Jessica's First Time

I watched as you came toward me down the airport corridor. I recognized you right away from the pictures you had sent me, but you were not yet able to pick me out of the waiting crowd. I took the opportunity to observe you from a distance, to see how you walked, how your body moved, how your dark hair bounced with every step you took. I saw the subtle movements of your full breasts beneath your blouse, the seductive movements of your hips. This brief first glimpse of you was enough to make my cock harden with desire. You were just as beautiful as I had anticipated, and my thoughts turned immediately to undressing you and exploring all your hidden charms.

For a moment I lost sight of you as you dodged around the security gate, and then as you re-emerged, you spotted me, my full beard making me easy to identify. Your face erupted in a bright smile of greeting, as you strode toward me. You reached out your hand and I took it in mine. A shiver ran through my body at our first touch. I had been anticipating this moment for weeks, and now you were finally standing there before me. I was thrilled beyond words, but I did manage to stammer a few words of greeting before I released your hand and led you toward my car.

We chatted easily as we claimed your baggage, walked to my car, then drove to a nearby restaurant. I was tempted to drive directly to the motel so I could rip off your clothes and fuck you until you screamed for mercy. My raging cock told me that was the perfect choice. But I wanted our first time together to be special, to be memorable, to be a totally pleasant experience that we would both treasure forever. So I resisted temptation, but only barely.

The restaurant turned out to be the right choice. We had a nice corner booth, and I was seated across from you. Because of our extensive email correspondence and recent phone calls, we knew a lot about each other already, and we talked easily. You smiled often as we talked, and your dark eyes sparkled as you recounted events from your past and plans for your future. Your voice was melodic and entrancing, and I found myself getting lost in your words, your eyes, and your smile.

We had wine with our dinner, because I thought it would help us both relax, but as the meal progressed, I saw that I should not have worried. We were both totally relaxed from the beginning, like two old friends who were catching up after not seeing each other for several months.

We ate lightly—appetizers and salads—because we both knew what the coming evening promised, and we did not want to be encumbered by a heavy meal. After our final glass of wine, I rose, took your hand, and led you toward the parking lot, toward our motel, toward the bed where you would finally lose your virginity.

Our top floor suite was large and comfortable. The bedroom looked out on a wooded tract which meant we could leave the curtains open without concern for being seen. The king sized bed just begged to be mussed, but that would come soon enough. We took a few moments to settle in, to freshen up, to get comfortable in our new surroundings. When you emerged from the bathroom, I could tell that you were now a little nervous, all your uncertainties and concerns suddenly rising to the surface. I moved toward you and took you in my arms. I held you close. I could feel the pounding of your heart against my chest. Your warm, rapid breaths caressed my neck. I felt your body begin to relax against me.

"Trust me. Relax and trust me. You will be fine. You will do fine," I whispered in your ear.

I began by kissing your neck. You shivered slightly at the feel of my lips on your bare flesh. I kissed up to your hairline, then over to your ear. I kissed your ear and gently nibbled on its lobe.

"Close your eyes," I said, as I kissed you gently on your forehead, your eyelids, your cheeks, your nose, your chin, and finally your lips. I kissed you softly at first, caressing your lips with mine, while at the same time pressing my body firmly against the contours of yours. Eventually I slipped my tongue between my slightly parted lips and stroked your lips with its tip. In response, you parted your lips enough for your tongue's tip to emerge and toy with mine. Soon, we were engaged in a long deep kiss with our tongues entangled like two serpents intent on entrapping each other in their coils. It was a marvelous first kiss that signaled the promise of the evening to come.

I stepped back away from you. "Keep your eyes closed," I said. "And just focus on my touch. Think of nothing else. You are here with me. This is where you want to be. Relax, Jessica. Relax."

I began unbuttoning your blouse as I stood before you. I moved slowly, top to bottom, as I watched your face for any changes or responses. As I worked my way down, I intentionally allowed my fingers to slide over your skin where possible. I softly stroked the breast flesh that spilled from the top of your lacy bra. I glided my fingers across the smooth skin of your tummy and down to the waistband of your slacks.

I unbuttoned your slacks and slowly slid them down your legs and with your help I removed them and tossed them aside. At this point I was kneeling before you. I leaned forward and kissed your tummy. I kissed down the front of your leg and then along your inner thigh. I extended my tongue and licked up between your thighs toward your pussy. You tried to pull back, but I took your ass in my hands and pulled you toward me. I kissed your pussy through the fabric of your panties. You moaned softly. I used my teeth to nibble on your lips and clit, gently but suggestively.

Although I had not intended to touch your pussy at this point, I could not resist. I used my fingers to pull aside the fabric of your panties. I moved forward and licked your gorgeous pussy from top to bottom. You moaned again, louder this time, and your hips involuntarily trust your pussy against my tongue. You tasted sweet and delectable! I sucked your clit between my lips and nibbled on it gently with my teeth. You moaned again. I looked, and your eyes were still closed as I had instructed. Although I wanted to spend more time exploring your pussy, I knew that there would be plenty of time for that later. Still kneeling, I slid your panties down over your hips to the floor then cast them aside.

