Barely legal teen Ashleys babysitting goes wrong 18 year old
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Katie And Ashley’s Friendly Bet free porn video
“How do I get myself in these situations?” It’s a question I ask myself a lot. The answer is not complicated and I’m a smart girl. My day job as a transaction coordinator for a mortgage company demands it. It also requires people who are highly responsible and have excellent people skills. Everything that happens in a loan process comes in or goes out through me. There’s a lot at stake. That’s part of what I like about my job. I love being in the middle of transactions or situations where everything’s on the line. It taps into my playful adventurous side, like the thrill of flying through a Peruvian jungle on a zipline. (That’s a different story.) The bigger the adventure, the more fun it is for me. The more that’s on the line, the more I am drawn in.
So, how does a smart responsible person like me get myself into precarious situations? The simple answer is that I like to have fun. Unlike some of my friends, I don’t live to work; I work to live. When the clock hits five, I take my fun-loving, social, adventurous self into my real life, leaving behind the more responsible side of me for when I return. Don’t get me wrong. I don’t leave my brain at work, just the intrusion of always being sensible. I love to have fun; I love people; and most of all, I love to have fun with people. My friends, like Ashley, will tell you I love to live fully in the moment without thinking much beyond it.
My name is Katie. Ashley is a friend I made through other mutual friends. We often find ourselves at the same parties, hangouts, and bars. She likes to have fun too but is much more competitive than I am. Her competitiveness has led to her continuing professional success, climbing the ladder in the back offices of the bank where she works. She loves sports, from golf to softball. She loves to win and hates to lose. When we play games at a party or bar, I play to have fun; she plays to conquer.
It all started with Ashley’s three words: “I dare you.” We were dancing together at our mutual friend Jake’s wedding. The reception continued late into the night, and with it the number of drinks we each imbibed. We were both blissfully drunk and enjoying the party. We had the whole weekend ahead with nothing to lose. Or so I thought. I was wearing a red dress with small white tropical flowers. The thin shoulder straps led to a ruffled bodice that showed just enough cleavage on my slender 5’10” body, over 6’0” in my sexy heels. The dress fell to just above my knees, highlighting my fit body, tan skin, and legs. My curly blonde hair cascaded over my shoulders, framing my sparkling blue eyes and smile that I’m told lights up a room. Ashley wore a black sexy dress with two spaghetti straps over each shoulder that crisscrossed her tan back, and offered a generous view of her tits. Ashley’s straight blonde hair also fell past her shoulders. Her dress showed off her fit athletic 5’5” frame. I’ve always loved her contagious smile and laugh.
“No!” I answered unconvincingly. “You do it. I dare you.”
“Yeah, you’re right,” she answered. “There’s no way he’d go for you anyway. You couldn’t get him to kiss you if you tried.”
“What are you talking about? I could get him to fuck me if I wanted. I’m just…”
“Okay. You’re on,” Ashley interrupted.
“Wait. What?”
“It’s simple. I say you can’t get him to kiss you. You said he’ll not only kiss you, but you can fuck him. I say, prove it.”
We both glanced over at him, only to see him look up in our direction again while sipping his drink at the bar. He was tall and handsome in a gentle rugged way. His dark eyes were mysterious. He had mussed brown hair and a gentle smile that gave him a strong confident look, but not in a cocky way. He looked like he might be about our age, in his early thirties. He was wearing a dark shirt, with the top two buttons open. He smiled as our eyes met his.
“Bullshit,” I said. “I see what you’re doing.”
“I’m not doing anything,” Ashley playfully teased. “I’m just saying... I mean, how can someone that handsome be alone at a wedding? I guarantee you there’s no way you can get him to kiss you. You’re the one who upped it by saying you can get him into bed. Prove it.”
One of the waiters working the reception interrupted our conversation. He had been giving Ashley and I a lot of attention and drinks all night. His hopes were clear, and would definitely be dashed despite his efforts. He handed us two more drinks with a wink, before walking away.
