I thought it would be fun to share some screenshots from my online dating convos, so I’ve created a new Instagram account for that purpose. Check it out, like, comment, follow:
IG: @formerlyunfortunate
Social distance and unrest, and a little bit of sex…
It’s been sad and disappointing seeing people posting and spouting the most unbelievable shit in response to current events this year. No knowledge of civics, no critical thinking, outright dismissal of facts in favor of conspiracy theories and junk science, and a startling lack of empathy or understanding. On that note – if you’re so tired of hearing about racism, just imagine how tired some people are of experiencing it. If I wanted I could do a whole post (or a whole new blog) on these issues. Maybe someday, but in the meantime I had to put my two cents in.
And now back to our regularly scheduled programming. I had a few more dates recently. I’d sworn off dating until things returned to “normal,” but as always I listen to my dick.
#75
This one was another waste of time – one I saw coming a mile away but proceeded anyway. She sidestepped my flirty comments but still seemed keen on meeting me. We ended up at the beach, and I made a joke that she was a little overdressed for the occasion. Indeed she was – with her black pants, black leather jacket, and black heeled boots, but she got a little defensive about it. She reminded me of my older sister, who’d go to the beach with a full face of makeup and would get equally as defensive if you ribbed her for it.
As soon as we got to the boardwalk she handed me her phone to take a picture of her. Not just one, though, but a dozen. She’d snatch the phone back after each one to make sure she looked good. Once again, just like my oldest sister. I rolled my eyes a bit, but it didn’t stop there. We walked down to the big rocks at the water’s edge, and then it was picture time again. And not just pictures of her in various model poses, but slo-mo and time lapse videos as well. She showed me how she edits them all together into video montages of herself set to music.
I made another joke that I was starting to think I was only there to be her photographer, and she got defensive again. Hoo boy.
We sat and made chit-chat and small talk while we waited for the sunset, but it was clear we were a total mismatch. I learned she was an Aries. Once again… just like my older sister. Now, I don’t set much stock by that stuff, but it’s fun to think about and eerie how accurate it is sometimes. But I find Aries women a bit high-maintenance, a bit flaky, and often a bit full of themselves. (Teacher comes to mind; she was an Aries too.) Then she dropped a bomb and disclosed that she was 40, not 30 as advertised. She claimed that she didn’t know why it said that, nor how to change it.
As soon as the sun went down I called it a night and said goodbye. She was making noises about wanting to see me again, suggesting I join her and her friends to go hiking upstate the following weekend. I’m looking for a FWB, not a hiking buddy. I don’t know if she didn’t see that in my profile, or just didn’t understand what it meant, but I was out.
#76
This one lived a bit of a distance away so we picked a halfway a spot – a scenic park on the lake. We took a few laps around the water while we made conversation, but it wasn’t until we landed on the subject of her job as a financial planner that she became really animated. She was really passionate about it… a little too much. After what felt like a half-hour of her TED Talk, I called it a night. It was getting dark anyway. I suggested a movie night back at my place next time. Hint hint. She said she wasn’t interested in anything romantic with me, but maybe we could still hang out.
Sigh. Once again I was like… do these chicks not read my profile, or understand what I’m looking for? I told her I wasn’t looking for anything romantic, nor am I looking for people to just hang out with. So I wished her the best of luck finding what she was looking for and we parted ways. Another one down.
#77
It’s funny how online dating activity ebbs and flows. It was exceptionally quiet after that. The next thing I knew, it looked like my theory was coming to pass – that girls would be so horny and desperate coming out of quarantine that getting laid would be ridiculously easy. I was on track to get laid the next two nights by two different girls. Was it possible? Alas, no. The first one crapped out, so I texted the other and asked, “are you still free tonight by any chance?” Yes, she was. I’ll call her Pharmacy Girl
Long story, it was some of the best sex either of us ever had. The kissing was amazing by itself, so much better than College Girl. (For the record, this one was 28). My dick went in her mouth shortly afterward and I nearly burst right then and there. Her oral skills surpassed anyone else I’ve been with. She was also the first one to ride me cowgirl without it feeling uncomfortable. PG obviously felt she same because gaped down at me and said “oh my God! It’s like a perfect fit!” She also appreciated that I assisted instead of just lying there like other guys.
