Thirty Five Years Late Ch. 03

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Jake returns to Chicago to find an unexpected proposition.
3.6k words
4.5
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Part 3 of the 4 part series

Updated 06/07/2023
Created 04/09/2016
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Leenysman
Leenysman
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"Sir, can you put your seatback into the upright position? We're about to land." The flight attendant was already moving on to chastise the next passenger as I pushed the button on my armrest and reached behind me to pull the seat forward when it didn't move on its own.

I had spent the flight alternating between reading on my tablet and thinking about Jane. My thoughts kept swinging between wild optimism and the kind of pessimism that used to paralyze me when I was a younger man. The rational part of me knew that the real prospects for my relationship with Jane were somewhere in between the two extremes, but I was having trouble keeping the pendulum from swinging. Hopefully, being back in her presence for dinner would stabilize me.

One of my fears revolved around Jane's daughter Amelia. This was the first time I had dated a single mom and I wasn't sure how to get onto Amelia's good side so she wouldn't oppose my relationship with her mom. I had been so bad at dealing with teenaged girls when I was a teenaged boy. Would I be any better now? Was I even prepared to be a stepfather, if it came to that?

After sending Jane a quick text to say I'd landed on time, I put those thoughts aside as I made my way from plane to baggage claim to rental car to hotel, where I checked in, dropped off my suitcase in the room, freshened up quickly, then drove over to Jane's address a few miles away. It was 5:50 when I pulled up to the curb outside a one-story home, painted two shades of brown. The blue SUV in the driveway was the one I'd seen at the restaurant the week before.

I rang the doorbell and heard feet running towards the door. It was yanked open and Amelia looked at me through the screen door, before asking, "No roses?"

"Amelia!" shouted Jane, who was walking towards the door, wiping her hands on an apron, before taking it off, revealing a blue tshirt and jeans. "You're being rude."

Amelia pushed the screen door open and said, "Sorry, Jake. I just thought..."

How to respond to this without making it worse? As I stepped inside, I said, "Finish your sentence."

"I thought it's what men do after they've had sex with someone."

"Ah. I'm sure some men do, especially in the movies, but I didn't have time between landing today and getting here to stop at a florist. Besides, I don't know yet whether your mom even likes roses." I turned towards Jane and she walked into my arms, which I wrapped around her in a long hug, feeling Amelia's eyes on us.

She whispered, "I do, but you don't owe me any," before pulling back to kiss me on the lips. "I like this welcome much better than roses," she said towards Amelia as we broke contact. To me, she said, "Dinner is ready, if you are."

"For sure," I said. "I ate breakfast at the airport at 9, Seattle time, so this will be just my second meal, unless you count peanuts on the plane."

"Wouldn't it be cheaper to eat at home before flying?" Amelia asked, as we walked to their dining room.

"It would, if I weren't traveling for business. Since I get reimbursed for meals once I start my trip, it doesn't cost me anything to eat at the airport, versus eating food I paid for at home. Besides, eating a late breakfast before flying east feels more like an early lunch after the time change. Otherwise, I'd be famished now instead of just hungry."

She thought about that for a few seconds, then asked, "So, when we ate at Jade Thai? Did you get reimbursed for that, too?"

"Only for my share of the check. The rest I mark as personal on the expense report and pay myself."

"So, you don't get to expense tonight?"

"Technically, if I reimbursed your mom and she provided a receipt, the customer would pay me back," I answered. "But, that seems like pushing the system a bit too much."

Jane said, "I don't really like the idea of charging a guest for food, anyway. We'll just call it paying you back for our dinner the other night, since you did pay for our share."

Dinner was a pork roast, with mashed potatoes, gravy and sauteed green beans that were still crunchy, just as I like them. Plus, fresh baked rolls with honey butter. A glass of chardonnay for Jane and me, apple cider for Amelia.

"It's all delicious, Jane. Thank you," I said as I set my fork down. "Can I help with the cleanup?"

"If you're offering," she answered with a smile.

"You say that like it's unusual. My mom taught me better manners."

Amelia said, "Most guys Mom has dated just park themselves in front of the TV while she and I clear the table and put dishes in the sink to wash later."

I said, "Pretty good reason for them to be ex-boyfriends, to my mind."

"Among others," Jane said, not expanding on that.

Most of the pans used for dinner had already been washed before I arrived, so the three of us made quick work of clearing plates and serving dishes, storing the few leftovers in their fridge and getting everything washed or into the dishwasher, which was still only half-full.

