Cassie the Contortionist

Author: stoneypoint
Published: Oct 31, 2008
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Cassie, Mary and Chet's babaysitter is incapable, but when Chet comes home to see what her problem is, she opens up and tells him or asks him things that should not be said. Eventually she gets him to really "open up" to her.

She called once and Mary answered it. She wanted to know how to work something. It was the microwave, she couldn't be that dumb I said, but Mary just snickered nodding her head. 20 minutes later she called again and again Mary answered the cell phone. She needed to know where the extra cash was because what they cooked in the microwave was overcooked. 10 minutes later the poor girl called, she wasn't sure how much to tip the delivery guy. Mary tried nicely to scold the young lady, but I felt she needed some help. I pulled it away from Mary and got on the phone and explained we were trying to enjoy ourselves that night.

Cassie broke down and started crying on me. She wasn't a very good babysitter she said. I told her she was doing fine and she'd learn from all this, but I knew she wasn't the brightest apple in the bushel. She came as damaged goods, but had been trained in a couple things. One of them being a babysitter and the other was she was learning how to cut hair. Her crying got worse. I tried counseling her as best as I could and I began not trusting this young girl as we spoke.

Finally I said "I'll be there shortly." I took a cab home and she was waiting by the front door. Her eyes were wet and it was apparent to me she didn't really like babysitting at all. Seeing as the kids were pretty young, she put them to bed early. I felt it was a bit too early, but I left her to make that judgment call.

Cassie's a cute girl looks about 14, but she was actually 18 to my dismay. She'd follow me around that night like I was her master and I kept wondering why she followed me like a lapdog. Oddly she wore a cheap blouse and tight ass jeans. To me the getup was over done. But I figured she wanted to make a nice impression on us; that was until she told me something while we were in the kitchen.

"You think I'm a lot younger, don't you" she said. I turned with an inquisitive look on my face. "You do, don't you" I shrugged my shoulders not sure what to say. Then she said in a bouncy voice, but without a smile "That's cool most men will. But I'm not you know. I bet you have no idea do you" she said. I shook my head. I remained quiet. She said it was cool. She said "I bet if you saw my titties and if you saw me in a bathing suit or whatever, you'd still think that. Most men do you know."

I started to get a hard on. It was only a little one. Not some full fledged raging mad erection, but I felt my dick tingling. I heard myself saying how it would be interesting to see her little titties, not that they were puny, but in comparison to her real age they were small.

"We don't have to have... we don't need to talk about that" I told her as I shook my head trying to divert any conversation away from her desires, sexuality, and her tiny taut body. Cassie had tiny perky boobies, a petit figure, but an ass that was so tight it would have been impossible for anybody to put a cock up inside it. She looked away knowing her remarks weren't proper and said she was sorry. She apologized. "It's gonna be fine" I added as my penis stiffened and the tingling mounted.

I did want to see those puny nipples of hers. I did want to see her tiny cute titties. I couldn't tell her so, but I did. She became more cheery, friskier, and easily opened up to me about all things.

"I've had boyfriends, lots of them you know, but I guess you'd know that huh" I shrugged my shoulders as if I didn't care. "I have you know. Some my, some older, much older, and some... well a couple lots older then me but not that much older."

I caught her looking at me, my body. I felt a wave of arousal flow through me. I felt embarrassed how she looked at me. I was 34. She was only 18. She had been 18 for several months at that point. But she didn't look like it. No, she didn't. She looked like she was at best, 14, and that was the part I had trouble getting over.

We stood there, in complete silence, but her eyes were locked on me or nearby me. She made me feel uncomfortable. She made me feel like I was doomed. Her cautioned glimpses of me had me thinking "is she wondering if I'd be a good fuck"

"Do you and Mary have lots of sex" she suddenly asked. She had no smile on her face. I told her to stop talking like that. To stop thinking in those terms; that it was stuff people didn't talk about. That was a private, personal matter. "Oh, sorry Chet, I didn't realize that. Mary would tell me. I know she would. Mary's like that you know. You know I've babysat for her before; couple of times in fact. You do have sweet kids. Like you, you know."

Damn it, she was making me horny. I wanted to open up to her. I would have opened up to her. I would have told her anything she wanted to know, anything at all.

"Wanna go to the other room Maybe we can go out to the back porch. It's nice out there tonight. We won't bother the kids. We can talk you know, openly... about stuff." I shrugged my shoulders and told her okay. She pranced outside like a girl on uppers. I pictured her titties on full alert. Her nipples although tiny as hell, they probably were as hard as pebbles. "See it is nice out here, kind of romantic huh It's a place where I'd sit and talk things out. Nice place to sit and talk and ask questions about stuff, about life."

