Twice Lucky - Cover

Twice Lucky

Copyright© 2003 by Joe J

Chapter 25

Time Travel Sex Story: Chapter 25 - If you knew then what you know now, how would you act?

Caution: This Time Travel Sex Story contains strong sexual content, including mt/ft   Ma/ft   mt/Fa   ft/ft   Fa/ft   Consensual   Romantic   BiSexual   Time Travel   DoOver   Incest   Brother   Sister   Safe Sex   Oral Sex   Anal Sex   Pregnancy  

Once inside the front door, Debbie turned to Charles and kissed him the way she had been dying to all day. Charles responded in kind and Debbie knew now was her moment to seize. She pulled back from the kiss and looked up into his eyes.

“Daddy, I want you to make love to me, and I think you want me too. I know this isn’t going to affect your marriage. I know how much you love mom. You know it won’t scar my psyche, because you know I don’t want to steal you and make you mine. But I love you and I crave your touch.”

Charles did not say anything, and Debbie momentarily thought she had miscalculated. Then Charles gave her his answer by taking her hand, and heading for the stairs. Carpe diem, carpe Debbie. He turned down the hall and led her into her bedroom. Debbie took over then and pushed him back until he was sitting on the edge of the bed. She backed up two steps, kicked off her shoes, and stripped off her blouse, bra, and shorts. Then, with only one remaining garment, she seductively swayed towards him and stood between his legs. She took his hands and placed them on her hips right above her white panties with the pink hearts. She dropped her hands to her sides and waited for him to act. Charles hooked his thumbs in the waistband of the panties and eased them over the swell of her ass. Then he knelt down off the bed and slipped them down her long muscular legs. When he reached her feet, she put her hand on his head and stepped out of the little crumpled pile of nylon. He lifted his eyes to her face, taking in her well-groomed pudenda. As he smelled he scent, his nostrils flared involuntarily.

Debbie pulled him to his feet and started unbuttoning his shirt. She stripped him naked and, while on her knees, took his prick in her mouth without hesitation. ‘He’s a little smaller than Jake -- but only a little,’ she thought as she sucked him until he was slick with her saliva. Debbie stood up and gracefully lay back on the bed.

“Come and get me, Daddy,” she said huskily, “You have never had a pussy more open and ready for your dick than mine is right now.”

Charles positioned himself above her and guided his prick into her. He pushed it in an inch and stopped, savoring the feel of her slit. She was as steamy hot and wet as a rain forest, yet as tight as a well-tuned violin string. Before he could feed her more cock her eyes rolled back in their sockets and she started coming.


Across town, Jake was enjoying flirting with his two favorite big blondes. Erika was an inch taller than his six-one and Helga was an inch shorter. They both felt wonderful in his arms. Erika said she had to run to the store for a minute and asked Helga to entertain Jake until she returned. Helga sat Jake down on a stool at the breakfast bar and plundered a Tab out of the fridge for him.

“Sven said you two had a nice talk and you were okay with everything,” she said.

“I’m more than okay with it. I’m happy for all of you. Even if it means I lose a girlfriend I know we’ll still all be friends, and the important thing is that your family will be stronger.”

Helga looked at him strangely for a few seconds and then moved towards him until she was between his knees. She put her hands gently on either side of his face.

“That was so sweet, Jake, but you misunderstood. You are family now. You didn’t lose a girlfriend, you gained one. That is, unless you think I’m too old for you.”

Jake met her descending lips and tried to show her with his kiss that he found her not too old at all. He had his hand on her blouse in a flash and was kneading her breast when she stepped back away from him. Helga had on a purple plaid skirt that ended just above her knees and a purple sleeveless button front blouse. She stood there letting him check her out, toying with the buttons on her blouse.

“Erika told me what you did to her last Saturday, Jake. Is that what you are going to do to me?”

Well, the acorn doesn’t fall far from the tree. “Yes, and I think you should call me Jacob.”

He held out his hand and she put hers in it. He pulled her up close to him again. Her eyes were closed and she was taking little panting breaths. Jake stood up and moved behind her. He reached around her and grabbed her hands then stretched her arms in front of her until she was leaning across the bar on her elbows. Helga’s eyes were still tightly closed but her breath was coming faster. Jake reached under her skirt and began pulling down her panties. She moved her knees together to help him. He put her panties in his pocket and flipped up the back of her skirt. She jerked when he rested his hand on her naked and exposed ass.

“I made a mistake with Erika because I didn’t spank her before I took her the first time. I won’t make that mistake with you,” he said.

He ran his fingertips down the crack of her ass until he reached her damp abundant tangle of pubic hair. “For starters, I want most of this gone by tomorrow, you can leave some hair above it if you want, but shave your lips and between your legs clean.”

He stepped back and she started to get up. He brought his open palm down on her ass in a single authoritative smack and she jumped.

“Hold still, we aren’t done yet,” he said.

She bit her lip and moaned as ran his hand along her butt, reached between her legs, and cupped her mound.

“Still want to be my girlfriend?” Jake asked.

She nodded her head emphatically. He plunged his finger in her steamy slit and she came so hard she almost fell down. The deal was sealed when she licked her juice from his finger.


