Nude Training

Well, what do I want to do? I want to take her to bed of course. I'm a red blooded male, fucking's usually on the top of my wish list. And you know we've fucked before, in less one on one ways than this but there shouldn't be any awkwardness regarding copulation between us.

"Want to go upstairs?" I ask. Hopefully she knows what that's a euphemism for.

"Sure," she replies. I note the difference between this sure and a straightforward yes. A yes in this case means she wants to take a course of action that results in me drilling her g-spot. The sure she spat out means she's fine with me drilling her g-spot but she's not set on it, it's just an option she could take.

Well affirmation is affirmation, and this affirmation means I'm going to get lucky. I mean... Fuck what am I saying? I don't want my thought process to lead me through this kind of talk, it's just... Fuck. Sex is weird. Don't get me wrong, sex is awesome but it's also strange weird, discomforting and scary.

It's a lot of thing, and one thing it isn't is confidence boosting. Lots can go wrong, check out the wiki page for people who have died during sex. Spoiler alert: Matthew McConaughey's dad's on it. I mean no way I'm dying at this ripe an age unless I hit my head in a weird way. I guess I kind of bring a coarse attitude with me to distract from the fear. Doesn't always make me the best person, at least in my own head

I digress. Man I digress really fucking hard. Anxiety will do that to you. All this time you could've been hearing tales of sexual congress with a beautiful lady. Instead you now have a detailed description of my fears. Angst does not lead you down the right road.

Luckily thoughts come quickly and none of them have led to actions. We've only just reached my room as I pull the breaks on this runaway thought train. Now a few final thoughts as it screeches to a halt: I like sex. It's fun, plain and simple. I often feel like a bad person for wanting it, guess the puritan backbone of our country has not become vestigial yet.

But I look at Lucy sitting down next to me on the bed. I think we both want this, sures notwithstanding. So I got to decide, do I want to bring anxiety to this or do I want to bring calm?

I choose calm, or at least hope for it, as I put both of my hands on her and slowly push her down. Not doing the kissing thing yet, just going on top of her and lifting up her shirt. She acquiesces.

Flashforward and we've both done our undressing. It kind of feels more normal to be naked in this situation than to be clothed given everything we've done up until now. Anyway I lower myself down to get her ready with my tongue. Not sure I'm going to go for the orgasm with tongue thing, sis ain't around to impart her aura of sexual tenacity.

I guess my motivation for pleasuring women is a little fair weather. All I want to do is get her to the point where me and I can fuck. You know her moans sound good but a little bit of the anxiety is creeping back in. I want something to hang my head around and fucking's a little less abstract than trying to pleasure a girl I can't completely tell how she's feeling.

So do my tongue action, don't even get around to asking her if she wants anything other than circles this time either. No, I get her wet enough and go straight to the finish line.

Get back on top of her, dick fuck ready hard. So I push in. It feels good but this ain't reaching the sexual highs as the previous times. After all that internal conflict I subjected to you all, I wish I had a better outcome. I Thought I had wrestled with my demons but they were just biding their time. Score one for anxiety.

I push back out and back in. Out and in, over and over again. That's the way that sex works. And this works all right, it's just not spectacular. Ah well, sex is usually on the right side of good and this is no exception. Her insides feel good, wet and soft, all that a guy could ask for. It's just I'm not doing all that I could ask for.

Try to make this quick. I increase my pace if only for the thought that increased traction would speed this up quickly. Try to remember the more hotter times with my sis to get the brain working for me on this one.

I look at her face. At least I can tell she's not feeling pain. Don't think I'm properly doing her sensory nerves a service, she still has that studious look on her face. Is she judging my shortcomings. Nah, at least not in a judgmental way. She doesn't strike me as the person who carries around negative thoughts on others to make herself feel better, she's just interested in the world. Or at least sex. If there's any negativity there it's just out of a desire for objectivity and the need to divide things into pros and cons.

Anyway I give up the ghost finally and cum. Hopefully there will be other better sexual encounters detailed in the coming pages that will get you off better. But for now, you got this quasi failure to keep you so close but not quite there.