I picked up the liquid courage, after Ashley’s challenge.
“A hundred bucks,” Ashley said with a devious chuckle.
“What?” I asked.
“A hundred bucks. I am so certain you can’t get him to fuck you tonight that I’ll give you a hundred bucks if you do.”
I emptied the drink with resolve. Somewhere deep in the far reaches of my mind, I knew better than to accept her challenge. But, my mind was buzzed and my body was ready to play. I was in the moment. I couldn’t resist her challenge. My inhibitions were almost completely gone.
“Three hundred,” I blurted in negotiation.
Ashley smirked, knowing that for me to offer another amount, meant I was accepting her crazy challenge. “Three hundred?”
“Three hundred, and I’ll do it.”
Ashley smiled with a look of conquest. “That’s crazy. Two hundred, but I’ll need proof. That’s my final offer. But I understand if you chicken out…”
“Deal,” I said with a smile, feeling sly that I got her to double the amount. I took her drink from her hand, threw my head back and emptied it. I gave her the empty glass back. I pressed my hands down the front of my dress and ran my fingers through my hair. “How do I look?”
“Amazingly fuckable,” she said. “Too bad he won’t take you up on it.”
“Just you watch. Have my money ready.”
“I will, as long as I see photo proof of your naked fucked ass with him.”
I walked over to the bar and sat down next to him.
“Not with your friend anymore?” he asked.
“Maybe I’d rather make a new friend,” I answered. “My name is Katie.”
“Hi, Katie. Cliff. You look familiar. Have we met?”
“Um, I don’t think so. I’d remember a face like yours”
Cliff blushed genuinely. “Now you’re officially flirting.”
“Guilty. So, how do you know Jake?”
“I used to work with him.”
“You alone?”
“I am. At least I was,” he added with a warm smile. “Can I buy you a drink?” he said with a chuckle, offering something from the open bar.
“Since you’re such a big spender, how can I resist?”
“Get anything you want then. It’s on me.”
“Maybe what I want on you isn’t behind the bar.”
“What?” he asked, pretending he didn’t hear me.
“How about a Long Island.”
“Long Island it is. You sure we’ve never met?”
I looked at him closer. “Maybe. You might look familiar, but that’s probably just because I wish we had. I’ll never forget now.”
Cliff blushed again. We engaged in easy small talk as I finished my Long Island. “Want to dance?” he asked.
“I’d love to!” As we walked to the dance floor, I winked at Ashley. I knew I had him. I gave Ashley a look, gloating in what I knew was my certain win. She smiled back playfully, I think a little jealous.
Cliff paused as we reached the dance floor. The song was slow, like so many at the end of wedding receptions. Good D.J.s know there is no better time or place to hook up than at the end of a wedding reception, and do all they can to help out the cause. As Cliff and I moved as one to the music, I pressed my body into his, making clear my desire. I felt one of his large muscular hands at the center of my lower back, the other engulfed my petite hand. He led our bodies around the center of the dance floor. Our bodies gyrated romantically together. A string of lights shone down on us like bright stars from the dark sky above. I let go of his hand and moved both hands up to reach around his broad neck, freeing his hands to enjoy wherever he wanted. My sparkling blue eyes looked up into his; I felt as if his dark mysterious eyes were reading my soul. His newly freed hand moved to my side, dangerously close to my tits. I offered an inviting smile of approval. His strong hand on my lower back descended closer to my wanting ass. My body tingled in suspense. He had no way of knowing yet that my pussy was soaked. I couldn’t remember feeling a more suspenseful arousal, especially in the arms of a stranger.
I smiled, cocked my head, and offered my lips to him. He lowered his head and brought his lips to mine. It was magical. The room spun, more from the kiss than the drinks. I let out a soft moan as I pressed my body completely into his, discovering his own hidden arousal pressing against my abdomen.
“Want to get out of here?” I asked.
Cliff smiled. “Yes, but you’re a little drunk. I don’t want to…”
“I do, Cliff,” I interrupted. “I want to.”
