Category: Anal Stories

Two Firsts

by Clarence©

"Fuck me, fuck me, FUCK ME," Jackie screamed, as she thrust her hips hard upward, into Michael's descending pelvis. It was some combination between ecstasy and agony that drove her to this new heightened level of aggression. This man was moving in and out of her, charging into her inner-most depths. He was stretching her to capacity, ravaging her to her very soul. The desperate aching in her loins was almost too much for her to bare as she fought her way toward an orgasm, the intensity of which was sure to far surpass anything she had yet experienced.

With each thrust, each movement, it felt as though all of her body's telekinetic energy, all of her life blood were being summoned to this mecca of soft skin and sweet moisture, this epicenter of nerve endings that she harbored between her now tense and shaking legs. She ground herself into him, attempting to extract her climax from this man's hard, thick member, dividing her at this junction of heaven, where two legs come together to form that which is most woman.

Even if she had wanted to stop thrusting, she would not have been able. Her most primal urges had taken over completely. All thoughts of etiquette and courtesy were completely flushed out of her mind. Even her command of the English language had been reduced to shouting obscenities. Her finger nails dug into his backside as she tried to pull him further, deeper into her most sacred of places.

He was in as far as he could go. He filled her up completely, stretching her on all sides, yet she kept pulling him in. It hurt to have him pressing against her, stretching her insides, but she could not stop herself. She needed this pain. The glowing sensation in her crotch was making itself more and more known by the moment.

This new kind of arousal was as strange as it was mind-blowing. In the past she had always yearned to feel some kind of arousal, any kind at all. When she had had orgasms they had felt good, but they were nothing to scream and yell about like those girls on the videos.

She had always suspected that these movies were strictly for men who had never been with a woman before. She reasoned that any man who had actually had sex with a female would know that women didn't react like that to sex. Now she was learning how wrong she had been. This new form of intense arousal was so consuming it even scared her a little. It wasn't that it made her want to stop. It was that it made her never want to stop. It instilled her with the feeling that that this feverish and frantic arousal must be satisfied, and that friction, friction was the answer. Pressure, rubbing, pushing, grinding, fucking. These must be the things that would appease her growing urges.

Everything in her lower half told her that the way to alleviate this pleasant misery to was heave herself against him with that all she had. Every time she did so It felt, at first, as though the arousal was being satiated, but if the rubbing and pushing subsided only for the moment, she felt even more desperate than before. All she could do was have faith that her orgasm was coming, for if it was not she didn't know what she would do

She was a slave to her own lust. Her mind was no longer in any sort of control, whatsoever. This was a kind of arousal she had never known. Orgasm was the only thing she cared about now. It was the only end that made any difference to her. She arched her back and took him in as far as she could. Every nerve was alive and responding to their communal, frenzied movement. She was being driven forward by a force she did not recognize, nor was it something she could control.

"Oh my God. Oh Jesus," she thought to herself. "I am almost there, I'm almost there, I'm almost there!" There was no stopping her. The intense craving for sexual gratification that had been pulsating in her engorged and dripping vulva had now permeated her entire body. Her fingers and toes tingled with every movement, every breath, every sound. "Oh, oh, oh my Holy God, fuck! Don't stop Michael, oh please don't stop! Don't you dare FUCKING STOP!!" It was somewhere between the most desperate plea and the most dictatorial command. She couldn't have cared less. At this moment she was a woman without conscience, without external cares, she was a female beast indulging in the most precious gift nature had provided.

Michael's thrusts grew faster and harder. She would be sore the next day, but telling him to slow down now was out of the question. It felt too wonderful. The feeling began to well up inside her, building slowly but surely. She could not tell him to stop anymore than she could make her heart stop beating. She knew he would if she asked, she just didn't want to ask. The sensation was more intense now. It was beginning to envelope her, to consume her. It was coming fast. She was so close. Her breathing changed from deep and heavy to short and frantic. Her ability to use coherent words and sentences for the purposes of communication was now completely gone. The only sounds that escaped her lips took the form of short, hard moans.

"Oh, uh, uh, ahhh, oh…" she was so close now. The feeling between her legs was so strong she could barely see. She grabbed his muscular ass and pulled him into her with all of her strength and then some. She could feel her climax on it's way now. While the only sounds to escape her mouth took the form of moans and short breaths, inside she was shouting to herself, cheering herself on.

"Uh, uh, come on, you can do it. Your, oh, almost there, oh God, oh God, yes, oh here it comes, here it--


"What are you doing?!"

My girlfriend is standing in the doorway. Although I can tell she is trying to look mad, there is hint of amusement that she can't quite conceal. As I sit at my computer, fully erect penis in hand, I quickly losing all interest in "Jackie and Michael's Rendezvous," an epic which, until just a few seconds ago, had my complete attention.

"Umm…" I stammer.

"So this is what you do when I leave town?" She says. I'm still in panic mode. I'm sure that my face is beat red, and frozen in a mixture of fear and embarrassment.

