Lonely Days, Lonely Nights

Author's Notes: Realizing every reader is different, let me tell all readers that no matter which category this lands in, there is lesbian sex as well as heterosexual sex, as well as interracial sex all by people over the age of 18. For the very last time, I have gone by justplainjeff for well over 40 years, and I'm not changing for anybody! Live with it! This story is pure fantasy. If I happen to use the name of a real person, it's for authenticity. See if you can find the given name of a star from long ago.

My name is Donna Howard. I just turned 56 years of age, and after over 34 years of wedded bliss, I have been a widow for nearly 2 years. My husband, who happened to be 14 years my senior, dropped dead of a massive heart attack at the age of 68. It was sudden, and left an enormous hole in my heart and was felt by our entire family, as well as our community.

Karl Howard was a true pillar of our society. A tax attorney for 43 years, who never had a mean thing to say about anyone. For a lawyer, that is exceptional.

Some background is called for here. I grew up in a very working class home, in Philadelphia. After high school, I went to what used to called a secretarial school. I believe its called a business school, now. Completing the one year course, I was hired by a medium sized law firm, doing whatever was asked by a group of 5 lawyers, who all specialized in taxes. All five were older men, so I thought I was fairly safe. Being a very naive 19 year old, with a minimum of dating experience, I kept busy learning my job, and staying close to my parents and older brother.

One of the lawyers seemed to take an interest in me, more than the other four. Karl Howard, a very handsome man, not very tall, at just under 6 feet, and very distinguished looking. I need to say, here, that at 5'9", I was the tallest in my secretarial pool.

While working with him on one very important case, as lunch time approached, he asked if I would like to have lunch with him, to continue working on this case. I told him I wasn't really dressed for lunch where he was used to going, but he put me at ease, saying it wasn't any place fancy.

Having a nice quiet lunch, and getting more work done than eating, we went back to work, with Karl thanking me both for the pleasant company as well as getting farther along with his case.

When this case finally wrapped up, and sitting with the clients, Karl made sure the clients knew how helpful I was.

After finishing, he turned to me and asked if he was out of place making those comments. Blushing, I told him how nice I thought it was of him thanking his secretary.

"We lawyers need to be more mindful of how much help you ladies are."

Wow, he called me a lady, and not 'one of the girls' as most of the other lawyers in the firm referred to us as.

Having almost no dating history, being the tallest girl in school, and not being a ravishing beauty, any attention being paid to me, by any man was uncharted territory. Even by a man that much older than me.

I did tell my parents, with both of them cautioning me about the age difference.

After another few weeks, Mr. Howard, as I always called him, called me into his office, and started talking about another case he was given. After covering all the basics, he quietly asked if I would like to go to dinner, with him. Just dinner, he said, no talking business. Taking a few deep breaths, I finally agreed, and dinner was set for the following Saturday evening.

I truly didn't know what to expect, or what to wear. I finally decided on what I thought was my nicest dress, that played down my large D cup breasts, and was a few inches below my knees. Even though it was early fall and still warm, I had a sweater with me.

Karl was ever the gentleman, knowing just what to say to put me at ease. He seemed to know that I was a bit uncomfortable dating the boss, which he also downplayed, all night.

After dinner, on our way back to my apartment, he was just as kind as kind could be. Walking me to my door, with me telling him how much I enjoyed the evening, he actually asked if he could kiss me, goodnight. I nodded, and he leaned in and softly kissed my lips. Wow. A second kiss, and a very sincere hug, and he was off.

I didn't realize how excited I had become until I was undressing, and found my panties were a bit wet. My mother and I had 'the talk' so I knew a little more than just the basics. I had done some research at the library, so I knew even more than she had shared.

I knew if we dated any further, we would do more than just kiss. I had to decide what I was willing to do. Yes, I read about what sex was all about, and yes, I was interested in seeing him, again.

Within another two weeks, Karl asked me for another date. With a very serious look on his face, he quietly asked if I would consider staying the night. I told him, very honestly, that I would think about it.

Over the next few days, before this date, my mother called me. She could tell I had something on my mind, so she asked what was going on.

