Where should we go?

A friend's brother and another girl came to town late one Friday night. I thought they were dating, but on Saturday I learned that they weren't. I wasn't immediately attracted to the kid but the more he talked the more I became interested. Still, strange ground to try and discover when he's related to a pretty good friend.

A group of us were hanging out, and one by one everyone crashed but the two of us. We went outside to talk so he could smoke and our voices wouldn't bother anyone. We talked about everything, but as most conversations go, eventually it turned to relationships and sex.  I gave him my standard diatribe on how I eschew the ideals of the traditional relationship, which I have realized is basically the intellectual version of saying I'm DTF.

We were sitting rather close, and I can't remember who kissed who first but quickly we realized we needed to fuck but weren't quite sure where to go.  My place was a bit of a walk, the back of our friend's truck was considered but I feared it would be too noisy.  He grabbed my hand and led me around the back of the apartment building, to the side that faced the woods.  I knew that our friend's windows may be open and that they could hear, so I tried to be quiet as I got down on my knees to take him in my mouth.  I didn't get much chance to pleasure him this way as he pulled me back up, kissed me roughly and yanked off my pants.

I was a Girl Scout once, so I was prepared...I had a condom in my pocket that I handed him.  He put it on quickly, then pressed me face first into the brick and came at me from behind.  I nearly bloodied my lip as I bit it to keep from screaming out loud as he entered me forcefully.  It was exactly what I needed.

We are about the same height, so for him to penetrate me fully, we would need a different angle.  I pushed back into him and leaned over farther, grabbing my calves and pushing my ass out.  I was just the right way to get him to hit the spots I needed to cum hard.  He pounded me and came rather quickly but I was still able to cum with him.

We redressed and went back to the porch, and not long after the friend he had come to town with woke up and started talking to us, even asking him why his fly was down.  I was pretty sure she had a crush on him so I found the entire situation hilarious because I was pretty sure there was no way she could have known that we just went at it.  Also, I never told my friend that I had fucked her brother.  She probably wouldn't have cared but I'm pretty sure he would have been weird about it, and why would I want to create an awkward, unnecessary situation?

Memorial Day Weekend

After hours with friends at SM's place. I ask if I should stay or go, he says stay. We go to bed soon after that. He strips naked before going to bed but I only take off my pants. We immediately embrace. He says "if I'm teasing you too much you don't have to do this." It had been a few weeks since I had been here...I wasn't really thinking about sex, I just wanted a hug. "This is all I've wanted to do for two weeks, just hold you." He hugs me tighter. "Sex...is just icing." He pulls back a bit, looks me in the eye, and then kisses me deeply. "But sometimes it's just nice to do that." "Indeed." We realize that me still wearing a shirt is awkward, so it's removed. We continue to kiss and eventually I feel his fingers slide under my panties and inside of me, feeling my wetness.  He finds the right spot inside and sends me over the edge.  I'm compelled to keep relatively quiet and instead grab him tightly.  He kisses me as I come down from ecstasy. I explain that there are 2 different types of girls, those that build up to one orgasm that may or may not come, and girls like me that can keep on orgasming forever if allowed.  I think this was my subtle hint that I could have cum a few more times but I could tell that he was tired. We change our embrace naturally and settle in for sleep.  I commented on how with some people I toss and turn but I like that he and I fit together. We pass out and the next morning I give him a back rub and we get lunch together.

*****

As I was hanging out with friends, SM calls says he's having after hours.  I meet new some new people, and we stand on porch and chat for a long time. They leave, then SM and I listen to music. The Pixies, then the Mountain Goats, then Do Make Say Think. I love singing along to the Mountain Goats with him, it's a moment. In the middle, he asks "Why do I feel uncomfortable right now?" "Are you cold?" He wasn't wearing a shirt and we had just been outside to smoke. Shakes his head. "I shouldn't feel uncomfortable around you..." I say that I'm sorry I make him feel that way, it's not my intention. "And once again I'm hammered and you're not." "I'm used to it, don't worry about it." He says he needs to go to bed soon as it was almost 5am.

