Taking Cara Business

We were regulars here so no one carded Cara, they just assumed she was legal like us. We poured her a glass from the current pitcher and she saluted us.

"Cheers!" There were a few desultory clinks. "Dave talks about you guys sometimes so I feel like I know some of you."

Everyone wanted to know what Dave said about them but she was coy. Actually I'd just mentioned a few of them in passing. I sure didn't share their life stories; I didn't know that much. We were more drinking club than therapy group, social but superficial. Even what sex there was, was just casual.

Everyone liked Cara and the evening went quickly. We were all pleasantly tipsy by 10:30 when the group started to break up. This one had an early meeting, that one had a hungry cat, and soon it was down to just Rita, Paulie, me and Cara. I saw Rita give Paulie "that look" and they too made their excuses. Someone's getting some tonight. Maybe we'll all get lucky, though with Rita it isn't so much about luck as propinquity.

I didn't want to make any mistakes here, but Cara had reached out and I hoped that meant a resumption of at least friendship and at best carnal relations. I figure she did it publicly to make it easier to split if I was frosty. As if.

"I've got coffee at home, just around the corner and up the street," I said. "You're welcome to stop by. And stay for breakfast." Smooth, eh?

"Thanks Dave, coffee sounds good. We'll see about breakfast."

The night air refreshed and sobered us as we walked the few blocks. While I ground some beans and set out mugs, Cara spent a few minutes exploring the flat and commenting on the accumulation of stuff that had mostly become invisible to me over the years.

It took maybe ten minutes until we'd settled in with our Colombian, she on the sofa with her legs tucked up, me on a chair opposite. I didn't want to crowd her - this was her party and she should make the calls. She peered at me over the rim of her cup and spoke hesitantly.

"So, this is probably as awkward for you as for me. I've been a little bitch this month and I need to apologize for... no, wait, let me finish, for ignoring you. Friends don't treat each other like that. I'm sorry, and I don't know if I can explain, but just listen."

I wanted to hug and reassure her but it didn't seem like the right time yet. She looked small, sad and vulnerable. Also, hot as hell. I'm an ass, I know. I did want us to be friends, but after that taste of her pussy I also wanted to fuck her into next Tuesday. I kept picturing those firm young tits and sparse blonde bush. I squirmed a bit.

By the way, notice I hadn't pulled out my dope. I had a sense this was part of what had happened and I wanted to leave it out of the picture for now. But even there she had me.

"You're fidgeting, Dave. Go ahead and toke up, it's OK, I won't freak out."

I didn't. I just raised my hand to acknowledge what she'd said, to encourage her to continue.

"You really had me going that night. I don't think I've ever been as turned on and so close to a climax. And I wanted to come, Dave, for both our sakes. But I couldn't. I never can with a guy, well, with one guy." She hung her head. "I'm fucked up, Dave. Fucked up by my own head and the things I've done. I get close and I hang there, waiting for the rest of it, waiting for that second pair of hands, the cock nudging my ass, a nipple or a clit under my tongue. More, I need more. I'm sorry Dave. I started something I couldn't finish and left both of us frustrated."

The tears in her eyes broke my resolve. I moved over to lift her chin and bring her into a hug. "It's OK, Cara, it's OK. We all have baggage we'd like to shed, stuff that messed with our heads. Don't apologize to me, forgive yourself if you need to. God knows I'm no one to judge. Girl, you're nineteen years old. You don't really even have a past yet. Life is as wide open as you want. And it only goes forward. No back button."

Yeah, I know, nice platitudes. But I did sort of mean it. Regret can be paralyzing, forgiving yourself difficult. We get stuck in emotional ruts.

"I'm trying to go forward. I dumped my old friends because they all just know me as that dope slut. I had a new friend but I screwed up and pushed him away." She gave me a puppy-dog look to drive home the obvious point. "I want to connect again, get back in the game. And it's twenty."

She lost me. "Ah, twenty?"

"I'm not nineteen. My birthday was two weeks ago." Fuck me, another reason why this sucked.

All this time I'd been sneaking feels. Sure she's fragile right now but what better time to break through the barriers? I took her hand and placed it on the bulge in my slacks. God I'm an asshole. But she squeezed it. I may not always do the right thing, but I know when a woman needs fucking.

"You're pathetic," she laughed. "I'm baring my soul and all you offer is your dick."