Debbie and Charles had not been idle while Jake was cementing his relationship with the Johanssons. After Debbie’s first orgasm, Charles slid all the way home. As their groins bumped together Debbie went off again. It was like that for the next hour. He could not build up a head of steam before he had to stop while she thrashed about as she came. Debbie lost count of her climaxes as they seemed to run together in one long rippling wave. Finally, she could not take any more. Her muscles were exhausted from clinching so hard, and she was light headed from the almost continuous ecstasy. Charles understood and accepted her promise that she would make it up to him. He pulled back the covers and tucked her in with a kiss on the forehead. She was asleep before he was out the door wondering where all of his sudden stamina had come from.

Charles showered and was waiting downstairs when the women came home. Marisa asked if Angie could stay the night at the beachfront condominium Maria had rented and Helen said yes. As soon as Maria and the girls were gone, Charles took Helen upstairs and gave her the best sex she could remember getting in the last ten years. Helen wondered where all of his sudden stamina had come from.


When Erika came home, her mother was absolutely glowing. Helga had agreed to meet Jake at Coach Nelson’s house the next day at twelve-thirty. She would be shaving and trimming her bush tonight. She could not wait to tell Sven what was in store for her. Erika dropped Jake off at his house at three. Jake knew that, despite Helga’s statement to the contrary, Erika would not have much time for him from now on. She would be focusing much of her energy on Erik. And, once she had seduced her brother, he would want a lot more of her. But they would all still be friends and that was what really mattered.

No one was around when Jake went into the house, even though all the cars were accounted for except Melissa’s Corvette. Everyone must be napping he thought, so he might as well join them to rest up for his date with Gail. Ten minutes later Jake was lying on his bed staring at the ceiling and thinking about women. Was he over doing it with the number of females he had slept with? On reflection, he did not think so. He had real and honest feelings for every woman he had been with, and he was not trying to just bed every chick he ran into. He figured that he had slept with nine different women in five months. He bet that in this era of drugs, sex, and rock and roll, nine was not that big a deal. He had not made any wild promises or commitments to any of them and even went out of his way to insure they knew how he felt.

The landscape sure had changed in the last two weeks though. No doubt about that. Angie was looking for a relationship with Tyler, Debbie was hot for Charles, Cindy seemed to be taking a walk on the wild side, and now it looked as if Erika was fixated on her brother. He was going to try to steer Diane Phillips towards Mr. McClelland and knew that Helga was just sowing some oats with Sven’s complicity. Maria Thornton might become a long-term relationship eventually but he doubted it. Gail Martin had even more potential for the long term, she touched something in him the same way Rebecca did. That only left Helen as the wild card and he was still tiptoeing through that complicated minefield without a metal detector. Nope, no guilt, he thought as he fell smoothly into a contented sleep.

Later that evening Gail Martin again picked Jake up in front of the house. Jake took her to a cozy Italian restaurant for a very good meal that fit his budget. Gail was a terrific date. She was witty, funny, and attentive toward him. He could get used to being spoiled that way. After the meal Jake had Gail drive down to the beach and they walked along the edge of the water holding hands. When they got back to the car Gail said she wished they had some place they could go to be alone. Jake allowed that he had such a place and directed Gail to the coach’s pad. Gail was impressed with the apartment and went to the bathroom to freshen up. Jake sat on the couch until she finished in the loo and rejoined him. The lights were dim, the stereo was playing some mellow old rock and roll love songs, so it seemed only natural they start kissing.

Things heated up quickly. When Jake took her hand and led her to the bedroom, she followed him willingly. Jake undressed her, then got naked himself. He laid her in the center of the bed and started giving her a tongue bath, starting at her left ear. Ten minutes later her fingers were entwined in his hair as she guided him to her dripping vagina. Gail was also going to have to get on the grooming regimen Jake thought, as he dove into the pelt of black shag carpeting that covered her tasty little quim. Jake loved the way Gail responded enthusiastically to his efforts. She actively participated in his search to bring her pleasure by gently guiding his face to where it felt the best. She drew up her knees and rocked her hips as her orgasm approached. When she came she cried out softly and her body stiffened. She was one of those women whose clitoris became too sensitive to continue after they come, so Jake held her close, as they played kissy-face.

Gail licked all her juices off his face, then pulled him on top of her, “I hope you are better prepared tonight, Jake. I will be very unhappy if we can’t make serious love.”

Jake opened the drawer of the nightstand, grabbed a rubber, and hastily rolled it on. He was above her on locked elbows as she guided his dick through her thick curly pubes into the Promised Land. As he slowly pushed into her depths her eyelids fluttered. When he was all the way seated, she pulled her knees back to take him even deeper. She liked a slow pace and a gentle build up, so that is what Jake gave her. She came again after about five minutes and pulled Jake down to lay flat on top of her. While they rested she told him how much she had missed this and how good he made her feel. When she was ready again he moved her so her legs were over his calves, this took the strain of keeping her knees pulled back off her and allowed her to move some. Her fiancé had not been very experienced, plus he and Gail had never experimented, so everything Jake started doing was new and exciting. When Jake rolled her over on top of him, she loved it. In her novel role as cowgirl, she rode him to her first series of successive climaxes that way and that’s how she got him off.