I faltered and asked her what stuff. She said "You know guy stuff, stuff guys do umm behind umm you know closed doors umm when girls aren't around." I didn't understand, my expression displayed that, and she explained. "Well girls, they do lots of things. Normal everyday things, but they do fun things too. You know personal things, private things, and I guess I wondered if guys do those types of things maybe"

God I could have pulled off her jeans, ripped off my dress slacks, pulled down her panties, and ripped off my underwear on the spot. She see my erection, smile, and assumedly go for it and give it a go with her tongue and mouth initially. Then she'd want it inside her like a good little girl... of 18 that is.

"Cassie" I began to say. "I'm not going to talk about what men or guys do behind" and I used my fingers for quotation marks 'closed doors.' Is that understood" I told her politely.

She acknowledged it. We looked out at the sky. She said "It's a sexy night isn't it The stars are out, it's warm out, and guys and girls are out doing those fun things. You know what I mean" I didn't acknowledge her remark. "It's okay if you don't say anything. I like to talk plus I like knowing stuff about guys and what they like."

I went on to tell her lots of things guys like while leaving out all the sexual areas. I told her guys are guys. They have their own way of thinking, their own way of doing things, and almost all the time it is different from a girl's way of thinking and doing stuff.

"So you mean to tell me guys won't jack off, masturbate They don't think about girls They don't imagine being with a girl ever I mean I think about guys. I think about all kinds of guys too. That doesn't mean I... well maybe you don't want to hear any of this. I guess you wouldn't, huh"

I didn't say no. I never said yes. I could have told her that I could easily reach down inside my pants and jack off and cum without taking off my pants. I wondered what she'd say about that. I wondered how she'd react to that.

"Do you ever do that" she said out of no where.

"Nope, no I don't Cassie. No need to. I'm married and pretty happy as it is."

"Well I won't mind if you say you did. It's kind of cool that guys do it, except those ugly old fat guys, but I guess everyone gets horny, don't they" she said.

"I guess" I told her by mistake.

"You get horny" she asked "ever"

"I guess, sometimes" I came back, again mistakenly.

And in the most playful voice that night she said "Cool! Now that's cool!"

I told her to drop it, to stop asking all those types of questions. I told her in a round about way they were inappropriate and uncalled for. As her employer I had told her we shouldn't be having a discussion of that nature. She said she was sorry and wouldn't ask me or tell me anything like that again.

Mary came home, she was worn out. She danced with Aaron and Kirk half the night. I took Cassie home and before we got there she said one last lasting remark.

"I'll think about you probably. You won't mind will you"

She touched my arm. A twinkle in her eyes led me to almost tell her she turned me on. She waved goodbye, thanked me for the ride home, but came around to the other side and leaned forward. Cassie kissed my cheek. I didn't see that coming and all I wanted to do was either go home sex up Mary or jack off somewhere private.

Mary had to go out of town and called Cassie to watch the kids. She knew I had my weekly golf outing somewhere. Cassie couldn't do it and when she called back, she let me know. She had to baby sit all night Friday and most of Saturday night. But she was available to come by if I wanted to go out. I had tentative plans and accepted her offer. The plans fell through and the kids were already in their rooms just but not asleep yet.

"Hi" she said seeing my face at the front door. Then she looked at me. I had baggy shorts on, a nice v-neck t-shirt on, and sandals. "You're not going out" she asked. Her smile was brilliant, her minute titties seemed overly aggressive, and I could practically feel the little thingy's being savored in my mouth. She wore another adorable blouse, but had on cute tight shorts which showcased her skinny short legs. "You look summery" she told me.

"And you do too" I came back.

"Thanks, so you want me to stay or should I go on home I don't have anything going on if you want me to hang out tonight. But I'd understand if you don't. I mean after I guess embarrassing you last week you don't want to talk or anything."

"Nah don't worry about that" I told her.

"Cool then I won't, but I have thought about you lots of times. It's been all good too. I'm happy I did ya know. Yep, I was really happy I did."

My penis started acting up again. God damn it. That girl and her frame of mind and how she phrases her words. I could kill her. I could grab her and shake her madly. I could grab hold of her feel her up, teasing and toying with her na´ve desires until she orgasms several times over.

"So have you thought about me at all You know... like how I mentioned the last time"

Alone, no wife, and kids banished to their rooms for the evening they had fallen asleep on their floor, but he could hear a movie upstairs. He told her to hold on and walked up. He pulled blankets over the two of them. After turning out the lights and shutting off the TV, he closed the door for the night's pleasures, hopefully. Aroused before hitting the stairs again, he wondered what was in store for him, and just as he hit the bottom step she began to stand up. Her blouse was undone, but she had left it hanging off her shoulders, and she was about to turn and let him see her in the flesh.

