first time anal
I pull in to the parking lot of the hotel, in town again for a conference. The place is familiar, well-known to me and comforting. My life has been so prosaic – I’ve been in a rut that feels as deep as a canyon. I feel as if I could die from ennui. I’m resigned to attending the conference, but can’t help feel a slight breeze of optimism; with this welcome break in routine and typical of my nature, like a sailboat, I tack into it. Almost against my will, my spirits lift as I check in and get settled.
The next morning, I’m driving into the rising sun, fortified by a restful sleep, a continental breakfast and a large cup of coffee. I still can’t help but feel this is the advent of better things. From where is this ridiculous optimism coming? It’s like a premonition, but of what, I can’t even explain to myself.
As I walk into the conference auditorium, I greet familiar faces and settle myself in one of the middle seats. Several minutes later, the conference coordinator comes in, followed by about a half a dozen of what I assume is her staff. After a brief welcome and introduction, I realize these are her instructors. My gaze rests on each as they are introduced, and my attention is caught by one man, who stands at her side.
He is tall and broad, has dark hair touched with gray, with arresting features and eyes that snap with intelligence and wry humour. There is a hint of arrogance around his mouth, which is full and sensual. As the conference coordinator introduces him, my pulse increases and my mouth goes dry. Why do I find this man so compelling? He doesn’t seem to notice my regard at all, but I can’t see anything or anyone else in front of me.
The conference has begun in earnest. I have no choice but to pull myself together, ask pertinent questions and take notes. The information that’s being imparted is essential to my work at home, and I can’t afford to miss a single detail.
When it’s almost the end of the day, we’ve had several knowledgeable instructors for each topic on the agenda, and there’s only one more topic left. The conference is three days long, but I can’t help but wonder if the man who so drew me earlier would be instructing the class next.
Oh… and he is. He strides to the front of the room to the dais, introduces himself again and immediately confirms what I suspected at first glance: He is incredibly intelligent, articulate and is able to hold our attention with a solid knowledge of his material and a humourous delivery. He emphasizes main points, gesticulating with his hands, and with the quirk of an eyebrow, he has the entire class in the palm of his hand. I’m completely entranced. As he speaks, his gaze wanders between his presentation on the screen, to individuals sitting in the auditorium, keeping them engaged. I’m almost desperate for his eyes to catch mine. Then, for just a second, they do, and it almost seems like his eyes can see right into me. Both eyebrows slightly lift, almost as if asking me an unspoken question. Before I know it, his lecture is over, and he is swarmed by my colleagues, who have to ask him one more question or make one more point… but I know there are women in the class who are like me, and just wish for a few minutes more in his presence. A hot, swooping sensation is in my stomach. I can’t stay another minute when we’re finally dismissed for the day.
In agitation, I drive back to my hotel. I change into clothes that feel uncomfortably tight, and go for a drink in the hotel bar. I have a book with me, but I can’t get past the first page. Colleagues arrive for supper and a drink, but I can’t eat. I finish my drink, make my excuses, and head to my room.
After two hours of television shows I can’t remember, even my skin is tight, and I can’t sit still. I opt for a shower, and stay in the steamy wet heat for at least a half an hour, repeatedly stroking my body, when the soap and shampoo have long since been rinsed away. What is wrong with me?
When I’ve dried off, I step out with some determination, and snap off all the lamps but one in the far corner. The bed is enormous, with four pillows end to end, and I arrange them all to my satisfaction. I reach into my suitcase, and bring out my vibrator, resolved to get rid of this inexplicable craving. I try to start slow, to build the pressure and enjoy the final release, but I just can’t. I touch my clit and find myself swollen and soaking wet, so with no preliminaries, I fuck myself with the dildo, with the attachment vibrating against my clit, and I come explosively in seconds. I’ve just made an incredible amount of noise, but as I lay there still panting, with a fine sheen of sweat on me, I’m all alone in my room and don’t care. But my satisfaction is short-lived. In another minute, as I experimentally play with myself, I realize I need it again. This time, with the image of a big man with that piercing gaze in my mind’s eye, I get there even faster, and there’s no way I want to stop it, as I pluck my nipples with my other hand. Two more times throughout the night I reach for my vibrator, desperate for release, all the time, taunted by his image.
Now it’s the next morning. Again, the sun is shining, and now I feel a different reason for my optimism. I’m so tired, but the anticipation is swelling. I return to my seat in the conference room, eagerly awaiting him. But like the day before, we have many lectures, with many instructors, and none have been him. With one more class again to go before the end of the day, he walks in. At his first word, I’m his again. Again, his gaze wanders to each of us, again, his gaze briefly locks on mine, and AGAIN, his eyes seem to ask a question. I so want to answer… but I’m so afraid this connection we seem to have is all in my head. But he’s so completely knowledgeable about his topic, he’s made it so absorbing and compelling, it would be impossible to not pay attention to him. He holds me prisoner with the timbre of his voice, those large, capable, expressive hands, that enticing hint of arrogance and those sharp, sharp eyes that seem to miss nothing. He can’t possibly not notice the effect he’s having on me. But perhaps he doesn’t, as now his lecture is over, and we’re done for another day.
But this time… he lingers, seeming to take longer than it should to pack up his briefcase, and again, I get that questioning glance that gives me tight little shivers inside. So I take my time packing up as well, wondering if this is all a product of my wishful reverie, or if we’ve somehow really forged this intimate connection that only I can see. Everyone has finally left, and it’s only the two of us in the room.
“Where are you parked?” He asks me.
“Just across the street,” I answer, not quite able to meet his eyes.
“I’ll walk with you, then,” He replies with a twinkle, amused, and seeming to sense how I’m feeling.
Arrogant man! Of course he’s noticed the effect he’s had on me. His self-confidence and obvious assumption that I want him so badly should have dampened the fires of my lust, but with the full impact of his charisma finally so close, I want to pull the very smell of him into my blood. I have no choice but to follow where he leads.
When we get to my car, I open the door and am about to get in, but he stops me with a hand on my shoulder. An electric current runs straight through me, and I know I’m wet. He asks me, “What room are you in?”
Of course, he’d know the hotel, as everyone who’s attending the conference is at the same one. Before I can launch into him for his presumption, my mouth opens of its own accord. “422,” I whisper.
He doesn’t smile when he says to me, “See you later.” Is that later as in tonight? Or later tomorrow, on the last day of the conference?
Either way, my stomach is tight, and I break every speed limit getting back to the hotel. I request a bottle of white wine from room service, strip off my business casual clothes and dive into the shower. The thought of spending another night in the company of my vibrator is beyond aggravating… and the thought of spending it otherwise is absolutely terrifying… and beyond exhilarating. But after my shower, I get dressed in jeans and a t-shirt, with no underwear or bra, and I leave my feet bare. He may have consumed my every thought waking and sleeping for two days, but I have more spirit than to wait on my bed patiently in a bathrobe for someone who is toying with me.
I turn on the TV, more for the company than anything else, and open my laptop. I catch up on the news and read my emails. An hour goes by. Then, two. At the three and a half hour mark, there’s a knock on the door. Hands shaking, I answer it. And there he is. He’s changed into more casual clothes like me, which doesn’t disarm his physical presence in the slightest. He takes in everything about me, from my hair that’s been let down and is damp and curly still from my shower, to my t-shirt, with the outline of my tits with their nipples peaked, all the way down to how I fill out my jeans. I can’t help making the same appraisal. He, too, is freshly showered, and the smell of him is completely clean and free of cologne. I feel my nostrils flare as I take in the purely male scent of him. His long sleeved shirt looks soft and comfortable, but is fitted to his frame. His jeans are snug, and now I’ve lost track of everything else, because he fills them out so perfectly, I know I’ve been staring too long.
“Do I pass inspection?” He asks with a grin.
“I think you’ll do,” I reply, deadpan, finally having found my own sense of humour.
There’s a moment of silence, as he stands in my doorway and we look at each other. I get this funny feeling of a point of no return – that with his first single step into the room, there’s no turning back.
“Do you want to talk?” His voice has lowered, and he’s pointedly looking in my eyes, forcing me to hold his gaze, as he seeks my honest answer.
There could be only one answer to give him. “No,” I whisper, and step back.
