Second Date Rimjob
Chapter 1

Caution: This True Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, True Story, Analingus, Oral Sex,

Desc: True Sex Story: Chapter 1 - While getting to know her, I get to eat her ass...

I arrived a little early to my second date with Chloe. I was nervous. She was definitely a cool girl, but she had a mischievous aura about her - I never knew what she would do next. I guess that would be expected because for all intents and purposes she really was still a stranger, but I felt a crazy kind of energy being around her. Tonight I was picking her up at her apartment, a nice place downtown.

I had met her a few nights ago. We hit it off extremely well, to my surprise. Chloe had a quick, wicked tongue, coming across as classy and polite, but with the ability to turn to bawdy, low-humor with ease. She was exciting, and I was looking forward to another fun night. She didn’t let me come into her apartment that first night, being surprisingly chaste and proper that evening despite some suggestive comments over drinks. That said, I was hoping for a repeat performance, a good evening, and maybe staying the night if she was willing, but I was cool if she wasn’t - no need to rush. In short, I didn’t know what to expect tonight.

I knocked on her door, waited a moment, watched the door swing open, and there she was. Wow. She was even more stunning than I remembered, her auburn brown hair flowing down her back, deep blue eyes holding my own eyes in place even though I wanted desperately to lower them to take in her incredible body. She was wearing a cute outfit: tight green t-shirt with a black mini-skirt and sexy high-heels. I was starting to have reservations about taking her out, knowing what kind of attention I would have to compete with. She diffused my worries with a smile, reached out for my hand and took me inside. “Wow. You look incredible.” I offered, lamely.

“Thanks. You’re looking pretty sharp yourself!” Chloe responded graciously and led me to the living room. “This is my roommate, Jessica. Jess, this is Jack.” Jessica was a pretty redhead, with bright blue eyes. Her hair was bouncing in a ponytail as she looked up from the couch and smiled, “Hello Jack. I’ve heard a lot about you. You be good to my girl here.” She looked at Chloe, “So. What are you two planning for the night?”

“Just thought we were going to hit a bar or two.” Jessica wrinkled her nose at Chloe’s response.

“Any suggestions?” I jump in.

“Yeah. You guys should stick around, hang out here.”

Chloe looked doubtfully at me. “I don’t know. What do you think? Stick around for a bit?

“Sure. I don’t mind hanging out here for awhile, having a few drinks beforehand.”

Jessica stood up. “It’s settled, then. Let me get you two something to drink while you think of something fun for us to do.” She moved into the kitchen.

I looked at Chloe and shrugged. “You have something in mind?”

“Actually, I think I do. I don’t know why, but I was thinking earlier that it’s been a long time since I’ve played truth or dare, and it was always so fun! What do you think? It might be a good way to get to know each other a little better.”

“Sure. Sounds like fun - I’m in.”

“What about you? Want to play truth or dare?” Chloe looked at her roommate Jessica as she was coming back into the room with two glasses of some kind of alcohol.

Jessica placed the glasses on the table, next to her own glass and bottle of wine, sat down on the couch and looked up. “You know I’m in, girl. But I’m telling you right now, I don’t play this third wheel stuff. We’re all friends here, right? You two can’t just truth or dare each other all night.”

Standing there thinking about it, this seemed like it could lead to trouble. More specifically, Jessica seemed like she could lead to trouble - she had a manic glint in her eyes.

“Of course. It’s more exciting with a third person, anyway.” Chloe assured her, taking a seat at the other end of the couch.

“Good. So let’s start! Me first. Jack...” Jessica paused and looked at me, up and down. Appraising me, I suppose, as if deciding how crazy a night I could handle. “Alright. Truth or dare, bad boy.”

“Straight to it. I’ll play it safe. Truth.” Still standing in front of them in the living room, I was starting to feel a little exposed.

“Oh, no. There is no playing safe! Truth it is then. Ready?” Jessica leaned forward on the couch. “What is your most frequent sexual fantasy?”

“Ummm. You know I’m on a date with your roommate, right?”

Chloe smiled, “No, I think this is a good question. I’d like to know what I’m getting into.”

What to do? Play it cool with a fake, boring fantasy? Nah. The mood is light, Chloe and Jessica seem like they’re fun and open-minded. Why not try being honest up front?

