Taking Cara Business

by Nicolo Parenti

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Mult, Consensual, Romantic, BiSexual, Heterosexual, Fiction, Humor, Swinging, Group Sex, Oral Sex, Anal Sex, Double Penetration, .

Desc: Erotica Sex Story: Cara had become a good friend but issues from her past still haunted her. It would take more than everything I had to make her whole again.

"Good morning, Arrow Associates. This is Cara. How may I direct your call?"

I wouldn't last a week as a receptionist. I could never sound half that cheerful repeating the same thing forty times before noon. Not to mention keeping track so I didn't keep saying 'morning' at 3 pm. But Cara has been doing it for six months now while greeting the arriving staff and clients, keeping the coffee fresh and signing for deliveries. Of course, she's 19 years old and in her first real job while I'm a jaded 31 with a couple of workplaces in my rearview.

Call me Ishmael. I've always wanted to say that, but sadly my name is Dave. I know the score, I've been around the block, I wasn't born yesterday and so on. I do my job well enough, earning a salary commensurate with my skills and sufficient to my needs with a little left over for fun and various bad habits. By which I mean more fun.

Some of my bad habits don't cost money, at least not directly or not much. I like to smoke a little dope and have a drink or two with my crowd and I probably play a bit too much poker and a lot too much Madden and Halo. Plus I like to fuck young women, though I do hit a bit of a drought sometimes. Whether fucking around has any psychic cost is debatable, but I can claim to never having 'paid for it' as the saying goes. I've left no crazed stalkers and few hurt feelings in my wake.

I try not to get involved with women I work with, clients or colleagues, and I stay away from the marrieds. Mostly. So while Cara was certainly appealing in both form and face, someone I'd move on in another setting, I respect the rule my dad once articulated as "don't dip your pen in the company inkwell". He was much older.

So I'm single and on my own and my name is Ishmael. No, sorry, we covered that. Dave. I have a two bedroom flat in a trendy area with the second bedroom for out of town guests or a buddy with trouble at home. My drinking spots are within easy stumbling distance and work is on the bus route so my car stays garaged a lot, but once in a while if I'm running late or the weather's bad I'll drive in, as I did this day.

At times I'm less discreet than I could be and this was one occasion. I was in my car during lunch in a shady far corner of the lot, catching some tunes and having a quick vape. I actually do my job a little better with a slight buzz (no, really) and vaping doesn't leave me with a skunky aura. Anyway, I missed Cara's approach. Good thing I wasn't doing a joint 'cause I'd have spit a hot coal into my crotch when she tapped on the window and gave the old 'roll it down' sign. I was busted, but she was grinning.

"Hey Cara, what's up?" She was bending over slightly to see in, which opened her top just enough to give a glimpse of a lacy black bra. I'm sure her firm young breasts didn't really need a bra, but there's my mind wandering again. And I was probably staring, and of course she knew it. Busted twice.

"Hey Dave. Looks like you're enjoying lunch more than I did. What's that you're listening to? It sounds kinda old. But cool," she quickly added.

It was old for me too. "Oh uh, it's my '80s punk channel on Pandora. I got hooked a couple years ago and sometimes I rotate into it when I'm having a ... um, when I'm feeling a little mellow."

She grinned even wider. "Yeah, I can see you're a little mellow. Well, I better get in there. Those phones won't answer themselves." And with that she was gone. I wasn't as busted as I could have been. Two drops of Visine and it was back to the grind.

This became a thing. When I drove, which I made a point to do more often, she'd come out to visit at lunch. We'd chat in the car, checking out each other's tastes in music. I think I expanded hers more than she did mine but I still discovered some bands I wouldn't have gotten to on my own. I always offered her hits of the vape but she always demurred.

So we were work buds. It was a little weird with our different ages, but she seemed like an old soul and she made me feel like a younger one. Against all odds she seemed to prefer my company to the few others her age at work. I know I preferred hers. She was a devastating mimic and could just nail the folks we worked with. She cracked me up and I guess I entertained her too.

I'd be lying if I said I didn't find her attractive. I mean, what's not to like? She's a cute young blond with a killer body, a nice set of brains and personality out to here. Dresses well, laughs easily, will tolerate an occasional Husker Du or Dead Kennedys set. That alone marks her as discerning.