He steps in the room completely, and the door closes behind him with a snick that seems overly loud in the charged silence. At the sound, my heart races, and I’m trembling. A random thought occurs: Strange, how sex, fight or flight are all so closely linked.
He deliberately walks toward me, slowly; I walk backwards, until the backs of my knees are touching the bed. The expression on his face is so intense, so arresting, I’m not sure what he plans on doing first. To my surprise, he stands in front of me, cups my face in both of his slightly callused hands, and kisses me… and kisses me… sliding his tongue along the seam of my lips so I’ll let him in, stroking his tongue with mine, sucking on my lower lip until I’m whimpering. I’m so close, if I rise up on my toes, I might be able to rub my clit close to his cock. As I stand on my toes to do so, he reaches behind me, grabs my ass, and pulls me up to where I need to be. My control is gone, and I’m rubbing against him with wordless pleas. But he has his own agenda. When he’s done, I’m gratified to see his kiss-swollen lips and to feel his iron cock pressing against me, but my patience has vanished. His seems to as well, as he grabs the neck of his shirt to pull it off in that masculine way. When he pauses, I take advantage, all shyness gone, and lick my way across his nipples, up to the line of his jaw, down the cords of his neck, his taste intoxicating. He doesn’t indulge me for long.
He grabs my t-shirt from the bottom and lifts it off, eyes widening at the lack of bra underneath. He glances down at my bare toes, then back to my face, with that sexy, questioning look again. I quirk an eyebrow as if to say, “If you want to know what else is underneath, there’s only one way to find out.” I love our body language; I love the way we stay silent, but say so much. But he, too, gets distracted, cups my tits in both hands, suckles my nipples and buries his nose in my cleavage. He trails two fingers down the middle. I shudder, thinking of him running something else long and firm down my cleavage. I look into his eyes, and I can see the exact same thought, and suddenly, the reins snap.
He rips my jeans off, pushes me backwards onto the bed, with my legs still dangling over the side. He crouches in front of me, and opens me like a flower. I’m panting… I want to stay quiet for awhile, because I just know he’ll be wringing sounds out of me that I’ve never made, but I can’t hold back the moans. He begins to lick, sliding just around my clit, enough to drive me crazy. His lips rub my clit, then slip away to lick around it again. My moans are getting louder, and I can’t stay still. He pulls up my legs so my feet are flat on the bed, then pushes my knees outwards, so he can hold me down better. I’m frantic. My hips are lifting in time. One of his hands is under my ass and a finger has slipped into my asshole. My eyes snap open, as it’s uncomfortable, at first. But he keeps licking and sucking. Another finger slides in, and seems to be rubbing against an inner wall I can’t imagine. While yet another finger has found another entrance, sadly neglected to this point, and aching to be filled. My panting is louder, my noises are totally out of my control, and my head thrashes on the bed. I start begging.
“Please…please…PLEASE!… I can’t…”
He lifts his head up, his eyes now on fire, his lips wet with my juices, and his voice like gravel, “You can. You WILL.”
Now he leaves his fingers in my ass, and totally concentrates on kissing and sucking on my clit. The pressure is building. My heartbeat is racing. I don’t know where to put my hands, and they land on my tits, squeezing and pulling. When he looks up to see this, he hums against me, and then I completely shatter….”OHHHHH!” Oh, god… where does the magical mystery tour go from here?
Without giving me time to recover, he pulls me to my feet, then walks us to the hard-backed chair sitting in front of the desk. Intrigued, I watch as he sits down, then pulls me to him, so I sit facing him. I may be spent, but he certainly isn’t, and I’m immediately impaled. “Ohhh…wow…” The possibilities seem endless to me. I can rub my tits against his chest, kiss and lick so many things, nibble on his jaw and his ear… but once again, he’s ahead of me. He grabs my hands and pulls them behind me, able to hold both in only one of his. He grabs my hair in his other hand, and steadily pulls back, until my head is back tight and I can’t reach anything on him. Just as I was his prisoner in the classroom, he has me willingly imprisoned again, and I’m so turned on, I can hardly bear it.
“Now what are you going to do?” He asks me roughly, slowly raising and lowering himself, so my body rides up and down his turgid cock. I rock against him in counterpoint.
But I’m through letting him have his way without a fight, so I say, “Hmmm… what do YOU plan to do?”
He stops moving and says, smugly, “Nothing, I think.”
I squeeze the muscles of my cunt around him, and he just slightly flinches. I’m not totally defenseless.
Well, now the gloves are off. He picks up the pace, until I can no longer hope to keep up, and now the hand has moved from my hair, sneakily down my back and his fingers are in my ass again. This time, they’re welcome, and I eagerly rotate my hips around his fingers and cock, until I feel the inevitable pressure building again. With little warning, the wave crashes, and I almost scream this time, before collapsing onto his chest, boneless, soaked in sweat, his and mine, and bodily juices from him and from me. The smell of sex is in the air, and I’m loving it. But as I catch my breath, I realize, he’s still hard inside of me. He’s been so in control, so playful, and so generous, I’m dying to return the favour.
I lean back, this time I give him the questioning look, and gently ease myself off his jutting cock. I kneel in front of him, as he still sits on the chair, pull my hair to the side, and gently put the head of his cock into my mouth. I can taste myself, and as I run my tongue down the slit at the top, I taste the pre-come, too. My mouth waters… this is going to take some time. I pull the full length of him all the way in, and it’s significant. I let him out, and suck for a while on the very head, eliciting a moan. But I’m after more of a reaction than that. I lick all the way down to his balls, following the vein, and take them into my mouth, running my tongue underneath. The moan is a little louder, this time. I glance up, under my eyelashes, and I’m seeing some of what I’m wanting from him…his face is flushed, his eyes are burning, and the tendons are standing out at his neck. But he’s still holding back. I relax my throat and come back to the head, pulling the entire length in again, so the head rubs against my soft palette, and part-way down my throat. I put both hands on his hips, and pick up the pace. I become so absorbed in what I’m doing, I’m moaning myself, and don’t want to stop. His hands are in my hair, holding me in place, and I can tell, that just for a second, whatever plans he had, he’s tempted to let me take him, to come in my mouth and let me drink him in. With one last thrust, he pulls away.
He then throws me bodily on the bed, face down, and I can hear him breathing hard. I’m not a slight woman, and his sheer strength takes my breath away. I look over my shoulder, and the look in his eyes is almost of a wild thing. He grabs my hips, and pulls me to him. He grabs my lube from my suitcase… how in the world did he know that was there?… and I can hear him spreading a generous amount on his hands. He grips my ass, pulls the cheeks apart, and rubs his fingers over the entrance of me. And now I understand… all those times earlier, with his fingers moving in and out, he’s been readying me for his possession all this time. I think I’ve been ready for his possession my whole life, and while nervous, I can’t wait. He puts still more lube, straight from the bottle, in the crack of my ass, massaging it in, dipping his fingers in my asshole and stretching the tissues as gently as he can. It feels a bit strange, but by the trembling of his hands, I know he wants it badly, and I’m going to give it to him. After rubbing some on himself, half of the container of lube is gone, and neither of us is holding anything back. He takes my hips, and pulls me to him… fits himself to the entrance of my ass, and slowly, eases in. It’s TIGHT. At first, I can only take the head of his cock, moving in and out, but the feeling becomes so incredible, I raise my hips instinctively, and pull him right to the hilt.
OHHH… Not sure if I like it… wait a second. Can I still tighten around him? I pull everything as tight as I can, squeezing the muscles of my cunt, squeezing my ass cheeks… NOW I get a reaction! NOW he’s making noise, and oh my god, NOW he’s picking up the pace. Ohhh… and hitting this place inside me… somewhere I’ve never felt before… almost like I have to pee, but not… “OH GOD, PLEASE GO FASTER!” I’m overwhelmed… overpowered… and completely owned. He’s pulled my hair back so tight, my neck snaps back and tears involuntarily start in my eyes. I don’t care. He still isn’t pulling hard enough. But there’s no way I can keep up. He’s the storm, and I’m just hanging on, hoping I won’t get swept away. He’s taunting me, too.
“You like it, don’t you? You like it in your ass. Tell me you like it.” His hot breath is at my ear, we’re covered in sweat, and the sounds of our bodies slapping together are so raw, so primal.
