Jackie's Mom

The Usual Disclaimer: This is a work of fantasy. All characters featured in sexual situations are over 18. The characters in these stories are fictional. Any resemblance to actual persons living, dead or undead is purely coincidental. Do not try this at home.

*****

Jackie was a girl I dated when I was in high school. She was only the second girl with whom I had sex. We dated for a couple of months and then broke up. We wound up running into each other again over spring break a couple of years later, and wound up having a night of really hot, sweaty sex in a hotel room. I had been with a handful of women between the time we broke up and that second encounter.

As Jackie lay back on the bed, gasping in the aftermath of an intense orgasm, she told me, "If you had been this good in bed back in high school, I never would have let you go!"

I smiled and kissed her on her neck. Then I rolled back on top of her and drove my cock back into her drenched pussy. I put her ankles up onto my shoulders—something we had never done before—and really pounded her deep and hard. Jackie had very impressive breasts, and they shook all over the place. The wild look in her eyes was priceless. When I think about the way she looked at that moment, I can still picture it clearly.

It still makes me hard when I close my eyes and think about it, years later.

We wore each other out, showered together, and fell asleep with her head on my shoulder and my arms wrapped around her. The next morning, her blonde hair was disheveled when I awoke to see it bouncing up and down over my crotch. I took her doggy style on the bed, and spanked her bottom—again, something we had never done before. Jackie really got off on it, and then she shocked me.

"Oh, God!" she gasped, looking over her shoulder at me, "Pull your dick out of my pussy and shove it in my ass!"

I had never fucked a girl in her ass before. I had seen some anal sex in pornos, but of course that isn't the same at all. Her asshole was not lubricated, and even though her pussy had drenched my cock in her juices, it hurt her badly when I jammed my hard cock into her tight sphincter. The weird thing was, she really got off on the pain. It was so fucking tight, though, that I couldn't even move in there. She shivered and screamed.

"OH, FUCK! CUMMING!" she howled.

We showered again after that. Her ass was really sore, and she walked funny as we made our way out of the hotel. I never saw Jackie again.

The next woman I had sex with did not take kindly at all to me shoving my cock into her unlubricated asshole. She did, in fact, kick me in the balls. Hard. Looking back on that now, I realize I absolutely deserved it.

I did my homework after that. Read a few books that had chapters dedicated to the art of anal sex. Every one of them basically told me I had been an idiot. The next woman who invited me to her backdoor was treated to an extensive visit by my tongue before I even went for the lube. She had one sexy ass, and I thoroughly enjoyed every moment I got to savor it. She had some remarkably intense orgasms with my cock buried in her amazing asshole. It was the first time I had ever had a woman squirt on me during sex.

After that, I was hooked. It's not as though I stopped enjoying a woman's sweet pussy. I still love a good blowjob as much as anything on earth. But a woman's sexy ass became my kryptonite. When it was exposed near me, I would just get weak in the knees.

I joined the Navy after a couple of dead-end jobs, mostly to get away from my hometown. I wound up being stationed on a tin can operating out of San Diego. That's a destroyer for those of you unfamiliar with the term. My boat was a relic of the Second World War, far older than any of the young guys serving on her. We wound up spending far too much time in the Persian Gulf, floating around bodyguarding an aircraft carrier.

Life at sea, on a boat with no women on it, was about as dull and frustrating an existence as you can imagine. Like most guys on my boat, I became a practical joker just to kill time. We would spend hours coming up with new and innovative ways to pull elaborate pranks on our shipmates. I also read hundreds of books and jerked off countless times to the gorgeous women in publications like Penthouse and Swank. We did that for nine months of the year for the remaining three years of my enlistment.

I had signed up for the GI Bill, and looked forward to getting back to the world and attending college. Unfortunately, I had not had the insight to take the SAT exams before I got out of the Navy. I had to take the test and wait for three months for my results. Fortunately for me, my parents were happy to have me staying with them while I did that.

My mom had made the brilliant suggestion that I ought to get a study guide for the test before I took it. That made all the difference in the world. I can only imagine how badly I would have done if I hadn't studied beforehand. I had used math extensively in my job in the Navy, but it wasn't the sort of math questions that were on the test. When I first took the practice test from that study guide and looked at the first math question, my response was, "What the fuck?"