Suddenly the phone rang. He was totally unaware of what Cassie had done and turned to answer it before entertaining her. It was Mary. She called to talk. She was lonely and bored, and wanted him to use that swift tongue he was infamous for. He used it often on her when they courted. He used it the night of their wedding. He's used it often since then especially on anniversaries and Christmas. His way with words they had a powerful influence on her and with her being out of town, he began to understand everything.

Mary wanted his poetic words to assist her in a fantasy, which involved him and her in some sexual predicament. It would take about 5 to 10 minutes, but fortunately for him it only took about four minutes that night. As lonely and horny as she was, Mary was already prepped, and listening to his voice and his phrases would insight her climatic finality. She thanked him and said loving things and as she did he pictured her, but mainly his mind fell on someone different.

She sat waiting in the other room "searching" for many "answers", but Cassie really didn't need any of that all. She's had her fair share of guys and men. Her vagina's been searched and researched often, but never by a man as easy to be with as him. Chet's heart beat wildly, his penis full of tremors, but once he saw her like she was it would send him over the edge.

Cassie waited on the couch, anxious to see his reaction, and while waiting she ran her hands up and around her little mole hills. She wished they were larger, but sometimes they were a blessing as they never got in the way when she had to run. Toying with her nipples, she made them stiff and pleasurable, and as she did she kept licking her index fingers beforehand.

"That was Mary" he said.

She replied and stood up. He thought he saw something strange about Cassie. But with the lights down low he wasn't really sure and she turned around wearing a brilliant smile. He stopped dead in his tracks. She remained standing where she stood up and smiled. He couldn't believe his eyes. Chet wasn't about to tell her to button up. He wanted to see them close up and she'd oblige him. He hadn't come any closer so she walked around the couch, but stopped from coming any further at that point.

They were small like he imagined. They were small enough to swallow. His cock raged and he didn't care if she saw it that way. He felt its growth inside him and he also had that urge to adjust its position. At that point Chet no longer cared and did as he pleased. He reached down to move his raging erection until he was comfortable. She watched him delight as his hand cupped his crotch. Her smile was enormous at that point.

"Do you like them" she asked. "I do" she told him. He nodded. "Cool, cool beans" she told him. "Uhhhh wanna feel them... please" He nodded again, his eyes affixed to her little titties. If he paid any attention he could see her nervous twitch. She was nervous, but she wanted him t touch them badly. She hoped and prayed he'd love them as much as she thought.

He came up next to her, didn't even look her in the face, and he ogled the cute beauty surrounding them. His dick was long and hardened. He felt it itching to get out. He wanted to lay her down and mount her petite body.

"My mom died a few years back. My daddy likes them too, but I've always told him I've wanted my privacy. He wants to look at them. I think he wants to touch them, but I don't know to be honest. Some of his friends, they wanna touch them. One guy did, but he wasn't as old. He was about your age. He wasn't as good looking. But he was nice. He was really nice. We had fun. I think you're fun too. At least I think so. I think a lot of things about you. I think about you, being with you, and... and doing things with you. I think about you a lot you know. I have fun thinking about you." She winked.

He didn't see her wink. He didn't hear her say anything about her mom, about her dad, but he did hear what she said about guys and about him. He was ready to have sex with her regardless.

"Well do you Do you wanna feel me" she asked.

He nodded. He reached up, pushed back her blouse until it hung just off her shoulders. He noticed how young and fresh and soft they were. He felt like kissing them. They were so damn adorable. Not frail, but not full or chubby she was perfect for an 18 year olds figure, Cassie's hair was long, but it didn't seem to interfere with her frontal display at all. He found her to be almost every man's fantasy come true, except her boobs could have been larger. At that point she was willing, she was carefree, and she was his. She was all his for the taking and she was like a charity bank willing to donate for the cause.

Feeling her little breasts, he behaved delicately and used a dainty touch around them. She delighted in it all. She told him that no one ever treated her so nicely when they felt her up like that. Most wanted to be rough on her. They all thought it was the sexy, manly way of doing it.

"Nah these require a delicate touch, not some rough and ready grabbing."

She loved his response. "Wanna lie down" she asked. He nodded, but took her hand in his, and they walked down the hallway to a guest bedroom. In there, he left the door partially open, and she removed her blouse altogether. Her body, it was so small so skinny, but it had nice casual curves although not as mature looking as some 18 year olds. "I do make a good lover" she said. "I'm as good as any 30 or 40 year old woman. Honestly I am. I probably squeal better too. Do you like squealers"

He told her he did. He told her he loved "squealers." He told her "squealers" always were better in bed. They were into it, wanted multiple orgasms, wanted to get every last drop from a guys cock, and he also told her that "squealers" are more ambitious, more rambunctious then non-squealers.

