I opened the door to find Chloe in that damn yellow sundress with a cross-body purse giving her tits that seatbelt effect. They were so goddamn perky. This was happening. All of the nervous energy in the world was pent up inside of me and I was certain that I would find a way to fuck this up. As I was ushering her through the door my brain and my dick had a quick conversation.
“Dude, this is a done deal. Don’t fuck it up. Let me handle things.”
“It’s been a really long time. I’m not sure what I’m doing. I have no clue what she expects.”
“She expects to get fucked.”
“What if she gets scared off by me having kids or by me being a widower?”
“YOU DON’T HAVE TO TELL HER THAT! JUST FUCK HER!”
My dick was a very convincing debater.
We made small talk and I showed her over to the sofa. My memories of Jenna’s sexy freckled face staring up at me begging me to cum on her flashed for a moment. That really was up to that point the hottest thing I had ever experienced. Chloe sat down slowly with her legs pinned together. I watched as her dress rode up her thighs and exposed her Indian princess tattoo fully. It actually was kind of interesting. The TV was still playing SportsCenter. I remember having some jitters starting the conversation but don’t remember much of anything we talked about before the point about ten minutes after she got there when she took her purse off her shoulders and sat it on the coffee table.
“Do you smoke weed?” She asked.
“Not since the 90s.” I responded nervously. “You’re welcome to smoke here though, if you want.”
“Are you sure?” she replied.
“Yeah, its fine.” I said.
She took out a small glass bowl. I watched as she fished through her purse for a lighter and emptied a small little plastic bag of marijuana into her pipe. She brushed the loose strands of her golden hair behind her ear then she pressed it to her lips and light up. After a few seconds of silence she exhaled a massive cloud of smoke into my living room. I thought of how I’d freaked out at my son the first time I caught him smoking weed. She looked at me and smiled as she finished exhaling. This wasn’t the nervous smile she’d been giving me since she got here.
“It helps me relax. I have anxiety problems.” Chloe told me. I wasn’t sure how to respond. When I was her age we didn’t need excuses to get high.
“Well, good. I hope you feel relaxed.”
“Truth or dare?” she said hastily.
I stammered. “Uhmmm Truth?” This was getting kind of weird. Haven’t played Truth or Dare since I was in high school. She dramatically moved herself across the couch towards me but didn’t come all the way.
“How often do you hook up with women you just met?” She stared me in the eye waiting for my response like she was trying to read me like a sexy lie detector.
“I uh..” I paused. “I haven’t done this in a long time.”
She took another hit from her pipe. We sat in silence a bit longer. I couldn’t read whether she believed me or not.
“It’s your turn.”
“Huh?”
“It’s your turn to ask truth or dare…”
“Truth or dare?” I said.
“Truth.”
“What made you want to flirt with me?”
She grinned. “You’re hot. Truth or dare?” She shot back.
“Truth.”
“You’re no fun.” she teased. “What’s your favorite thing about me?”
I hesitated. Was I supposed to say something sexual? Was I supposed to compliment her personality?
“You’re really gorgeous. You have a nice smile and I like your tattoos.”
She scooted toward me on the couch. There wasn’t much space left between us at this point.
“Truth or dare?” I asked as I eased up to play her game.
“Dare.”
I ran over my options in my mind debating if I should go for it or keep taking it slowly. I couldn’t come up with anything.
“I dare you to let me hit your bowl.”
She looked at the bowl and back to me. She lit it up and inhaled the smoke. I expected her to hand it to me. Instead she closed the gap between us with the smoke still in her lungs. She leaned in to kiss me. Our lips touched and she grabbed my arm. Our mouths opened and she released some of the smoke into me. I inhaled. Our kiss broke. We both released the smoke from our lungs. I coughed. She giggled.
“Truth or dare?” she asked me grinning from ear to ear.
“Truth.”
“You have to pick dare sometime!” she laughed. Her high was clearly starting to set in. “Do you want to fuck me?”
“Yes.”
“Good.” she whispered. “Truth or dare?” she asked not giving me a chance to take my turn.
“Isn’t it my turn?”
“I’m taking an extra.” she said with her confidence building. She was becoming sexier by the second.
“Fine. Dare.” I spat back playfully.
“I… dare you… to show me your bedroom.”
*****
We made our way up the stairs leaving the glass bowl on the table and her gripping my forearm as I led her. Holy Shit. This was happening. I was going to fuck this woman who was basically half my age.
