Hugo

I've just turned thirty and, not normally being one for reminiscing, it takes a few drinks with my girlfriends to get me thinking as we chat about how I'm the last one of our group to survive my 20s, and all the things I will not miss. Top on the list are 20 something boys. Not men, but boys. How we put up with so much of their shit because of all the weak ass emo love songs we grew up on (to name only one area of blame). Walking back to my apartment post revelry with a head full of bubbles and a belly full of edibles I think about my last orgasm and am instantly disappointed with boys once more. I have been the master of my pleasure for far too long while leaving a trail of twitching-from-release-post-orgasm boys in my wake over the years. They worked towards their ends and we helped them along without even a reach around -- as they like to call it -- for us women. How tragic boys know absolutely nothing of the female body apart from the fact they know they like tits and we have a few holes. If it wasn't so sad it'd be hilarious. Boys. Fuck em. Well -- not anymore.

Getting to my bedroom I whip off my dress and immediately pull on pajama pants while simultaneously throwing my bra as far away from me as possible. If I didn't have one outrageously prude friend who complains each time she notices I don't wear a bra I'd have never have strapped that awful device on. The lengths we go to not have to hear about other people's hang ups -- even at our own parties. Feeling wonderfully free I twirl about my room for a bit to some Saves the Day (what can I say, old habits) before noticing my bra has landed on my laptop and it's still on. Facebook is open and I have a few messages wishing me a happy one. Friends don't let friends Facebook drunk but unfortunately I live alone so, tragically, no one is here to intervene.

Scrolling through my feed I'm stopped in my tracks by a photo a friend of mine liked -- in it is my first real crush, the boy who sparked my sexual curiosity. His name is Hugo, he was my brother's best friend. A beautiful jewish man with dark, ebony hair, a swarthy complexion, the most lovely doe eyes, and a smile that made you truly, truly weak at the knees. I mean it. I never knew lips were meant for anything but talking before I saw his and immediately I understood his could be useful for other purposes, though my younger mind had no idea exactly what -- until one afternoon. So perfectly shaped and pillow-like are they that just to see them again I was fixated, eager to know what they'd feel like pressed up against mine, or all of me. Of course I click the photo and find his name tagged, leading me onto his page. I haven't spoken to him in over a decade. My brother and him had been best friends since high school, and I have a feeling I'm part of the reason they drifted apart. I'm still a bit sorry for it, though for my own selfish reasons.

So here I am, a freshly minted thirty year old looking at his Facebook page, a bit (ok a lot a bit) drunk and definitely stoned, at 3 a.m., and he still looks every bit as irresistible as I last remember him. Even more so, actually. Liquid courage takes hold and by the next morning I see the jumbled message I sent him and want to die. In short it read about how sorry I was when he and my brother stopped hanging out because I always missed him being around, and that that feeling never went away. What, an, idiot. To my eternal embarrassment, as I sit here rereading my misspelled words the "Hugo is typing..." text appears and I nearly throw up. True to form he's lighthearted and laughing in his response, asking what occasioned my reaching out to him. I respond -- too much Prosecco and a pot brownie the size of my hand. Realizing the time and that I'm late for a client meeting I quickly dash off my apologies and snap my laptop shut, making a mad run for the shower.

By the end of the day I have successfully pushed all thoughts of that awkward exchange out from my mind, that is until I log back into my computer and see I have another message from him. He wants to get together. My heart slams against my chest and then feels like it seizes. I hadn't even imagined it possible he would want to see me, or if he even lives close! Turns out he doesn't, he's a solid three hour drive north to Santa Barbara, but he says he'll make the trip down to me at the drop of a hat -- for an "old friend." I tell him I'm free this weekend.

Friday comes and my nerves are sparking so raw I feel like my body contains a lightening storm. I hadn't ever dreamed of seeing Hugo again, let alone being out on a date with him. Well, actually, we're staying in as I professed my loathing of restaurants and love of cooking. We're going to cook together -- something I think is so amazing seeing as how no 20 something boy I ever screwed around with could even toast a bagel for themselves. Right on time Hugo knocks at my door at 7 p.m. I have no idea what to expect seeing as we've known each other since we're kids, but here we are now, about to hang out, alone, as adults. I'm dressed in one of my favorite vintage dresses -- a sensual 1930s silk velvet knee length number that's so soft it's like being licked by clouds all over your body. If he lays a hand on me in this dress he won't be able to stop, with this fabric it's a guarantee. It has the added benefit of showing off my trim waist and long legs beautifully. I open the door and it's like one of those bolts of lightening bouncing around in me strikes him and the atmosphere is electric. I don't even think twice, I throw my arms around his neck. His hands are on my hips first and then I can feel him tentatively sliding them around my waist as we laugh our bashful hellos.

