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Cindy's first time - a wonderful journey of discovery - Chapter 3

Jack wants to enter me, and take my virginity - I think I want that too!
I awoke the next morning, thinking that the word 'eventful' does no justice to the past 24 hours. Yesterday, I kissed Jack for the first time, he felt my breasts, fingered me and tasted me, driving me to a wonderful orgasm. He introduced me to his penis, and ejaculated all over my stomach as we humped together in my bedroom.

I could not resist masturbating last night as I lay in bed, recalling the wonderful day Jack and I had shared.

I woke around 6 a.m. I went on my normal run and timed it to finish in time to meet Jack when he came home from work. Jack arrived about 20 to 30 minutes later than usual.

I was anxious and nervous as I waited, wondering why Jack was late. My parents had just left for work when Jack drove up to his house next door.

I approached him and saw he was carrying a small bag that said ‘Walgreen’s’ on the side.

“You are later than usual,” I said.

“Yeah, I wanted to stop and pick something up at the store.”

I gave him a kiss. Then asked, “What’s in the bag?”

“Take a look,” he replied as he handed me the bag.

I opened the bag to find a dozen Trojan ribbed condoms. I looked at him as I tried to process the meaning of this, and tried to find the words to respond.

Before I could speak, Jack continued, “Cindy. I want to make you mine….I want to experience this with you; but I do not want to force you into anything. I really do care about you. But I do want to be with you in this way.”

I sat silently, I could feel my pulse quicken and my face flush. “Jack, this is a big step. I don’t know if I am ready for this.”

“I know. And if you are not ready, I will wait. But I wanted to be prepared for you when you decide you are ready.”

Jack paused to study my reaction. “We do not have to do anything, but I want you to know I want to make love to you.”

“Things are moving too fast,” I said, my voice revealing a nervousness as well as a level of excitement.

“OK, I won’t push you. Just keep these handy for when you do think you are ready to take the next step. OK?”

Jack tried to reassure me that he really would support whatever decision I made. I truly appreciated the fact that he was patient and would give me the time and space I needed to decide when I was ready.

Before we separated for the morning, he asked, “Would you like me to come over today?”

I nodded ‘yes’, but said nothing. God, I definitely wanted him to come over today. I wanted to be with him again, even if I did not know exactly what 'with him' would entail.

“We can talk more about this later, OK? I’ll see you about noon.” Jack said before kissing me briefly.

I walked to my house, carrying a bag of condoms, trying to decide what I wanted to do; or more importantly, what I needed to do.

For the next few hours, I contemplated what I wanted. I was completely torn. I wanted to give myself to Jack; totally and completely. But I was scared. I was not really ready for this.

I was excited and nervous….and very scared.

It was 12:20 p.m. when the door bell rang. I invited Jack in and we sat together on the couch.

“I think I want to do this,” I said nervously. Clearly the tremor in my voice conveyed a great deal of uncertainty.

“You think?” he responded.

“OK, I’m sure. I want to do this with you. I want you to make love to me.” I could feel my face flush and burn as I spoke these words.

A strange smile crept across Jack’s mouth. I sat silently for a second, trying to read the expression on Jack’s face. He cleared his throat and then asked, “Are you sure you are ready for this? There is no rush.”

I looked at him and nodded. I felt a slight twinge in my pussy as I contemplated what was about to happen.

“Jack, I want this too. And I want you to be the one.”

I was not sure if I had the presence of mind to make a rational decision at that moment. But I knew what I wanted to do; and even if I wanted to stop at that moment, I felt powerless to resist this temptation.

I stood up, walked to him and sat on his lap. I was wearing a yellow, pleated, halter-type sun dress that came slightly below my knees. My blonde hair was pulled back in a ponytail.
Looking deep into his eyes, I held his face and kissed him. Immediately, I felt his penis throb against my ass as he opened his mouth to accept my tongue. His penis was continuing to pulse against my bottom as I spoke. I loved the way his penis reacted to me.

“Jack, I want you to know that I love you. And a part of me always will always love you, no matter what happens between us.”

I paused to consider what I wanted to say next.

