Third Time's a Charm

Both my kids broke out in huge smiles, thanking me for being the coolest father in the world.

"Just so you know, your mother knew a while ago, too, and was OK with it, too. She convinced me to accept this, along with her."

To be truthful, I was relieved their relationships were out in the open. Talking for several hours, after dinner, I realized both their friends were very nice youngsters. The fact they were gay made no difference to me, whatsoever.

Starting their second year of college, Charlie and Alan asked if was OK with me if they moved into an apartment, together. I thanked them for asking, and told them if their grades slipped, I'd put an end to that living arrangement. They both agreed.

With Christie starting college, she too asked about sharing an apartment with Gail. Same grade requirement from me, so they all seemed to be happy.

A few months later, at work, Jenny visited me with an invitation. I knew her husband, Hal, had passed away more than a few months previous, and she invited me to his unveiling.

When I looked at her as if she were speaking Greek, she told me Hal was Jewish, and tradition states the headstone remains covered until nearly a year has passed.

She gave me the address of the cemetery, and I told her I'd be there. She also told me to invite my kids, and their partners.

A very short service was held graveside, and we were invited back to her house for a very nice meal.

Her two daughters and sons-in-law plus three grandchildren were there, too. Her kids talked with mine, as they did know each other from company get togethers.

I just sat off to one side, by myself, when Jenny came up to me and very quietly told me she wasn't opposed to having dinner with me, at some time.

I just looked at her, stunned, and asked if she were serious. Nodding, she actually told me that she and Hal had discussed this very topic, in his last few weeks, before his cancer finally killed him.

I was absolutely stunned. I just sort of nodded, and said we would discuss this, very soon.

"Good, next Saturday is fine with me," she said, smiling.

The next morning, both my kids called me asking when Mrs. Ross and I were finally going on a date.

"It's not a date, it's just dinner," not realizing my voice was raised.

Yeah, right, was the answer I heard from both of them.

I sat back and wondered if I remembered how to go on a date. I hadn't been on a date in over 20 years.

Friday at work, I get a text from Jenny, asking if I'd picked out a restaurant to take her to. Yes, I replied, and told her where we were going, then added I was scared out of my mind. All I got in return was one smiley face.

When I knocked on her door, the next evening, she was absolutely ravishing. Dressed very nicely, not over done, but with class, as I would have expected nothing less.

"Greg, I'm sorry if I've embarrassed you, but this has been on my mind, since Anita's passing. And before you say anything, this is not an invitation for you to sleep over, tonight!"

With both of us grinning, off we went. Driving to dinner, I kept thinking to myself, she's 6 or 7 years older than me. She's my boss. And, oh, yes, she's my boss!

Over dinner, she asked if my problem with dating her was because she was my boss? When I told her she was right, her response floored me.

"OK, how about I sell you the shop, and I won't be your boss?"

"I don't know what to say, Jen, I'm honored, but don't know if I can pull this off."

"If you're worried about the price, I'll have my lawyer get in touch with you, Monday morning."

All the way home, I was wondering what might happen. Walking her to the door, she turned to me, taking my face in her hands, standing on her tiptoes, and giving a very soft, sensual kiss.

"Come by for lunch tomorrow, and we'll talk."

After a long hug, and another scorching kiss, I was off. Wow, can I run the entire shop? Do I want to? Yes, and definitely yes.

When I arrived at her house, I sat in my car thinking of all the what ifs.

I looked at my phone and saw a text from Jen, saying she wouldn't bite, so get my behind out of my car.

Laughing, I went to the door. I was greeted with a nice hug, and one little kiss.

Over lunch, we talked about many things, but not about me taking over her shop. Just as we finished, she got up, placing the dishes in her sink, walked over to me, taking both my hands and coaxing me out of my chair. Putting her hands on my shoulders, she pulled me to her, giving me a very slow, sensuous kiss. Then another, wrapping her arms around my neck.

Taking her in my arms, I whispered, "are you sure?"

"Not really, but, oh, shit, I don't know what I'm doing, Greg."

Just looking into her eyes, I held her close to me, saying, "lets just sit and talk, OK?"

Nodding, we moved to her sofa, sitting with her head on my shoulder.

"I miss him so much, I just hope I'm not making a fool of myself."

"You aren't, be assured," I mumbled.

"You know he's the only man I've ever been with, Greg."

"Sh, let's just sit here, and enjoy each other's company."

Rubbing her shoulder, I felt her start to calm a bit. Lifting her chin, I very softly kissed her on the lips. Then a second time, probing with my tongue. Her response was to move back, a little, but then she moved back, enjoying a third, very deep kiss.