We spend the night making stir fry, emptying a few beers, and dessert is some of that leftover brownie from my birthday. Before long we're on the couch watching Super Troopers and laughing so hard we're crying. I can't remember the last time I felt this good. One hilarious scene and his hand finds my knee, and I feel an excited tremor run through me. We've been flirting heavily all night but until this moment he hasn't made a move towards me.

"Hey Clara."

"Yes, Hugo?" Hearing my name is indescribably funny to me and so I start cracking up.

"You know why I came over tonight?"

"There's a reason beyond wanting to see me?"

"No, that is the reason, but there's more to it."

He leaves his words lingering and I make a face signaling, sure, go on.

"I so desperately wanted to kiss you all those years ago, when we had that moment, before your brother kind of told me to fuck off --"

"I'm so sorry about that," I blurt out before he can go on. "It was a stupid thing to do, I only did it to annoy Jacob and it seems it worked too well and totally ruined your guys friendship."

A little shadow of sadness comes over Hugo's face. "Oh."

"No, wait, I mean -- let me start over. You know my brother and I barely got along, yes, but we were even worse before you met him, we poked at every weakness the other had, nonstop. Well, his biggest one was wrestling. He was absolutely in love with it as a kid and I teased him mercilessly about how it was fake. So when you two came home that one day and were a bit drunk and putting on a show acting out one of those dumb, exaggerated wrestling matches, I just thought it would seriously annoy him when I tapped in, but then you pushed him off and pulled me down to the floor.." I trail off, remembering that afternoon clearly.

My brother and Hugo had come home from grad school for summer and were up to their same old shit -- namely being generally some shade of drunk, playing video games, or having people over in the pool. I was busy reveling in anticipation of a few quiet hours when everyone was out of the house to get some reading in, before all my time was thrown over to study as I was about to be a freshman in college, when Jacob and Hugo burst in. I was peeved, I had just settled in and was looking forward to relaxing alone. They had obviously gotten a head start before they each pulled a beer out of the fridge and decided to put on a mock wrestling match and start jumping all over the living room like morons just to aggravate me further. It worked. I decided to beat Jacob at his own game and tapped into the match. Hugo pushed my brother off and dragged me down on top of him, but things shifted quickly. We were pushing about playfully and I think Jacob immediately realized it was his not--so--little--anymore sister in the hands of his best friend, rolling around on the living room floor. He left. We didn't notice.

Between the laughing and trying to pin one another something changed between Hugo and me. I began to notice the way he felt pushed up against me. I had never had the time -- or patience, if I'm being honest -- for boys in high school. None of them caught my eye, anyhow. Sure, I always had had a crush on Hugo, but my brain couldn't conjure up much in the way of sexual fantasies as I was simply too inexperienced there. I wouldn't have even known where to begin. But now, something in me had woken up to his touch. I could feel his sweat through his clothes, his smell was musky and heavy, and he wasn't entirely gentle with me, either. He twisted an arm above my head, I got genuinely aggressive and tried to fight back but he was too strong. His weight on top of me was like a challenge, and, oddly comforting. I couldn't immediately decide if I did want him off of me or not. Then I caught a look in his eyes and realized I was out of my depth, got a bit nervous, and told him I needed water. He let me up.

And like that, we had ruined everything. I always suspected Jacob had been pissed at him for it, but now it was confirmed. This was the reason Hugo evaporated from my life.

"You had to know that I wanted you, back then." Hugo breaks in on my remembering.

"Wanted me?" I return, incredulously. "What? No! I hadn't even the faintest idea. You hardly gave me the time!"