“I don’t have any silly illusions that this means we are together forever and ever; or that we get married some day. But I want you to know that I want to do this with you because I love you. I want you to be the one to whom I give my virginity.”

I paused again, trying to think what else I could say, but I could think of nothing to add. My words had pretty much summed up what I was feeling. I wanted him to 'be the one'.

“Cindy, I love you too. And I do not know what will ultimately happen to us. But I do know this; I will always cherish the memory of us being together,” Jack replied.

It was the first time either he or I ever said ‘I love you’ to anyone. This was a very special and tender moment for each of us.

I returned to kissing him deeply, and I took his hand and raised it to my breast. He felt me through the built-in bra of the halter sun dress. As he gently teased my nipple through the material, I knew I was going to take him inside me today.

I could feel my pussy growing wet in anticipation. I could feel my pulse in my erect clitoris. And every pulse of his penis against my bottom sent a twinge through my loins directly to my pussy.

I stood up for a moment. Standing in front of him, I reached up and I untied the pale yellow halter from around my neck. As I climbed back on Jack’s lap, this time I sat astride his legs, my legs around him.

As I did so, Jack adjusted his erection upward, allowing it to rest against his abdomen, forming a large cylindrical lump in his shorts. I stared into his eyes as I lowered the top of my dress, exposing my breasts.

Sitting astride him, my bare breasts exposed to his glance and his touch, I took his face in my hands, lifting it up, and resumed kissing him with all the passion I had. I sucked his tongue into my mouth.

Jack cupped both of my breasts in his hands as our tongues danced together once again. Our tongues chased each other from his mouth to my mouth, and then back again.

I humped forward, pressing my crotch into his erection, grinding my erect clit into his rigid cock. I could felt my slippery wetness leaking from me, soaking the gusset of my panties.

As I ground myself into him, he humped back into me, and gently teased my nipples. Jack had a naturally sensuous touch about him; he simply knew how to touch and please a woman.

He broke off the kiss, and then, leaning forward, took one of my nipples into his mouth, sucking on it gently, causing me to moan out loud as I held his head to my breast. I was in absolute ecstasy. I did not ever want him to stop sucking my breasts.

I continued to grind our crotches together, humping both of us into a frenzy of arousal. I felt very, very sexy sitting astride the man to whom I had decided to give my virginity today. We petted for several minutes, panting into each others mouth, exploring each others bodies.

“Jack, let’s go into the bedroom.”

I was ready to give myself to him.

I returned for one last tongue probing kiss before arising from his lap. I took him by the hand and began to lead him to my bedroom. My breasts swayed gently as I walked.

As we approached the bedroom door, I could feel my heart pounding in my chest as I realize ‘this was it, this was the moment of truth. I was going to give myself to him totally now.’

I sat on the edge of the bed, my bare breasts in view, the top of my dress hanging down from my waist. I bade Jack to stand in front of me as I unbuckled his belt, undid his fly and lowered his shorts and boxer shorts, allowing his massively erect penis to spring into view.

As I was unbuckling his shorts, Jack was kicking off his shoes.

Jack stepped out of his pants and boxers, and began removing his shirt. He had a marvelous body, tight but muscular chest and arms; powerful, athletic legs; tight, flat stomach; and a long, thick, very rigid erection waving in front of my face. He was my Adonis.

“Damn you are a very sexy,” I said as I ran my hands up his chest, stopping to play with his nipples as I leaned forward and took the head of his penis into my mouth. I stopped just long enough to add, “very sexy indeed.”

This was the first time I had kissed his penis.

His penis arched upward each time I licked the head with my tongue. He moaned loudly as I took the glands into my mouth, wrapping my lips just below the pronounce ridge of its head.

I sucked and licked the large bulbous head for several seconds. I tasted a salty, slightly bitter trace leakage from his penis as it arched up in response to my tongue and lips. I quickly understood that this leakage was the pre-ejaculation seminal fluid that our teachers warned us could get us pregnant. I guess they were right health class. The boys do leak a little sperm prior to ejaculating! Withdrawal was not a viable method to prevent pregnancy!

I then pulled his erection from my lips and studied it. I stroked him up and down with my fist as I examined this magnificent example of manhood. As I stroked him, the tiny hole at the tip of his penis seemed to open and close slightly. This intrigued me.

