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Teen Diaries 3: Losing My Oral Virginity

Tags: teen oral
Anna gets an oral lesson from her dad's friend
My name is Anna and I'm a 16 year old virgin. I'm the only one of my friends who hasn't gone past kissing with a guy and it's not that I'm ugly. I get hit on a lot, so I guess guys think I'm hot. I just think I should save myself for the right guy.

I have light red hair, lightly freckled skin, I'm pretty thin but with a decent butt and small boobs. My friends make fun of me for being a virgin all the time and I've thought about fooling around with a guy, but I don't trust most of the guys at my school. They all like to brag about who they've been with and I don't want to be talked about like that.

Last night my parents were out of the house, but at 9:30 my dad's friend Chris knocked on the door.

"Chris, what are you doing here?"

"Hey, Anna, my water heater broke. I texted your dad and he said I could come use your shower. Is that okay?"

I hadn't checked my phone for a while, but I let him in and then checked. Sure enough, dad texted me and said Chris would be stopping by. Chris was in his late 40's, about 5'10. His hair was already grey but he had a youthfulness in his face still. I had seen him in shirts without sleeves before and he had nice arms.

Getting curious about what the rest of him looked like, I decided to peek through the bathroom door. I could see his silhouette through the curtain, but couldn't really make out his penis. I quietly crept closer when he shut the water off. In a panic, I went to the sink and started washing my hands.

"Oh! Sorry, I got my hands dirty and needed to wash them..." My face was red with embarrassment.

"Why didn't you use the kitchen sink?"

Shit, that would make more sense. I was kind of screwed. I struggled to think of an answer when he said, "Have you ever seen a naked man?"

I paused for a minute wondering what I should say. I finally replied, "No."

Chris started to smile as he walked towards me. "Have you ever kissed a guy?"

"Well yes, obviously."

"Have you ever kissed a man?"

I froze, looking into his eyes. I didn't know what to say, but he put his hands on my shoulders and leaned in to me and kissed my lips softly. Then he did it again. Then he turned his head to the side and pried my lips open with his and I started kissing him back. He smoked and his mouth tasted like how smoke smells. It was kinda gross but it felt really good. It had been a while since I'd been kissed.

"Has anybody ever sucked your nipples?"

I looked down at my little boobs in my shirt. I shook my head no and he gently lifted my shirt over my head and took it off. He unhooked my bra and dropped it to the floor as he leaned in to suck my nipples. I started to moan softly. It felt so good. He rubbed whichever nipple he wasn't currently sucking as he alternated between them.

"Would you like to see my dick? You've made it really hard."

"I kinda want to see it, but can I see it soft?"

"Well that's not really how it works. It will go soft when I'm no longer turned on."

"When will that be?"

"Maybe after I cum." He dropped the towel and his dick was pointing straight out right at me. His head was really big and I wondered if all penises looked like his. He had a lot of pubic hair above it which was grey and black. He also had really hairy balls. His whole body was pretty hairy, but the area around his dick was so hairy I couldn't see skin through it.

"Have you ever touched a dick?"

I shook my head no. He reached down and grabbed my hand and put it on his dick. His skin was so soft, but his penis was so hard! I expected hard penises to still be kind of soft. His big head was, but not the shaft.

"Would you like to suck it?"

I figured there was no time like the present, so I leaned forward and put his head in my mouth. It didn't have a taste really, but I did taste some really really salty liquid that was on the tip before I put my mouth on it.

"You should suck is harder and take it in and out of your mouth."

I followed his suggestion and he dictated what was good and what was bad. Like when I accidentally touched it with my teeth, he said "No teeth" or when it touched the back of my throat he said "That feels great." Then he took my hand again and put it on the side of his dick. "Stroke what can't fit in your mouth. It will get me off faster." His crotch had a funky smell as I sucked and stroked his dick.

"I'm going to cum soon. Do you want to taste it?"

I shook my head no as I kept sucking. About a minute later, he pulled his dick out of my mouth and cupped a hand and came in it. He held his hand in front of my face to let me see it. It was so milky and white. "Are you sure you don't want to know what it tastes like?"

"I don't know. I've heard it tastes bad."

"Well you never know until you try it."

I leaned into his hand full of cum and stuck my tongue out and got some on the tip. It was salty and bitter. "I don't want to taste any more."

"Alright. That's fair." He walked to the sink and washed his hand off. Then came back to me. I had stood up from the floor and he kissed me some more and then started rubbing his hand between my legs. I still had my shorts on. He dropped them to the floor and rubbed my pussy through my panties. "Has anybody ever touched you here?"

"No." It felt so good. He picked me up by the butt and sat me on the bathroom counter as he slid my panties off. He got on his knees and put his head between my legs and started gently kissing my clit. It felt so good I started breathing heavy. His tongue went down and up my lips from my hole to my clit and it felt great. He pulled his head back to look at it and I felt his fingers spread my lips.

"Oh wow!"


"Your hymen is still there. You're a total virgin."

"Yeah I am. Is that okay?"

"Yes. It's so hot! You've never been fingered before?"

"No. Won't it hurt?"

"It might." With that, he started to slide his index finger in the tight hole under my hymen. My toes instantly curled and my neck tilted my head to by shoulder as I closed my eyes in pain. It really hurt! He started sliding it in and out slowly while I sat there squeezing the edge of the counter.

"Don't worry, it will feel better soon."

He was right. After another minute, it started to feel great. Then he returned his tongue to my clit as he fingered me more. I started to writhe as this sensation filled my body with heat and I felt intense pleasure in my vagina. I started moaning and shaking uncontrollably and he pushed his finger in to the base and held it there.

"What just happened to me?"

"Anna, you just had your first orgasm. How did it feel?"

"It felt great! Thank you."

"Has anybody ever licked your ass?"

"What? No! That sounds gross."

He picked me up off the counter and turned me around to face the mirror. I could see him behind me as he bent me over the counter and his hands spread my ass cheeks. He started licking my asshole and it actually felt great! Not as good as when he licked my pussy but I liked it a lot. Then he stuck his finger in my ass. It didn't really hurt, not like his finger in my pussy, but it felt a little uncomfortable.

He reached between my legs with his other hand and rubbed my clit again as he fingered my ass. Then he stuck a finger in my pussy as well and started fingering both. It felt so good and within a few more minutes, I was having another orgasm and I felt my pussy build up with liquid as it slowly leaked out below my hymen.

After he pulled out his fingers, I stood up and turned around to look at his dick again. It was still hard. "When does it get soft?"

"Well I'm still horny." He started jacking off his dick while he kissed me. He spit on it and after few minutes he came, spraying his load on my tummy and down my leg. It felt so warm on my skin. I got on my knees and watched his dick as it slowly softened and shrunk. It looked way better hard than soft.

I wiped his cum off me with a towel as he got dressed and I walked him to the door. He turned to me and said, "If you ever want to lose your virginity and go all the way, you know how to reach me."

I thanked him, but told him I was saving that for when I'm in love with a guy. But I did have fun and didn't regret letting Chris be the first to touch me like that. I felt better prepared for my next future boyfriend.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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