Well, why not?

  • Posted on January 6, 2017 at 2:00 pm

By Naughty Mommy

“The bottle’s almost empty,” said Claudia. “Here, finish it off.”

She poured the last of the wine into my glass, then picked up her own, which contained another swallow or two, and grinned, “Let’s drink to us.”


We clinked glasses and drank. I’m not really sure why we were drinking to us, though — two divorced women, a pair of pathetic losers who couldn’t get dates and were stuck having dinner with each other once again.

Claudia and I were at Mario’s, a small, quiet Italian restaurant with good food. It was where we went every other Saturday night if neither of us had anything else to do, which usually was the case.

Also as usual, I was feeling depressed. I always hoped that this would be the week I’d have to tell Claudia I couldn’t meet her for dinner because I had a date. A date, with a man! How long had it been since I’d enjoyed that? Too long. Following my divorce four years earlier, I’d been on fewer than a dozen dates, with none leading to anything really worthwhile.

I’d had sex only a few times during that period, figuring the man was nice enough and good-looking enough — plus I never knew when the next chance might come along. So I slept with a couple of the guys, Ronald once and George twice. Once was quite enough with Ronald, thank you very much, and George never called again after the second time. That had been almost two years earlier. In all the time since then, my only orgasms had come from masturbation. I was constantly wearing out the batteries in my vibrator.

Why were good men so hard to find? That was the question Claudia and I lamented every other Saturday. Her luck with dating wasn’t much better than mine, and she’d been divorced twice as long as me. So, we sat and slowly ate our dinner and drank our wine and commiserated with each other.

This week, however, Claudia had another idea.

“Do you ever watch lesbian porn when you masturbate?” she asked, a twinkle in her eye.

I glanced quickly around at the other diners. The tables were close together, but as far as I could tell, no one had heard what she’d said.

“Keep your voice down,” I hissed.

“Okay, sorry,” she giggled. “But do you?”

Shrugging, I said in a low tone, “Sometimes. Not usually, but sometimes, I guess. Why?”

“Well, did you ever think about maybe trying it? I know you’re not, you know, that way. But, I mean, it might be better than nothing, don’t you think?”

I frowned. “What are you suggesting?”

Claudia leaned across the table, candlelight flicking in her pretty blue eyes. Briefly, she put her hand out and touched mine, then took it away. “I’m saying that maybe you and I should try it. Just for, you know, for fun. Have you ever done anything like that before? With a woman, I mean?”

“No,” I shook my head.

Of course, I’d thought about it. Probably most women do at some point. But I never expected I’d be desperate enough to actually try it. I was really only interested in men when it came to sex.

“Well, do you want to?” said Claudia, looking eager. It was obvious that she’d been thinking about this, probably quite a bit.

“It can’t be that bad,” she continued. “And if we don’t like it, we wouldn’t have to do it again. But it might, you know, on the other hand, be pretty nice. Sometimes the women in those videos look like they’re having an awful good time.”

That was true. Although I’d just told my friend that I only watched lesbian porn sometimes, I had to admit — to myself, if to no one else — it was those videos that always got me the most excited. Watching a sexy woman lick another woman and bring her to orgasm was guaranteed to get me off, in a big way. But that didn’t make me a lesbian, did it?

“Come on, say yes,” Claudia urged. “We can go to your place. Audrey’s at her dad’s, right? So we’ll be alone. And if you don’t like it, I promise I won’t push you. I’ll go home whenever you want me to.”

“How long have you been thinking about this?” I asked. I couldn’t help but smile. Her girlish enthusiasm was infectious.

It was Claudia’s turn to shrug. “For a while. For a few months, anyway. I didn’t bring it up before because I wasn’t sure how you’d react. And I kept hoping that I’d, you know, meet someone. Or maybe you would, and then it wouldn’t matter. But now, since we’re both unattached and we have no other prospects — well, why not?”

She certainly had a point. Why shouldn’t we do it? I had no moral objection, and I might even enjoy having sex with a woman. I’d never find out unless I tried.

I paused a moment, thinking about all this. After taking the last swig of my wine, I nodded, “Okay, sure. Why not? Let’s do it.”

We quickly paid the bill and left the restaurant, driving in separate cars to my home, located in a suburb a few miles away. Claudia lived alone in an apartment on the other side of town. She had no children. I had one daughter, Audrey, who was 10. This was her weekend with her father, which occurred twice a month. That’s when Claudia and I would go out.

As I unlocked the door and we stepped inside the house, I was filled with worries.