"I've got to put some more work into that term paper that's due on Friday, Mom," Amelia said, before stepping towards me. Leaning towards my left ear, she whispered, "You make Mom smile, Jake. Keep it that way, okay?" before kissing me on the cheek and dashing down a hallway I assumed led to her bedroom.

Jane was shaking her head in amusement. She waited until Amelia was out of earshot and said, "She think she needs to protect me."

"Have you needed protection, in the past?" I asked, as we moved to her couch and sat down, Jane snuggling against my arm until I lifted it and put it behind her neck.

"Not physically, if that's what you're thinking. But I probably made a mistake over the years in sharing too much of my heartache with her, when things didn't go well with men I dated. It's made her hesitant to start dating guys. Not from shyness, like you, but she thinks guys will hurt her."

"Well, that's still a pessimistic expectation, Jane. That's basically what my shyness was, except it covered a much broader range of personal interactions than just dating for me, through my childhood, teen years and early adulthood. Being afraid of being rejected turned into expecting it and then avoiding the risk by keeping to myself. The longer I did that, the harder it became to be social outside of work interactions, particularly with women."

"But you overcame it?" she asked.

"It wasn't easy, but yeah. In my early 30s, I realized that burying myself in work wasn't enough. When my first attempts at dating failed miserably, I determined that the pessimistic expectations that I thought were protecting me from disappointment were actually harming me instead. I was subconsciously wanting the negative expectations to come true and sabotaging myself to make that happen."

"Sabotage how?"

"Stuff like negativity in how I asked. 'You wouldn't want to go out with me, would you?' That almost guaranteed that she'd agree that she wouldn't. Instead, I had to learn that being positive and stating my desire in a way that couldn't be refuted was better, like, 'I like you and would love to take you to dinner some night. Are you free on Friday?' That way, I've paid her a compliment and made my desire clear, without presuming to know what her answer will be, one way or the other. But the most important thing I had to learn was that unless a woman went out of her way to hurt my feelings in rejecting me, I was doing more damage to my self-confidence by believing I would fail than she would by saying no. That and understanding that the odds of that mean response were a lot lower than I feared."

"So, how do I turn that into advice for Amelia? I mean, things have changed since we grew up, but she's still more likely to be asked out than to be the one who asks."

I thought and answered, "The risk shifts from asking to saying yes, but it's still that feeling of risk. She needs to be aware of her expectations and either keep them realistic or keep them from getting in her way. You know the Tennyson quote, 'tis better to have loved and lost than never to have loved at all? It encapsulates the idea that even if you take the risk and lose, choosing to be lonely is worse. Avoiding that risk might feel like safety for a while, but our hearts eventually need more than that. So, you might try to get her to see that while there is a good chance that she will get hurt from time to time, it's not a 100% probability and it's survivable, while risk avoidance guarantees a zero chance of success."

"Makes sense," Jane said. "Do you feel risk with me?"

I looked into her eyes and answered, "I don't. Not like I did when we were teenagers. Are you still the girl who tried to trick me at prom?"

"I like to think I've matured since then, in no small part due to feeling ashamed of what we tried to do to you."

"And Kimmy?" I asked. "She was in on that plot, I assume, since she got me to ask you out. Plus, she apologized for it the other day. What can I expect from her when she visits?"

"She's not out to hurt you." Jane paused, before adding, "She's more likely to want to have sex with you, with or without me there, although she hasn't come right out and said so."

I gulped, before sputtering, "What?"

Jane patted her hand on my chest, then said, "I wasn't sure whether to tell you ahead of time or let it be a surprise. I hope it doesn't freak you out, but she and I have been lovers from time to time, both separately and in threesomes with her husband Kurt whenever they visited. They have an open marriage. I thought at first that it was just an excuse for him running around on her, but as I got to know him better, he's sincere in letting her pursue lovers of her own, although she mostly lets him set up spouse swaps and threesomes with other women. You should also know that he's Amelia's biological father, at my request. I told Amelia when she was 12, in case that was your next question. She still calls him Uncle Kurt, though."

I found my voice again. "Let's go back to the 'want to have sex with you' part. What makes you think Kimmy wants to have a threesome with you and me?"

Jane smirked. "Let's just say that my boyfriends seem to be the only men she pursues on her own and only when she comes here without Kurt. A couple of boyfriends broke up with me upon finding out that I'm bisexual, but that's their fault, not hers. Anyway, I called her on Wednesday about what happened between the two of us, then this business trip suddenly popped up the very next day? I don't buy it as a coincidence for a moment. She specifically asked which weeks you were going to be here. If she had wanted to avoid you, she could have come the week you were going to stay in Seattle. No, she's definitely coming that week because you're going to be here. Have you ever?"

