Thirty Five Years Late

The next morning, when the alarm blared, I woke up with an erection pressed into the crevice of Jane's ass. She bolted right out of bed, and changed from nightdown into sweater and jeans. She looked back at me and the tent pole in my shorts and sighed. "I really wish I could stay and take advantage of that morning wood, but Amelia needs to get to school, then I have to hurry back home to get ready for work. I'm not going to have time to get together tonight, then you fly home Thursday. When do you return on Sunday?"

I grabbed my cell phone to look up the itinerary in my reservation tracker app and told her, "My flight lands at 4:15, if it's on time."

"Would you like to have dinner at my place?" she asked. "Say, sixish?"

"I would love it," I responded. "I eat alone too much, either in restaurants or at home."

"I'll text you the address."

I got up and gave her a quick kiss when she finished putting her shoes on, then she was out the door. I was still hard as a rock, so climbed back in bed and jerked off to the memory of the night before.

After my orgasm, I showered and, when I was dressed, checked my phone. I had a text from her, "Miss you and your cock already."

I replied, "It's going to be hard all weekend, missing you."

Her answer was, "Mmmmmm, I like that mental image!" and a tongue-sticking-out smiley.

~~~~~

In a spare moment that morning, I emailed Lucas, my boss, to see if the offer to pay relocation expenses was still in effect. After confirming it was still available with a link to the policy, he tacked on the question, "So, who is she?"

I shot back, "How do you know it's because of a woman?"

He replied, "I've only ever had three other employees ask to relocate after passing up the assistance when they were hired. In all three cases, it was because they met someone in one of those eligible cities. So, spill it."

I answered, "She's a woman from high school. We reconnected with a few months ago. She lives near Chicago now, so we met for dinner and sparks flew. The relationship is very young, but I really only need a small nudge to leave Seattle after my divorce. Even if things don't work out with her, I think the change of scenery will be good for me. The prospect of shorter flights and the financial assistance each week simply makes the decision easier."

His last email said, "Good for you. Let me know when you've found a place in Chicago, when you think the move can happen, so we can avoid putting you on a new assignment. If you can get packed up on your weekends before this assignment ends, so the moving truck transits during your last week, you would only need one week off to get unpacked, rather than taking a week off to pack and another to unpack. It's your vacation time, though, I just need to know how much of it you'll be taking."

~~~~~

I messaged Jane, "I checked with my boss and the relocation assistance is still available. Would like your advice on the best places to rent near you."

Her response was, "Of course. I'll get a list of places put together so you can start checking them out next week. Thank you for not asking to move in with me right away." She also included her home address.

I replied, "Finding an apartment is the obvious first step. I am curious why you think I would ask so soon. Last night was certainly a fantastic beginning, but it is still only a beginning for us. We need to spend a lot more time together before we reach that point. That includes time for Amelia to get used to my being around, since I'm sure her acceptance would influence your decision. I'll be here four of the next five weeks, with one week telecommuting, but I doubt that would be enough time, either. Besides, having my own place lets us have the privacy to keep our sex life away from Amelia's eyes and ears. I assume she knew we were together last night?"

Jane sent, "On the first point, a guy I was dating about five years ago thought he could ask to move in after just two dates. He got mad when I said no and we never had a third date. It turned out he had just gotten evicted for not paying his rent because of a gambling problem, so I really dodged a bullet there. As for Amelia, she knew where I was, all right. She called me out on it during the drive to school this morning, accusing me of having a double standard, because I've always told her she should know a guy is trustworthy before even thinking about sex with him. And here I am, going to the hotel room of a man I haven't seen in thirty five years and have only talked with online for a few months. My defensive reaction was to remind her I'm an adult and she's not and I don't have to worry about pregnancy and having some guy desert me and a baby, like I worry about happening to her. It shut her up for the moment, but I expect she'll have a counter-argument by dinner time. I'll have a few more discussions with her about my motives for sleeping with you before you come for dinner. I don't want her starting off on the wrong foot by accusing you of corrupting me or some other nonsense."