I flipped her over and pounded her in missionary since she wanted to see what I could do. Either she’s very orgasmic or I’ve become an exceptional lover, because she came hard with her heels digging into my back. It was so intense for her that she was writhing and nearly bucking off the bed. I came pretty hard myself; she felt amazing inside. When she calmed down she said, “Well… THAT’S never happened before.” I’d given her a full-body orgasm for the first time. She tried sucking me off to repay me, but I knew it would take a long time after I’d just came. I told her to get on her stomach and I fucked her from behind. She absolutely loved that, and she got so wet that I kept sliding out. “What’s the matter,” she giggled. “Too wet to stay in?” We switched back to missionary and we each came again.
PG previously told me that she’d never enjoyed receiving oral sex from any man (perks of always dating assholes), but I was determined to be the first. I went to work, teasing my way down and working all around until she was going crazy with anticipation. Then I buried my face in her. I used all the techniques I’d studied and things I’d remembered from old girlfriends. It took a while but I got her there. She was in a daze afterwards, but I wasn’t done yet. I used my fingers to get her off one more time. She was on the verge of climaxing so hard I thought she was going to squirt. No such luck, but I did give her another full body-orgasm and she left puddles all over my bed.
Afterwards she said she couldn’t believe how good I was with my fingers and tongue. “How did you learn to do all that?” YouTube, I joked. From all accounts, I gave her the best sex and oral she’s ever had. I asked if she was staying the night, but she had work in the morning and didn’t have a change of clothes. Dammit. But could we squeeze in one more round before she had to go? I found that we could. One last time in missionary, and we fucked so long and hard that the sweat built up between us and was dripping off my chin in the end. And the eye contact we made… damn. It was so hot.
We exchanged numbers a few days later so we could talk outside the app. I asked about Friday. She had to work. Saturday? Plans with friends. I waited but she didn’t suggest a day in return, so I said I was ready for Round 2 the next time she was free.
I haven’t heard from her since.
I was flabbergasted. How could she not want seconds when the sex was so good the first time? She’d seemed excited at the prospect of regular sex again, but maybe she only intended it to be a one-time thing. I guess I’ll never know. She might still surprise me, but I’m moving on and already have another hot prospect lined up. In fact, tonight is date night. Stay tuned…
Cockblock-19
Just when I was getting into my stride, too. However, nobody close to me is sick or dying or dead, so I can’t really complain. And I’m lucky to say that, considering how close we are to the epicenter. As of this writing there have been over 22,000 deaths in New York state alone. The daily toll has gone down but we’re still losing 400 people on average. Yet some people I know still think it’s much ado about nothing, a big hoax, a Democratic power grab, caused by 5G networks, or some other nonsense.
There’s no telling what effect this will have on dating once things get back to normal (whatever “normal” will mean). Dating will either be freakishly easy because everyone will be horny and desperate after being cooped up for so long, or freakishly difficult because they’ll be more afraid of catching covid than an STD. In the meantime I have to laugh because now everyone’s in the same boat: can’t get a date, can’t meet anyone, can’t get laid… hey, welcome to what was my world for 30 years.
I was still swiping on Tinder and Bumble the whole time I was banging College Girl. I felt slightly guilty but – knowing my luck – things could go sideways real fast and I wanted a backup plan. Sure enough, things ended with College Girl, but due to unforeseen circumstances outside our control. Maybe we’ll get a chance to hookup again, but I’m not counting on it. However, I racked up a few more dates before the quarantine began and people started panic-buying toilet paper (for reasons still unclear to me).
#72
33 years old, from Bumble. Another teacher. We were supposed to meet at this indie coffee shop but they unexpectedly closed early, so we ended up at Starbucks instead. It was an above average date. We talked for two and a half hours and had a nice flow. She’s one of the rare few who actually likes to compare dating stories and experiences. But while she’s recently out of a relationship and supposedly on board with the idea of something casual, she wanted to take it slow and spend more time getting to know each other outside the bedroom first.
