And what a queen she is!”
More applause followed.
“Now,” Denise continued, “let us continue where we left off before the ritual.”
Again, more applause. This time, it died down quickly though and within a few moments, most people were already engaged in various sexual activities.
I felt a bit tired, but when the charming woman in her forties who’d been sucking the boy next to me in the circle came up to me, enquiring if I would like her to blow me, my cock began to rise again almost instantly.
While the woman began sucking my prick, I could only think about all the wonderful women in the room I hadn’t fucked yet and wondered how many I would get a chance to fuck before this meeting would be over. So much more glorious debauchery awaited.

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Having Fun With The Babysitter and her Boyfriend

“Okay, Samantha, we’ll be gone for about four hours. Once you put Lauren to sleep you can call your boyfriend to come over. But, I don’t want him here until our daughter is asleep.” “Don’t worry about anything. Everything will be fine.” “If you want to go into the pool, just bring the baby monitor outside so you can hear the baby in case she wakes up.” “I have your phone number in case of a problem. Go have some fun you both deserve it.” My husband Jerry and I left to go out to dinner with...

Group Sex
3 years ago
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Thats My Babysitter In That Porn Video

Following my divorce, my company transferred me across the country and the custody agreement with the ex allowed me to have my daughter for six months then she would go back to her mother’s place on the West Coast for another six. I had a deadline rapidly approaching and desperately needed some uninterrupted time in my home office to complete my reports. I called my usual babysitter and she apologized but had accepted another job for the evening. I explained my situation and asked if she had...

Straight Sex
4 years ago
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Dont Tell Mom The Babysitter Feminizes

Don't Tell Mom the Babysitter Feminizes! Written by Courtney Captisa Edited by Sally Bend "It's so nice to meet you!" smiled Jessica, the skinny 18-year-old brunette girl at the door of the McLandon household. "Please come in!" said Ms. McLandon, waving Jessica, who was carrying a large backpack, in from the front door. "My sister has told me very good things about you," she added, referring to Jessica's babysitting skills. Jessica had been working for her sister for over a month...

3 years ago
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Spanked By My Babysitter 4

I still keep in touch with my babysitter Lori. I'm in college and it seems that she thinks I need her to keep me in check because of my behavior. She always promises me discipline punishment and spanking to keep me from screwing off. To refresh the memory, Lori is about seven years older than I am and she has been my babysitter for a long time. I am now nineteen and in my freshman year of college. Lori about twenty-six years old.Lori gives me the usual discipline punishment and spanking routine...

Spanking
4 years ago
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The Punishment of the Babysitter

Jenny was almost 16 and had never had a boyfriend or even kissed a boy not even held a boys hand. She was the daughter of a single mother who had become very obsessed with her church after getting pregnant very young. Her mother would not divulge the name of her father and Jenny had even snuck a peek at her birth certificate and under father it said None. After getting involved heavily in her church her mother never dated another man and she intended to isolate her daughter in the same manner...

3 years ago
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Bobby Becomes Pussy the Babysitter

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...

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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The Babysitter

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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The Babysitter Chapter Two

Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women of the neighbourhood. Some I would wash and return, others I kept as souvenirs. It began to grow beyond just panties, babydolls, bras and basques. I began completely to dress in a feminine fashion...

4 years ago
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The Babysitter and the Nudist Campers Chapters 1 3

Little Dolly Packer hadn’t been a babysitter very long. In fact, she had only started to babysit for money the previous month. Her father was away on a long sea cruise earning much needed cash for the family of five. She and her three other younger sisters were a burden on their sickly mother’s shoulders and Dolly did her best to help out with the earning of income to put food in their mouths and the rent inside her mother’s purse for the dreaded first Friday of every month.Dolly was still a...

Group Sex
2 years ago
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When The Babysitter Came

"Andrea, Susan, can you two come down here for a minute?"I heard mum calling us and felt my cheeks flush angrily. I know Susan was still young but I wasn't a child anymore and didn't want to be treated like one."Andrea, don't start young lady, my taxi's here." The neutral tone couldn't hide her impatience and I could picture her looking at her watch whilst standing at the door, waiting for me to show myself. Knowing she wouldn't leave until I'd done as asked, I resignedly sauntered to the top...

Voyeur
3 years ago
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An Unexpected Threesome With The Babysitter Part Two

A month passed since my wife and I had sex with our babysitter. I couldn’t stop thinking about that amazing night. I know it’s very wrong, but I have to be with the babysitter again. I haven’t told my wife about these thoughts. I don’t want to cheat on my wife, but I cannot forget the feeling of fucking Sandy’s young pussy. I have had dreams about her body and how it felt to be inside of her pussy. I don’t want to share Sandy with my wife ever again. I want to have sex with her all by myself....

Group Sex
4 years ago
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The Babysitter Chapter Two

Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women of the neighbourhood. Some I would wash and return, others I kept as souvenirs.It began to grow beyond just panties, babydolls, bras and basques. I began completely to dress in a feminine fashion...