I sent back, "Should I know about these motives? And I guess I shouldn't point out she was the one who told us to get a room in the first place?"

It was after noon when Jane answered, "God, I've rewritten this reply six times, trying to find the right words. My motives? Because I'm attracted to you and was feeling horny and flirty and all that. Because I didn't want to say some 'old classmate' goodbye at the door of the restaurant and risk never seeing you again. Because I wanted to replace all those 'what if' questions I've had about you since high school with some real memories, whether better or worse than the fantasies (the real you is better, by the way). Even being with you just once would have been better than never at all. Plus, I figured I could finally let go of my guilt for planning to trick you at the prom. As for reminding Amelia of 'get a room', I would rather you didn't. First, she was actually being extremely rude in making that suggestion to a pair of adults, even though we ultimately agreed with it. Second, I don't want to imply, even in jest, that she made our decision for us or that she has the power to make any other decisions for me, pro or con, including any future decision on you moving in. Her saying that and you flipping the key card onto the table created the opportunity for me to get what I wanted. But that decision was already made and was mine to make, not hers. If she hadn't said it, I would have still found some other way to wind up in your bed at least once before your assignment here was over. I don't regret it was last night, even if the speed of it seems contradictory to Amelia."

I responded, "You aren't going to hear regrets or complaints from me. Last night surpassed my expectations from the moment I saw you. Regarding guilt, we both made mistakes as teens, but we aren't those people any more. They might have begun the broken road that got us to where we are now, but I would rather look forward to where that road leads than backwards. Who I am today wants to pursue what began last night, without that baggage from the past dragging us down. I never really got to know the Jane from 35 years ago because I wasn't ready to take the risk. I definitely want to know who you are now."

About an hour later, I got a message from Kimmy Cartwright, "So, Jane tells me the two of you had dinner (and hinted at more?) and she confessed about the plot to embarrass you at prom and you forgave her. I finally have the chance to apologize for my part, in getting you to ask her. I'm sorry, Jake. It was immature and mean. I have to come to Chicago on business in three weeks myself and always visit Jane whenever I'm there. I hope the three of us can get together and I can repeat that apology face to face."

