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JENNY’S VIRGINITY

Jenny is my sister’s daughter. She is now 17 years old and is turning into a very lovely young lady. Being 18 years younger than Sis, I have been her favourite little brother and have grown up along her own kid as a brother. I am now twenty years old and have been fairly close to Jenny all my life, having spent almost more time at Sis’s place than at my own parents’ place. However, it still came to me as a big surprise:
A few months ago, on the night before Jenny’s seventeenth birthday, I went over to hear what was planned for the next day. My folks had gone to some game lodge for the weekend and I was alone at home. Upon arriving there, I gathered that Sis and her husband were going out for the night and Jenny will be home alone. So, it was decided that Jenny would come over to our house and sleep over. Then I would take her back the next day and join in the birthday dinner. We stopped for some take aways and then went on to my folks’ place.

At home, we settled in the living room and decided to watch a movie. Jenny scanned through the TV guide and suggested a specific movie. I was surprised, as the movie she suggested, was rated 18 because of explicit sex and violence. That was not really the type of movie she usually watched. She, however, insisted that she wanted to watch this movie and so we did.

It was not a very good movie, but the scenes were really explicit. During one scene, I became very aroused and I glanced over to Jenny to see how she was experiencing this. She was still very naive as far as sex was concerned and I was convinced that my little Sis was still a virgin. She was watching intensely and I realized that she was aroused as well, because through her thin blouse, her nipples were standing up very clearly. Eventually, the movie finished.


“Not really good,” I said.

“No, not really” Jenny replied, “but there was a reason why I wanted to watch it.”

“Yes?” I replied inquiringly.


“Well, I want to ask you something big.”

“Oh yes?” I said, “and what can that be?”

“Well, hmm, I’m still a virgin, you know.” Jenny said.

“Well, I’d hope so,” I replied.

“Well, you see, I made a decision some while ago. I decided that I want to change the situation. I want to know what sex is like. The trouble is: I don’t have a boyfriend, as you well know, and I don’t want to have sex with anyone. I thought a lot about it and I came to the conclusion that, if I have sex, it must be with someone that I can trust and that will be able to teach me the basics about sex.”

“Hmmm” I said, somewhat perplexed.

She continued: “Well, as I say I thought long and hard about it. I think you are the best person to do that.”

“Hmmm” was all that I could say once more. I was rather bewildered by all this and needed some time to think.

“It’s OK, if you don’t want to do it. But the thing is, I know I can trust you. You won’t try to take advantage of me and you will be good to me, I know that. I know we are closely related and it shouldn’t really be done, but I don’t want a prolonged sexual relationship, I want you to show me and teach me once, then not again.”

“Well, this is a bit quick on me,” I said.

I looked at her. She was blushing profusely and seemed very embarrassed. I wondered what it would be like to hold her naked body in my arms and I was rather surprised to feel the warmth of arousal spreading through my groin and slightly stiffening my dick.

I got up and went over to my dad’s wine cabinet. I took out a bottle of champagne and proceeded to open it.

“Well,” I said, “tomorrow is your birthday and a celebration is definitely called for. I think the champagne would relax us a bit and then we can further consider your proposal.”

I poured two glasses and handed her one. I sat down next to her on the couch and” after we cheersed” we slowly sipped the delicious champagne. I thought to myself that I have a bit of a problem with our close family relation, but apart from that, I would not mind to have sex with this lovely young girl sitting next to me.

I topped up our glasses and tuned the radio set to some nice music. I looked at Jenny and immediately she blushed again and gave a little giggle.

“You are making me feel shy,” she said.

“Why?”

“I don’t know. Its because ... Ah, well, maybe I shouldn’t have said what I did.”

“About what?”

“About having sex with you.”

“Oh, well, I was just on the verge of agreeing to it.”

“You were?” She looked at me, her eyes wide.

“Yes. I thought about it this last 15 minutes or so and I think that, after all, it is not such a bad idea that I teach you a bit. So often it happens that the guy with whom the girl has her first sexual experience is not considerate enough and then the girl has a bad experience and thinks sex is not nice. I’ve heard that quite a few times. I also did some research on the matter.”

“You did research?”

“Yes. I did some reading up on how best to go about the first time with a virgin.”

“Now what is different with a virgin?”

“Well, there are quite a few things that the guy can do to make it less painful and nicer for the girl.”

“Well, then you really are the right person” Jenny said smiling naughtily at me.

