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Elizabeth's Story - Chapter 6: How Far Should We Go?

"Gary wants to take my virginity and I am not sure what to do..."

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After a very, very exciting weekend of sexual discovery and inappropriate behavior, Gary and I started to settle into a routine of mutual masturbation, humping and oral sex. We were both in a constant state of arousal, hormones surging through our young bodies. We were behaving like the sex crazed teenagers that we were.

Mom did not seem to detect any change in our behavior; at least she did not demonstrate any suspicion towards either Gary or me. Mom stayed with her routine of drinking herself to sleep each evening and was snoring loudly by nine o'clock every night; opening the window of opportunity for Gary and me to play nasty-doctor-and-naughty-nurse each night after she went to bed.

As soon as I was in my room alone and Mom was asleep, Gary would make a beeline in to see me. He would enter my room, unannounced and uninvited, with his shorts forming a tent in front in anticipation of the games he planned to play with his stepsister. I would also become aroused, wet with anticipation like Pavlov’s dog, each night waiting for my stepbrother to enter my room.

In some weird and illogical way, waiting on Gary to come to me, rather than going to his room seemed to reduce my guilt ever so slightly. I was not imposing myself on my younger stepbrother; I was merely submitting to his desires as he entered my room uninvited. Silly? Absolutely. But I would take any slight reduction in my culpability, no matter how ill-founded the logic was.

Gary always achieved an orgasm during our sessions, often more than once. I typically would have a climax as well, but not always. Gary loved having me make love to his penis with my mouth, and honestly, I enjoyed tasting and swallowing his semen. I found the very thought of swallowing his semen, ingesting it, and having it inside me strangely fulfilling and emotionally satisfying.

Making my stepbrother cum in my mouth had a unique balance of submission and control that stimulated me. While it was true that I was submitting to him, I still maintained control by arousing him and getting him off. I found that liked giving head.

I loved having Gary pleasure me with his tongue as well. I loved the feel of his fingers inside me as he sucked and teased my clitoris. I almost always had an orgasm that way.

Very early in our sessions, I learned that I needed to achieve my orgasm before Gary achieved his, or it was 'game over' for Gary. He lost interest in making me cum once he ejaculated; whether in my mouth, in my hand, or on my belly. So typically, Gary would have to wait for his blow job until he took care of his big sister. We both were fine with this arrangement.

All-in-all, the physical part of our sibling games was good; very exciting, very convenient, and very fulfilling. Emotionally, I was still torn. I was ridden with guilt, and shame. It was difficult to have an experience that was so pleasurable, so satisfying and exciting, and so all consuming; but yet was so shameful.

While I felt incredibly close to Gary, in many ways our relationship isolated me from my friends. There was no one I could talk to about my wonderful discoveries. If anyone were to find out, life as I knew it would come to a screeching halt. And knowing that if any of my friends knew what Gary and I were doing, I would be labeled a pervert or a monster, placed a heavy burden on my emotional well being.

All day, every day at school, I was highly distracted. I seemed to be constantly wet and aroused either thinking about what Gary and I had recently done, or in anticipation of what we would do that evening. I noticed that by the end of my school day, the crotch of my panties was damp with the constant leakage from my aroused vagina. Prior to Gary and my discovery of each other, this had not been an issue for me. Yes, I was lubricating all day long.

I also realized that my grades would suffer if I could not gain back the ability to concentrate on my school work. This thought troubled me.

I wondered if the boys around me could somehow sense my arousal and my wetness. Like animals in the wild; could they sense a female in heat? The boys did seem to be noticing me more and talking to me more than in the past. Or maybe I was more aware of them. Regardless, I did feel as though I was ‘in heat’, and I wondered if others could detect my arousal.

I know this may sound slutty of me, but I also started to wonder what sex would be like with other boys. What did their penises look like? Did they respond the same way Gary did? Did their semen smell and taste the same as Gary’s? I could not help these wicked thoughts I was having; these thoughts just seemed to enter my mind uninvited. And once in, I could not purge these thoughts.

In physics class one day, while sitting next to James, a boy I had a mild crush on, I constructed a entire fantasy of me going down on him behind the bleachers while the teacher rambled on and on about conservation of momentum. Although I barely heard a word of the lecture that day, I felt it was ironic that the fundamental premise was that once a body is set in motion, it will continue on that path until acted upon by another force. And my body was on a path of sexual awakening and discovery!

