Elizabeth’s story – Chapter 7: Gary takes my virginity

Chapter 7

Elizabeth’s story – Gary takes my virginity 

Friday:

As I had promised Gary last night (Thursday night), I took steps to get contraception for our planned big event; the capture of my virginity by my stepbrother. Although I still had serious reservations about doing this, I was committed to keeping my promise and giving myself to Gary as soon as it was ‘safe’. Midday on Friday I skipped my study hall, lunch and poli-sci class and went to the local planned parenthood clinic to get birth control pills.

I was nervous about going in and having to justify my need for birth control. I feared they would ask me with whom I was having sex. I certainly could not tell them ‘my stepbrother’. I constructed a story I would tell them if asked. Of course, they did not ask.

The female clinician was helpful and friendly, but was adamant that I needed to use another form of birth control form at least seven days following the start of taking the pills. I assured her I would. Actually I would simply postpone intercourse for one week.

My anxiety was running high when I got to my car in the parking lot of clinic with the three month supply of pills. They came in a circular plastic container that numbered the days of the month. It was a clever container that allowed you to align the days of the week with the pills you should take on each day to help you stay on track. I took my first pill before leaving the clinic parking lot.

I felt mature, wicked, and sinful; but I was excited about what I was planning to do with Gary, and that excitement translated into a continued state of arousal.

I returned to school in time for my American literature class. But in the class, I was so distracted that I did not hear a word of the discussion of Sinclair Lewis and the impact of his work ‘Arrowsmith’. It turns out that ‘Arrowsmith’ was a noteworthy book before ‘Aerosmith’ was a band.

I ran into Gary in the hallway. He was obviously curious about my ‘contraception run’.

“Well?” he asked me.

“All taken care of,” I responded. He beamed with a huge smile. I continued, “but we are not safe for seven days.”

This news took him by surprise and his smile quickly evaporated. “Huh?”

“It takes seven days for the pills to be effective. You have to wait until Friday, a week from today at the earliest.”

He was obviously disappointed with this latest set back; but we would just have to wait. It would be a long, long week for both of us.

The week went as you would expect, a lot of petting, masturbation, dry humping, and oral sex in addition to a great deal of anxiety of what was just around the corner for us: full intercourse!

Friday could not get here soon enough.

Friday evening:

Neither Gary nor I had to be reminded of the significance of Friday evening and the arrival of the weekend. I know both of us were nervous, and quite anxious for Mom to get her ‘buzz on’ and retire for the evening so we could ‘seal the deal’.

At 8:30 p.m., Gary was growing a bit impatient waiting for the ‘alcoholic switch to kick on’ in Mom’s brain which would allow her to pass out and sleep through the night.

Looking back on that time in all our lives, I regret a great many things. But one of my many regrets is that I did not appreciate the hell Mom was going through as she battled the demons of my stepfather’s death and the demons of her alcohol addiction each and every night. Like a typical teenager, I was too caught up in my own pain and troubles to be aware of my mother’s pain. I wish I had been more aware and more supportive.

Nonetheless, it was a few minutes after nine o’clock when Mom made her final move to her room, her last drink in hand, to crash for the night. This opened the door for Gary and me to rush upstairs to consummate our completely improper, but highly intimate and pleasurable sexual relationship.

As soon as Mom’s bedroom door clicked closed, Gary stood, took me by the hand and led me to my bedroom. As he closed my bedroom door behind me, I could feel my heart pounding in my chest in anticipation, and fear, about what was next.

“Gary, let’s take our time. Let’s not be in a rush here. We both want to remember this as something special…”

Gary interrupted me, “Of course. This is a night we will both remember for the rest of our lives; but neither of us will ever be able to tell another soul about it.”

At the time Gary said that, I was sure he was right. But here I am, ten years later telling all of you every single detail about it. But you do not really know who I am, right? So I have the luxury of anonymity here, right? I mean, eventually, I had to tell someone, and it might as well be all of you; several thousand readers who I now consider among my closest friends and confidants, right?