She looked so cute and sexy that I could not resist it any longer. I reach out and pulled her into my arms. She turned her face up towards me and I kissed her. Her lips were parted and her mouth hungrily accepted my searching tongue. I could feel her heart thumping rapidly against my chest and she was breathing quite quickly. One thing was sure: this girl was turned on, very much turned on.

After a few minutes of passionate kissing, I slowly lifted my lips from hers and smiled at her. Her eyes were still closed and her lips parted.

“Let’s got to my bedroom” I said, “its easier on a bed.”

I got up and pulled her to her feet. While walking I could feel how my hard-on was straining against the cloth of my underpants. I looked down and saw that there was a huge bulge at the front of my pants. I pointed to it and said: “Just look what you are doing to me!”

She blushed again and giggled again. In the room, I took her in my arms again and, standing upright, we kissed again. Our bodies were thrust firmly against each other. I let my hands roam over her back caressing and stroking her. My Left hand slid down to her cute round bottom and I pulled it hard, thrusting the swollen knob at the front of my pants into the softness between her legs. She groaned and returned the thrusting, pushing her hips forward and holding my bum with her one hand. For quite a while we stood like that, kissing and rubbing our sex organs against one another’s.

Then I slowly turned sideways, still keeping the kiss in tact, but allowing some room between us. While firmly rubbing her buttocks with my left hand, my right hand slowly moved over her shoulder and proceeded to caress her throat and then went down to her left tit. I fondled the lovely tittie in my hand, completely enfolding it. Then I took the nipple, which was already completely erect, between my thumb and forefinger and gently rolled it. Jenny moaned loudly. She brought her left leg round and gently lifted her knee, pushing it between my legs. I continued to play with her small firm tits, concentrating on the nipples, but also rubbing them and squeezing the full tit.

Then I pulled her square against me, once more. Immediately our hips started thrusting one another again, but this time both my hands slid down to her bum. I got hold of the fabric of her skirt and pulled it up. My hands closed round her firm buttocks only separated from them my a bit of cotton. I pushed my hands into the back of her panties and firmly grabbed hole of her buttocks, my fingers pushing deep into the crack between them. I pulled her against my groin, at the same time arching my hips forward. She pulled her mouth from mine and gasped. “My God, you making me wild” she said, still gasping.

“I’m going to make you much wilder still” I said, releasing the pressure and reaching forward. I slowly pulled her panties down to her knees. Then I reached up and pulled her skirt down. She worked the skirt and panties down and stepped out of them. I moved away a few inches and looked down at her crotch. The darkness between her legs was emphasizing the triangle of light auburn hair disappearing in that secretive darkness.

I looked up at her face. She was smiling. “Do you like what you see?” she asked.

“Absolutely, but I want to see it all” I said, beginning to unbutton her blouse. She, in turn, began to pull my t-shirt out of my pants and lifted it over my head. I pushed her blouse back and she moved her arms down, letting the blouse drop behind her. I reached round her and fumbled with the hooks of the little flesh coloured bra. She lifted her one hand behind her and quickly did it. The bra slid down, revealing those beautiful small tits. I stared at them for a few seconds, completely spell-bound. Then my hands were drawn to them, as if a pair of invisible hands took hold of them and pulled them there. She gasped as both her nipples were simultaneously gripped between my fingers. She reached down and unbuttoned my pants, blushing as she did so. I closed my eyes and pretended not to notice her embarrassment. I felt my pants come loose and she pushed them down as far as she could reach. I continued to massage her lovely titties, while she hesitated for a long time. Then I felt her fingers hooking into the top of my jockey alongside each of my hips. Then she slowly pulled them down. When the jockey was pulled down far enough, my dick, which was aching with strain, jumped up like a jack in the box. Jenny giggled and said: “Gosh, its huge!”

I opened my eyes and smiled at her. “Yes,” I said “I’m lucky to have a size well over the average.”

She looked a little shocked and blurted out the next moment: “Wouldn’t it be too big to …… hmm, you know, hmm, to go in there?”

I gave a little laugh and then said as reassuringly as possible: “No, no. You know a baby can come out of there, then surely, this guy can fit in there.”

She tentatively put out her hand and touched my throbbing dick. She stroked it gingerly, clearly not knowing what exactly to do. I showed her how to grip it in her palm and jerk it back and forth. She giggled again as she pulled the skin back to reveal the purple head glistening with pre-cum. “Its wet!” she said.