“So?” Jessica prodded.

“Ugh. Fine. I’ll be honest. Ass licking.”

“What?!” Chloe and Jessica exclaimed in unison. “Whoa!” Chloe was nervous laughing. I don’t think she knew how to process this new information about her date. She looked me in the eye, “Wait, giving or receiving?”

“Don’t worry. I’m a very giving guy.”

“Thanks for that, at least!” Chloe sputtered. Jessica burst out in a laugh. I started laughing with her, relieved that some of the tension in the room was draining, and that I wasn’t being pushed out the door.

“OK, so it’s my turn then. Chloe, truth or dare?”

“Wait, let’s talk about your answer a little more.”

I shook my head, “Nope, your turn. Truth or dare?”

Chloe was settling down. Jessica was radiating a supremely amused expression. “Fine. Truth.”

“Have you ever had your ass eaten before?”

Chloe shook her head vigorously at the direction this game was going. “I can’t believe we’re talking about this stuff.”

“You started the game.”

She sighed. “Fair enough. One guy licked me down there a little bit, but I think it was by accident.”

“Believe me, that was no accident.”

“Fine, but I didn’t like it. He seemed like he may have wanted to do it more, but it was so awkward.”

“So he didn’t know what he was doing.”

Jessica jumped in, smiling wickedly, “You saying you’d do it better, Jack?” Chloe shot her a look.

“I think I may be of some better service.” I smiled at Chloe. She blushed heavily and glanced down, but I could see her lips were curling up in a smirk.

“Your turn, Chloe.”

She looked back up and glared over at Jessica. “OK, Jessica. Truth or dare?”

Jessica was practically bouncing up and down on the couch, “This is fun you guys! I am learning so much about you two...” She laughed again, “Let’s do the truth, then.”

“What is your biggest sexual fantasy?”

Jessica looked knowingly at me, “Well, now I think it’s having Jack over here eat my ass out!”

“Very funny, Jess, stay away from my date.”

“Fine, for you Chloe, I’ll leave him alone. I guess I’d have to say, given my now limited options, I mostly fantasize about being on top of a guy while I’m sucking off another one. That’s usually how they end, but the scenarios leading up to that vary quite a bit.” Jessica was casual, matter-of-fact. A pause. “Is it my turn again?”

“Go for it.” I was anticipating anything at this point. Nervous. Excited. This was going better than I could have imagined. Thank you, Jessica!

“OK, Jack, truth or dare.”

“Let’s mix this up. Dare.”

“Yes! Finally! Alright then, Jack...” Jessica looked over at Chloe and gave a cat-like grin, “I dare you to come over here and lick Chloe’s ass!”

Chloe’s mouth dropped open; mine must’ve been dropped, too, because Jessica was snapping her fingers between us while grabbing her drink. “C’mon you two, I want to see this!”

Chloe glared at Jessica, “I am going to kill you!” But she stood up from the couch and started to turn around while unzipping her skirt. And then she smiled at me, the sexiest shy smile I’ve ever seen and muttered, “You want to do this, Jack?”

My mind was buzzing. I decided I needed more friends like Jessica in my life. “Fuck yes, but should we go into the other room?”

“No way!” Jessica blurted out, “You have to do this in front of me. Otherwise, there’s no proof that you did it. Anyone who plays truth or dare knows that rule!”

“Alright Jessica, then Jack and I are going to give you a show.” She looked over at me, “Get over here and let’s do this. And I hope this is better than the other time...” Chloe was now climbing onto the couch on her knees while her skirt slid down; she pulled her skirt under her knees and off past her high heels. Now she was just in a pink thong, her dark green t-shirt still on, and looking over her shoulder at me. She looked so incredibly sexy, and her ass was perfection, full and firm.

I swallowed and raised my eyebrows at Jessica, “You know you’re a pervert, right? You want to watch me lick your friend’s ass?”

Jessica giggled, “I’m the pervert? Please! You know this is turning you on like crazy! I’m just watching as a neutral, curious party...”

Chloe looked at Jessica, “Yeah, right. I bet if I leave the room for a second, you’d try to get him to lick your ass. You’re such a slut, Jess!”

“Says the girl letting a guy she barely knows eat her ass!”

