Double Take - Cover

Double Take

Copyright© 2019 by aroslav

Chapter 40

Coming of Age Sex Story: Chapter 40 - 1st place 2019 Clitorides Award for Best Erotic Do-Over! Life was good; just not long enough. At 80 years old, Jacob is dying and wants to go back to his youth. He has no burning desire to change the world. He just isn't ready to die. And someone has decided that's okay. But he's in for a major surprise. His new life is in an alternate reality. Things just aren't what he remembered. ©2019 Elder Road Books

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   mt/Fa   Teenagers   Consensual   Lesbian   Heterosexual   TransGender   School   DoOver   Incest   Brother   Sister   Polygamy/Polyamory   First   Masturbation   Oral Sex   Tit-Fucking  

“The sacredness is there. In the truth, the pain, the beauty. So that the telling of it is sacred.”
―Ursula K. Le Guin, The Telling


“HMM. MAYBE I SHOULD GO to prom, too,” my sister said when I told her about what Joan and I were doing and that I needed to figure out a transportation solution. I was hoping she’d volunteer to chauffeur us but never thought about her planning to go to prom, too. Dummy!

“You mean you don’t already have a date and everything set up?” I exclaimed. “I mean ... You’re a senior. Isn’t this like the most important event of the year?”

“Um ... There’s so much during senior year,” she said. “I had to take that NSO exam in December and see what I’m qualified for. And now there’s SATs in two weeks. Seems silly to be taking it now when I’ll have to take it again in two years when I get out of Service. But they say that good scores on the SAT will help determine whether I’m eligible for a management track in any of my service options. And then there’s graduation coming up two weeks after the test. I guess I just let prom slip by.”

“And none of the guys you’ve been dating have offered to take you?”

“They all have dates for prom already. My first choice for a date already has one.”

“Who?”

“You, dummy. Hmm. There’s this nice but kind of geeky boy I’ve been flirting with, though. I bet he doesn’t have a date yet. I’ll ask him.”

“Oh. Well, good luck.”

“Hey. How about if we double to the prom. I’ll pay for a pre-prom limo to pick us all up and then you can pay for one to take us home. You can drop us off first and have him drive around for a while so you can make out with Joan in the back of the limo. From what I’ve heard, there’s a four hour minimum. That should give you plenty of time. I don’t think Brian has much money, so we’ll keep everything else simple.”

“What will you wear?” I asked. Okay, I was pretty tuned in to the way girls talked. I knew for sure that one of the major areas of discussion at lunch on Monday would be what dress Joan had chosen for prom.

“Oh, probably the same little black dress I wore for the Winter Dance and the Valentine’s Dance. I don’t want to go out and spend a lot if I’m paying for part of the limo.”

“Here,” Dad said, sliding his credit card over to me. “Why don’t you take your sister out and get her a prom dress?” We’d finished our Easter dinner and were just sitting around the dining table chatting. “Try to keep it under $300 please. As pretty as that LBD is, you don’t want to wear it for prom, too.”

“Really, Dad?” Em said excitedly. He nodded.

“Can I go, too?” Pey asked. She was almost as excited as Em. “I mean shopping? I don’t have a date for prom yet.”

“That’s kind of up to Em,” I said. “This is for her.”

“Of course you can go!” Em laughed. “I wouldn’t trust J’s judgment on what dress I should get.”

“You should probably go call this young man and make sure you have a date first.”

Em jumped up from the table and ran to her room to make the call.


Shopping with Em and Pey was a lot of fun. I mean, I got to just sit and play on my iPhone and look up each time a beautiful girl who I loved came out to model another dress. We’d gone to Macy’s and I found the same clerk who helped Joan. She looked at me a little strangely until I explained that this was my sister, not a second date. Em said she wanted a short party dress that she’d be able to wear again to other occasions and the saleslady was all over it.

Em eventually chose a very pretty two-piece outfit with a silver skirt decorated with grey and black roses and a form-fitting black top. When she shifted around and raised her hands as if to dance, she exposed a nice band of soft skin where her date’s hand would rest. I was a little envious. And it only cost a little over a hundred dollars. Well within Dad’s budget.

Brian joined us after our excursion and Em led us to Louie’s for a tux rental. He hemmed a bit but Em told him not to worry. She didn’t want him in anything outrageous—just a simple black tux. He looked pretty good in it with his tousled blonde hair. Even with sneakers.

“J,” Em whispered to me. “Pay for the tux with Dad’s card. Please? We’ll still be under two hundred.” I smiled at her and slipped the cashier the card. I don’t think Brian ever knew that it was paid for.