I feigned indignation. "It's the closest thing to a soul I have."

"Yeah, yeah, I get it," she chuckled, "time to lighten up. I do like you, Dave, and I do want to get sexy with you. I just need patience. I have to learn a whole new way if I ever want to live like a straight person." She squeezed again. "Let's get this out and see what it likes."

We didn't undress. She just unzipped me, fished out my cock and dropped her head to my lap. I made a noise she correctly interpreted as satisfaction. I was fully erect in a few heartbeats and she drove me crazy with nips, licks and deep slurping sucks. I've had blowjobs, lots of them, but this was the first time anyone ever worshiped my cock. She brought me to the edge and backed off, then again, and again. She was doing what I had done to her but for me there was no hangup. One of these cycles I was going to pop.

"Oh, Loosee, you... you gonna make me essplode." Cara ignored my admittedly ill-timed Ricky Ricardo imitation. She took me even deeper, right down to the root, and looked up to watch my reaction. I lost it. I hadn't had sex in a couple of weeks and all the stored up energy and fluids came to a single point at the tip of my dick and boiled out into her warm sucking throat. She pulled back and her cheeks hollowed in as she started a strong suction on just the head. I think I screamed as she drained me.

Eventually I came down. "Holy... fuck Cara. Holy fuck. Oh shit that was fantastic. I think you collapsed something in there. No one has ever got me off like that. Well," I couldn't resist, "not since I was an altar boy, anyway." She fell back laughing and I attacked her with tickles and kisses. So her lips were spermy, big deal. It was all good. We were all good.

I made a move to return the favor but she pushed me away. "We tried that, remember? I need cock, not tongue. Anyway, I got pleasure making you come like that." Nice way to let me off the hook.

"Ok, but you know you cheated yourself because I'm down for the count. I may not get hard again for a week."

She glanced at the clock. "You've got exactly 17 and a half hours. Better take your vitamins because you're going to fuck me right here on this couch tomorrow and no excuses." Hey, she could do clock math in her head. Sexy and sexagesimal, what more could a guy want?

"Ok, I guess I can manage," I grumbled. "You're quite the taskmaster." I switched gears. "So, about breakfast..."

====================

Next day was a workday so we had to scramble in the morning with no time for fooling around. We did stop by her place to get her a fresh outfit. I was encouraged that I'd managed a boner from spooning during the night, proof of life after that marvelous blow job.

At work I was more peppy than usual and I suppose the more perceptive of my colleagues were thinking "Ooh, somebody got laid" but so what. Cara was her usual perky self, no clues for anyone to read. I don't think anyone saw us arrive together in my car, but again, who really cares.

The day dragged by in meetings and bids and reviews. I lunched with clients so no parking lot today. By the time I got out of there Cara was gone. I made my way home figuring we'd connect later. Imagine my surprise when I pulled in and saw her sitting on the little shared patio at the back of my building. Leaving nothing to chance, I see.

We ordered in because A) I had no food and B) I can't cook food when I have any, not for guests anyway. Having good Thai delivered is way better than starving, which is just barely worse than Cheetos and ramen. Yes, I've dined on Cheetos and ramen, when mac and cheese was too expensive.

Afterward we settled on the sofa with Cara tucked into the crook of my arm as we continued our casual chatting from dinner. There was no tension in the air because we both knew where this was going. Any "will she / won't he" was absent: we were going to fuck and the only question was timing. It was like we were old lovers who'd been doing this for years.

We started snogging, necking, making out like teens in the back of a car. It was nice and it proceeded to groping and eventually to nakedness.

"Cara, I know you mentioned sex on the sofa but I think we'd be better off in the bedroom. Softer, more room?"

"Nope, maybe later. First one's gotta be right here. You promised." I had?

We were already unclothed and entwined, so we stayed. She reclined with her legs spread, completely open and on display for me, her sex moist and reddening in anticipation. There was no need for foreplay: we'd been doing that in our heads since yesterday. She grabbed my cock and drew me toward her. I gazed intently into her eyes and she gazed back. I wanted to see her face at the moment I entered her, to imprint an image of this joining.