I had to turn to the answer key, look at the answer, and then back to the question just to figure out what they were asking. I did that a couple of times, and then I was back into that groove mentally and did well for the rest of the test. When I took the actual test, I was confident my scores would be good.

Thanks to all that time spent at sea, I had saved several thousand dollars during my enlistment. I bought a used car and reconnected with some old friends that were still in my hometown, as well as some who had left and returned like I had. I also ran into a couple of girls I had dated before I joined the service, and another girl I had known in high school who confessed she had always wanted to date me.

After all the stuff I had seen in my years in the Navy, it felt weird to sneak that girl back to my parents' house to have sex when they were at work. Cynthia was an assistant manager at a fast food restaurant now. She had a gorgeous ass, but alas she wouldn't let me near it. When I turned her over on my parents' bed and started lavishing kisses on her ass cheeks, she flipped over on the bed and looked at me like I was a freak.

"What are you doing?" she asked me.

"Kissing your fantastic ass," I replied.

"Don't do that, it's weird," she said firmly.

I started kissing her pussy then, and she was just fine with that. She was delicious, and I relished her taste. I loved the way she came, bucking into my face, when I buried two fingers in her tight pussy and sucked her clit. She loved the way I filled her up with my hard cock after she finished that first orgasm.

Cynthia and I had some very enjoyable sex over the next few weeks. I would drop by her restaurant a couple times a week while she was at work, just to flirt with her. She particularly enjoyed that after the school year started up. Business was terribly slow during the middle of the day, so we could often visit for an hour straight without interruption. That isn't a euphemism for having sex in her workplace. I would just hang out and talk with her.

On one of those visits, I ran into Jackie's mom.

It had been years since I had seen her, back when Jackie and I had dated in high school. She looked exactly the same as I remembered, and even her outfit looked like one I had seen her wearing before. She had curly, dark red hair. She was about five-foot-five, so I was substantially taller than she was.

"Nathan?" she asked softly from behind me.

I turned and recognized her, but I could not for the life of me remember what her first name was. She had always been 'Jackie's mom' to me. She was also on her second marriage, but Jackie had kept her last name. I could not remember what her new married name was. I smiled at her, trying like hell to remember her name.

"Hey!" I said, "I haven't seen you in years. How are you?"

I offered my hand and she shook it.

"Do you remember who I am?" she asked. She seemed a little surprised that I did.

"Of course," I said, "How could I forget you? How is Jackie? I haven't seen her in years, either."

"She's alright. She and Rob broke up a while back. Jackie joined the Army two years ago."

I vaguely remembered Rob. I was surprised that Jackie had joined the Army. I just couldn't picture it. I did finally remember that her second husband's name was Tom.

"How's Tom doing these days?" I asked.

I had felt a little surge of triumph for even remembering that name. That was short-lived when I saw her face fall.

"I don't know," she said softly, "We got divorced years ago."

"Oh," I said, "Sorry about that, I had no idea."

She shrugged. I recalled then that Jackie had younger siblings. I think she had a brother and sister, but really couldn't remember. I was almost afraid to ask, but did anyway.

"How are your other kids doing?"

"Sally graduated high school this past spring. She just started college two weeks ago. Brent is in his sophomore year of high school."

I was a little shocked by that. I recalled them being really small kids when Jackie and I had dated.

"Wow," I said, "time flies. I remember them being so young the last time I saw them." I held out my hand indicating waist height. They had been that short.

I noticed that Cynthia was giving me a hard look from behind the counter. I walked up to her and grinned.

"Hey, Cynthia," I said.

"Hey yourself," she replied, looking a little grumpy.

"Do you remember Jackie, from high school? This is her mom..." I turned and indicated her.

"Jennifer," she said, extending a hand to Cynthia. Cynthia looked a little relieved as she took Jennifer's hand.

I did not think of her as a 'Jennifer.' I never would have guessed that was her first name. Perhaps I had never known before that afternoon. I ordered my usual lunch, a couple of chicken patty sandwiches with fries and a soda. Jennifer ordered one of the combo meals. We sat together and talked while we ate.