We'd gotten pretty comfortable in the front seat, to the point where her hand might stray to my leg as she was telling a story. It burned, oh dude it burned. To deflect I'd ask about her boyfriends. She deflected back. I got the idea she didn't go out much and had no steady men in her life, which was crazy because she was hot in so many ways. Uh oh, I might be about to break Rule Number 7 here. Sorry dad.

One rainy day I decided to bend the rule by offering her a ride home, partly to be nice - she was a bus rider too, not so much by choice - but also to check out where she lived. She directed me to a small house a few miles away. 'House' surprised me because receptionists in this town don't buy or even rent houses, they share one-bedrooms in cheap apartment blocks.

"Ok, here you go. Say hi to your roommates for me."

She looked surprised. She'd never mentioned her living arrangements so I thought I'd guessed right. Wrong.

"No, I live alone, ever since my parents died. I grew up here." She looked wistfully at the house and I felt like a jerk for making casual assumptions. But hell, how was I supposed to know? She'd never said a thing. Plus I often feel like a jerk so that was nothing new. Only 19 and both parents gone? Sad stuff.

"Oops, sorry Cara. I didn't know."

"That's ok, It's been over a year and I'm doing pretty good. Moving on. But hey, thanks for the ride, see you tomorrow." She gave me a quick peck on the cheek and bounced out. That burned a little too.

This happened a few more times over the next weeks, not regular but more than casual. Then one day we'd just arrived at her place and were idling as she reached for the door handle, then hesitated.

"Umm ... do you have dinner plans? I've got some pasta and I'd like to sort of pay you back a little for the gas and all. Wanna come in?"

Little head said, 'Yes, Cara. Yes, I want to come in ... you'. Ouch, slap your mouth you filthy cur. Instead I said, "Ah, sure, I'm game. Nothing on tonight but carousing with the other sad sacks at Guilio's. I'll bet your pasta's better than a cheap bar burger."

She beamed. "Great. Pull in the back and I'll get things started."

We had a fine time. The pasta was al dente and it paired well with cheap red plonk. She was looser, funnier and more upbeat than I'd seen her at work, I guess because she was on her own turf here, with her tunes on the box. Some of them I even recognized, thanks to her coaching.

When I pulled out the vape and raised my eyebrows in query she made a 'sure, go ahead' gesture. I took a hit and offered it to her as usual. She'd always declined in the past but this time I saw a hesitation before the No.

"What's the deal with you and weed?" I asked casually. "I can't believe anyone your age hasn't tried it. Hell, even at my high school it was as common as beer."

She couldn't meet my eyes. "It's not that. It's just..." She stopped and seemed to come to a decision. "I have tried it, more than tried it. But I learned something that made me quit. Now I don't smoke when I'm with people. And I'm not a loner stoner so that means pretty much never any more."

Now she looked at me closely, trying I guess to gauge my reaction. "The thing is, when I get high I get horny. Really horny. And my judgment goes on vacation. The last time I smoked at a party I did some stuff I'd never do when I'm straight, and I knew I had to put weed behind me."

Wow. I was getting a chubby just seeing scenes in my head. I was way curious and my imagination was in overdrive. I couldn't very well ask her for details, right? Yeah, but when I'm buzzed sometimes my tongue gets ahead of my brain.

"What, like a gang bang or something?" Oh shit did I just say that out loud?

She gave me an odd look. "Yeah, or something. You really want to hear this?" I nodded, maybe too enthusiastically. "Well, I got more than one date or party invite because people knew I was slutty when I got my smoke on. I knew it too and didn't care. For most of us Molly, X, was the party drug. For me it was pot. I'm lucky it wasn't crack or I'd probably be a dead whore now. So anyway I don't do weed anymore because it makes me a different person. One I don't think you'd like."

In my head I'm all: 'Oh yeah? I might like you just fine when you're high and horny'. Out loud I was more: "Hey, sorry. Sometimes I talk without thinking. Dope can switch off the filters, you know? Ah, hell, of course you do, that's what you're telling me. I'll shut up now."

She managed a small smile at my expense. "So that's my sordid past. I really like you, you know, and I don't want to lose you as a friend. But I had to get it out there or you'd always be offering and I'd always be saying no."

I was sure I'd say the wrong thing so I just put an arm around her. Somehow this turned into a hug and next I knew her face turned up and we couldn't resist a kiss, which soon involved a tongue rassle.

We broke it off and Cara spoke with a low and intimate growl. "Mmm. I knew you'd be a good kisser. And oh, man, I can taste the weed and it gives me the shivers. I like that stuff too much, what it does to me. But right now I don't need any help - I've been horny for you all week. If you don't want to fuck me you better leave now." Not want to fuck her? Was she crazy? Was I?