Then there was the whole intercourse question and decision. Gary was anxious to advance our activity to include penetrating me with his penis and he was pushing me hard in that direction. Gary wanted me to either go on the pill, or he wanted me to agree that we could have intercourse if he got some condoms. So far, I had been non-committal on either option. I just was not yet ready to lose my virginity, and when I was ready, I was not sure I wanted it to be to my younger stepbrother.

It was Thursday night, after Mom had shut it down for the night, Gary entered my room and introduced the subject once again. I was wearing a sleeveless shirt and panties as my poor girl’s pajamas. Gary and I were past the point of any modesty around each other, so my level of exposure did not present any issue for either of us.

“Liz, you really need to go on the pill. There is no down side. And then when you are ready, you’ll be ready.” Gary was trying hard to seem rational and reasonable, rather than self-serving with his arguments.

“Gary, that is a big step. And honestly, I don’t know if that is something we should do now, or ever. So far we can claim we are playing around the edges. We hadn’t sealed the deal, so to speak. And what we are doing now is plenty satisfying for both of us; at least it is for me. It is way more excitement than most kids our age have.” I was talking to myself as well as to Gary; trying to convince myself that we needed to keep this last remaining boundary in place.

“Liz, I am never going to love anyone more than I love you right now. I want you to be my first. And I sure cannot stand the thought that some other hard dick son-of-a-bitch at school will be your first. That would kill me. I want us to experience this together.” Gary sounded sincere. He also sounded possessive. This concerned me greatly.

“Gary, you do realize that both you and I will date other people. We will marry other people. You are going to have to be okay with me being with other guys; and I will have to be okay with you being with other girls.”

I was concerned that Gary did not understand the limits of our relationship and where it could, and could not lead.

“Liz, I know all that. I am not stupid. I know I am not going to marry my stepsister, or even take her to the prom. But we are closer than any brother and sister we know. We have already shared things most brothers and sisters never even dream of sharing. I know things about you, your body and what arouses you that nobody else knows.”

Gary paused to let the passion in his voice subside a bit before continuing. “Each of us will only have one ’first time’. I think that we should have it with each other. I do not want my first time to be with the first slut from school who will let me fuck her; I want it to be with someone who loves me, and who I love. I want it to be with you.”

I was overwhelmed with emotion at Gary’s speech. I actually started to cry. I tried not to; but the tears simply formed in my eyes, and were soon running down my cheeks.

“Oh God, come here.” I beckoned him to the bed where I was sitting. I hugged him tightly as he sat next to me. “I love you so much. You are right, it should be you; no one else.” Gary reached up and cupped my breast as I hugged him, gently teasing the nipple to becoming erect. I kissed him and his tongue parted my lips.

I broke the kiss, to continue my response, as Gary continued to tease my nipple. There is something very sexy associated with a young girl being felt up while she talks to someone. I mean looking my stepbrother in the eye, and trying to articulate my thoughts while Gary fondled my breast was uniquely arousing and sexy; it was an intimacy that I did not experience again until after I was married to my husband, Robert, many years later.

“Okay. Tomorrow I will go to the clinic and get on birth control pills,” I relented. “I want to give myself to you. I want you to take me; to take my virginity.”

Tears continued to stream down my cheeks and on to Gary’s shoulders and chest.

“Sis, why are you crying?” Gary seemed obviously confused by my sudden outpouring of female emotion.

“Because I am silly; because I am so conflicted about what we are doing; because I just decided that my stepbrother is going to deflower me; because I am feeling so much love for you right now; and because of a bunch of things.”

I was having such an emotional release that my tears continued to flow as I kissed Gary again.

“Deflower?” Gary asked with the most puzzled look imaginable.

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He obviously was not familiar with the term.

Gary ’s look of bewilderment struck me as quite comical and I released a loud laugh. I looked back and realized I was losing my grip on everything. I was hugging my brother while he fondled my breast, crying and laughing all at the same time. If someone had seen me, they would have locked me up. Literally, they would have locked me up!

“It means take ones virginity. When you enter me for the first time, I will no longer be a virgin. You will have ‘deflowered’ me. You will have popped my cherry, so to speak; although you actually ruptured my hymen with your fingers several nights ago,” I explained to my slightly naïve brother.

“I ruptured your hymen?”

“Yes, the first night you came into my room, when we were humping on each other and you were sticking your fingers into me so deeply, I felt a sharp pain inside me and I think you broke my hymen.”

I looked at his reaction and I saw no remorse. In fact, he seemed to be a bit proud.