They were both blushing and laughing now, so I thought I better move in before the mood changes in here. I walked quickly to the couch and, going to my knees behind her, started kneading Chloe’s beautiful butt in my hands, watching her pink thong disappear in her ass cheeks, then reappear, barely covering her asshole as I spread her cheeks wide, then push them together again. Chloe had her eyes closed as she lowered her head to the top of the couch, her long auburn hair draping over her upper back. She was going to let me do this! I glanced at Jessica who was acting cool and comfortable on the other end of the couch, but I could see the nervous excitement in her eyes as she watched us. I winked at her, then lowered my face into Chloe’s deep ass crack and slowly rubbed my face up and down between her butt cheeks while continuing to kneed them against my cheeks.

Looking past her shoulder, I could see a smile inch up on Chloe’s face as I slowly ground my face into her ass. The skin of her butt was so soft, and I felt the warmth between her cheeks as I breathed in deep. “Oh ... That’s nice.” She whispered. Jessica was quiet, but I could feel her stare on me. “I actually like this! But I think you were supposed to be licking, weren’t you?” Chloe teased. I saw her hand reach back as she pulled her thong out of her cheeks and over to the side. I pulled out of her ass and stared, awestruck, at her amazing butthole - a light-pink pucker, smooth and clean. In the corner of my eye I saw Jessica lean forward to get a view for herself. I extended my tongue, obscenely, trying to get a reaction from both Chloe and Jessica as I dipped it to the end of her pussy and dragged it up her ass crack, slowly over her anus and past. Her taste and smell were incredible, fresh and light. Chloe twitched involuntarily once I reached her asshole, but then I felt her tension leave her body as she sighed. I did this lick again, once, twice, three times - slowly every time. Then I gently spread her ass cheeks apart, and her asshole slightly gaped with the spread. I hardened my tongue and pressed firmly, but gently into the center of her anus, getting a little bit into her opening.

“Okay ... that’s good. That’s really good. Keep doing that.” Chloe whispered, her head still lowered and eyes closed. By contrast, Jessica’s eyes were wide open as she watched me rim her friend.

“What do you think?” I asked her.

Jessica was flustered. “Uhhh, I don’t know. It’s actually hotter than I expected. Fuck.” She drank some more and reached for the bottle while she composed herself. “I thought it would be weird, but Chloe,” she smiled at her friend, teasing, “You have a very pretty asshole.”

Chloe smiled back at her. “So what’s turning you on, Jess? My ass or his tongue?”

“Fuck you, Chloe. I’ll trade places with you in a second if you let me!”

Chloe laughed and flicked her hair to the side, “I don’t think so ... I kind of like how this is going. Now get back in my ass, Jack.” She pulled her thong completely over the side of her cheek and spread her other cheek with her free hand. I smiled over at Jessica and shrugged as I extended my tongue again, and again gently pressed it against Chloe’s butthole. This time, after I pressed my tongue to her balloon knot, I kept the pressure against it as I moved my tongue in a circle around her rim. I felt her hand move from pulling her cheek wide to the back of my head as she held my face up in her ass. “Ngh.” She grunted, pulling me into her. I continued to run my tongue around her asshole slowly while increasing pressure slightly. I could feel her anus tensing against my tongue, but starting to relax as it got used to my probing. After a few minutes, I tried to shove my tongue up inside her asshole. Chloe gasped. I didn’t get far, but I didn’t pull out fully as I pressed again up her butt.

“Whoa! His tongue is going up my ass, Jess! Fuck, it feels good...”

“Wait a second!” Jessica broke in, “I thought the dare was only for him to lick your ass, not give you a full-on rimjob!”

“Fuck you, Jess ... don’t stop, Jack. Don’t stop. Aaaaaaaaaagghhh this is soooooo goood!” I am pushing into her again and again.

I feel Jessica’s hands on the back of my head, peeling my face out of Chloe’s ass. “No! We continue the game. Get back, Jack.” I sit back staring at her for a few seconds, then theatrically express my reluctance as I get to my feet.

“Fine, Jess. You are such a bitch!” Chloe was having some trouble catching her breath. “Damnit Jack, you were right, that was sooooo much better than the other time.”

“And I didn’t even get started...” I smiled, still a little dumbfounded and dazed.

Chloe was fanning herself with her hand as she laid back into the couch, still only in her shirt and panties. “Damn, we’ll have to get back to it later then. Wow.”

