Harry Charleston Rides Again, Pt. 01

Story Info
Harry needs to choose from some sexy women.
17.1k words
4.48
3.1k
8
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Harry Charleston Rides Again

Gwen was young and so unbelievably beautiful. She had only celebrated her nineteenth birthday recently. Gwen had a face like an angel. She had beautifully shaped breasts, about the size of a large grapefruit, with large dark areolas and thick sensitive nipples. Her waist was very slim and her hips wide, with a fantastic ass. Her long blonde hair was flying everywhere. Her blue eyes locked on Harry Charleston.

Gwen was grunting and moaning as she fucked him, with her riding on his prodigious member, and Harry was trying so hard not to cum. She was very tight, almost virginally tight, and her grinding and fantastic squeezing were about to put him over the edge into a suborbital orgasm. He was going to shoot his jism into her like a rocket. Gwen beat him to it, screaming his name. She slammed her tight cunt down on his huge, hard, happy dick!

"HAAARRYY, I'M GONNA...UGH!" she screamed as she came hard, her head thrown back and flaxen hair wild in abandon. Gwen was having the time of her life.

"Ohmygod, Harry! I'm coming again! Ughhh! Ooohh! Yes, fuck me, yes! OHH YES! AHHH! OH FUCK ME, HARRY!" She squirted and climaxed for the fifth or sixth time on him. She lost track of her huge shattering orgasms.

Harry couldn't hold back against this orgiastic onslaught, her cunt spasming on him with such delight for both of them. He filled her happy hole with a massive load of cum, "Gwen, I'm coming too!" As he spasmed and rocketed his juice into her perfect body. It felt like a gallon of jism. Gwen squirted her juices again and at the same time she clenched her PC muscles and clamped her hot snatch on Harry's dick with amazing strength. Harry's orgasm was amazing and wonderful inside the sexy young girl. She had true pussy power!

His hands grabbed her big tits as she and he stopped for just a couple of seconds, in full orgasm, as they exchanged love juices, and for a few seconds, they were but one person, locked together in sex and spirit BOTH. They were united and so delighted. What a glorious feeling to be one with another, as close as two people could ever be. She was his, and he was hers, and they were... inseparable, if but for a moment, a wonderful, magnificent experience for both of them. It seemed almost...mystical, magical.

But like a high-performance engine, she thrust at high speed again, her hot snatch grasped at him, squeezed at his dick, she squeezed every drop of his sperm into her hot wet gash as she hit her final orgasm on top of him. She clamped her tight juicy quim on his big hard dick and locked onto him in her gut-wrenching climax. Gwen had a magnificent final orgasm.

"Holy shit, I just came again! You are the best fucker Harry Charleston! I am so happy!" She wept into his chest as she finally stopped and fell forward. She was kissing him and crying at the same time.

"Well, thank you, Gwendolyn Jones, for that lovely compliment. I find you are a wonderful fucker yourself, and that magical muff of yours has made me very happy indeed. I am amazed at how much control you have over that tight little cunt of yours. I feel like we are welded together... and I like it very much." Harry was honest.

Harry's hands had automatically switched from her huge breasts to her perfect heart-shaped ass, as they both remained tightly locked together, his cock all the way deep inside her, up against her cervix, still spewing his semen into this perfect fantastic female.

It was a sexual and spiritual moment for both of them. Neither seemed in a hurry to disengage their frantic, excellent coupling. It was a rare thing that they both felt that perfect fit of body parts and feelings as well... as though they were made for each other, lock and key, but they didn't disengage in the slightest. Her legs were wrapped around his waist, and she was not letting Harry withdraw from her spasming snatch even one little bit. She was his, and he was hers. She looked so happy. Harry was smiling. Harry never smiled, but today he seemed ecstatic.

"Thank you, Gwen. That was more fantastic than words can describe. I feel like I'm part of you now, and you are a part of me. I know that sounds so dumb and corny, but it's the truth too!" She nodded in complete agreement and squeezed him tight again with her strong cunt muscles, face smiling as she did so. He enjoyed her fantastic cunt kegels. She felt almost as tight as a virgin, maybe tighter since she squeezed him of her own volition. She CHOSE to embrace his happy helper, as he penetrated her delicious depths. She could probably crack open walnuts with her powerful pussy! She was locked on his meatpole, and she was happy being there. Gwen locked herself on Harry, not wanting an extra millimeter to come between them. Her legs and arms pulled her closer to Harry.