“I love it!” I gasp, unable to say anything else. “I think I’m going to….oh god…”
“You’re going to come?” He rasps out. “Then come for me. COME for me. NOW!”
And, incredibly, I come, and soak the bed like I’ve never done in my life; it’s simply everywhere. I’ve been taken apart and put back together, and am no longer my own person.
I watched as Simma expertly wheeled the mouse around the spreadsheet, my hand resting lightly upon her shoulder next to a cascade of red hair. I had been working for three months now at the headquarters of Systems International in Yevczich, the capital of the small eastern European republic of Rolennia. Simma was my secretary—in fact she was the main reason I had quit my New York job and hauled my ass almost 4,000 miles to a berg no one I knew had ever heard of. The thing that amazed me is how facile she was with a mouse. It was like an extension of her hand… I had worked with computers for my whole career, but using a mouse just wasn’t as second nature to me as it was to Simma. Maybe that’s because Simma was just 23, and so she had been using a mouse basically since birth, when she had access to a computer. In a poor formerly Soviet-bloc country whose best-known exports were porn stars, those weren’t always easy to come by.
“And zat is how you update ze exchange rate,” she explained proudly. Her English was outstanding if accented in a country where not many spoke it.
“Simma, you are amazing. Are you sure you never went to college?”
“Only one University in Rolennia. Top five percent of… how you say, high school? … get in. I finish six percent. I no have money to go school out of country, so I end up here.”
“And am I ever thankful for it,” I agreed, kissing the bright red hair on top her head gently.
“Stop it,” she purred quietly, not really mad. “If you want kiss, I come in office.”
“I’d like to come in my office,” I agreed. Simma smiled, understanding my double-entrendre perfectly. She locked her workstation and followed me in, closing and locking the door behind her. I sat in my chair, turned sideways to my desk. Simma came by my chair, rested her hands on my armrests, and kissed me sweetly. Then with a smile, she proceeded to perform her duty… unzipping my pants, she expertly extracted my erect penis and proceeded to go down on me. See in Rolennia, not only does sexual harassment not exist, but secretaries are expected, required even, to attend to all of their bosses’ needs—most especially their sexual ones. Being a secretary here can be a 24-hour job–at least it was for Simma, because I had never spent a night in Rolennia where Simma wasn’t a welcome guest in my bed. But that is a somewhat unusual arrangement, which is why she didn’t want me to kiss her in public. Most of the secretaries never got kissed by their bosses although they were dutifully having sex with them two or three times a day. Whereas most executives would send their secretaries away to sleep in their tiny private rooms on the first floor of the executive living quarters after the last fuck of the night, Simma spent her nights in my king-size with satin sheets, my arm wrapped around her slender waist to ward off the cold. I treated Simma like, well, a girlfriend rather than a sex toy, and I had heard rumors that there was some jealousy among some of the other secretaries because of it.
Simma sucked my dick with her usual mid-day efficiency. By now she knew just the right pace, just the right length of stroke, and just the right delicate spot over which to repeatedly run her tongue, so that she could suck me from zero to climax in just a few minutes. Efficiency was the order of the day when it came to mid-day blowjobs; she generally didn’t bother to remove or even loosen any of her clothes–she knew I would take great delight in undressing her at bedtime. She would sometimes complain playfully on days where I was not satisfied with her talented mouth and wanted her body as well, that requiring her to remove clothing and lay down on my desk would put her behind on her work for the rest of the day. So most of the time I just let her suck me dry, marveling at the beautiful face wrapping its lips around my dick, watching her marvelous red hair bobbing in time with her neck.
I liked to rest my hand gently on her head, running my fingers through her hair sometimes, just to maintain connection to Simma the person while she was servicing me. She turned her eyes up towards me, knowing that I would be watching her yet not self-conscious. Our eyes met and gazed softly at each other. We weren’t just a randy boss and his dutiful secretary; I felt like I had a relationship with Simma, and the way she looked at me sometimes made me think that she felt at least a little that way, too.
Simma was watching my eyes for another reason as well. She couldn’t quite explain how, but she tells me that she can tell in my eyes when I’m about to cum even before she can feel it in my penis. She must be right, because just about the time I feel my nuts seize and start to churn out the spunk, Simma has switched from suck mode to swallow mode. The fast, focused sucking and tonguing is replaced by a slow, gentle movement where the sucks me deep, then twists slightly as the releases me, running her tongue along my length like she is wiping me down. It is almost always in this position that she receives my cum in her mouth. She will repeat this motion three or four times, collecting the sperm in until she feels the spasms end. Then she will release my dick, pool the whole load on her tongue, open her mouth briefly to show the spunk on her tongue, and then swallow it with a decisive, deliberate and incredibly sexy motion. She will open her mouth again to show that it is empty, and then she will take a moment to clean my softening dick, tongue licking it as a cat licks its kitten. While she does this I am usually reaching into the drawer for the breath spray; she knows where it is, but I think it’s the least I can do to fetch it for her. When I’m too soft to bother with, she lets my dick fall from her lips and sprays her mouth with the minty freshness before leaning over and sharing a lingering kiss of appreciation.
This pattern may be predictable, but it never gets old. Today, however, there was a departure from the routine because Simma had something she wanted to talk about after the post-swallow kiss. “Do not forget… today all-secretary meet.”
“Oh shoot, I did forget,” I admitted. “With Ivana?” Simma nodded. Ivana was… the matron you might say of the secretarial corps. A house mother of sorts. She was one of the original secretaries when SI was founded–some say that the whole fucking-the-boss-is-expected thing was her invention, but there’s no evidence to back that up. Now 40 something and three kids later, she could still turn heads walking into a room. She was the only female employee at corporate headquarters that did not directly report to a boss for whom she was expected to perform sexual favors. Instead, her job was to oversee the other girls to make sure that they were doing their jobs. If a girl wasn’t doing a good enough job satisfying her boss for whatever reason, Ivana was the one to broach the subject. If a girl needed something to please her boss–a sex harness, a nurse’s uniform or double-headed dildo–Ivana would get. And if a boss was getting too rough with his secretary and putting her in danger, Ivana would be the one to tell him to cool it or he would lose secretarial privileges. In short, she wielded as much power as my boss did, only in more subtle fashion. “Do you know what it’s about?”
Simma shook her head again. “I do not, but other secretary tell me it is probable refresher training.” Recruitment and training of secretary’s was another of Ivana’s jobs. She would find the most beautiful girls in the country and offer them jobs at SI; many had little sexual experience when they started. Ivana made sure her girls were up to whatever advanced kinkiness their jobs may require before placing them with an executive.
“Any idea when you’ll be done?” I asked, thinking ahead.
“I not know. You eat without me, yes?” This was another way in which I was unusual. Most cooked for their bosses, then took mealtimes as a rare time off. Simma and I always had dinner together–and usually I cooked, for the simple reason that Simma’s cooking was terrible. But I could cook some, and I hated eating along, so it was only natural in my mind that I cook for the both of us. When you’re with a girl that’s half your age and looks as great as she does, a little cooking is a small price to pay for the tail you get.
Simma went off to her meeting at 3. I hung around the office until 5:30 in case she returned, but she did not. I went home and started dinner, hoping she would be back to eat. When she didn’t return I started eating. I was just finishing up at 7:15 when I heard the door open. I got up from the breakfast counter; we met in the middle and hugged. “Wow, that was a long meeting.”
“Yes,” is all she said.
“Are you hungry? There’s food in the kitchen, I’ll warm it up for you.”
“No I not… well… jus a little please.”
“Of course,” I smiled and gave her a kiss. But there was something funny, something distracted about her demeanor. I wondered what they had talked about at her meeting as I went into the kitchen to reheat her food.
I came out with her dinner on a plate five minutes later. Simma was sitting in her usual seat at the breakfast bar. I served her and took the seat next to her as I always did. “So what did Ivana want to talk to everyone about?”
“She want everyone get ready for big convention,” she said between bites.
She gave me a funny look. “Mr. Thurman not tell you of convention?” I shook my head. “Rolennia Business Exposition. Rolennia is not big country–all big business man and government go to convention. They talk, deal get done–they say you not can operate in Rolennia if you not shake right hands at convention. Maybe give bribe too, I don know.”
“That’s interesting–no, I hadn’t heard about it.” But then I thought “so why was Ivana talking to YOU about it.”
