Traveling with Charlie

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We slept until six, showered, and left. On the way out of town we stopped for breakfast and I ordered an Oyster Rockefeller omelet and a couple of Bloody Mary's. The omelet was huge and we shared it. As we drove out of town she snuggled up next to me.

"I've never known a man like you. You treat me so nicely. You're gentle and kind and caring. I haven't even gotten to your skills, talents, and features." You have the nicest and best cock that has ever pleasured me or I have had the privilege of pleasuring. You taste better than any of the multitudes of cocks I have sucked in the past, and I'm talking before, during, and after you cum. When you fuck me you know exactly the right speed and angle to give me maximum pleasure. As I fell asleep last night I laid there and wondered if you were an angel. Every other man in my life has just thought of me as a place to shove his cock and unload his seed. You treat me like a person. I can talk to you and tell you anything without you judging me."

"You and I have broken the rules of whoredom. You kissed my mouth. I've never been kissed on the mouth before by a man. Your kisses are tender yet passionate."

"You ate my pussy better than any of my fellow female whores ever thought of doing. When your tongue touches my clit it feels like a cattle prod just shocked it.

"Whores hardly ever cum. We will occasionally but generally we just fake it to make a client feel like a real man. You are a real man."

"And the last thing is that a whore never falls for a guy. It just doesn't happen but I'm falling hard and loving it as scary as it is."

I pulled her close to me and wrapped my arm around her. My hand naturally fell to her tit. I massaged it slowly and gently. "I love it when you do that so tenderly. You make me feel like a woman and not just some whore. Why the hell did any woman let you go?" I tried to explain her loss of libido but I really never understood it myself. I reiterated to Charlie that she could hang with me for as long as she liked. We hugged the coast on 98 until we hit 19 at Perry and headed south. I welcomed her to redneck country. I explained that this was just about the last truly country area left in the state. She laughed and her hand found my zipper. "How about me making this head purple while your neck gets red?"

She began to stroke my hardening cock until I told her I had to blow. She took me in her mouth almost just in time. She sucked me dry, wiped the excess cum from her face, and licked her fingers off. It had been years since I had a roadie hand job and told her so. "That's the first hand job I've ever given. I went straight from nothing to sucking!" I told her it had actually been years since I had anything but a self administered hand-job but hers was fantastic.

We stopped in Taglis for some pulled pork sandwiches. She said they were fantastic and I told her that nothing tasted as good as her sweet cunt. She blushed. "Do you know how difficult it is to make a whore blush?" We got back in the truck and once again her head found my lap as she napped. She woke three hours later as we pulled into the complex where I lived. I showed the guard my ID card and he opened the gate. Charlie looked around. "You do know that no one here seems to be wearing clothes don't you." I just laughed.

"Welcome to my little world. I guess I forgot to tell you that this is a clothing optional complex. Believe me, It's not as sexy as it sounds. No overt sex is allowed outside and if a guy gets hard he's expected to cover it. We mostly just enjoy the feeling of walking around without the confinement of cloths."

"Can I take mine off?"

"You'll probably make a lot of guys glad they have towels to cover up their dicks."

She stripped before we got out of the car. "My god I love this. I feel so free!" I told her that was the total concept.

We carried our luggage up to my apartment. Watching her bare tits being pushed out as she pulled on her backpack probably moved them up to triple D's. My neighbors didn't fail to notice, nor did the pizza delivery guy a half hour later. I called George and told him I was back and would deliver the truck at noon tomorrow.

When it was dark we walked, hand in hand, to the pool and had a leisurely swim. In a way it was hard to keep my hands off her as she floated around but in another way it just built the sexual tension.

"God that felt so good! I've heard about skinny dipping before but have never done it. I loved it!"

"So did all the guys sitting around the pool. I never saw so many towels being used," I said with a laugh.

We watched some TV movie from the bed. I snuggled against her like I had the night before but this time she guided my cock into her warm and welcoming cunt. She asked me not to move but to just let her cunt do the work. I did as she asked and just kept it buried in her tunnel. The same control she had demonstrated by picking up a bill seemed to extend all the way up her vagina. I felt like I was being sucked off by her cunt. I could actually hear the suction she was creating. She felt me blow and came along with me. We both had stationary, long, and soft orgasms. It was the most intimate moment I had ever experienced.