I walked over to Gary, and pulled his shirt over his head, leaving his chest bare. I ran my fingers across his chest, stopping at his nipples and caressing him as he struggled to get my shirt off. Yes, we were awkward. No, we were not skilled lovers yet. And the nervousness of what we were about to do only added to our awkwardness. But it was exciting just the same.

Gary’s pants were poking out in front, revealing a sizable bulge forming. I reached down and caressed his penis through the material and adjusted his cock so that it could comfortably point upward. I was impressed to see an inch or two of the purple tinted head of his penis poking above the waistband of his pants. It seemed like the head was poking up and saying, ‘where’s Liz?’

I liked the thought that his penis was looking for his ‘good friend Liz’. My stepbrother had a very nice cock indeed.

After a slight struggle, Gary removed my shirt. I stood back from him and removed my bra, freeing my perky breasts and their taught, erect nipples. I glanced at the mirror and caught a glimpse of Gary and me standing there, both naked from the waist up, Gary’s erect penis peeking above the waist band of his pants.

Objectively speaking, we looked good standing there together. Gary turned me so I was facing the mirror, and, while standing behind me, wrapped his arms around me, cupping my left breast with his right hand. We made a very handsome, albeit inappropriate, couple.

My right nipple, which was fully exposed, was a bright pink; and stood out erect in excitement, like a firm little pebble. My blonde hair and green eyes gave me a cute, youthful and innocent, ‘Meg Ryan-like’ look that contrasted with the sexiness of my exposed breasts and abdomen.

Gary towered several inches above me. His strong frame was much larger, and stronger than mine. Gary and I shared the same blond hair, green eyes appearance that gave him a cute, ‘surfer boy’ look. Gary’s arm, which was wrapped around me, was muscular; as was his chest. He was a tall, strong, handsome young man; no question about it.

I could feel Gary’s penis pulsing against my ass as I stood there watching his one hand fondle my breast. I leaned my head backwards against his strong chest and savored the moment; the last few moments I would ever have as a virgin. The entire situation seemed surreal then, and still does now.

Gary reached down and unsnapped my shorts, and lowered the zipper. I could see my pale green panties peeking through the open zipper on my shorts. Gary began to lower my shorts, and my panties came with them. As my shorts were pulled past my ass and thighs, my light blond pubic hair came into view. It was very fine. I have a fair complexion and do not have much body hair. The thin, fine, blond pubic hair appeared almost translucent and provided very little cover for my now wet and aroused vagina.

I was naked in front of my stepbrother, and I liked being exposed, and vulnerable, this way. It excited me.

I stepped out of my shorts and panties, while I reached behind myself to grasp Gary’s erection. He was fully erect and very hard, actually, rigid, would be a more appropriate term. Now naked, I was fully exposed. With my back still towards him, Gary reached down to my vagina and found my erect clit and gently stimulated me with soft little circular motions that evoked a soft moan of pleasure from me.

“Mmm, that feels nice, Gary,” I encouraged him. I was already very wet and aroused.

After a few moments of this pleasurable foreplay, I turned to face him. I looked admiringly at the head of his penis still poking above his waistband. Kneeling in front of him, I unsnapped his pants, opened his fly and pulled his pants and boxers down together, revealing the entire erect penis. His pants and boxers fell to his ankles leaving him essentially naked in front of me.

I took Gary’s erection in my mouth as I knelt in front of him, as he struggled to free himself from the pants and boxers which were now wrapped around his ankles. I found it mildly amusing to have him in my mouth as he kicked and wrestled trying to get his pants, which were turning themselves inside out, off his ankles and feet. His penis bobbled and jerked in my mouth as Gary wrestled himself free.

I do not know why, but rather than reach down and assist him in getting free from his pants, I got some level of enjoyment allowing him to struggle himself free while keeping the head of his cock in my mouth. I guess even step-siblings just naturally try to torture each other, even when they are engaged in completely inappropriate sexual activity, huh?