He again strips naked for sleep, I leave my panties and tshirt on. We embrace, his leg between mine, my leg over his hip. "I feel like all I do is tease you." This was sort of true but I never believed it to be intentional. "Nah, what makes you say that?" "Because i'm always too drunk to do anything". "I don't expect anything when I come over here. I just like to spend time with you." This was the truth.  He grabs me and holds me so tight.  I was happy to be on the same page with him, and expected to fall asleep in that exact position.

He goes in for the most intense kiss out of nowhere, and I'm taken aback for a second and apparently don't seem as into it as he would like. "Don't hold back." In between attacking him with kisses, I explain: "I'm not...I just never know what you want...you're really hard to read...you said you wanted to go to bed...so I believed you". I was practically on top of him at this point. He starts scratching my back intently, his thigh wedged between my legs, his mouth on my throat. I pull away long enough to remove my shirt. Simultaneously he pulls off my panties. I pull him on top of me. He sort of missed when he came in for the kiss, and I adjust a little under him and admit "You may or may not have just licked my eyeball. That was pretty funny." We both laugh hysterically and he rolls off me for a moment.  He mentions "I'm so glad we can laugh about these things."  "I think we have fun, right?" I ask. "Hell yeah we do." "And that's what it's about."

Somehow we went from laughing to him pinning my hands above my head, kissing down my body, until his fingers began to explore me inside.  I was not quite wet and it hurt a little. I waited to see if my body would adjust but it didn't, so I advised "not so deep".  He listened, and pulled his fingers back a bit and found a spot that hadn't been hit in a long while, pressing deeply downwards. I begin having explosive, convulsive orgasms - if his fingers weren't inside me, I could probably be mistaken for having a seizure. Somehow he ended up on my side of the bed, and I was perpendicular to him. "I have you figured out. I stay shallow and then press when you squeeze my fingers." I had no idea there was a method to the madness but I loved every second.  I think my vagina squeezing him was involuntary which made it that more interesting.  He came up and let me taste myself on his lips. I get very comfortable after so many orgasms and him by my side.  After a moment I move back to where we had started - we had to find his pillow, it had somehow migrated in the craziness of my orgasms.

Coming down from my orgasm high, I sigh, "You're wonderful." His response?  "I'm a fucking asshole."  There is a really long pause. "I'm a fucking asshole who happens to like you." I smile. "I like you too."  I fell asleep happy.

When you lay off the whiskey...

...good things can happen.

Coming down from a trip, I find myself on an epic journey to after hours at SM's place. Everyone leaves around 4:30, and by 5, he was ready to go to bed. We climb in bed and immediately spoon. His arms surrounding me, he kisses my shoulder, a seemingly perfect end to a wonderfully eventful day. I expected it to be cold so I left my hoodie on, but it wasn't, so as soon as I took it off I was met with his lips on my neck and his hands on my tits. He had said that he needed to crash because he had a lot to do the next day.

He's been so unpredictable that I wasn't sure if this was a "let's make out a bit before we pass out" moment or something more, and then he started grabbing for my clothes. He really loves my tits...who could blame him?

"Do whatever you want to me." "Oh don't you worry about that." I kiss his smooth downward as I reach for his fly. I treat myself to a deliciously hard cock. I'm perpendicular to him, but turn myself around as he reaches between my legs. "Spank me." One hand comes crashing down on my ass as two fingers from his other hand explore me inside. I increase the speed of my mouth on his dick, moaning around it as he finds all the right spots in my cunt.

