A Well-Fitting Skirt

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A young woman is attracted to an older one.
8.1k words
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All of the characters in this story are fictional, but parts of them came from real people I've known. All are above 18 years of age. There are descriptions of sex acts between women, so if that bothers you, please look for other stories!

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I first saw her at the coffee shop. She walked in, leading her little dog on his leash. I liked her look, admiring how her womanly figure was shown off by the way her bodycon top, highlighting her lovely breasts. I guessed about 38D. They looked delicious to me.

My eyes slid down to her skirt. It hit just below her knees and was made of a fabric that had enough stretch to hug and show off her womanly hips. I've always been attracted to women who look like women, not barely pubescent teens. She paid me no notice as she walked by to get into line, but my eyes devoured her beautiful hips and ass, wishing I could be a lot closer to her. I wanted to know how she smelled.

As I admired her movement, I enjoyed the totally smooth look of her lower body, unmarked by any visible panty lines. I looked more closely and realized she actually didn't have any panties on under that amazing skirt. One look at her legs and I saw she was not wearing hose or tights. She was commando and that made me gush.

I go commando under my skirts and dresses, too, at times. I think it's very sexy to be so ready at all times for whatever or whomever I may meet. I really wanted to meet this woman. In a flash, I was up in line behind her, as close as I could get. A little whiff of her perfume and I was in lust.

I had no way of knowing whether she was straight, bi, or lesbian, or even sexual at all. I just took the chance to "accidentally" bump into her, my breasts briefly pressed against her back and my hip against her lovely, soft ass.

"Oh, please excuse me. I'm so clumsy,:

She frowned for just a second and then a small smile played around her lips. She quickly surveyed my figure, checking out my cute tee and denim mini. I wasn't wearing hose or tights, either. I just had a simple bra and panties under my casual outfit. She seemed to like what she saw. "No problem."

She seemed to be waiting for me to say something, so I blundered ahead. "I really like your skirt. It flatters your figure so nicely."

"My figure would do well with losing about twenty pounds around my hips."

"Oh, no. I think you look so nice! I find it so attractive when a woman looks like a woman."

She smiled at me. "Do you, really? Are you attracted to women?"

I blushed, but I forced myself to look her in the eyes. "Very much so. I think you look very attractive."

She moved up and placed her order and then turned to me,. "May I buy you a coffee?"

She added mine to her order and we began to chat. I learned she is a real estate broker and her office was a couple of blocks away. She tilted her head to the side for a moment and looked me up and down again. "Do you have some time to get to know each other a little better?"

I nodded and she grinned. "Come with me."

I gathered my things and followed her out of the coffee shop, admiring the way her hips swayed under her skirt. I was mesmerized and definitely wet.

She opened the passenger side door of her BMW and handed me in. I made sure she had a good view of my panties as I swung my legs into her car. She seemed to like what she saw. She drove to a nondescript storefront in a local strip mall and opened the door for me, offering her hand to help me get out. I made sure to give her another peek and a broad smile.

She unlocked her office door and let me in, locking it behind us. Back in her office, once the door was closed and her little dog freed, she turned to me and wrapped me in her arms as she kissed me. "My name is Audrey. You're a beautiful girl."

I kissed her, exploring her mouth with my tongue while I caressed her back down to her amazing butt and hips. "I'm Annie. I think you're amazing."

We continued to make out for a bit until she began to move me toward the couch. I had something else in mind, though. "Wait. I want to do something. Do you mind?"

She nibbled and sucked on my earlobe, twiddling my earring with her talented tongue. I couldn't wait to see what that tongue could do for me a bit lower down.

Instead, I began to move around her, rubbing my breasts and pelvis against her. "Hmmm, you're so soft and it feels so good to be near you."

She caught on quickly to what I needed and she turned to bring her wonderful ass to my front. I wrapped my arms around her, rubbing my titties on her back and my pussy against her lovely ass. By this time, she had hiked my skirt up around my hips with her hands. I pulled it up all the way to my waist and pushed my panty-covered mons agains her softly-rounded butt.

Once I was right behind her, I pushed my hands under her top and held onto her two wonderful breasts through her lacy bra, pinching her nipples to make them hard. At the same time, I began to hump her butt, taking long sensuous strokes of my pussy against her. My excitement grew as she began to move against me to increase the friction.