She pushed me down on the queen bed as soon as we crossed the threshold. She climbed me and mounted me. We began to make out furiously. Our tongues swept back at each other and swirled between my mouth and hers. I tasted the pot on her breath. Her hair smelled like a limes and some sort of herb. She skin was pasty and smooth. I ran my hands up and down the outsides of her thighs as she started to gyrate while we kissed. She tugged at my shirt collar. I raised my hands above my head and she struggled to pull it off of me because I was laying on my back. When she finally got it off of me she dove into my chest kissing my collarbones and my shoulders. She ran her fingers through the hair on my chest while her other hand dropped down my abs to the crotch of my pants. She gripped my stiff cock through the denim and whispered in my ear in a breathy, sultry tone.
“Do you need me to blow you? I’m so wet right now. I think it’ll just slip in.”
“You can suck it if you want to.” I replied. I didn’t want to pressure her for it but I thought a blowjob would help me build up and not blow my load straight away when I got inside of her. My hands kept roaming her thighs and started to adventure passed the barrier of her dress. I slid them underneath the yellow dress deliberately and up to her firm little ass. She wasn’t wearing any panties.
“Spank me.” she chirped as I nibbled her neck. I raised my hand slightly and brought it down with a small amount of force to her cheek. She jumped and made a yelp. “Fuck that’s hot Jake.”
Her hands fumbled to undo the button of my jeans. She reached into my boxers and grabbed my dick and stroked it with a firm grip. She pulled herself away from me to look at my face as she stroked me. My eyes met hers as she raised her body up. I saw her eyes widen as my cock grew more into her hand. She bit her lip.
I flipped her over from on top of me and pinned her down on her back with my arm across her torso and grasping at her tits. I reached into her dress and under her bra to grip her nipple. Her tits were so perky and way to big for her tiny frame. My other hand found her pussy under her dress. She was completely shaved. I ran a finger over her clit. She rolled her eyes and tossed her head back. I started to rub away at her clit trying to get her off quickly. I wanted her to cum. I wanted to show her that she had made a good choice.
“Take your pants off.” She said wincing from my fingers prying at her clit and her nipple. I reluctantly took my hands off her and lifted my body off hers. As I slid my jeans and boxers off and my cock sprang free she quickly shed her dress over her head and threw her bra off onto the floor. I ran my eyes up and down her body.
“HOLY FUCK!!” I said out loud. Her body was so fucking tight. Her tits really were to big for her body. Probably a C cup on a hundred and twenty pound girl who was only about five foot three. Her hips had an hourglass shape and she kept her legs together hiding her pussy from my eyes. Her pelvic area was clean and fully bald. I saw the last tattoo she had been hiding; a yellow daisy just under her hip where her pelvis dipped down to her pubic region. That was sexy.
She giggled at my surprised exclamation.
“You like my body?”
I just nodded with my jaw half hanging open. I’m sure she could see the desire in my eyes.
“Do you have any condoms?” she asked as she ran her finger up her flat stomach and over the raised mountains of her breasts.
“Fuck. I don’t think I do.” I replied panicked that this would ruin our fun. I looked in the drawer of my nightstand. Nope. Not a single fucking rubber. Her hand ran up my stomach and over my chest to pull me back towards her. She looked up at me.
“Can you pull out?”
I nodded. It was probably a lie. My dick had been in control most of this night. It didn’t care if if could pull out or not. It just needed to get in her.
She guided me on top of her and raised one leg up over my shoulder. Her hand guided my cock to her pussy. She rubbed my head through her lips to get it slick. She was indeed wet enough for me to slide right in. I pushed in gently the first time. Oh fuck. I had forgotten how great this feels. I pushed against her slowly until my cock was fully buried in her. Her cunt was just as tight as the rest of her body would suggest. She wiggled under me and squirmed to get herself into a comfortable position. She raised her other leg up over my shoulder. I started to increase my pace, pumping my cock in and out of her deeply. My rhythm got faster and faster.
I heard her moaning and grunting. I picked up the pace even more. She started to scream.
“FUCK FUCK FUCK OH YEAH!” she cried loudly. I worried the neighbors would hear her screams.
After fucking her as hard as I could I felt her legs losing the strength to stay up over my shoulders. I laid off of her but didn’t take my dick out. It felt so incredible I wasn’t sure I’d ever be able to take it out. She lowered her legs to my side.
“Do you want to fuck me from behind?”
