Living At Charlies Pt 01

To get the most out of this story you should probably read "Traveling with Charlie" first. That's where most of the characters were developed. I'll skim over that here.

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I had lived in a clothing optional community for a few months before I took a road trip and met Charlie. We rode together for about 2000 miles with lots of sex on the trip. Charlie was a hooker on vacation. When we got to my place she loved the atmosphere and before leaving gave me the key to a nice condo she had bought there. She visited about every six weeks.

Living at Charlies place certainly has its benefits. My one bedroom studio was cramped and had a minimal view. This place has a nice full kitchen and overlooks the pool and the park-like area behind it. All my life I had been the keeper. Now I was the kept.

Instead of a queen bed it had a king and the first time I had another woman in it I felt a little guilty before I remembered what Charlie did for a living. She had told me she was hosting a bachelors party that Friday afternoon in a park and the guy wanted all three girls to suck off each of twenty cocks. I figured she was probably on her tenth cock when I was in her bed with this woman. I got over my guilt.

The problem was that this sixty year old women seemed to feel nothing. I tried everything I could to get her to climax. I spent at least two hours licking her slit and clit. I fingered her slow then fast and even got four fingers in. Nothing seemed to have any effect. I licked, sucked, and chewed her clit while I finger fucked her. Still nothing.

Finally I just fucked her. Hard and fast, slow and easy. Nothing. Eventually I came deep in her and thought that might be the key to making her climax. I filled her cunt with hot cum and still nothing. When I softened I rolled off and apologized for not bringing her to climax.

She started crying. "I used to almost cum on demand. Six months ago I had surgery. Now I feel nothing. My doctor says the feeling may come back. Thank you for trying so hard. I could tell it was frustrating for you too. Can I sleep here tonight and just cuddle? I promise I'll start your morning out right."

I told her she didn't need to bribe me but I'd love the wake up call. I spooned behind her and gently massaged her tits. She almost purred as we both fell asleep.

In the morning I woke to her licking my balls. I had to pee and told her so. She followed me into the bathroom and aimed for me. Her aim was good. She shook it once and dropped to her knees. I knew there was some piss left in the bore but she didn't care and sucked me until I came. She was good, but not as good as Charlie.

She lived in the same complex so didn't bother to get dressed. I walked her to the door and she asked if we could try again in a month or so. I assured her that we could.

My next encounter outside of Charlie was a couple of weeks later. She was also in her sixties and slender. The problem with her was she was as dry as a leaf in the winter. I had to use half a bottle of lube to get in her. She climaxed but was still dry. I asked if I could pull out and finish in her mouth and she told me that was disgusting, got up and left. I finished myself.

A few weeks later I got a message from Charlie that she was visiting and had a surprise for me. I went to the airport on a Friday and waited in the cellphone lot for her call. She had someone with her. I pulled up outside of baggage claim and popped the door to the back and then pulled up a seat. The cop was giving me a dirty look so I had to rush. Charlie took the back seat and her friend the front. As we left the curb I apologized for the delay. Charlie reached over the seat, rubbed that special spot she had found on my shoulder, and told me not to worry about it.

As I pulled out of the airport I told the guest that I didn't know Charlie had a sister. She turned sideways and her hand found my knee. "Charlie, you didn't tell me he was a charmer! I'm her mother and I thought she told me everything about you." Her voice was course and husky, probably from years of whiskey and cigarettes. I could smell both on her breath.

I asked just what Charlie had told her about me. She said, "You have a nice cock, know how to use it, and your cum tastes great. She also told me you're great at giving head." Her hand was now on my cock and massaging it.

It was hard to drive but we got to the complex as fast as I could. When we went in the gate there were about a dozen guys without clothes polishing their motorcycles.

"You didn't tell me this! Everybody's naked! Even the guy mowing the lawn over there."

"They're nude, not naked, naked implies sex and outdoor sex is prohibited."

"So right now I can get nude but when we get inside I'll be naked?" Her hand was down my shorts." Her hands were as skilled as Charlies.