The first time I inserted the tip of my tongue into the small slit opening at the tip of his penis, Jack shuddered and his knees seemed to buckle slightly. His hands came up to the sides of my head and he moaned loudly, letting me know how much he liked that. And because he liked it so much, I did it again, and again, and again; evoking the same moan and shutter from him each time.

I could still barely detect the trace amount of seminal fluid leaking from his erection; yet I enjoyed the salty, slightly bitter taste that was barely there. I decided I liked tasting this trace sample of his semen.

Jack looked around and asked, “Cindy, where is the package I gave you this morning?”

I removed his penis from my mouth to answer as I nodded towards my dresser.

Jack spotted the Walgreen’s bag and went to retrieve it. His large erection swayed proudly in front of him as he returned, opening the bag and fishing the package of condoms out of his pocket, and began struggling to open the packaging.

The tin foil wrapper was particularly challenging to open. He looked so cute as he struggled to tear the foil wrapper. He finally took the edge between his teeth and ripped it open.

I watched this process intently. He removed the condom and placed it on the tip of his erect penis, holding the shaft steady with his left hand. Then slowly and carefully, he unrolled it over the length of his tool, leaving the reservoir vacant at the tip.

The beige latex masked the thick ridge of its head and the thick veins somewhat, making his cock look slightly safer and less intimidating.

The ribbed ridges ran circumferentially around his girth, barely visible. I reached up and felt the shaft and could feel the distinct ridges from the prophylactic around its girth.
I stood up and very nervously I stepped out of my dress, leaving me only wearing my shear white panties. “Jack, would you like the honor of removing my panties?” I asked standing in my most provocative pose, my erect nipples pointing upward, and my hand on my hips.

Rather than answer, he simply knelt in front of where I was standing, with his fine ‘latex covered’ erection waving at the ceiling in front of him, and he began to pull my panties down, kissing my breasts as he did so.

Looking down at him, his mouth on my tits, his penis standing proudly, erect in front of him, he was one of the most erotic sights I had ever seen.

As Jack lowered my panties to my ankles, I stepped out of them, standing completely naked before his adoring eyes. I reached my hand out to him and guided him to stand.

He towered over my 5 ft, 9 inch petite frame. I had not realized the stark difference in our heights previously, but, at 6 ft, 3 in., he was several inches taller than I was. Being a tall girl, it pleased me that he was taller than me; he made me feel petite and feminine for the first time in my life.

And standing facing each other, his rigid cock reached to my breasts. I wanted to give it one last kiss and suck, but the latex condom discouraged me from trying that.

I guided him to lie on his back on the bed, and climbed on top of him, straddling his hips and his erection, pointing the head of his magnificent cock at the opening of my vagina as I positioned myself over it. I rubbed his head back and forth at my opening for several seconds.

He arched his hips upward instinctively trying to hurry me along. I pulled back away, leaving him humping at the air, teasing him with the prize he coveted: my virginity.

“Patience, my good man. Patience,” I teased.

And again holding the head of his erection at my opening momentarily, I slowly lowered myself down on him putting an inch or two inside me. “Oh god, you feel so big and thick. I don't know if you will fit inside me.”

I raised myself up, pulling him nearly out of me, and then lowered myself down again, a bit further this time, taking more of him inside me. I could feel myself being stretched open, almost pried open. It was slightly uncomfortable to be stretched this much, but it also felt good to have the helmet of his large cock inside the opening of my vagina.

I knew I needed to go slowly. I adjusted my position and raised up, and slowly lowed myself down a bit, taking a couple of inches inside me.

I repeated the motion, With each slow thrust as I struggled to accommodate a bit more of his significant girth as I slowly worked him deeper and deeper inside me.

I had taken 2 to 3 inches inside me when Jack arched his hips and tried to push a little deeper. Suddenly, there was a searing pain inside me. It felt hot and sudden inside my uterus.
“Oh shit! Stop!” I cried out as I panted for a moment, trying to figure out what happened.

Suddenly, I realized that Jack had just ruptured my hymen. I was officially no longer a virgin. I remained motionless for a minute or so. I insisted he do the same.

