My First Time with Jack


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I could feel Jack’s gentle breath at my ear and heard him say, “I want to please you. I will do anything. What do you want me to do?” My mind instantly raced with possibilities but I hesitated to answer him. Did I have the nerve to suggest what I really wanted? Would this be the time when I would finally find out what my girl friends just loved to have their lovers do to them?

“Please! I want to make you happy! I want to please YOU!”, He repeated.

Again, I hesitated.

I couldn’t wait any longer. I was going to ask. Today was going to be the day. Even though I mustered all of my nerve, I could only manage to faintly whisper, “Kiss me?”

Surprisingly, Jack smiled and, with approving eyes, replied, “Will you trust me?”

I just nodded.

He looked away and began to gently kiss behind my ear. I could feel my body tense up. I pushed my head deeper into the pillow, closed my eyes, and tried to relax.

Jack must have sensed my reservations because he went very slowly at first. I was hoping that if he was gentle, I would eventually relax and actually enjoy what would happen. His soft kissing of my chin and neck was already causing my breathing to slow down. He ran his fingers lightly over the lips of my mouth and occasionally, parted them. He moved his lips under my neck and lightly made circles with his tongue. I was becoming more and more relaxed. He had done all of this before and I soon found my mind wandering.

I was never really comfortable with the concept of having someone kiss me “down there”. Even though I am almost a hygiene freak, I still wonder “Do I smell OK? Will it taste OK?” I had no trouble giving Jack head (gee… I hate that term). But that seemed different somehow. I can’t seem to explain it.

Even though it would be with Jack, there always seemed something “gay” about it. My girl friends kept saying that I was crazy. That I would really enjoy it. It’s not something that all men like to do, but those that do, REALLY DO! I knew that Jack was in that category. He sure bugged me about enough. But I never had the guts to let myself go. Today was going to be the day.

Jack’s finger slid down from my mouth, down my chin and neck, and around the side of my right breast. It made me tingle all over. He lightly cupped my breast and kissed my neck. He traced a line with his tongue to my other breast. Then he did what I just love him to do. He licked around and around my nipple and occasionally, lightly pulled on it with his lips. Geeeez, that drives me crazy. I’ve always had sensitive nipples. Jack knows this and has always been gentle.

I was beginning to forget about what was going to happen and was really getting excited by Jack’s touch. I could feel that warm moist sensation between my legs as Jack continued to roll my nipple around with his tongue.

I was beginning to get so relaxed that I didn’t notice that Jack had now taken his hand off my other breast. It actually startled me when it “reappeared” on top of my pubic bone. He just let it rest there for a minute. I guess he wanted to make sure that I still wanted to go along with the original plan. I did, so I opened my legs. This allowed his hand to naturally fall between them. I just kept my eyes closed, took a deep breath, and tried to keep relaxed.

I could feel Jack’s middle finger resting right over the opening to my vagina. As I felt his finger begin to move from side to side, I opened my eyes and took a short deep breath. Slowly and gently, Jack used his finger to part the lips of my pussy. He didn’t try to put his finger in me. He just pressed against the outside with an everincreasing pressure until I could feel my lips surround his finger. I could also tell that I was making his finger warm and wet. It was a little embarrassing but I just loved to have him touch me. And he knew it. He looked up and gave me one of his famous “all knowing” smiles. I just closed my eyes again so he wouldn’t look at me. He started to move his finger up and down.

Then, at the top of his motion, I could feel his finger bend slightly. I knew what was next. Sure enough. With his next downward stroke, his finger slid right inside me. My back instinctively arched and I automatically heard an “Ooohh” come from my mouth. He started to use his finger just like he uses his wonderful cock. In and out, in and out. I loved it. I was getting more and more wet with each stroke. All the while he rubbed my clit with the palm of his hand. I opened my legs wider. Now I could really feel how wet I was getting. I was sure that some of my juices were going to drip out of my pussy. I didn’t care. When Jack quickened his strokes, I began to move my hips to match his rhythm.

I began to sense a faint musky smell. I knew it was from me but at this point, I just wanted Jack to keep going.

Then I felt a cool, wet sensation on my leg. I opened my eyes and looked down. I guess the feelings and sight of what Jack was doing to me was exciting for him too. His penis had started to drip its own lubricant. I always thought that was extremely y. I knew there was nothing that he could do to stop it. I loved to just watch it.

Then I did something that I’ve never done before. I reached down and collected as much of Jack’s juices that I could from my leg. Then I stroked his cock and milked more until my fingers were pretty wet. Without hesitating, I moved my hand on top of Jack’s and made sure that he could feel his own fluids mixed in with mine. I was so excited that I just kept my hand on Jack’s and joined in the thrusting motions of his fingers. I was going crazy. I put another one of his fingers in me. I wanted more!

The outside of my pussy was completely soaked now. My cunt made a thoroughly erotic squishing sound every time Jack’s fingers moved within me.

Jack continued the movement of his fingers and whispered into my ear, “Do you still trust me?” I guess my heavy breathing and clenched eyes told him that I was all his by now.

Then he STOPPED!! He took his fingers from my cunt and just stopped. I’m sure I had a look of horror on my face when I looked at him and said, “NO! NO! Don’t stop!” Quickly, Jack rose over me and positioned himself between my legs. I could see his stiff penis now poised where his hand had been. I watched as a drop from the tip fell directly onto my swollen clit. Just as suddenly as when he stopped, he thrust his cock deep into my cunt and immediately began a gentle thrusting motion.

Aaahhhh!! That was much better. I love how he fits inside me. It’s like we were made for each other. I love to feel how every little bump of his cock rubs against the inside of my pussy.