Slick with sweat, they lay in each other’s arms under the covers and talked for an hour. Gail listened to his plans for the future and agreed to become a part of them. That night they established a relationship that, in a few years, saw her evolve into his personal secretary and confidant. The only thing Jake ever held back from her was how he was reincarnated. Gail was one of those people who value their privacy and like being alone. The supporting role Jake was offering was perfect for her. Gail loved to learn and it became the second passion of her life after Jake. She went on to accumulate a number of advanced degrees and was invaluable to Jake as a knowledgeable advisor, skilled in the boardroom. She also became a student in the art of love and it was not too long before she was as skilled in the boudoir as any courtesan.

Gail dropped Jake off at his house that night at eleven fifty-five. He crawled into bed and spooned up to Melissa. He was as tuckered and content as he had ever been.


Jake woke up at seven thirty Sunday morning still pressed against Melissa’s ass and feeling like a million dollars. He jumped out of bed and hit the shower. Two minutes later Melissa joined him. He washed her hair and she washed his. Melissa ordered him out of the shower and started shaving her legs. Jake sat on the toilet seat and watched in fascination. After legs and armpits were dispensed with she started on her coochie. Jake cringed at the rapid flicking strokes she took with the razor, but she looked supremely confident as she deftly spruced up the playground. She finished and stepped out of the shower and into the towel Jake held for her. He dried her off, she opened the medicine cabinet, and handed Jake the baby oil. He applied the soothing oil to her little bald mound before she shooed him out so she could dry her hair. Melissa happily hummed to herself as she dried her hair. Her future husband was taking to domestication nicely.

After church, Jake had Angie drive him to the coach’s place. Angie was atwitter about seeing Tyler next weekend on his three-day break. Maria was bringing him down to tell him in person about the significant changes the family was undergoing.

“I’m happy for you, Princess,” he said.

“I know you are, Jake. I’m kind of sorry that we stopped having all that great sex, but I’m a one man woman.”

“I miss it too but I’ll gladly make the sacrifice for your happiness.”

She kissed him and her eyes were misty, “Thank you, baby brother.”

Jake let himself in and waited for Helga. He did not have to wait long. At precisely twelve-thirty, she rapped on the door and Jake let her in. She glided into the room and turned to Jake as he closed the door. Jake walked over to her and then around her in a circle. Inspection complete, he stood before her again.

“Helga, you are absolutely one of the most beautiful women I have ever seen,” he said with sincerity.

Helga was wearing an above the knee little tropical print frock, tan nylons on her long legs, and three inch blue pumps on her feet. Her hair flowed down her back in gentle waves. It had been brushed until it shone like spun gold. She wore just a little makeup to highlight her china blue eyes. Her lips and fingernails were the same light shade of pink.

“Thank you, Jacob, she said, “Sven helped me get ready. He is as excited about this as I am.”

Jake could see that she was as nervous as she was excited. He sat her on the couch and got them drinks -- Tab for him and a glass of white wine for her. He would have to remember to replace Coach Nelson’s wine stock. She smiled her appreciation for the wine, took a sip, and, twirling the glass by its stem, started talking.

“Jacob, now that I’m here I’m so nervous I feel faint. Sven and I have been married for eighteen years. He proposed to me when he was twenty and I was sixteen. When he graduated from college we got married. We were both virgins on our wedding night. We moved to St. Paul where Sven got an excellent job. He is very talented and rose quickly in the company. He made a good living there and I never had to even think about going to work. We started a family and had the twins right after our second anniversary. I stayed at home and kept house as the kids grew. I was content with my life and so was Sven. But, as the twins became teens, our life seemed to be in a rut. Sven tried to spice up our love life by getting books and movies. They did not do anything for me. Then he started wanting me to flirt with other men. I tried it, but, except for letting his boss grope me at a Christmas party, never could get into it.

“Then we moved here and Erika brought you home. From the first time I saw you I wanted you. I felt guilty about it and told Sven. Far from being mad, he told me just to let myself go. Letting go is not an easy thing for us Norwegians. You made it easier by the way you took charge of me. You just did to me what you wanted and I discovered that I liked it. Sven has always treated me as if I were fine china. I told him how assertively you treated me and how much I liked that, but he said it was not in him to be like that. So here we are, an overweight housewife with nothing to offer and a young stud who can get anyone he wants. It begs the question of just what you are doing this for.”

Jake regarded her for a moment and then answered.

“First off, you are easily one of the sexiest women I’ve ever met. You are not petite but you are not anywhere near fat. I doubt if there is a man out there who wouldn’t instantly want you. Secondly, you are sweet, honest and loving to the point I love just being around you. Lastly, you and I resonate together, the attraction you feel for me matches the urge I have for you. It is Eroto-chemistry 101. I felt it the first time we touched and I think you did too. Now all we have to do is figure out what we are going to do about it. I would never do anything that could hurt you or your family. You all mean too much to me.”

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