Sex on tour (mf and then mf) | 2016

A little while ago I wrote the story of the first time I had sex. It was sweet, I thought it was touching, it was full of naive romanticism, and everybody absolutely hated it. It only got about twelve upvotes and I’ve got this sinking feeling that quite possibly a lot of those may have been from errant fingers mistakenly tapping the up arrow. Not to be paranoid or anything. Now I don’t want to scare anybody off, but this is the followup to that story. But don’t head for the hills just yet. I can hear the “hell no you won’t!!!” coming from all corners, triple exclamation marks and all, and I’m here to tell you that I got the message. I promise you that I will steer clear of any mushiness or overly emotional displays. The words “doe-eyed sentimentalist” will not appear in this post. No siree. Because in this story I will stick to the facts, and the more sexy or salacious those facts are, the better. There are plenty of those fact things to go around this time around anyway, and I’ll try to keep a brisk pace. But first, if you haven’t read that first story, well, I guess you should count yourself lucky. But also, a really short recap is in order, so the first paragraph is for you.

The first girl I had sex with was a bit of a tomboy. She was short and she had short black hair and small breasts and very little hips to speak of. Her ass was also quite average. And she was always wearing jeans and black hoodies and sneakers. Despite all this, she was still very cute. Especially if you’re like me and you’re into that kind of girl. And I know I’m not the only one who’s like me because the girl was very popular. She was in a band and she was always hanging out with tons of people, most of whom were guys. She was always busy and we only saw each other once a month. And if I thought that us having sex would change that, I was dearly mistaken. Because after that first time, it was once again weeks before I saw her again.

I really liked the girl so I took the rejection kind of hard. But I was eighteen and somehow I managed to go through the five stages of grief in record time. Ms. Kübler-Ross would have been proud (c’mon, google it, you know you want to) Denial (surely she’ll call me tomorrow) Anger (the bitch) Bargaining (maybe if I just don’t text her for a couple of days) Depression (maybe I can watch all seven seasons of Buffy a couple of times to pass the time) and finally Acceptance (the hell with it, I’ve had sex FOUR TIMES now, I’ll find another girl)

Yep, that’s right, we did it four times on that night. The first couple of times were a tad awkward, but by morning she was on her hands and knees with me pounding away hard at her just-the-night-before-still-untouched pussy and she was moaning and her ass under my hands was all wet and slick from her sweat beading in the Saturday morning sunlight. Now that would turn any young eighteen-year-old into a hopeless romantic, right?

But anyway. By the time she finally called me back I really thought I was over her. But then I heard her voice over the phone and a part of me wasn’t so sure. I know I promised there would be no mushy sentimentalism in this story, so let’s just say that that part of me was my dick and leave it at that. Unfortunately for me though this wasn’t a booty call. This was a I’m-sorry-I-never-called-you-back-and-I-don’t-want-to-be-a-bitch-and-I-want-to-be-polite-so-I’m-calling-you-now call. Which of course I thought sucked. I tried not to show my disappointment but my poker face sucks, even over the phone, so I’m guessing she knew what was going on. So she invited me on a road trip.

Her band was playing a couple of gigs in another city about six hours away. Would I like to come? I thought the idea was nuts and I really didn’t feel like spending all that time in a car with a bunch of guys I didn’t know, but what else was I going to say? It’s not like my weekend plans couldn’t be cancelled. Buffy would understand.

So that’s how I ended up in an old beat up Dodge Caravan with Anna (that’s the girl’s name), her four bandmates (I really can’t be bothered coming up with good fake names right now so let’s just call them John, Paul, George and Ringo) and one really cute girlfriend (Stephanie). Stephanie was also eighteen and she had gorgeous long and curly blond hair. She also had these perfect white teeth that somehow drew the attention to her full pink lips, or maybe it was the full pink lips that drew the eye to her perfect white teeth. Whichever one it was, I stared at her mouth a lot. It was the kind of mouth that always seemed to be pouting, but not in a bad way. More like in a kind of I-wonder-what-these-full-pouty-lips-would-feel-like way. But her mouth wasn’t even the best part of her. She had these full but perky breasts and wide round hips, and she drew attention to those by wearing really tight fitting jeans and tops. I mean so tight you really had to wonder how much time it took her to get into those in the morning. But anyway, I don’t mean to drone on about denims, you get the picture, the girl was hot.

