Second Date Rimjob

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."