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...

3 years ago
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Our Babysitter Watches Us

I met Tracy my senior year at The University of Texas in Austin, what we all considered to be the 'real' U of T. She was a year behind me and was also a business major though she was headed to finance and I was aimed toward marketing and advertising. So, she was a numbers drone and I was a 'flack.' Obviously, we immediately kidded each other unmercifully then proceeded to fall in love. One thing about Tracy that wasn't immediately apparent was that she loved sex, she just couldn't get...

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...

4 years ago
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Blonde Mom Fucks Black Babysitter Pt 1

Introduction: This series will include the babysitter fucking mom with a strapon. Like so many times before Loren Wright had picked up Alex her babysitter. Loren was a 32 year old single mom, but still gorgeous with shoulder length blonde hair, a slim tight body and a perky ass that didnt show a hint of sag. She also had firm breasts that were small still firm and round. Loren was also a lesbian so didnt mind giving her babysitter a ride as the fourteen year old was so hot Loren got a thrill...

2 years ago
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Babysitter Makes Her Move

Ashley chose her outfit carefully. She wore a simple white blouse with buttons. It was tight, but Mr. Brenner couldn't tell since she kept her sweater on till after he left. Her skirt was loose and short--well above the knees. She decided against a plaid, thinking it was cliché and, instead, went for bright blue. She completed the outfit with a pair of pink ankle socks. She was going for a look that was both innocent and sexy--just short of slutty.And she succeeded beautifully.At the same time,...

4 years ago
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my babysitter my teenage whore

My wife and I had been married for five years and had some good sex before our twin daughters were born, then our life in the bedroom began to taper off some.It wasn't that Lisa wasn't attractive any more; she was hotter than ever with the few extra curves she put on after she had the girls.I don't know if she was self-conscious about the ten extra pounds she had on herself or worn out from the girls, but she didn't seem as interested in sex as she used to be.On a good month, I may have gotten...

3 years ago
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Our Babysitter Julia

“So what time does she get here?” I asked, my wife then checked her watch and then looked up at the clock. “In about an hour.” she replied. “Why check your watch and then the clock?” I asked her, “Didn't know that was the time.” she answered. I continued tapping keys at my laptop while she got dressed. She was a beautiful woman, with short curly black hair and a size 8 figure. Her breasts were natural, which some people didn't believe because they were so pert. Sitting like two half...

3 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...

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...

3 years ago
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Babysitter Gets Caught Then Gets Schooled

Introduction: Kayleen is one that likes to be in everyones business- like booze. But after Jimmy and Beth Lawson catches their babysitter in the act, they teach her a painful & valuable lesson. But its the lesson that will forever stick with her for the rest of her life. Beth and I have been married now for twenty years, and still going strong. You could say that were a loving, warm-hearted, deeply passionate couple. We couldnt have asked for anything more, a nice home, three beautiful kids. In...

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...

4 years ago
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Babysitter Gets Dismissed Then The Anniversary BreedingTaboo Begins

Introduction: After Kayleen got schooled and dismissed, Jimmy & Beth teaches the twins how to fuck a REAL woman. FROM THE AUTHOR: This is really the fourth & final installment of Babysitter Gets Caught, Babysitter Gets Schooledseries. After Kayleen leaves, thats when the twins decided to help breed their mom. So their dad teaches the pm a lesson on how to seduce an older woman. Be sure you read the EPILOGE at the end of this story. There might be a spinoff, depending on the reviews. Thanks and...

2 years ago
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Our Babysitter and Her Mother

Our Babysitter and Her Mother By Wonder_Dad - Story #11 - Downgraded AgainThroughout our marriage, the wife was getting restless wanting time alone, either with me or with her girlfriends. I placed an ad in the local newspaper seeking a babysitter. I thought we would be swamped with responses, but after two weeks, there had been only one call. We had decided to interview all candidates in person, before making a choice. We met with the young lady, but she was really way too young, barely a year...

2 years ago
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Babysitter Worth Keeping 12

Babysitter Worth KeepingBy Wonder_Dad - Story #12It was quite a stroke of luck after attempting to find a babysitter that would satisfy our requirements for our two k1ds for so long. The girl, Justine, a young girl of 17, whose jet-black hair complimented lily-white skin, was finally hired. I knew little of her, but was learning quickly thanks to advice of her mother, Tatyana. Justine was truly a carbon copy of her mother in looks, but not in actions. I will not digress and re-tell my previous...

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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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 Sins of a Submissive BabysitterChapter 2

Six full months have passed since the new babysitter entered into the household of the most esteemed Reverend John Stiffworthy and his somewhat flirtatious and definitely disobedient wife Gloria. The Reverend’s move to the smaller and more isolated parish was at the request of the Bishop until the dreadful rumors about things of a sexual nature with the Boys’ Choir had died down sufficiently for him to return to the center of the church’s headquarters without controversy. It was actually...

