The next day I was sitting on the lifeguard stand when Amy came up to me, looking around to make sure no one was listening.

“Hi Amy. Tomorrow’s your big date with Connor. Are you ready?”

“Um, that’s what I wanted to talk to you about. My older sister is friends with a girl Connor used to date. She says he likes anal sex. What should I do?”

“You don’t have to do anything you don’t want to, Amy, particularly on the first date.”

“I know, but, um, I need to be ready and yesterday when you put your finger up my butt it felt really good. I was wondering if, you know, you could teach me how to do anal before my date with Conner.”

I had to be dreaming. Amy had an ass most girls would die for.

“Of course I will, Amy. Come by my house at four.”

I explained to her how to clean herself and make sure she was well lubricated. She showed up promptly at four wearing a pair of cutoffs and a tee shirt. I invited her inside.

“Amy, let’s go up to my room and get started. I’m not going to just pull out my cock and shove it up your ass, and Connor won’t either. We need to get warmed up first like we did yesterday.”

She nodded. We sat on the bed and kissed. My hand pushed up her top and squeezed her tits. Then I sucked her nipples into my mouth, raking my teeth across the hard tips. Amy moaned. I unsnapped her cutoffs and shoved a hand down her panties. Her pussy was bare. She had shaved like I told her to. I slipped a finger through her folds and buried it up her cunt. She squirmed against me. I moved my finger to her clit.

“Oh, oh, oh… it’s… It’s happening.”

She threw her head back. Her body twisted and jerked as the orgasm gained momentum. I shoved two fingers up her cunt and fucked them in and out. Amy screamed. Juices drenched my hand. I slid to the floor and pulled her cutoffs and soaked panties from her feet. She was still struggling to catch her breath. 

I parted her thighs and moved my head between them, clamping my mouth around her pussy. I shoved my tongue up her cunt and lapped up the juices still flowing from her body. Amy put her hands on my head and squirmed against my face, moaning and gasping. I moved my tongue to her clit and shoved two fingers into her pussy. She went off again. A flood of juices filled my mouth. I swallowed them all.

I rolled Amy onto her stomach and climbed on her back. My cock slipped between her cheeks and plunged into her pussy. I shoved a finger up her ass and twisted it around inside her. She was well lubricated as I had instructed. I added a second finger. Amy shrieked and had another orgasm.

“I’m going to put my cock in your ass now, Amy. Try to relax. I’ll go slow.”

I pressed my knob against her sphincter and pushed. I slowly pried her open until I popped inside. Amy stiffened. I waited for her to relax and pushed deeper. Her asshole clenched me tightly as she stiffened again. I waited for her to relax and pushed another inch of cock up her ass. Soon all eight inches were buried deep in her bowels.

“I’m going to wait for you to tell me you’re ready. Then I’ll move my cock in and out a little at a time until you get used to it. Okay?”

“I… I’m ready.”

And she was. In no time, I was fucking her ass with long, deep strokes. Amy moved with me. God, she was tight. I wasn’t going to last long. My hand went under her thigh. My finger found her clit and rubbed. Her moans got louder and more desperate. My balls tightened. My cock swelled. I thrust deep and pumped her asshole full of cum. Amy’s pussy exploded. I collapsed onto her back, breathing hard. My cock was still deep in her ass.

“Amy, just like normal fucking, there are several positions for ass fucking, most of them the same. Would you like to try some?”

She did. I had her get on top and ride me cowgirl style, then reverse cowgirl. Then we did it missionary with her legs bent back to her shoulders. After that, I fucked her ass standing up against the wall. When I was ready to shoot, Amy got on her knees in front of me. I painted her face with a big load of cum.

“Can we practice one more time before my date with Connor, maybe tomorrow?”

“Of course, Amy. Come by tomorrow at ten in the morning, before my shift at the pool. I can teach you some other things Connor may like.”

After Amy left, Emily sent me a text and asked if I could meet her that evening. There was something she urgently needed to discuss with me, but it had to be in person. I picked her up in front of her house at nine. She told me to drive to a place where no one could see us. My curiosity was aroused, but I followed her instructions. We ended up on a dirt road near the golf course. I turned off the engine.

“So what’s up?” I asked.

“I heard Amy came over to your house this afternoon. Why wasn’t I invited?”

“She wanted more advice about her date with Connor. I figured she would have asked you to come if she wanted you there.”

“You fucked her, didn’t you?”

“That’s between Amy and me. Is that why you needed to see me so urgently?”

Emily pushed down her spandex shorts and panties, pulling them from her feet.

“I want you to fuck me.”

“Okay. Let me finger you first and get you ready.”

“No. I want you to do me with your mouth. Then we’ll fuck.”

Even better, I thought. Emily swung around in the seat with her head out the window and her ass in my face. In the light of the full moon, I could see the outline of her cheeks and the swollen pussy hanging between her thighs. I turned in my seat and buried my face in her ass, shoving a tongue up her cunt.

“Mmmmmmm… yes…”

I sucked and slurped her juicy peach until it was dripping. I moved my tongue to her asshole and shoved two fingers up her cunt. Emily squirmed against my face. Her moans became louder and more desperate. I rubbed her clit with my thumb. She went off like a geyser. I clamped my lips around her and drank her slimy love potion.