When I told her, what Karl was proposing, she quietly told me to make sure that is what I truly wanted. When I told her he said it didn't have to be for sex, she laughed, saying a man doesn't ask a woman to stay the night, and not expect sex.

I just didn't want to argue with mom, so I dropped the subject. As we were finishing our talk, she quietly told me to enjoy myself, and to be careful.

Friday night. My big date and weekend was finally here. When I got home from work, I was shaking like a leaf. I was thinking of calling Karl to cancel, when my phone rang.

It was Karl, who asked if I was 100% sure I wanted our date to go on as planned. Before I could answer, he reassured me that if I didn't want to stay, he fully understood.

Taking a few deep breaths, I finally agreed, and started getting ready. About an hour later, he was at my door. With my overnight bag in tow, off we went.

Driving to the restaurant, he very softly explained that we had quite a great deal to discuss, over the next two days. I guess we do, I thought to myself.

Dinner was exceptional, with nothing of substance being discussed. As we arrived back at his house, my nerves started to kick in.

Seeing this, he took both my hands and led me to his living room.

"Donna, I have quite a lot to say, so, please don't interrupt, before I finish. First off, I want you to know just how much I care for you, not just as a secretary, if you know what I mean."

"Second, I have been offered a very lucrative job, in Seattle, by one of the regions largest firms, with one of the named partners having a son, who along with a high school pal, has started a software company, growing by leaps and bounds, and this partner wants me to assist in this company's taxes."

"And, most importantly, I want you to come with me. If not as my wife, at least as my assistant, if marriage isn't on the horizon."

My look of astonishment caused a smile, as he asked if I had any questions.

"Only a couple of dozen," I said.

I hadn't even realized he was holding my hands during all this.

"Before you answer, I want you to know a few things about me, you may not know. You know I'm more than a bit older than you, but in truth, it doesn't bother me."

As he stopped for a breath, I quickly asked, "by any chance, are you more interested in me as a wife or assistant?"

"Honestly, a wife, first, but if not, I value you so much, I would want you as an assistant, and we could go from there."

Stopping for a minute, I moved closer to him, and lightly kissed his lips. Hmmm, very soft. Very kissable. He moved his hands to my face and kissed me with just a little more force. Not overpowering, but still very tender. When one hand dropped to my breast, I sort of gasped and jumped at the same time.

"Am I out of line?" he asked.

Smiling, I told him, if we were using words like wife and marriage, this was bound to happen, some time this weekend.

This gave him cause to caress my breast, again, with my nipple responding, accordingly. Our kisses started lasting a bit longer, with my other breast getting his attention, too.

After a few more minutes, I moved back, trying to catch my breath.

"You know, Karl, I'm not very experienced at this sort of thing, so, if you don't mind, can we take a break?"

In actual fact, I was starting to feel very, very warm. I had done just about this much, only twice, with the same boy, my senior year of high school.

We just sat very close, with my head resting on his shoulder. He started rubbing his hand up and down one arm, as I moved away, giving me just enough room to take my sweater off. He took the initiative and started to unbutton my dress, from the neck down.

When enough buttons were undone, making my bra covered breasts come into view, he blew out a breath of air, but continued unbuttoning the rest of my dress.

Standing, to allow my dress fall to the floor, he held me closer, giving me several more, very warm kisses. I started breathing a bit heavier, myself, as we were starting to enter uncharted territory. He moved his hands, lowering my half slip, leaving me in just my plain cotton panties and bra.

"You're absolutely beautiful, Donna, I hope you know that."

My knees were knocking so loud, I could swear they were drowning out my heavy breathing.

He started leading me, silently, to his bedroom, holding my hand, guiding my way. Once in his bedroom, he took my face in both hands, and when he kissed me, once more, he very gently pushed his tongue inside my mouth. I had heard some of the girls at school talking about this, but it was a first for me.

While hugging me, still standing together, he reached behind me, unhooking my bra. When it started to drop to the floor, my arms moved to cover my large and slightly sagging breasts. He very gently took my arms away, saying I was truly beautiful.

He eased me back onto his bed, while taking off his pants and shirt. This was the first time laying on a bed, with a nearly naked man, in my life. Yes, I admit to being nervous, but I think the excitement I was feeling overcame any nerves.