“Yip” I replied, “It should be. That is to lubricate itself when has to go inside you. I’m sure you are also getting wet?” With that, I slid my right hand down to her crotch. She opened her legs, but I decided not to touch her pussy straight away. Rather, caress the pubic hairs and then slid my hand down to the inner part of her right thigh, slowly moving it and closer to her pussy lips. She parted her legs wider and leant against me. I moved my hand to her left thigh and I spread my fingers wide pushing against both her groins. She opened her legs ever wider, bending her knees. Very gently I touched the hairs covering her pussy. She breathed deep and quick. Then, suddenly, I grabbed her whole pussy with my full hand. She gave a little shriek and then followed it with a long, deep moan. She moved her hips rubbing her pussy on my hand. Indeed, her pussy was quite wet, especially when I pushed my fingers into the slit between the lips. She let out another shriek when my fingers found her clit. Gently, I caressed her clittie, causing her breathing and moaning to become ever louder and louder.

Then I remembered the caution from the book I read on the way to treat a virgin: “all the preparations should be done before the female is brought close to orgasm.” That is to prevent the situation where too much time elapses without stimulation, causing the female to lose her peak and making it difficult to bring her back there again. So, I let go of Jenny’s body and said: “I better put on a condom now.”

“You don’t HAVE to,” she said, “I’m using the pill.”

“Okay,” I replied a little surprised. “It is nicer without it.” She later told me that she had the pill prescribed because of a skin problem, which was hormone, related. I took a thick, firm pillow and put it in the middle of the bed. Then I turned to Jenny and picked her up in my arms. Kissing her passionately once more, I gently laid her down on the bed with her bottom resting on the pillow that I had arranged. In this way, her hips were raised much higher than the rest of her body. This was also recommended by the book. This position enables the male to push his penis into the vagina pressing it from below up against the front of the vagina. This, apparently, is the method causing the least discomfort. I knelt down on the bed next to her and slid my right hand in between her legs. She opened them wide and I gently placed my hand on her warm, wet pussy. She moaned again. I moved my mouth from hers, gently nibbling at her chin, then her throat and slowly working my way down towards her tits. She was gasping and moaning loudly and when my lips closed on the nipple of her right tit, she shrieked again. Now I quickly moved my mouth from one tit to the other, sucking and softly nibbling at her nipples. My right hand was rubbing her clit in a circular motion. She put out her right hand and closed it firmly round my throbbing organ. Thus we continued for a few minutes, until I thought she was quite close to an orgasm.

I quickly got into position between her widely spread legs. Momentarily, I stared at the fantastic view: this beautiful girl, lying there, naked as a new-borne babe, her nipples hard and wet, her pussy glistening pink like a ripe fruit. I leaned forward, supporting myself on my left hand and with my right hand I guided the tip of my member into the opening of Jenny’s vagina. I lowered my hips and began to push forward and upward, slowly and smoothly penetrating her, until my pubic bone pushed against hers. The feeling was almost indescribable: her pussy was so hot and so wet and quite tight round my thick dick. I moaned and then looked down at Jenny’s face. Her eyes were closed and she was smiling.

“You are not a virgin anymore,” I said. She didn’t answer, but the smile broadened.

“Does it hurt?” I asked.

“Its just stinging a little,” she said, “but it is okay.” I immediately began pushing my crotch against hers, moving my hips in a circular motion. I did not pump in and out of her like I usually did when fucking. This was also an instruction from the famous book. It suggested that the male uses this method to prevent too much friction on the broken virgin. In this way, the pubic bone of the male rubs against the female’s clit, enabling him to bring her to a climax. She was moaning softly and I turned my head and reached for her left nipple with my mouth. Because of the low posture of my body my head was below hers, but I still had to pull her tit towards my mouth with my right hand. She moaned loud and open-mouthed as my teeth gently nibbled at her nipple. I kept up the rotating movement, pressing firmly down and forward. I yearned to resort to the normal pumping motion, because it felt like my dick was teased, not getting the level of stimulation it was expecting, but I restrained myself and just kept on working my hips around and around. Jenny was definitely approaching an orgasm. I could tell that from the intensity of her moaning. She was rolling her head slowly from side to side, her mouth wide open, uttering low throatal moans. Then she grabbed my shoulders with both hands, the nails digging into my skin. She was moving under me. Suddenly, her whole body tensed. She pushed her hips upward and gripped me very tightly. Then she began to shake and at the same moment she let out a loud, primitive scream, her head bend over backwards, her mouth wide and her tongue halfway stuck out. For several long moments she kept on shaking and I ground my pubic bone hard into her pussy. Then slowly, she began to relax, sagging back on the bed. She was panting and then she said”

“Oh my God, oh my God!”