They both stripped when they got out of the car. I couldn't because of my hard on. I was barely in the door behind them when I found them both on their knees, side by side and fingers beckoning me to come closer. They stood high on their knees and each undid a button on my shirt until I shrugged it off. Mom undid the button to my shorts and then Charlie unzipped. They fell to the floor and mom licked her way down my leg as I raised one foot so she could pull my shorts off one foot at a time.

Charlie repeated the process on the other leg. They both grabbed the waistband of my boxers and pulled them slowly down to my ankles. Mom repeated the process of licking my right leg as she got me to raise my foot. This time she started at my balls before working her way down my inner thigh and calve. When I picked up my foot she sucked my big toe a bit.

Charlie was obviously following her lead and did the same for my left leg. My cock was throbbing and bobbing. I really wasn't sure how much more of this foreplay I could take. They both sensed it and mom took me in her mouth first. She couldn't get me down like Charlie could but her tongue was amazing. Charlie watched her with admiration as she used just enough teeth to slow me down.

Next it was Charlies turn. She just took me all the way down on the first go and I could feel her tongue lapping at my balls. Mom looked on with pride. I could have cum right then but mom took over and slowed me again. I was begging for relief and they both just began licking me from balls to top until they felt me swell. Mom took the frenelum while Charlie worked the edge of my helmet. I spurted and then just pulsed out more. They took turns licking me clean as they cleaned their faces with their fingers and sucked the cum off.

Mom laid on her back. "She was right about the taste. Now lets see how good you are at eating pussy."

She went to the bedroom, laid back on the bed and spread her legs and fingered herself. She, unlike Charlie, wasn't shaved. I learned later that the men who frequented the strip clubs she worked expected to see some bush. I chewed her nipples for a bit first. They weren't nearly as sensitive as Charlies but I know that can be a complication of surgery. Her clit, when I finally got there was just as sensitive as most women's. She bucked when I put one finger in her ass and my thumb in her cunt and squeezed them together. When I bit her clit she squirted for me. I felt Charlies tongue licking my ass. I spread my legs to give her easier access.

It was tough to concentrate with what she was doing but I had mom where I wanted her. I got three more good squirts out of her before I slid up and let Charlie guide my cock in. Moms pussy was throbbing and so was my cock. She came immediately and continually until I finally unloaded in her.

I cleaned her up as Charlie cleaned me off. Charlie just smiled. "I told her you were good."

They decided they wanted to go for a swim so we all showered and I grabbed some extra towels. As we walked to the pool I explained the towel rule to her. (Always sit on a towel and guys need to cover up hard ons if they get them.) I was pretty sure there would be a lot of covering up that day.

We swam for a bit and Mom expressed her joy at skinny dipping for the first time in years. After about an hour we got out of the pool and walked the garden path that went down by the lake. It's a peaceful place and Mom marveled at the gators cruising the lake. She made a joke about me being unwilling to dip my cock in that water and we all laughed.

As we began to walk back Charlie whispered to me that she wanted me to dip my cock into her cunt and her ass while her mother watched, and asked if I was ready. I wrapped my towel around my waist to show her I was. She smirked at the forming bulge.

We climbed the stairs to the condo. They led the way and I watched two gorgeous asses move seductively in front of my face. I could smell Charlie and saw her juices running down her thigh. Getting fucked while her mother watched certainly seemed to be a turn on.

There is an easy chair in the corner of the bedroom and mom put her towel under her as she sat on it. Charlie took to her knees and sucked me until I was totally hard. She got up and sprawled on the bed with legs spread waiting for me.

The old saying about never keeping a woman waiting is crap. I began with her feet and licked between each toe until she squirmed. Next I dragged my tongue up each leg and thigh until I was just close enough where she could feel my hot breath on her pussy. Her squirms became trembles.

I teased around it for five more minutes. Out of the corner of my eye I could see mom smiling as she diddled herself. I finally gave into my hunger and began a slow and deep licking of her pussy. I still avoided her clit for a few minutes but eventually worked my way up to it and found it throbbing with anticipation as I took it between my lips.

She began a nice long slow orgasm. I kept at it for a while my long finger found her anus. She exploded. I added some warming lube that I had just bought and soon had three fingers in her ass. She knew what was coming next and began to whimper again in anticipation. I'd almost forgotten that we were being observed but Mom came over an put a big blob of the gel on her fingers before retaking her seat.