She laughed and came back saying "Well that would be me." He laughed with her. "Oh and I also love it when a guy does my pussy too. God I love that. Oh that's fucking incredible. I mean I just wanna crush a guys head in between my skinny thighs. That's what's so freaking wild. Do you like eating out girls too" He told her he did. She was crazy about him and asked him to take off all his clothes. She took her shorts off, but left her panties on. Seeing her naked like she was had driven him to the brink of ejaculating. He wanted to tell her, but didn't; not at first he didn't.

"Oh yeah and another thing" she added "I don't love you. I'm not gonna fall in love with ya if you're thinking that. Let's be clear about that, alright" She winked again. "This is all just for fun. Straight, enjoyable flesh ripping sex okay and nothing else but that okay"

He told her as he tongued her titties that's how he felt. He told her that her boobs were absolutely perfect. She told him he only said that because he was a guy, she was a girl, and he was horny. He admitted she was right. She laughed, he laughed too, and he continued toying with them. She asked him if he wanted to try and swallow them. He told her he was planning on it. She said she really gets off on that. It was a huge turn on for her.

When she did try and out her little titty in his mouth he almost had the whole thing inside. Feeling her pert small boob was like nothing else he had ever imagined in his life. Feeling it, wallowing in the tiny physical features of it, and feeling the soft smooth textures as it shifted around a little while inside his mouth was driving him and Cassie wild. She moaned as she moved here and there while feeling the moist inner linings of his mouth holding her fine titty inside it. It was more then just pleasurable for her. It was earth shattering to her while her boob say in his mouth. He was wallowing delightfully providing her with an array of orgasmic like activity within her tight little pussy. Her spasm of movements in many various ways created contortions he was unable to fathom.

His cock was involved in its own mad contractions as it wanted to expend its load inside her. But did he dare let that happen He wasn't sure and pulled away from her tit letting it collapse against her chest. She giggled and let him know she loved how he did that. It wasn't violent in nature. It wasn't aggressive in any way. He was a natural lover and she told him to do her other one like that. He was on it in a second and she proceeded to move about in her spasmatic contortions. Her pussy couldn't handle it and she called out to him to fuck her.

"God Chet will you fuck me, please will you" she begged. "Oh god come on will you"

He didn't answer, but pulled away from her little tit. He told her what an incredible experience that was. She said she hoped it was fun for him. She said she totally loved feeling it inside his mouth, but that she'd love to at least feel his cock inside her and she'd suck it off to get it hard if he needed it to be done.

"I mean I love sucking cock. Cock is awesome. Every guy has a great cock and I know yours is probably even more awesome. Will you please, please Chet" she pleaded.

He was hesitant to do it, but he wanted to do it too. He wanted to see how cool her cunt was. He wanted to know just how tight and shallow it was and how much she could put up with. So he conceded and told her he would, but he wouldn't cum inside her.

"Then at least make me cum that way, please" she asked.

He said okay and slipped it inside her. She squealed and squeaked instantly, making every odd sexual sound in the world he could have ever imagined. But the longer he was inside her, the worse it became. The longer he remained inside her unusually tight cunt, the more he wanted to bang it, and in any possible position one might imagine, and then some. She was a contortionist. She could bend and flex her body in ways he wasn't even able to imagine Mary do anymore.

But she was a squealer and he was a good sex partner. He brought her to have the orgasms she wanted, somehow, and when she was finished, he pulled out, and he told her to suck off his cock. As out of breath and as worn out as she was she still found all the vital energy to enthusiastically suck him almost dry until he did the remainder by himself.

His unloaded on her cute little knobs while focusing directly at her tiny hardened nipples. But she asked for it in her face and stuck out her tongue. She wanted to swallow it for him and make sure she pleased him and he told her she did. She collapsed and he collapsed against her as he held her by her adorable little boobs letting her collect herself.

"We should try and do this more often don't you think so" she asked.

He didn't answer her question. But he did say "Your boobs... they are amazing. They are delicious as hell too Yeah okay since you're sure you don't love me... I suppose we might do this again. I mean I've never seen anyone do what you just did. I mean the way you fucked me God that was brilliant and sexy as hell."

When Mary came home two days later she asked about some woman he talked to. She mentioned how "this woman" and he were sexually involved. He was paranoid. He wondered how she could have found out about him and Cassie. He blushed. He was worried.

"I heard some woman called you, asked you about sex or something, and you did something that got her off What was all that about Who was she I heard her name was... it was umm" and he was scared straight "Mary Is that true"

He was relieved and he smiled, took her to that guest bedroom, and they made love the old fashioned way. Marriage remained intact for a while at least.

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