"Oh Cara, baby, you have no idea. I'm yours for the evening, at the very least."

She popped up, switched the tunes to dance trance and started a sinuous and sexy motion, inviting me up with an offered hand. I tried to keep up, to match her moves that seemed to both follow and ignore the pulse of the music, but it was hopeless. Mostly I just shuffled in place while she wriggled her snaky slim young body around my decidedly older and more boneful one. Shoulder-length curls swayed across her face, hiding and revealing lovely deep green eyes. I reached out to embrace her but she was smoke in my arms. Christ I was high, and not just on the weed.

"We" danced for about ten minutes and as we moved she started shedding clothes. She slipped off her top to reveal that sexy bra, then did something eel-like to get out of her slacks, never losing the dance moves. She could make a fortune at a strip club, no pole needed.

Her eyes bored into mine then she turned away so I could work the clasp. She dropped the straps and then the bra itself, displaying a fine feminine back. She looked over her shoulder with hooded eyes.

She pushed her panties down her thighs, past her nicely muscled calves and slim ankles until she was bent double at the waist. Even totally nude and moving to the beat she managed to keep her treasure hidden. But she couldn't hide a delicate fringe of dusky blonde hair in the pubic arch below. One of nature's wonders, that arch.

She beckoned me with another glance so I moved to join her. I reached under her arms to cup her breasts, my first experience of them with my palms instead of my eyes. I hefted the slight weight of her handfuls and rolled the nipples between my fingers, making her moan and push her lovely naked ass against my burgeoning erection. It was a very erotic moment, with this desirable young woman completely open to me.

I turned her and she melted into me, the music and the dance forgotten. She raised her face, eyes closed, to accept a kiss. Our mouths met and mingled wetly, our tongues in a dance of their own. My hands were on her ass now, pulling her against my steely cock.

We'd moved so quickly I'd still had no good view of her. I stepped back to rectify that. Oh man what a sight. There's something about youth that's sexy all by itself, but young, fit and gorgeous is even better. I swear if I looked like that I'd never wear clothes. Of course I have no reputation to consider or really even any morals, so my choices wouldn't suit everyone.

She looked at me quizzically. "Is everything OK? Don't you like me?" I guess I'd been staring. I shook off my reverie.

"Like? Oh, baby, you look like heaven. I just got lost there wondering if this was a dream or something. No, no, I like you just fine."

"Then why are you still wearing those clothes?"

We became a well-oiled team. I quickly started to work the buttons on my shirt as she flipped open my belt and pulled down the zipper. We had a little hitch getting the slacks over the obvious obstruction, and I had to help with the briefs or she might have taken Mr. Johnson off with them.

Cara knelt to fondle my cock and balls, lifting and inspecting, tugging and stroking as if she'd never seen the likes of them, which from her earlier revelation was probably way not the case. I was oozing in anticipation and, bless her heart, she took a little lick to clean me off.

"C'mon over here, Cara. I need to check out your parts too." I steered her to the sofa, sat her down and spread those luscious slim thighs. She sported a nice sparse little bush just as nature intended, a little darker and a little coarser than her blonde curls.

We were both eager but I slowed down a bit, reaching up to tweak her nipples and spreading kisses and licks around her sweat-salty torso, blazing a trail down to the vee at the top of her legs. Once at the forest I fished around a bit to clear a path then leaned in to nibble.

I parted her lips with my fingers and tongue, nuzzling and probing to get at the heart of what was by now a steaming furnace. She fell back and I went to work gently, teasing her clit just often enough. I wanted to keep her going until she could only do one thing.

I added a finger, then two, stroking into her pussy in rhythm with my licks. I think she liked it because soon her hands found the back of my head and pressed me deeper. I accepted the signal and went all out on her clit, sucking it in and flicking it rhythmically with my fingers fully embedded and curling to press the magic spot inside. Her hips rose off the seat and she strained against me while making an "unh, unh" sound. She was at the cusp of a massive orgasm.

And nothing. She stayed right there, at the peak but not over it, one Sherpa shy of the summit. After a few more minutes she collapsed and burst into tears. Sobbing "Sorry, I'm sorry" she pushed me away, jumped up, ran to the bathroom and slammed the door.