I climb on top of him and slowly lower myself on him, relishing the feeling.  I try to start a rhythm but can't quite get the right angle so I ask if we can switch places.  He agrees but is slow to do so, wanting to kiss my neck.  I lean down and suck his cock again, enjoy my taste on him.  In one fluid motion, he flips me on my back, bends my knees back and enters me forcefully, deeply, intensely, hitting places he hadn't   before.  I couldn't stop cumming, I never wanted him to stop but despite the lack of whiskey he still didn't orgasm.  

We pass out. My alarm went off at 12:30, as I thought he would need to get up but he doesn't, so we fell back asleep for an hour. I wake up and kiss his neck a little, he doesn't respond but is awake. He asks, "What time is it?"  I reach for my phone on his side of the bed and as i'm looking for it under the pile of clothes, he spanks my ass a few times since I'm leaned over him. "Almost 2".

I look back and can almost see the "that should be enough time" look on his face. He flips me over and kisses me deeply, passionately. I can feel him getting hard against my leg. As we kiss, he rolls onto his back and without hesitation, my mouth is surrounding his cock, giving it my best effort. He responds with thrusting motions and delicious sounds of pleasure. Sometimes he's so quiet I never know if I'm doing it right but this time it was obvious. "You sure do know how to do that, and I really appreciate it. I replace my mouth with my hands for a moment to respond. "Well, I have been doing it for... [I couldn't remember how many years]...a while now." I smile, flip my hair out of the way and go back to what I was doing. He guides me to turn around enough for him to finger my pussy again while I continue. When a guy is really into it I can keep sucking cock just as long as my jaw doesn't go numb. It makes me so wet, just thinking about his cock moving in and out of me. Makes me want it in my pussy or deep in my ass. I wonder what it would take to get him to fuck my ass? Hmm...

Anyway, I took a break and kissed him and immediately he's rolling into me and sliding his leg between mine. I had redonned my panties for sleeping purposes, so I reached down and pulled them out of the way so that my dripping cunt would rub against his thigh. The purpose being a cross between needing to be pushed over the edge and wanting to mark him with my cum. I came hard, shaking in his arms, clawing at his back, not caring about what sounds I made. I think this threw him into a frenzy...he threw me onto my back, pried my legs apart and just started fucking. I needed it so badly, to be fucked like that, hard, no pretense, no "Is this ok?", nothing gentle, just stiff cock pounding into me. I was so wet he slid out a few times but was not dismayed, just kept right on going. I couldn't stop screaming "YES! FUCK ME!" over and over again. After several orgasms, he shifted a bit and started a different spot that really got to me, and as a huge orgasm rushed over me my legs clasped around his back and I kept him from thrusting for a bit so I could grind my clit against his body. He seemed to be convulsing a bit too so I thought he came too, which would have been wonderful but no matter what we do he never does. He could see that I was satisfied so he got up and went to the bathroom, came back and started to get dressed for work. I wondered if any of his coworkers would be able to smell me on him.

What's happening?

After taking a hiatus from hooking up, SM and I delve back into bed after a rather strange dinner party. We 69, he eats my cunt like he forgot what it tasted like and wanted desperately to remember. He takes a break, starts talking about his issues with a mutual friend while still lounging between my legs. I'm confused, are we fucking or having a heart to heart? I call him out on it.

"Are we talking about that or are you gonna eat my pussy? I'm down with either but not at the same time." I turn back around, we both laugh at the ridiculousness of the situation and pass out.

In the morning, I wake up around 10 and try to wake him up with my mouth. He barely moves, so I go back to sleep for a bit. I try again in a few hours, he's more receptive to it this time. I knew he said that he didn't want to hook up anymore - I took it as though he respected me as a friend too much to be hooking up with me the same way he did random girls from the bar. But now we've gone back to it...I'm not sad about it. I concentrate on giving him the best blowjob possible, and he seemed to be really into it. At some point he stops me, flips me onto my back and starts to fuck me silly out of nowhere. This goes on for a few minutes and then he gets up and starts to get dressed. Smacks my ass and says, "This has been fun, but you've got to get the fuck out of here."

