I awoke the next morning, thinking that the word eventful does no justice to the past twenty-four hours. Yesterday, I kissed Don for the first time, he felt my breasts, fingered 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 Don and I had shared.
I woke around six a.m. I went on my normal run and timed it to finish in time to meet Don when he came home from work. Don arrived about twenty to thirty minutes later than usual.
I was anxious as I waited, wondering why Don was late. Nervously, I worried if Don was avoiding me. Was yesterday a one-time occurrence? I filled my head with all types of horrible scenarios as the minutes ticked by slowly as I waited for Don to arrive home.
My parents had just left for work when Don drove up to his house.
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 with a detectable panic in my voice.
“Yeah, I wanted to stop and pick something up at the store.”
He seemed a little nervous himself. I began to panic. Did he regret getting involved with me?
I gave him a quick 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, Don continued, “Lisa. I want to make you mine…I want to experience this with you; but I do not want to force you into anything. I am prepared to wait until you know you are ready…until you know it’s the right time for you.”
Okay, my biggest fear was alleviated, but now I was faced with another problem, or if not a problem, a huge decision. I was not prepared for our relationship to advance so quickly. Twenty-four hours ago, no one had ever touched me below the waist! Now Don was talking about taking my virginity!
I sat silently, I could feel my pulse quicken and my face flush. “Don, 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.”
Don 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.
“Okay, I won’t push you. Just keep these handy for when you do think you are ready to take the next step, okay?”
Don 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, okay? I’ll see you about noon,” Don 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 Don, totally and completely, but I was scared. I was not really ready for this.
I was excited and nervous…and very scared. The gusset of my panties was soaked all morning as I recalled yesterday’s adventure and contemplated what Don was proposing. I had deep feelings for him. I was not certain whether or not my feelings had matured to the point of being love, but I felt a deep, genuine affection. It was real and it would last a lifetime, of that I was sure. I also knew that when I lost my virginity, I wanted it to be to Don, and if not today, soon.
It was 12:20 p.m. when the doorbell rang. I invited Don in and we sat together on the couch. I was wearing a yellow, pleated sun dress that came slightly below my knees. My blonde hair was pulled back in a ponytail.
“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.
“Okay, 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 Don’s mouth. I sat silently for a second, trying to read the expression on Don’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.
“Don, 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. Looking deep into his eyes, I held his face and kissed him. Immediately, I felt his penis throb against my bottom as he opened his mouth to accept my tongue. His penis was continuing to pulse against my ass as I spoke. I loved the way his penis reacted to me.
“Don, I want you to know that I love you. And a part of me 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. Still, 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.
“Lisa, 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,” Don replied.
It was the first time either I ever said ‘I love you’ to anyone, and the first time anyone had told me that they loved me. This was a very special and tender moment for me.
I returned to kissing him deeply, and I took his hand and raised it to my breast. He felt me through my bra and the silky material of the 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 wetter 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 behind me and unzipped the pale yellow dress and let it fall to the floor. I stood there in my matching yellow bra and bikini set, posing for a moment.
“Lisa, you truly are the most beautiful woman I have ever seen.”
“I hope you will always feel that way.”
I reached between my breasts and unclasped the hook holding my 34B bra cups together, but I did not remove the bra. It hung loosely, still covering my very erect nipples.
As I climbed back on Don’s lap, this time I sat astride his legs, my legs around him.
As I did so, Don 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 he reached up and opened the cups of my bra, exposing my breasts. I slid the straps off my shoulders, allowing the bra to fall to the floor behind me.
I was now wearing only my bikini panties.
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.
Don cupped both of my breasts in his hands as our tongues met once again. Our tongues danced from his mouth to my mouth, and then back again.
I broke off our kiss long enough to beg, “Pinch my nipples…but not too hard.”
Don took each of my nipples between his index finger and his thumb and gently pinched them, causing me to moan into his mouth.
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 pressed against him, he humped back into me, and gently teased my nipples. Don had a naturally sensuous touch about him; he simply knew how to touch and please me.
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 other’s mouth, exploring each other’s bodies.
“Don, let’s go to my 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 realized 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, wearing only my panties, my bare breasts in view. I bade Don to stand in front of me as I unbuckled his belt, undid his fly and lowered his shorts and boxers, allowing his massively erect penis to spring into view. As I was unbuckling his shorts, Don was kicking off his loafers.