I answered, "Apology accepted. The strange part is I convinced myself I was being tricked with no real evidence, which was why I canceled the date. Even though I don't know whether that was a premonition or just my self doubts talking, I forgave you a long time ago, for what I thought you might have done. Otherwise, I wouldn't have friended either of you. That makes it easy to forgive you again, now that I know there was a real plot. I'm in Chicago that week, Sunday to Thursday. If that coincides with your trip, I'll see you then."

~~~~~

Except for dropping Jane a quick "landed at SEA safe and sound" text from the airport, I didn't talk to her again until Friday night, when she called me just after I finished my day's work.

"Hi, Jane, how are you?" I asked.

"Missing your voice already," she answered. "What are you up to, tonight?"

"About to repack my suitcase, then start laundry," I answered.

"That seems out of order, somehow," she said. I imagined her scrunching her forehead as she said it.

I answered, "The only way laundry takes priority is if I'm out of clean clothes to pack, which I'm not. Otherwise, repacking comes before laundry. I can fly with dirty clothes in the hamper, but not with an empty suitcase, y'know?"

"That makes sense, looking at it that way. Is Friday night when you do it, instead of Saturday?"

"Usually, unless I've arranged a date for Friday. After my telecommute is the first opportunity to do it after I get home. I can relax once it's checked off, rather than wait until Saturday night to do it or in a rush on Sunday morning."

"Are these things your wife did for you?" Jane asked.

I hated discussing Connie with women I was dating, so tried to keep that out of my voice.

I answered, "Well, I didn't have this job when we were married. I'm sure Connie would have argued against my taking it because she could be very possessive of my time and deciding how I spent it. If I'd taken the job anyway, she would have probably done everything possible to avoid making it easier. Refusing to do my laundry or driving me to the airport would have been tactics to express her resentment. Do you really want to talk about her or are you just checking on whether I would expect you to do the same?"

She hesitated before saying, "I did start to wonder, today, what dating a road warrior is going to be like. Even though you're moving to Chicago, once you're on an assignment to another city, I could actually be seeing less of you than I might during this assignment. You'll be gone four nights and in Chicago for three instead of the other way around."

"That might be true if I flew 52 weeks per year, but it's more like 35 to 40 trips, four nights each trip. That works out to no more than 160 hotel nights, which isn't even 50% of the year. On this assignment, it's five weeks out of six, and week one is already done. I'll have 16 more nights in Chicago on this assignment, out of 35. That's less than 50%."

"But you travel Sunday to Thursday. Isn't that more like five days and four nights, meaning you're gone 20 days out of those 35?"

"Yeah, flying from Seattle, travel eats up most of Sunday and most of Thursday night, but I still sleep in my own bed on Thursday night. In a pinch, I can fly a Sunday night redeye and drag through Monday. Moving to Chicago, my travel time should be sharply reduced, both in terms of distance and getting direct flights instead of connections. For some cities, I might be able to fly on the first flight Monday morning, instead. If I manage that 50% of the time, that cuts my nights away to 140. And I regain most or all of my Sundays."

"But they're still impacted, either by a flight or having to get to bed early."

"Let me ask you, how often do you date on school nights, anyway? Those are when I'll be away."

"Not often," she admitted. "I suppose dating on just Friday and Saturday nights and subsisting on phone calls and chat while you're gone would be no different when we're in the dating stage. But, while I don't think I'm as possessive as your ex sounds, I'm not sure living together only 60% of the time would be satisfactory."

"Jane, the only thing I can do is promise to maximize both the quantity and the quality of the time I get to spend with you, within those constraints. I don't golf or watch football all day Sunday. My telecommute day is just eight hours because my time is billed by the hour and customers don't want to pay for overtime, even though I'm paid salary, where most other salary jobs would want at least 50 or even 60 hours of work per week. I won't arrive home late or grumpy from traffic on those nights, although I can't promise to never be delayed on Thursday nights. Being home before you, I can easily cook dinner. I like cooking, I just don't like eating alone. It will be my goal to give you so much attention that you'll get tired of me by the time I fly again."

"That would be different," she said, chuckling.

We talked for a while longer about the pros and cons of my job, from fringe benefits associated with my travel to arrangements to travel from customer sites to Maine to visit my parents in place of traveling home to Seattle for a weekend, details that aren't directly relevant to this story or very interesting in either telling or reading.

At one point she asked, "So, would it be possible to fly me to the city where you're working instead of you flying home, so we could sightsee there together for the weekend?"

I answered, "I know some of the married consultants have done just that. The catch is the customer can't reimburse your travel, only mine. It's an ethics violation, otherwise So, I would use my airline miles for your ticket. Instead, the customer would reimburse for the extra hotel nights, up to the value of the airfare that I would otherwise charge them. And I still have to work Friday's hours, which I'm sure they would want to be at their offices, rather than telecommuting from the hotel."

"I'd probably fly in on a Friday evening, anyway," she said. "To avoid using a full vacation day."