So load's shot and I roll over off of her. We both do our breathing. I don't know what to say to her. Should I apologize? No, don't think I was quite that bad. It's just that I could be better and I have been better. I want to address that if only to have someone to bounce my own ideas of why it didn't reach those highs off of.

"Not sure exactly why that wasn't as good as before," I finally say. Pretty sure that's not how you want to lead off the denouement of a sexual encounter but that's all I can think of to say.

"I have some thoughts," she replies. "For one your sis isn't here. She brings out... No she demands the best out of you. And me for that matter."

"Figured as much," I say sighing. "Guess I'm not as much without her."

"Don't be so hard on yourself. You're still learning. You'll get there."

"And you're good to experience my weak willed fucking while I get there? Cause I know my sister isn't. Well I mean she did, but only as an example. And that was her fucking me, not the other way around."

"I'm good. Even when you get ready again. There were things to enjoy about it."

"Don't you think you deserve more though?"

"It's not about deserve, it's about interest. And I'm interested in having sex with you."

"Why?"

"Because I want to experience your change. I want to be able to compare before and after."

"Why?"

"Because I want my own change, but I don't know exactly what. So I want to absorb the changes of those around me and learn from their journey."

Not an especially romantic sentiment, but it'll do. Heck I don't have the most romantic overtures in this situation either.

"I like you, I really do. I'm not sure how I could not like someone who is willing to do this for me. But I don't want my sexual prowess to come from my affection for you. I want it to be a bit more inherent in me."

"I know."

"You do? How?"

"Your sister." Good answer, explained a lot in two words.

"She's a good teacher isn't she."

"Well she figured out how to learn things like this quickly, innately even. Might as well impart her lesson to others."

"I wish my sex skills weren't so dependent on the situation. I wish I could fuck you like I did before but with my sister not necessarily being present."

"Listen to her and you'll get there."

"And is this a part of the plan that she's laid out for me?"

"It is, there's a reason why I'm alone with you."

"I guess I'll trust that reason's a good one."

"You won't be disappointed."

Then I decide to see if I could get my own piece of the background between her and my sis. "So how did this whole thing start between you and Tiffany?"

She sighs before saying "In College one day, she told me she wanted to get more comfortable with her body and was wondering if I wouldn't mind if she went naked from time to time in front of me. Wanting to support her, I agreed. Pretty soon she's naked more often than not.

Eventually my desire to shield my eyes away lessened and her nudity became commonplace. I kind of started envying her comfort with her body and asked if I could join her. She was more than welcoming, then our dorm room became its own tiny nudist colony.

So we're doing lots of things naked. Studying naked, smoking weed naked and going to sleep naked. It was during one of these nights when your sis asked me if it was ok if she masturbated. She told me she had been sometimes masturbating discreetly at night and wondered if she could just skip the discreet part and go all out in the masturbating. I had been doing a similar thing, we had both seen much of our bodies and also it seemed like it would be refreshing to masturbate without fear of judgement. It also seemed silly to stop the acceptance here so why not break a few more barriers while we're at it.

So we jilled off in front of each other. I thought it would be much weirder than it was. We all masturbate, not a big deal if you don't think it is. But this whole masturbating out in the open awakened something in her, something you and me have yet to reach. She found power in the need to pleasure herself. All vulnerability had been shed, it was just her enjoying being able to show herself being pleasured.

I felt an attraction to this that to this day I'm not sure if I properly understand. I'm not sure it was sexual, I mean it definitely became sexual, but not sure if that's how it started. I just remember getting a little more closer to your sister. Being physically closer, wanting to know more about her.

She fucking knew. I didn't even really know, I was figuring out new ways to delude myself every day. But she saw past all the bullshit and knew what I wanted. So one day after a masturbation session she told me to come over to her bed. I complied without a second thought, a girl can do strange things after mutual masturbation.