“Convention… not so much about business as is fun for business man? Lots of drink… lots of sex… all businessman bring secretary to convention. Then maybe he make trade to have sex with each other secretary, or maybe share…” My anxiety spiked immediately. I was not about to share Simma with anyone. “Ivana say is like orgy for three day. Many time secretary get offer new job after convention. If girl now job not so big pay, is good opportunity to move up. But SI is pay very well; we not want very much to get new job. So instead we host.”
“What does that mean?”
“We work… like serve drink, greet guest, thing like so. So we maybe not have so much sex as most girl, but Ivana want we train in case. Is up to boss.”
“What is up to your boss?”
“Dey tell us convention rule: no one touch other man secretary without permission. So is up to you if you want I have sex with other man or no.”
“Not for you, Simma,” I declared. “I don’t care if the Prime Minister asks, I’m not sharing you with anybody!”
She smiled almost condescendingly and gave me a peck on the cheek. “You sweet man Marteen. I know you mean well. But is important to play by rule or maybe lose job. And if you lose job, I lose job. You not want that, I not want that. Is no big deal, have sex with other man sometime. Is just one day.”
I paused, thinking. Yes, Simma and I had much more of a relationship than any other boss and secretary at SI, but her response reminded me that ultimately that was still what we were. I really had feelings for her, and while I liked to think that when we snuggled in bed after sex she had feelings for me too, the fact is that even after three months together I couldn’t say for certain that she would have anything to do with me if it weren’t her job. I could tell she didn’t relish the idea of having sex with a stranger, but she had this resignation that that might be what is required–I’m sure that’s how she first felt about me, too. I hoped that she didn’t still… but I really didn’t know. “I don’t see why I would even be going to this thing. I work entirely with people inside the company; why should I go meet these people when I won’t see them again anyway? I’ll tell Tom I shouldn’t go to the conference–and if I don’t go, you won’t have to go either, will you?”
She chuckled. “System International host of conference. ALL staff go to conference in some way. You want HOPE you go as guest, or else you will go as worker. Is better to be guest I think.” I frowned… there must be some way. Simma changed the subject, sort of. “Even if I not go, I must still do training.”
“Do training? You mean you aren’t done? You have to go back for more?” I was really anxious now.
“Maybe. Is depend.” She started to get the confident swagger in her voice when the topic of conversation turned to sex.
“Depends on what?”
“Is depend on if I show I not need training… because I already know how…”
“Ahh,” I said, catching on to her suggestion. “So if you can prove that you are already doing it with me, you don’t need to go back training.” She nodded her head like a woman with a secret. “Is that the way you would rather do it?” Now I was the one teasing.
She flashed her eyebrows at me. “I MUCH rather you train than Ivana.” I could tell she meant it.
“And just what do I need to do?”
She didn’t answer, but bit her lip in a sexy schoolgirlish way. She slid off the chair, turning her backside in my direction. She thrust her butt out, then slowly and sensually hiked up her miniskirt. I watched with great interest, although I hadn’t caught on to where this was leading yet. I saw the tiny thong she usually wore… only something was funny about the way it lay… loose-like, not tight to the crack. But Simma didn’t stop… as I pondered what was different, she sensually pulled the strip of fabric to the side. Something bright red and plastic was somewhere it didn’t seem like it ought to be. It took me a minute to figure out what it was. “Is that… a butt plug?”
She smiled over her shoulder with a twinkle in her eye, continuing to show me her ass. “How long have you been wearing that?”
“Since start of meeting… two three hour maybe.”
I couldn’t imagine sitting through a two hour meeting with a plug stretching my asshole. I also couldn’t imagine starting a meeting by giving every attendee a butt plug and expecting them to put it to immediate use–but I’d like to be given a chance to try. “Wow… well I’d sure love to help with your, uh, training, but I’m not exactly an expert.”
“Is not so difficult. I have train before.” I imagined she did–I’m sure that before they let her audition for the secretary gig, Ivana made sure she could take one up the ass. I could just picture her with a big black strap-on… the possibility hadn’t come up between us before, however. I guess I couldn’t blame her for not volunteering that information.
“So you’ve been prepared to have anal sex with me from the beginning?”
She turned around, wrapping her arms around my neck with an I-have-a-secret smile. “I tell you from start, I do anysing you want I do…” and then she kissed me. My hands fell to her slender waist, naturally, comfortably; I had gotten quite used to holding Simma close, in a good way. But it was not lost on me that she was the one that initiated this kiss. Oh we kissed a lot, but I was always the one to initiate, except for sometimes right after she had an orgasm. The only other time I distinctly remembered her initiating a kiss was when I was interviewing for the job, and she was doing her best to seduce me in order that she could get this coveted secretary position. The fact that I was here in Rolennia was testament to her power of persuasion… although I wondered sometimes if it would have changed her mind if she had known in advance that I would want her by my side 24 hours a day.
The kiss ended; Simma flashed her eyes at me dreamily. “I not know, maybe is too early go to bed?” she purred.
“Oh no. I’m quite ready to go to bed now…” I growled lustily, kissing her again. I was already hard–not so much from the prospect of exploring Simma’s ass as from the fact that she was the one initiating the festivities. I suppose there wasn’t much need for her to–I called her into my office when it was time for our fuck-break at work, and at home it was understood that bedtime meant sex time. Unless I wanted it sooner, in which case I initiated that too. Here was a situation where she wanted to get things started, however, and so she was doing the fire-starting–and I was LIKING it.
Simma took my hand and we sojourned to the bedroom. But then Simma gently took my shoulders and sat me down on the bed. She stood before me confidently and unbuttoned her suit jacket. She slipped if off her shoulders and tossed it aside. Then she knelt before me, reaching for my belt with a twinkle in her eye. I lifted my butt off the bed slightly so Simma could slide my pants off. She folded them quickly and laid them aside, then pulled off my boxer briefs and socks, leaving me in just my dress shirt. Her eyes looked up at me knowingly as she bent over, opened her lips, and started caressing my cock with her tongue. She knew exactly how I liked to be sucked.
If I live to 100, I will never grow tired of feeling Simma blow me. For one thing, she had, like, different styles for different occasions. This afternoon was the no-nonsense blow job, steady and intense in order to achieve orgasm as quickly as possible and get back to work. But tonight, she was doing my favorite style. Her lips caressed the skin as my dick slid between them; her tongue teased my tip relentlessly, but her pace was slower. The result was to excite my penis to its absolute breaking point, and then maintain that level of arousal for as long as she chose to. She would sometimes stroke my balls or vary it up with the occasional deep-throat, but most it was concentrated pleasuring of my most sensitive spots. All she would have needed to do was pick up the pace a little and in no time she would have a mouthful of spunk, but that is precisely why she didn’t. It was the perfect foreplay prelude to any other sexual activity, because it made my cock as hard as a frigging iron bar.
I loved to watch Simma’s pretty, youthful face swallowing my cock, loved to see her red hair bobbing in time with her neck. As she sucked me tonight, she was simultaneously unbuttoning her blouse at a deliberate pace. I watched as more and more of her pale, lightly freckled skin became visible with each button. Familiarity did nothing to reduce the anticipation of seeing it again.
The last button undone, Simma stripped the blouse slowly from her shoulders and laid it aside. Her head was down, concentrating on sucking my cock the whole time. Then she unhurriedly reached behind her to release the strap of her black lace bra and slipped that off as well. I smiled slightly to myself as my eyes could feast on the sight of her young, firm breasts, standing out proudly in defiance of gravity. Like a stripper, she pinched her own pale nipples lightly between her thumb and forefinger then rubbed the length of her forearm across the, making sure they were excited and erect although it appeared to have been wholly unnecessary. Ahh… I felt myself get just a tiny bit harder, like from iron to steel, because although she could suck me off out of sight under a table (I can say that for a fact), my favorite way to watch her blow me was when I could watch and fondle her bare breasts as well.
Simma wasted no time moving from her buttons to mine, head still down and bobbing up and down on my Johnson. I watched, appreciatively, feeling this slight sense of surrealism I often felt watching her suck my dick. A woman nearly half my age, beautiful as a movie star, sucking like a porn star and it was my dick in her mouth–sometimes it was hard to believe that this was real life and not a fantasy dream.