"I can't thank you enough for saving me from... " she started to tear up from her almost rape. Gwen shuddered a seventh time on Harry's dick. She squirmed and bucked on him uncontrollably, forcing the last of his cum into her body. It was such a hard orgasm; it was almost like a seizure! She was weeping and coming at the same time.

She loved his powerful pulses that gave her so much pleasure. Gwen felt every single spurt inside her. Harry came very hard inside the beautiful woman, pushing a massive amount of sperm into her super sexy snatch, deep into her cervix. That one was a surprise orgasm, something Harry almost never experienced. She shuddered one more time when she felt his seed pulse again and again, seeking her womb.

Gwen liked the idea that his powerful thrusting and hot jism may have done the job and impregnated her happy little pussy. She wanted his son to be born of their union, but a little girl was just fine too. She wanted to be HIS, plain and simple.

"Did you just cum AGAIN?" Harry asked the shaking young woman.

"Yes. I can't help myself with you, Harry. I am yours now. Thank you for saving me, and giving me the best sex I ever experienced, and for being one with me. That was so great, so unbelievable, Oh yeah!" Gwen's cunt was still locked on the big dick in her. The fit was pure pleasure for both of them.

Harry got up, put her hands on his neck, with Gwen still wrapped around him, and he held her up by her perfect ass and his dick, deep inside her as he walked into the bathroom and placed her gently on the vanity. He tried to pull out.

She says, "NO, no, don't go. I want you deep in me. It feels so perfect!" She was grinding on him again, and her clit up against him as she fucked him. Harry amazingly responded. He lifted her legs slightly, and almost punished her with his cock, pulling out and slamming in, for many, many minutes... Until they both came again! Grunting like savages, they both yelled, "COMING UGH," and grunt throughout their brutal mutual climax. She was completely full of Harry's jism. She was very pleased, very pleasured!

"I can't believe you fucked me into the bathroom, clamped on your big dick!" She was astonished. No man had ever fucked her so completely, so wonderfully! No man had ever fucked her standing up and walking so effortlessly and giving her such pleasure beyond belief. Harry was an Olympic fucker, no doubt!

"I have my moments! What about you? You squirted all through one of your orgasms. Do you always come this much? This hard? You almost squeezed my dick off." Harry liked her sex style, vigorous, to say the least. Gwen had responded to his every touch in kind and with equal passion. They seemed so sympatico.

"Never have I cum this good, this many times, or had the spiritual bonding we had today. I am so enthralled by you, Harry. First, you save me from rape, and then you fuck me to death!" They both laughed at the irony there.

"Harry, truthfully, I want a real relationship with you. I do have a problem, however. I... I... have a boyfriend. He is nothing like you, but we have been going out for about six months. We had a huge fight last week... I don't know where I stand with him, and I want to figure out what to do. I can't be with both of you, can I?" Gwen seemed very confused. She had just met Harry and felt like she belonged to him already, but she had six months with her boyfriend, and he deserved at least some serious consideration.

"No, you will have to choose. I did not come to your rescue in hopes that I could get in your pants. I just did what was right. I know what we just... experienced...was wonderful, but I see your point. You have to be right about things with him. Figure things out in your own mind and heart. Thank you so much for everything you did for me and to me!" Harry pulled out of her and turned to piss into the bowl. She felt immediately empty and wanted him back in her cunt. Gwen shoved toilet paper into her gash to keep his cum inside her. She wanted it. Gwen pulled out a strand on her fingers and ate it. She liked his taste! She licked more of his jism off her fingers and savored it.

Harry was waiting for his erection to calm down so he could piss, holding his dick and aiming it.

Gwen jumped off the counter and said, "May I?" and grabbed his dick just as his stream started. She directed it into the bowl. She was fascinated by his dick. She liked to watch his pee. Harry was done, and he was going to wipe off his penis, but Gwen had other ideas. She sucked him into her mouth, cleaning him with her tongue and mouth. Gwen reveled in being naughty and dirty! She didn't mind a few drops of Harry's piss in her mouth. Gwen loved having his cock in her mouth. She licked him clean as a whistle.

"Thank you, dirty girl! Here." He handed her mouthwash.

"So, are we an item? Or was this just a one-time thing? It meant quite a lot to me. Maybe it didn't mean as much to you?" Harry asked her tentatively.

Gwen gazed at him, and the thought struck her that she really cared for this wonderful magnificent man; she wanted more of him, and suddenly her boyfriend seemed inept, stupid, and almost misogynistic to her. Why had she not seen that until she met Harry?