“You sure?”
“I may have had a few drinks, but I know what I want.”
“Your place or mine?” he asked.
“Yours,” I answered without hesitation. He seemed nice, but didn’t want him to know yet where I lived. That might change in the morning. “I shouldn’t drive anyway.”
“As you wish,” he said.
After a short drive, we arrived at his house in the city. He opened the door and motioned me to go in. He followed me in before closing and locking the door behind us. He turned on a light as we entered, immediately dimming it to a low romantic level. We looked at each other with some awkwardness, almost complete strangers with only a mutual friend between us.
“Can I get you a drink?”
“Yes. Do you have a Cab?”
“Coming right up,” he said. He poured himself a rum and Coke and started a romantic playlist.
“Cheers,” he said, as our glasses kissed.
“Mind if I take my shoes off?”
“Not at all,” he said. He watched as I leaned over to remove them, offering a full view of my tits. I looked up approvingly as his eyes were undressing the rest of my body. As I stood in front of him with bare feet buried in his carpet, I realized my nipples betrayed any chance of hiding my arousal.
Cliff stepped toward me, offering a small kiss as our bodies began to move together to the music. The chemistry between us was undeniable. I cozied into his body, allowing my hand to move down toward his ass. He leaned down and offered another gentle kiss. His hand moved up and cupped my tit. I moaned softly with desire. We continued to dance as our hands moved freely to explore each other’s bodies.
I finally couldn’t take it anymore. I started to unbutton his shirt before pushing it off his broad shoulders, exposing his bare chest. I began to kiss it as my fingernails gently raked his naked skin. I felt the hem of my dress begin to make its way up my legs, exposing my ass, my abs, my tits before being pulled over my head. He tossed it onto the couch. There was nothing left but my thong.
Our kissing became more passionate. I reached down and unbuttoned and unzipped his pants. I pushed his pants and boxers down as I knelt before him. His long eight and a half inches bounced up to me. His cock was thick and his head red and bulbous. I took the impressive knob between my hungry lips, massaging it first before enveloping the entire length into my mouth.
“Augh!” he cried out as his head dropped back. His pelvis slowly moved back and forth, fucking my ravenous mouth. He grabbed my hair in his hands. My hands reached around and took hold of his perfect ass cheeks, digging my fingernails in, holding him tightly as his hips rocked. His cock and entire body were captive to my master oral skills.
“Oh fuck!” he yelled, only encouraging me all the more to consume him. I spit on his shaft before devouring it again. “Shit, you’re good,” he said, wrapping his fingers into my hair and pulling me forcefully to him. His words only intensified my desire to ravage him. “You are such a dirty slut. Damn, what a filthy cocksucker.” The more he talked dirty to me, the more insatiable I became. I was desperate to have his warm thick cum pour down my throat.
He suddenly pulled out of my mouth, leaned down, and picked me up like a rag doll. He carried me to his bedroom and laid me on his sprawling king-size bed. He pulled my thong off and immediately began reciprocating the love, devouring my pussy. My naked body squirmed blissfully from the touch of his tongue and lips on my soft folds and clit.
“I’ve got to have you in me,” I said, lost in the sheer unbridled lust of the moment. He moved up my body like a large muscular animal ready to devour his prey. I wanted nothing more than to be ravaged by him. He paused as he looked into my sparkling blue eyes. Before he could say a word, I said, “Fuck me, Cliff.”
I felt the head of his large cock obediently press against my soaked pussy. My back arched as his thick shaft began to penetrate me. God my pussy was hungry for him. “Oh, fuck yes,” I said, anchoring my long nails into his back. I pushed my hips up, desperate to feel his entire length in me. He slowly began to fuck me. His cock massaged everything in me while my clit surrendered to his movement over me. In a way beyond anything I had experienced, he quickly brought me toward my first orgasm of the night. My entire body purred with pleasure. My nipples tightened like thimbles reaching toward him. My red painted lips gaped as the climax crashed over me like a powerful wave. Goosebumps covered my skin. My body quaked below him. “Oh yes! Yes! Yes! Oh, fuck yes!”