"Then, I hope I get some consecutive weeks in cities that you want to visit. As I mentioned, I'm only traveling four of the next five weeks. Week 5 is the telecommute week. I'm thinking of staying in Chicago for the weekend between weeks 3 and 4, just in case I haven't found an apartment by then."

"You don't need that weekend to pack?" Before I could answer, she asked, "Hold on, that's two more weekends from now? Kimmy Cartwright is actually coming to visit me that weekend before some meetings she has the following week, if you don't mind having a third wheel on our dates or just hanging out at my house with us."

I said, "I don't mind. It was her friend request that led me to reconnect with you, after all. She actually messaged me on Wednesday with her own apology for the prom plot and mentioned that she was coming to Chicago in 3 weeks. I guess it's down to 2 now. So, now that we've mainly talked about me and my job, what are you up to tonight?"

Jane replied, "Amelia's at a movie with some friends, so I'm home alone and not sure whether I'm feeling lonely or horny. I figured calling you could address both, if you were interested in a little phone sex."

"I've never actually done that," I said. "None of my previous girlfriends or my wife expressed any interest."

"You masturbate, at least?"

"Yeah, of course. A lot, in the years before I overcame my shyness, hardly at all during my marriage. Now that I'm single again, I'm back to doing it before sleeping. Being with you was the first intercourse I've had since Connie and I separated before the divorce. None of my dates since then have gone past first dates."

.

"And talking dirty?" Jane asked. "I noticed you didn't do much the other night. Phone sex is mostly just talking dirty, mixed in with some grunting and groaning, while we both masturbate."

I said, "My instinct is to be silent while masturbating, starting in my teen years and continuing into college. Even when I lived alone, I didn't break the habit. I can try being more vocal, so long as you'll accept that it's not natural for me and I'm probably going to be lousy at it."

"There's no way to do it wrong, hon. We can describe what we're doing to ourselves in the moment, but it can be more fun to imagine that we're together and what we might do to each other and turn each other on that way. Are you willing to try now, or do you want to get your packing out of the way first?"

"Oh, packing can wait. I just need to get undressed, in bed and put the phone on speaker."

Jane chuckled, "Not going to one-hand it?"

"I normally use both hands with some lube. Getting that smeared on the phone isn't a good idea. How do you do it?" I asked.

"I find if I use the phone's microphone and speaker, the buzz of my vibrator gets picked up too easily. So, I use the same hands-free earpiece I use for my commute."

"You do phone sex a lot?"

She answered, "Just with this one man. About four years ago, I was taking a break from dating and went into an adult chat site. I met a guy who called himself Joe. We chatted a few times, it turned into sexual role playing in their private rooms and finally we exchanged anonymous IDs for a voice-only chat app and used that for phone sex about a dozen times before his wife put an end to it. My handle on the site was DeliciousRose, so he called me Dee."

"He was married?" I asked.

Jane replied, "Yeah, he admitted that from the very start, said his wife was frigid and she didn't consider chat to be cheating because he wasn't physically involved. I had no way to confirm that and figured I didn't need to. But, based on his wife's screaming when she walked in on him the last time, any permission he had for chat didn't extend to phone sex. The next day, his accounts were both gone. I never heard from him again. I deleted the app and stopped using the chat site. I got more active on Facebook after that."

"So, you've got more experience with phone sex than me, but he was the only one?"

"Yes. All of my previous relationships were local, either dating or living together before breaking up. You're actually my first long distance relationship, even part-time. Unless you count Joe, which I don't. But if you'd rather just wait until Sunday to see me, we don't have to engage in phone sex at all. I think I mostly needed to hear your voice tonight."

"Now, you've piqued my curiosity, Jane," I said. "If we don't do it tonight, I'm just going to imagine I'm hearing you while I jack off. I'm willing to bet you will, too. So we might as well do it for real."

"None of it's real, Jake," she chortled. "We're using words to pretend either that we see each other masturbating or we are touching one another. It's about imagination."

"Our voices and the minds behind the words are still real," I said. "We can either hear each other talk dirty or imagine that, too. Don't they say that the brain is the most powerful sex organ? We'd be exciting each other's minds, letting that drive our arousal."

"I hadn't thought about it that way, but I guess you're right. Are you in bed, yet?"

"Just got upstairs. Let me switch to speaker and get naked."

"Let me describe taking your clothes off and you copy most of what I'm saying," she said, after I clicked over to speaker. The tone of her voice changed as she said, "I step up to you and run my hands over your chest, flicking my thumbnails across your nipples. I work my way down to your abdomen and clench the bottom of your tshirt and pull it free from your jeans. My hands slide beneath, pushing your shirt towards your chest."

"I raise my arms, so you can push my shirt over my head," I said.

"Good, good," she said. "I push your tshirt over your head, but leave it tangled on your shoulders and behind your neck. Take it off in real life, but pretend it's still there keeping your arms in the air in the fantasy. I kiss my way down your chest, giving each nipple a little bite, before I drop onto my knees and start opening your belt."