Stephanie was Ringo’s girlfriend. Now I know you’re thinking Ringo’s the drummer, but in this band Ringo’s the lead singer. Why? Just because I happen to think that Ringo is a better name than John or Paul, that’s all. But never mind that. Now about Ringo: I quickly found out that Ringo was kind of an ass. First or all he showed up late. Everybody was waiting for him and even Stephanie didn’t know where he was. Second of all, he really enjoyed bossing people around. Like for instance when we got lost on the way there and Ringo kept yelling directions at the driver but of course he had no idea where he was actually going. Anyway. Ringo’s eighteen and he’s the singer of a band and he’s just got his first out-of-town gig and you can tell he thinks he’s a real frickin rock star.

Since I wasn’t part of the band or anything and my presence was kind of a last minute thing, I got stuck in the backseat of the minivan. Fortunately though, the band decided to also cram the two girls in there with me because all the guys in the band were pretty tall and didn’t want to wedge themselves back there. So even though my legs got pretty stiff the ride wasn’t that bad.

I already knew Stephanie a bit but only a bit and only because she was a friend of Anna’s. We had never really talked before. At first she was a bit standoffish and mostly looked out the window, but after a while she warmed up to me a bit and by the end of the drive we had a nice little thing going. She’s one of those girls who are always putting her hand on your arm when you’re talking to them, and while I’m not usually the type to do that to a girl i just met, in this case I figured I might as well just go with it. So we chatted about her hometown and about school and things like that, and all the while she either had her hand on my thigh or I had mine on hers. That was kind of nice. Besides, in my I’m-not-so-sure-I’m-over-her state, it felt kind of good to have these small PDAs in front of Anna, even if it was just a way to show her (and well, probably show myself too) that I wasn’t pining after her or anything and I really was over her. Of course I talked to Anna too on that drive, but she was pretty aloof towards me. We were still friends and all, but she sure didn’t want me to put a hand on her leg. I wasn’t too sure what to make of that, but that’s Anna for you: real friendly one day and acting like I’m not even there the next.

Because of our late departure and Ringo’s manly sense of not asking for directions, we got to the club a bit late and the band immediately set to getting their equipment plugged in. I called the place a club but it was more like a bar really, if for you a club and a bar are different things. It was small and it had the actual bar on one side of the room and the stage on another and maybe about twenty tables in the middle. I had nothing to do and the band didn’t really want my help so I just sat down at the bar by myself and tried not to get too bored for a while.

And here I’m going to go all ninja and just go over the events of that night really quick because otherwise this is going to clock in at well over 5,000 words and I know nobody’s got the time for that. So bullet one, I’m not American. I put that little side note in there because otherwise you’re probably wondering what eighteen-year-olds are doing drinking in a bar. Where I’m from that’s legal. Bullet two, I’m usually pretty reserved but for some reason whenever I’m out of town it seems I always become Johnny Outgoing or something, and on this particular night I really hit it off with the bartender. She was this twenty-two-year old Polish girl with a thick accent and she kept asking me if the band played any loaf songs. Stupid me thought she meant songs by Meat Loaf and for the life of me I couldn’t figure why she’d want to hear that (not to diss Mr. Loaf or anything, I have two of his albums myself) but finally my French lined up with her Polish and I realized she meant love. Anyway, probably sounds kind of stupid saying like that but we kind of bonded over that little awkward conversation and we chatted all through the night. I guess I could have written her out somehow, but she’ll appear again a little later so I figured I should introduce her so she doesn’t come out of left field. And finally, bullet number three, Stephanie. Now she and I we really hit if off. We spent a good four hours sitting next to each other at that bar and she laughed at all my crappy jokes and her hands kept finding excuses to touch my arm and my thigh. Heck, she even tried to tickle me at some point. Almost spilled my beer. My new best bud the barkeep thought we were kind of cute the two of us crazy French kids and she slipped us a few drinks and that just seemed to put Stephanie in a pretty good mood. I was feeling pretty good about my decision to ditch Buffy right about then.

