Chapter 3

Saturday morning, Lindsey and went out for breakfast, and then took a drive out to the pier in Santa Monica. I took the long way and drove over the hill to Hollywood, then along Santa Monica Blvd through Beverly hills. She really enjoyed the sightseeing.

After a few hours exploring the games and food stands we took a drive up to Malibu and then up over Topanga Canyon. As we wound our way up the hill, she asked about sucking dick. How, what to do, etc. So I pulled out onto a dirt portion of Mulholland drive and into a small culdesac that wasn’t visible from the road.

I got out and got into the back seat of my car, and motioned for her to join me. I opened my pants and pulled them down around my knees, leaving my cock exposed.

“Start by stroking me a little, til I start getting hard.” I instructed her. “Once it’s there, make an ‘O’ shape with your mouth and lower your self over me and take the tip in your mouth.” When her soft lips touched the sensitive tip of my dick a moaned.

“Yeah. Just like that.” I said in a sleepy voice. “Now pump your hand p and down and try moving your head down as far onto me as you can without gagging.” As expected, it wasn’t very far. So I told her to back up and just go that far, and stroke my shaft while she sucked and licked with her tongue.

Lindsey was a quick study. And with a warm, wet mouth and tender tongue flicking over my cock’s head, I was a quick shot as well.

“I’m gonna cum, Lindsey!” I croaked. Then panting I aid. “Try to swallow as much as you can. Don’t worry if you can’t. It’s your first time.” I was panting now and about to lose control. Then the dam broke. I grabbed the sides of Lindsey’s head and bucked upward.

My cock gave a final throb and released a hot stream of sticky semen into her young mouth. Her cheeks puffed up and I heard heard gag. But to my surprise, She held back the gag and I felt her swallow. Looking at her, it looked like it was a painful swallow, but she’d done it anyway.

When she came up from my crotch and looked at me, she licked her lips and said. “It didn’t taste bad at all.” I smiled and gazed happily at her smacking her lips as if tasting the thick ejaculate again. “Not nearly as bitter as beer is.”

“Oh?” I asked. “Do people shale up beers and aim them at your mouth very often?” I meant it as a joke but then, she asked.

“Will you promise not to tell Mom?” then, looking around as if Kat was suddenly going to pop up from nowhere. “Me and Laura shotgun beers every now and then in her garage.” So the joke wasn’t a joke after all.

“Well little lady.” I said petting her soft hair and running my hand over her cheek. “You certainly did a wonderful job.” Then placed my thumb against her lip and she automatically opened her mouth. I pushed my thumb in as far as I could to see if I could gauge her gag reflex.

She didn’t gag, but sucked on my thumb instead. “Do you REALLY gag on pills?” I asked. Wondering, now if there was more to it.

I never did get an answer. Lindsey looked at me suspiciously at every meal, but if she were searching for something that tasted off she never found it. On the upside she got a lot better at sucking cock over the weekend.

If she wanted to tell herself, and others, that gagging on pills and not on cock was different, then so be it. I wasn’t going to push. But I’d bet Kat would, when she found out. One day, the truth would come out.

I found that babysitting, for Lindsey anyway, wasn’t a half bad gig. Living room, Bathroom, Bedroom, My Apartment’s Pool and Spa, Even the steam room. Lindsey wanted to have sex in all of them. After really hot sex in the steam room, I brought up a new subject with Lindsey.

“You’ve learned a lot since our first time together.” I began. Lindsey gazed back at me through the haze and smiled. “You really turned out to be a top notch cock sucker.” She even took pride in that title.

“Do you know what anal sex is?” I asked. Her eyes nearly popped out of her head, and her hands immediately went to her ass cheeks.

“BUT SEX!?” she exclaimed. “You ... You wanna fuck in in my behind?” She really sounded shocked.

I shrugged. “It’s a suggestion. Just another form of sex.” I assured her. Then scooted close to her.

“Come, lay down over my knee.” I patted my thigh and she obliged. I gently rubbed her buttock with my palm for a moment then took my middle finger and drove it past the her thick, muscled cheeks. I paused when I felt it press against the sensitive button that was her anal sphincter.

Lindsey gasped when the contact was made. I told her to just relax and explained that all I was going to do was press my finger inside. That it wouldn’t be any worse than if her mom was using a thermometer on her. That made her giggle.

The humidity in the steam room had made us both slick and sweaty. So while she was laughing, I pressed my finger inside. As soon as it was in, she gasped and took a deep breath.

“It feels weird.” she whimpered. Then she wiggled her bottom. That little action forced my finger deeper, and she squeaked. “Eeww!” and she froze in place.

“Just relax sweetie.” I instructed. “I promise, it will feel good after a few minutes.”

“But.” she began fishing for excuses.

“Did I tell you it would hurt the first time I fucked you?” she nodded. “Did I tell you it wold feel better after a few minutes of getting used to my cock?” again, she nodded. “Did it start to feel good?”

She answered with an enthusiastic “YES!” then began “This is different though.” and I shook my head.