Jessica was looking between us, smiling approvingly at me. “Well, I guess you’re up then, Jack.”

I ran my hand down my face to steady myself and tried to stay cool. “Alright, Jess. Truth or dare?”

“Fucking dare. And make it a good one!”

I looked over at Chloe. “Any suggestions?”

Chloe was starting to come back to her senses. “Yeah. You got a good look at my asshole, now let’s see yours.”

“Is that all?” Jessica stood up, removed her shorts and panties in one motion, got on her knees on the couch, and spread her butt cheeks lewdly apart, revealing her own pretty red rosebud. It was mostly just a dark-red hole, no ridges, and I found myself involuntarily drooling looking at it.

“What do you think, Jack? Whose is prettier?” Jessica smiled back at me, her bright blue eyes sparkling.

Chloe looked over at me dubiously, then back to Jessica. “Alright, game’s over. Jack, let’s go to my room.”

Jessica spun around quickly. “No! Wait, let’s keep going. This is so much fun! I’ll even dare Jack to eat your ass again. C’mon!” Chloe was just shaking her head as she walked over to me and grabbed my hand, leading us back to her bedroom. “Wait, Chloe! What am I going to do tonight, then?”

“I think we’ve given you enough of a show. Go do what you do whenever you fantasize about fucking a guy and blowing another one.”

“Ugh. Rip-off! I want my money back!” I heard Jessica laugh as Chloe brought me into her room and closed the door behind us.

“Phew ... So it’s just us now.” Chloe’s deep blue eyes locked onto mine. “You said something about not even started?” She gently pushed me over onto the bed.

“Hey,” I teased, “I thought you didn’t really like it. Something about it being awkward?”

She smiled. “Like you said, that guy didn’t know what he was doing. You definitely do.” She looked thoughtful. “You said that was your most frequent fantasy ... what are your others?”

“That’s pretty much it. Whenever I need to get in the mood, that’s what I’m thinking of.”

Chloe looked relieved and sat down on the bed, next to me. “Good. I mean, one new thing at a time for me.” She gave me a mock-coy, shy look, “I’m a good girl, you know.”

“So what does this good girl want to do now then? I’m guessing we’re not going out to the bar...”

“What do you think I want to do? I didn’t drag you in here for nothing.” She stared at me intensely. “I want you to finish what you started. I thought that’s what you wanted, too.”

“Fuck yes, I do. Thank you. Come here.” I reach over and pull her t-shirt over her head. She unlatches her bra as I slide off her high heels then push her gently onto her back on the bed.

“Oh. This is kind of a weird position to start in, isn’t it?”

“That’s alright, we’ll try a few out tonight if that’s cool with you.”

“Baby, you’re driving tonight, I’m just along for the ride.” She watches me as I lean in to kiss her, then slowly make my way down her sexy body, taking each firm breast in my mouth before continuing my kisses down her tight stomach. I draw her legs together as I grab her thong and pull it down, then up and off her legs. I put my lips back on her belly and slide my face down, past her shaved pussy with a few light licks. She gives some slight moans of anticipation, and I reach under her thighs and push her legs back. I was now on my knees on the floor in front of the bed, with her gorgeous asshole perched right at the end of the bed, right in my face, while my hands held her legs back. Chloe reached up and pulled her own legs back further, raising her asshole a bit off the bed. I glance up to see her looking down between her legs at my face, waiting. I guess that’s my cue, I thought.

I move my face into her butt. I start my tongue low, in her ass crack, then slide it up to her butthole. Chloe tenses again at the feeling, but quickly relaxes with a moan. “Yes. That does feel good. Lick my ass some more, Jack.” I continue licking, increasingly focusing on her anus. I flick my tongue rapidly in an up and down motion, then tilt my head sideways and repeat the action. “Oh fuck, that’s nice. Keep licking...” she trails off. At this point, her asshole is in perfect position for my mouth to suck. I’m not one to waste opportunities. I plant my lips around her anus in an airtight seal, and gently suck in. She gasps. I start rhythmically sucking, releasing, sucking, releasing, sucking a few extra seconds, releasing. Chloe is rocking her hips with my mouth, gyrating a bit against my suction on her butthole. “Oh yeah, oh hohoho, yeah.” She was murmuring through clenched teeth. I pull away with a smacking sound.