"So, what are you doing these days?" she asked.

"I got out of the Navy a couple months ago," I answered. "I plan to go to college, but I have to wait for my SAT results. Right now, I'm just living with my folks and taking a little vacation after all that time in the Gulf."

"How was that?" she asked.

I chewed and thought about it before answering. "There's a great quote for that, but I can't recall now who said it. 'War at sea is months of boredom punctuated by minutes of sheer terror.' That pretty well sums it up."

Her eyes were wide at that. "What happened? Why the 'sheer terror?'"

"Our boat nearly hit a mine in the Persian Gulf," I shrugged. "The rest of the time, we had a few false alarms. But when you're in a war zone like that, you have a high 'pucker factor' when you're running to your battle station."

She laughed prettily at that, covering her mouth with one slender hand. I realized at that moment that Jackie's mom was actually pretty hot. I had never had a thing for older women, so I hadn't really looked at her as a 'real woman' before.

"That's an interesting expression," she said, still chuckling.

"How about you?" I asked, "What are you up to these days?"

"I do a lot of volunteer work at the school," she said, "I took a couple of classes at the community college this past spring. I may go back to school for a degree after Brent graduates. I need to find something to do with my time."

Her look told me college hadn't been what she had hoped. I didn't know anything about her two marriages, but it sounded like she was financially secure, at least. She finished the last of her lunch and smiled at me.

"It was lovely seeing you again, Nathan," she said.

"It was really nice to see you again...Jennifer," I said. I shook my head and gave her a rueful smile. "To be honest, I don't think I even knew your name was Jennifer until today. I always thought of you as 'Jackie's mom.'"

She looked a little sad at that. "You must think I am so old." Her voice was just above a whisper.

"Actually, I was thinking you hadn't aged a day since the last time I saw you," I replied. "On the other hand, I am so much older-looking now."

This wasn't some idle compliment; I had been a gangly teenager the last time I had seen her. I was a broad-shouldered man now. She smiled at me and stood up. I stood and offered her a hug. She seemed surprised at that, but she let out a really sexy, soft little sigh in my arms. It was arousing to hear it.

I walked her out to her car afterwards, and then walked back inside after waving good-bye. Cynthia fixed me with a glower from behind the counter, and then tried to quickly turn that into a smile when another customer walked up to the counter. Later, I was surprised at just how venomous Cynthia was toward me.

"So, did that tramp give you a blowjob in the parking lot?" she hissed.

"What?" I was completely baffled. "What are you talking about, Cynthia?"

"That Jennifer woman was all over you!" she said, "I thought she was going to jump right into your lap and fuck you in my restaurant!"

That thought seemed so ludicrous it didn't even merit a response. However, when I laughed at the idea, Cynthia got even more pissed off.

"Don't you dare laugh at me!" she said, "I know what I saw."

"Cynthia, please calm down," I said. I had raised my hands defensively. "I haven't seen her since I dated her daughter back in high school. Believe me, there was nothing going on there."

She did calm down, but that outburst let me know that Cynthia was a lot more possessive than I had realized. I drove home shortly after that and tried to figure out what I could do to make it up to her. At the same time, I was a little annoyed that I felt I had to make it up to her. I hadn't done anything wrong. I figured I should sit down and talk with her about it. Maybe she had a boyfriend who had cheated on her, so she was overly sensitive on the topic or something like that.

When I knew she had gotten off work, I drove over to her parents' house. I didn't see her car there, so I went up and rang the doorbell. Her dad answered the door. Now, I had only met her dad once before, and that had been years earlier. It took a moment before he recognized me.

"Ah, Nathan," he said, "What can I do for you?"

"Sorry to bother you, sir," I said, "Will Cynthia be home soon? I wanted to talk to her."

"She doesn't live here anymore," her dad replied, "She has an apartment with her boyfriend, Quentin."

You could have knocked me over with a feather. I'm sure it was obvious from my expression.

"Are you alright, Nathan?" her dad asked.

"Yes, sir," I said, regaining my composure, "I was under the impression she still lived with you guys from the last time we talked. I didn't know she and Quentin were dating."