Could I really go through with this? How would we start? What if something went wrong? What if I made some kind of horrible mistake? I didn’t know how to make love with a woman, even though I’d seen plenty of videos. Would I be inept? Or maybe undesirable? What if, halfway through, Claudia decided I wasn’t attractive enough and changed her mind?

I turned on the lights and we put our stuff down, our coats and purses.

“Um, would you, would you like a drink?” I asked nervously.

She shook her head. “No, nothing, thanks.”

“Okay, well, do you want to sit down?”

I started toward the couch in the living room, but Claudia caught my hand. “Let’s go in the bedroom,” she suggested in a soft voice.

Swallowing hard, I nodded, “All right.”

Claudia was 36 at the time, four years older than me. She had a lovely face — full red lips, big blue eyes, a pert nose — framed by natural blonde curls that fell to her shoulders. Her skin was fair, with a few freckles. She was plump, though, with large breasts, heavy thighs, and a big bottom.

I, on the other hand, was slim, you might even say skinny. Also, unfortunately, I’m not very pretty. My nose is crooked, my eyes too close together, and I have a pointed chin. My boobs are small and saggy, my legs not very shapely. I used to think I was lucky to attract any men at all for dates or for sex, no matter how infrequent that might be. Right then I was concerned that my lack of conventional beauty would turn Claudia off.

That didn’t seem to be a problem, though. She took my arm, squeezing it, as we walked down the hall to the master bedroom at the end. “This should be fun,” she grinned.

After shutting the door behind us, I asked, “Have you, um, ever done this? With a woman, I mean?”

Claudia giggled, shaking her head. “Not really. Not since high school at least, but then it was just kissing, you know, and kind of humping, that sort of thing. How about you? Anything at all?”

“No, nothing. Not even kissing.”

All through school, I’d been shy and quiet, not popular at all with the boys, or with the girls for that matter. It wasn’t until my senior year in high school that I was asked on a date, but only one time. Finally, in my second year of college, I met a guy I really liked.

Warren wasn’t exactly handsome, and certainly not buff. Like me, he was skinny and awkward. But he was very smart and very kind. He started taking me out, treating me like a lady, complimenting me, making me laugh. I fell in love.

I also got pregnant. We were married when I was 21 and he was 23. I was four months along, and already showing. That was with Audrey, of course. What a beautiful baby she was! I dropped out of school, planning to be a full-time mother and housewife. Warren was almost done with his Masters by then, working toward a PhD in Chemistry. His parents were quite well off and it was through their help that we were able to squeak by during those years, with my husband making only a little money as a TA and me staying home.

The marriage was good for a while. We were both very happy, or at least I thought we were. Then one day my world fell apart. About a week after our sixth wedding anniversary, Warren came home and with tears in his eyes told me he couldn’t live a lie any longer. He was gay.

What could I say? I couldn’t tell him not to be gay, and I didn’t want him to be unhappy. I loved the guy. I did then and I still do today. Even if it meant we’d have to break up, get a divorce — if that’s what it took for Warren to find what he was looking for, I would accept it. And I did.

“Is it okay if I kiss you?” said Claudia.

Her question brought me back to the present. “Huh? Kiss me?” I asked stupidly.


Without waiting for a response, she took me in her arms, bringing her mouth to mine. Her lips were unbelievably soft, so much different from a man’s. She held me, her hands caressing my body. Claudia’s tongue sought mine, and found it. I relaxed, gave in, and let her make love to me, forgetting my earlier worries.

* * *

I enjoyed sex with Claudia, enjoyed it very much. It seemed not at all like my recent experiences with males, but gentler, less hurried, more about being in the moment than about rushing toward a conclusion. It didn’t make me decide to be a lesbian — I still longed for the feel of a man’s hard, hot cock pushing up inside me — but for the time being this was nearly as good, if in a different way.

After that first night, when I’d been almost completely passive, I began gaining confidence too, sometimes taking the lead in bed. It was fun trying new things with her, experimenting, learning together.

In some ways, in fact, this was even better than what I’d known before, at least if you counted the number of orgasms I was having. I remember laughing with Claudia one night after she’d brought me to climax yet again, telling her I’d probably come more with her in a fairly short time than I’d had in all my years of marriage to Warren.

That’s not to say he was a bad lover. It’s just that it wasn’t very frequent. For reasons I now understand, my husband didn’t approach me for sex very often. It was usually up to me to make the first move — and being naturally reticent, I rarely did that. We would go for weeks without making love, sometimes several months. And when we finally did get together, it would be over fairly quickly. This was not very satisfying for me, obviously. I still loved Warren, though. He was, and is, a sweet, gentle, wonderful man.