As he leaned over, taking one nipple into his mouth, licking all around it, while massaging the other breast, my breathing started coming in gasps.

Without saying a word, his hands moved to my waist, easing my panties down over my behind and hips. I had never been naked in front of a man who wasn't my doctor, in my life.

My eyes must have been closed, as I next felt his breath at my pussy lips, causing another gasp, and a small cry of further excitement. I felt like I was wetting myself, before I remembered reading what an orgasm was like, and I was experiencing my very first one.

"Donna, please open your eyes for me."

Opening them ever so slowly, I saw an aroused man for the very first time. I saw him placing a condom where it belonged, and putting a small towel under my behind.

Moving between my opened thighs, and telling me to let him know if he should stop, I felt his manhood at my doorstep. He felt so hard, it seemed as if it would split me in two.

Gently easing past my barrier, I couldn't believe how great a cock could feel inside of me. I put my arms around him, drawing him very close to me, and kissed him, over and over.

Picking up a little head of steam, while remaining very gentle, I must have had three or four little orgasms, before I felt him tensing up, a bit. Just as I felt like my insides would explode, he did just that, deep inside of my core. My God, I was hanging on for dear life.

With tears running down both cheeks, Karl asked if I was OK.

"Better than you can imagine, my love!"

Did I just call him my love? After our very first love making?

Rolling off me, and getting some tissues to catch the drippings, I just laid there, and softly dabbed at my no longer virgin pussy. Now I knew why he put the towel under me.

Getting back into bed, and turning on a bedside lamp, we just looked at each other, grinning.

"I have to admit, to you, Donna, you are only the third woman I've ever been with. And, yes I know I was your first."

After about five minutes of just cuddling, I must have fallen asleep, because the next thing I knew, I felt his body right next to mine. I didn't even remember putting a nightshirt on, and he must have put one on, too.

"Any regrets, my dear Donna?"

Shaking my head, no, I just cuddled as close to him as possible. "Hold me, please."

While in his arms, he lightly brushed his lips against my forehead. Kissed the tip of my nose, causing me to smile.

"I love your smile, I hope you know."

Wondering if he expected me to do anything, I moved one hand down his body, finally touching his flaccid penis. I felt it instantly start to grow, so I kept slowly rubbing. Talk about unchartered territory! As it grew, our kisses became more intense. As our kisses became more intense, his penis became a very large, hard cock.

My mind was racing a mile a minute. Could I put my mouth on it? I knew about this action from some of the more slutty girls from school. I kissed the very tip. I licked around the head, like a tootsie pop. Hmmm, not too bad. I took just about an inch, or two and very slowly moved my head up and down.

Just as another inch went down my throat, I felt his mouth on my other lips. My God, that felt good. His tongue hit my treasure spot, just as one more inch descended into my very warm mouth. Up and down as his tongue probed my very core.

Moving on top of him, my mouth kept up a nice rhythm, up and down, as he added a finger into my very wet sex. Between his very able tongue and now two fingers, I was shaking like a wind blown tree. I kept my mouth very full with about half his manhood, wondering how any more could fit into my mouth, without choking me.

I started to shake even harder as my orgasm built even more. Just as I exploded, nearly screaming, I felt a little liquid leaking out of his prick. Then, with a very loud moan, he started cumming, in huge streams right inside my mouth. Overcoming the urge to gag, I just let all his stuff leak back out my mouth, onto his still hard manhood.

"Oh my fucking goodness, Donna! Oops, sorry about that language."

As I kept staring at his still hard manhood, covered in his own spunk, I was still trying to catch my breath.

"I guess if I just had your thing in my mouth and your tongue in my vagina, a four letter word, or two isn't too bad," I blurted out.

"Donna, my 'thing' is a penis, and you shouldn't be embarrassed to say that word."

Cleaning up his own mess, we were back to laying in each other's arms. I felt a bit less self conscious about my nudity, but still tried covering my breasts.

Moving my arms away from my boobs, he just grinned and leaned over, taking a very long, sweet kiss on one very hard nipple. With one hand, he started massaging the other nipple, getting my pulse revving up, again.