“Open your asshole for me, girl. Reach down and spread it, ok?”

I move my hands up to hold her legs back, while she reaches down and spreads her cheeks wide. I am surprised when she slips a finger inside her asshole. “Ohhhh.” She groans as she slides her finger around, “Come here, Jack.” She pulls her finger out and holds it to my face, “Taste this.” I eagerly take her finger in my mouth and suck, savoring the slightly salty and sweet flavor. “Fuck, that’s hot.” She pants as she resumes spreading her asshole wide for me.

I hardened my tongue and pushed into her gaping anus with a grunt. “Yes! Yes, yes, yes!” Chloe was chanting, now making something of a running commentary about what I was doing, “Yes, your tongue is up my ass, oh, wow, it’s so far. Ungh. Yes, out and in, again, yeah! There you go, wiggle it inside there, keep it up in my ass. Hold it there. Ha! Yes! More, more, more!” I loved hearing her like this, and I continued my enthusiastic explorations of her anus.

A few more minutes passed when Chloe startled and stared wide-eyed past me and what I was doing. “What the fuck are you doing Jess?” I turned around, and saw Jessica standing in the open doorway, holding a video camera up.

“Shhhh. Don’t mind me, you guys. I’m just enjoying the show.”

“How long have you been there.” Chloe didn’t sound mad.

“Pretty much the whole time. You two were a little occupied, so you didn’t notice.”

“This better not end up on the internet. I swear, I will kill you if it gets to anyone else.”

“No worries. Personal use only, I promise.”

“Fine. Okay. But no interrupting.” Chloe rolled over onto her stomach, now seemingly oblivious to Jessica’s presence in the room. “Let’s try this way for a little bit, Jack. That felt amazing, but my legs were falling asleep!”

I laughed. “Sounds good, but now I have to worry about camera angles.” I winked at Jessica, smiling back at me.

I looked back at Chloe, lying face-down on the bed, legs slightly spread, waiting for me. She turned to stare over her shoulder. “What are you waiting for? My ass won’t eat itself, you know.”

Jessica burst out with a laugh, “Whatever happened to my sweet, innocent Chloe? You are just a dirty girl, now!”

Chloe smiled lazily, “I don’t give a fuck anymore. Might as well join your club, right? And by the way, you’re not supposed to interfere here, so please, keep the comments to yourself.”

Jessica rolled her eyes, but moved herself and camera into position, closer on the bed. I climbed onto the bed, between Chloe’s legs, and pried them apart a little more to open her up a bit for the camera. OK, I admit, I was pretty excited at the prospect of seeing myself do this on video. I tried to ignore the camera, but I looked up at it as I returned my face into Chloe’s beautiful butt. I resumed my tongue fucking of her ass, spreading her cheeks wide and extending my tongue before pushing deep into her dark hole. I did this slowly for effect, and I heard Jessica catch her breath as I pushed in and pulled out with a POP, waiting and watching as Chloe’s gaping asshole closed up again. Over and over I did this; Chloe’s hands were gripping the sheets hard as she arched her butt up to meet my face repeatedly.

After a few minutes, she reached back with both hands and grabbed the back of my head. “Get...” panting, “ ... in...” panting, “ ... my...” panting, “ ... ass...” panting, “ ... you...” panting, “ ... fucking...” panting, “ ... slut...” panting, gripping my hair, pulling my face harder into her butt, my tongue sliding deep into her rectum. “Yes, yes, yes, yes, yeaaahhh!” I felt her cum dripping out of her pussy, smearing against my chin. Her body was shivering against my face. I pulled my tongue out of her anus and looked at what I had done. Her asshole was twitching, quivering. Jessica looked over at me and mouthed, “Wow,” her camera getting a good view of the aftermath. Suddenly, I felt Chloe’s hand again on the back of my head, pulling me back to her butt.

“Not done yet. You know you’re not done yet, Jack.” She started to slowly grind her ass up and down my face.

It took every ounce of my will power, but I leaned back, “Hold on. Let’s try a new position ... I want you to sit on my face.”