“Nope same thing, different hole. Just relax.” She took a breath and sighed. “I promise I won’t hurt you. Then I began moving my finger in and out. Going deeper with each stroke. After a bit, Lindsey actually began to purr. She was hooked. No I just had to train her for bigger things.

The weekend ended all too soon for my taste. Lindsey was turning into a sex machine. She took it all in stride. I had gotten her to take two of my fingers in her ass by the time it was tie to head up to the hills to take her home.

During our lunches the following week, I filled Kat in on my escapades with Lindsey. She complained that I never fucked her in the ass in all our time. I told her I’d just never thought about it since all of our sex seemed very spontaneous.

“Well, just make sure your cock is in my rear end long before it ever sinks into hers.” The look on her face was serious, but not threatening. Then she smiled and kissed me.

“This weekend?” I asked. Kat gave me a quizzical stare. “My cock, you ass, Friday night.” I said. She smiled and licked her lips. I took that to mean I was in the clear.

I had no idea how much Kat craved anal, until Friday night. Lindsey was downstairs music loud. I had to laugh because she probably did that to keep from hearing her Mom and me.

Kat an I both cleaned up in the shower. Then she sat on the edge of the bed and gave me a slow sensual blowjob. True to form her finger wound my ass again. I really didn’t mind by now. It felt good.

She was a little surprised when I had her lay on her back. But I told her, I could get deeper penetration this way. I lifted her legs and threw them up over her shoulders. Bending her nearly in half. Her sweet pussy and puckered ass were exposed to the world now. I could see she’d been fucked in the ass before.

“Do me hard and fast, lover.” She demanded. So I lubed my palm and stroked my cock a few times before pressing my cock to her puckered hole. I pushed in and didn’t stop. I pumped my cock balls deep into her and she screamed in delight.

“Oh FUCK Yeah!” she yelled. “Fuck my Ass baby! Destroy my Hole! Make it yoursssss!”

I pushed myself up on her thick buttocks and began thrusting in and out. Feeling her ass clench around me and hearing her cries and yells with each thrust.

“Oh baby it’s been so long!” she panted. “You have no idea how much I love this!” After a few minutes I pulled back and grabbed her around her hips, legs on my shoulder and kept pumping my cock into her tight ass.

The more Kat squealed and yelped, the harder and deeper I tried to force my cock. Her constant insistence that I was giving her something she missed for several years, spurred me on. My cock was beginning to ache and my hips were cramping.

“I AM Going to cum!” I shouted through gritted teeth. “I’m gonna flood your ass with my hot cum!”

Her response, instead of wanting me to hold off, was. “DO IT! Flood my filthy Ass with your cum!”

So I did. I came, it hurt. It was hot, and felt like lava spraying out. Then I froze. Cock still deep in Kat’s ass.

“What have we here?”” I heard a somewhat masculine voice with feminine overtones. And a bulge press against my ass crack. Then Kat screamed.

“God Damnit Rene!” She sounded truly pissed. “What the fuck are you doing here?”

The bulge was, thankfully, covered in denim. I knew what it was. The voice from above it called out. “I rang the bell honey, but no one answered.” There was a bit of panic in the voice.

“Eventually Lindsey came to the door.” I thought I heard a sigh of relief. “Sweet thing. Told me you had company and that you were probably getting fucked to death.”

I couldn’t suppress a guffaw. Then the voice addressed me. “I’ll have to chat with you later, handsome.” he said. Then a warm hand patted my ass cheek. I felt my cock throb and spring back to life.

“What the fuck?” Kat asked. I tried to shush her. Rene caught the exchange. And misunderstood, so he elaborated.

“Oh honey, I hate to be the bearer of bad business.” Rene drawled. “But I think handsome here is sowing oats in multiple fields.” his hand landed again, just a bit harder. My cock throbbed. What the actual fuck? Why was this happening.

“When Lindsey told me about you getting plowed, she sounded awfully jealous.” He leaned over me toward Kat. And went on. “Katheryn, my flower, I think she’s in love with two time Timmy here.”

I swear his bulge was growing every time he patted my ass. My my reaction was simply because my cock was still inside Kat and it moved each time I got a smack. I shivered involuntarily. Rene took that as confirmation of wrong doing.

“See that Lovey!” his voice went up and the pitch went down. But before he finished, Kat chimed in.

“I know!” she screamed. “I asked him to train her in sex before she hooked up with a loser!”

There was a gasp from Rene, and Kat demanded. “Why are you interrupting the first GOOD Ass fucking I’ve had in years!?”

Rene gasped and stepped back, the pressure against my crack vanishing. I pulled out of Kat and stood up. Rene gasped again after viewing my still rock hard cock.

“Oh my...” Rene let the last syllable drag out. “What’ll it take to gt you to grace ME with that fillet?”

Kat. Obviously still a bit upset that we were interrupted said. “Maybe he’ll agree if you gave him a taste of yours first. I just blanched, and Rene began stripping.

“Yum!” Rene cheered excitedly. And Kat shoved me, sending me back on to the bed on my back. In a flash to quick to see, my legs were up and I felt Rene’s cock against my sphincter.