“Okay, I’m ready to fuck now.”

“Maybe we should get out of the car,” I suggested. “There’ll be more room.”

“No. I need to be home before my parents discover I’m gone. We can do it in the car.”

It was going to be awkward. I suggested she let me sit in the passenger seat. It took some maneuvering, but I was able to slip underneath her. Emily was facing the dashboard. I pulled out my cock and lowered her ass to my lap. My knob slid between her cheeks and lodged in her opening. She impaled herself down my length.

Emily bounced up and down on my cock like the enthusiastic schoolgirl she was. I slammed up into her each time she came crashing down on me, bouncing off her cervix on each thrust. My hand went under her top and pinched her tiny nipples. Emily loved it.

“Fuck me, fuck me, yes, yes… uuunnnggg…”

Her pussy clenched my cock. Juices streamed down my shaft and over my balls. I continued to pound my cock into her. She went off again and again, one orgasm after the next, gripping her pussy until it was impossible to distinguish them. Her screams were loud and out of control. 

It was too much for me. I couldn’t hold back. At the very last second, I realized I couldn’t take a chance she might get pregnant. I pushed her off my cock just as the first jet of cum exploded from the tip. It shot up the crack of her ass. Emily came crashing back down on me, desperate to get my cock back in her pussy. Instead, her sphincter landed squarely on my knob. It punched into her asshole just as a second blast of cum spewed from my cock.

Emily shrieked and tried to lift off me, but my cock was too tightly embedded inside her. Another spurt of cum sprayed up her asshole, acting as a lubricant. She came down on me again. My cock sank deeper. More cum filled her bowels. The next time she came down on me, all eight inches were buried deep. 

Emily sat there trembling with my hard cock up her butt and cum oozing out and dripping down my balls. She slid a hand between her legs and rubbed her clit. Her body stiffened and jerked as this new sensation set her off. When she was finished, we both just sat there catching our breath as I slowly deflated inside her asshole. She finally lifted off me. A flood of cum poured into my lap.  

“I can’t believe you just fucked me in the butt. It hurt at first, but then it felt really good. At least you didn’t do that with Amy, so that’s something.” 

I didn’t bother to correct her. Emily pulled on her panties and shorts. I slid back into the driver’s seat and took her home. She kissed me on the cheek and hopped out of the car to sneak back in the house.

The next morning, Amy showed up at ten. She wore a pullover that fell to her upper thighs. It was obvious she wasn’t wearing a bra. She lifted the hem to show me she wasn’t wearing panties either. I stared at her bare pussy puffing out from between her thighs. A gash separated the two halves. I took her hand and led her up to my room.

“You said something about teaching me other things that I could do with Connor.”

“I did. I’m going to teach you how to deep throat my cock. Not all girls can do it, but I think you can. Do you want to try?”

“Okay. What do I have to do?”

“Take off your pullover, and I’ll show you.”

She did. It took several attempts to get past her gag point, but Amy was determined. Eventually, my cock pushed into her throat until my pubes were pressed against her lips. We did it several more times before Amy could do it with ease. I taught her how to push out her tongue and lick my balls while my cock was in her throat. 

“Some guys like to do what’s called face fucking. It’s kind of sloppy with spit flying everywhere. Do you want to try?”

She did. Soon, my cock was punching into her throat on each powerful thrust. Spit poured from her lips and dribbled down her chin. I pulled out and slapped my cock across her face, then shoved it back down her throat. To say Amy loved it would be an understatement. She had a hand between her legs rubbing her pussy. Her desperate eyes looked up at me, begging for more. Tears ran down her cheeks.

“Oh fuck, I’m going to cum.”

I pulled my cock from her mouth, wrapped my fingers around my shaft and sprayed a steady stream of cum onto her face and into her hair. Another blast sprayed into her mouth and across her cheek. I aimed lower and doused her tits with cum. Amy was frantically rubbing her pussy. She tensed and began shaking. The orgasm left her breathless.

“Wow. That was so intense. Now are you going to fuck me in the ass?”

“No, Amy. First, I’m going to teach you how to do sixty-nine. It’s when I eat your pussy while you suck my cock at the same time. Go clean yourself up and I’ll show you when you get back.”

I got on the bed and had Amy climb on top. She swung her leg over my head and lowered her mouth to my cock. I clamped my mouth around her pussy. Her lips flew up and down my shaft. Using her new skills, she took me into her throat. I shoved a finger up her ass and flicked my tongue across her clit. Her pussy exploded into my face, drenching me with girl cum. We rolled over with me on top. I fucked her face while licking her clit and fingering her pussy. She went off again.

“Now we can fuck. I’ll do your pussy first and then your ass.”

The girl was insatiable. We fucked in every position I could imagine. I slapped her tits and choked her. She loved it. Her orgasms were nonstop. I had to pull out several times to keep from blowing my load so I could fuck her ass. She loved that just as much. We were both sweaty and exhausted when I thrust deep and filled her bowels with cum. 

I had to get ready for work and walked Amy to the door.

“Good luck on your date with Connor tonight.”

She thanked me, kissed me on the cheek and left. I watched her ass sway back and forth against her pullover and told myself what a lucky guy I was.