Claudia and I, by contrast, made love many, many times over about a six-month period, as often as we could. Don’t misunderstand, it wasn’t as if we were in a romantic relationship. It wasn’t like that at all. Neither of us felt that way. We were just friends, good friends. The point was simply sex with someone you liked. It was convenient and extremely pleasurable too. For me, however, this was still just a stopgap, something to do until the right man came along.

It turned out, though, that when that man did come along, it was Claudia who found him, not me. She met this guy named Spencer, a friend of a friend, and the two of them hit it off right away.

I was kind of hoping at first that Spencer might be the type who’d be willing to share, that he might like the idea of being with two women at once, either just watching Claudia and me, or better yet fucking both of us. That way I could get back in the action.

When I finally got up the courage to speak to Claudia about this, after they’d been together for a couple of months, she laughed, then kissed me on the lips.

“Oh, you beautiful thing,” she smiled, chucking my chin. “Don’t you think I’ve thought about that too? Of course I have. And if it was up to me… but, you know, Spencer has his own ideas, and that’s just not his thing. I’ve hinted about it, more than hinted, in fact. I’ve asked him. But I’m afraid it’s not gonna happen. He wants it to be just me and him, that’s all. I’m really sorry, sweetie.”

“No, don’t apologize,” I said. “I understand. And I’m happy for you, I really am. I’m glad you found a great guy like him. I hope it lasts forever.”

* * *

So, as far as sex goes, I was on my own again, back to watching porn and using my vibe to get off. That was all right, I suppose, but I missed Claudia a whole lot. I felt lonely.

I did have a few dates from time to time. These were with a guy named Jim, a newly hired employee at the trucking company where I worked as a dispatcher. He was nice and sort of fun, but the only thing Jim really cared about was bowling. That was his big hobby, and it was what we always did on our dates. Our relationship, such as it was, never progressed to sex.

“We’re not dating any more now, just friends,” I said to my little sister Brooke.

It was my daughter Audrey’s weekend with her dad and I’d taken Brooke out to dinner. We were at a seafood restaurant, however, instead of at Mario’s. It was too depressing for me to think about going there again.

“Okay,” my sister smiled, “I wish you could meet someone else, though.”

“Who knows?” I shrugged. “Maybe someday I will.”

Brooke, my only sibling, was 28 and a free spirit. She traveled around the country, earning money as a waitress or a bartender, never remaining in one place for too long. She’d arrived in town a few days earlier and was visiting for a week or two, staying at our house. We hadn’t seen her in nearly three years.

“Any new tattoos?” I asked her. “Since the last time you were here?”

She laughed. “Yeah, a couple.” Brooke was covered with tattoos and had numerous piercings too. I had none of either, except for one hole in each earlobe.

“I’ll show them to you after we get home. Can’t do it now, in public,” she winked, before popping a fried shrimp in her mouth.

My sister and I had not been very close growing up. I was five years older, quiet and reserved. She was outgoing, popular, and more than a little wild. Our parents had a hard time controlling her. In fact, they couldn’t. Flaunting their attempts at reining her in, Brooke got piercings and tattoos, drank too much, tried drugs, had sex with both boys and girls whenever she felt like it. I don’t know how she managed to keep from getting pregnant. She was using birth control, of course, but as I knew from my own experience, that isn’t always foolproof.

After graduating high school, Brooke took off, traveling first to Europe with some friends, then to India, to Thailand, and finally to Australia, somehow making a living wherever she went. It was three years before she came back to the US, all grown up, sporting a bunch of new tattoos, and now a confirmed lesbian.

“So Claudia doesn’t even want to see you on the side? You know, secretly?” she asked.

Over my third glass of wine, I’d told her about my experimental affair with Claudia. Brooke was delighted, but wondered why I’d ever allowed it end.

I shook my head. “No, she wouldn’t do that, and I wouldn’t want to either. Spencer’s too nice a guy. I couldn’t do that to him.”

“Okay, well, she’s not the only woman in the world, you know. There are a lot of others looking for sex — and even if you think they’re straight, most women will go both ways. Believe me, I know.”

“I’m sure that’s true,” I grinned. “But really, I’m not that interested in finding another woman right now. I’m, you know, straight. Or at least I think I am.”

She raised her eyebrows. “You think you are? You’re not sure?”

“Well, I mean, I’ve only been with one woman. And I’ve always been straight, all my life. Of course, I’ve only had sex with three men, and one of them was gay, so…” I started to giggle, realizing how silly that sounded. Brooke joined me. We laughed together.