Now the band though, their night kind of sucked. The bar was only half full and clearly no one was there to hear the live entertainment. And they kept messing up songs and you could tell that Ringo was getting pretty pissed. The poor guy probably had visions of groupies dancing in his head and all he got was a handful of drunken frat boys and some dick coming on to this girlfriend. If he wasn’t such an ass I’d almost feel bad for him. But anyway, by the end of the night everybody had had quite enough so we all headed to the hotel room. Now that’s right, the hotel room. One. Uno. For seven people. The band must be pretty poor. Either that or they’re all cheap bastards. Yeah, probably the latter. And as an outsider, I was one of the lucky ones who got to sleep on the floor. I really can’t sleep on a hard floor so I barely slept all night. The next morning I got up early and knowing that another night like that would probably kill me (what can I say I’m a delicate flower) first thing I did was go book another room for myself. Don’t tell those cheap bastards but I’m not so poor that I can’t afford a hotel room for one night.

Anna and I spent that afternoon together, walking around, stopping at record stores, drinking coffee, that kind of stuff. She was being friendly but she really wasn’t flirty and when I tried it didn’t click so I figured whatever we had the month before was definitely gone now. Again, I said no mushy stuff, so I’ll just casually mention that my dick wasn’t too happy about that, truth be told, but I felt confident it could get hard again one day. My dick hurt but it wasn’t broken is what I’m trying to say. Anyway. We still had a nice afternoon and after dinner we headed to the bar.

Ringo was late again and the band was late getting on stage but tonight’s handful of net-yet-drunk-but-already-pretty-primed frat boys didn’t seem to mind. Stephanie was nowhere to be found so I sat there and chatted with my new Polish bartender BFF. She told me about Polish music and she talked to me about loaf. I was sipping my beer and just listening to her when Stephanie finally showed up.

She sat down next to me and asked me to buy her a shot. At first I figured sure no problem this is just like last night but when I saw how quickly she downed it I kind of wondered if there was something wrong. She asked me to buy another one and well, I couldn’t really say no could I? So she puts an arm around my shoulder and our friend the bartender refills her glass and smiles at us. “You two make such a cute couple” Apparently she didn’t get the memo. But anyway that gets Stephanie going and she kisses me on the cheek. I’m too surprised and shocked to do anything before she leans in again, and really kisses me this time. And with her nice perky boobs pressed tightly against me, whispers “Do you want to go back to your room?” And my first reaction is “What about Ringo?” But then she tells me “Oh, Ringo and I just broke up. He slept with another girl.” And I just stutter something unintelligible so she gets up and says “I have to use the restroom. I’ll be back in two minutes. You just think about that.” And the bartender who’s heard everything looks at me and she’s got this big goofy smile from ear to ear.

I do my best to get her caught up with the situation in thirty seconds. Am I a jerk to want to have sex with Stephanie? Isn’t that taking advantage of a poor girl who’s obviously emotionally distressed.“Listen, she says, if anybody’s being taken advantage of here, it’s you.” Well, if you put it like that… I really don’t mind being taken advantage of.

So Stephanie and I head back to my room. We’re barely inside when she starts kissing me again. Her full pouty lips are on mine and her hands are in my hair and she’s tugging at my clothes. I take my shirt off and she pushes me to the bed and she starts to strip. I’ve never been with a girl that was that aggressive before (no shit, the only girl I’ve been with before was still a virgin) I’m not sure if I’m supposed to try to take over or let her be in charge. But she doesn’t give me much say in the matter.

Before I know it she’s completely naked. Her tits are glorious. If Anna was a barely-there A cup she’s a full C at least, firm and tight with hard nipples pointing straight ahead. Her hips look just as good naked as they did with those tight jeans on (oh and by the way, I still don’t know how long those take to put on, but they were off in two seconds flat) She’s not tall and her legs are kind of short, but at this point I’m mostly staring at what’s between them anyway. She’s shaved and I can see her inner lips just peeking out, pink and soft and oh so inviting.