I was obviously enjoying what he was doing but, in a quivering voice, I said, “I want you to kiss me there.”

“Be patient, darling. I will”, Jack whispered back.

I tried to relax and closed my eyes. After all, things were pretty good so far. I really did trust Jack. Little did I know what his plans actually were. As he thrust in and out, I closed my eyes again.

Then I experienced something that I was totally unprepared for. Jack brought his left hand, covered with my wetness, right up to my face and began to rub his fingers on my lips! I was being bombarded with new sensations. I had never experienced my own smell so close before. It was startling and yet, exhilarating at the same time. Musky and yet sweet. For the first time, I actually felt its texture. It felt almost like a thin syrup and just slightly sticky.

I actually enjoyed what was happening! Even with my initial reservations, I was really turned on but what my body was doing! It was all so mysterious and wonderful. I was no longer afraid. I wanted more!

Each time his fingers would become dry, he would return his hand to my vagina. Once again, along with his cock, he would insert his fingers into me to get them wet. I couldn’t believe the sensation and said “YES! YES!”, In approval.

With each trip, I was more eager to feel his fingers once again rub more and more of my cunt juices over my lips. With each trip, I would take in great breath, filling my lungs with the sweet aroma. I started to use my tongue to greet his fingers returning with their precious cargo. I found the taste of my own sticky wetness absolutely intoxicating. All this just made me produce even more.

I wanted to be completely involved in what was going on. I began putting my own fingers onto my cunt to get them wet. Then I ran them over Jack’s lips. I wanted HIM to taste me. I wanted HIM to know how excited I was. I couldn’t do it fast enough.

I had lost all of my inhibitions about my body. There was nothing wrong. How could there be if I felt so good. I was ready. I wanted to feel a tongue, Jack’s tongue, licking my clit. I wanted him to feel, as intimately as possible, what was going on inside my body. I very firmly and assuredly said, “KISS ME!!… KISS ME!!”

Jack pulled his cock from my pussy and rotated his body until his face was right over my cunt. I wanted him to “see” me. I opened my legs as wide as I could. I could feel how the air was evaporating the juices that covered the outside of me.

I clenched my internal muscles as hard as I could. I knew what that would do and I wanted Jack to see it. I could feel how my muscles pushed more of my juices from the opening of my cunt. I could feel it begin to drip down towards my ass. It felt wonderful.

My face was no more than a few inches from Jack’s cock. When I opened my eyes, I could see just how much my wetness had covered his penis. His balls and cock were completely soaked. I lovingly watched the long clear drops drip onto my chest.

As if signaled by a starters pistol, we simultaneously plunged our faces into each other’s genitals.

I was entranced with the new sensation of my own taste and smell and feverishly rubbed my face all over Jack’s cock and balls. I couldn’t seem to move fast enough. I wanted it all. I reveled in the feeling of Jack’s soaked balls resting on my face as I licked the shaft of his cock. My excitement grew even more when I felt my face becoming more and more wet and how I could smell Jack’s special scent as well as my own.

Jack began to use his tongue to open and close the lips of my vagina. With ever increasing frequency, he would push his tongue deeper and deeper into my cunt. Every time he did so, I would raise my hips up in ecstasy. Deeper and deeper Jack would thrust his face, until it was completely covered with my liquids.

My excitement was reaching its ultimate peak. Sensing this, Jack began to use his tongue directly on my clitoris. He made ever intensifying contact while I pushed my hips up to his face. More and more of my fluids began to drip out. Each time, Jack would use his tongue to gather it up and redeposit it on my clit. Then he would lick and suck me until my body made more to get.

He was driving me crazy! I could feel contractions deep within me each time his tongue touched my clit. In a neverending cycle, my excitement grew. Each thrust of Jack’s tongue to collect more liquid caused me to shiver and breath even heavier. Each time his tongue returned to my clitoris, my hips rotated to exaggerate his movements. I couldn’t control myself any longer. My orgasm was here.

As my hips started to jerk, I announced, “I’m coming. I’m coming…”

Jack immediately buried his face into my pussy and thrust his tongue as deep into my vagina as it would go. Over and over again, my body shook as my orgasm progressed. My hips jerked down and my breathing turned to rapid shallow gasps as my vagina went into its joyous contractions. With each spasm, I could feel my orgasm deposit more and more of my cum on his face and tongue. It seemed to almost gush; almost like a man’s orgasm. I WAS IN ECSTASY!!

All of a sudden, I felt the cock laying against my cheek stiffen. I knew what was about to happen and I really wanted to feel it like Jack was feeling my orgasm. Just as I wrapped my hand around his cock, out spurted the first wave of cum that landed on my cheek. As quick as I could, I closed my lips around the tip of his penis and began draw it into my mouth. Jack’s second spasm all but completely filled my delighted mouth. Again and again his cock convulsed. I tried to keep as much of his wonderful cum inside but I couldn’t. With each succeeding burst, more and more of the warm white fluid leaked from the edges of my mouth and dripped down my cheek.

When it was over, we both just seemed to collapse. I was exhausted but my body tingled everywhere with the thrill of what had transpired.

I felt Jack lift his body up and settle onto me again. My opening eyes were greeted with the sight of his face, glistening in the candle light. I reached out and placed my hands on either side of his face. It was warm and very wet. I wanted to share one last expression of what had just happened. I drew his face to mine for a very special kiss.

As our lips touched, once again I could feel and smell my passion. Our lips parted and our tongue touched and began to move. With each succeeding contact, we exchanged our precious treasures. I shared the cum that had remained in my mouth and he eagerly mixed it with the juices from my cunt.

This had been a special moment indeed.

This My First Time with Jack