Simma’s eyes gazed up at me, wondering if something was wrong. Normally when she sucked me topless I held and fondled her breasts in my hands at the same time. I smiled at her gratefully, then gently ran the fingers of one hand through her hair. Reassured I just wanted to vary it up a little, she focused again on my cock and sucking me.
I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go to bed early. Unfortunately tonight was no exception.
As I waited for my computer to boot up I started thinking about how much porn I had watched lately. I had all different kinds of straight porn, from amatuer to anal to threesomes, but for some reason I had found myself increasingly drawn to shemale porn lately. The first time I came while jacking off to a shemale video I felt weird afterwards, like there might be a chance that I was gay and didn’t know it, but after a while I realized that just because I liked looking at hot chicks with hard cocks that didn’t mean I was gay, it just meant I was expanding my sexual horizons.
When the computer was ready I decided not to look at my straight porn and instead found a video online of a good looking shemale stroking her hard cock. Pulling my pants off I squirted a little lotion in my hand and began rubbing my already hardening cock. The shemale had a big cock, long and hard, and although it was longer that my six inch cock and definitely thicker I was turned on by her large cock. As she started to get close to orgasm I increased the pace of my own stroking and as always I tried to time my cumshot with the video. My timing was impeccable and I managed to shoot my load at the exact same time as the hot shemale I was watching.
As I watched her cum pool in her belly button I wondered, not for the first time, what it would be like to see a real shemale in person. What would it be like to touch a shemale’s cock? Would I like it? I had only been with women before and with the exception of my college girlfriend occasionally massaging the outside of my asshole when we had sex I had never really been that adventurous in bed or willing to ask for something I wanted to try. In fact, the only reason my college girlfriend did that was because she said her ex liked it and she had heard most guys did.
After logging off the computer and cleaning up I ate a quick dinner and then retired to the couch for some tv before bed. About 9 o’clock I got a text about dinner on Friday night with some college friends and I gratefully accepted. Pretty soon it was time for bed and a chance to do it all over again the next day.
Thankfully the week passed quickly and Friday arrived in no time. When I walked in the door after work on Friday I went straight to my room to get ready. After a quick shower I dressed in a collared shirt and jeans for dinner at a new gastropub and bar which had just opened down the street from me. It was going to be good to see my college friends again. We had all graduated together about two years prior and were all single and working too much. Being the typical shy technical guy I had a hard time making friends at work but with my college buddies I felt like I was always able to relax and be myself.
I walked the three blocks to the restaurant and found my friends in a booth in the back. After some good natured teasing and catching up we had a nice meal. The food was good, the beer was excellent and after a few hours and a few drinks it was time to say goodbye. After shaking hands all around and everyone heading out I decided to make one last trip to the bathroom before my short walk home.
Standing at the urinal peeing I listened to the two guys at the sink have a conversation about their dates and which one of them was going to get lucky. Shaking my head at my predicament of going home alone I washed my hands and exited the bathroom. I pushed open the door and immediately ran straight into someone coming out of the women’s bathroom across the hall. I didn’t think I was moving that fast but when we collided, her and I and her purse went flying in all different directions. As I caught myself I quickly turned around to see if the woman I ran into was unhurt.
She had braced herself against the wall in the hallway so I quickly closed the space between us and extended my hand to her elbow to help steady her. As she got her heels back under her she turned around I got my first look at her. She looked to be in her early twenties, dark hair down to her shoulders cut to frame her cute face. With heals on she was tall, although still two or three inches shorter than me at 6′. With her thin frame and budding chest she looked like a dancer about to do a pirouette.
“Are you ok? I’m sorry, I didn’t mean to come barreling out of the bathroom like that.”
“Oh I’m fine,” she answered with an off-handed flick of her wrist, “I’ve had worse.”
Her answering smile not only seemed to reassure me that I would not be getting chewed out but it also lit up her face and made her that much more attractive. I smiled and bent down to pick up her purse only to realize that everything that was inside her purse before we collided was now on the ground. She bent down next to me to help gather up her things.
“So you run into a lot of girls here?” she asked as she playfully nudged me with her shoulder.
I did my best to keep the nervousness out of my laugh. “Nope, you’re the first.” After picking up her cell phone I quickly added, “I guess it was all just part of my plan to get my hands on the new iPhone here.”
Taking it out of my hand and putting it in her purse she asked what kind of phone I had.
“A blackberry. Unfortunately my iPhone was having connectivity problems with the server at work so I had to switch.”
“The server huh? What do you do?”
After standing and helping her up I started to explain about my IT job. After thirty seconds or so of non-stop talking I finally realized that if some random cute girl I almost flattened against the wall was asking questions about me and my boring job that must mean she was at least somewhat interested in me. Thankfully I had had a few drinks so I stopped mid sentence and summoned all the liquid courage I had.
“Can I buy you a drink?”
With that bright smile returning to her face she replied, “I thought you’d never ask.”
I ordered us two drinks at the bar and we grabbed some barstools. I didn’t have a lot of experience with girls so I just started asking questions. She opened up pretty quickly and I managed to get a good picture of who she was. Her name was Amanda and she grew up not five miles from where we stood. She still lived close by and had come to dinner here with a friend but her friend had just left because she had to work early in the morning.
Over the course of our conversation I came to realize that Amanda was funny, engaging, outgoing and kind of a flirt. The first time she brushed my leg with her hand I thought it was an accident but after about ten minutes she just placed her hand on my knee and left it there, slowly making circles with her fingers while talking. I was still too shy to make a move but thankfully Amanda wasn’t and after about thirty minutes her circles had moved slowly up my leg. Once her finger even brushed against my hardening cock. I saw her glance down at my crotch a few times and get the beginnings of a smile on her lips before she would dive back into the conversation.
After an hour and a few drinks at the bar together Amanda leaned in close and whispered, “Would you like to get out of here?”
I couldn’t answer ‘yes’ quickly enough and the next thing I knew we were exiting the bar and she had grabbed my hand. “Your place or mine?” I asked.
“Yours, it’s closer and I have to pee.”
We walked the three blocks to my apartment with my hand in hers. Unlocking the door I pointed out the bathroom and sat on the couch. As I listened to the faint sound of her peeing I couldn’t believe my luck. I literally ran into a super cute girl at the bar, we had a great conversation and there we were back at my apartment. Were we going to fool around tonight? I was probably too chicken to make that big of a move but I was pretty sure from our conversation that Amanda was the type to dictate that anyway.
Amanda exited the bathroom and sat down next to me on the couch. Her hand immediately returned to my leg and I felt my bulge rising again. As I turned toward her she pounced, mashing her lips up against mine. Her kiss was soft and passionate at first and then slowly she began to be a little more aggressive. Her mouth parted and her tongue found it’s way into my mouth. It had been months since I had kissed anyone and years since I had enjoyed it this much.
Her tongue swirled in my mouth while her hand slowly made its way up my thigh. It only took a few seconds before she was rubbing my cock through my jeans. As our tongues danced she got a firmer grip on my cock and began massaging the entire length of the shaft. After another minute of rubbing my cock Amanda took her hand away and started undoing the buttons on my shirt. After getting it open she broke our kissing to reach down and in one swift motion lift her own shirt over her head. Now in her bra and jeans she strattled my lap facing me and ground her ass down onto my hard cock.
She traced her fingers down my chest and then moved to the button on my jeans. She unsnapped it and slid the zipper down, giving my trapped cock a little air. Without a word from me she leaned back and undid her bra, allowing her small yet perky b-cup breasts to sit right at my eye level. Watching my hungry eyes devour her chest she asked, “See anything you like?” followed by that great smile again.
Amanda leaned back in and pressed her naked breasts against me and then slowly slid down my body. She kissed my upper chest then she licked and sucked each nipple. Going down she soon arrived at my unbuttoned pants. She hooked the top of my jeans with her thumbs and in one motion pulled them down and off. Tossing them behind her my boxers quickly followed and before I knew it she was knealing between my bare legs with my exposed cock inches from her face.
Taking my hard cock in her hand she planted a kiss on the head while making seductive eye contact with me. She licked the back of the cockhead and my dick twitched in her hand. Using her tongue to bathe the underside of my cock, she slowly slid my cock in her mouth inch by inch until she was all the way down. Sliding it back out she started to pick up the pace of her sucking. I can honestly say that I had never had a blow job like this before. With her hot mouth, swirling tongue and spit-smooth motion it’s a wonder I didn’t cum in the first few seconds.