So there I was on top of her blankets, sitting down next to her. We got the rippling stomach thing that often happens when you're sitting down, leaning over a little. Not men's magazine material but we didn't care. Two girls know better than to objectify ourselves like that.

After sitting there for a sec, just enjoying each other's company in silence, which isn't hard to do when you've both just harvested your love juice, she started increasing body contact. First it was just hands on my arm then it was thighs touching completely. First step toward breaking down my physical boundaries.

Then she flashed her smile. Don't know why the common cliché is that hypnotists focus on the eyes when those pearly gates can do so much damage. I was transfixed, fuck that smile carries so much power.

Fuck, I was all worked up on that smile, when the truth was that it doesn't even come close to matching how powerful the rest of her is. She carried her body in stride, she still does, while even though we'd been naked together so much I lost count, I still had some shyness and nerves rattling around in my brain.

Anyways, I got lost in my thoughts on your sis, sad to say that this is a common occurrence. So down to action. We're both eye looking and she's smiling and she says to me 'you don't want just a kiss, do you?' Can't even fathom what's going on in my mind, sometimes you just let your desires take control, but I nod, I fucking nodded.

She says to me 'you want something a little more... visceral.' Right on the dollar, the nodding continues. 'luckily for you, I got just the thing.' So she moves to the side of her bed and pulls out that strap on you've seen in action. Let me tell you it feels even better than it looks. Don't know if your ass works anywhere near how my vagina does but if it does, I'd recommend it.

Well then she fits herself on it, gets the straps just right and pushes me down. No kiss all right, instead we're going straight into fucking. She skips all three bases and heads straight to home. I don't want to give you the wrong idea, she wasn't in any rush but neither was she pussyfooting around my pussy.

She eases herself in, my orgasm helped me with the warm up on this. I realized that she must've been planning this for a bit. Great plan it was though, don't got anything negative to say about it.

Let me tell you, this fucking wasn't about technique at all. I got to say she's upped her game tremendously from when we first started. But fuck did she bring the commitment. Don't know how hard it is to use a cock, much less a prosthetic one, but she wasn't letting failure keep her back. Failure was just something to learn from and boy was she learning, with every stroke she got better. She was intent on riding that learning curve all the way to learning.

So it took her awhile to do the thrusting completely right, but that didn't matter. What mattered is her. Her pushing me down, her holding my hands while we do it, her starring into my eyes, her bending the aura around her to suit her needs, her just being her. That's what maybe makes it my favorite sexual encounter, I got to experience her like that for the first time. She knew what she wanted, she knew what I wanted, and she found that Venn diagram overlap just right.

I didn't even know exactly what I wanted, part of me is still figuring it out, but she knew that at least part of me wanted awe and awe is what she delivered. Though like I said her skill might have not been all there she had found her intent all right. And her intent flowed through onto me.

Don't know if a piece of silicone should feel as good as a dick, but it didn't matter. What mattered was she made me her bitch in the best possible way. I'm supposed to be Ms. Shy Gal, but she got it to the point where Ms. Shy Gal was getting lesbian fucked all the way up the Kinsey scale.

That's what I remember, that feeling of a bunch of my barriers being shattered. And the ones that were left were definitely up for negotiation. She gave me freedom, and in return I gave her the awe she deserved. As she slid that wonderful man made dick in and out of me, getting better with each thrust, I just marveled at the power she had to take me to that place.

Sexual pleasure was beside the point, even though sexual pleasure was all we were doing. She was creating an emotional connection without creating one. She was just doing her thing, the emotions were as one sided as fuck. Still I didn't mind, who fucking needs love when you got your sister in your pussy.

If this all sounds inscrutable to you, well, it's cause look at what I'm trying to describe. I'm trying to describe your sister's effect on me. There's no clear picture, just a bunch of sideways and alleys my mind can get lost down. Theories and guesses, never a satisfactory explanation. She's just a mystery that I've loved being in.

That's why I want to fuck you. I just want to know how your sister got from point A to point here. She came to it quicker than you so far, but you two have the same potential. She knew it, that's why she asked me to do some naked sunbathing with her. She wanted to draw you out into the open.