It was yet another educational moment about the male psyche; it seems that all men have an uncanny desire to ‘mark their territory’, to leave a mark claiming what they perceive as theirs. And breaking my hymen was just one way for Gary to mark me with a Gary-was-here-first marker. He obviously liked the thought that forever more, he would be the one that broke my hymen. And now he wanted to claim my virginity too. And I had just agreed to let him!

Yes, Gary’s face simply beamed with joy and excitement. I had informed him that not only had he ruptured my hymen, but I had just agreed to let him deflower me. Yes, Gary felt like he won the lottery. I wonder how many girls lose their virginity in such a planned manner?

Gary reached under my shirt to contact my bare breast. And we kissed passionately. We were proceeding to our before-bedtime-romp; but tonight was special. Tonight I was highly emotional. Tonight I was in preparation, both mentally and emotionally, to give myself to Gary as soon as I could secure my fertility and protect both of us from an unplanned and unwanted pregnancy.

Gary pulled my shirt over my head, leaving me bare breasted. I wearing only my now damp panties. I, in turn, removed his shirt and immediately started removing his gym shorts. His penis was already rigid and strained toward the ceiling like a proud solider standing guard. I took his rigid tool in my fist; oh, how I loved the feel of this erect penis.

Gary stripped off my panties with my assistance. I lifted my bottom off the bed to allow him to pull them down past my legs and ankles without letting go of his erection in my fist. This was my penis and I was not letting go of it!

Gary looked at my naked form with clear admiration. I allowed his eyes to devour my perky breasts and vagina for a moment. My vulva was barely concealed with a very thin covering of fine blonde pubic hair that seemed almost translucent.

I leaned forward to take Gary’s penis in my mouth for just a moment; to taste him and to allow him to feel my tongue around the ridge that separates the head from the shaft. Gary moaned appreciably as I took the very tip of my tongue and probed the tiny little opening to his urethra gently; his penis arched up as my tongue penetrated this tiny slit on the head of his cock. I liked his reaction to that and decided I would do it again. I was learning all kinds of tricks.

As Gary laid on his back on my bed, I kissed and sucked his erection. He began pulling and guiding me over him, directing me into a ‘69’ position. Now quite honestly, I did not immediately understand what Gary was doing, or what position he was trying to get me to assume. But after lifting my hips and raising me to be on all-fours, Gary wedged his head and shoulders underneath me. It suddenly dawned on me in a position that allowed Gary to suck on my clitoris while I sucked him.

Once I understood what Gary wanted, I began to embrace the idea. I lifted my one leg over his head and I straddled his face without removing his erection from my mouth. In this position, Gary reached his hands around behind my legs and his fingers found the wet opening of my vulva. His mouth and lips found my erect clitoris. My mind was racing from the excitement of being eaten while simultaneously sucking on Gary’s magnificent cock.

Gary pulled my pelvis closer to his face, separated the lips of my vulva and teasing my clitoris with his tongue. I moaned with pleasure around the head of Gary’s erect cock. He then gently took my erect clitoris into his mouth, sucking it gently like it was my third nipple. The sudden rush of pleasure that shot through my loins evoked another loud moan around his throbbing cock. I pulled his penis out of my mouth for an instant, and exclaimed, “Oh my God, Gary, that feels good.” I then quickly returned to servicing his erection in my mouth.

Gary was now pulling my vulva open with his fingers and began massaging my entrance and penetrating me with the tips of his fingers. He had both his hand around my backside, pulling my vulva open as he probed his fingers into me. I think he was penetrating me with one or two fingers from each hand but I really could not tell how many. He sucked on my highly sensitive clitoris.

I moaned loudly around the head of his cock each time Gary sucked my clitoris into his mouth. I had never felt so sensitive down there. I knew I could not hold my orgasm back long with this extreme stimulation. I would cum quickly. Each time Gary sucked my clitoris into his mouth with his tongue, it felt like my clit might actually burst it was so swollen. My little nubbins felt like it was growing bigger than it had ever been. God I was aroused and I loved what Gary was doing to me.

Gary’s fingers were probing my vagina more deeply now. I think he had two fingers from one hand massaging the front wall of my uterus while one finger from the other hand stretched my opening wider and wider. I had three fingers inside my tight little virgin pussy and I was bucking wildly trying to allow them to probe me deeper and deeper.

As my excitement grew, I could feel the orgasm building inside me. I started humping violently against Gary’s mouth and tongue, and pushing back against his fingers. I was taking his erection more deeply into my throat than I ever had before as I approached my climax. I was out of control and I could not help myself. I was all but screaming around this massive erection as I attempted to take him further into...

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