While her mouth was on my cock her hand started gently massaging my balls. No sooner had I gotten used to her fingers tickling my sack she slid them down to my ass. At first she just teased the outside of my hole but in no time I felt her slip a finger in to the first knuckle. The moan that escaped my lips told her how much I enjoyed that so I felt her saliva lubricated finger push deeper. She bottomed out her entire index finger in my ass before slowly sliding it back out. The feeling was slightly uncomfortable at first since it was unlike anything I had ever felt before but after she finger fucked me for few seconds it started feeling good.
After working her finger in my ass and her amazing mouth on my cock for a few minutes I started to feel the pressure in my balls build up. I started to sit up to let her know that her amazing oral and hand skills were going to make me cum soon when she slowed her mouth and finger to a stop. Taking my cock out of her mouth with a pop she smiled up at me and then slowly rose to her feet. Looking down at me she grabbed the button on the front of her jeans and made eye contact.
“Do you like surprises?”
My first thought was that she had totally shaved public hair or something. With a stupid grin on my face I replied, “Oh, I love surprises!”
She winked and smiled and said, “We will see about that.”
She undid the button of her jeans and slowly slid the zipper down. Swaying her hips back and forth she worked her skinny jeans down her legs until they were piled at her feet. Her body was amazing, I couldn’t stop my eyes from traveling down from her cute face, past her perky breasts and flat stomach down to the black thong she was wearing. With the low light in my apartment it almost looked like there was a bump there but I just figured all the shemale porn I had been watching lately had gotten in my head.
As if reading my mind Amanda traced her hand down her stomach and let it come to rest on the bulge in her thong. I couldn’t believe the bulge was real. “Have you ever heard of a transsexual?” she asked.
“Shemales? Ummm, yeah I guess.” My nonchalance was betrayed by my cock springing back to full attention at her mention of transsexuals.
Looking down at my now rock hard cock she smiled and said, “I think he might be more familiar with them than you are. And it looks like he likes it.”
I laughed and nodded my head. “Does that mean you…”
I trailed off as she hooked her fingers into the slides of her thong and slowly slid it down. Her semi-hard cock sprang out and stood at half mast not a foot from my face. I had never seen a cock in the flesh besides my own and although I had watched hours of shemale porn it was surreal to see a cock sprouting from between the legs of this beautiful feminine creature. I was mesmerized by her cock and even though it wasn’t fully hard yet I knew her cock would definitely be longer and thicker than mine. I had also never seen an uncircumcised cock before but seeing her cock head hiding behind a thin layer of skin was a huge turnon.
I leaned forward and reached out, taking her cock in my hand. She gasped when I touched it but when I looked up she had pure lust in her eyes. I began stroking her cock and I felt it get harder in my hand. After a few pumps her cock was hard and had to be at least eight inches. A glistening drop of precum began to form at the tip of her cock and before I knew it I was leaned forward and extended my tongue, licking the precum off the tip of her cock. It was salty and warm and immediately I knew I wanted more. I moved the head of her cock to my lips and used my tongue to lick the back of the cockhead like she had done to me. I heard her moan as I took the head in my mouth.
The taste of her cock was unlike anything I had ever tasted before, it was earthy and warm but definitely tasted like it belonged on her hairless feminine body. I took as much of her cock in my mouth as I could before I had to slide it back out. After taking her cock in and out of my mouth a few times I felt her hands in my hair, lightly applying pressure to the back of my head as I slid my mouth back down on her cock.
“Oh yeah, just like that. You’re a natural baby.”
Her praise of my cocksucking made me even more excited. My rock hard cock bounced against my stomach as I bobbed up and down on her cock. As I continued sucking her moaning increased and I could taste more and more of her precum. The taste was amazing and if I had known that I would like it that much I would have pursued shemales long before that.
After sucking her cock for a few minutes Amanda put her hands on the side of my head and tilted my head back so I was looking at her face. “Do you want to take this to your bed?” she asked.
I took her saliva covered cock out of my mouth and nodded. With Amanda’s hand in mine we walked through my bedroom door to the bed where she spanked me on the ass and gave me a playful shove onto the bed. Rolling onto my back Amanda came towards me, her hard cock swaying between her legs.
She laid with her body on top of mine and once again found my mouth with hers. Her tongue kissing was passionate and her still wet cock ground against mine. Our cocks slid back and forth against each other as my arms wrapped around her back and pulled her closer. Her breasts pressed against me and her hands held my head while we made out.
Amanda then lifted up off me and took her mouth from mine. Strattling my stomach she kept moving forward on her knees until her cock was right in front of my face. Grabbing a pillow and placing it under my head she smiled at me as I opened my mouth to allow her cock in. Placing her cock head on my tongue she rocked back and forth sliding her cock in and out of my mouth. Amanda had a hand in my hair and after a few seconds she was fucking my mouth in a nice rhythm. I enjoyed this position immensely as I could look up at her face while her cock was in my mouth. From the look of extacy on her face I was more turned on than ever just knowing I could give such a beautiful girl so much pleasure.
After fucking my face for a few minutes she took her cock from my mouth and backed up until my hard cock bumped into her lower back. “Aww, still hard as a rock huh?” she purred. “Let me help.”
She slid down until she was on all fours between my legs and took my cock back in her mouth. Her finger returned immediately to my ass where she pushed it back in. She sucked and licked my cock and then moved down and started licking my balls. She took the first one in her mouth and the switched to the other one. After thoroughly licking each ball she spread and lifted my legs and started licking the path from my balls to my ass.
I gasped as her tongue made contact with my hole. I immediately felt a tingling in my hands and feet as the nerve endings in my ass went into overdrive and within seconds I was moaning for more. She used both her finger and her tongue to give me the most intense anal pleasure I had ever felt in my life. Before long one finger turned into two and although it took some getting used to it also started to feel really good.
Before her second finger entered my ass my only thought had been on the pleasure of what I was experiencing in the moment. After she penetrated me with her second finger I started to think about the possibility of her fucking me. The thought excited me and as her fingers moved in and out and I started imagining it was her cock.
Feeling me wiggle my ass into her fingers, Amanda could tell how much I was enjoying it. Smiling at me she winked and leaned over to pick up the lotion from my nightstand. She squirted some in her hand and rubbed it on her cock until it was glistening in the low light. Gently she removed her fingers from my ass, and rubbed her lotion convered fingers on my hole.
She positioned her cock at the entrance to my ass and looked at me for confirmation that I was ok with what was about to happen.
“Please just go slow, this is my first time.”
She smiled and nodded and then began to press the head of her cock against my hole. Slowly I felt my ass stretch and strain to give way to her thick eight inch cock. I thought her fingers were uncomfortable at first but she would have had to get her entire hand in my ass to prepare me for her monster cock. I almost screamed by the time I felt the head of her cock finally pass the outer ring and pop into my ass.
Amanda exhaled and gave me some time to get used to her cock in my ass. What started out as painful faded to uncomfortable and then to stimulating. After thirty seconds it started to feel good and Amanda slowly began pushing more of her cock in my ass. Little by little with stops and starts she pushed until she had her entire cock in my ass. At first it felt like I had to go to the bathroom but after some time had passed it felt more and more right, like I was finally fulfilling a deep, unrealized lust.
Amanda leaned forward and brought my legs back with her so she stayed firmly implanted in my ass. Once her breasts hovered in front of my face she whispered, “Feel good?”
I nodded and smiled and kissed her with a passion I didn’t know I had. Amanda slowly started fucking my ass while I wrapped my legs around her waist. As the pace of her fucking picked up so did the moaning from both of us. I reached up and played with her breasts while she reached down and started stroking my cock. At first it was a light touch but gradually she got to a pace that matched her fucking of my ass. After all her great oral treatment and the amazing sensation of having my ass fucked I knew I wouldn’t last long with her stroking.
[This story follows the characters and situation started Progressive Dinner. I hope you enjoy this whether or not you also read that one.]
I had left my bag in the room when I checked in, so only Elle’s had to come up with us. I carried it under one arm and hugged Elle with the other as we got into the elevator. As Elle had requested, I got a room on one of the upper floors, the eighth, with a wonderful (and somewhat pricey) view of the river.
