Living at Charlies Pt. 02

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True happiness found at the apartment of a young hooker.
6.3k words
4.68
11.4k
7

Part 2 of the 2 part series

Updated 06/08/2023
Created 09/17/2017
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oldbob68
oldbob68
176 Followers

I knew I should just be content with Charlies visits but for some reason I wasn't. The view from the condo's deck during the week wasn't anything to write home about. There were lots of older saggy baggies. On the weekends, however, there were lots of young visitors there to work on their all over tans.

Most of the women were young and fit. The guys were buff and I saw no value in going down there and trying to compete with them. I am sixty-nine years old. But I did enjoy sitting on the balcony and just appreciating the beauty of the young women.

There was one particular young woman I was always pleased to see. She is fairly tall, has long raven black hair, a fantastic deep bronze tan body with no visible tan lines, and nice "c-cup" tits with dark areola. She was always accompanied by a twenty something guy who obviously spent a lot of time in the gym. They were there most weekends but on this day the guy showed up with a pretty stunning blond instead.

I sat on the balcony and wondered just what this guy had going for him. I don't spend much time checking out the competition but this guy had a dick like a well used pencil.

Below me I heard a voice. "What's the view like from up there?" I looked down and it was the raven haired beauty. I told her it just got a lot better. She was wearing a lace cover-up that hid nothing and was sexy as hell.

"Come up and see for yourself; doors unlocked." A few seconds later I heard the door open and close. I called out that there was beer in the fridge. I heard the fridge door open and she walked onto the balcony carrying two bottles of beer. Somewhere along the way her cover-up had become unbuttoned.

She sat next to me on the settee. Her long black hair fell to the front and almost covered her tits.. Her nipples protruded through.

"Wow, you can see everything from up here. Are you a voyeur?" I assured her that I appreciated the female form so I guess I could be classified as one. "I've felt you watching me a few times." I told her I had always enjoyed seeing her and that she was a beautiful woman.

"Can I ask you a question?" I told her she could but I had some of my own.

"Who is the younger woman I see you with up here sometimes?" I told her she was a friend and actually owned the condo,

"My turn. How come you're not down there with your boyfriend?"

"He's an ex boyfriend. Now he's down there hitting on my best friend."

"My turn. Where is your friend and why are you here alone most weekends? Last weekend her sister was here with her. "

"She lives in California and she bought this place so we could be comfortable when she visited. We have an unusual relationship. I won't tell you anymore about her. I respect her privacy. That wasn't her sister though, it was her mother."

She shrieked in laughter. "You did a two generation fuck?"

I didn't answer.

"My turn. Why did you shave? You had a beautiful all natural bush. The only tan lines I can see now are where it was a few weeks ago."

"Needle dick, down there, couldn't please me in the normal way and I thought if I shaved he'd at least try the other way. No such luck, and now he's talking to Cheryl and look at the bush on her! And hers is course while mine was fine and silky. I'll let it grow back but I have no idea how soft it will be."

I wondered how she knew what Cheryl's bush was like but didn't ask. I learned that her name was Princess.

"Can we cut to the chase? No offense and you don't look overly endowed but if that woman is willing to buy this place and fly here every so often you must be something special. I need something special."

Her hand found its way across the settee and up to my cock. I started to swell and she leaned over and took my little worm in her mouth. Finally I was at my full length and she pulled off and looked at me with wonder in her eyes. "I've only been with four guys. The first was an eighteen year old that had no idea what he was doing the second was older and could satisfy me always. Number three could satisfy me sometimes. And then there was "needle dick" who is all about himself. I know we're going to have sex but would you do me a favor and when we stand up to go inside let him see that magnificent cock?"

I did what she asked. When I stood up I pretended to yawn so my dick hung over the railing. We got in the slider and she dropped to her knees. "I hope he's watching." She gave me a pretty good blow job for someone with limited experience. I looked out; both her boyfriend and friend were watching. When I came she stood and went back on the balcony and stuck out her milky white tongue at them before swallowing.

"OK. I'm done with revenge. Let's just have fun."

Her body was so perfect I didn't know where to start. She laid on the bed and I rolled her over on her stomach. I began with that nice tight bronze ass. I took gentle nibbles on each cheek and slowly worked my way in closer with each nibble getting a little harder. She reached around and pulled her cheeks apart for me. As my tongue found her brown rosebud she almost shrieked her approval.