Yeah…that sounds more like traditional dating to me. I don’t think that’s how this FWB stuff works. I suspected she wasn’t fully on board after all. She gave me her phone and told me to put my number in, but after texting a couple of times she went MIA. Suspicions confirmed. Although, during our conversation we’d found out I’d once gone on an OkCupid date with one of her friends (Melody, girl #23). It’s a long story how that came up, but talk about a small world. Maybe that had something to do with her ghosting on me.
#73
She was 46, from Tinder, and my oldest date yet. I should have listened to my instincts and not wasted my time with this one, but I have this awful habit of giving people a chance. The initial warning was when I opened Tinder and found two messages from her. The first message was some general question, followed by “oh well, guess you’re not interested in meeting. Good luck to you.” I checked the timestamps and they were sent eight minutes apart. Seriously? “Geez, how about giving me a chance to respond?” I wrote back, and she sent me a facepalm emoji.
Then I suggested a place to meet. “Are they open today?” I answered that they should be and she came back with, “well, why don’t you put on your big boy pants and call and find out,” as if I hadn’t already intended to do so. Normally I would have taken her passive-aggressive attitude and told her to pound sand, but I’m just looking for a sex partner right now so I’m not as fussy. When we met she asked me lots of questions which I was happy to expound upon, but she was pretty tight-lipped when I turned the questioning around on her.
I grew irritated as we were in a noisy-as-fuck bar on a Saturday night, and I was losing my voice from having to talk louder and louder until I was almost shouting. Meanwhile she was one of those people with no concept of traveling of sound and maintains the same speaking volume no matter the situation. I was losing interest and the feeling was mutual. She didn’t talk much and didn’t want to answer questions, so I turned my attention to the live music starting up – which she wrinkled her nose at. What a stick in the mud.
Finally I called it a night and bid her adieu. Waste of an hour and a half. Earlier in the night I had broached the FWB topic and she was like, “this isn’t a date, it’s a meeting” and “I don’t like to put a label on things,” adding that she likes to be friends first and see what happens. Once again… I don’t think that’s how this works. I figure you match, meet up and see if you get along and find each other physically attractive, and move onto the fucking. At least that’s how it works in my mind. Am I oversimplifying it? I don’t think so, because College Girl came right over to my place to have sex without preamble. I struck gold with her, so I’m sure I can do it again.
#74
I had one last date (33yo, from Bumble) before quarantine started. Once again it felt more like a traditional date, although it was a unique choice of venue – the beach in wintertime. I never thought I’d find someone else into stuff like that. However, everyone else in the world had the same idea because it was packed like the middle of July instead of March. We walked six feet apart, doing the whole social distancing thing. That lent itself to a weird dynamic, although she did venture close enough to sample the homemade cookies I’d brought for us to munch on. We got off to a good start but by the end it seemed we were running out of things to talk about. And that was that. No contact afterwards.
***
That’s it for the foreseeable future. I won’t be doing virtual or Zoom dates or any of that nonsense. However I matched with someone on Tinder who possibly shed some light on my struggles. First she admitted she hadn’t read my bio first, so she wasn’t interested in a FWB. Then she psychoanalyzed me based on my pictures, telling me that I wanted kids, that I’m looking for something meaningful, and “you crave connections, bro.” Dafuq? Why, because I was holding an animal? Then she went on to suggest that I retool my Tinder profile, because “anyone advertising FWB subconsciously wants something.”
Yeah. I don’t know what to make of this – thoughts anyone?
And last but not least, I have something exciting to announce in my next post. I’m expanding my social media presence onto Instagram. Details coming soon…
Call Me Daddy
The next time I saw College Girl it was for an afternoon rendezvous that was the hottest encounter yet. We had sex three times in the span of three hours. Near the end of the first round I told her I was getting close, and she sat up and put her hands on my chest. She pushed me back until I was sitting on my heels and proceeded to suck and jerk me off until I came like a lawn sprinkler. It went everywhere; all over her and the bed. Damn. What a mess. During our subsequent rounds she wanted me to choke her, and when I did she cried out things like “choke me, daddy” and “pound me harder, daddy.”