We continued to fuck each other all night with insatiable primal lust. Sometimes it was soft and tender, others rough and passionate. Playful giggles alternated with possessed desire and filthy talk. The smuttier he talked, the more my carnal appetite intensified.
The morning sun rose and streamed through the bedroom window. We laid exhausted, wrapped only in his thick cum-soaked sheets.
“God, that was great,” I complimented.
“You are amazing,” Cliff answered as he tenderly traced my petite jawline with his finger.
“Thank you. You’re not so bad yourself.” There was a brief pause. “Oh, would you mind if I get a picture?”
“Picture? Of us? Like this?”
“Um, yes. To remember the moment,” I offered as a half-truth.
“I don’t know how you could ever forget,” he answered with a smile. “I won’t. You want a picture, like a trophy?”
I smiled back. “Truthfully, I promised Ashley.”
“What? The girl you were with at the wedding? You promised a picture of us?”
“Yeah.” I was hesitant to say anything more after what we just experienced. “We made a bet,” I blurted, regretting it the moment the words left my lips.
“A bet?”
“She bet me I couldn’t get you to kiss me. I told her I could not only get you to kiss me, but I could get you to fuck me.”
“So, I see. You were just using me to win a bet. That’s all this was? I thought we had a connection.”
“No, no, I mean, yes, yes, there is definitely a connection Cliff. It was amazing. Maybe the best sex I’ve ever had. It started as a bet but turned into something better than I imagined.”
“Fuck. How much?”
“How much what?”
“How much was the bet for?”
“I wanted three hundred dollars, but did it for two hundred.”
“So, you lowered your price to fuck me.”
“No, I mean, I didn’t think of it that way.”
“What does that make you if you’re getting paid to have sex with me?”
“It’s not like that,” I pleaded. “I’m sorry, Cliff. It was amazing. It still is. Don’t be mad. It became way more than that. Think of the pic as capturing the magic of our first time together.”
Something in Cliff’s soft mysterious eyes darkened.
“Please, can we just get one pic? If I don’t, Ashley will never let me live it down.”
Cliff conceded.
I looked around for my phone, realizing it was in my purse in the other room.
“Here, use my phone,” offered generously. He reached over and picked it up from his nightstand and handed it to me. “I’ll text it to you, that way I have your number, and you have mine if you’re serious about hooking up more.”
“I am,” I reassured. “I definitely am.”
I took a couple pictures of us posing naked in the bed. Cliff seemed sweet, going along with my awkward request. He even got playful, taking some sexy pictures of me. I asked if he would include a video where I could rub it in her face by announcing my slutty all-night fuck as undeniable proof of my win. He texted me the pics and video. I quickly sent them on to Ashley with a snarky text demanding my money.
“Thank you,” I said. “How can I ever repay you?” I asked with a playful sexy smile as my hand glided over his dick, bringing it back to life. “Oh, I think I know.” I gave him the best morning fuck of his life.
We both fell asleep. I woke just before noon to the sound of him in the shower. I joined him there to continue my honest enjoyment of his body. The hot water poured over us as we lavished ourselves with unrushed soapy shower sex. I loved the feel of his cock and muscular body against me, lubricated by the warm suds. I surrendered to him having his way with me in the thick fog of hot shower steam. After we dried each other off, he offered to make me breakfast. I put on one of his t-shirts that draped over me, barely covering my ass. He put on a pair of athletic shorts. We sat at the table and ate, enjoying what I thought would be the final relaxed moments of our weekend tryst.
“I figured out where I’ve seen you before,” he said.
“You have? Where?”
“At the mortgage company,” he answered.
My eyes got big, my body froze in shock. I never said anything about where I work. It would be impossible for him to know, unless it was true. “What?”
“Yeah, that’s where I have my mortgage. I actually am longtime friends with Bob.” I knew he must have meant Bob, the CEO of the company. “I also know most of the board,” he added.