I moaned as I kissed her neck and nibbled on ear lobes as they came into range. Her hands reached behind her to my sides, holding me against her as we enjoyed a dry fuck.

"Does my little girl like rubbing Mommy?"

Oh my! How did she ever know?

"Yes, Mommy. Can I keep doing this? It just feels so nice."

"Yes, dearest, Mommy likes when you rub against her."

She turned her head just enough to kiss my cheek, but she held me close in to her, helping my frottage. She played to my main fantasies of dry humping my real mother. I used to do this when I was a little girl. It was very comforting and not at all sexual at first. It was just a thing I did that made me feel good to get closer to my mother.

Mom let me do it until I was about twelve years old and I enjoyed the first orgasm I'd ever experienced. I had a pretty good idea of what had happened afterwards. Girls talk and teenaged girls talk about sex compulsively. Mom understood what had happened and we had the Talk about sex and periods and masturbation and making babies and all that. She never let me hump her again, but I'd already been imprinted. My incestuous first orgasm became the subject of many masturbation sessions and I found as many ways to hump anything in sight as I could.

I suppose it's no surprise that I realized I was a lesbian with a fixation on older women. In fact, women with a figure like my mom's starred in my fantasies. I'd had relationships with women I met in college, including faculty members who reminded me of mom. I often enjoyed frottage with them to some very nice orgasms. I always made sure they were satisfied, too.

It was a surprise to me in the midst of my lesbian explorations that I began to date men, too. I was surprised to learn that I enjoyed a hard cock almost as much as I did a lovely, rounded ass. My world view changed accordingly and I began to identify as bisexual. My favorites were older married couples who enjoyed role-playing parents-daughter scenes. I generally got to hump a motherly woman and got a hard cock into my pussy or my mouth or my ass in the bargain. The older men were far superior to the college-age boys both in understanding of what a woman needs and their patience in helping their wives provide it. I'm sure that the frank naughtiness of role-playing a father who gets to fuck his daughter played into it as much as anything. His excitement added immeasurably to my own.

I had no idea yet of whether Audrey was a mother or married, but she clearly recognized in me a needy little girl. "Dearest Annie, how do you want me?"

I fell in love with her at that moment. Her intuition of my state and needs made me want to please her more than anything. "Mommy? Can I pull up your skirt? Please, Mommy?"

Her tone of voice became warm and loving. "My dearest girl, why do you want to lift Mommy's skirt? Does my little girl want something naughty?"

"Mommy, I love you so much I just want to do something nice to you."

She adopted a humorous tone. "Oh? Now what would that be, dearest?"

"Mommy, I want to kiss you nice."

"You want to kiss me nice? What's that, darling?"

I added a little whine to my voice. "You know, Mommy, nice kisses in places that feel good when you kiss them."

She tilted my face up to meet hers and kissed me on the lips very gently.

"Nice kisses like that? Do you like how Mommy kisses her little girl?"

I closed my eyes, but I held onto her beautiful breasts and pinched her nipples again. Audrey gave me a soft, low moan.

"Yes, Mommy. I love when you kiss me. I just want to kiss you other places, too."

She took in a deep breath and let it out slowly. "My dearest Annie, you may kiss Mommy wherever you like. I love you so much,"

With that, I pulled my tee shirt over my head and unclasped my bra, letting it fall to the floor. Next, I unbuttoned and unzipped my little skirt and let it fall, too, leaving me in a pair of comfortable pink cotton panties with little red hearts imprinted all over them.

I reached down to the hem of her skirt and began to pull it up to her waist, smiling at her as I slowly exposed her thighs and then her lovely cheeks. As I'd thought, she had no panties on. Mine became even more creamy, seeing her womanly ass.

I couldn't wait any longer. I held her breasts in my hands again as I bent her forward to resume humping her soft, gorgeous ass. I was in heaven and I knew I wasn't far from coming. As my climax approached, I sped up humping her gorgeous ass, spreading my legs as far as I could to get maximal contact between my pussy and her lovely bottom.

As I started to lose control, my orgasm washed over me, emanating from my wet pussy to my tummy and the rest of me. I was out of breath, holding on for all I had until my knees weakened and I slipped down to the floor behind her.