"Oh, they've been living together for a couple of years now," he said.

I managed to smile at him, but I was fuming inside. Quentin and I had been friends in high school. Not the closest of friends, but I did like the guy. This whole revelation came completely out of the blue, and I was pissed. Still, I managed to smile.

"Wow, that's great," I lied, "You know, Quentin and I were friends back in high school. If it's not too much trouble, could you tell me where their apartment is? I'd love to catch up with them both."

"Sure thing!" he said brightly.

He gave me directions to the apartment complex, but I knew where it was. I drove over and sat in my parked car. I had calmed down on the ride over. Now, I was trying to figure out what I should do. Like I said, I liked Quentin. If he was happy with Cynthia, then I didn't want to ruin it for him. I was pissed at Cynthia because she had been lying to me since the moment I ran into her weeks earlier, and yet she was the one getting all possessive and mean. I saw Quentin get out of his car, and I popped out of my car to holler at him.

"Hey, bud!" I shouted, "Long time, no see."

"Oh, wow, Nathan!" he called back, "It's been years, man. How has the Navy been treating you?"

I laughed at that, and then regaled him with 'sea stories' for a good half hour. Cynthia came out of their apartment and walked up to us. At first, she looked annoyed at Quentin. When she saw me talking to him, the color drained from her face. That moment alone was enough for me. She knew I could really hurt her, but I didn't need to anymore.

Quentin smiled at her. "Nathan, do you remember Cynthia? We've been together for two years now."

"I do remember Cynthia," I said with a smile. I reached out and shook her hand, giving it a firm squeeze before releasing it. "In fact, I ran into her earlier at her restaurant."

"You should come up and visit!" Quentin said enthusiastically. Cynthia looked horrified. I smiled at her.

"I wish I could, Quentin, but I really have to get going. It was awesome catching up with you, though." I gave him a big hug and shook Cynthia's hand again. "Seriously, though, good luck to you guys. Maybe I'll see you around before I head off to college."

An hour after I got back to my parents' house, Cynthia called. "I can explain!" she said as soon as I answered.

"You don't have to explain anything, Cynthia," I said. I was totally calm by that time. "You did what you did, and I enjoyed being with you. I really like Quentin, though, so that is over."

"Are you going to tell him?" Her voice was a ragged whisper.

"No, Cynthia, I am not. He seems to be really happy with you, and I don't want to punish him for what you've done," I shook my head, and then grinned when I realized I was on the phone and she couldn't see it. "Look, Cynthia, I was really pissed off when I found out what was going on. I'll admit, I wanted to hurt you—especially after you gave me so much crap earlier. Do yourself a favor, though. Treat Quentin right. You two could be happy together if you try."

"I'll try," she said. It sounded like she was crying, and I wanted no part of that.

"Goodbye, Cynthia. Don't call me again. Got it?" My voice was firm.

"But.." she started.

"No," I cut her off, "We are done. If I find out you dumped Quentin, or treated him badly, I will tell him everything. Now, are we clear?"

"Okay," she sobbed.

"Good," I said, and then I hung up.

That episode did put me off for a couple weeks. I did get another call from Cynthia's number three days after that phone call, but I didn't answer. She didn't leave a message. I wasn't really looking for someone else to date, but I did find I was getting really horny. Cynthia had been good in the sack. As infuriated as I was that she had misled me, I had enjoyed our time together up until that last day.

One of the most annoying things about being back in my hometown after four years away—particularly now that school had started—was that my closest friends were all gone, and there just wasn't much to do. After living in San Diego...well, it just didn't compare. I started working out at the gym just for something to do. My parents had a family membership there, so they were actually happy that I was taking advantage of it. I had done a bit of weightlifting while I was at sea, but hadn't been all that serious about it.

Here, I had three personal trainers—all guys, unfortunately—who had little else to do besides hang out, spot me, and chat in the mornings and early afternoons that I went in. They did give me a ton of great advice for improving my workouts. I started taking amino acid supplements right after my workouts, also on their recommendation, and those were almost miraculous. They made my muscle aches just disappear, even though my workouts were getting progressively more intense. I could easily see the difference after just two weeks. I had never been so muscular and ripped.