It isn't often a first coupling goes perfectly. There are problems of alignment, lubrication, leverage and all the rest. This was no different but we adjusted. I took hold of my cock and rubbed it up and down her slit, wetting it with her flowing juices and teasing her sensitive lips and clit. At the bottom of one stroke I found her entrance and pushed forward with true intent. She gasped and for a moment I lost her gaze as her eyes closed and she retreated inward. As I pressed on she came back to me.

I've been in a girl or two, younger and older, big and small, and if there's one thing I know for sure it's that until you put your dick in there's no way to know what it's going to be like. Sure, in some sense all pussies are the same just like all cocks are but it's the differences that matter and they're not always subtle and they don't show in her looks, her walk, her size or her shape. You have to fuck her to find out.

Cara had a fine, fine pussy. For all her talk of multi-sex I half expected a loose swamp of a thing but this was tight, slick snapping turtle pussy. As I pushed farther in she opened like a flower, offering neither resistance nor assistance, accepting my cock as her due. It went in and in and she made me feel a foot long.

Her inner walls were that wonderful combination of grasping and yielding, buttery and knobby no one has ever duplicated in a sex toy. As far as I know, and really how would I? I was one stroke into this fuck and I already knew it was going to be one for the books. I hoped Cara could come along for the ride, this was for her after all, but no matter what she got or didn't get I already knew there'd be one happy Dave when the night was over.

Our pubes met and she opened her mouth in a silent "O" as I contacted her clit and pressed against her cervix. We were a perfect match in length and depth, again something you can't judge from looks alone. We rotated and gyrated to confirm touchdown, then I began to pull out.

The retreat was just as nice. She whimpered with loss as I came almost all the way out, raising her hips to maintain penetration. I stroked in again with more speed and force, and so began the main event. I kept up a steady rhythm neither too slow to excite nor too fast to please, a beat I could maintain for hours if necessary. I mean minutes, of course.

"Fuck me Dave, keep fucking me just like that. Oh god I missed this. Bite my nipples, finger my asshole, do it all. Make me come."

Missionary sex makes it awkward for a taller guy to get at the nipples, and raised up on both arms I had nothing left to finger with. Yes, I know these are the kind of problems we should all have but the lady asked and I wanted to oblige. After we'd been at it long enough to bring me way too close to orgasm, I offered an alternative.

"Let's switch around, honey. I hate to lose sight of your lovely face but I think doggy might be good right now."

She agreed, and in seconds she was on elbows and knees and I was enjoying a whole different feel of her pussy and a view of her winking little hole. But this position was also more stimulating and I was trying to last long enough to get her off.

"Oh, Cara baby I don't know how long I can last with your pussy milking me like this."

"Play with my butt, Dave. Put your thumb in it. Oh, yes, like that. Do two fingers, like another cock. I need cocks, Dave. Tell me what the dick in my ass is doing while you fuck my cunt." She was rubbing herself like mad as I plundered both her holes and her fuck-talk was driving me to the edge. She may have had the pussy of a teen virgin but she had the mouth of a pirate's concubine. The combination was delectable.

I couldn't do this much longer and she gave no indication of being ready even after almost twenty minutes of fucking, fingering and frigging. I was way outside my usual zone. "Can you do it, baby? Are you close? I want us to come together but you've got me so hot. I gotta come pretty soon. Come on, Cara, let it go, let these two cocks get you off, the cock in your ass is going to pop too, you'll be flooded with our juices."

She nearly screamed. "Do it! Do it! Come in my pussy and ass, fill me with sperm, make me your fucking bitch, come NOW!"

With one last deep thrust I pinned her down on the mattress, my cock pumping slimy ropes into her. My fingers continued to plunge into her asshole until I froze them deep inside as well. This was indeed an epic climax for me. I collapsed onto her back, panting with the effort.

"Oh, Cara, oh baby, what a fuck. I sure hope you came because you really worked for it, you deserve it."

She was limp and silent. Not crying, not anything. God damn it, she hadn't come. What the hell more could we do? Oral, doggy, dirty talk, a fantasy ass fuck, the only thing we hadn't tried was whips and chains. I'm not into that and I don't think she was either, but if that's what she needed by god I'd get out the ball gag. If only I had one. At least in this position she couldn't get up and run away like last time.

I rolled off. "Honey? You ok? Talk to me, don't shut me out. I want there to be an 'us' here, I want to know what you're thinking and feeling, how we can work this out together."