Don stepped out of his shorts 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 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 glans into my mouth, wrapping my lips just below the pronounced 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 in health class. The guys 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, Don 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 shudder 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.
Don looked around and asked, “Lisa, where is the package I gave you this morning?”
I removed his penis from my mouth to answer as I nodded towards my dresser.
Don walked over to my dresser, opened my top drawer and 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 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. I watched with great amusement as his erection bobbed up and down wildly as Don wrestled to open the wrapper. In apparent frustration, 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. Obviously, he had done this before.
The beige latex masked the thick ridge of his head and the thick veins somewhat, making his cock look slightly safer and less intimidating.
The ribbed condoms had a series of tiny, barely visible, grooves that ran around his girth. I reached up and slid my fist up and down the well lubricated shaft of his cock. I was surprised at how distinct the series of circumferential ridges felt to my touch.
“Oh my, those little ridges are a lot more noticeable than I expected,” I commented with a bit of alarm.
Naively, I worried that the ribbed contour would hurt me. I would soon learn that I need not be concerned with that. I would soon learn that the tiny grooves and ridges were quite pleasurable.
Don chuckled, “Well they are ribbed condoms. Once you get used to the feel inside you, I think you’ll like it. They put them on the rubbers for the lady’s enjoyment.”
I stood up and very nervously asked, “Don, would you like the honor of removing my panties?”
I assumed my most provocative pose, my erect nipples pointing upward, and my hand on my hips waiting for his response. 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.
Don lowered my panties to my ankles, and I stepped out of them. I was now standing completely naked before his adoring eyes.
Don, still kneeling in front of me, placed his right hand on my inner thigh and looked up at me. I understood what he wanted me to do. I spread my legs slightly, allowing his hand to move up my inner thigh.
I closed my eyes and listened to my own labored breathing as I felt his fingers slowly trace their path up my inner thigh to my very wet pussy. The teasing slow manner in which he moved his fingers towards their goal had me rocking my hips ever so slightly in anticipation of his touch.
Don’s fingers were inches from my vulva when I begged, “Please, touch me.
His fingers slowly opened the wet outer folds of my labia to reveal my excitement.
He ran his fingers up and down my slit, paying particular attention to my now erect and sensitive clitoris causing me to gasp loudly. I stood there, biting my lower lip. I would make a slight moan involuntarily every time his fingers contacted my clitoris.
“You are very wet, Lisa.”
“I’ve been wet all morning thinking about you, thinking about today,” I confessed.
He started to slide his fingers inside of me.
Standing with my legs apart while squatting slightly to open myself up to Don was difficult, and I started to topple forward a bit. I reached out and balanced myself by placing each of my hands on his shoulders as his fingertips found my wet opening and entered me.
He quickly had one, then two fingers inside me. My lubrication was literally flowing out of me now, coating my inner thighs, making them slippery. Unlike yesterday, when Don struggled to penetrate me for the first time, today his fingers found no resistance to entering my dilated vagina. I was open and ready.
He curled his two fingers back towards himself, deep inside me, massaging the front wall of my vagina, deep inside me at my g-spot. I was responding just as he hoped, or perhaps knew I would.
I found myself squatting deeper and opening my legs wider. I could feel my orgasm starting to build.
“Don, you’re going to make me cum… I can’t hold out much longer…”
I was rocking my hips in a synchronized motion to the internal massage Don was giving my vagina, continuing to steady myself by holding on to his massive shoulders, balancing myself as I squatted deeper and deeper. I wanted his fingers to reach inside me as deep as they could.
I could feel my excitement building, but several times, an instant before I could cross that magic line that would trigger my orgasm, Don would stop wiggling his fingers inside me. I would hump against his hand in frustration.
“Oh fuck, don’t stop…I’m so close…don’t stop,” I cried out each time.
In response Don would resume the internal massage again until I was right at the edge, and then he would stop again. It was a form of torture that aroused me beyond belief. I needed to cum so badly, I was almost crying.
“Please, let me cum…please,” I begged.
After several minutes of taking me to the brink, Don finally pushed me over the edge. As my arousal grew, my movements became more pronounced. I was humping against his invading fingers with a violent rocking of my hips.