The pain subsided after a few moments. I raised up and lowered myself cautiously again, very slowly.

He was so very hard. I now had slightly more than half of his penis inside me. I looked down between my thighs to see that I had another 3 inches or so to accommodate.

In this position, after allowing him to penetrate me with the first four or five inches or so, the head of his cock was rubbing the front inside wall of my uterus, stimulating my g-spot. He was sufficiently large to cause me to have to work slowly to open up enough to fully accommodate him without encountering the sudden shock of pain as I had moments ago.

Jack was a well endowed man. It took me several more cycles of raising up and slowly lowering myself down before Jack had wedged himself completely inside me. I felt very full, stretched in fact.

I felt like the head of his large was way inside my stomach, far deeper inside me that anything penetrated me previously. In fact, prior to yesterday, nothing had penetrated my vagina further than my own fingers could reach, which was not very deep at all.

I was surprised that my vagina could accommodate such a large erection, but all of Jack's manhood was now buried deep in my uterus.
Once I had all 7+ inches of Jack fully inside me, I leaned forward to place even more pressure on my front wall. This pressure on my g-spot was very intense and pleasurable.

I honestly did not even know the term 'g-spot' at the time. But Jack had introduced me to this spot on the front inside wall of my uterus, and I liked it. I liked it a lot.

I knew I could climax fairly quickly in this position as I slowly began to rock back and forth on Jack’s rigid tool, grinding the head against my g-spot.

I experimented with various movements. I was learning how to fuck as I rode on top of Jack's large boner.

Initially, I moved up and down, raising myself nearly off the massive cock inside me, and then plunging down on it, driving the large head deep inside my womb. I loved the feeling of it plunging in and out of me, but that movement was fairly intense and exhausting.

As our pace quickened, Jack pulled me forward, and held me tight. He began thrusting up inside me to drive himself deeper inside my womb with each stroke, banging hard against my cervix. I began moaning through my panting breaths.

As my excitement began to build, I discovered that I could actually keep Jack’s boner inside me and slide myself back and forth, grinding the head into the front of my womb as he pounded in and out of me, pressing the large plum shaped head into my cervix.

I could feel a powerful climax starting to build in my core. If Jack could hold out a few minutes longer, I was going to cum all over his latex encased erection.

“Oh, Jack, you are going to get me there. I am getting so close. Oh god, you are so deep inside me. God you feel good. You make me feel so very good,” I hissed.

I leaned further forward and began kissing my lover, sucking his tongue into my mouth, moaning loudly into his mouth as my hips began bucking wildly. I quickly crossed that magic line that triggered the first of a series of waves crashing though my core.

Jack then pushed me back, into a seated position. In this position, our bodies were perpendicular to each other. In this position his erection was pressed firmly into the front wall of my uterus, stimulating my g-spot.

That was all it took to trigger my orgasm.

“Oh God, Jack, I am cumming. You are making me cum so hard.”

Jack continued to thrust his hips up, banging into me with all his might as I started my second series of orgasmic waves. I was in ecstasy riding my lover. I felt like a bronco rider, straddling my lover as he bucked his hips against me, driving me into the air slightly with each thrust.
Then without warning, Jack flipped me over on my back without disengaging from me. It was an impressive move that would have made any Olympic wrestler, or any gymnast proud. Without ever leaving my open vagina, Jack was on top of me In this position, he was punishing my pussy with deep, violent thrusts as I continued to cum. He was literally slapping himself ‘balls deep’ into me with each brutal thrust.

We were well past the point of gentle love making; we were fucking like wild animals.

I was crying out in incoherent moans and grunts. It was as though I was 'speaking I tongues'. The sounds emanating from my core were incomprehensible.
I knew he was preparing to erupt as well. I was being fucked violently and powerfully. Jack was driving my ass into the mattress, and my head into the head board with each punishing stroke. I had to reach up behind me with both arms to brace myself against the head board to keep from banging my head with each powerful thrust.

I was literally yelling loud screams of pleasure as each time he pounded into me, it sent an orgasmic wave crashing through my core. I was not sure I could take any more; I feared I might pass out. I wrapped my legs around him, digging my heels into his ass, wanting to accept him as deep as I could.