"It's no good Dave. I'm damaged. I can't be the lover you need, I can't be a girlfriend. I'm a fucking slut who can't even get off on the one cock she cares about."

"Cara, I'm a pretty square guy. I don't know what else we can do but if you have a way for us to get you what you need I'm open to it. It obviously isn't physical, your parts seem to work just fine. So what's in your head? How do we make it the way you have to have it?"

She was quiet for a while. "You'll hate me. I'll lose you, and I can't lose you. You're good to me, we're good together in every other way but this. I want it to be different but I can't force it. Maybe after a while I can undo all the crap in my head but right now..."

"What? I'm here for you. Tell me anything, I won't ever hate you."

She was silent again, then: "How close are you to Paulie and Rita? I know they're fucking, I could see it the other night and I could feel his eyes on me so I know he's a player. Do they swing?"

I thought I was ready for anything but that one got me. "Ah, it's not like that really. Rita will do anyone, and I don't mean just guys, when the mood strikes. Rita's fucked all of us, Paulie just happened to be handy. Look, I know Paulie well enough to know he'd love to fuck you if that's what you're asking, and like I said Rita's easy. But I'll be honest, that's a new one for me. I'd need your guidance on how we go about it."

See how open-minded I am? But I felt a coldness creep into me. If Paulie fucked her, would it end us? Could I take it, and did I really even care? If this was just about sex for me, why would it matter? Yeah, but somehow that didn't feel like the right question anymore.

"Could we try? I don't want to mess up your friendships, and I sure don't want to get another reputation with a new crowd, but if we can keep it on the DL I'm pretty sure it'll be good for all of us, especially me. And don't worry, I'll be your girl. Dicks and clits are just things. I already have more than that with you and I want to keep it if we can."

Well, how can you argue with logic like that? Wait, was that logic? I didn't hear any syllogisms in there, she'd lost me somewhere around clits and dicks. But she's a persuasive debater and not just because she was stroking the cock I thought was dead back into a fresh state of arousal. A smart guy once said it's hard to think when you're hard. Yogi Berra? Abe Lincoln?

"Fuck it, Cara. I want you to get off and I want to be there. I know it'd be fantastic because I've seen how worked up you get. You going over the top must be a trip. So even if it takes more folks to do it, I'm in. I'll get Paulie on board - you read him right when you said he's a player. I don't know if he's ever done a three- or foursome, but if it means a shot at you I'm sure he's game. And Rita, well, no problem. She'd do a horse if it bought her a drink. Do we even need Rita?" Listen to me: one taste and I'm a co-conspirator. Backbone, it's what makes us men.

She was wiser than me. "I think it has to be a couple, Dave. With only guys it'd be competitive and all that negative shit. With a couple it's a shared experience. Besides, I like a little pussy and I bet you'd like to watch."

I took a mental step back and thought about this conversation. A girl I don't even know her birthday is roping me into a four-way fuck fest with a drinking pal and our slutty buddy Rita, none of which I was thinking about before today and I'm the old guy in this. For fuck's sake she's nineteen years old and she's already so jaded she needs two cocks before coffee! Twenty, I mean twenty. But still.

And naturally she's got me. I promised Cara I'd talk to Paulie tomorrow, then flicked off the light so we could get some sleep. Popped a little snuggle stiffie that night too. I think the exercise is good for it.

====================

"Don't fuck with me Dave, I'm not in the mood." Paulie was having a hard time taking in what I was saying. To be fair, I had fucked with him in the past and he me. It was our national pastime, that and bar trivia and poker and smoking dope.

"I'm serious, Paul, if you ever trusted me... wait man, wait... ok if you could trust me now... what? Oh fuck it. You don't have the only dick on the planet or even in this bar. You don't want in, I can go down the stools here and... Hey Bill! How'd you like to..."

"Ok, ok, ok. Take a pill, geez. Say I believe you. Why would you want to share the lovely Cara? I don't deny I had some very dirty thoughts after meeting her that night. I had to fuck Rita just to take the edge off, not that that's a bad thing."

I didn't see any need for the whole truth. "It's just that she's heard about threesomes and wants to try something new. She's very adventurous and open, she wants to broaden her horizons. I told her I'd find someone and she's already met you so why not?"

He was thinking about it. "You're serious, like for real? What aren't you telling me? I don't have to suck your dick or anything, right?"