Silently, we got up, and moved quietly, toward her bedroom. Stopping to kiss, again, I started to lift her shirt over her head, leaving her bra covered breasts in full view.

I knew she was large, but her size took my breath away. I leaned over and kissed the tops of both breasts. Then kissed each bra covered nipple, causing them to nearly burst through the material. Reaching behind her, I started to unhook her bra. Just as it was going to fall away, she held it in front of her. I gently moved her arms out of the way, allowing her bra to fall.

I also kissed her, very softly, keeping her from saying anything. I moved one of my hands down to cup one very large breast. Feeling her enormous nipple enlarging, I leaned over, sucking very gently.

Sitting her up to remove the rest of her clothing, as well as my clothes. As we laid back on her bed, all I heard as I kissed my way down her body, was a soft, "be gentle, Greg."

As my kisses reached below her tummy, I heard her gasp, as my lips kissed her lower lips. As my tongue touched her sacred spot, she cried out for me to stop.

Shaking in my arms, with her head buried in my chest, she was quietly sobbing.

"Shush, shush, Jen, please don't cry. I'll stop, if that's what you want."

"I'm such an old fool," she managed to get out, between sobs.

I just held her in my arms, trying to calm her down. A few minutes later, I heard a quiet voice asking me not to hate her.

"I could never hate you, my dear, you've done so much for me, I just couldn't. Do you want me to leave?"

"Please don't. Just hold me, if you could."

Laying on my back, with her body right next to me, I felt her warmth was causing my manhood to come back to life. I felt her hand moving down my body, and when it touched me, I heard her gasp, again.

"Greg, please just let me touch you, if you would. I've never seen anything that size, before."

"OK, Jen, I'll go along with anything you want."

I felt her hand slowly move up and down my shaft, which really felt great.

"Can I continue?"

I just nodded, and slowly started thrusting my hips up into her moving hand. I knew I wasn't going to last very much longer, and she must have sensed that, too, as her speed picked up, and soon, I was shooting stream after stream all over my chest.

As her hand slowed, my breath eased, and I whispered to let me go and clean up.

Getting out of bed, I headed to the bathroom. When I returned, her bed was empty. I saw her sitting on the small sofa in her room, and I could tell she was crying.

I sat next to her, holding her body next to mine, rocking her back and forth. A few minutes later, I asked again if she wanted me to leave.

"No, Greg, just hold me for a little more, then I want to try to get some sleep, if you don't mind."

When I was assured she was doing better, we both got back into bed, me in just my boxers, and she in her nightgown.

I held her closely, making sure she was doing better. When I heard her soft, steady breathing, I finally fell asleep, myself.

Sometime during the night, I turned my head to face her. She took my face in her hands and gave me several very soft kisses. Putting her finger to my mouth, implying I should be quiet, she started kissing me, again. This time with a bit more gusto.

I bravely put one hand under her nightgown, and realized she wasn't wearing anything underneath. My hand ran up and down one leg, stopping just short of where her legs met.

She started thrusting her hips against my hand which invited my fingers to go exploring. With one finger gently rubbing up and down her very wet slit, I found her hooded treasure, and gently rubbed it between my thumb and forefinger.

Her hips started thrusting faster, as I eased a finger deep inside her steaming sex. As I bent down, taking an enormous nipple in my mouth, her body shook with her first orgasm. Rolling her onto her back, I moved between her thighs, and very carefully inserted my rock hard cock deep inside.

"Careful, careful, please."

Slowly, in and out, I could feel her body shaking, again. Picking up the pace, a bit, I felt her body pushing back against mine.

Hanging on for dear life, I felt her entire body shaking over and over. Just then I exploded deep inside her core.

"Oh my fucking goodness, Gregory, you devil, you. Never in my life have I ever felt like that. Hal and I had a very nice sex life, but this was amazing."

"I am so glad you approve," I said with a mile wide grin.

After a little cleanup, we just laid back in bed, in each other's arms.

"Just so you know, both my daughters gave me some advice, but I wasn't prepared for this, to be perfectly honest."

"Are you disappointed?"

"Oh, quite the contrary. I just don't think I can discuss this with either of them."

"Are you embarrassed to talk with them about this?" I asked.

She just nodded, saying that talking about sex wasn't done in her family.

"Well, they learned it somewhere, as they both have kids," I replied.

I looked her in her eyes and could tell she was blushing. I asked if she didn't want to talk about it, and she just nodded.

Monday morning at work, one of the Ross legal team visited me, and stunned me when he produced a contract to purchase this shop.

Does anybody reading this remember the old Woody Guthrie song, A Dollar Down, And A Dollar A Week? This offer was close, but a bit higher. This business, probably worth close to a million dollars, was being offered to me for pennies on the dollar.