As soon as we got into the room, Elle saw the bouquet I had ordered — a showy shower of roses, framing an iced bottle of Mumm’s. When she saw it, she wrapped her arms around my neck, stood tiptoe to give me a big, wet kiss, and whispered, “Ian you sweetie! They’re beautiful.” Her hand on my pants gripped my furious erection and emphasized her appreciation.
She found a bud just starting to open, broke it off with a few inches of stem, and tucked it behind one ear. Then she headed to the bathroom. “I’ll be back in a minute.”
I took the moment to look around the room a little more. This side of the hotel, seen from the outside, had a blocky, ziggurat look to it. The way it was built, each room had a small open porch. The way the building stepped outward, there was only a one-story drop down to the next level, even on our floor. Angles made it impossible to see any porch from any other unless you leaned way out past the railing, so even this outdoor space was relatively private.
I was back inside pouring the Mumm’s when Elle came back out of the bathroom. She pulled some sloping sandals from her bag and put them on. I didn’t look closely, but I noticed something strappy with about a three inch wedge in the sole, a lot more heel than she usually wore. I didn’t think much of it, though. I was too enchanted with by the billowing lapels of her jacket, with shy breasts hiding in the darkness behind them.
I handed her a glass, and said, “To us.”
She answered, “To our first year together!” We clinked glasses and sipped deeply to the happy time. Still holding her glass, Elle hugged me with her other arm. She pressed herself against my erection as she rubbed my thigh between her legs. I cupped her bottom and pulled it close, filling my hand with that gorgeous round curve. We kissed, sipped, and held for a few minutes, until my glass was empty. I set it down so I could attend to her with both hands.
Elle wore a summer-weight jacket and knee-length black skirt — that was all. She had made very sure I knew how naked she was under that. More than naked, really, since she had also shaved her pubis for the occasion. I started caressing her breast through the light jacket. When she unbuttoned it, I accepted her invitation and cupped her bare breast.
I love that feeling. These breasts aren’t ‘perky’ or ‘pert’. Instead, they have the most wonderful softness, the kind that flows into my hand. I caught the nipple in the ‘V’ next to my thumb, and felt its contrasting firmness. Elle sighed and pulled me closer when my grasp tightened.
I kept one hand on her bottom, feeling the muscles flex as she moved, and shifted the other hand from her breast to the front of her skirt. A moment later, my thumb found her mons and started to massage it through the light fabric. Elle pulled a little away from me, pulled her skirt up, and tucked the front into her waistband. She bared her clean, smooth labia to me, and let me see that little pink ruffle that peeked out from between them. I knelt in front of her and kissed. That isn’t a good position for kissing her vulva deeply, but it filled my face with her scent and softness. And, since she had never shaved her pubic hair before, I felt her intimate curves on my lips in a whole new way.
Elle held my head close to her hips. Then she took me by the shoulders and pulled me up. One button at a time, she opened my shirt. At each step, she explored the new exposure with her hands and lips. Those explorations continued downward as my shirt opened lower and lower. I scarcely noticed that she took a step or two backwards each time, backing toward the patio door, until I was almost on the threshold.
“Outside?” I must have sounded more startled than I meant to.
“Why not?” Elle opened my belt as she spoke, with plenty of side trips to the erection leaping under it. “No one can see.”
I looked around. The room lights were off, since the sky still cast enough light through the window wall. Unless someone on the other side of the river had a pretty good telescope, she was right. We both stepped outside and Elle continued opening my clothes. Once the belt was open, my pants yielded easily enough. Elle drew it out, though, lowering the zipper by inches. She left my pants around my hips, but started to lower my briefs as well.
Elle was kneeling by that point, just as I had knelt in front of her. She teased my underwear down just as slowly, exposing my erection and playing with it as each inch appeared. She also cooed little nothings to it as it emerged, “Beautiful penis, big strong guy, you’re happy to see me — I can tell.” Silly stuff, really just happy sounds to bolster the bond between us.
She kissed it as she exposed it, licking the tip, nibbling the shaft, and spreading pre-come into a slick covering. My balls had pulled tight by the time my underwear went that low, as much from excitement as from the cooling sunset. Elle pushed my underwear out of the way by hooking the elastic behind my balls. It was a little awkward getting there, but added pressure just heightened my tension.
Elle stood then, still holding as much of my erection’s length as could fit in her slim hand. She kissed me, spreading pre-come on my lips, too. I don’t know what it is, but tasting myself in her mouth is the most intimate thing in the world. It means she has truly taken me into herself.
Still holding our faces close, Elle whispered, “Ian, I want to feel you inside of me.”
My erection leaped in her hand. “My god, Elle, I want that more than anything. Let me get a condom.” I started to turn away, holding my pants so I wouldn’t trip over them.
Elle’s grip tightened around me and pulled me back. “Not tonight Ian. I want to feel you, just you inside me.” The statement ended with another slow, slippery kiss.
Even though Elle was on the pill, we had always been reasonably careful about safe sex. Elle is a biologist — she wouldn’t have it any other way. I started to protest, “But …”
She hushed my with another soft kiss. “We’ve been together for a year, Ian. That’s longer than I’ve been with anyone before. I trust you, I know you haven’t been with anyone else in that year.” Or in the eight months before that, if you must know the truth. “And,” her voice dropped, “I’ve never felt a penis directly before, not inside.”
If you grew up before the AIDS generation, you might not realize this is kind of a big deal. For lots of people our age, going bareback the first time is right up there with losing her virginity. And, from what I’ve heard of women’s first time stories, it’s often more well-considered and enjoyable.
I hugged her close. I’m sure my erection dribbled pre-come onto her gorgeous jacket, but neither of us seemed to care at the moment. “Elle, thank you. You have no idea what that means to me.” I’ve never whined about wearing a condom. It’s not nearly as bad as some guys make it out to be. I have to admit, though, the few times I had gone bareback before, with other women, the feeling was incredible. I reached down to where her tucked skirt left her exposed and caressed her again. “Let’s go inside.”
Elle pulled against me. “No. Let’s do it out here.”
“WHAT?” She had kept her voice low. I’m afraid I just blew whatever discretion she was trying for.
“Why not?” Her whisper had the sweetest tone, and the most reasonable. “No one’s looking. Even if they did, they couldn’t see below the railing.” She was right about that. The wall around our little porch came waist high, maybe a bit higher. “And it’s nice out here. I want the sky to see us.”
The temperature was just on the cool side of ideal, I had to admit. We both had our tops on, too, even if they weren’t buttoned. The hypothetical observer might be titillated by her open jacket. Even unbuttoned, though, it still covered her breasts. Still, I was a little slow getting used to the idea. “There’s nothing to lie on here.” The concrete floor looked uncomfortable. “And I don’t think the chairs will work.”
“Silly,” she said. “Who needs that stuff?” With that, she turned, flipped her skirt up to her waist, and leaned onto the railing. “How’s this?”
I stepped forward and grabbed her. That pose did the very most for the gorgeous curve of her hip and waist. Her feet stood a little apart, and the lower part of her labia bulged sweetly below her cheeks. My erection slid between her legs in an instant. I hugged her bottom into my lap, leaned over her back and whispered, “You are the hottest thing on earth, you know that?”
She had reached down between her legs in front to grab my erection, and was sliding it between her labia. “Tell me about it.”
As she had done with me, I started murmuring happy sounds in her ear. I’m not sure what I said. I’m not even sure it made sense. It probably didn’t. She rocked her hips to slide my erection between her labia, giving me the most incredible feelings. At one point, she pressed back and tipped her hips way up. She played with her clitoris, using me as her toy. That didn’t make for the most coherent conversation. It didn’t matter. Only the voice mattered, hers or mine, regardless of what it was saying.
Elle pulled way forward, off my penis. Then she reached back with both hands, her chest on the railing, and opened herself. “Come inside me, Ian. Please.”
I forced myself to go slowly, making sure she was slick enough inside for comfortable entry. I forced my own responses to a slower pace, too, or I would have come when I got the first inch into her. We slid together easily, though. Elle shifted her hand to my erection once I made it between her labia and she guided me farther in. That’s when I realized what those sandals were for. They lifted Elle’s pelvis a few inches, so our heights nearly matched. Even though she was shorter than me, I didn’t have to scrooch down to her level to enter her, or only a little. I should have known. Everything Elle does, she does for reasons.