I stood again, facing you. I kissed your lips and this time you responded immediately, your tongue seeking out mine unhesitatingly. As we kissed, I unfastened your bra and slowly released your full breasts. I pulled away from you for a moment so I could remove my shirt, then we resumed our kiss as your breasts pressed against my naked chest. I felt your nipples grow hard.

"Jessica," I said. "Do you realize that you are standing naked before me?"

"Yes."

"And do you like being here naked with me?"

"Yes."

"Good. Well fold down the covers while I get undressed."

I watched as you bent at the waist to fold back the covers. Your pussy peeked at me between your thighs. I smiled at the thought of fucking such a beautiful cunt for the first time.

You sat on the edge of the bed and watched me remove my shoes, socks, and pants. I stepped forward and stood before you wearing only my briefs.

"I want you to remove my briefs and expose my cock. Can you tell that you have already made it hard? Can you see its outline? Can you tell I am ready to fuck you, Jessica?"

"Yessss," you said softly. And with that, you reached out and carefully slid my briefs down my legs. My cock, freed from its constraints, stretched out toward you, pleading for your attention.

"Take my cock in your hands, Jessica. Feel how hard you have made me. That's it. Now kiss its head. Yes, that's it. Now use your tongue to lick the tip. Oh, yes. Now take it in your mouth, Jessica. Suck it in. Yes, so good."

I put my hand on the back of your head and began pumping my cock slowly into your mouth. At first you seemed hesitant, even reluctant, but within moments you were taking my cock deep inside, your tongue dashing and darting all over its surface, your mouth slurping as my cock pistoned within you.

I loved the warmth of your mouth on my delicate flesh. I could feel your lips pressed tightly around my cock, and occasionally I could feel your teeth slip along its length. Your tongue played rapidly over and around my cock and its tender head, and soon I was on the verge of cumming, but that was not part of my plan. Reluctantly, I pulled away. You looked up at me with a look of disappointment.

"Later, baby. Later. There will be lots of time for such things later."

With that I pushed you back onto the bed. You wriggled your body up so that your head was on the pillows. I moved toward the foot of the bed, and used my hand to spread your legs. You moved your hand to cover your pussy, but I reached out and removed it and placed it at your side.

"There is nothing to be shy about with me, Jessica. Do you understand? I love everything about you. You have beautiful breasts, an incredible pussy, and a wonderful body. You have no need to hide from me. Just relax. I want to touch you and bring you pleasure in ways that you have never imagined. Do you understand?"

"Yes, I will try."

"That is all I ask."

And with that, I leaned forward and planted a kiss on your clit. Your body jumped at my touch. I sucked your clit between my lips and caressed it with my tongue. Your hips twitched involuntarily. For the next several minutes, I explored every part of your dark-skinned pussy with my mouth and tongue. I nibbled on your clit until it became overly sensitive and you pushed my head away. I sucked each of your engorged lips into my mouth and nibbled on them with my teeth and teased them with my tongue. I moved my tongue between your lips and teased the crimson opening to your inner recesses. As I did so, you reached down and grasped my head, pulling my tongue farther into you. For a moment I fucked your pussy with my tongue, causing you to spread your legs wide apart and pump your pussy against my face. Your juices were flowing freely by this time, and my face was soon glistening with your essence. You were quickly losing your shyness, I thought to myself.

"I am going to fuck you now, Jessica," I said, as I slid my body up over yours.

"No, not now. I am not ready. Maybe later. Maybe this is not the right time."

"This is the right time. And I am going to fuck you now, Jessica. You know this is what you want. You know this is why you flew across the country to be with me."

I had suspected that that you might get cold feet at the last moment, and I was prepared. I shifted my position and grabbed one of the wrist restraints that were concealed at the corner of the bed. I had it in place before you could protest, and the second one soon followed on the other wrist. With your upper body restrained, it was easy to attach the padded cords to each of your ankles.

I knelt between your spread legs and looked at your face. There was a morsel of fear there, I could tell, but most of what I saw was lust, passion, vulnerability, all blended in a witch's cauldron of need and desire.

"Oh, fuck me. Yes, fuck me. I am helpless. I can't defend myself. Do with me what you will. Fill my pussy with your cock. Oh yes, fuck me, fuck me, fuck me now. I can't wait any longer. Oh take me anyway you want to, just do it. DO IT!"

With that I positioned my body over yours. I braced my hands beside your head and placed the head of my cock at the opening of your pulsating pussy. I felt your body quiver beneath me. I used one of my hands to moisten my cock with my saliva, because I knew that your virgin pussy would be tight and hard to enter.

I pressed forward slowly, lodging the head between your swollen lips. I pushed forward slightly, and I immediately encountered resistance. Your tight pussy refused to allow me admission.