I couldn't believe my good fortune. Not only am I recovering very well from a near disastrous divorce, I've found a possible new love in my life. Both my kids are in very solid, if unconventional relationships. My longtime workplace is now going to be my own.

Signing the paperwork, I just sat back in my chair, thinking about how lucky I am.

As I was daydreaming, I get a text, asking if we had a deal?

I couldn't answer yes, fast enough.

Now, all Jenny and I had to decide was, could we make a couple? I thought about it ever since our 'first date' I was just two years removed from my marriage. Jenny and I had a great, if not trying time finding out if we were compatible in bed. To be honest, both of her kids' families, and my kids and partners were all very much in favor of us getting together.

I truly had to give our relationship some serious consideration. For years, I thought of her and her late husband as second parents, they were so very nice to me. And now, she was basically giving me ownership of the shop I'd worked at since I was 17 years old.

Oh, shit, I'd been there for 30 years! I never stopped to consider that fact. It was the only true job I'd ever had.

I called her, on my way home from work and asked if we could just have dinner, like normal couples do. She couldn't agree fast enough, but told me we were anything but normal.

Getting to one of our newest restaurants in our neighborhood, we had a marvelous dinner, which ended with Jen asking if I would stay the night.

"Only if we both act like responsible adults," I said, grinning.

That earned me a mock punch in my arm.

Getting back to her house, we sat in her living room, just holding each other, when she stood up, taking me by my hand and leading me, silently to her bedroom.

Just inside her room, she took my face in her hands and gave me a very long, sensual kiss. Then another.

Stepping back, she unbuttoned her blouse. Unhooked her bra, and stepped out of her skirt. In just her panties, I quickly removed my clothes, and took her in my arms, kissing her fully engorged nipples, making her breathing come in gasps.

We moved to her bed, where she placed me on my back, kissing my chest. Then my tummy, while taking my cock in one hand. Slowly, she kissed the head of my growing cock. Taking the first two inches in her mouth, then up and down. Each time her head bobbed up and down, another inch, or two slid into her warm, welcoming mouth. I moved her on top of me, licking all over her freshly trimmed bush.

When my tongue coaxed her clit out of hiding, she shuddered through her first orgasm. Up and down my manhood. Licking up and down her swollen slit. More shuddering. Another little orgasm.

With me holding her hips tightly, and over half my eight inches in her mouth, I felt my body start to shake. Just as I exploded, she let my offering slide right back down my sex. Nearly the same time, she soaked my face with her own love juices. Still, not a word was spoken.

Holding onto each other, using a couple of hidden towels, we cleaned each other up.

Laying in each other's arms, she whispered, "Greg, I think I truly love you."

"Jenny, I'm positive I'm in love with you, too."

"Did you notice that I had a very nice talk with both my daughters about that forbidden subject. And are you aware that I had never done 'that' before."

"Jen, you can say the words, oral sex," I said.

"Don't push it, you sex fiend, you," she said with a laugh.

I just took her in my arms, kissing her as tenderly as I could. We both noticed that I started getting hard, again, so she rolled onto her back.

Without saying a word, I moved her onto her knees, rubbed the head of my cock up and down her exposed pussy, and gently slid inside.

Before we both exploded, we tried another new position, for her, with her on top.

"Oh my God, I didn't believe my girls, when they told me about these other positions, Greg." After a little delay, she told me that was just about her limit of new things to try.

"They told me something else, but there's no way you're putting that thing anywhere else, in my body."

Knowing where she was referring to, I told her I was more than satisfied with her experiences we'd shared, knowing how many were firsts, for her.

The following weekend, both families had a picnic at my house, all four kids, two spouses, two partners, plus three grandchildren, learning a fourth was on the way, when we both told the assembled group that we were getting married.

We'd been talking all week, and came to the conclusion, it was the right thing to do.

Both sets of kids just couldn't have been happier. All spouses and partners, too.

Jenny told me during the week that she was positive her late husband was very excited thinking she'd found love, again.

I knew the third time for me would be a charm. Knowing my wife to be for thirty years, and never sharing a harsh word, is truly amazing.

Would either of my kids marry their partners? Only time will tell, but both of them are going very strong. Would either of them ever have children? Both have talked about it, but it is a long ways off.

Our wedding was a very nice, cozy affair, with both families enjoying the day. Never once since Jenny and I started getting serious, did I ever think about my deceased wife. We were headed for divorce, and our marriage was long since over.

Now, with all our combined family getting along, all I could think about was when I could retire. We both wanted to travel. And above that, we wanted to spoil any and all grandchildren.

So, there you have it. Third time was definitely a charm, for me.