"Well, I guess I wasn't very obvious about it, I couldn't be. But, uhm, when the chance to be close to you offered itself that afternoon, I grabbed it, literally." He lightly laughs. "It was a little opportunistic, I admit, but I was also a little drunk, and feeling bold since you initiated it," he offers a weak grin. "For years after, whenever I heard news about you, I always thought of that day -- when I had you wrapped up in my arms, pressed tight to me. It's all I could think about when I saw your message. I thought you knew that, and had finally been single or something, when you messaged me. And so I came over, because I want the chance to make up for lost time."

I don't answer with anything but a slight shift to face him and put my hand on the side of his neck. Slowly those lush lips find mine and in an instant he pulls my waist towards him. His kiss is unreal, deep and sensual, his tongue finding mine instinctually. I feel a flush, hotness spread through my body. I'm lost in the caresses and don't want to stop but he gently pulls away.

"Any reason we can't continue?"

"No, I just want to look at you to make sure you're really the girl I'm kissing."

"Woman."

"What's that?"

"Woman, the woman you're kissing. I'm not the girl you knew all those years back. In fact, I just turned thirty. I'm a woman, and you're not a boy."

I start giggling again -- because, pot brownie -- at my own ridiculousness so that he just looks at me with those kind, smiling eyes, not getting the joke.

"Ohhhhhh, sorry," I sigh out. "I am so happy you're not a boy though. You're what, 34 now?"

"35."

"That's a good number, I like that number."

"And why's that?"

"Because, Hugo, boys -- boys are shit. And you're no longer a boy yourself, like I last remember you."

"No I'm not." And with that he grabs me again and begins trying to figure out how to maneuver my dress off.

"So, if you wanted this to go further, why are you wearing the Chinese finger trap equivalent of a dress?"

"Side snaps."

I point at my waist and he begins unsnapping my dress and then lifting it over my head.

"One question, though, before we go on," I interrupt, "If you're not a boy, do you know what to do with a woman?"

"That all depends, what does this woman expect from me?"

"Only the opposite of all I've experienced. I want to orgasm, and I want you to be the one to make me."

"Wait," he freezes, "are you telling me you've never cum with a guy before?"

"Not in so long it's quite embarrassing for your entire gender. It's not difficult to make me cum, I'm so turned on right now I could do it just by rolling around with you," I grin, remembering our first innocent-ish romp, "but somehow, boys always manage to screw it up!"

"Don't forget, I'm not a boy. But I am curious, tell me when the last time a man --"

"Boy."

"Boy... made you cum."

"I was nineteen and it was Ryan, my first boyfriend. I came every single time we had sex without fail, and no man --"

"Boy."

"Boy! since, has ever been able to take the credit for my orgasm. He and I just fit together. Talk about double virgin's luck. He definitely didn't know what he was dong, and neither did I, and that magic has not repeated itself since. I can count on one hand -- three fingers in fact! -- how many orgasms I've had with other boys, and it was mainly due to the fact I was so horny they needn't have really been there to achieve it."

"That is one hell of a tragedy. It's a good thing I'm here."

"Do tell!"

"Well, for one, we're going to fuck like virgins."

"Wait, that sounds opposite of what I'm getting at. And how do -- or rather, can -- virgins fuck? That seems like an oxymoron."

"By prolonging their pleasure. They know the art of delayed gratification."

"And what does that entail?"

"Dry humping for hours, for starters."

"Dry humping! You're not serious."

"Not at all," he laughs, "but we are going to slow things down. That's where boys fail, they don't know how to get a woman excited beyond the initial spike of expectation."

"Truer words have never been spoken."

And with this Hugo begins gliding his fingertips lightly up and down my inner thighs, lips teasing mine once more, sending rolling shivers directly to my core. I'm excited, but also hesitant. What if this man, the man responsible for my first feelings of sexual desire, can't live up? Talk about orgasm slaying panic. It's a mental game for us, unfortunately, not just physical. We need to be distracted from our powerful, gymnastic minds.

"Tell me, I want to know exactly what the best sex of your life felt like."

"It felt like nothing at all."

"Now how is that possible?"

He moves his hands to my back and begins caressing and kissing around my shoulders and clavicle, pulling my hair back firmly to tilt my head and give him more open access to the curve of my neck.

"Well, when the sex sucks you can feel every single push inside you, it's so mechanical you feel every movement and are acutely aware of every feeling -- not in a good way. With explosive sex I can't describe it. I guess it doesn't feel like nothing, it feels like everything. It feels like pure pleasure. It's happened to me exactly once and I feel slighted."