I slid my hand down between her and the bed and let my fingers do the hunting until I found her hard little clit. The combination of my tongue in her ass and my finger on her clit made her cum almost immediately. I pulled back and rolled her over. My thumb found her cunt at the same time my very long middle finger found her asshole. I pushed them in at the same time and felt her shiver a little. I began to lick and nibble her clit. Within five minutes she graced me with a shower of her womanly juices.

I licked it up and gave her our first kiss before rolling on my back. I was hard and just let her take control. She gave me a few good licks and then straddled me before impaling herself on my cock. "Fuck; that feels good. I've never been that full before."

She had control and I just let it go. The only thing I did extra was to brush her anus with my fingers. She came instantly when I did. Her pussy gushed for the second time. I filled her with cum. When I went down and licked her clean she was shocked. "Now that was special."

I moved up and we kissed. Her tongue did it's best to clean my mouth. We napped and she woke me in an hour or so by working my anus with her tongue. I reached down and pushed my cock so it was pointing down. She got the hint and moved down to take just the head of my cock in her mouth. She just let her tongue do the work and I came hard in her mouth.

We spent the better part of the night, sucking, licking and fucking. In the morning I cooked breakfast and she told me she had to go to work. She was a dealer at a local casino. I learned she was half Seminole and half Mexican. Her parents were nudists and had belonged to a place up the road for years. She sort of grew up there and in the naturist lifestyle. She had never owned a bathing suit in her life.

Before she left we had one last long and slow fuck.

The next Saturday I heard a knock at my door and when I answered it there were Princess and Cheryl. "Is this where the fun is? This is Cheryl, my best friend. She learned her lesson about Needle Dick and is looking for something entertaining too. She reached down and began to rub Cheryl's pussy. We can also be very entertaining if you're into that sort of thing. Cheryl was very pretty with smallish tits but a fine lithe body.

I admitted that I had never seen it live but would love to. They came in and I offered them a drink. Cheryl piped up, "We been discussing this for two days. We want pussy juice first, followed by cum, and then maybe a beer." I led the way to the bedroom and took the easy chair in the corner. They climbed on the bed and began to kiss. It was long and lingering and I could catch glimpses of their active tongues as they probed each others mouth.

Princess broke the kiss and began to work her way downward. Her hands found Cheryl's pussy as she chewed her pink nipples. I could smell the sex emanating from both of them. Princess moved down further and worked her tongue all the way around Cheryl's Mons a few time before just plunging it into Cheryl's wanting cunt. As Princess took her prize Cheryl moved her foot up and began to massage Princess's pussy. They both came and I made a mental note to be sure and lick Cheryl's foot clean.

They rolled over and switched positions. This time Princess was on the bottom and Cheryl must have been hiding a large cunt behind her lush bush because I watched her impale herself on Princess' foot as Cheryl began to eat her friends pussy. I'd never seen anything like that but they both seemed to be enjoying it tremendously. Princess' toes were obviously hitting all the right spots and Cheryl's tongue and fingers were as well. It was hot.

They both came hard and long and beckoned me to come to the bed. The told me to lay down in the middle and they assumed their positions at right angles to me. They alternated turns sucking my cock. I couldn't hold on for long and Cheryl took the first shot. Princess dove in and took the balance as she inserted a finger in my ass and massaged my prostate.

When I was depleted they shared my load and then Princess took her finger from my ass and offered it to Cheryl. She licked and sucked it clean. I got up to pee. When I got back they were laying shoulder to shoulder with pillows under their asses and knees bent and raised.. Both were fingering themselves. Not a word needed to be, or was said.

I knelt between them and replaced their fingers with mine. I learned a long time ago that every pussy is different. Princess' magic spot was very close to her opening and responded best to fast finger action. Cheryl's pussy was going to take some exploring. I couldn't find her spot but remembered a girl from long ago that just loved it when my long middle finger did lazy circles around her cervix. That did the trick and soon I had them both cumming hard on my fingers. Even Cheryl's huge pussy was squeezing my hand.