I pull my pants off and before I know it she’s on top of me and my cock’s in her mouth. I’d had a handjob before but this is my first blowjob and she knows what she’s doing and man, it feels pretty frickin good. She’s slobbering all over it and her head’s just bobbing up and down like she’s on a mission and in no time at all I’m hard as a rock. But this ain’t about me or my own pleasure and she’s got me where she wanted so she doesn’t waste any more time and she slips a rubber over me and she sits on top of me and she slides me inside her.

And oh my god… She’s grinding her hips with a purpose and she’s fucking me furiously and her tits are just bouncing up and down and all I can hear is this loud smack-smack-smack sound each time she slams back down into me. Her eyes are closed and she’s biting her bottom lip and her hands are on my chest and at this rate I know I’m going to come in less than a New York minute. She can probably feel it and she opens her eyes and she leans into me a bit and she just stares at me and says “Don’t you DARE come before I do.” And she keeps fucking me hard repeating it every once in a while like a fucking mantra “Don’t come. Don’t come. Don’t come.” But of course the sound of her voice like that and the sight of her bent over me like that is just making me even closer. So I close my eyes and think of all the most unsexy shit that I can. My ninety-year-old grandmother--yeah, she’s not having sex right now. Those starving children in Africa in those give-us-money ads on TV. Not fucking sexy at all. Anyway, all kinds of crazy shit like that.

And finally, FINALLY, she comes. And she’s not shy about being loud at all and she doesn’t try to keep it in whatsoever. She just MOANS like this is the most god-awesome orgasm she’s ever had and she shivers and shakes and trembles and twitches. And when I hear that and I see that and I feel her shaking on top of me I finally come too. And I’ve been trying to hold it in so long it feels like my balls are getting ripped out by the root and pulled out of my cock. But in a good way. Like every drop of cum gets sucked out of me and comes streaming out of my cock.

And after all that there isn’t much talk. I’m exhausted and it’s late and we lie down and before I know it I’m snoozing off.

I’m woken up by a knock at the door. I don’t know what time it is but it’s dark and Stephanie is sleeping next to me. I grab one of those hotel bathrobe from the bathroom and I open the door. It’s Anna.

She asks me if Stephanie’s with me. I hesitate a bit but I figure the band is probably looking for her so I say yes. And I thought that would be that but no, Anna asks me if she can come in. I see no reason why not so I say sure and I close the door behind her. The bathroom light is on but the room is small and there’s no couch or anything and Stephanie’s on the bed so we sit down on the floor with our backs against the bed and we whisper so as not to wake her up.

We talk a bit. She asks me if I knew that Ringo and Stephanie had broken up that afternoon. I say yes, she told me. Then she asks me if I knew why. I say she told me Ringo was cheating on her. Then she hesitates a bit, but she continues. Do I know who Ringo cheated on her with? No, she didn’t tell me that part. She hesitates a bit more. With me.

Holy fuck. My dick took that harder than I thought it would. Especially considering what just happened with Stephanie. But apparently my dick still had a thing for Anna. And I’m kind of looking for something to say and I know I shouldn’t say that but I say it anyway. When? And the answer really knocks my dick off. That Saturday night, the night after we were together.

Well technically she could have said it was the night of the morning when we were together, but at that moment I wasn’t going to argue semantics with her. She tells me that’s why Stephanie had come on the trip, to kind of keep an eye on Ringo and Anna. I ask her how did Steph find out about it and she tells me she told her. She was her friend after all and she felt bad and she only had sex with Ringo that one night. I don’t know why exactly, I kind of had enough information to process already.

So yeah, I promised no matters of the heart, but my dick was confused as fuck at that particular point. On the one hand it felt like crawling back inside my body and sleeping there for a while. Say a hundred years or two. But on the other hand this was still Anna. Does it really matter what one of us had done one time one night with one guy? It’s not like we were dating after all. And I’m sitting there quietly wondering if I can forgive her, but really, what’s there to forgive? Yeah she crushed my dick, but it was all done by the rules, right? And besides, didn’t I just do that same thing with Stephanie? Anyway I don’t see it as I had any real choice about the whole thing. So of course I forgive her. And we’re sitting there side by side in the dark and I smile at her and she smiles at me and we lean in and we kiss.