Chloe smiled and let go of my head. “Yeah, okay. That sounds hot. Get up here.” I climbed further up on the bed and laid down on my back. Chloe stood up, straddling my head, and I was looking up at her pussy and tits. She spread her ass, while Jessica got a nice close-up, then squatted down, carefully lowering her anus back onto my waiting mouth.

With my mouth full of her asshole, and nose pressed against her pussy, I reached up and grabbed her tits with both hands, squeezing and kneading them. Chloe leaned back, bracing her hands on my waist, and started grinding her asshole against my mouth, forwards and backwards. “Mmmph,” was all I could communicate, besides my own low moans of pleasure.

“Yeah, keep doing that, hum into my ass.”

What? I wasn’t even thinking about that, but my moaning was vibrating her asshole, providing an additional sensation for her to play with. I started humming while I licked and sucked her anus, my hands running all along her body now. Chloe was gyrating more energetically now, forward and back, in a circle, slowly then quickly then slowly again. I was loving every minute of this. She started to increase her pressure, bouncing a bit on my tongue, and I thought she was getting ready to orgasm again.

Chloe panted, while grinding. “You know, this feels so unbelievably good. But I don’t know if I can cum again right now, like this.”

“No problem.” I mumbled into her ass. I slid my hand around her hip and reached between her legs; I could see and feel she was incredibly wet, and I easily found her clitoris, slightly raised. I returned my tongue to her asshole as I rubbed her pussy and teased her clit with my hand.

She lasted about 30 seconds. “Ooooooohhhhhhh fuuuuuuuuck!” She cried out as her body racked convulsively to the pressures of my mouth and fingers. Her butt cheeks flexed against the sides of my face as I pushed hard into her asshole to feel her clench my tongue while she orgasmed. “Oh fuck, oh fuck, oh fuck.” Chloe continued to whisper as she continued to rub her ass on my face in a circle, slower and slower, calming down.

“Well, well, well.” Jessica sputtered, camera catching our dazed reactions. She sounded like she could barely breathe.

Chloe looked down at me, exhausted, but with an enormous grin on her face. “I don’t know, Jack ... I don’t think I’m done yet. What about you? Had enough of this ass?”

I instinctively looked at the camera, and couldn’t help giving a big stupid smile. I quickly composed myself. “Not even close to enough. Let me taste that thing.”

“Fucking-A you guys...” Jessica was holding the camera up to us, with her other hand up to her heart. “I don’t know if I can take much more of this!”

Chloe was starting to stand up, still straddling my head. “Well, you don’t have to stay for the rest. You can take that video and get yourself off, then.”

“Oh no you don’t. I’m catching the end of this.”

“Suit yourself.” Chloe turned around to face my legs. She was pulling her ass cheeks open then letting go, teasing me. “Okay, Jack, I really like it when you...”

“When I what?” I was staring at her pretty little starfruit, still wanting more than anything to taste it.

“Well, I like it all, but right now I think I need your tongue deep inside me. Can you tongue fuck my ass some more?” She laughed. “Fuck, that is something I never thought I would say. See what you’re doing to me, Jack?”

“Get down here.” I grab each of her thighs and pull her back on top of me. She quickly scoots her knees forward, positioning herself again, and reaches back to spread her butt cheeks just inches from my eyes. I gasp as she pulls her anus open, and I can see a bit into the deep red inside of her asshole. Unbelievably sexy. She leans forward to reposition herself just over my mouth, and I stick my tongue out, hard and wet, ready for her gaping anus.

She drops her ass onto my waiting face. My tongue slides right up her asshole, and she takes it with a grunt. “Unh.” I lift my head off of the bed, shoving my tongue as hard as I can into her opened rosebud, and start hammering my face and tongue into her butt like a piston. Her ass cheeks are making a nice slapping sound against my face that turns me on even more and I increase my speed. I reach both hands up to squeeze her breasts and hold on to them, using them to guide her whole body motions on my face. Chloe moves one hand to rub her pussy, and uses the other to grip the back of my neck and pace my tongue thrusts into her asshole. I wrap my arms around her hips and pull my face hard into her ass while she pulls up with her hand. She is riding my face, now, like a cowgirl, rocking back and forth, grinding her asshole on my mouth and tongue. After a few more minutes of this rimming, her moans are indecipherable, “Ohh. Uhn, yeah, mmmmm, in there ... Oh, oh, ohhhhh, ahhhhahaha, oophmmm ... My fuck, Jack, ohhhhooooooohhhhh, yes, mmmm, yeah!” I am crazy with desire and eating her ass furiously, consumed by lust, and we are reading each others’ minds with each thrust, probe, grind, kiss, lick, suck. Seconds become minutes, and we must continue in this position for at least half an hour, all while ever-present Jessica is circling around us, making small excited noises and comments, and capturing the moment on video. Chloe builds to one final, mountainous, explosive climax. “OoooooooooooohhhhhhOOOOOOOOOOHHHHHHHHHH!” Her juices are flowing all over my face, and I have the sense to continue rubbing and grinding my face into her ass and a bit in her pussy, while she returns to her senses and slowly calms down. Her grinding comes to a standstill, she leans back, butt still on my face, and breathes deeply in and out.