Princess pushed my hand away and whispered in my ear that she wanted me to fuck Cheryl and fill that big pussy with cum so she could drink from it. "She has to go to work tonight. I don't. We'll have all night to please each other."

By this time I had my entire hand inside Cheryl. I'd never fisted before and it was interesting to explore her internal anatomy. It also kept her orgasms coming. I began to lick her clit and they increased in intensity. I pulled my hand out and slid my cock in. She pushed her legs together and that tightened her up a bit and increased the friction. I pulled out and rolled her to her knees. I went back in and she pressed her legs together again. In this position I could stroke faster and the speed seemed to make up for the lack of friction for me. I blew my load all over her cervix.

I pulled out and presented my cock to her lips for cleaning while Princess moved down and inserted her hand in Cheryl's cunt and came out with it covered in cum. I watched her lick and suck each finger clean before she planted her mouth on Cheryl's cunt and began to suck. She showed me her harvest before swallowing.

I needed a nap and told them so. They said they were getting in the shower. I fell peacefully asleep. I woke and looked at the clock. What I had expected to be a half hour power nap had grown to almost two hours. I rolled over on my back and saw Princess sitting in the corner and listening to my I-Pod. She noticed my movement and smiled as she took the earbuds out. She stood, walked to the bed, and sat next to me.

"I gave Cheryl a ride home and stopped at a deli to buy some cold cuts, cold salads, and rolls. I hope you don't mind but I can't live on cum and pussy alone." She laughed as she said it.

I apologized for not being a better host and meant it.

Her hand found my cock and gently stroked it. "You are the host with the most! I've been sitting here watching you for about an hour. I watched your cock get hard and then go soft three times. I wondered what it was you might have been dreaming about. Could it have been this?" She bent over and took me in her mouth. I was instantly at full mast and she just smiled as she pulled back and straddled me to impale herself on my cock. "Or this?" She bounced up and down like a yo-yo on a string for a few minutes and then got off and turned around. "Or maybe this?" Again she impaled her cunt and bent forward to show me her brown rosebud. I wet my finger and pushed it in her anus. She shrieked with pleasure/pain.

Finally she came hard and took me along for the ride. When we were both done I grabbed her hips and pulled her dripping pussy to my face. I licked her clean as she sucked me clean and dry. She reversed her position and slid up next to me.

"You know last week was a first for me. I told you I had been with four other guys before but you're the first man I actually slept with. It was so comforting to feel the heat of your body close to mine, and when you snored it just made me hornier. I hope I'm welcome to spend the night again?" I assured her that she was. Her purring demonstrated her gratitude.

"You also seem to have a fascination with stimulating my ass. If there is something else you want to do with it I'm open to the idea. I heard a couple of women in the break-room at the casino talking about it one night and they both seemed to love it. It's yours for the taking if you want that. I also saw it on a porn video and it's something I really want to experience."

I said nothing. We got up and made sandwiches before moving to the balcony to watch the action below. As we ate she just took my hand. "Well?"

I told her that the first time would be very painful and I didn't want to hurt her.

"Shouldn't that be up to me?" I couldn't really argue.

"Tonight my cock will find its way into your ass. I promise."

We got dressed, went out, drank some beer, and shot some pool. She was very good and managed to beat me a couple of times. I learned that she had a pool table in her house as a kid.

After some dinner we headed back. As we went though the gate to the community I could hear the tempo of her breathing hasten. She wanted this badly. I promised myself I'd be as gentle as possible. I once had a girlfriend who took a dildo, that was approximately the same size as me and just jam it in my ass. It hurt like hell. I didn't want to hurt this tender young virgin ass any more than necessary.

Princess walked up the stairs ahead of me. We didn't bother looking out at the pool because we were both so intent on what was coming. I slowly undressed her, something we had never had the fun of doing before since we were in a naturist resort.

I'd never understood why young women today seem to wear endless layers of clothing before. She had on a light rain jacket, followed by a shirt, followed by a chemise, followed by a bra. It was like peeling an onion with each layer down getting sweeter and sweeter As I took off her bra I took the time to suck each brown nipple until they were hard and then gently nibbled on each until she squirmed. Below the waist it was jeans and lacy panties that matched her hot pink bra. I spent twenty minutes stripping her and enjoyed every one.