I’m still not sure why she kissed me that night. I mean I know why I kissed her, but I’d have kissed her the night before that and the night before that and the night before that. But why was it that night for her I don’t know. And again, no matters of the heart so I’ll spare you what was going through my head at that particular moment, but my hand reached for her breast and she didn’t stop me. And my hand got under her shirt and she kissed me more. And my hands unbuttoned her jeans and she got up to take them off.

After the previous night I kind of had this thing about hard floors so we got in the bed. Stephanie was still sleeping so we had to be very quiet. Lips pressed against each others and hands roamed over bodies and fingers teased and pinched hardened nipples and we muffled our moans with our kissing. She was lying on her back with her legs spread apart with me between them and my cock got really hard really fast. She was wet and dripping and our breath quick already and her hand reached down and guided me inside her and I locked my arms on each side of her and I started pushing in long slow strokes.

In this position my shoulders and head are about a couple of feet above her so I can really see all of her. Her soft white skin with just a hint of goosebumps. The small mounds of her tits with the erect nipples stiff atop them. Her small and narrow waist. The fuzz of her other mound just below with my cock sliding in and out of her. Her closed eyes and her slightly flaring nostrils and her mouth agape that closes slightly each time I thrust in.

We fuck like that long and slow so as not to wake up Stephanie. The bed’s gently rocking under us but Stephanie’s far enough away and she doesn’t notice. And for a long time I can feel myself just sitting on the edge so I slow it down even more. Thrust in, pause, pull out. Thrust in, pause, pull out. And she shivers each time I pull out and she whimpers each time I trust in. She’s got her hand between her legs and soon I can feel she’s getting closer too. But I don’t want it to end just yet, so I grab her hands and pin them over her head. My cock’s still swelling inside her as if that’s even possible and I’ve got my whole weight on top of her and her tiny tits press against me and we kiss and we kiss and we kiss.

And when we’ve had our fill I let go of her hands and I pick up the speed again and I know this time there’s no stopping it. Thank god I already had sex that night so even though I can feel I’m almost there we still fuck for a good long while. We fuck and we fuck and now the bed’s really rocking and there’s no muffling any of the sounds now coming out of us and really it’s a miracle but Stephanie’s still sleeping over there swaying up and down.

And I can feel Anna’s pussy tightening more and more around my cock and finally she comes, her body gently shivering under mine and her lips pressed tight so as not to make a sound. And I then I come too, surprisingly hard, and my cock throbs and empties gush after gush inside her. I gasped, shocked by force of it all, amazed by how much cum Anna milked out of me.

We slept together that night, me and Anna and Stephanie in that hotel room bed. As I said earlier, Stephanie and Anna were friends, and Stephanie didn’t seem surprised or upset to find Anna in the bed with us in the morning. From what I gathered this wasn’t the first time they’d woken up in the same bed. The rest of the band wasn’t so understanding though, particularly Ringo. The drive home was spent mostly in silence and they dumped me rather unceremoniously at the first subway station we found after getting off the highway.

Anna and I dated for a short while, but it very quickly became clear it wouldn’t work out between us. She still wanted to go out seven nights a week and see all of her old friends, and I’m more of a homebody and I find that much social interaction too draining. I went out with her and her friends a few times but that just ended up in a lot of awkward conversation. It just wasn’t my thing.

As for Stephanie, I didn’t see much of her after that. We’re still Facebook friends though, and I learned later that Ringo had actually cheated on her not just with Anna, but with other girls as well. Apparently they had a big fight about it that day and that’s why she came after me that night. So the problems between her and Ringo weren’t really about Anna after all.

Anyway, sorry the story’s so long. I actually cut a lot of stuff out to try and make the length more reasonable. Hopefully I didn’t butcher it too much. So long.