I didn't pull out and just held her tightly. Neither of us said a word nor did we have to. Still in that position we fell asleep. Unbelievably I was still inside her when I woke at six. I felt myself getting hard again as I reflected about the night before. I began to stroke softly and gently. I could feel the remnants of last night cum in her cunt and apparently so could she. I reached around her and could feel the dried up cum on her pussy lips.

"Fuck that slimy cunt. Enjoy your own sloppy seconds. Fuck me hard! Puleeeeze!"

Keeping my cock buried, I rolled on my back so she was in a reverse cowgirl position. I held her tits hard and she rode my bull hard until we both came. Still keeping me in she turned and fed me her tits, one at a time before laying her head on my chest and falling asleep again. At nine she woke me by massaging my balls with one hand while her cunt began to massage me to hardness again. When I felt that I was hard enough I rolled her on her back while still staying in and began to slowly fuck her in the missionary position. This time was gentle and tender again and once again we joined in a mutual climax.

She pushed me off, put me on my back, and took my wet and soft cock in her hand."My, my what have we here. It looks like well aged cum to me. She followed up with her mouth. When she had me hard again she gently cradled my balls and asked I thought I had a little more for her. I told her that honestly I had no idea. She mounted me and slowly lowered herself on to my cock. I could feel and hear the cum squish out again as she pumped up and down. I reached out and squeezed one nipple hard while hand I pressed my other thumb firmly to her clit. Her climax once again pushed me to mine and I gave her what had to be the last few drops of cum left in my balls.

"That was a one man gang bang!" She pulled off and went down to lick me clean. I knew what would please and surprise her and slid down between her legs and sucked every bit of cum out that I could. When my mouth was full I kissed her deeply and let it slowly drip into hers. She actually gargled it before swallowing and smiling. "Best morning mouth wash ever!"

We showered and I cooked some eggs and toast. We ate naked on the balcony. "My god I love this feeling! I haven't felt this free since I sunbathed for Mr. Ames. I just held her hand. This part was not about sex.

A little before noon we headed over to the bar to meet George. He spent as much time checking out Charlie as he did checking the truck and told me that maybe he and I should take a road trip together some time. I had told him about my experience on the last one. I wasn't sure he believed me. We hung out for a bit and all the other barflies ogled her big tits.

She offered to buy me lunch and I suggested a place I knew that was about twenty minutes away. It's in a marina and is a very peaceful setting. We sat on the balcony and could see all the way out to the beautiful blue waters of the Gulf of Mexico in the distance and hear the pleasant clanking of sailboat lines slapping the masts. I ordered conch fritters and seafood gumbo for each of us and we ate in silence. She paid the bill and we left with about ten guys eyeing her fine ass and probably wondering what she was doing with an old coot like me.

I thanked her for lunch and she thanked me for the restaurant choice. "It seems like you know how to live the good life. My life has centered around my occupation of sucking cocks. I told her there were joys even in a moderate retirement and she certainly was one of them.

"I know I have to get back to work but it'll be hard to leave. I saw on your calendar that you have a doctors appointment tomorrow morning. I should get back home soon so if the offer is still there to take me to Daytona and back we should probably do it in two days. You can just drop me off at the airport on the way in." Her eyes were starting to well up with tears and I know mine were as well.

We went for a swim when we got back and once again she made all the men hard as she floated around on her back with her red hair flowing around her and her dark pink nipples just breaking the surface like twin periscopes or snorkels. We had stopped at a grocery store on the way in and bought some ground sirloin, buns, and corn. No cooking is allowed on our balconies but there is a communal grill down by the pool. We headed there and I cooked the burgers and corn. She was still the center of attention and when she was done with the ear of corn she held one end to her lips. It was a big ear, about a foot long and fat.

"Should I?" She asked with a smirk. She knew all male and some female eyes out there were laser focused on her. I just nodded and while holding on to the stem, she leaned back, and took the whole thing down her throat. She pulled it out and made love to it with her tongue just like she had done for me the first day. The women boiled and the men gawked and covered themselves up. "Was that too much," She asked? I just shook my head in awe of her talent.