She made sure I was okay and then she fetched a towel from her personal wash room. She pulled her skirt down and off, over her hips and then sat down on the towel she'd spread on her chair. When I'd recovered, she smiled as she kissed the fingers of my hand before she pulled me upright.

"Did my sweet girl feel yummies?"

I was on the floor, on my knees. I moved toward her office chair and kissed her lips as I snuggled to the lovely space between her knees and thighs. "Mommy, I've never felt so yummy. I love you, Mommy. Can I make yummies for you, too?"

She kissed me thoroughly and ran her hands through my hair as she looked into my eyes. "My Annie love, I want you to make me feel yummy, too. Would you please give Mommy yummies?"

"Yes, Mommy."

I threw my arms around her shoulders as she leaned forward to share another kiss with me. Starting with her lovely face, I caressed her hair and ran my hands to her neck and shoulders as I continued to kiss her. My kisses migrated to her jaw, down to her neck and to her collar bone. I was gently rubbing my breasts against hers, enjoying the feeling of my hard nipples being dragged along the upper portions of her breasts. I moved downward to take a moment to bury my face between her luscious mammaries, thrilling in her warmth and her natural scent.

I felt her move her arm toward her face. "My dearest lovely girl, I don't have as much time as we need for this. I have an appointment with a client in an hour and I need to take a shower before I go.

"I'm so happy to need a shower for such a wonderful reason, but I don't have much time. Would you like to join me for supper this evening? My treat, of course."

"Audrey Mommy, dinner sounds lovely! I still have to do something nice for you. I can't tell you how you've made me feel. I truly love you! May I just..."

As I said that, I slid down between her thighs and pulled her forward on her chair, pushing her thighs further apart and exposing her beautiful pussy to my hungry gaze. She had delightfully full labia, dripping with her sex juices and an erect clit about the size of the tip of my index finger pointing out of the top of her pussy, looking almost purple and so inviting.... Her muff was trimmed back to a landing strip. Very neat and well-kept.

I just pushed into her cleft and licked her inner thighs, her labia, and then her hood around her clit. She was holding my head close to her while I wrapped her amazing clit in my lips as gently as I could. My clit is very sensitive until I'm fully aroused, so I treated her softly and delicately until she began to hump my face and to moan.

I took that as a signal to begin to suck her clit as though it were a miniature cock. She obviously loved that as it didn't take very long for me to push her over the edge. Her orgasm looked amazing and I was proud to give it to her. As she came, I held her closely, kissing her and telling her over and over that I love her.

She finally collapsed and took a breather and then she looked at her watch. "Oh, shit! Come on take a shower with me, but no play time. I have to meet my client."

I helped straighten up her office and I collected my things, handing my wet panties to her with a sly grin. She beamed as she took them, took a quick sniff of them and stuffed them into a desk drawer. After our quickie shower, I put my things back on and followed her out of the office, again admiring how her skirt hugged her lovely ass.

"What shall I wear for dinner?"

"Wear a nice dress. It's a fancy place and I think you'll love it."

I went home to prepare for my date with my new Mommy.

* * * * *

As soon as I got home, I stripped off my top and skirt and then my bra. I'm usually a home nudist anyway. I just love the freedom of wearing as little as I like at home. It makes me feel happy and it makes some things very convenient, like bathing, peeing, and masturbation. I love to Jill off. I do it whenever the spirit moves and as often as I like.

It was just past noon and I felt I had the time I needed to dress up for my new girlfriend. I've never moved so quickly with a new lover. I hadn't known her for an hour before I was having sex with her. It felt totally right with Audrey, though. Somehow my favorite fantasy of sex with my mom hooked her and she ran with it. I could barely keep up and it felt so amazingly slutty to role play the most taboo incest scene my dirty little mind could concoct. Just thinking about it was starting to make me wet up again.

I shook my head and went to the bathroom to pee. I regarded my reflection and decided it was time to get rid of the pubes again. I've done so in the past for various lovers and even for my own convenience. It's certainly a lot easier to keep clean during my period and it just feels better when my lover is going down on me. For that matter, I prefer eating a well-groomed pussy, too. I was happy Audrey keeps her bush neat.

I got out my electric trimmer and plugged it in. Running it all over my mons and vulva, I enjoyed the fine vibration it makes, adding to my already aroused state. I was very tempted to rub one out, but I decided to let my anticipation build before my date.