Jack’s entire body then became rigid with a final deep thrust, and I could feel his penis throbbing deep inside my womb. His hands were on my hips holding me in place to accept his ejaculating penis as it pumped its seed. I knew the condom was catching the semen, nonetheless, I enjoyed the fact he was cumming inside me.

He collapsed into a heaving pile of sweat and emotion on top of me. My legs around him, holding him in place, not wanting to allow him to escape from my very dilated pussy too quickly. I caressed his head as he lay panting on top of me. We were both completely satisfied, sated beyond belief.

“Jack, that was wonderful. I love you so much.”

With his cock still inside me, he looked deep into my eyes. “I love you too, Cindy. I really do.”

I squeezed his still erect penis with my vagina. And we lay there coupled together for several minutes, trying to recover out senses and our breath. I did not want to disengage; I wanted to savor this moment as long as I could. I wanted to feel him inside me as we rested.

I loved this newly discovered feeling of a man inside me after I achieved an orgasm. Even today, I still think that there is nothing quite so wonderful and feeling a penis continue to pulse deep inside you as you cuddle in post-coital bliss.

After two or three minutes of lying motionless, Jack surprised me as he began to slowly resume moving in and out of me. He was moving slowly at first, but he was slowly increasing the pace.

He was still hard! My God, he is going to go at it again!

“Jack, are you going to fuck me again?”

“I think so.”

He started pulling all the way out and slapping his cock suddenly back inside me. It felt great, but I knew I could not cum again so soon. Nonetheless, I used my heels in his ass to ‘spur him on,’ and he picked up tempo.

But the increased friction from the latex rubber began to make me a bit sore as he pounded me again, and again. Having just cum, Jack had more stamina this go around.

After about 5 minutes, I said, “Jack, I am getting a little sore. Go ahead and cum if you can.” That seemed to be all it took. Moments later his entire body grew rigid again, and his erection was throbbing inside of me pumping out whatever semen he had left in reserve.

Once he finished cumming, I decide it was time to de-couple. I did not want to take the chance that he would remain hard and try to fuck me a third time. My poor little, recently deflowered pussy was not up for that!

I gently pushed him off of me and over on his side, and on to his back. His large penis flopped against his stomach, making sloppy sounding exit as it left my sore and dilated pussy.

I leaned over and studied his cock. There was a trace of blood on the latex sheath, evidence of my ruptured hymen. Jack grew a little softer, but largely, he remained fairly thick and large. The reservoir tip of the condom was fully charged with his semen. It looked like it might burst if we were not careful.
I took hold of his semi-flaccid cock and rolled the latex up until I could remove it. Without thinking, I placed my index finger inside the condom and retrieved a dollop of semen. I brought the strange elixir to below my nose and inhaled the wonderful aroma of his sperm. I found the scent, which was mixed with the smell of the latex, pleasant and exotic.

“You even smell good,” I explained. "I like your scent."
Then I got up, and discarded the condom in a tissue in my toilet and flushed away the evidence of our sin. I returned to the bed to cuddle some more.

We lay together on the bed, naked, gently caressing each other in the glorious after glow of very satisfying sex. I dozed off for a few minutes with my head on his chest. I was a very contented lady. I woke about an hour later. Jack was snoring slightly. I felt us sleeping together was nearly as intimate as our coupling.

I listened to Jack’s heavy breathing and snoring for 30 to 45 more minutes before he began to stir.

We kissed and then got up. I put my panties and dress on.

Jack smiled at me and asked, “Are you OK with this? I mean, are you OK with what we did?"

It pleased me that Jack was concerned that I was not having any regrets.
I smiled, nodded and said, “Yes, I am much more than OK.”

I then touched myself between my legs and grinned. I said, "However, I feel like I have been riding a sand paper hobby horse all afternoon. My poor little pussy is pretty sore right now!”

Jack then suggested, “Perhaps we should get you on birth control pills? I would like to ‘feel the real you’.”

I nodded in agreement. I did want to have his semen inside me. I definitely want to allow Jack to ejaculate inside me without the latex barrier. We need to get me on the pill as quickly as we could.

I then thought to myself, 'I really am falling in love with this man.'

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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