“What is wrong?” I asked.

“It is SO good, so good, I can’t believe it,” she said. “I have never felt anything like this.”

I kissed her gently on the lips, then on each cheek, then on the lips again. My dick and balls were aching with the desire to orgasm. I thrust my hips against her firmly. “I want to come inside you,” I said, “but if it hurts, you must tell me.”

“Okay,” she said softly, smiling at me. I kissed her and began to rotate myself on her, once again. Gradually, Jenny got excited again. First, her breathing became deep and raspy, and then she began to produce low moans once more. However, my climax was coming on and I decided not to hold it back. Suddenly, I felt the orgasm gripping my body. My balls contracted and my liquid blasted out deep inside Jenny’s pussy. I let out a loud groan. Several shots fired inside her, diminishing in strength every time, until it subsided. I sagged down on her, my body becoming limp.

“I could feel it inside me,” Jenny said, “its weird.”

“That’s the baby-making juice,” I said. She gave a little giggle. I lifted myself back on my supporting hands and kissed her softly. “I’m going to make you cum again,” I said, moving backwards and pulling my dick, still hard, out of Jenny’s pussy. I moved right back and then leant forward, lowering my face on her open pussy. As I placed my mouth on her pussy, pushing my tongue between the lips, she said somewhat shocked:

“You can’t kiss me there!”

I briefly lifted my lips off her wet pussy and asked: “Why not?” immediately resuming the pussy kiss.

“Its not clean!” she said.

Again, I briefly lifted my head and said: “It smells and tastes like honey to me.” I reached up and took her nipples between thumb and forefinger. She resigned herself to my attentions and soon she was moaning with enjoyment. My tongue circled and massaged her clit, flicking rapidly over it. Occasionally, I sucked her clit into my mouth. This seemed to give her extreme pleasure, because she moaned loudly and moved her body every time I did that. My fingers worked her nipples ever faster. It did not take long before Jenny’s body went into an orgasmic spasm once more. Again she screamed like a wild animal. When she finally relaxed, I moved over to her side and drew her into my arms. She snuggled against me. For a long time we lay like that, just holding each other.

We spent that night naked together, talking, sleeping and playing with each other. We did not have more penetration, as Jenny’s vagina was too sensitive, but we played a lot. I taught her how to give a good blowjob and I muffed her to several wild climaxes.

That is how my little “sis” lost her virginity. Thinking back about that night, I sometimes feel a little guilt, but then I atone myself with the knowledge that it really had done her well: She met a nice guy a few weeks ago and they have been going out ever since. Just yesterday she told me that they had had their first intercourse the night before and that it had been absolutely wonderful. She gave me a big brotherly hug and said that she would always remember that night and that she would be forever thankful for the way I had gently introduced her to the wonderful world of sex.

THE END
100 comments

anonymous readerReport

2011-12-22 12:53:38
Loved it but hoped that the experience was so satisfying that she wanted him to continue forever! 8 out of 10 though....Nice!

anonymous readerReport

2011-08-23 10:44:44
I went on holiday with a family who's daughter was fourteen but very attractive. She told me on the plane that she was a virgin and I could be the first to fuck her if I wanted. Two days in and she and I were in my room in the afternoon and completely naked. She had nice tits and a nicely shaved cunt with just a strip of black hair. She kept telling me that I had to be gentle with her and I promised I would. We went in the shower together and I got one and then two fingers into her, I noticed at this time how very nice her cunt tasted and got her on the bed with her thighs apart as soon as seemed decent. I licked her tasty cunt until she was squirming and then pushed my cock into her. She was tight at first and then loosened up until her hole was bigger than her mums which I'd fucked many times. She was very sexy though and fucked with me throughout the holiday and for some time after. She later told me that her first fuck had been when she was 11 and she'd had plenty of cock since the

M`ster123Report

2011-08-23 03:15:05
haha! idiot! jb, seriously? dream on. great awesome story by the way. and why is it so sick 2 fuck a family member? it said incest on the tags yaknow.

anonymous readerReport

2011-07-03 21:15:37
orid an omarisa aljins

anonymous readerReport

2011-05-23 12:17:06
My first time is gonna be with with jb

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