"Tonight I'm going to give you best beat blow jobs you've ever had. You'll be begging me to finish you each time. Tonight I pull out all the stops so you never forget me." I assured he that there was no way in the world I'd ever forget her and the fantastic five days and she had given me.

She did what she promised. She went from high suction to no suction, from shallow to so deep that I just blew straight down her throat. She was amazing. We slept until my alarm went off at nine. She woke as I was getting dressed. I told her I should be back by noon and asked if I could bring her anything.

She smiled, "Bring me back that big hot cock you'll stick in my ass. I'll be ready and waiting for you." The doctors appointment was routine and she asked me how the pills were working for me. If Charlie wasn't waiting for me I probably would have invited her to find out, but my cock had a date with a gorgeous ass and I was in a hurry to get home. I told her they worked fine and thanked her.

When I got home I found Charlie bent over the arm of a stuffed chair. On the table next to her was her jar of cocoa butter. I stripped and it only took a few strokes to get me hard enough to slide into her waiting and wanting hole and begin to hammer her. With all the recent activity my sack had almost grown back to the length it was in my twenties. As I hammered her ass my nuts were striking at her clit. She came and as her sphincter tightened around my hard cock. I came with her. I finally slid out and knelt behind her to worship her ass with my tongue. I reached around to stroke her clit and she came again for me.

That got me hard again and once again I pressed my cock into her ass. She came but I didn't and she knew it. "Let me lick that chocolate Popsicle and taste what the filling is. She found out soon enough.

We went out for dinner and ate quietly. It was obvious to both of us that we didn't want the journey to end. The love we made that night and in the morning was sweet and tender. We got on the road late enough to miss the traffic nightmare that the I-275 and I-4 intersection had become. It took us about two hours to get there and another thirty to find an open beach access ramp. I was surprised at the ten dollar toll but she insisted on paying.

We drove north a few miles and found a place to park so she could dip her toes in the Atlantic for the first time. We strolled the beach quietly and hand-in-hand for about thirty minutes. "Would you like a beach blow job to remember this trip by?" I told her that I hoped I'd see her again but that I would love one. My SUV has bucket seats so it wasn't easy to find a position that was comfortable for both of us. She suggested that I open the hatch door and sit on the bumper.

I took the suggestion and she knelt in the sand and worked me for a good thirty minutes before she let me cum. She was truly a master. After she had taken and swallowed every last drop we continued north and hit a little seafood shack that I remembered from years ago. I was pleased to find it still open and still good as we lunched on steamed clams and chowder. We were both pretty silent.

It was time to head back so she could make her flight. On the way she took out a key and handed it to me. I asked what it was for. "It's for unit 269. That should be easy to remember. It's in the condo section and I bought it yesterday. You are welcome to stay there for free and look after the place for me. I will be visiting quite frequently and I may bring company with me. I've been texting Kim, Darla, and my mom about our adventure. I hope you don't mind. They would all like to meet you. I know that what we have developed in the last few days transcends just great sex but I also realize that men occasionally like a little variety. We can provide that and they'll all love where you live and hang out."

We both shed a few tears at the airport. I really didn't want her to go and she didn't want to go either. I gave her a long hug and a soft and gentle kiss as she got in line for the security check. When she was safely through I watched her beautiful and receptive ass as she went up the escalator. She didn't turn around but I detected a little wiggle as she reached the top.

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13 Comments
AnonymousAnonymousabout 2 years ago

Don't listen to any of the criticisms. Your story made this old doll's pussy drip. That's what I call a recommendation!

AnonymousAnonymousover 2 years ago

Awesome, great story. Thanks for sharing.

AnonymousAnonymousover 2 years ago

WONDERFUL STORY. TOO BAD SHE COULDN'T SETTLE DOWN AND HAVE A FAMILY AND RAISE THEM RIGHT. SHE WASN'T, AND ACTUALLY WAS LONELY UNTIL SHE MET THIS MAN...

MrViixMrViixalmost 3 years ago

Fun story. Thank you!

AnonymousAnonymousalmost 7 years ago
Fun fantasy

In many similar cases, the guy would have woken up in Oklahoma motel to find his money and friend's truck long gone.

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