Being The Older Woman

This story is an old draft, written before 2020, but I don't think I will get around to rewriting it so here it is.

***

I had never been the older woman before.

Earlier this year I ended a three year relationship with a man. That started not long after the end of a five year relationship with a different man. I was 30 and hadn't had casual sex since my mid twenties. I hadn't really dated since I was in uni.

The big difference I found was in the men I was seeing now. I got to date older men who weren't just looking for someone young they could manipulate or brag about. Just by nature of being 30 I weeded out so many douchebags and players. I still got messages from them, but I wasn't as easily dazzled by a man just owning a suit anymore, not like when I was 19. These men had jobs, would go to dinner with me, and have an apartment I could go back to without anyone thinking I was their daughter or an escort.

However I had lost how to meet women my own age. In uni we were all happy to experiment, and single a lot more. Friends had settled down, or decided their fantasies would remain just that. I always felt a bit weird going to queer nights, I felt too defensive about spending the last 8 years almost solely with men, like it made me less queer.

Then one day I matched with a girl on Tinder, we'll call her Maddie.

I had just been absent-mindedly swiping the night before, not really looking at details or anything, just judging by the first picture. That's a cute dog, worth a date. Skydiving's boring and you're boring for making it your profile picture, anyone can fall to the ground. Nice cardigan, I need to know where they got it if nothing else. The next day at lunch I checked my phone and had a few matches, one was from Maddie. Her photo was of her with mascara whiskers and fake cat ears, holding an unimpressed cat. It was funny and she looked kind of cute and I hadn't thought more about it. Seeing the match I looked more at her profile. She was 19, a student locally, had a fun reference to Bojack Horseman on her profile, and her photos were all a mix of cute and funny. One had her in a bar, posing by the pool table like she was ready to hustle some fools. One had her parodying The Thinker but in a furniture display with a sign saying "good as new". I was immediately nervous in a way I had not been with other people, she was young and hot and I didn't want to take advantage of her.

She said hi and we joked a bit. This was in August, her photo was clearly from last Halloween, and we talked about summer spookyness a bunch. It was light and easy. Other the next couple of weeks I'd hear from her, she'd send a joke or a link and we'd talk for a while and have fun. I was scared to take anything further, we were both aware we met on a dating site, but neither of us had mentioned it or talked about anything like that. She'd mentioned an ex-boyfriend in passing a couple of times, but then again so had I. One day, we were talking about bad flights and I mentioned one I had to Paris when I was going to meet someone I was dating and ex-girlfriend was sat next to me on the flight. It's a funny story but Maddie immediately went "so you ARE interested in women? Or was it just a phase?" We were in.

Over the next week we discussed it more. Maddie thought of herself as bi but wasn't really out and had never dated a woman. She'd kissed some girls, some she liked and some she didn't. This made her feel like she was confused and I told her "it's ok, some people are just bad kissers. You don't have to be attracted to every woman to be bi. Lord knows you won't be attracted to all men to be straight." We joked about weird male crushes, and both agreed Danny DeVito could get it.

She admitted to me what I was scared of. She wanted to be with someone experienced, someone who could guide her through this. I felt both old and empowered, it was scary. I didn't want to coerce her into anything, I also didn't want to be viewed as someone older, something other to her. I'd felt like we'd connected and were peers. I said I'd always be willing to talk with her about any curiousities she had, but thought we should just do so as friends.

We'd become good friends, we talked a lot, we met up for coffee a couple of times a week, we saw some movies together, I cooked for her a few times. A couple of weeks ago we were having coffee early one afternoon when a friend of hers came into the cafe. Maddie introduced us: "Sophie this is my pal Jess, we're on the same course together. Jess this is Sophie..." and I waited for how Maddie would describe me when Jess said "Oh, so this is Sophie. Nice to meet you." and she gave a sultry look to Maddie who had gone bright red.

We made small talk, mainly about their course, they had a lecture in a little bit. I walked them both to the building they were going to, gave Maddie a goodbye hug and Jess the same before going off home. I didn't get much work done the rest of the day, my mind wondering about what Maddie could have said about me. Could she have said we were dating? I'd definitely misread relationships at that age. Was Jess just reading in to it? Did Jess and Maddie have a thing and Maddie was embarrassed about keeping it a secret?

I texted Maddie "It was nice to meet Jess. Hope the lecture wasn't too dry this week." Almost instantly I got a reply. "So dry, I'm basically bones now." We were joking, everything seemed fine, I was just reading into it, we chatted a bit, agreed to meet up for dinner on saturday, and that was that.