So I want to experience her transformation through you. That way I can understand her and get to know her better. You know I like being her bitch and the mystery of it all is fun, but maybe someday I want her to be my bitch. Or maybe I want us to fuck as equals. I want more potential for our relationship, I think you can help me get there."

"Well that story gave me a little... Potential. Care to try it out?" I ask.

"Let's get to learning," she says enthusiastically.

We learn all right.

****************************************************

I feel the cool air of the night against my body. What's going on? Who's there?

All of my questions are answered when I see my equally naked sister standing over me with my blanket in her hand.

"Starting to sleep naked huh? That's good," she says to me.

Guess I got all those questions answered now. The only one left is where does this fit into her plan.

"You spent the day fucking Lucy right?"

"More or less," I reply.

"Good to know, you're good on the fucking right? All fucked out?"

"Well you know I could always have another go if necessary."

"That's not happening, at least not tonight. There's a more important lesson to be learned now."

I don't argue, I figure she's got a reason for doing what she's doing. "Ok, what's the lesson?"

"It's affection, pure and simple. Lots of people think you should show affection before any sexual conduct. They're wrong. That's how affection becomes corrupted and turns into a manipulation to gain sex. With you having had sex today and having no hope of it with me it's pointless to use it in such a manner. So now you will learn to use affection as tool to benefit both parties."

I got no qualms with that. "All right, teach me how to do that."

"First get up and stand before me," she commands.

Done and done. No reason to approach this without the utmost comfort. She's seen me naked before and hasn't shown a hint of judgement. Plus I'm kind of sleepy so my sense of shame is at low capacity. Guess shame isn't that high priority then.

"Now embrace me. But before doing so, think of the energy that you would like to bring. How do you feel about me? How would you like to feel about me? If you could show me any emotion, what would it be?" She enquired.

Gratitude and respect. I guess those are two emotions, not one, but I think I'll manage. So I go over and give her the best hug I can while keeping those two feelings in my mind. At least I try to, the thing that's poking her in her leg seems to have other ideas.

"Sorry about that," I tell her.

"It's not going to be a problem unless you make it a problem. Just ignore it, you've fucked enough today that you don't need to take care of it. Instead focus on me and how you feel about me."

I do. It's easier when my sis tells me to do something than when I try to do it myself. Her authority beats my self control. Don't see anything wrong with that though.

So I continue wrapping my arms against her, and she ever so slightly reciprocates the action. Not enough to take the focus of me physically expressing myself before her. I know she doesn't need my affection but I'm going to do my best to make sure she appreciates it.

I hold her, I try and will my arms to transfer what I can to her. Don't want to vocalize it, just want to convey it. I close my eyes, focus on gratitude and respect, maybe throw in a bit of admiration while I'm at it. Couldn't hurt, Right?

I notice for the first time that her bare breasts are digging into me. For once I don't feel sexually attracted to the thought. It's not her breasts that are sexy, it is her herself that is sexy. Any flesh could not compare to the essence that is stirring around in her. For once I was glad to ignore her breasts.

I feel something pulsing through her. It could just be my mind but I think I got my idea across. I keep hold of her for a few moments longer, just to be sure and also because I like the feel, and then let go. "Did you like that?" I ask.

"You shouldn't be so concerned what I think. The point is that you showed me genuine warmth with that hug. But yes, I did," she replied.

Good to know, even if it's just for ego reasons. I smile, seeing if I can crack one out of her. I do. Guess I have more influence than I thought. But for now let's put that information in my back pocket while we see what other lessons my sister may have in store.

"So what's next on the docket?" I ask.

"Kiss me."

I never did the whole pre-teen dating thing where kissing was as far as you'd go. I kind of got into dating later in my teens when sex was on the table. So I've never really treated kissing as a big deal. That's about to change though.

So how to kiss her? Don't think my whole being there with my lips parted while she does all the work act is going to cut it this time around. How do you bring passion to something like this without making a total fool of yourself?