How rude. He did need to go to work, but that was the first time I was kicked out as opposed to us walking out together. I go to leave and he's standing in the doorway, smoking a cigarette in my way. "If you want me to 'get the fuck out of here', you've gotta get out of my way." He moves, I walk out without looking back.

Did he regret hooking up after making such a point not to? I have no idea but he did call me the very next night to come over.

A spanking lesson...

Randomly at the bar on a Sunday, and I run into SM of course.  The place is pretty dead but we get invited to hang out with some people we've met there.  Turns out I vaguely know the people whose house we end up at, and hung out til 4am, blasting various things on vinyl and generally being ridiculous.  Seeing as I have to work in the morning, I keep hoping that SM decides he's ready to leave at some point as clearly I want to go with him either to his place or mine.  I thought he went to the bathroom at one point, and when he doesn't return for quite some time, I go back to that part of the house to realize he's dipped out the back door and disappears.  Slightly angry, I say goodnight and start my trek home alone.

As I'm walking in my front door, I feel my pocket vibrating.  He's calling me to come over, and explains that his conversation with a guy at the party was pissing him off and that he needed to leave before the situation escalated.  I guess that was a smart move?  I agreed to come over only because I was still dressed and had my coat on and I had been waiting to hang out with him all night.  Had I already been in bed...I probably would have stayed there or told him to come to me.

We went straight to bed as soon as we got there considering the time and all. He begins to kiss me, intensely, and then lies back and says something a bit surprising. "Why don't you make a move?"  Usually he's all about making the moves, and seeing as I've always felt a little lucky to even know him let alone be in bed with him, I've always been happy to go with the flow of the situation.

I figure he said this for one of three reasons. a) He was tired and wanted me to "make moves" so to speak because he was took drunk and didn't have the energy.  b)  He actually wanted me to dominate him, at least in that moment.  c) This was code for "give me a blowjob".

At that moment, I didn't care what the reason was, I just wanted him. No thoughts, just went for his fly,  taking him in my mouth.  He was only semi-hard but I still enjoyed the feel of him there.

In retrospect, the answer to the above question was c), as it wasn't long before he insisted on reaching between my legs, turning me around, fingering me and burying his face into my cunt. 

Perhaps he had a hangnail or something because his fingering hurt at first but eventually became wet enough from his licking.  He's never had problems finding my g-spot but somehow the combination of his fingers ministrations and his mouth created a unique experience for a few moments. He was confused because he didn't seem to think he was doing anything new. I tried to explain via hand gestures but it was too dark to truly understand. I just didn't get why he stopped because whatever he was doing felt amazing.

He got up for a moment and returned to find me face down on the bed, still rather turned on. He laid on top of me for a moment (a feeling I love), then he gives my ass a playful smack and falls to the bed next to me. I tell him not to tease and lament that I no longer have someone that can seem to spank me properly.  He steps up to the plate, suddenly barraging my right ass cheek with all of his might. One of my hands moves to my cunt, my other grasping at whatever was around, blankets, pillows, his arms.

He lays closer to me, absorbing my energy, and continues his assault. I make sounds that if overheard could perhaps sound more abusive than pleasurable. I shifted away from him slightly, trying to get him to realize that my left ass cheek could also use the attention, and he took the hint. I begin to orgasm, simultaneously wanting him to pause so I could concentrate on cumming, and never wanting him to stop, to be able to bask in the pain/pleasure combination forever.  I was in another world...I'm not sure if he realized the effect he had on me in those moments. I lost track of how many times I came. I eventually rolled over and pulled him close. I needed to be tangled in him after such an experience.

He asked what that does for me and I had trouble explaining...I was still pumped full of adrenaline and it's not easy to describe how pain can transform into pleasure in the right situation. I invited him to see how wet it makes me and he seemed amazed. I passed out soon after, very pleased.

When we woke up, my ass was still a bit sore...I looked forward to seeing if he'd left any marks.