I sighed. "A threesome? No. My wife would have been too possessive to share me and I felt it was enough of an accomplishment for me to have a relationship with one woman, given my past struggles, so I never even mentioned it as a fantasy. Threesomes were just something I read about. How did it get started with the three of you?"

"After I broke up with Mike, I moved in with Kimmy and we became lovers for about six months, keeping it secret, given that public opinion towards homosexuals wasn't as favorable in the 80s as today. Just as she got transferred to Syracuse, I got a job offer in Chicago and took it, rather than try to follow her to Syracuse. I went back to dating men and she met Kurt. We had our first threesome the first time I visited them and many times since. Does the idea scare you? I can wave her off if you don't want to. You wouldn't be the first boyfriend to turn her down."

"I don't think I've ever considered it likely enough to have any reaction. Does jealousy ever come into it?"

"It can, but it's usually balanced out by compersion."

"What's con-per-sion?" I asked, not recognizing the word.

Jane said, "Compersion, with an 'm'. It's a word coined in polyamory circles as an opposite to jealousy, meaning a feeling of joy when someone else is experiencing joy, especially sexual pleasure with someone other than you. You might want to read up on polyamory, no matter what happens, because compersion can still apply to monogamy, to jealousy and possessiveness."

"So, you just don't feel jealousy?"

"I did, at first. I still thought of Kimmy as my girlfriend and felt jealous watching Kurt touch her and her touch him. But he talked to me about compersion and it helped me want to add to their pleasure rather than stifle it. Now, I don't feel jealous of the two of them at all. But I also don't have any claim to either of them as being my boyfriend or girlfriend, either. So, I might still feel some jealousy about her being with you, but compersion is still the goal. I can promise I'm not going to leave you for her, if you can make me the same promise if she's just here to pursue you separately."

"You seem to think that's less likely?" I wondered.

Jane replied, "I think a threesome would be her preference and mine as well, but she would settle for one-on-one with you if she had to. I really doubt she's planning to be celibate, even if it means finding a swing club to visit."

"I need to think it through," I deferred.

"I thought you might, which is why I brought it up now instead of letting it be a surprise." She paused for a couple seconds, before saying, "Talking about the prospect has me feeling pretty horny, though. Let's go to my bedroom before it gets too late. I promise you Amelia won't hear anything. Her room's at the other end of the house and the last owners soundproofed the hell out of the master. So long as we're not screaming at the top of our lungs, she won't hear a thing."

The walls of Jane's bedroom were painted a light pink, with lavender on the ceiling and a wallpaper border separating the two colors. The lavender and pink were then reflected in her bedding on a king sleigh-framed bed and other accents through the room. Jane locked the door behind us.

"You like a big bed?" I asked, as I kicked off my shoes and started to undress.

"I don't always sleep in it alone, silly," she replied, starting to disrobe as well. "Particularly when Kurt and Kimmy are visiting, the extra space comes in handy."

"Right. I hope I can spend the night here sometime soon. But the hotel is closer to my work site. And since the customer's paying for it, I ought to sleep there."

"That's okay. Why don't you plan to stay here instead of the hotel for the weekend that you're staying in Chicago, starting with Thursday night? Maybe telecommute from here on Friday as if you'd gone back to Seattle, even do your laundry? Then check back into the hotel on Sunday before another week of work."

"I could," I responded. "But what about Kimmy, if she's not actually looking for a threesome? It doesn't look like you've got a guest room."

"Amelia's already got plans for a camping trip with a friend's family for that weekend, so Kimmy could sleep in her room, if she's not sleeping with us."

Jane had finished getting naked. She put her hands on the footboard to her bed and bent at the waist, sticking her butt out and exposing the cleft between her legs. "Come and get it, stud."

I wasn't fully hard at that moment, so dropped to my knees on the light-grey rug that was there and pressed my face between her asscheeks and licked at her labia from below. My mind briefly noted that her flavor seemed slightly sweeter than the week before. I kept one hand between my legs, stroking my cock to a full erection as her pussy got wetter.

"Right there, Jake!" she cried out as my tongue made contact with her clitoral hood, the pea-sized nub just beginning to make its appearance. I swished my tongue left and right over the skin protecting it and was rewarded by more low moans from Jane.

I stood quickly and used the glans of my now-steely shaft to resume pressing against Jane's clit, rubbing it in circles four times, then slipped back, notched my cock into place and thrust forward. "Fuck!" slipped from my mouth as my shaft slid into her until I slapped my pelvis into her ass. Remembering that she liked it hard, I grabbed her hips and pulled her back to me with each stroke until she started pushing back into me herself, making the bed move slightly as she pushed away from it.

