Dating : Swiping on Women

“Man, I can’t imagine being thirty-five and dating young dudes, swiping, and all this Tinder and Snapchat shit.” Lola, my best friend said this to me while I was catching her up on the recent experiences I’ve had from online dating.

She was curious, occasionally aghast, but mostly entertained by my stories, and happy that I was exploring and putting myself out there. Swiping did not exist when we were in our dating prime. I shared her sentiments. It’s been very fun, but also, very bizarre.

Briefly, this conversation occurred a year ago. I was newly single, a few months out of a five year long relationship. And, oh, it was a bad one. Let’s just say it involved the works- lies, infidelity, vices like gambling and drugs, violence, and of course, moments of deep pain and sorrow.

It was one where my sex drive was one of the first things to go, followed by confidence and any solid sense of what my former self was like. It left me a little bit numb, sadder, fatter, and generally a less interesting person. My mindset went from striving to surviving to managing. It was a fucking miracle that I somehow got out of it. I was in deep and committed to it. How I got in, stayed, and finally got out — well, that’s a story I will share at another time.

But back to my bud Lola-
“Oh! You know what? You should try to sleep with a woman!” she said. At this point, I had also done some exploring in sex kinks, some “sexploring.” It started when I reconnected with some former hookups, before I found the nerve to actually meet new people. Oh, you know, some light role playing, some female domination or “femdom.” This is also a story for another time. Of course, after engaging with enough men, I found myself caught back in the kind of interactions that reminded me why I was tired of them- the whole sick of dick line applied. Women? Why not?

“Fuck it. Sure.” Sounds easy enough.

First time- it’s a different game
My initial attempt was not serious and short-lived. I downloaded a dating app HER, and edited my preferences on Tinder and Bumble to include women.

HER was overwhelming. I counted twenty different options for sexual orientation and another twenty for gender identity. And you were allowed to choose multiple! When I use to date, you were straight, gay, or bi. I felt my age, and a bit embarrassed for not having stayed informed on this vast expansion. It was wild.

I went simply with the truth. I am bi-curious and I am a woman.

I kept my profile brief, just a few photos and a short description: Here looking to meet a hot sexy lady. Interesting too would be a plus. Drinks? 🙂

It was playful and a light way to signal that I wanted a fun time. I thought I hit the right tone while being brief and honest.

I then swiped away casually. When I checked back later though, I had no matches! I was shocked. My experience so far, as a female in online dating had been incredible. I was by no means a super model, but I am generally attractive and fun. I can engage in conversations. I know how to flirt. I got over a thousand matches the first day I signed up for Tinder! It was amazing. But that was a hetero market.

So this was a curious feeling for me, and the first moment where I was conscious about having to adjust expectations. Some initial matches reinforced this.

There was Brandy the “pillow princess.” A young curvy black woman. Her face looked attractive enough, I couldn’t tell if there were any filters. I was in a very open and embracing mode. Let’s go! I gave her a cheerful greeting, “Hii!” She went on to tell me about how she was a “pillow princess” — that she was looking for someone to service her, eat her out. Oh, I thought. No, she is not a returner, just a receiver. Well, that sounds a bit one way? Who is this selfish girl? After she sent me some very explicit photos of herself — straight close ups of her tits and labia- I politely disengaged. You’re hot though! Maybe later? And peaced out.

Then there was Marcia the catfish. She looked Latina and full on sexy. Her photos were like that of an Instagram “thot.” Plump tits, tiny waist, and curvy hips. Very clear pictures. She messaged me first, said I looked sexy. I was excited. “Do you want sex?” YES. As we chatted more, it seemed English wasn’t her first language. Still sexy. I said she was very pretty. But soon she asked me if I could send her pictures of me in sexual context- I find so sexy, she says. A clear red flag. I still held out some hope, and asked her if she’d do it first. But she ignored and I ended it. By the way, this would be the first of several bots or catfish I would run across. New to me. I’ve heard of this before, but never experienced it. It blew.

And finally, there was Kristen. A slim blond white girl. She was pretty enough, in a plain approachable sort of way. A nice smile. Conversation with her was a bit bland, but she seemed open to me. This was the first time I got to the stage where numbers were exchanged. We began texting each other. I found out she was straight. That she just got out of a relationship and was interested in having some fun with a girl. That she has done this before. Great! I was excited that this felt like a real lead. We sounded like we were on the same page. She then asked me if I’ve been with a girl before. Without thought, I answered no. After a pause from her, I quickly followed that I really wanted to and was enthusiastic. Oh gosh, I cringe thinking about how I sounded. She noted she did want someone with more experience, but she continued and asked how tall I was, saying she was five six. Again, without thought, I said I was five — but looked taller in real life!