"No, please. No. I am not ready. You can't do this to me. I am too tight. Don't hurt me. Ooooooh! Push! Yes! Hurt me! Fuck me! I want your cock inside me. Oh, yes. I w-a-n-t y-o-u-r c-o-c-k i-n-s-i-d-e m-e. Yessssss! Nooooooow!"

You were mumbling almost incoherently with pent up need and desire now. You did not know where you were or who you were with, and you did not care. All that mattered was having a cock inside you. After decades of dreaming, imagining, fingering, picturing, you were here and you were ready to be fucked. Your entire body quivered with anticipation as the moment approached. I was afraid that you might faint away, and then I would have to decide whether to wait until you recovered or whether I should press forward.

And with that I pressed forward again. The head of my cock forced apart the tight muscles of your cunt, and the head popped inside. You screamed out, so I knew that there was some pain involved. I held still, giving your body time to adjust to this invasion of your hidden recesses. I relaxed and allowed my body to press down on yours. Your hard nipples poked against my chest. I kissed you, hoping that I could divert your attention from the pain my cock was causing.

It was a marvelous kiss we shared, a kiss unlike any other. We kissed long and hard as our minds and bodies searched for that innermost connection, that baring of souls, that giving of trust that comes when two partners find one another in some special moment that is perfect in every way. Our tongues twisted and twined as we kissed with a mounting passion that soon stirred our loins.

I felt you move beneath me as our kissing grew more intimate, and I sensed that you were trying, instinctively, to maneuver into the perfect position to allow me to penetrate more deeply and to fill you completely. You twisted your hips and raised your ass in multiple combinations, until finally, I could feel your pussy relaxing and my cock sliding slowly up inside you. You thrust your body upward then as your pussy stretched around my erection and you felt, for the first time, the marvelous sensations created by a hard cock stretching a willing pussy. You moaned loudly in the midst of our kiss, and I knew then that all would be fine.

I rose up off of you and supported myself with my arms. I looked down into your face, your beautiful face, because I wanted to watch as you enjoyed your first fuck. I wanted to see the release that came with that fuck, both mental and physical release that had built up over years of frustration, guilt, anxiety and despair. I wanted to see the sheer joy that you would experience as you climaxed for the first time with a man rather than with your fingers or with a toy.

And with that, I began to pump my cock into you. Slowly and gently as your body gradually became accustomed to the invasion of my cock, then harder and faster as your pussy relaxed and grew used to the multiple sensations associated with being fucked. At first you remained still beneath me as your body adjusted. But soon, you were moving beneath me, bucking your hips, trusting against me in rhythm to take me fully inside you on every stroke.

I watched your face as it went through many transformations. In the beginning there was a softness that came with willingness, a tenseness that came from the fear of pain, the set jaw of determination that said you were not going to let this opportunity pass. With each thrust, your features softened, became more primal, more sensual, more animalistic. As your body relaxed and admitted me fully, your features changed once again. Every muscle of your countenance became relaxed, your jaw dropped and your mouth fell open as if you were trying to speak but no words came, your nostrils flared rapidly, and your eyes glazed over in a way that I have seldom seen. Your entire being was now focused on your cunt and the feel of my cock inside of you and the glorious sensations that this link was stirring in your loins and that were spreading through your body.

I used one of my hands to free your hands from their bonds, and you wrapped your arms around me, kissed my neck, and used the leverage to pump your lower body against mine. I was no longer fucking you; you were now fucking me for all you were worth. Moans that emanated from deep within you filled the room as you pumped against my cock. The smell of your juices spread out around us and spurred us to a higher passion. Your moans became elongated, wild screams as your climax approached. Those in neighboring rooms must have wondered what kind of wild, deranged animal was locked in the room next door.

When you came, you screeched—a long, drawn out screech of pent up emotion and desire that was finally fulfilled. Your body was wracked with multiple convulsive thrusts that caused my cock to pound against your cervix deep inside you. The smell of your juices, the sounds of your climax, the convulsing of your pussy around my cock were more than I could stand. I came hard, my moans mixing with your screams to fill the room. I shot my cum deep inside you, coating your cervix, filling you with my love and passion in a powerful orgasm that convulsed my body with tremors of intense pleasure.

I collapsed on top of you to catch my breath. Your arms, still wrapped around me, held me tightly against your chest. As I labored to breathe, I heard you sobbing beneath me. Thinking that I was hurting you, or had hurt you, I raised up off of you. I looked down at your face, but you did not attempt to hide your tears. Your eyes were red, and tears were streaming down your face.

"Did I hurt you? Are you ok? Do you want me to get off of you?"

"No, don't you dare move. Keep your cock inside me as long as you can. That was wonderful. Amazing! How could I ever have imagined anything as wonderful as that? Thank you. Now—can we do it again?" you added with a sly smile.

And I assure you, we did it again and again, in every conceivable position and in every orifice, until we were finally worn out and had to sleep. So that is what we did. We slept with your head on my arm, your lovely body nestled against mine. We slept the sleep of contentment and exhaustion that lasted until you woke and sought out my cock and I was awakened by the grasp of your lips and the caress of your tongue on my growing erection. And then we began again.