“Oh, fuck…I’m going to cum…just like that, just like that…oh fuck,” I cried out as a series of convulsions shook my entire body.
My breasts were heaving as I struggled to maintain my balance as wave upon wave of pleasure crashed through me.
“Oh thank you. I needed that. You have no idea how badly I needed that,” I panted as his fingers exited my vagina.
I reached my hand out to him and guided him to stand.
I felt such an outpouring of love and affection for him at that moment. “Don, I think I’d like you to fuck me now. Would you do that for me? Be my first?”
Don simply nodded as he stood. He towered over my five foot, nine inch frame. I had not fully realized the stark difference in our heights previously, but, at six foot, three inches, 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 truly petite and feminine for the first time in my life.
Standing facing each other, his rigid, latex-encased cock reached to my breasts. I wanted to give it one last kiss and suck, but the latex condom discouraged me from trying that.
Don guided me to the bed where he laid on his back. He motioned for me to climb on top of him and straddle his hips. With my knees on either side of his torso, I reached down and grasped the shaft of his erection, pointing the head of his magnificent cock at the opening of my vagina as I positioned myself over it. I rubbed the glans over my erect clit before separating the lips of my labia with it.
Having already had my first orgasm, my urgency was somewhat abated. Don, on the other hand, urgently needed his release. 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.
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 lowered 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 two to three inches inside me when Don 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 vagina.
“Oh shit! Stop!” I cried out as I panted for a moment, trying to figure out what happened. “Hold still…don’t move.”
Suddenly, I realized that Don had just ruptured my hymen. I was officially no longer a virgin. I remained motionless for several seconds, and 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 three 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 pussy, 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.
Don was a well-endowed man. It took me several more cycles of raising up and slowly lowering myself down before Don had wedged himself completely inside me. I felt very full, stretched in fact.
I was surprised that my vagina could accommodate such a large erection, but as I felt his testicles pressing against my ass, I knew that all of Don’s manhood was now buried deep inside me.
I sat straight up to place even more pressure on my front wall. This pressure on my g-spot was very intense and pleasurable. I slowly began to rock back and forth on Don’s rigid tool, pressing the head against my g-spot and simultaneously grinding my clitoris on his rigid shaft.
I experimented with various movements. I was learning how to fuck as I rode on top of Don’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, Don pulled me forward, and held me tight. He began thrusting up inside me to drive himself deeper inside my pussy 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 Don’s boner inside me and slide myself back and forth, grinding the head into the front of my vagina 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 Don could hold out a few minutes longer, I was going to cum all over his latex encased erection.
“Oh, Don, 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 another series of waves crashing through my core.
Don 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, Don, fuck me. Don’t stop. You’re gonna get me off again,” I screamed.
Don 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, Don flipped me over on my back without disengaging from me. Without ever leaving my open vagina, Don 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 in 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. Don 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 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.
Don’s entire body then became rigid with a final deep thrust, and I could feel his penis throbbing deep inside me. 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.
“Don, that was wonderful. I love you so much.”
With his cock still inside me, he looked deep into my eyes. “I love you too, Lisa. 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 as feeling a penis continue to pulse deep inside you as you cuddle in post-coital bliss.
After two or three minutes of lying motionless, Don 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!
“Don, 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 ribbed latex began to make me a bit sore as he pounded me again, and again. Having just cum, Don had more stamina this go around.
After about five minutes, I said, “Don, 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 a 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. Don 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.
“I do 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 afterglow 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. Don was snoring slightly. I felt us sleeping together was nearly as intimate as our coupling.
I listened to Don’s heavy breathing and snoring for thirty to forty more minutes before he began to stir.
We kissed and then got up. I put my panties and dress on.
Don smiled at me and asked, “Are you okay with this? I mean, are you okay with what we did?”
It pleased me that Don was concerned that I was not having any regrets.
I smiled, nodded and said, “Yes, I am much more than okay.”
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!”
Don 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 wanted to allow Don to ejaculate inside me without the latex barrier. We needed 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.’
(Note: a special thank you to the real Lisa and Don whose assistance in proofreading and editing this story has been invaluable. The quality of these chapters has been greatly enhanced by their input.)