Saturday came around, we were going to a cheap italian place. It was November now, a little cold. I wore some dark jeans, tan tall boots, a rust coloured sweater, and went for a pop of colour with a bold red lip. Hair down, coat collar up. I went casual catalogue autumn. Maddie went a different way. I was waiting at our table when in she walked, thigh high black boots, a short tight plum dress with a plunge neck and long sleeves, a leather jacket draped over one arm, a gorgeous deep purple lip, flawless cat eye mascara, and her beautiful hair up in a knot. She strode over with a confidence I hadn't seen from her before and she kissed me on the cheek and took her seat.

People all night were checking her out. I felt they were judging me, either thinking I was too old to be with her, or that I hadn't made the effort.

I told her she looked nice, she returned the compliment. She made no reference to how dressed up she was, it felt unusual but maybe it wasn't. I started to question why I cared so much. Was I really into her? I had become transfixed thinking about she thought of me the other day, and couldn't stop thinking about how she looked now.

We had wine, and our food had come. She asked me if I wanted to taste some of her salmon and I snapped. "This isn't a date. I said I wouldn't date you."

And she said "No you said you weren't going to guide or teach me." I paused.

"Are you saying you don't need that anymore? Did you and Jess?"

"No." she giggled. "I just stopped seeing you as this older woman who could teach me how to be gay, and started seeing you as this gorgeous woman who cares for me and I get on with."

I was taken aback by how confident she had become. She wore it well. I could feel myself getting turned on, thankful for the thick jumper to hide my nipples. "I don't think it's a good idea for us to start dating. I know how you feel. I feel it too." I gulped. "But I don't want a relationship right now."

"I didn't say anything about a relationship." She said staring into my eyes then turned to her meal and continued.

What happened next was a less sexy part. We discussed it more, like adults. Setting out that we both wanted this but knew it was a casual thing, and our friendship wasn't a romantic one still. It was a good and fun conversation, and having it over dinner meant afterwards we could just get an uber back to mine and we knew the deal.

We waited until we got back to mine, holding hands in the taxi, giving each other looks, but we had not kissed yet. Our driver asked us how long we'd been together and I smiled and said "we're just friends." He didn't believe us.

I closed my front door behind us, and went to the kitchen to pour us some wine. Maddie had made her way to my sofa and kicked off her boots. We cheersed our glasses and took a sip. Maddie suddenly seemed like her normal self some more, she knew how to turn it on to seduce someone, but now the moment was here, with a woman, she was unsure how to proceed. "So what do we do now?" she asked. And I kissed her. Pushing back the one loose strand of hair that had fallen out of her do, holding her cheeks, I kissed her.

I hadn't felt a passion like this in truth be told a couple of years. Her lips parted, and our tongues met. Her hands fell to my hips as I pressed forward. Leaning over her. Our kiss broke and I looked down at this 19 year old in my arms and saw the lust she looked back at me with. She initiated the second kiss.

We fucked for three hours that night. Relishing in foreplay. Exploring each other's bodies. Maddie marvelling at mine with an awe I hadn't experienced before. She'd never seen another woman naked in a sexual context, felt their breasts heavy in her hands, moldable, playful. She loved exploring with her mouth, kissing soft skin, teasing nipples, tasting pussy. She relished the opportunity to eat me out, eager to try things, willing to listen, determined to make me feel amazing.

And on the other hand, getting to play with her, I feel bad for thinking it, but I understand a little why these older men would prey on younger women. It felt nostalgic and new at the same time. It was like I was back in uni playing with my friends. Everything so much tighter than it was on me. Which is not to say it was better, but it was an exciting novelty to experience again.

And seeing her experience all this for the first time, what my neighbours must have thought. She moaned so loudly just from me playing with her nipples. She had clearly had inattentive boyfriends before, boys who wanted to please themselves using her, not please her using themselves. Witnessing her orgasm the first time from my tongue was beautiful. The second time made me realise I had changed her life. I thought back fondly to my first experiences, and imagined what future ones Maddie would have.

The whole night was some of the best sex I have ever had. "I wish we'd done this months ago." I said wistfully as we collapsed into bed.

"I don't." Maddie replied. "If we'd done this months ago it would have just been us fetishising each other, using each other. This way we got to do this as friends, as partners." I kissed her again.

I had never been the older woman before, and I still haven't.