Daddy issues confirmed. Maybe this explains our dynamic and why we don’t talk much (read: at all). Either that or she’s just really shy outside the bedroom. Or both. A few days later she hit me up and asked if I was free that night. We were originally shooting for the following afternoon and I said that would be better for me. Ten minutes later I came to my senses. Passing up/postponing sex? Was I crazy? No, I wasn’t crazy, so I texted her again and said I’d make myself available.
When I brought her back here we spent a good deal of time rolling around in bed between kissing and foreplay. She was definitely better at kissing this time, whereas in the beginning it felt like she was trying to chew my face off. Finally we got to it and had sex another three times. My bedroom floor was a minefield of condoms and wrappers. She slept over again, and while there was still no conversation I noticed she was a bit more snuggly this time.
I woke up the next morning with her hands on my cock. She sucked and stroked me, bringing me to the brink two or three times and before stopping. Ugh. It was torture. We went for another round and I pounded her good and hard for a long time. She was really into it, wrapping her legs around my back and then placing them over my shoulders. I had to keep stopping myself so I wouldn’t splooge too soon, and when I did unload I collapsed on top of her shaking all over. I earned some fresh bruises on my shoulder and wondered vaguely if that was her way of marking her territory. The sex was only getting better and better, and I tossed her around a bit which she seemed to like. Sure enough, I received the following text a few days later:
I was just wrapping up work the other day when I got a text asking if I was free that night. Totally unexpected, but hell yeah I was. I picked her up at 5PM and she came out to the car looking adorable in her oversize college sweatshirt and short white shorts. I gripped and massaged her bare thigh all the way back to my place, and once here I pulled her clothes off to reveal matching white lace bra and panties. Nice, very nice. I was incredibly turned on already.
I went down on her, teasing her for as long as she could stand, and she did the same for me. I told her to keep going until I came, and I very nearly did except I had a change of mind. It was a tough choice, but I didn’t want to deprive her of a nice, hard dick. So I flipped her over, handcuffed her hands behind her back, and went to town. Needless to say I didn’t last long, and clearly I was on the right track because she bit into my arm so hard I nearly bled. Even she was surprised when she saw what she did.
We lay there a bit as I fingered her, and she stroked me as well and I was hard again in no time at all. Very short recovery time and within minutes we were at it again. This time I lasted longer and pounded her deep and hard like she was begging me to. I earned additonal bite marks in the process and we were a sweaty mess under the sheets when we were done. Afterwards we cuddled and dozed until it was time to drive her back, and it was a silent ride as always. I had long since given up trying to have a conversation with her.
I wished we had time for thirds or fourths, but all the students are being kicked out of university housing for the rest of the semester due to the coronavirus. So she needed to gather her things and head back home to NJ. I tried to give her as good a dicking as possible, because that may be the last time I see her for a while – if ever again. Before we parted ways I told her she should take a trip out sometime, noting that the train station was just down the road from my house.
So we’ll see what happens, but if I don’t see her again we definitely had a good run. I was incredibly lucky, and she’s the hottest girl I’ve been with by far. Definitely made up for some lost time and missed opportunities with this one, although in the end the question remains – why did all this take so long and why did I struggle so much? Just bad luck all those years, or was it something more?
Oh well… onward and upward.
College Girl
I was a bit bummed out after date #70, wondering if my search for a FWB would be as fruitless and frustrating as my regular dating attempts. So I was sat on the couch later that night swiping through Tinder when a new match popped up. Damn. She was a pretty young thing. I didn’t get too excited; I’d had similar matches before and they all petered out.
Not this one though… we were barely a couple of minutes into chatting before she asked “when are you free?” I said it was too bad we didn’t match earlier because I was free that night. (It was nearly 10 PM by that point.)
“Conveniently I’m also free tonight,” she replied.