After we calmed down, my sister reasoned, “You’ve only been with one woman, like you said, so maybe before you make up your mind if you’re gay or straight, or bisexual or whatever, you ought to play around a little more. Give yourself a chance to find out.”

“I don’t know, maybe,” I shrugged, taking a bite of grilled salmon, then looking away.

I wasn’t all that comfortable talking about this subject with Brooke, especially not in a crowded restaurant, and was starting to wish I hadn’t told her about my adventures with Claudia. But she didn’t seem to want to let it go.

“You probably think I’m not the best person to give advice,” Brooke said earnestly. “I mean, my life hasn’t amounted to much yet, and you’ve got a nice house and a beautiful daughter and everything. But I just hate to see you closing yourself off from other possibilities, you know?”

“I guess,” I shrugged again.

“Just think about it.”

“Okay, I will.”

We were quiet for the next few minutes, finishing our dinner. On the way home, we made small talk.

Once we were inside the house, though, Brooke started in on me again. “I’m really serious about this. A few times with one woman is not enough for you to decide about your sexual orientation, whether you enjoyed it with her or not.”

“I did enjoy it with her,” I said, somewhat defensively.

“Well, see? That’s what I mean. You might like being with another woman just as much, maybe even more. Who knows until you try?”

“I know, I know. You’re probably right. But, um, I just… I think it’s easier for you. You’re so much younger and prettier than I am. I don’t, you know, really have that many opportunities.”

My voice caught as I said that, and tears came to my eyes. Damn it! I didn’t want to cry in front of her, and I didn’t want my sister feeling sorry for me. But I couldn’t help myself. I sat down on the couch, covering my face with my hands.

Brooke sat next to me and put her arms around me. “I’m sorry,” she whispered, petting my hair. “I should just shut up. I’m sorry.”

“It’s okay. It’s not your fault,” I sobbed.

She let me cry for a minute or so, murmuring soft words, gently petting, soothing, kissing my hair. When I took my hands away from my face, Brooke drew a tissue from her pocket, affectionately drying my tears, even wiping my nose. I did my best to smile and compose myself.

“There you go,” she said. “All better.”

She kissed my nose, my cheek, and then my lips.

I was caught by surprise when Brooke kissed my mouth. That first kiss seemed to be just loving and tender, comforting, non-sexual. But after that, she kissed me a second time on the lips, and this time there was no mistaking her intent.

“I — what — what’re you —?” I stammered.

“I’m kissing you,” she breathed, as she kissed me again. Now her tongue was in play, teasing my lips, asking to be let in.

“No, I — we can’t,” I protested. “I mean, you’re my sister!”

“So? What difference does that make?”

As she said this, Brooke pushed me down on the couch, gently but firmly. She lay on top of me, kissing my mouth again and again. Finally she drew back and said, “You’re a woman. I’m attracted to you. You want sex, and so do I. Who cares if we’re sisters?”


“You want it, don’t you? You want sex? You want someone to kiss you and touch you and make love with you? Isn’t that what you want?”

“I, I guess…”

“That’s what I want too. So, if we both want it — well, why not?”

I started to laugh.

“What?” asked Brooke. “What is it?”

“That’s the same thing Claudia said.”

“Huh? What do you mean?”

“We were out at dinner one night, and she was talking about having sex with me for the first time, but I wasn’t sure about it, and then she said, ‘Well, why not?’”

Brooke smiled. “And what did you say to her?”

“Um… I said, ‘Okay, let’s do it.’”

“Nice. I like that answer.” My sister brought her mouth to mine again, this time shoving her tongue inside.

Continue on to Part Two


8 Comments on Well, why not?

  1. sue says:

    great chapter ending, beautiful build up, looking very forward to next chapter, yet oddly if it ended right here I would still be very satisfied.

  2. Quinlan says:

    Now that’s a beautiful start to what promises to be a great story.

  3. Evan says:

    Agree with Sue and Quinlan – but hoping for at least a chapter 2, maybe 3! 🙂

  4. Jennifer says:

    I really like the build up of this story already, i am looking forward to what comes next! =)

  5. JetBoy says:

    Another erotic gem from Naughty Mommy. I truly adore this story…

  6. PoppaBear says:

    Super Woman does it again!

  7. David says:

    God I love your work, so erotic and sensual. So hot having sisters make love. Can’t wait to get to chapter 2

  8. Tim says:

    I’m sure I’ve read it before, but that doesn’t make it any less enjoyable. Loved the story, and now two sisters are together, or about to be, I’m enjoying it even more. Well written and arousing, thanks Naughty Mommy.

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