Twin Babysitters II: Shelly

by Jodi Sylph

  Twin Babysitters II: Shelly

  By Jessica Longstreet & Jodi Sylph

  Published by Jodi Sylph at Smashwords

  Copyright 2012 Jodi Sylph

  Smashwords Edition, License Notes

  This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each recipient. If you’re reading this book and did not purchase it, or it was not purchased for your use only, then please return to Smashwords.com and purchase your own copy. Thank you for respecting the hard work of this author.

  This is a work of fiction. The people, events, and circumstances depicted are fictitious and the product of the author's imagination. Any resemblance of any character to any actual person, whether living or dead, is purely coincidental.

  Mark woke up before Chris, made a pot of coffee and checked the baby. He was awake and playing in his crib. He got the baby out and started his day, waking Chris up later than normal since he had the day off.

  Chris came out of the room looking hot as ever and Mark wished he had time to indulge this morning, but not today. He had lots to do, and they needed to get the baby ready to take him for his checkup. They were ready and out the door at nine, and when they got home later that morning Mark reminded Chris of the Party that night.

  “Don’t forget, we’ve got to get a veggie dish for the party, and find a good bottle of wine.” And with that Chris was out the door. He was going for the trifecta today, and he picked up his phone and walked to the calendar. He suddenly couldn’t remember which one of the two numbers he called and reviewed his call history, 4828. So, since Sherry’s sister was coming over tonight to babysit, he dialed 2848 and listened to the ring tone.

  “Hello, this is Shelly.” A voice said on the other end of the line.

  “Hello Shelly, this is Mark… your sister Sherry told me you could babysit tonight?” Mark crossed his fingers.

  “Oh Hi, Mark. Sherry told me she had a great time last night and I could definitely use the money.” As soon as she said that Mark thought, Yeah, I bet she had a great time.

  “Good, then I suppose we’ll see you around five tonight, eh?” Mark asked. They worked out the details of dinner plans and then Mark asked her, “Would you just like to crash on the couch? We’re not going to be home until after two a.m.”

  Shelly had talked to Sherry, but Sherry didn’t mention what had happened at all, instead she had said it was a really nice house with all the channels you could ask for and it was an easy job. The best part Sherry told her about was the hundred bucks she’d made.

  “Well, I’ve got to call Sherry and tell her what I’m doing so she doesn’t wait up for me…. but yeah, I think I could do that.”

  Mark told himself that he would make sure he made it worth her while, to tempt her that much more. There was every possibility since this was a new babysitter that she would have to be recorded, of course. He thought how clever he was and smiled deviously.

  “Sebastian will be up when you get here sweetheart, so make sure you’re ready to play with the cutest baby ever!” he said.

  The broke off the call and Mark went to set up the camera. He dug in his drawer and found a bigger memory card, he wanted to make sure it would last until they got home so he wouldn’t’ miss anything, if anything happened.

  Shelly hung up the phone and went back to her pussy. Her sister had come in last night and disrupted her, and she never got the chance to finish, and so while her sister was at class this afternoon Shelly worked at fixing that problem.

  Oh she was good at it too, she knew she was. She teased open her pussy with her fingers and pushing in three at a time. She hated having her sister always around, and they made a point of taking breaks from each other. It was a long walk to Sherry’s two hour class so she had plenty of time to take care of her aching pussy.

  She loved wearing nylons while she fingered her cunt; it made her feel slutty and trashy. She crammed her fingers into herself and then licked her fingers to taste herself. Her puddle of cum, as she called it. She always made a sizable puddle when she touched her pussy.

  She had been watching some stupid soap opera type show on the public channel, and the only guy she could picture herself fucking was this Doctor character. He was older, but he was hot. She kept looking to see his crotch, and when she caught a glimpse of it she would think how she’d tell him to break that dick out so she could suck it. She loved sucking dick, just like her sister, and she knew her sister was almost as big of a slut as she was.

  Shelly rolled over so she could scream into her pillow as she came, thinking about the doctor on the TV. I am such a dirty little cock slut, she thought. Her pussy dripped and her hand was covered in the sticky cum. Again she tasted it, so damn yummy to taste her own pussy. She wondered if the doctor would lick her snatch and then kiss her. Yes… kiss me Doctor.

  She imagined the doctor giving her an examination, and of course she only wore one of those hospital gowns. She could see herself answering the questions the doctor had.

  “Alright Shelly, you’re a female, and almost nineteen years old.”

  “Right,” Shelly said.

  “Well, let’s have a look, open up your mouth and say ahhh…” the doctor said in her vision. She stroked the inside of her cunt with her hand now, all four fingers diving into her splashing pussy. He used his dick as a tongue depressor, and then she clamped her lush red lips over his dick and slurped on the entire length of it. If she had a problem with her throat, the problem was she needed cum running down it. Her eyes were closed and she licked her lips imagining getting to suck a dick right now… any dick right now.

  “Fuck me Doctor,” she said as she rode her hand again cumming and splashing it all over her bed. “Oh please put it inside me, Doctor, I need my temp checked…”

  She stopped full stride. Wait….that was a rectal thing. She thought about it for a second and then dropped her hand over her ass and ran it down her ass crack.