I rolled Charlie over and put her on all fours. I lubed my cock up with the gel and slowly began to fuck her cunt. She was loving it but I knew she really wanted it in her ass. I made her wait a bit and then pulled out of her pussy and pressed into her ass. She moaned with delight and when I reached around and massaged her clit with more gel she exploded again. Mom was climaxing too.

I knew I couldn't hold back much longer and began to fuck her ass hard. It didn't take long and I filled her ass with hot cum. This time she squirted all over my balls as she came.

She pushed it out for me as I sucked her ass before sharing it with both of them. There was a lot of it.

(Since Charlie had done porn movies in the past I asked her during her last visit if the volume of cum the male stars put out was real. She explained that they all took some pills to increase the amount but she was happy with what I provided. I told her I wanted to cover her face and tits like I saw in the movies. She just clucked but about a week later I received a package from her. In it were three bottles of pills and directions that said to take one pill a day. I didn't recognize any of the ingredients but the next time I went to the doctor I showed her- my doctor- the bottle and asked if there would be any interaction with the meds she had me on. She blushed but said it should do no harm. I started taking the pills a week before Charlies visit. I guess they were working.)

They both licked and sucked my cock clean and dry. Mom looked up at me and said, "That was the nastiest and hottest sex I've ever seen. Do you want to take a fifty year old virgin ass tomorrow?" Charlie and I both looked at her in surprise. "I've never let any guy get there but after seeing how much you both enjoyed it I want to try it!"

I told her I'd be honored. Charlie chimed in that it would hurt the first time but after that it was pure pleasure.

"We're here for three days right?" she asked. I laughed and promised both of them that I'd be gentle.

There was only room enough in the shower for two. Mom went first and Charlie and I would follow. When we heard the shower come on Charlie turned to me. "Remember when I told you about my mom saying I should always be in charge?" I nodded that I did. "When you take that ass tomorrow I want you to bury that joystick in all the way and fly her higher than she's ever been before. Can you do that for me? I want so see her lose control." I promised to do my best and Charlie bent over and licked a drop of seeping cum from my cock. "I know you will," she said as she licked her lips.

We showered next and got dressed to go out for dinner. I suggested a little BBQ food truck I had found. Both looked skeptical but agreed to try it. We sat outside at a picnic table and I watched their faces light up as they took their first bites of the pulled pork sliders. Next stop was a drug store where I bought two more tubes of the gel. After that we hit the bar where I was immediately the envy of every man there. We shot some pool and drank a couple of pitchers before heading home. It was now about 8PM.

We all stripped off our clothes and sat out on the balcony to watch the sun go down. Mom said she had to pee and went inside. Charlie leaned toward me and said, "I want you well rested so you can fuck the hell out her ass in the morning. Don't be too gentle. Make her remember it!" I didn't quite understand the dynamic but agreed.

That night we just slept, three spoons in a row. Charlie was in front of me and my hand just naturally found her nice soft tits. Moms harder tits were pressed into my shoulder blades. I was whipped and slept like a baby in the womb.

I woke hard in the morning and Charlie had rolled all the way over on her back. Mom was on her front with her ass pointing up. She woke when my tongue fount her anus. Talk about the "breakfast of champions". I pulled back after about five minutes, rolled her over and inserted one finger in her ass and my thumb in her cunt. She moaned to show her pleasure. I went to two fingers in her ass and massaged her g spot with the back of my thumb. She began her first of many orgasms. Eventually I got three fingers in her ass and began to stretch it by swirling them around. Climax number two.

Charlie woke with that one and smiled as she watched me dominate her mother. She grabbed the tube of gel from the nightstand and squeezed a good glob around my fingers and lubed my cock with more. She mouthed "Take it hard." I rolled mom over and pulled her up to her knees and jammed all ten inches in her ass at once. She yelped and Charlie smiled.

I began to stroke in and out of her ass and as she turned her head to the side I could see tears welling in her eyes. It's not my style to hurt. I asked mom if she was okay.