"Mmhmm," he coos into my ear. "Now tell me what brings you there, so I know all the right buttons to push."

Kissing and biting my neck in one motion I feel like he already knows. My little blossom is throbbing for him to touch me there and my limbs are weak with anticipation in his firm embrace.

"What particularly blows my mind is when a man knows to take the tips of his fingers and roll them around that little hot spot of nerves that is my backdoor." I laugh at my euphemism. Yep, still stoned. "That he knows his cock alone isn't what gets a woman where she wants to go and doesn't ego trip over it." I grab for his belt buckle and undo his jeans. "This right here, this is where I love to rock against to bring me closer to climax." I pull the band of his briefs away to discover a delightfully trimmed package and drag my fingers across the area just above the base of his hardness.

"Why, you're a little panther, I wouldn't have guessed you liked ass play."

"You haven't known me since I was a virginal college bound freshman, what could you have based any of this on?"

"Touché. Perhaps I meant to say I haven't known a single woman yet who has led with telling me she wants me to explore that area as the first thing that turns her on." He gives a breathy laugh.

"Well, I just know the first time a guy did it to me it was like the floodgates opened and I couldn't even think it felt so amazing. I had to ask him later what he did. I did cum with him once, I suppose for that little trick he deserves credit. I'm not telling you to invade, I'm inviting you to explore and gently roam."

By now I'm sitting astride Hugo's lap, my panties soaked, and he's rubbing me through them, pushing in just slightly enough to make me push back onto his fingers, though the fabric prevents what I really want. He's studying my face with curious intent as I let out little moans to this tease.

"Remember what I said, delayed gratification."

He pulls my face down onto his and lets out a barely audible groan. His cock is so hard and so wonderfully thick I reach down to grab it when he pulls my hands away and holds them twisted up behind my back, pushing my breasts right up to his lips. Lightly biting, licking, and sucking my nipples, the more I move and gyrate the tighter his grip on my wrists hold me still.

"Hugo, this is torture." I whine and writhe.

"Mmmmm," he moans. "I do admit to it," he says before he crushes his lips against mine and releases me to begin grinding against him. Guess we are going to dry hump after all. Soon though, he flips me on my back and takes his jeans off as I practically tear his shirt off.

"Slowly," he hums in my ear, pulling my panties off and then shifting himself atop me.

I can feel the full girth of him pressed up against me now and horny doesn't even begin to describe how I feel. I'm a woman possessed, he practically has to restrain me, again.

"Tell me the one thing you've always wanted from a man but he's never given you sexually."

"I would really love to know what an anal orgasm feels like."

"Damn baby, you do not play around." He pulls me to him and the head of his dick brushes up against my slit, I'm dying to know what he feels like inside me.

"Well, I've done anal a few times, kind of liked it, I'm ready for more. I've not found anyone I've been fully comfortable with enough yet though to get there. Boys and their own pleasure first and all."

"If you're not comfortable, I'm not. That said, let's try to get you what you want, at your own pace."

With that Hugo pulls me back astride his lap and rests his hard-on behind my butt cheeks, pushing it aside to caress my little backdoor rose bud while he pulls my hips back and forth to encourage me to start grinding on him.

"I'm not going inside you until you're near blind with aching need."

And he means it. I'm begging for him to slip deep within me in no time, we're already lightly glistening with sweat from all this extra curricular activity and he hasn't even so much as let me stroke him yet. Every time I reach for him he holds me back, it's driving me absolutely mad. I just want to touch him, everywhere, to do to him what he's doing to me, building up anticipation to a boiling point.

"Please, Hugo, I need you, so bad I can't even tell you," I say in ragged breath as he keeps pulling my hips down hard onto his pelvis, pushing me near to cumming without us even actually having sex. I lift my hips and he playfully yet sternly pushes them back down again. I then bite his lower lip to throw off his game and manage to lift my hips up until I'm hovering just above his thick erection. Our eyes lock and I slowly lower down onto him all the way to the hilt. His hands grip me so tight I feel a tremor surge through me as he lets out a suppressed groan. I want to ride him hard, but he tempers my movements and it's such delightful agony. It feels like nothing and everything.