Instead, I heated up a pot of water almost to boiling and put hand towels in it. While that was heating, I got my essential oils and chose a rosewood scent to prepare the skin I was about to shave. After oiling my privates, I placed the hot towel on my pussy, I gave it some time to soften the hairs and then applied shaving cream and carefully ran my razor over my pussy. Again oiling myself up, I then shaved my legs and pits.

In my closet, I found a dress I'd bought for a special occasion and took it out of its plastic bag to air out. I selected a lacy white thong and a pair of off-black thigh highs to wear. I wasn't going to need a bra that night. My dress was in hunter green silk, a halter style top with a deeply draped back and sleeveless. The skirt was a high-low style, hitting just above my knees in front and just below them in back. The skirt had a little fullness, allowing it to move prettily around my thighs when I walked, yet it was very comfortable to wear. I anticipated the need to move and to grant access to all the important things as the evening progressed.

For shoes, I chose 3-inch stiletto heeled peep toe pumps in black patent leather with little silver rosettes on the uppers. I sat down to do my nails, stripping off the old color and redoing them in a red lacquer. I did my toes in the same shade.

After my shower, I rubbed down with scented oil and did my hair in a French braid. I pulled my panties on and then my stockings. My dress settled lightly onto my body and I stepped into my pumps. I decided on a simple silver necklace with an unadorned cross, a pair of simple silver hoops, and nothing else. I've never been one to burden myself with lots of jewelry.

By the time I'd finished dressing and stepped through a cloud of my favorite perfume, I felt I was ready to go. I looked at my watch and saw I was just on time. I really wanted to be punctual for my new Mommy. I wanted to make a good impression on her.

I made my way to the restaurant and handed my keys to the valet. I was a few moments early so I walked into the entry where an attendant took my wrap and handed me a claim token. I'm afraid I felt like I caused a drop in the property values as my coat wasn't a designer original, but I was quickly distracted by Audrey's arrival.

She quickly took my hand and kissed my cheek before she surrendered her wrap. I kissed her back and whispered in her ear. "I'm so happy to see you. You look gorgeous!"

She squeezed my hand and beamed back at me. "Honey, that dress is amazing. Wherever did you get it?"

I did a slow pirouette to show it off and grinned at her. "Oh, this old thing? I just bought it off the rack somewhere or another."

She laughed and led me to the Maitre d'hotel's pedestal. "Good evening, Madame Sullivan, table for two, I believe?"

"Yes, Andre. I'd like you to meet my niece, Annie, visiting from Colorado. Annie, Andre is one of my oldest friends. A more trustworthy gentleman you cannot find."

I smiled as I offered my hand which he gently took, bowing over it and not quite kissing it. So romantic! "Welcome to Chez Andre, mademoiselle. I'm truly charmed to meet you."

I smiled at him. "I'm happy to meet you, too, Andre. Aunt Audrey said some very nice things about you."

Audrey took it all in stride, but she was clearly happy I could follow her lead and act as a lady. We should have gone out for a beer and a brat, first. We could have talked about this kind of stuff.

I followed Audrey into the restaurant and I absolutely loved her outfit. She had on a very classy looking dinner suit with a black pencil skirt and a matching tailored jacket with trapunto embroidery over her breasts. Her top was a liquid silver camisole that showed her wonderful breasts off to full advantage. Her amazing ass stretched her skirt across her butt and I so wanted to grab her from behind to just hug and hump her. Her hosiery was sheer black and her Louboutins were silver to coordinate with her top.

She was walking with a little sway of her magnificent ass that formed a sideways figure of eight that I found hypnotic. I wanted to molest her right there, but the general high-class tone of the place gave me pause. I was sure I'd have to have help to figure out which spoon and fork to use if I ate her in this place. Seeing her so nicely dressed, I was embarrassed thinking about some of the naughty things I did to her earlier in the day.

Audrey was seated first, Andre handing her into her chair and helping her scoot it up to the table before he spread her napkin across her lap. Taking my cue from her, I let him seat me in the same way.

I was happy to find we were seated close enough to each other for our knees to touch. I looked up into her eyes and I was lost in pools of dark brown. She put her hand on my knee, just below the hemline of my dress. I covered her hand with both of mine, pressing her tightly to my thigh and gently urging her to touch me a little higher.