She, on the other hand, was much less patient. She literally pulled two of the buttons off my shirt before pulling down my shorts and boxers without even bothering to unzip the fly or release the catch on my shorts. She flopped on the bed on her stomach and picked her ass up.

There was no way I was going to make this any more painful than I had to. I reached into the night stand drawer and pulled out a squeeze bottle of almond oil and a tube of warming gel. I told her to relax and let me take control.

"I just want you to do it!" I told I would, but all in good time. I sprinkled drops of almond oil on her back. I watched her shiver as each drop hit.

"Just relax and enjoy the massage. The rest will come slowly." I slowly rubbed the oil into her shoulders and upper back. I could feel the tension ebbing away. When the top was relaxed I let my hands slowly work down to her lower back and finally her cheeks.

I rubbed the oil in there and gently pried her knees wide open. I scooted down and began to lick her exposed anus. She moaned in delight. I lubed up my long middle finger with some of the warming gel and slowly pushed it in her. She stiffened at first but slowly relaxed as I slowly and gently finger fucked her ass. After a few minutes I applied more gel and went in with both index and middle fingers. Again I was slow and gentle but after awhile I spread my fingers a bit to loosen her up.

Each spread was reacted to with a small flinch but eventually I saw her sphincter widen and start to ooze her own lubricant. I couldn't resist tasting it and replaced my two fingers with my fat tongue. She began to climax as I fucked her ass with my tongue. When she was done I backed off and lubed up three fingers all slid in fairly easily and I knew we were close.

I slowly fucked her as deeply as I could, spreading my fingers wider with every stroke. She was whimpering and begging for my cock. I lubed her anus up and began to slide in. I got just the head in and she shuddered a little. I let it stay there as I rubbed her back and made her relax again. When I felt her loosen up, I pushed in another inch. Again I paused and let her adjust. After a minute or so I pushed in the third inch. Another pause and I began slow strokes that reached a little deeper with each one.

I was about halfway in and she screamed at me to just do it. I squirted some more lube on my shaft and pressed in as far as I could. My pelvis was pressed against her ass cheeks. Her moans of pleasure assured me that she loved it.

I bent over and in a soft voice asked if she wanted all of it. "Fuck yes! Give me all that cock!" was her response. I pulled her up to her knees and as I did I slipped in deeper and deeper. Finally my balls were laying on her dripping pussy. I pulled almost all the way out and asked if she was ready. I didn't wait for an answer but began to stroke harder and faster plunging in to the hilt with each thrust.

"Of fuck that feels good!" It was almost a scream. I knew I was close and I hate to come before my partner. I reached around and began to pinch her hard little clit. Her orgasm brought on mine and she was begging me to fill her with my hot cum. I did just that. With each stroke in I could feel my cum gush out and drip down my balls.

When I softened and slipped out I rolled over on my back as she laid back on her flat belly. I asked if she was OK. "I'm way above OK . That was better than all my sexual experiences put together." She looked down at my cock. "Is that gel stuff safe to eat?" I assured her it was and she slid down and began licking my balls before taking all of my shriveled cock in her mouth and sucking while her tongue loosened any residue of her ass and my cum from my dick. She could get me all the way down when I was soft. I loved it.

She looked up at me and smiled as she licked her lips. "I guess I can add 'Dirty Cock Sucker' to my resume' now." We both laughed. "Will you do that again in the morning?" I assured her that I would if she wanted me to. "I want one variation. Before you cum I want you in my mouth. That's probably the best of two worlds."

We snacked for dinner and went to bed and sleep after a quick shower. I don't think I'd slept so well for years. I woke in the early morning with her long tongue probing my ass.

She moved up next to me. "I may be addicted. I barely slept just thinking about it. Please do it now!" She rolled over on her stomach and rose on her knees.

I moved behind her and began to tongue her anus. Yesterdays actions had certainly loosened it up and with just a little effort I could push my tongue in. Her moans demonstrated her pleasure. I lubed two fingers and pressed then in. The third followed soon and I stretched her out. After a few minutes I substituted my dry cock and none too gently buried it in her. She yelped at first but then began to beg me to fuck her hard. I did as she wanted and reached around to pinch her clit. The response was immediate.

oldbob68
oldbob68
176 Followers
12