Me: “Are you now… well if it’s not too late for you, I’m down to meet somewhere.”
Her: “Your place?”
Whoa, what? Were we really moving this fast? My guard went up. “That’s an idea,” I said. “You don’t want to meet me somewhere public first, make sure I’m not a psycho or anything?”
Her: “Honestly I’m really just looking for sex.” I sat bolt upright with a very surprised erection. Well, shit. Maybe my luck was about to change. Was this for real though? I was about to find out.
“lol works for me. I’m okay with you coming over if that’s what you want to do. Let’s do it,” I said, despite my better judgment. Once again the smaller of my two heads prevailed. She was a student at the local university and didn’t have a car, so I gave her my address and she ordered herself an Uber. In the meantime I made a mad dash around my house, showering and cleaning and securing my valuables.
#71
She arrived a half-hour later and I was all ready for her. I opened the door and she looked just like her pictures. We exchanged greetings and she informed me that she’d just had her tits pierced so they were off-limits. Dammit… and I’m such a boob guy too. “But we can do everything else,” she added.
“Not a problem,” I said. “Shall we get to it?” She smirked and rolled her eyes and headed off to my bedroom in response. Well, it looked like we were doing this! She was already sat on my bed by the time I got through the door. If you’d told me a couple hours earlier that there’d be a smoking hot girl on my bed, I never would have believed it. It was totally surreal.
I took a seat next to her and leaned in to kiss her. In a flash she was in my lap, straddling me and grabbing me everywhere – fistfuls of hair, cupping my face, seizing my back and shoulders and neck. I was getting super hard, especially when she started tugging on the bottom of my shirt. She rolled onto her back and pulled me on top of her, sliding one hand down the front of my pants to feel me. Clothes were quickly shed and my face went in between her legs. I certainly didn’t need any encouragement, but she was mashing my face into her pussy and arching her hips towards me. She was so wet it dripped off my chin and left puddles on the sheets.
And she liked it rough. With other girls, one finger inside was always enough, but she wanted a second and then a third. Wowzers. She was also into spanking. Smack. Harder. Smack! Harder. SMACK. HARDER! I hit her so hard that my handprint was visible and the slaps echoed off the walls. Hair pulling? You betcha, and she kept indicating more force. Then she wanted me to choke her. I wrapped both hands around her throat while I fucked her, and she kept gasping for me to choke her harder until she could barely articulate the words. Jesus Christ.
Unsurprisingly she was also a biter. Not just my lips and tongue, but my dick went into her mouth a few times and I had bite marks there as well. Ouch. Finally I had to tell her to ease up a little, but not before she gave me my first hickey ever. I proudly sported it the next day, hoping that at least one person would comment on it and I could just raise my eyebrows and give a sly smile in reply. No such luck, but in any case we were at it for two hours that night and I felt like a new man the next morning. Suddenly it seemed as if anything – and anyone – was possible.
We went for Round Two this past weekend, and it was even hotter – not least of all because her tits were open for business this time. I went to town on them and her lady parts. As usual I did my best to make sure she was satisfied. Damn this girl is horny as all get out. She never seems to get enough and I can barely keep up with her. Going to have to work on my stamina. After going through a few condoms we just lay there sweaty and tangled up in the bedsheets.
“Are you really 19?” I asked.
“Yeah.”
“So you like older guys?”
She laughed. “Obviously.”
Goddamn though… where the hell was this when I was in college? I guess I’m making up for it now. And this certainly makes up for the nonsense with #68. This time she stayed the night, much to my delight. I woke up with her arms and legs wrapped around me and her hands stroking my member. She did it with such a soft touch that it was driving me crazy, and it wasn’t long before I was inside her again, picking up where we’d left off the night before. She hooked her arms under mine and grabbed my back and my ass as I pounded her, whimpering into my ear how good it felt.
Needless to say I didn’t last long after that.
College Girl is not one for conversation. Like… at all, unless it’s to tell me to go harder and faster. Either she’s determined to keep things strictly sexual, or she’s just really shy otherwise. Once you get her behind closed doors, though, she’s a wild animal. Tinder really came through for me this time, after having had zero luck in the past. Now we’re working on setting up Round 3, hopefully within the next few days.