Once freed from the shackles of his pants, Gary took my hand, and pulled me standing. I released his erection from my mouth as I stood. Then I leaned forward to give his firm erection one last kiss on its purple head. I liked Gary’s penis; I liked it a lot. And I felt a real possessive ownership of Gary’s penis, too. It was my pet, my toy, and it responded so well to me. It flattered and adored me. It was my friend! I guess a girl always has a bit of an emotional attachment to her first penis. I certainly did.

Gary led me to the bed and laid me on my back. Gary climbed between my legs, taking my knees and spreading them wide. I could feel my vagina open to his admiring gaze. I was wet and aroused, but afraid and nervous. Gary stared at my vulva for several seconds, “God, Liz, you are so beautiful.”

I could see his penis arch up in front of him as he said those words, indicating to me how sincere his admiration was. I loved knowing that he found me beautiful. I felt so very exposed and wicked lying there; and that exposure excited me further.

Gary leaned forward and kissed my vagina. Taking his fingers, he gently opened the folds of my vaginal lips and touched my erect clitoris with the tip of his tongue, sending a shock of pleasure through me.

“Ohhh, that feels nice,” I exclaimed in a soft moan.

“I love the way you taste, Liz,” he responded.

Gary then took my clit into his mouth and sucked on it as his tongue flicked against it. The combination sent intense pleasure throughout my loins and pelvis. I shuddered as he stimulated me.

He brought his hand up under his chin, allowing him to place his fingers at my vaginal opening, without ever disengaging his mouth from my clit, and began opening my vagina with his fingers. I could feel the lubrication from my vagina seeping out of me, and starting to trickle down the crack of my ass. I was wet and aroused, and my juices were flowing.

Soon Gary had two fingers inside of me, and was massaging the front wall of my vagina, at my newly discovered g-spot. The pleasure was almost too intense. I grasped at the bed covers as my entire body writhed, moaning loudly at the powerful combination of Gary’s sucking on my clit and his fingers massaging my front uterine wall deep inside me.

After only a couple of minutes of this intense stimulation, I realized that I was going to cum before we even made love, before he entered me. I brought my hands down to the sides of Gary’s head to guide his oral stimulation.

I started bucking my hips against his mouth. I took his head in my hands and held him in place as he continued sucking on my very sensitive clitoris. I moaned louder than I intended.

“Gary, don’t stop… shit… Oh God… deeper, push your fingers deeper into me… oh Gary, you are going to get me there… oh God… I am going to cum… don’t stop…” I babbled, almost incoherently.

I wanted to cum, I needed to cum; and cum I did.

A huge series of orgasmic waves quaked through me. I pushed my vulva against his mouth holding his head firmly in place. I was actually lifting my ass off the bed attempting to push against his fingers inside of me to get the maximum penetration possible. I was wantonly humping myself against my stepbrother’s hand and face as I had a violent orgasm. It was wonderful.

After the first series of orgasms rocked across me, my clitoris suddenly became too sensitive. “Oh, too much, you need to stop.”

And I pushed Gary’s head away from my pulsating vagina, breaking his suction grip on my clit. I could distinctly feel my pulse in my erect and swollen clitoris and I lay there trying to recover.

“Oh that was great… you were great. Thank you,” I said, as I lay there panting, my legs splayed apart, my vagina still experiencing periodic spasms.

The throbbing in my clit is so memorable, I get a bit wet even today recalling my level of excitement that evening.

Gary started to climb up between my legs now, his penis sticking straight in front of him. Now was the moment he had been waiting for. And like a good and skilled lover, he had already gotten me off before he attempted to fuck me.

I beckoned him into position. “Come here. Are you ready to take me?” I asked as provocatively as I could.

He simply nodded.

“Go slow. You are a lot bigger than your fingers. That cock of yours looks absolutely huge. Let me get used to it first,” I cautioned.

Then suddenly I had an idea. “Wait. Gary, lie on your back and let me put you inside of me first.” I wanted to control the initial penetration.

Without waiting for his response, I pushed against his chest and guided him to his back. His erect penis flopped over on his belly, making a slapping sound on his tight abdomen. It looked absolutely huge to me at the moment. Its length and girth were quite intimidating to this ‘soon to be ex’ virgin.