By the time she asked if I could send a full length picture of myself to her, I was already in eye-roll mode and wrote this off. I’m not sending a picture to her! I don’t even send them to guys. I didn’t appreciate her apparent skepticism. I mean, she height shamed me! Sigh.

So after a month of hit and misses, I lost steam and halted the pursuit. Also my subscription to HER ended (fifteen dollars a month- not awful).

Is this what the average guy felt like while pursuing women online? Inadequate and desperate? Where were all the hot sexy lesbians who just wanted a good time?

Second time- think like a man
After some more tired experiences with men, I cycled back to it. But this time with focus. I took some time to consider my tact. I acknowledged that my attitude and pursuit was similar to that of a man.

“Also, maybe labeling yourself as bi-curious can be a turn off. Women might think you are just pursuing a novelty. And not take you seriously,” Lola suggested this. I agreed. And unfortunately this was exactly how I was treating it.

So I decided to adapt a man’s strategy and perhaps be evasive. Specifically I decided to be more like a so called “fuckboy” or player. Femme fuckboy?

I will be methodical and efficient, treat it as a numbers game. I will not just swipe in an idle fashion- I will swipe on every female. And then flirt my ass off in a proactive and confident manner. Evade questions asking about experience or motivation. Disengage quickly if there is any sign of difficulty. I am no longer bi-curious. I am a lesbian. This was my mindset.

The switch was great. But I was shocked when I started to get mostly young women. Young hot and brazen women looking at me like the seductive older one. I didn’t realize that things could make me blush still.

But when a twenty three year old, leggy brunette, self proclaimed Feminist AF (as fuck), says she want you to do whatever you want to her. That she wants to eat your ass out. You blush. When a hot Indian girl tells you she thinks we should share sex stories and turn-ons, and that she thinks your mom is hot (I included a picture of me and my mother- I question myself too), well you cringe a little, but keep at it.

And finally, when a very pretty redhead twenty-one year old asks me if I like hair- and I realize she means pubic, I pause. And when she continues that she has hair because she doesn’t like the way it looks shaven, I think she is sweet?

When she tells me she wants to have fun, but not in a cold hit and run way, I agree. And when she tells me this older lady once picked her up in her car, and just finger banged her for twenty minutes before dropping her off, I feel sad and a bit guilty.

And when tells me she is really nineteen, I am surprised and say that is pretty young. And when she replies- oh? Are you turned off now? 🙂 I just don’t know what to think. Before I answer though, she goes on and asks what ethnicity am I? Chinese, I says what about you? Swedish, she says and then remarks- we’re both exotic. 🙂 She is lovely.

Me, thirty-five, was flirting with a young nineteen year old girl. I was old enough to be her mom! Of everyone I’ve interacted with so far, I found her most compelling and felt a connection. We continued to chat for a few days. But I couldn’t do it. I wasn’t going to meet her.

Third Time: no more wasting time
I picked up again after a few months. After more life things occurred (another story).

It was a Saturday afternoon. This time around my goal was to meet someone the same night. No wasting time, no dilly dallying! I download two additional women apps: LESLY and ZOE. It was three pm. I quickly learn and navigate these sites, and then diligently swiped away on all the apps. Swipe, match, chat, swipe some more. It was like I was on adderall. Hours went by.

There was Emily, this lovely young pharmacist who just got out of a bad relationship. She wants to just experience some fun and have never done this before. I didn’t think this was ideal. But sure. Oh we can use whip cream to help mask the taste. She was sounding less ideal, but still willing. Then she said today isn’t good- let’s do tomorrow? I unmatched her and quickly moved on.

There was Nicole- an older Asian woman with a blurry picture, but I liked her dog. She wants to chat and pursue some flirting. Good sign. I’m honest with her. I’m really only looking for a nice time. She seems to understand. “Yes, we all have needs.” Condescension? I’m benching you lady.

Wow, Leona was beautiful. Slender blonde, my age. We exchanged numbers. She’s lonely and looking for a pretty girl to take care of- a sugar baby? WTF? This can’t be real, but I’m intrigued? Of course I’m gullible, and after more chatting, more red flags appeared. She was clearly a bot or a catfish. And she was suddenly 8,000 miles away? I blocked her number.

Then Roz- a lovely black older woman. “You know, I’m normally the hot older one.” She was spicy, “Well not this time, young lady!” I smiled, but moved on. She was older than my mother. Just could not.

And finally there was “Miss Honeypot.” Her face was pretty. I recognized the crop and filter of her picture likely masked a larger body. I didn’t care. The only problem was, she was bland sounding. Timid, passive. I had started chatting with her before dinner time, but she looked like a dead end.

