Category Archives: Virginity

E1 – Educating Young Natalie – Her First Time

Educating Young Natalie – Her First Time

By billy69boy

Chapter One

I’m not stupid. I see how everyone looks at me. And just because I haven’t really done anything yet, other than play with myself, I know a thing or two about sex. It’s not hard to find porn on the internet. It’s everywhere, and you don’t have to be 18 to see a lot of it, believe me. Plus, I found my daddy’s old porn collection in his closet, so I have a pretty good idea what sex is all about. I remember one time when I was younger; my laptop had some kind of a virus and was acting strange. When I booted it up, a picture of a blonde woman’s face appeared on my screen, out of nowhere. Her mouth was stretched wide open, and there was something dark filling it up…it looked like a great big tootsie roll, and I couldn’t figure it out at first. When I finally focused on it, I realized it was a black man’s penis that the blonde lady was gagging on. I jumped up, my eyes as big as saucers, and deleted that pic immediately! I was flabbergasted, and I put my hand over my thumping heart. My head was spinning, and I knew I had to get out of my room. I ran down the hall to the bathroom, sweating and breathing heavily. I splashed cold water on my face, and sat down on the side of the bathtub until my shock subsided.

While I regained my composure, I heard my mom calling me down for supper. I was relieved to have a diversion, and I didn’t even go back to my room first. Dinner was uneventful, other than my dad acting all strict, and asking me what I thought I was doing, wearing such a short mini skirt, even as the twinkle in his eye was so obvious, to me at least. I made a mental note to bend over for him later, so he could get a peek at my panties.

After I helped wash the dishes, I went to my room to finish my homework. As I tackled my math problems, I couldn’t get the image of that blonde girl out of my mind…well, not the girl, actually, but more like what she was choking on. I had never imagined any man’s cock could get that big. Finally, overcome with a young girl’s lustful curiosity, I put my pencil down, and turned my attention to my laptop. I went into my recycle bin, and retrieved that nasty picture. Only this time, I just stared at it; I couldn’t believe that girl could take so much of that fat cock into her mouth and throat. I was just mesmerized by its size, and the whole experience has greatly influenced me. I studied every inch of that picture, as my fingers twirled underneath my skirt. I was so wet already, and it didn’t take long at all to bring myself over the top. From then on, I secretly craved the idea of having some of that big black cock for myself someday.

I guess I should introduce myself: My name is Natalie. I am tall for my age, and I have long black hair and I’m told my dark eyes are mysterious. My body is still developing, so I’m still kind of flat chested. My ass is round and firm, but not very big yet. Still, I have long legs and a pretty face that is set off by my thick head of hair. Apparently, I am fairly attractive, because I get a lot of attention from adults, both men and women. I have even caught my strict, straitlaced father checking me out when he thinks I’m not looking. I secretly tease him by bending over in front of him, or “innocently” flashing him a glimpse of my panties when I’m wearing one of my miniskirts.

I love to wear short little skirts with tiny blouses, and I adore tight short shorts, because they show off my legs. I suppose I am rather flirty, in a naive sort of way. The truth is I get all tingly inside when I catch someone admiring my young, tight body. I’ve noticed my panties seem to get damp a lot these days, and I have been dying to try some sexy things for quite some time now.

I know they have laws against adults having sex with underage girls, and it is really frustrating. I get it that younger girls need to be protected from being abused against their will, but what about people like me who want to learn about sex? Doesn’t it make sense that I should learn from a trusted adult that I love, instead of some clueless schoolboy in a dark alley? I certainly don’t want my natural curiosity to get anyone in trouble.

I live with my parents, right down the street from my dear Uncle Roger and his girlfriend Sandy. I go down to their house to visit them quite often. Usually Uncle Roger and I watch TV together after school, while Sandy is at work. For years, I have enjoyed sitting on his lap as we watched our favorite shows. I discovered that, if I moved around just the right way on his lap that his man stuff would get hard as a rock, and rub against my panties. It felt good having something rubbing on my girl mound down there.

I love my Uncle Roger to death, and he always treated me nice whenever I came to visit. I know he loves me too, and he always makes me feel special. Lately, though, he has been making me sad and mad at the same time. After my usual fidgeting on his lap, instead of him letting me feel his stiffness on my crack, he would silently pick me up and put me down on the couch next to him. I looked into his eyes, and he seemed to get red in the face, almost like he was embarrassed. I was very frustrated and hurt, because it made me feel like he was rejecting me.

Finally, I figured it out on my own. Uncle Roger liked the feeling too, but he knew about the laws, and he didn’t want to take advantage of me and get into trouble. I became more and more obsessed with wondering how his hot cock would feel in my pussy. If it was going to happen, it would have to be up to me. I knew what I had to do now.