Harry was like some crusading white knight, bound by his own set of rules, but willing to sacrifice himself to save her from harm. She was quite turned around by this entire episode.

"Harry, I've got to think about this. It was wonderful. You were so awesome! It was the best I ever had, but I owe it to Paul to at least make a decision. I literally just met you! I've been with Paul for some time now." She tried to explain as best she could.

"So I got to think about this. I owe that to you too!" She thought she knew which way she was going. "You saved me, Harry. For that, I am eternally grateful, but now, I need to think. I have a tough time thinking when I'm close to you because I...l want to fuck you again and again, repeatedly. I am like a moth to a flame with you!" Gwen revealed to Harry.

Harry didn't say it, but he felt the exact same way with her. He thought to himself it was just the heat of the moment. However, the fact that her pussy was such a nice fit for his equipment was not lost on Harry. They fit together like lock and key, almost perfectly.

"It's OK. You should make a decision, and not lightly, just based on great sex. But until I hear from you, we are non-exclusive, obviously since you have a boyfriend already. Give me a call when you get horny, and want to try me out again." Harry was actually ready then and there, but he didn't want to push her into a bad decision. Great sex does not mean a great relationship. It frequently had nothing to do with the relationship.

"Thank you, Harry." She kissed him for a long time. "Harry...you're not married are you?" She prayed.

"No. Divorced. She traded up, broke my heart, took my kids and whoosh! Gone with the wind. I guess she lived in France for a few years. I heard through my attorney the dirty fuckin' bastard is cheating on her now. Karma is such a bitch. Poor thing. Here." Harry handed her a key.

××××××××××××××

"What's this? A key to your house?" Gwen was astonished.

"So you can come over when you need to. Just call first, let me know so I can tidy up." Harry also didn't want other women meeting each other accidentally in his house. That would be... awkward.

"I may have to throw out any stray naked women!" Harry fessed up.

"Oh hell no, I'll just go for the three-way!" Gwen responded. They both giggled. She was thinking that she meant every word though! Dirty girl.

"Harry, maybe you could do me a favor? My Mom is also divorced, she hasn't been out with anyone nice in a long time. Would you take her out dancing? I would greatly appreciate it, Harry. She gets very lonely sometimes." Gwen was worried about her mom. She was almost a shut in sometimes.

"Sure. Is she as pretty as you?" Harry asked.

"She is very beautiful. Thank you. Here's her number, and her name is Marilyn Jones." Gwen kissed him, he kissed her back. Then she was gone, as Harry watched her round, wonderful ass shake this way and that, he was amazed she wanted him. She was so devastatingly beautiful. She looked back and caught Harry staring at her swaying hypnotic ass and she smiled at him. She didn't realize her ass was perfect.

*********

"Hi, Marilyn? My name is Harry Charleston...Your daughter Gwen asked me to give you a call...Would you like to go out next Saturday night?... Me? I'm tall, dark, and handsome. I'm about six foot, I'm about two-twenty. Dark hair and dark eyes. I love to dance...Sure I'll send you a picture." He texted her a pic.

The picture he got back is amazing. Marilyn was really gorgeous and looked just like her daughter, except her hair was darker blonde. They agreed to dinner and dancing for Saturday night. Marilyn looked quite sexy. Why is she not dating? Something was going on there. Perhaps she was depressed. Lot of that going around.

*********

Saturday night went well. Dancing all night, Harry and Marilyn had a great time until he had to relieve himself. Harry went to the men's room. He came back to find Marilyn Jones dancing with someone else, a huge guy who told him she was now his date. Harry did not take this disrespect at all well. His anger level rose geometrically.

"Excuse me, you're dancing with my date," Harry said, trying to remain civil.

"She's my date now, old man, go away now. Shoo!" He shoved Harry. Big mistake. Harry did not take kindly to being shoved. Harry is not a man to be trifled with. Anger flowed in Harry's veins like fire on gasoline.

Harry punched him square in the face, and the big man went down, all three hundred pounds of him. He was knocked out from one punch. Harry was very good at all forms of hand-to-hand combat. He was an expert. He could have easily killed the asshole, but he didn't want to go to jail. He only wanted to get his attention. Harry might have hit him a little bit too hard. The large man was out cold.