It was close to midnight, when I get a surprise message from MissHoneyPot. She had just got back to her parents. If I wanted to get a drink, maybe a boba. SURE. I was excited. I didn’t play it cool. Time was too short. When we found all the places closed nearby. I suggested she come over, or I go over.

She was hesitant. She thinks its safer to meet somewhere. Of course. I apologize. I always thought it was just easy with women. I mean, women weren’t murderers. I’d do the same thing with me. I laugh it off. I start to give up when it does not seem like her tone indicated this would work. So I say maybe another time.

Then she re-engages. She has a joint. If I wanted to share. SURE. She ubers over. I told her I’d get her uber back.

Here’s what it was like. Before she gets over to my place, I take a small swig of whisky and smoke a cigarette. I am nervous, and excited. I don’t want to blow it. I remind myself to stay confident and lead. I already gathered from her profile that she liked assertiveness.

She comes over, and she is a big girl. A little taller than me, and twice my size. But her face is pretty with thick lashes, cheek bones, and full lips. She wears cute thick framed hip glasses. I forget her answer when I asked if she was far or nearsighted.

We sit outside, and smoke this joint. She becomes an overload of information on medical marijuana. I let her go on. I’m not that interested, but I want her comfortable. I don’t smoke much. I took a hit, maybe two at most.
I finally ask her, should we make out after we finish this joint?

Yes. She says. Okay. She will be a good follower. Once she indicates her joint was done. I went at it. For the next forty minutes to an hour, I was on her like an enthusiastic teenage boy. But with some more thoughtfulness. I wanted to make it good for her too. I remind myself to me loving. I hold and squeeze her hands. As I feel amazing touching and sucking on tits and nipples. Feeling a clit that is not my own. Her body is so incredibly different from mine. This is sexy and arousing. She is being a great partner. And I feel full of confidence.

I look at her and say, touch me like you’d touch yourself.

And she does this. She goes at me furiously. My head starts spinning. I forgot to eat while swiping. I drank whisky, smoked cigarettes, and smoked a strong joint on an empty stomach. That plus just breath mints. I am gone.

I was gone. I had to get up. My head was spinning so hard. I tell her I’m sorry. She feels bad for not warning me about how strong the joint is, and helps me up. I vomit a little, murmuring sorry the entire time. I order her an uber after she helps me get to bed, and leaves.

The next morning, I woke up clear headed. I looked at my phone quickly and texted Miss Honeypot. I didn’t want her to feel used. I fucking felt fantastic. Party foul aside, it was incredible. I think of when boys say, “I felt like a man.” Whatever the equivalent was, that was what I felt. I had some regret in not returning the favor to her. I wanted to! I felt bad for never asking her what her real name was. That aside, my mind felt free.

I totally understood then how men could have sex with anyone. I understood attraction to different body types. I wanted to try again. I was glowing.

A few days later, I made one more attempt.

Her name was Mika. She was this twenty-five year old Hapa- half Japanese, half white. Our initial flirting seemed on point. She was giggly and dressed revealing in her pics. She seemed down to meet immediately. Sure!

I met her outside her place. She looked at me, and wanted to know more about what I was looking to decide if she wanted to “fuck with me.”

She was a speech therapist and indie porn star she says. I was of course curious and had a ton of questions. She was thoughtful and open. And we sat in her car and talked about how she’s slept with over hundred partners. How she was in a bad abusive relationship before starting to sleep around. I was floored. She was only twenty-five.

Mika’s story. I learned she went to school in Boston. And there had issues with identity, both sexually and culturally. She got involved with a lot of men. But never a white guy. “Fuck white guys, they’re too entitled.” I smiled when she said this. How she grasped this thought and attitude so early in life. And how didn’t she sleep with a white guy? She was in Boston.

Her porn business was very important to her. She did it as a way to make money and explore her sexuality. She specialized in fetishizing her asianness. And ass play. She would post on Snapchat, and used Venmo for payment. She used Twitter to promote. She makes a lot of money each month. She plays with women. She likes being a freak. But hmm, she couldn’t tell if I was truly attracted to her. I placed my hand on her leg, and asserted I definitely was.

I couldn’t lie to her when she asked me what my deal was though, “I feel like you might be looking at me like a novelty.” This was true. I didn’t have it in be to deny this. I told her about myself though. Was open about my mindset, some of my history. That yes, you would be a new experience for me, but that the attraction is genuine.

It was getting late, and it was clear that nothing was going to happen besides getting to know each other. Because it ended up being an interesting meeting, I wasn’t too annoyed. I said good night. Gave her a kiss on the cheek, and asked her what she thought, about the possibility of pursuing it further.
“Yea, I’d fuck with you.” I smiled.
“So whats your real name?” I asked her. She smiled back. “Lauren.”