I climbed over him, straddling his torso. I raised myself up and brought his penis in line with my opening. Because of his substantial length, I had to raise myself up almost completely to get enough ‘height’ to place his head against my wet and dilated opening.

I rubbed his head up and down my wet and slippery slit. God he felt good against my clitoris.

“Liz, not too much of that. I am very turned on already. I down want to ‘lose control’ of the situation too soon,” Gary cautioned me.

He was well aware that too much stimulation and it would be ‘game over’ if he came too quickly. It was good advice on his part.

“Okay,” I said and I stopped stimulating the head of his erect cock against my clit and returned the head to the opening of my womanhood.

I looked his directly in the eyes and said, “Gary, look me in the eyes while I insert you. I want you to look at me while you take my virginity.”

I placed the head at my opening, and Gary reached up and cupped my breasts. I lowered myself about one or two inches, just getting he head inside me.

“Oh Gary, you are very thick. You are stretching me open.”

I could feel the ridge of the head of his penis distinctly pass through my tight opening.

“You are a very big man, Gary. You are stretching me.”

He penis pulsed as I said this, stretching me even further. I liked that feeling of fullness.

I held myself there, with maybe two inches of his penis inside me to savor the moment, as I watched the expression on Gary’s face. I wondered how far inside me he had to go before I was officially no longer a virgin. I guess once his head passed through my opening I had lost my virginity; but who knows what the ‘rules’ are?

I was wet and aroused, and dilated, but having just had an orgasm moments before I was not overwhelmed with passion at this moment. No, this was about taking this massive cock inside me and moving from virgin to experienced lover. And for once in Gary’s and my relationship, I felt like I was in control, as his penis edged its way inside me.

I raised up and then lowered myself slowly down, taking him further inside me, deeper and deeper, an inch at a time. I groaned as his thick penis stretched me open, penetrating me more deeply than I had ever been penetrated before. It definitely took some effort to force my tight pussy open enough to accommodate his girth. And forcing my pussy open felt both good and stressful at the same time. There was no real pain, but the stretching of my insides did have a slight discomfort to it the first time.

Once I had about six inches of his cock inside me I encountered some resistance and had to stop. I raised up again and very slowly lowered myself again, trying to take his entire length. I could definitely feel me adjusting to the size of this large intruder in my belly. The penetration quickly transitioned from discomfort to pleasure.

After repeating the up and down motion three times, each time stopping an inch or so short of taking Gary’s full length, I began to think Gary might simply be too long for me. I might not be able to take him fully in my tight pussy.

Gary was obviously growing more impatient and excited by the second. Suddenly, and without warning, he grabbed my hips and pushed me down as he thrust all seven plus inches of himself upward, piercing me deeply. The sudden penetration sent a shot of pain through my core and I let out a loud, uncontrolled ‘yelp’ in surprise.

“Oh Jesus!” I cried out. “You are so deep inside me. Hold still for a second! Please!”

I needed a second to adjust to this sudden and unexpected intrusion. Gary beamed with the joy of knowing his penis was ‘buried to the root’ deep inside me. The sudden pain subsided quickly. I could feel Gary’s erection pulsing inside me. I raised my self up and down slowly at first, tentatively determining how to maximize both our pleasure without pain.

Once Gary’s cock was fully inside me, my uterus seemed to simply ‘open up’ to accommodate this massive cock. The length and girth filled me quite fully. I raised and lowered myself several times and grew increasingly aroused from the internal stimulation.

I soon discovered that if I sat straight up, I could force the head to rub against the front wall of my uterus deep inside of me, stimulating my g-spot. God it felt good pressing up against my uterus so deep inside me. My movement became more pronounced. I was raising up, until only his head was inside my opening and then plunging myself down, taking him deep inside me. Gary would arch his hips and slap up against me as I plunged downward, making the penetration more vigorous.

I could feel my arousal building quickly as I matched Gary’s upward arches by plunging myself down on this huge penis that was buried deep inside me. I sat straight up, forcing the head against my front internal wall. I tried to gauge how deep he was inside of me, and came to the conclusion that he was deep inside me nearly to my naval.