"Umm… I thought your flight took off at 11:00 am.," I say. Great. Good cover, Josh. Not that you can really cover anything when you get caught red-handed masturbating to Internet porn.

"It got delayed." Was all she said.

Now it's not like Anne is a regular polly-perfect or anything. The two of us have, on many occasions, watched and read porn together. It's something we both enjoy. It isn't getting caught by her that makes me so uncomfortable. It's simply getting caught. As a teenager I used to go online and look at porn at my mother's house. Because she got off work at different times depending on the day of the week, it was not always possible to predict exactly when she would show up. More than once I found myself frantically closing pop-up windows and opening my email to the sound of footsteps coming up the stairs. The point I am trying to make here is that getting caught was a constant fear of mine. And now, so many years later, this fear is being realized, although instead of my mom standing in the doorway, it is my girlfriend.

"Delayed?" I manage to squeak out. I look at the clock at the corner of my screen. 11:23. Damn. She should be on that plane right now. It's not that I would rather have the Internet than my girlfriend, but if she were on the plane then she wouldn't have just caught me doing what I as just doing. My penis, now shrinking and soft, sticks flacidly out the fly of my boxers. With a feeling of utter helplessness, I wait to see what will happen next.

I can tell by the flush in her cheeks that she's a little turned on by what she's just seen. Still, I'm very uncomfortable about the whole situation, and it is obvious who has the upper hand. There is a little bit of slipperiness on my right hand due to my enhanced state of arousal. A few seconds ago it had been bringing me a good deal of pleasure, allowing my hand to slide freely around the head of my cock. Now this slipperiness just feels awkward and sticky. I go to wipe it off so I can close the window on my screen when Anne comes over to me.

"Not so fast, kiddo," she says, "let's see what was so good that you didn't hear me call to you three times from downstairs." Three times? Jesus. I was even more in to that story than I thought. Anne sits on my lap, facing the computer. Her legs dangle on either sides of mine, and the stiff denim fabric of her skirt slides up until most of her thighs are exposed. Without thinking, I reach down to caress them.

"Whoa, easy big fella." She says. Perhaps she is referring to the stroking of her legs. Perhaps she is referring to the fact that, upon feeling her ass, covered by a pair of soft silken panties, my cock has started growing and hardening once again.

"Sorry." I say. I just sit in silence while Anne reads.

"Oh, Jack, you feel so BIG!", she says, mockingly. She's making fun, but I can tell she's starting to get into it. I continue to rub her thighs, and I begin kissing her right shoulder blade. She lets out a soft moan in spite of herself, and I begin to think that perhaps this isn't such a catastrophe after all. As she reads on, I wrap my arms around her stomach, just barely brushing the bottoms of her breasts with my thumbs. As I move my hands from her stomach to her back, she begins moving her ass in little circles around my lap. This feels incredible, and I quickly unhook her bra and place my hands on her soft, firm breasts.

Soon she is reading the story out loud, the mocking sound completely gone from her voice. As I hear her recount the occurrence of sexual intercourse between Jackie and Michael I realize that not only is she moving her hips, but now I too am grinding myself against her butt, pressing myself into that silken paradise, under which lies the soft flesh that crave so deeply. Next, she reaches up to where my hands are caressing her breasts. She takes my right hand and leads it down, past her waist line, and presses it against the thin strip of cloth that covers her. Oh, she is so warm. As I press against her, moving my hand in little circles, up to her clit, and down along her vagina, I feel the cloth of her undergarments beginning to saturate with her warm, soft moisture.

"Mmm," the noise escapes her lips as I gingerly play with her inner thighs. I move my hand from one to the other, just grazing over her clitoris with each pass. This causes her to rock her hips just a bit more vigorously, pressing her ass into my crotch over and over. She takes my left hand to her mouth, and gently licks. First just one finger, than two. Eventually she takes my middle and ring fingers into her mouth completely. This forces me to stop what I am doing, and just sit there in ecstasy for a few seconds.

"Oh, keep going," she mews. I take my fingers from her mouth, and her inner thighs, and reach for the sides of her panties. She presses her shoulder blades into my chest, and arches her back, lifting her rear-end from my lap so that I can remove the constrictive material from hers. She stays in this awkward position long enough so that I can remove my boxers as well. After a bit of wriggling and squirming, she settles back down onto me. Her now completely bare ass is resting on my lap, with my incredibly hard cock sticking strait out beneath her so that it pokes out in front of her, just under her hot, wet pussy.

She reaches down and takes hold of my cock. Gently pulling it up, she rubs my tip against herself. This causes us to let out a simultaneous "Uhhh…"

"Ohhhh, we can't do this," I say.

"I know," answers Anne, "but I want it so bad, I need you inside me."

"We're out of condoms," I tell her. This really doesn't matter. Even if there were fifty condoms sitting on my dresser, neither of us are about to get up from this most heavenly of positions.