After school one afternoon, I went right to Uncle Roger’s house, still wearing my school uniform: plaid, pleated skirt, white blouse, white knee socks with saddle shoes, and of course my white cotton panties. My uncle got home early from work every day, and sure enough, I found him on the couch watching TV. I dropped my books on the floor, jumped into his lap, wrapped my arms around his neck, and kissed him on his cheek, before he knew what hit him. I told him how much I missed him and complimented him on his sexy blue shirt and gray shorts. I’d sat on his lap enough times to know he didn’t bother wearing underwear, at least not after he got changed out of his work clothes. He seemed a bit uneasy as I nestled into his lap in my usual way. Soon, we settled in, and I pretended I was interested in the TV show. In reality, my head was already spinning, and I could feel my heart pounding in my chest, as I thought about my plan.

It didn’t take long for me to feel his manhood swelling up under the thin material of his shorts, and I could already feel my own wetness between my legs. I moved around on his lap as subtly as I could, so he wouldn’t get all excited too fast. I figured we had an hour or two to be together before Sandy got home from work, and I wanted this to last. It was going to be a big moment in my life, and I wanted everything to be perfect.

Even with my gentle approach, it took only a few minutes before Uncle Roger picked me up and sat me next to him. I could see the big bulge in his shorts before he could cover himself with his hands. I was breathing so heavily by then that I was afraid he would notice, so I jumped up and almost ran down the hallway to the bathroom. I was so nervous; it made me have to pee. I took my panties completely off, and put them on the sink, then I peed. What a relief it was, and it helped me to calm down a little. I noticed my smooth pussy was soaking wet from something else, and I got such a rush when I wiped myself.

When I stood up, my legs were shaking as I washed my hands. I didn’t put my panties back on. Instead, I balled them up in my hand, and walked back down the hall to the living room. This was the moment of truth, and I was beside myself with anticipation, not really knowing if my plan would work. Without saying a word, I stood in front of my dear uncle, and put my hand in his. I pushed my panties into the palm of his hand, and closed his fingers tightly around them. As he raised his eyebrows, I sat down on his lap, facing the TV. Only this time, I lifted my plaid skirt up first, so my bare pussy was touching his shorts. I could feel his cock rising quickly as I slowly moved my ass around in circles. He didn’t move, as if he was paralyzed or something. Finally, I reached underneath and slipped his stiff meat out the side of his shorts and put it between my legs. I rubbed up and down on it, and the feeling of our skin touching was deliciously unbearable.

I leaned back on him, and I could feel his hot breath on the back of my neck, and his fingers running through my long hair. I reached down between my legs, took hold of his throbbing cock, and slipped it into my eager hole. I eased it in as far as I could, and it felt so good! I was a virgin, true, but there was no pain or blood, because I had broken my hymen playing with a hairbrush a long time ago. The feeling of having a real man’s big cock inside my body was just amazing, and I had an orgasm within the first minute. Despite the spasms I felt, I still tried to go slow, so as not to spook Uncle Roger, or have him go into panic mode, and try to stop me.

I put my hands down on either side of his hips so I could push my body up until only the tip of his cock was inside me, then I let go and fell onto his lap, as the whole length of his big rod disappeared deep inside of me. It was like nothing I had ever experienced before. I kept lifting up and dropping down onto his lap faster and faster, and soon I felt myself cumming again and again. I wasn’t holding back any longer, and I thrashed around on his lap, fucking him as hard as I could. Finally, I could feel his quivering penis explode inside of me, and I came again at the same time. He pumped me full of his hot cream, which made me so happy. I wasn’t worried about getting pregnant, because I hadn’t started that woman stuff yet that my mom told me about when we had “the talk”.

I stayed on his lap for a few minutes as we both tried to catch our breath. As I finally moved to get up, I felt like my life couldn’t get any better after what had just happened. But then, the front door burst open, and in walked Sandy. Startled, I jumped up and stood there awkwardly in silence. Sandy seemed to know exactly what had just happened, and the expression on her face was part smile, and part anger. She saw Uncle Roger’s hand move, and she couldn’t help but notice he was clutching a pair of white cotton panties rather tightly. She glared at him, and said something about dealing with him later, as she grabbed me by the hand, and led me to their bedroom, and closed the door behind us.

The Technician 2.0

The Technician 2.0

My mother is an attorney who tries cases regularly. Sometimes the judge wants the case sent to the jury the same day and holds court til the sun goes down before letting everyone return home.

It was Wednesday when we got home and saw the Technician who had installed our wireless network sitting in his Mitsubish Mirage in our driveway. Since my mother and I had discussed using him to take care of us girls when she was going to run late I was not surprised but Bethany had never met him.

We went to his car and I introduced my sister to him and he followed us to the front door. I pulled out my key and all three of us went in. He settled into the recliner my father used to sit in while me and my sister went into our bedrooms to get changed.