I continued to ride him, to fuck him as my excitement grew and grew.

“Oh God, Gary… you feel so good… damn, you are going to get me again! Oh, fuck me, Gary, fuck me…” I hissed as yet another orgasm rapidly approached.

Gary continued to meet my downward plunges with violent arches of his hips, slapping his balls against my ass, pounding himself as deep as he could into my womb. I started to cum on his cock.

“Oh, God, I’m cumming… Gary, harder…” I begged and I shuddered and quaked as I humped, impaled as I was on his large cock.

In the middle of my orgasm, Gary flipped me over on my back, and assumed the top position. He began pounding me with a vigor and violence that I cannot describe. With my legs wrapped around his torso, Gary was pulling out and plunging into me, actually pounding my pussy into the mattress. And each violent thrust sent me over the edge again and again and again. I was having one continuous orgasm as Gary prepared for his own climax.

After only thirty to forty five seconds of this brutal pounding of my pussy by Gary’s rigid cock, Gary stiffened, buried himself deep inside of me, and began to spasm. The look on his face was a combination of intense anguish and pleasure.

He grunted as he pushed hard into me. I could feel his cock pulsing inside of me, and I knew my stepbrother was ejaculating deep in my uterus. I felt spasm after spasm of his cock, and I knew he was filling his stepsister’s vagina with ropes and ropes of his warm, sticky semen. His sperm were now inside of me, searching for an ovum that I sincerely hoped would not be there.

I lay there, my legs around my Gary, accepting his ejaculate inside my core. I enjoyed knowing that a most intimate part of my stepbrother was erupting inside of me as I held him in place with my heels on his ass. I felt my vagina spasm, milking his cock for every drop of his sperm. I wanted it all inside of me.

After erupting inside of me for several seconds, Gary relaxed on top of me. And I kept my heels on his ass, holding him in place. I did not want him to withdraw too quickly.

“Kiss me,” I demanded.

And he leaned forward and did just that. As we were necking, I clenched my vagina around his cock, which pulsed in response. I clenched around him several more times, milking his erection; each time his penis throbbed and pulsed in response.

The post-coital cuddling and necking was almost as pleasurable for me as the powerful orgasm that preceded it.

“Well you did it. You popped your stepsister’s cherry.” I smiled up at him.

“Yeah, I guess I did.” He smiled in return.

“You left me a little present in there too, didn’t you?” I clenched my pussy around him one more time playfully.

“It felt like I was leaving more than a little present. I don’t think I have ever cum that much. I think I pumped you pretty full,” Gary said, with pride.

“I imagine you did at that,” I said appreciatively.

 A sea of my stepbrother’s sperm swimming inside of me now. I do not know why I liked it, but I did.

We lay there for several more minutes as Gary grew less rigid inside of me. He eventually disengaged from me, leaving me feeling open and empty. My pussy spasmed involuntarily at the sudden emptiness it felt, as though it was trying to find something to grasp. It seemed to miss Gary’s penis immediately.

As soon as he withdrew, Gary, placed his hands on my knees to hold them apart as he inspected my dilated vagina for a moment. I could feel it continue to experience a series of minor spasms, and I could feel his semen leaking out of me under his gaze. I felt so wicked and exposed as Gary watched my vagina try to return to its normal shape and as he watched his sperm slowly seep out of his stepsister’s pussy.

“Whatcha looking at?” I asked. I was both embarrassed and excited being this exposed to my stepbrother at this moment.

“Your beautiful vagina and my sperm,” he answered with pride.

“You like knowing your sperm is in me, don’t you?” I asked.

He nodded and smiled.

He laid down next to me, and I fell asleep with my head on his chest. I awoke around midnight, and he had quietly slipped away to his own room while I slept. I reached down and touched myself, and found a considerable amount of spent semen still inside me. I brought a small sampling to my nose on my finger tips, and smelled the scent of my stepbrother as I lay there contemplating what we had done. I liked Gary’s scent, a lot.

And truthfully, though I knew it was wrong, I was enjoying the memory of our intimacy.