We are both completely out of breath. “So Chloe ... truth or dare?” I’m talking into her ass.

Chloe laughs, totally spent, “Fuck ... I need a break. Truth.”

“Was this your best second date, ever?”

“Ha!” She wiggles her ass against my face and looks over her shoulder at me, “I think this might be up there at the top. Best orgasms ever, absolutely.”

“And that’s a wrap.” Jessica pulls back and shuts off the camera. “Alright you guys, I think I need to head out for a drink somewhere. Don’t wait up.” She leaves the camera on the counter. “Go ahead and take a look at your star performance, Chloe. I’ll go through and edit it tomorrow. I think we definitely have some highlights.” She raises her eyebrows at me as she saunters out the door. Chloe and I look at each other and smile.

We enjoy each others’ company for a bit longer, exchanging knowing looks and suggestive comments, always skirting just around talking about what we just did together, but sending enough messages that both of us know we will be doing it again, soon. Finally, it’s time to call it a night. As I’m getting ready to leave, I can’t help but try one more thing, for fun and to add a little more levity. “Thanks for an amazing evening, Chloe ... Can I give your ass a goodbye kiss?”

She smiles, and shakes her head in disbelief, “You know, I seriously never do this kind of stuff. You make me such a bad girl, Jack. Okay, get over here and kiss her goodnight.” Chloe turns around, pulls down her panties and gives her ass a nice big spread, while I kneel down and take in the glorious sight of her butthole one more time. I sigh as I lean in and press my lips against her anus and give a long, lingering, smack of a kiss. Chloe giggles, pulls her panties back up, then turns around and slaps me on the shoulder. “You are such a bad boy...”

After making our final goodbyes for the date, I am standing outside again, staring at the night sky, thinking about how amazing this evening had been. Better than anything I could have imagined, really. I start across the parking lot, when I see a shadow a little ways away moving quickly and deliberately towards me. As I reach my car, my heart thumps until my brain processes the sharp clicking noise of high heels, and I recognize in the dim light Jessica coming over. Wait, what was she doing here?

“Finally, Jack! What else was there to do in there?” She comes to a stop and is now standing in front of me, in her tight light blue cami and white short-shorts, her red ponytail swaying slightly back and forth.

I can’t find words, just stare dumbly.

“So you’re going to make me say it, are you? Fine. I want to go back to your place. I want to do what you and Chloe just did.”

Whoa! What the hell is going on here? Is this some trick, to prove to Chloe that I’m not worthy of her? Is she serious? You would have to be blind and deaf to not recognize that she was definitely turned on by what we were doing...

“I don’t think it’s a good idea, Jess...” I blurt out, without really thinking.

“Oh, come on! Do you feel guilty about it? You barely know her! This is the second time you’ve seen each other, hardly what I’d call exclusive.”

“Well...” I stammer like an idiot.

“Well what? Are you worried she’ll find out?”

“I guess...”

Jessica cuts me off. “Believe me, I have way more to lose than you do if she ever found out, so you don’t have to worry about me talking.” She moves up to me, pressing her tight, soft, warm body against mine, and looks up into my eyes. She whispers, “Look. Do you want to eat my ass or not? Simple as that. And I’m pretty sure I know your answer considering the stare-down you gave it earlier tonight.”

My heart was pounding again. I didn’t even know what I was going to say next, it just poured out of me...

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Story tagged with:
Ma/Fa / Consensual / Heterosexual / True Story / Analingus / Oral Sex /