I couldn’t speak. Of course I wanted to fuck her from behind. I just nodded dumbly. She smiled and rolled over onto her stomach. She grabbed a pillow and placed it under her hips. She looked back over my shoulders.
“My legs are too sore for doggy. Just climb over me like this.”
I straddled her thighs and rubbed my cock against her ass. She wiggled at it and kept looking back at me over her shoulder. I started to try to ease my cock into her pussy but it went too high and pressed against her asshole. She didn’t jump or try to squirm away she just groaned and said,
“Not on the first date.”
She gripped my cock and guided it to the entrance of her pussy and raised her hips to let me slip in. She was so fucking tight like this. I worked myself into her. She was wet as fuck and it wasn’t too hard to get a rhythm going again. I started to feel my balls swelling. I was going to cum. I had totally forgotten about our agreement to pull out. I just kept slamming myself into her cunt as hard as I could and gripping her little ass tight around me. She groaned and tossed her head back and forth slinging her short ponytail loose.
“Put your hand on the back of my neck.” she demanded. I complied and used that arm as leverage to fuck her even harder. She cooed and gasped. Then she grunted and reached her hand back to spread her ass open to make sure I got in her as good as possible. She was loving it.
“You like that daddy?” she asked.
“Fuck yeah.”
“You want to fuck your little girl all night?”
“God yes. I want to fuck you every way you can dream of..”
Though the whole daddy thing was a bit off putting to me at first I wasn’t lying. I wanted to fuck Chloe in literally every way imaginable. I wanted her to ride me. I wanted to bend her over and take her without her expecting it. My mind ran through these scenarios. I wanted to fuck her in the Target bathroom next time I went out for groceries. I pumped my cock away into her while I dreamed of the dirty things I could do to her. I wanted to fuck her asshole.
“Am I a good little slut for you daddy?” she whined.
“UGH Yes Slut. Good Slut.” was all I could manage. I was pure primal need. I needed to cum. I needed to fuck this little girl. I needed her to be my slut. My mind was racing. My dick was slamming into her with all the might my 6’2”, 210lb body could muster. She was my fuck toy in that moment. I was just using her body to make me feel good. And she had wanted it. She gave me her number and she invited herself over and she kissed me and she wanted this. This was happening.
“Are you going to cum for me?” she asked.
“Uhuh baby. I’m gonna cum for you.”
“Do it daddy! Pull out and cum all over me! Cum on my ass!”
I took a few more power thrusts into her. I pictured her on her knees under my desk while I worked sucking my dick. I pictured her fucking me in the back of my car in the Target parking lot. I pictured her face covered in my cum. Then my mind did something awful. It turned Chloe’s gorgeous fair face with its nose piercing and those glasses into Jenna. Jenna’s freckles. Her dark curly hair and her eyes looking up at me. Jenna’s full pouty lips wrapped around my cock. Her lips mouthing the words “Jake I need your cum.”
I came. I released every ounce of my pent up seed into her. I emptied my balls against the walls of her pussy and I felt her pussy clenching me. She stared back at me shocked and utterly wrecked. She was enjoying the feeling of my cum in her and my cock twitching in her pussy as it sprayed her and bred her. Her eyes rolled into the back of her head.
Source: reddit.com/r/eroticliterature/comments/cap9qo/chloe_ptii_my_night_of_truth_or_dare_with_the
This is fucking epic!!!
My heart was racing so fast near the end.
A few more thoughts:
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-I was disappointed at first by the transition to Chloe, but I grew to like it. Even though she is not my type at all, I like that it adds to the agony of the drawn-out build-up between Jake and Jenna. Also, I like that she is not Jake’s type at first, either–makes it more realistic.
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-Speaking of realistic, the sad scene at the beginning of Chloe Part I between Jake and Jenna is something you don’t often see in these types of stories. No passionate breakup sex, just a mutual acknowledgement that a good thing has come to an end. A great moment that will make it all the more electric when it finally happens.
​
-Likewise, the “daddy” thing does nothing at all for me and I enjoyed that it did not do much for Jake, either. It is realistic that sex partners are not always 100% compatible. It would’ve been so easy to write Chloe as a YouPorn sexpot that pushed every single one of Jake’s buttons and could do no wrong. Was great to see something different on that score.
​
-I was on pins and needles wondering if Jake was going to pull out. Wow.
​
-I am still on pins and needles to find out what happens between Jake and Jenna.
I’ve really enjoyed all your stories, and this is no different. Excellent pivot from Jenna to Chloe.
Great