I was right about the lunchroom conversations on Monday but we all had to buckle down on the project. Beca and I spent a little time each day after school going over the PowerPoint. Rachel had the paper edited and formatted according to Mr. Richards’ stylesheet.

Rachel and I only had one opportunity to get together during the week and it was a little rushed and unsatisfying Thursday afternoon. I really wanted to be with her more and she did, too, but there just wasn’t any time we could be at one of our houses without being interrupted. Em picked up Pey from school Thursday and took her to the mall to pick out earrings so Rachel and I could have a little time in my bedroom.

“Don’t forget me, J. Please?” Rachel said as we lay together after we’d made it to an orgasm. This was becoming my favorite part of making love to her, even though I had to keep one eye on the clock so we were dressed and studying by five o’clock.

“Rachel, you are the girl for me. Do you want me to cool it with Joan? I don’t want to let anything damage what we have,” I said. It was weird enough to be dating—I mean really dating and getting sexual—two girls. Both of them knowing it and encouraging me with the other was more than my V1 head could comprehend. In that timeline, being with two girls meant you were cheating on one or both of them.

“I get a little jealous knowing that you are with Joan on Saturday night, I admit,” she said. “This is kind of the test, though, J. Are we really going to be together? I mean all of us? I think Beca, Desi, and I are mostly upset that we don’t get to buy pretty clothes and go out that night more than we’re jealous of you and Joan. I just love you so much that I want to be there, too.”

“Why don’t the three of you plan something special?” I said. “Here’s an idea. The limo is going to pick us up at six to go out to dinner. Then the prom starts at eight. We have the limo for four hours. Why don’t we send it to pick the three of you up to go to dinner after it’s dropped Em, Brian, Joan, and me off at the prom? Then you can have him take you to one of your houses for a private dance.”

“That’s such a good idea, J. You’d do that for us?”

“You’re my girlfriends and I love you,” I said.


Friday after school, Francie came over. No, we didn’t screw or anything. Em was taking her out for her eighteenth birthday. But she had little William Jay with her and I got to hold the baby for a while before Rachel picked me up for our Friday night date.

“Gosh. I don’t have a present for you, Francie,” I sighed as I handed the baby off to Em. “Maybe I could give you your first ever eighteen-year-old kiss.” I didn’t give her an opportunity to respond. I just pulled her to me and felt her melt as we got our tongues tangled.

“You’ve been waiting for six months to get me back for that, haven’t you?” Francie giggled. “Man. I need to get in shape and get back in the game. I forgot what I was missing!”

Rachel picked me up at six for our date and we did the unheard of. We drove way out in the country and found a place to park. In the back seat of her Yaris, we made love for four hours.


We all got together Saturday afternoon to go over the final paper and presentation, with Beca and me rehearsing the presentation in front of our three girlfriends. We were finally satisfied with all the pieces. We printed the paper on Joan’s printer after we’d made a few edits and locked up the presentation. We were as ready as we’d ever be. We’d turn in the project Monday morning and Mr. Richards told us that the order in which projects arrived on his desk would be the order of presentations. Most people in the class would wait until the last minute to turn them in, so it was likely that Beca and I would be the first to present on Wednesday. We didn’t mind. We were ready and decided to practice a couple more times before the presentation.


Joan and I were a little less frantic about getting things ready for prom. Our date was laid back and I found out more about her. Her parents had been divorced for five years and her mother had been well provided for. Her parents met in college and married. But they signed a prenuptial agreement. It clearly stated that her mother would work to put her father through school and that she would be entitled to half of whatever he earned and they acquired. Indiana not being a community property state, the agreement settled the terms of what could have been a messy divorce. It fixed the terms of property division, continued support, and child support. When her father became president of a large financial conglomerate in Chicago, her mother declined to move with him. Joan was twelve. The terms of the settlement had provided the existing level of support for Sharon for the same number of years they had been married, so she was set for twenty years from the date of their divorce. Joan would continue to get direct support until she was twenty-one and a trust fund that would mature and be fully in her control when she turned twenty-five.

“Do you miss your father?” I asked as I held her hand across the restaurant table.

“Yeah. Sometimes. I go to Chicago for the summer. It’s fun. My stepmom is a little resentful, but we called a truce when Dad threatened to throw us both out. I’ll take some classes at the College of Graphic Arts this summer. And in Chicago, I don’t have to compete with my mother.”

“Is she really that much of a cougar?”

“Yeah. But it didn’t affect me until I started dating. Then it was like she wanted to impress my dates, even if they only rolled by to pick me up. She said it would help my cause if the guys I dated saw that I have the genes for a long-term body and would look as good in twenty years as I do now,” Joan said sadly. “There, now you know what you have to look forward to.”

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