  “Yes doctor, come and take my temp, I’m sure I’m hotter than I should be. She tore a new hole in her nylons, and started toying with her asshole. It was hot to her touch alright, and she felt it contract as she tried to put her finger inside of it. So tight, she thought. Her pussy gushed again, more cum, her eyes crossed behind her lids, and she pushed the final knuckles of her middle finger into her ass with one long hard push.

  “Oh fuck me….” She was experiencing her first anal orgasm and it swept over her like a sudden summer storm, leaving her hot sticky and wet. “Fuck me doctor, put it in my little tight asshole,” she said as she pulled her finger all the way out of her ass. She put it in her mouth to make it wet enough to put back in her ass. It’s still too dry, she thought.

  She turned her head to the night stand and grabbed the jelly. It was cold on her ass cheeks, but she rubbed it in and pulled her knees up under her chest, pointing her ass straight into the air. She rubbed the ass crack a few times, spreading the lube all over her ass. When she looked back, she could see it soaking into her nylons, but most of her ass was now fully exposed from the tear, and the rip from her pussy had joined in with her ass, showing the glistening skin of her thighs.

  “Put it in my ass, Doctor,” she said, and pushed two fingers into her ass. She felt her pussy open up and literally drop cum out of it. She looked down and saw her juices on her sheets, and she stopped playing with her clit with her other hand and scooped up the drop of cum with her fingertips and smeared it on her lips and licked it off. “Deeper Doctor,” she said as she forced her fingers deeper into her asshole. Her other hand went back to her pussy now almost abusing her clit rubbing it
rough and hard, pressing it against her pelvic bone to almost make it hurt.

  “More, Doctor!” she screamed into her pillow, her mind now seeing the doctor in the break room, fucking him while other doctors watched with their masks on so she couldn’t see their faces. She pushed her third finger into her ass, and that’s when she finally collapsed and soaked her sheets one last time for this session. She wiggled around in her puddle and rolled over, lightly running her hand over her bald mound. Such a tiny little pussy to need so much attention, she thought. Now her ass was going to want shared attention too.

  She checked the clock and saw she needed to get a shower and get around to Mark’s house. She got up and pulled her top sheet off the bed and tossed it in the laundry. Thank god for free student laundry.

  She got out of the shower and dried herself off. She already knew what she would wear today, she had a cute little plaid skirt and it was just warm enough to wear it still. She put stockings on that went over the top of her knees, and had cute little pink bows at the top of them; she wore a tiny thong that slid between her ass cheeks and then barely covered up her little happy spot.

  She pulled up her skirt to see how her pussy looked. Fantastic! The thong was bright pink, and she had to feel the mound of her pussy against her panties, so she pressed her hand down and rubbed it, just long enough to feel her clit waking up and getting aroused.

  “That’s better, you better be ready to go at the drop of a hat.” She slapped it lightly and threatened it, “Don’t you lay down on the job again.” She laughed at herself and then started her makeup and hair.

  As soon as she was done she stepped back, taking all of herself in. She looked illegal, just the way she liked it. It was ok to look illegal, as long as she had her license with her.

  “Eighteen, baby, suck that!” She grabbed her crotch like a ballplayer and then made a fucking motion. “I can do anything I want now.”

  She turned and walked to the door with her back pack slung over her shoulder. She looked like one of those anime characters, a really slutty one, she thought.

  She pulled the door behind her and walked out of her dorm.

  Chris was already home, and he and Mark played with the baby when the doorbell rang. Chris immediately sat up and Mark went for the door. He had been thinking about Sherry all day long, and Mark had too, but it was Shelly, not Sherry. Mark met her at the door and introduced himself, then remembered he hadn’t told Chris about Shelly coming instead of Sherry. When Mark brought her to the nursery, Chris smiled at her outfit.

  “Well hello, Sherry,” Chris said. “How are you doing tonight?”

  “Oh, Chris, this isn’t Sherry, this is her twin sister Shelly.” Mark was saying something else, but the thought of Sherry having a twin sister was already working its magic on Chris’s dick. It was starting to not just wake up, but starting to really move under his khaki’s.

  “Hi, I hope you don’t mind me filling in for Sherry, she’s got a class this afternoon and couldn’t get here by five, but I was open to come over.” She was talking sexy already, ignoring the fact that either of the men were gay and in a relationship.

  It’s a good thing I got Sherry first, Mark thought, and then showed her around the nursery. Shelly kept shifting her ass under her skirt, teasing Chris, and she picked up on his stares right away. It took her a little longer to see Mark doing it, but she caught him looking at her chest and down her shirt a few times even. Shelly was a menace when it came to men, she could distract the best of them, and her talent was clear to see compared to the innocence of Sherry.

  The couple talked to her a little bit longer and then came back to the living room with the baby and some floor toys. They said goodbye, kissed the baby, and left. Sebastian never even made a noise because they left. He seemed to be completely happy playing and rolling around on the floor.

  Mark had told Shelly to put Sebastian to bed at seven, because he slept all night long. She sat and played with him and didn’t even notice the time when she missed his bedtime.