They left. Harry had no desire to meet the police. He took notice Marilyn looked very disappointed now, and he realized she had loved the attention shown by the big Neanderthal, and the fight over her was also fun for her. Harry felt set up. This had been previously arranged for sure. She knew this very disrespectful fucker. Marilyn had some kind of relationship with the huge guy. They had not counted on Harry's expert fighting abilities.

"Sorry, we have to go now! I don't feel like spending time in a jail cell. I am sorry for losing my temper Marilyn," Harry told her. They got in his car; he could see the true disappointment on her face.

"Well, I see you were really enjoying his hands all over you. Do you want to go back?" Harry asked her. He was truly pissed. Some fucking date.

"No, take me home, please Harry." She said quietly. Harry thought, "No problem!"

*********

Harry gave her a chaste kiss on the porch, like a kiss to your grandma. He was suddenly much more defensive of his emotions.

"Would you like to come in?" Marilyn asked with a purr.

"No thanks." Harry was quite unhappy. He felt like the whole evening had been some kind of set-up, which Harry had inadvertently fucked up by knocking out Mr Neanderthal.

"Why not?" She asked.

"Cause we have a great time all night, I'm gone for five minutes, a Neanderthal has his hands all over you. I get pissed off. I knock him out." He looks her in the eyes. "Then I find out you were enjoying it... Nah, we're done here, I don't like being played. I am sorry I knocked out your real date Marilyn." Harry was pissed. "Thanks for an, ahh... interesting evening."

Marilyn went in sadly and closed the door. He thought "good riddance". As Harry turned to leave, a soft voice says, "Don't go just yet."

He saw a beautiful woman

sitting in the dark. Her name was April Conner.

"I would never have mistreated you like that," April said.

"Who are you?" Harry asked.

"Her slightly older sister, April. April Conner."

"Wow, you are beautiful!" April has darker hair cascading in gentle waves around her face, the face of a movie star. Full lips, high cheekbones. Wow. Beautiful! Possibly more attractive than her dumbass game-playing sister.

"THANK YOU!" April replied with a great smile.

"I should have asked you out," Harry said.

"You still can, Harry. The night is young. I know a place where we can dance."

"The hospital," Harry said. He groaned a little. His hand hurt.

"Why?" April asked.

"I need an x-ray. I think I broke my hand on his face! Still want to go?" Harry asked. His hand was swollen and getting worse. Neanderthal had a hard face, even if Harry had knocked him out. He might have broke a bone, maybe.

"Yes," she says."I'll drive Harry, so you can rest that hand. I think you broke it. It looks kinda bad, all swelled up."

They went to the hospital. The nurse asked April to wait in the hall, as she can't be in the x-ray room when the machine is running. He met a very beautiful oriental woman doctor. Her name was Dr. Lee Ann Berthold. She was very petite, and her facial features were perfect, almost exquisite. Her skin wss flawless, and her eyes a deep brown, behind her glasses. She looked extremely intelligent, but that was just looks. But then, she was a doctor, so she must have something on the ball.

"How did this happen?" asked the petite doctor. She thoroughly examined his hand and wrist. He had hit something or someone very hard. "I don't think it's broken, but bashed up pretty good. I'll check the x-rays to be sure. Can you move all your fingers? Wrist? I think it's bruised pretty badly." the petite doctor spoke.

"I got into a little argument with this huge guy who had decided to try to take my date. I convinced him, er... otherwise." Harry gave her the short sanitized version.

"Was he six-two, and a real asshole?" Lee Ann asked.

"Oh, you know him?" Harry quipped. He smiled at her.

"I treated him. He has a bad concussion. He said you sucker punched him-" the doc explained.

"-I did no such thing! I might have hit him a little bit too hard though," Harry admitted.

She smiled. "From the looks of it, he's got a very hard head, like a rock," she said.

"Thing is after all that, I found out my date, well... she really liked his rough treatment of her. She and I will not be going out again. I felt like the whole thing was a set-up. I guess I messed up their plans a bit." Harry was very pissed.

Lee Ann says, "I would never do that to you, Harry... Please call me. I have off Monday and Tuesday. I love to dance." She kissed him and gave him her phone number. He smiled. He doesn't get kissed by doctors that often. Especially beautiful ones! He mentally made a few plans.

"Call me. I want to fuck you." Lee Ann whispered in his ear. She touched his face lovingly.

He got up to leave, his date April Connor saw it all, the kiss at least.

"Wow, Harry, are you popular." She was a bit irritated, maybe a little bit jealous.

"How about the dancing?" he asked her.