"Touch me," she says. I reach around and again begin playing with her, only this time I can place my fingers inside her, and rub them directly over her spongy, swollen clit.

"Oh Josh… Oh Josh…"

"Let's just do it," I say.

"No, you're right," she says, "we can't, we can't." I reach up and once again and touch her breasts, but this time I squeeze them hard, and pull her into me. As I touch her, her hands travel down to her own warm moist opening, to take over where my fingers had left off. As I caress her tits and bite her neck, I hear the warm, wet sounds of hurried fingers going in, and out, and around. Judging by the noise alone I can tell that both her hands are in on the action. Then she does something that feels so incredible I almost come right here and now. With both hands slippery and wet from the joys of self gratification, she reaches down and begins to stroke my dick in slow, steady precision, from tip to base, and back again, up and down, up and down. It feels so amazing. As she strokes me, she is getting more and more in to it, too.

"Mmmm, I gotta go on the pill," she says.

"Mmmm hmmm…" I reply. It's the only response I'm capable of formulating at this particular point in time.

I'm so curious what she feels like inside. I mean what she really feels like, without a condom. She feels incredible even with a thin layer of latex to deaden the sensation, but I can only imagine what it must be like without. As I get more into the fantasy, I begin to really imagine that her juice-soaked hands are actually her vagina, that she is stroking me with her womanhood, and not just the moisture that she has borrowed from there. The more I fantasize, the more real it feels. I'm on another plain of existence. One where we don't have to worry about pregnancy, and I slide freely in and out of her warm, tight vagina for hours on end…

She's stroking harder and faster now. I must admit that in my state of intense arousal it really does feel as though I am penetrating her, and not just her hands. She is moaning and grunting, and jerking. She grabs my legs, digs her nails into them, and continues rocking back and forth. It feels so real, so much like we're actually… Wait! She's holding my legs, one in each hand. She's rocking back and forth on my lap. She's fucking me! We're actually doing it. I was getting so into my fantasy that I didn't notice her lose control and bury me deep into her. Oh, my God! The realization that I am finally having her in all her radiant beauty nearly sends me over the edge yet again. I grab her hips and start pulling her in, and pushing her out. We are both panting and heaving, I can't stop.

"What…are…we…doing?" I manage to get out.

"Ohhhh honey…" she says, "you feel so good inside me. You feel so good inside me."

"No," I say, "we can't do this." It was the most incredible feeling I had ever felt, but I don't want to have to worry about kids. I reach my arm around her waist, and lift her off of me. It almost hurts, not having that amazing sensation anymore, but I know it's the right thing. Then I get an idea. I hold her up with the one arm, and with the other, I take my cock, and slide it up and down her ass crack, taking time to linger at her small puckered hole. I eventually stop there, and place the head of my dick so it is just resting at the entrance.

She starts to say something, until I quickly take my hand off my propped up cock and, leaving it pressing against her anus, move my fingers around to attend to her still throbbing clit, which has been grossly neglected over the last few minutes, all the while supporting her with my other arm. With this she lets out a long deep 'Ohhhhhh', and begins to sit down on my cock. At first it doesn't feel like I will be able to fit inside. I continue to fondle her clit, making sure that it pokes just in between the tips of my middle and ring fingers. She moans, and squirms from my touch, and it feels so good just having her sitting on me like that, with my cock just poking at the entrance.

It becomes obvious that pretty soon I am going to explode all over her hole before I have a chance to get inside. I mean, hey, I just had my first experience with condomless sex, and now, if I can only hold out, I'm about to have my first experience with anal sex. You'd be excited, too. I keep rubbing her, and she keeps squirming on me, and I can feel my orgasm building. I can't stop it. I'm not coming yet, but I know I will soon. And then, it happens. She relaxes and I slide in, all the way in. Oh, I can't even describe the sensation. Once inside her I begin furiously rubbing her clit, as I want her to get to climax with me.

As I rub faster, she squirms more and more until I know I won't be able to hold back any longer, and I just let go. I have the most intense orgasm, that lasts for about ten seconds. I feel myself stiffen as I pump spurt after spurt of semen inside of her. I feel dirty, and incredible, all at once. At exactly the same time I hear her call out my name. Now, she stiffens, and digs her nails into my thighs, while I rub her clit faster than ever before. As I touch her, and with my cock still buried deep in her ass, she comes to the most all-consuming orgasm that I have ever seen.

We sit like this, with me still inside her, for a few minutes before she finally gets up, and I slide out, soft and satisfied. She too, has a look of utter bliss on her face.

"That felt incredible," I tell her.

"Mmmm hmmm," she agrees, "thank God for flight delays.

Written by: Clarence

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Story Tags: experience anal, digs nails, seconds ago, intense arousal, middle ring, hear call, ring fingers, feels incredible, back feels, mmmm hmmm

Category: Anal Stories