  “Shit,” she said, and then corrected herself, “Sorry Sebastian, I mean crap. I’ve got to get you to bed, little man.” She picked him up and took him to the nursery. She tucked him in and read him a story and sure enough, out like a light two pages into Sam I Am.

  Wow, that was easy, she thought. She checked the rest of the house quickly to make sure it was all good to go, and went to the couch and grabbed the remote. When she sat down, she sat with her legs sprawled, one on the arm of the couch, the other almost touching the floor, her skirt wasn’t covering much at all. She used her hand to trace her slim pantie-line below her skirt. She inched her fingers closer and closer to her pussy, and looked for something to watch that might encourage some play time. She was going to be here for hours, and even spend the night.

  She wasn’t even really trying to find something, just skipping channels until she saw some hot guy with his shirt off. After all, it would be much better than the soap opera doctor guy, and she came hard. She thought about her ass too and it occurred to her… she was in the house of two very attractive gay men.

  She got up off the couch and walked to the wall with their pictures. They were obviously in love, and her eyes scanned the pictures, the fourth picture she looked at featured them bare chested.

  “Abs and pecks,” She grabbed the picture off the wall and walked back to the couch. “Now boys… let’s see the two of you come fuck me.”

  Her mind started contriving the images of the two of them on a beach, they were making out, both of them tanned and so sexy. Chris moved down on Mark and Mark was turning his head to the side to moan, and he saw Shelly walking towards them. Her eyes were closed now and she was picturing Mark tapping Chris on the head to get his attention and point out the sexy blonde striding towards them. Chris pulled his mouth off of his partner’s member, and beckoned her to sit on Marks dick.

  She did, she straddled Mark and slowly lowered herself onto his erection, letting each inch settle into her pussy. Chris was looking at her and then said…

  Her phone rang, and she almost had a heart attack. She got up from the couch and went to the table where she had left it. It was her sister.

  Sherry wanted to know how babysitting was going, and she told her it was a piece of cake. She tried to break off the call.

  “I can come take over for you now if you want me too?” Sherry said, remembering about her ride home with Chris, and the good fucking he’d promised her.

  “Uh… Mark asked me to spend the night since it was going to be so late. He said it was fine and even offered to pay me more money if I could do it.” Shelly was crushing her sister’s vision of fucking a gay guy.

  “Oh… well…. alright. I’ll just hang out at the dorm then unless you want some company?”

  “I’m actually ok, you can stay there if you want,” She didn’t tell Sherry that looking forward to a night of just stroking her own pussy in this private lush setting. “I don’t mind being alone tonight, and they’ll be home by two or three.”

  Sherry was furious inside, she thought her sister would just let her take over when she got all done with school and finished her homework. Instead she was being a little bitch, and hogging the rich guys to herself. She was so damn jealous.

  “Make sure you tell Chris you’re not me, ok sis?” she said and then she hung up the phone abruptly.

  “What the fuck was that about?” Shelly held the phone away from her, and said it to the phone like it had slapped her. “How rude… bitch!” She was allowed to call her that, it was her sister.

  Still, what did Sherry mean; make sure you tell Chris that she wasn’t Sherry? She was probably hung up on him already; she always fell in love too quick. Chris was gay… gay! You don’t’ come back from gay…

  Or do you?

  Sherry sat at home, pouting. She’d been looking forward to this all day long and now she wasn’t going to get the reward she had been thinking about all day. She thought to herself, I wonder… what
can I do to still make this happen? She went through her phone and found Marks number. She tapped her lip contemplating what to tell him to let her stay there, but nothing came to her mind. She lay down on her bed and kicked her feet like a little girl.

  “Bitch…” and then she turned on the TV and started watching some stupid soap opera with an old doctor guy. It wasn’t long before she drifted off to sleep.

  Shelly was having the time of her life imaging all night long about the men fucking her this way and that way, here and there, on a beach and on an airplane, and her pussy couldn’t get enough.

  “They’re gay…” She let that thought stir in her mind. She got up and went to their room and turned on the light. It was pretty fucking nice, huge bed, and double walk-in closets and a master bath between them. She went to the bathroom first and opened the medicine cabinet. She was looking for lube to try out her asshole again, but she wasn’t having much luck.

  She didn’t look too deep because she wanted to make sure she didn’t disturb anything, or arouse suspicion that she was trying to steal something, she just wanted to find something to play with her ass, but then she found it. In the bathroom on the top shelf was a hat box.

  She reached up and grabbed it and it felt pretty heavy. She opened up the lid and she said “Bingo!” It was full of anal toys, nicely organized and clean, and there was a huge tube of lube. She took the box with her back to the living room and looked through the toys. At the top was a double dong they must have loved playing with.

  She pulled it out and felt her pussy quiver and drip. The dildo was huge, and she didn’t think it would fit in her little ass. She needed to find something smaller. She kept looking and feeling each toy until she found a small butt plug.

  She took it out and sat the box on the coffee table, grabbed the lube out of the box, and squeezed some into her palm, pulled her thong to the side and then started lubing up her ass, inserting her middle finger to test for how easy it would be. Nice and easy, she thought, and tensed as she pressed her second finger in.