My sister and I share a bathroom. We went in there and discussed the Technician. Bethany said she thought he was handsome and wanted to know what kind of guy he was. She said "Daddy always made me make him cum first. Then he would make me cum." I explained that the technician was different because he made me cum twice before he tried to fuck me and in fucking me made me cum again." She asked."How big is his prick" I told er she was about the same size Dad had been. Maybe a little smaller but he knew things Dad did not know.

She asked me what to wear to get to him and I told her a tank top and miniskirt with no panties. So both of us dressed that way. We both came out of our rooms together and when he looked up he smiled.

I climbed up in his lap sideways and kissed him with tongue and he gave to me what I gave to him. His erection started to rise up under me. My little sister told me,"Could you make room for me please." Before I could move he lifted me and shifted me to one leg and he spread his legs to make room for Bethany.

Don't get me wrong I love my little ister but she can be a royal pain. She kissed him with tongue and he gave her tongue back. Then he started rub her flat little chest. Then he reached into her crotch and started to stroke her slit. I could smell her lubrication building up. He but his left arm around my lower back and pulled my skirt up to touch my pussy too. He slipped a finger into my pussy while staying stictly outside of my sister's virgin hole.

He asked which room we were going to do it in. My sister said,"My room please." He asked her,"Can your sister come and help?" I said,"Okay"
We retired to my sister's room and he took her clothes off and then removed mine. Then he stripped himself down to nothing but skin.

He laid down on my sister's bed on his back. When my sister and I climbed up on the bed he put her pussy right over his mouth. He pointed at his prick and I started to suck him. He ate Bethany until she came twice. Then he rearranged us.

He put my sister into a doggy pose. He told me to stand straddling her with my face pointing at her feet. Then he knelt behind her slipped the head of dick into her pussy. He went in and out about an inch but never broke her hymen. As he short fucked her he was eating me! He cock was working her cunt and his mouth worked my pussy. Both of us were cumming constantly from the intense stimulation.

Once when Bethany came he pushed himself all the one in one stroke. As he pulled out his cock it was stained red with streaks of white. He withdrew until only the head of his cock was inside her then he pushed back in until his balls hit her legs. He was still eating me and I noticed this in between my own climaxes.

She had not screamed or even flinched when he popped her cherry when she came out of her second orgasm she said,"Annette said it would hurt the first time but you did not hurt me at all. Did I tear my virginity out while masturbating?" The Technician reassured her and told her,"My cock is covered in your virgin blood so you were still cherry until right now."

That bitch came yet again after he brought her to orgasm while fucking her! I was slightly jealous. Then he came inside her but remained with her impaled on his stick until he softened and fell out of her. she went to the bathroom to douche as Dad had taught me and I followed her to help. When we returned to the bedroom he was dressing. It was just in time as we heard my mother's car pull into the driveway.

As she walked into the front door my idiot sister advertised her activity by going to meet her in the living room with a red and white drip of cum and blood running down her leg. Mom saw and and embraced her and asked, "Did the babysitter fuck you?" She told mother,"Yes, but it did not hurt at all? It was soooo good!" She looked up at the technician and asked him,"How did you make it not hurt?" He told her I took her cherry while she was in climax. The brain could not pick up the pain while feeling such pleasure."

She walked up to the technician and kissed him! with tongue! Then she said,"Well stud I guess I'll have to try you out some time. If you can perform with a grown up woman." He said,"I'll be able to do you just not tonight." She said,"I'm going to the prison to tell my husband we have replaced him as our stud. He's been telling me to find someone to do me and the girls and if you want to marry me you can move here."

"You can baby sit over the weekend and stay over from Friday afternoon until Sunday evening right?" He nodded his head.

He told her she would need to build a separate house for him on the back lot and he could live there and she and the girls would visit him regularly to have sex with until she could get him off the registry. He explained that he still owed over $500 of restitution to Blackhawk County Iowa for legal fees and court costs that had to be paid before he could get a pardon.

She said, "I can help with that." Then she asked him what she owed him for babysitting. He said "I don't think you ought to pay me considering what he had done with us girls but she asked me how long he'd been there. I said about 2 hours and she pulled out a $20 bill and handed it to him.

He turned to us girls and gave each of us a kiss without tongue as a good bye. When my mother said,"You can give them tongue if you want to." So he returned and kissed us both with tongue and a squeeze of our butt cheeks.
He then kissed our mother with tongue and left.

Once he was gone she went to her computer and to and got the phone number of the county clerk in Waterloo, Iowa so she could find out what if would cost to complete his restitution so he could submit his pardon application. We got dressed the rest of way and Mom made supper before sending us to bed.

I know tonight I'm going to dream out the technician fucking my sister and me. I hope he can satisfy my Mom so he can move within walking distance of us.