What the fuck just happened? Well, I mean, I know what happened but why? I've never seen a woman more ready to climax and my little tricks had never failed me. Stunned as I was I managed to get up, my dick as hard as wood, and tap on the door. "Hey, you OK in there? Can I get you anything, a towel, a glass of water..." I was still a little high, OK? Don't judge me.

The crying had turned hiccuppy, if that's a word. "I'm sorry, D-Dave. G-just g-go please. Sorry. It's n-not you."

"Um, sure Cara, if you're OK. Call me if you want to talk, or text me or something." I undid all the hard work we'd done getting me naked, losing my erection in the process. Shaking my head, confused and a little worried, I headed back to my place. I almost stopped at the bar but I didn't want to be with my usual crowd just then.

I didn't sleep well. Twice I'd called and twice it went right to voice mail. Texts evaporated into the ether. I checked her Facebook but her last status was from yesterday morning. I was worried but, being a guy and all, I started to get over it. I'd find out or I wouldn't. Like Fanny Lu said: Manana es otro dia. Es verdad, Fanny.

I took the car to work the next day just in case. Cara was at the front desk, cheerful as usual and busy enough that I couldn't do more than say hi and ask discreetly if she was all right. I got back just a professional smile and a nod. This, I thought. This is why Rule Number 7.

My morning was full and lunchtime came quickly. I took a sandwich out to the car as I often did, but the music didn't have any snap. I resisted vaping because I wanted a clear brain in case Cara came by. She didn't.

I tried to catch her after work but I had a late meeting. After one more unanswered text I decided I was being stalkerish. She knew where I was and she'd find me if she wanted to. Meanwhile I had some pals at a tavern or two I could visit and if not exactly drown my sorrows, at least hold them under until they stopped squirming.

I gradually came to realize my friend wasn't coming back. I could grieve or I could rage but I couldn't change it. The hell of it was I still didn't know what I'd done wrong. Sure, "It's not you it's me" but that usually means "It's you". And of course I saw her every day. I considered having "Rule #7" tattooed in reverse on my forehead. Also, some rule about how sex can ruin friendships. I don't know the number but it's got to be in the low single digits.

So I slipped back into my old life, rode the bus most days and even bought a bike to try to stave off the creeping ruin of my aging body by commuting on two wheels. It turns out this is sweaty work, often hampered by weather, and not all that rewarding. But it did spark a few conversations with women who didn't know any of that so I kept it up until the bike was stolen.


After a few weeks I was normal again. Things were going well at work, I got some killer bud from a friend in Colorado, and my bar trivia team took ninth in a national contest. Woot, amirite? Yeah well it's better than moping.

Then one night I was with some of our usual crowd of shiftless guys and gals at The Brick, two beers into a buzz, when a vision appeared at the door. Cara was scanning the room and looking mighty fine in a fringe vest and skinny jeans. Egomaniac that I am I assumed she was looking for me so I stood and waved dorkily. It took my breath a little when she caught sight of me and beamed. I hadn't realized how much I missed that happy, open smile.

"Hey Dave! So this is where you spend Wednesday nights. I must've checked every dive for blocks!"

A whole knot of questions vied for front-of-brain. Did this mean she was over her ... whatever it was? Why now and why here, when she could have caught me any day at work? Is she wearing underwear? What's the best temperature to serve lager? Not all those thoughts should have been in the queue, I know.

My pals were showing interest. None of them knew Cara. I'd never mentioned her or our work friendship, let alone our abortive turn as lovers. As she made her way to us Paulie leaned over. "Yeeoh, who's your friend there Dave? That is some prime young horseflesh. What have you been keeping from us? A long-lost daughter?"

Rita piped up too. "Oh, those eyes. And those jeans. Check out the gap at the top of her legs. A gal could get lost in there." Rita has been known to switch sides. I'm not even sure she has a preferred side. She'd certainly spotted that arch in a hurry, which reminded me a little painfully of the time not long ago I'd seen it up close and personal.

"Can it, you ignorant boors," I said with a defusing grin. "Cara is quality, too fine for the likes of this bunch. She must have lost a bet."

"Cara, is it? Well, get us introduced and get her a drink. Oh," said Paulie innocently, "she is old enough to drink, right?" Bastard.

We were six at a round top for eight. Cara took the empty seat between Tess and me, which clockwise made it Cara, Tess, Paulie, TJ, Rita, Chris and Dave (that's me!). I made introductions but while 'Cara' was easy for them, I can't imagine she'd match five new names and faces after a beer or two. I know I never could. You, well, don't even try. You're drunk.

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.

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