Older man teaches teen how to fuck (m/f) | 2016

Recently i was with some GF's and the subject of our first times came up. It made me want to tell my story here. I usually just read funny stories on here, but i decided to make a profile and share this. Enjoy. I did!! I am a 41 yr old female in the US. I am half asian/white. I started to develop pretty young and at 4teen I was a C cup and by 6teen i was a full 34D. I was 5' 4", 120 lbs and 34D at 6teen. Brown hair and eyes. An older family friend, Mike, had always liked me and flirted with me early on, I liked the attention and didn't think much of it. He was a really big guy too, 6' 5" and a big man, not fat though. One day i was over his house with some of my family members and for a reason i cant remember today, i ended up alone with him at his house in my C cup phase.

I think he was supposed to drive me home but i wasn't really concerned either way. I can't remember the particulars but at one point we were wrestling and before I knew it he went right for my breast. I was totally shocked, but he moved fast and quickly had my right titty out and went right for my nipple. I instantly got really turned on and just let him do what he wanted. It was so erotic and felt wonderful. "Jennifer, you have perfect tits sweetheart, do you like how this feels?" I shook my head yes, i was still shocked and couldn't really talk LOL. Then he said, "let's see how much you like it."

He put his hand down my jeans and down my panties and he was quite surprised. "Oh my Jennifer, your pussy gets so wet." I was so turned on, he could have taken me right there and i wouldn't have protested. So, obviously i was enjoying what he was doing. This went on for a few minutes, but he knew i was too young and took me home.

Nothing happened for two years until he saw me at age 6teen in a bikini. Again things picked up between us. He played with my pussy as much as he could and loved sucking my tits. It was so hot, I got so wet each time. I would go home at night and rub my pussy thinking about it and would quietly cum in my bed at night. I often felt his bulge in his pants and wondered what it would look like, and would it would feel like. I had no idea that a monster was in his pants. Finally one day, we were at the lake, of course i was in my little black bikini, none of the friends and family knew what was going on. Every one went to their tents and i stayed up, hoping he would get me into his tent. (all day i was teasing him and i knew it).

He gave me the wave as if to say, my tent, now. Of course i went. Once i went inside his tent, he went right for me, he couldn't take it anymore. He took my bikini top off and started sucking my tits really hard, i was breathing heavy, i was ready. He pulled my jean shorts off and my bikini bottoms. It was the first time i was in front of anyone totally naked. He made me so comfortable cuz he kept squeezing my ass and tits telling me how perfect i was. My pussy was absolutely soaked, i was so wet i was actually a little self conscious about it. "He laid me down on his sleeping bag and then stood up, pulled down his shorts and stepped out of them. I didn't know it at the time, but, he was (9.3 x 6.2) 9.3 inches long and 6.2 inches in circumference (much fatter than a toilet paper roll). I would later measure him and learn those dimensions. But that first time seeing it, i didn't know it's dimensions, i just knew it looked HUGE, and it made me really nervous. He could tell by the look on my face i was really concerned. "Jennifer, don't worry, we will go slow." He kneeled down and put my legs the way he wanted. "Keep your legs spread as wide as possible sweety." He could hardly wait. There i was, his busty asian virgin teen laid out for him to take. He told me, "look at me, i want to see your face the whole time." Then he put his cock tip to my pussy lips and slowly started to push in, just the tip. I was like, "oh, this isn't so bad." LOL, if i only knew... Then he touched his tip to my hymen, "ohhh jennifer, i feel your little gift on my tip, are you ready?" I shook my head yes.

Then he slowly and gently started to push, my mouth opened up and OHH MY did i feel pressure. He was pushing, but his cock was not traveling anywhere. He kept pushing and pushing, but still nothing. Then he backed out till the tip was just on my lips again. "Jennifer, do you use tampons?" No i said. "Have you ever put a finger inside your pussy?" No I said. (he did not either, in the handful of times that he played with my pussy before this, he never inserted a finger inside me). Like me when i would play with my pussy, he only rubbed the lips and clit.

Then he realized, his cock would be the very first thing, ever, that entered my pussy. I could see the look on his face. He loved this reality. "Jennifer, i am going to have to thrust hard to break your cherry sweety, it will be a little painful. Then he started to rub the tip up and down my lips, i was so wet, i wanted it bad. Then, he looked down at my pussy, then into my eyes and pushed really hard, i screamed out, he covered my mouth and did it again, then again, i started to cry a little bit. "shhhhh" he said. Then finally, he broke through my cherry, it was the most amazing and intense feeling. He was squeezing my ass then tits, then only my tits looking at my face the whole time. He got about half ways in and started to pump slowly, my pussy was on fire but it did feel a little bit good too. He couldn't take it though and knowing what i know now, but not then, he was trying not to cum, but he couldn't hold it. It was just too much for him; the totally virgin pussy, my 6teen yr old 34D breast bouncing everywhere, my moans and screams and tears...and he just exploded his cum. The first couple squirts went right inside my virgin pussy, then he pulled out and just came all over my pussy hair, belly and breast. He gently pulled out, and i could feel my lips holding on to his cock and squeezing it as he pulled out, and the way he was wincing i knew he could feel the same thing. He looked at his dick and my popped cherry was all over his shaft and head. I could feel his cum leaking out of my pussy and the blood from my popped cherry was running onto my cheeks in my crack (that felt kinda weird LOL).

Then he did something that would continue for the first several times, he wiped his bloody cock on the inside of my thigh. Smearing it clean.

He knew i had to get back to my tent, because although he covered my mouth, he couldn't totally silent my moans and screams. I went back to my tent and tried to sleep, thinking about what had happened. When i woke up the next day, my lips were very swollen, visibly swollen and of course there was the blood mark on my inner thigh. The next time we did it was at his house. I went over after school. He led me to his room and he continued to break me in.

I wore tight jeans, a tight white sweater and little white panties. He only got about half way the second time as well and again my pussy bled. I remember after that second time he was standing up and i was laying on the bed, again covered in his cum. He was getting soft and his thick cock was hanging a little bit, again with my blood on it. It was so erotic watching him standing there, knowing that i made that cock cum that much. He had wiped his cock again on my thigh, but he didn't smear it all off. So he grabbed my white panties and wiped it clean, staining my panties.

It took him about 8 times before he finally got all the way inside. I bled a little bit each time until he got all the way in. Once he did get all the way inside, it was sooooo hot. He would slowly fuck my pussy and fill it with his cum (he learned i was on the pill).

Depending on the response i get, i may share more of what he taught me and how i had my first orgasm with him. ~Jennifer