I smiled at the thought that we were rocking the massive bed without even being in it. I had a brief flash of jealousy thinking that maybe she had done the same thing with someone else, perhaps Kurt, then remembered what she had said about compersion and let it go. I realized in that moment that I didn't own her past, I simply wanted to be part of her future, even if it meant sharing her with others.

I reached my left hand further around her hip until I could reach her clit, stroking against it as I pulled her back into me. "Jaaaaakkee!" she cried out as her first orgasm hit her, making her legs wobble a bit. I maintained my hold on her to prevent both of us from falling and kept slamming into her as she crested, then regained her footing. "Let's get in bed," she panted, sliding off of me and moving around the left side to pull the covers down.

I went to the right and pulled the other side of the covers down, then we met in the middle again. Jane said, "I want to ride you," and I lay down on my back, with my head propped up by her pillows. She grabbed onto the headboard above me, before throwing her right leg over my hips.

I reached down and guided my cock back into her as she lowered herself, keeping eye contact with me. She then used a combination of her arms and legs to rock forward and back, pumping me into her with force and speed that had us both grunting as our torsos impacted each other's. I definitely knew she'd done this before with someone. This time I was glad for it, though, as I got to be the beneficiary of that experience.

"God, Jane, that's so good," I said, softly, beginning to pivot my hips to add more force to our fucking. I reached my hands up and grabbed onto both of her breasts, squeezing them and tweaking her nipples lightly.

"You can... pinch them... harder," Jane murmured between thrusts.

I did and her moans picked up in intensity. Suddenly, she was shaking in another orgasm, crying out, "Jake!!" loudly enough that I doubted any soundproofing was good enough to block it out. I thrust up into her harder, feeling my own orgasm approaching but not quite ready to explode.

She let go with her arms and collapsed onto my torso. I kept thrusting my cock into her, wrapping my arms around her. As she came down from that orgasm, she kissed me, biting on my lower lip before her tongue started to tangle with mine.

"Almost there," I muttered, when our lips parted again.

"Give it to me," she responded, "Fill me up!" She leaned to the left and took my earlobe between her teeth, just as my cock started to burst my load of cum into her depths. A couple more thrusts as my shaft jerked and spurted and I was drained, gasping for breath.

Jane returned to kissing me, softer and less insistent now, as my cock gradually softened and plopped out of her. A mental image of Kimmy going down on her to pursue my sperm popped into my mind and I found myself looking forward to see it happen in real life.

I wasn't ready to tell Jane that I was a yes so quickly, but I had already made up my mind. If a threesome is what Kimmy wanted, so did I.

~~~~~

Author's Note: Chapter 4 will appear in the Group Sex category.

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6 Comments
AnonymousAnonymousabout 1 year ago

My rating would have been higher except for the talk about sharing.

I can’t ever condone that. I just looked & im repeating myself from a year ago. 😜

Bill S.

Rancher46Rancher46about 2 years ago

So far, I like the series, it is well written with a slow evolving but interesting storyline. Gets my 5++star vote!

AnonymousAnonymousover 2 years ago

Interesting & a nice read, but I don’t care for the sharing that seems to be in the future.

Bill S.

goducks111goducks111over 4 years ago
Thanks for the update

I think you know i really enjoy reading your stories. Well-written with interesting plots and good characters. I'll be looking forward to seeing more of this story. Hopefully soon (i know - i need patience), but if i need to wait......

and Thanks for publishing your works for us to enjoy!

LeenysmanLeenysmanover 4 years agoAuthor
@goducks111

Let me address the length first. It made sense story-wise to break the chapter where I did, which happens to make Chapter 3 be 75% of the length of Chapter 2. The next scene jumps another three days, so starts Chapter 4.

As for the delay between Chapters 2 & 3, I do apologize for that. Keep in mind though, that this did not start out as a series - the unnumbered first segment was written as a standalone short story in April 2016, a month after my very first story, and I didn't decide to extend it until almost a year and a half had passed. I then got writer's block when it came to story direction after releasing Chapter 2 to Lit and then worked on several other things in the meantime, including stuff not posted here. However, I didn't expect it would take nearly a year to get Chapter 3 out and I'm sorry for that. If I had known it in advance, I wouldn't have released Chapter 2 at all and let the short continue standing on its own.

The good news is that the remaining story has been outlined and about 2000 words already written, part of which is my expected ending. I no longer feel blocked but will probably finish the story before deciding how to break it into chapters, then release them here over a period of time as well as releasing in ebook form. I won't make any promises about a release schedule, though.

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