1 year ago
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Bedding The Babysitter 3

Note 1: All characters are at least 18 years old. Note 2: Although I recommend you read parts 1 and 2 first, here is a summary of this series so far... Part 1-Megan, a dominant but caring lesbian, seduced her cute and innocent babysitter Jenny. Part 2-Megan takes her new submissive lesbian shopping, makes a fantasy come true with a cheerleader that Jenny had dreamed about forever and took her to a special lesbian only bar. Bedding the Babysitter: A Cheerleader's Recruit What a weekend. Jenny...

Lesbian
3 years ago
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Hot Babysitter part1

I was in desperate need of a night out so I asked my husband if we could get a babysitter for the boys and go to dinner. He happily agreed and called the neighbors to see if their daughter, Susie, was available. Thankfully she was so we set it up for Saturday night. Saturday came around and I was more than ready to go out and look sexy for my hubby. I chose a short black fitted dress that hugged my hips and was low in the front to show off my C cup tits. I threw on some 4in black heels and let...

4 years ago
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Hot Babysitter part1

I was in desperate need of a night out so I asked my husband if we could get a babysitter for the boys and go to dinner. He happily agreed and called the neighbors to see if their daughter, Susie, was available. Thankfully she was so we set it up for Saturday night. Saturday came around and I was more than ready to go out and look sexy for my hubby. I chose a short black fitted dress that hugged my hips and was low in the front to show off my C cup tits. I threw on some 4in black heels and let...

Bisexual
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...

3 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...

1 year ago
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Somebody Had To Take The Babysitter Home

Mike’s night was falling apart.“But honey, this is supposed to be a romantic evening with,” he struggled to phrase it with finesse, “an intimate ending. How are we supposed to do that if you end up falling asleep before I get back home? Can’t we just call her a cab?”His wife, Cindy, sighed in response. “Sweetie, someone needs to bring Megan home, and I’ve had too much wine, so it’s going to have to be you,” she explained as she looked at him with a face depicting the annoyance of telling a...

Oral Sex
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
2 years ago
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The Babysitter II

The following is a continuation of the original story "The Babysitter" previously published on this site under the Taboo category. If you haven't read the original story, please do so before reading this one, as it will introduce the characters and circumstances so this one will make more sense. * The extra week that my wife was gone stretched into two. Amy had gone to her sister's to help her while she and her husband were having troubles. They had split for a time, and Amy's sister was...

Taboo
2 years 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...

4 years ago
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Missy My Babysitter is A Horny Little Slut

I couldnt believe I was staring at a picture on my computer of my 18 year old babysitter's naked pussy. Leaning back behind my desk in my home office, maximized on my monitor, was a picture of Missy lying on her back nude with her legs spread, and a perfectly shaved, glistening pink pussy pointed at the camera. Wow. I mean -- wow. It was the second of the fifteen pictures that I'd opened. The first pic, ME, had a nice smiling photo of her sitting on the bed wearing a bra and panties. And, of...

3 years ago
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Jessicas LiveIn Babysitter Part 1

Jessica's Live-In Babysitter - Part 1 by CutePatti ________________________________________ Sam had doubts about Becky's idea when she had broached it to him over lunch at the office. Sam and Becky had known each other for many years and had even had a serious relationship at one time. But that was long over and they were able to remain friends since they worked for the same company. "I have a problem," she said, "and I think you're the perfect solution!" She went on to explain...

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...

2 years ago
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The Babysitter Rules

Jessie Flanders checked the time on her cell phone as she neared the elegant Carter home. She was a minute early for her babysitting job. As she made the turn onto the Carter’s front walk, a cab pulled to the curb and blew its horn. She reached the door and was about to ring the doorbell when it popped open. A good looking woman in her late thirties dressed in dark slacks and sweater peered at her over her glasses. “Are you the babysitter?” she asked. “Yes I am,” Jessie said. “The sitter’s...

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...

2 years 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...

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...

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...

3 years ago
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Hypnotizing the Babysitter Ch 01

This is a chronicle of the most important two weeks of my life. First things first, though. I should warn you about this story. For, while the title is certainly accurate… and while this tale really IS about me hypnotizing the babysitter… and while it really IS about how this girl’s head was filled with all sorts of enticing and passionate suggestions… and while it IS about how these suggestions led her to engage in extremely arousing and exotic sexual relations with me… I feel obligated to...

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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The Babysitter III Question

I awoke the next morning after a night of intense lucid dreams with no recollection of how I had ended up in my own bed. All I remembered was venting my unmet desire to get laid with a quick, loveless wank. It took me a while to realize Emily had come to my room to wake me up.She was gently rubbing my cheek with the back of her hand when she spoke, “Rise and shine, sleepyhead. Breakfast is ready?”I looked at her through half-closed, drowsy eyes and mumbled something unintelligible about...

Teen

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