“No way,” I said. “How do I not remember you?”
“I’ve had my mortgage there a long time, before you started.”
“Shit,” I said, under my breath, but unintentionally loud enough for Cliff to hear. “What a small world.”
“Yeah, I know Bob more than frowns on employees fraternizing with customers.”
I looked up at him, surprised by his comment. I also knew it was true. “Yeah,” was all I could offer.
“The board is hyper-cautious. Can’t blame them after the recession, bailouts and so many mortgage companies going under ten years ago from ethical violations.”
“Yeah. We can keep this as our little secret,” I whispered flirtatiously with some nervousness. “No one needs to know.”
“I don’t know,” Cliff pondered out loud, with a glance up into my eyes.
“What do you mean?”
“I know Bob and the board have fired people for less,” he said matter-of-factly.
“He has. Cliff, you can’t say anything.”
“I suppose that’ll be up to you.”
“What do you mean?”
“Your full cooperation.”
“Wait, are you…?”
“This was all your idea, Katie. And it’s been fun.”
“Yes, but.”
“But I’ve just been your pawn to use me to win a bet. Just another sexual conquest for your amusement and gain.”
“No. I mean yes, but no. It’s so much more than that now, Cliff. What can I do to prove that to you? Tell me. Anything.”
“Whose idea was it, that you could get me into bed before we had even met?”
“Mine,” I answered softly.
“Whose idea was it to seduce me at the bar like a little game, without even knowing me?”
I dropped my head in silence, struggling to find words.
“Whose idea was it to come to my place, even when I offered a way out so you would not feel taken advantage of when you were drunk? To think I was worried that you might think I was taking advantage of you!”
“Yeah, but…”
“Whose idea was it to start taking my clothes off last night? Who asked first thing this morning to take pictures and even a video to document, share, and cash in on your bet?”
“It was all mine,” I answered. “But it was all in fun. I didn’t know you were a customer,” I argued. “How could I?”
“You think anyone will believe that, with as good as you are at your job? If there’s any question, I’m the first person they’ll ask.”
“Wait, no one needs to know, Cliff” I repeated. “We can just enjoy what we have without anyone knowing. This was amazing. It still is.”
“Do you know what it feels like to have an amazing night like that, only to find out you’ve been used?”
“No, I don’t. I didn’t. I’m sorry, Cliff. It’s not like that for me.”
“But it is. If you hadn’t made that bet last night, would you have come home with me last night?”
“Um, maybe?” I answered unconvincingly.
“I think it’s only right that you know what it’s like.”
“To what?”
“To be used as a plaything for someone’s amusement and personal gain, like you did me.”
“What are you saying?”
“If you really want to prove it to me, then willingly offer yourself for my amusement and pleasure.”
“Like submission?” I asked surprised.
“Complete. Whatever I ask,” Cliff answered. “No limits.”
“What?”
“It was your question. You asked what you can do to prove yourself to me, offering anything. I’m just taking you up on your offer.”
“Yes, but, I didn’t really mean anything. I just meant…”
Cliff put his hand up to interrupt. “Anything.”
“I know I said that, but,” I continued to stammer.
“Now, at your work, what’s offered to secure a debt?”
“Collateral.”
“I think these pictures and video will serve nicely as that, don’t you?”
“Oh no, Cliff. You can’t!”
“You sound motivated. That’s good.”
“No one can see these, Cliff. I’d lose my job.”
“So you can share them with Ashley, using me to win your bet, but I can’t share them with who I want for my benefit?”
“Please, Cliff. I would lose my job, my income, my reputation. Mortgage companies all know each other.”
“They do. There’s a lot at stake.”
“Oh god, Cliff. Okay.”
Cliff smiled. “Okay, what?”
“I’ll do anything you ask.”
“Anything? That’s very generous of you, Katie. Do you mean it? Without limits?”
“Yes,” I answered. Cold chills covered my body. How do I get myself into these situations?
Aspen
- 29.12.2022
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- Straight Sex