"My God, Karl, you want to do it again?"

"Do what, my love, say that word"

"Do you want to make love again?"

Laughing, as he kissed me, over and over, he got another condom, and started between my wide open legs.

I swear his manhood was even bigger than it had ever been. Not having anything to compare it to, I just took him inside of me, hooking my legs around his hips. Very slowly, he started in and out. Kissing each engorged nipple. My fingers gripping his back. It felt as if he was hitting my spine, he was so deep inside of me.

All of a sudden, he stops, rolls onto his back, and tells me to get on top of him. Guiding his cock into my aching pussy, I started moving up and down, with his hands guiding my hips in that motion.

Oh, my fucking goodness, I thought to myself, this is even better than him on top, if that's possible. With my breasts moving with each thrust, I must have had a half dozen small orgasms, before my body started to really shake, with Karl holding me tighter, and exploding inside of me.

I think I was crying, but in the very best of ways. He held me on top of him, softly whispering in my ear how much he loved me. I looked him square in both eyes and told him I thought I was falling in love with him, too.

Only on our third 'date' and knowing him just over five months, I was very sure of that statement.

After having some breakfast and sitting on his couch, he asked if I had any of those two dozen or so questions I wanted answers to.

I knew what I wanted to ask, but wasn't sure how to ask it.

He seemed to be reading my mind, when, out of the blue, he said, "yes, I am."

"You are what?" I asked.

"I am Jewish, but you didn't know how to ask. Right?"

I just nodded, saying it didn't bother me, but I wasn't sure about my parents and grandmother. Being Irish Catholic, I knew my dad wasn't overly fond of Jews.

"Do you come from money?"

"Contrary to popular belief, all of us are not wealthy. My dad is a mail man, and my mom is a school secretary. I went all through college and law school on scholarships."

"Before you say anything, my parents and grandfather aren't going to be too happy with you, either."

"Does this mean you still want to marry me?"

"More than ever, my beauty!"

"Do you need glasses?" I joked, smiling. "You know you are the first man to ever tell me that."

"I hope you never get tired of hearing those words."

Spending the remainder of the morning, and into the afternoon, just talking to each other and learning as much as we could, finding out he has one older sister, who is a high school teacher, and me having an older brother, working in construction. As dinner time was approaching, Karl got a phone call, that he took in another room. Remember, this was in the mid 80's, pre cell phone days.

I tuned out the soft words I was hearing, and when Karl returned, with a smile on his face, he asked if I wanted to have dinner with his parents and grandfather, that very evening. I knew if we were already become serious, I needed to meet his family.

Surprisingly, I wasn't all that nervous heading to dinner. Just a few blocks from Karl's little house, his parents house was a very nice, cozy house very similar to his own.

Meeting his parents, Henry and Gloria, and his grandfather, George. They seemed cordial, and didn't ask too many questions.

I could tell when George and Henry wanted to say something they didn't want me to hear, they spoke in a language I thought might be German.

Dinner was very pleasant, with the talking kept to a minimum. Nothing was mentioned about my not being Jewish, but I sensed that was the subject of their other language conversation. Karl did tell me, quietly that language was Yiddish, a combination of German and Hebrew.

The one question all three of them asked was, how I thought my parents would react. I had to admit to them that I had a few misgivings about our first conversation on this subject. "Us Irish Catholics can be just as closed minded as any people in the world, just ask the British."

I called my parents as soon as Karl dropped me back at my cozy apartment. Sitting all by myself, after such a fantastic weekend, I felt a bit lonely. My mother's first question, as expected, was how was my weekend. I knew that was mother speak for "did you lose your virginity?"

"Mom, my weekend was fabulous. Karl is a perfect gentleman, and treated me like a princess. And yes, so you don't have to ask, we did make love, and yes, we used protection."

"Oh, my little girl isn't my little girl, anymore."

I could tell she was starting to cry, so I assured her, that I always will be her little girl, and to make sure daddy knows that, too.

Taking a few deep breaths, I asked if we could have dinner, the following weekend, as I did with his parents, this one. We agreed to have Sunday dinner, with grandma there, too.