As I said, I never minded condoms all that much. This was heaven, though. That tiny difference in the feeling between us made a huge difference. I pressed until the tip of my erection opened that ring of muscle at the edge of her vagina. That barrier that seemed to define ‘inside,’ and I was past it. I held for a moment, savoring the sensation. Elle seemed the impatient one, though. Once her body had a solid hold on me, she let go with her hand and pressed back toward me. She wanted me deeper inside, just as much as I wanted to be there.
I held Elle’s hips firmly and pulled her close. Her round bottom, her skirt bunched at her hips, our point of union — well, it was the sexiest thing I had ever seen in my life. And, although I knew in some intellectual way that no one could see us, the last of the sunset and the sliver of moon made me feel naked to the world. I suddenly realized what Elle meant. I wanted the world to witness us together like this, with our human and animal selves merging as Nature meant for them to.
I was soon in Elle to my full depth, as much as our standing position allowed. We developed an easy rhythm, with her moving on me as much as I moved in her. Once that reached a comfortable pace, I leaned forward. I put some of the weight of my chest on her back and brushed the lapels of her jacket away. Elle’s magically soft breasts swung as we moved. They’re not big, a luscious B if I remember right, but their softness meant they dangled low. I collected one in each hand as I lay across her back, and gathered them close to her chest.
My movement at that point consisted mostly of bucking hips. I rocked and thrust into her, my movements getting sharper and stronger. Still holding her breasts from behind, I locked my elbows on her hips. That let me pull her back onto me, hard, and her own movements grew stronger with mine. I almost whispered, ‘Elle, play with yourself,’ when I realized I could feel her fingers working near where our bodies joined. Instead, I grunted, “Elle, I’m going to come.”
I held her against me harder than ever, rocking almost out of control against her. Our thighs slapped together, the backs of her against the fronts of mine, then I tugged hard. I pulled her strong, sleek waist against my stomach. I grasped her breasts closely, feeling lush softness yielding to me. I pressed my cheek against her back, feeling sinew and bone respond to my urgency. I felt her huge, deep, feminine power accept my strongest thrusts, absorb them, transform them into deep caresses. I poured myself into her with a few last spasms, then held her hard until my orgasm released me.
Before that happened, however, Elle’s whisper took on a desperate tone. “I’m coming too, Ian. Hold me. Hold me. Ho …” The words vanished into a squeak. Elle can be loud, but bit the sound back. I felt her hip buck back against me, rotate, and shift, so she swirled my erection inside her. I was too caught up in my own orgasm to follow what she did, but gave her body all the pressure and power I could offer. More, there always seemed room within her to absorb more of my strength. The more she absorbed, the more her body wracked with orgasm.
My peak passed just as hers arrived. I held her close, grasped her waist between my arms, found nipples between my fingers. Her knees buckled, but tension in mine was there to support her. Eventually, her bitten-off moans quieted. She slumped onto the railing, all at once, like a puppet with the strings cut. I held her close, feeling my fading erection withdraw from her, and mumbled loving things about beauty, her body, and womanly strength.
It seemed as if the last glow of sunset faded with the last glow of our orgasm. Quiescent, my penis could barely touch her vagina, let alone fill it. I released her breasts and brushed her lapels somewhere near her chest. I smoothed her jacket. I found the edge of her bunched skirt, and pulled it back over the most beautiful hips in the world — after a kiss goodbye for each one.
Elle just rested against the railing while I pulled my pants back up. I buttoned, zipped, and buckled. All the while, I tried to keep one hand on her waist, or at least my lap against her back side.
When I was done, Elle stood. She un-tucked her skirt from the front and arranged it around her. She was adjusting the light jacket around her bare breasts when I came close behind her and put my arms around her waist. She took one of my hands in each of hers, pulled them tighter around her, and leaned back against me. She looked up with a dreamy gaze. “The moon saw us.”
“Elle, the river, the bay, and the sunset saw us. The world saw us. They made a beautiful place for us.”
“They did. I think we used it right.”
She rocked a little as she leaned against me. It felt almost like a slow dance, one with no music. After a few minutes, she turned to face me. She wore a huge grin, and reached over to kiss me (the heels made us even, pretty much). After a quick kiss, she pressed a cheek to mine and hugged me close. She whispered, so I could barely hear, “Ian, you’re leaking out of me.”
Chivalrous instinct took over before thought. “I’ll get some tissues.” In truth, I could do with a wipe, too.
She wouldn’t let go. “No, silly. It’s OK. I’ve always used condoms so I never felt it before, just a little of my own wetness. This is what real fucking feels like. It’s happy and it’s sloppy. This is part of it.” She leaned into me again and rocked. I have no idea what that meant, but she was happy so I was happy.
“I don’t want to leak on the floor, though.” Elle backed away. “I’ll be back in a minute.” She went back into our room, kicking off the heels on the way in, and worked her way to the bathroom. I collected myself while she carried out her feminine mysteries. I got the shirt buttons aligned with the right holes, and got myself looking as respectable as ever.
Elle almost skipped out of the bathroom. Her flat shoes were still near the door, so she slid them on. “Let’s go dancing.”
Why is it that sex puts men to sleep but gives women so much energy? I rallied myself, stoppered the wine, and headed toward the door with her. I checked in the mirror before I left, and checked her, too, for dribbles on our clothes. I didn’t see any on me. As I suspected, a snail-trail of pre-come marked the front of her jacket. I pointed and started to say, “Uh, Elle, …”
She looked down and fingered the damp trail. “Oh. Can’t have that, can we?”
Elle took the jacket off and hung it up, leaving her gloriously topless. Her breasts bobbed and swayed as she walked over to her bag, rummaged in it for a moment, and retrieved a black camisole, one with lace trim and spaghetti straps. She pulled that on, turned to me, and asked, “How’s this?”
I’ve never seen her look better, at least not with clothes on. The skirt showed off the curve of her hip, the minimal top showed the slim grace of her upper body, and her braless state caused a mouth-watering jiggle with each motion. Friction against her top seemed to bring her nipples to life, too. “That’s the kind of clothing you put on just so I’ll rip it off, right?”
“Maybe later.” Elle took my elbow and we went out.
If we had been alone in the elevator, her skirt would have been around her waist again in a heartbeat. I was vividly aware of her nearly-naked state, just one hemline away. The scent of sex around her kept me in a permanent state of erection, too. Instead, I contented myself with standing in the back and groping her bottom, where no one else could see what I was doing.
When we got to the lounge, I suddenly realized just how much I had had to drink that day. It had been well spaced out, with plenty of food to go with, but added up to a fair bit. I ordered just a club soda with lime, and Elle did the same. When the next slow tune came up, Elle pulled me to the dance floor. I’m not much of a dancer. I do it for Elle, though, and she puts up with how bad I am. We alternated, munching the bar peanuts and sipping club soda, then joining about every other dance. On the second or third, Elle flashed an I’ve-got-a-secret smile and said, “You’re leaking out of me again.” Then she leaned against me, so I could feel her warm breasts against my chest, leaving me to imagine just what was going on at her shaven pubis.
“God, girl, you give me the biggest erection just thinking about it.” I kept my voice low, for her only.
“You say that like it’s a bad thing.” She continued the conversation just as quietly.
“Not bad, not at all, but it’s going the wrong way down my underwear. That gets uncomfortable.”
Were other couples having these conversations on the dance floor? If so, it’s the closest I’ve ever been to an orgy.
“Ohh, poor baby.” Elle pressed against me. I’m sure she could feel it aimed down my leg. “When we get back to the room, can I kiss it and make it better?”
She must have felt it twitch at the thought. “Yes,” she said, “that’s what I’ll do. I’ll take good care of the little guy. I’ll hold him and kiss him and make him all better.”
“Hey, pretty lady,” I answered, “are you trying to get yourself fucked again, right here right now?” I held her hip close to mine and rubbed my erection against her.
“Hmm,” she answered, “let me think.”
A dance or two later, the long day caught up to both of us. On the way back to the room, we had the elevator to ourselves. I grabbed her for a juicy kiss. While I was holding her, I worked her skirt up so I could hold that lovely smooth butt with both hands. I pulled her close, my erection between us, and almost came in my pants. I dropped her skirt when the elevator slowed, but kept my hand on her butt all the way back to the room.