"It hurts so fucking good! Please don't stop; just kiss it when you're done." I reached around and pinched her large hardened clit. Climax three came quickly and I unloaded in her when it did. I went down to suck up my load as she pushed it out. I know that turns off some guys but it turns on most women. It did her as well. Just my sucking on her ass elicited another mini climax. I made sure she and Charlie shared the load.. They eagerly did.

Mom rolled over on her back and said she needed to catch her breath. Charlie grinned as she licked my cock clean. I laid there between these two beautiful and sexy women and wondered just what had I done to get so lucky.

Mom got up and went into the bathroom When she heard the shower come on Charlie scooted closer, "When I was just eighteen my mother told me I always had to be in control. Today you took ownership of her ass. I can't wait to hear her beg you to do it again. After our trip I told her what happened and she scolded me for not being in control. This morning you taught her a lesson."

She changed position and laid across the bed with her head on my belly. The shower finally went off and five minutes later mom came out. Charlie was asleep and smiling. Mom laid down next to me and whispered in my ear, "A long time ago I learned how to fake a climax. I even learned how to make myself squirt on demand. There was nothing fake about what you just made me do. I never came so hard in my life. It was fantastic. Just thinking about it in the shower and I had a relapse." The smile on Charlies face turned into a smirk.

We slept for a bit and then I got up to cook breakfast. I put some bacon on a pan and stuck it in the oven. There is truth to the adage of "Don't fry bacon naked." Next I broke about six eggs in a bowl and whipped in a little cream and grated cheese. I started coffee and poured OJ. I thought about making Bloody Mary's but decide to hold off on that for a bit.

When I was ready to cook the eggs and the bacon was done I went and gently wakened my sleeping beauties.

They yawned and stretched and both looked totally sexy. I spanked both their asses a bit to wake them up and told them breakfast would be ready in fifteen minutes. I left the bedroom and set the little table on the balcony before starting the eggs. I like my eggs cooked low and slow with constant stirring. They come out more like a soft custard than traditional scrambled eggs. I had cooked them that way for Charlie a few times and she always liked them.

Ten minutes later I loaded the toaster and did a quick check on the beauties. They were both up and moving and I gave them the five minute warning before I went back to gently stirring the eggs. They came out right on time to fix their coffee. I plated the food and brought it to the table. They started to eat and soon I had two feet rubbing my crotch from underneath the table.

"You didn't tell me he cooked. These are the best eggs I've ever eaten. No wonder you bought this place. He's a gentleman, a charmer, a good cook, and the best fuck and pussy eater I've ever known."

I thanked her for her compliments and began to clear our plates. Charlie stopped me and said they would do it if I'd make us all some Bloody Mary's. I did as she suggested and we spent the rest of the morning on the balcony and watched the pool apron fill up with the younger weekend guests.

At 1:00 I stood and told them that I needed a shower. Charlie asked if she could join me. Of course she could. We lathered each other up and after I rinsed, I fucked her standing up in the shower until we ran out of hot water. She sunk to her knees and sucked me off.

We went back out on the balcony and joined mom who I noticed had fixed herself another Bloody Mary, maybe her third. Charlie suggested a walk around the lake and I agreed. Halfway around the lake there is a park bench and we sat and watched the gators cruise by.

Mom spoke, "Can you do that again for me tonight I need it! Please!" Charlie smirked and squeezed my thigh. I decided to tease.

"Since you were a virgin there I didn't want to hurt you too much."

"Hurt me? You made me bleed and I loved it! I want it again! Do it please!" I glanced at Charlie and she nodded her approval. I guess that was close enough to begging for her.

We went and hit the BBQ place again by popular demand. We played some pool and drank some beer before heading home. The anticipation was building and I was thinking about what sort of wrinkle I could add. Apparently Charlie wanted to see her be a bit submissive.

They stripped as we went in the gate. Both seemed to love the clothing free lifestyle. I followed them up the stairs and when we went into the condo Charlie undressed me. I took mom to the bedroom and directed her to the bed. Charlie took the seat on the chair in the corner. I used a little lube but started with two fingers in her ass this time. She shuddered but didn't complain. The third finger made her grunt. The fourth made her moan and I could see the sweat start to glisten on her lower back.