The anticipation is killing me…
Friends With Benefits
I made it until the day after New Years before I downloaded Bumble again. I figured… “new year, new me” and all that bullshit, right? After two weeks I’d racked up 125+ matches and landed my first date of 2020.
#66
She was 38 and lived a good distance away so we chose a halfway point – a bar where I’ve met a few other online dates over the years. I keep swearing off bars but it was a Wednesday so I figured it wouldn’t be that crowded or noisy. The bar stools were occupied by douchey-looking guys who looked as if they rolled off an assembly line. And the music was loud, but we grabbed a table near a corner where it was somewhat quieter. We had fun comparing dating stories and such, but I wasn’t feeling anything towards her. Then she disclosed that she had a kid. Ugh, another undercover single mother. That explained it. So that’s another one down.
#67
The next date was with Migraine Girl. She was 29 and suffered chronic daily migraines and we had to reschedule a couple of times because of them. She lives right by the farm I work at and we finally met up for lunch one Sunday. However she warned me that she was getting another migraine so she might have to cut things short. I couldn’t tell if she was acting a bit “meh” because of me or the migraines (or both), but when I asked about a second date the next day I got: “aw thanks. You were very nice but I just didn’t feel a romantic vibe.”
Fuck this.
I downloaded Tinder right after that. I’d tried Tinder once upon a time but it was a ghost town of activity. Maybe it would be different this time. And this time I was looking for a FWB. I’d flirted with that once before but this was for real. I was getting fed up with regular dating and I’ve been horny AF, so I felt like it was time to try something different.
I got a shitload of matches. Dozens and dozens, and after a week I decided “what the hell” and paid for unlimited swipes. There were also 75 outstanding likes and now I could see who they were. Most were duds and a few were fake accounts, but I seemingly hit paydirt with this one chick.
#68
She was down for a FWB thing and we exchanged numbers pretty quickly. She sent me some body shots – nothing scandalous or revealing – but I could see her nipples poking through her shirt in a couple. Hot damn.
Long story short she suggested I come over to her place that night. You know, watch a movie, “kiss me first and get that out of the way… and see what happens.” She flooded my phone with winking emojis and questions about what I liked sexually. I was a bit leery and suspicious that she was okay with a complete stranger coming over to her place without meeting somewhere neutral first. “My driveway is pretty neutral,” she joked. Um, okay then. As usual my dick won out in the end and I headed over.
I texted her from her driveway that I had arrived and would meet her at the front door. “Okay, I’ll be right down!” Then I waited outside for ten minutes. What the hell… Finally she opened the door, and I had wild ideas that after all that waiting she’d be answering in a see-through negligee or something. Instead she was dressed in layers, even sporting a scarf. Interesting. Thankfully she looked just like her pictures. She didn’t have her age on her Tinder profile but I estimated it was the same as mine.
We chit chatted as she led me to the living room couch. I was wondering how to approach this but we just sat down continuing our conversation. She was full of awkward energy and giving off a weird vibe. She put on the movie Green Book, put her feet up on the coffee table and clasped her hands between her legs. We sat there watching for a bit and I wondered whether she was waiting for me to make a move. Eventually I put my arm around her but she didn’t react whatsoever. Thought she might lean her head against me, or cuddle into me… nothing. Didn’t even so much as glance at me, not even when I took one of her limp hands in mine.
Finally I went in for the kiss (as she had earlier suggested) but she leaned back as far away from me as she could, her eyes huge. No, she wasn’t ready yet, she said. Oof. Awkward as fuck moment. I sat back up, my face burning. What was going on here? My mind worked furiously as we continued watching the movie in silence. So I just came right out and asked her: Was she not feeling me? Was she having a change of heart about the FWB thing? Both? She hemmed and hawed and fessed up that this was her first time having a guy over that she hadn’t met previously, and she acts differently when she thinks she might like someone. And the whole time she was talking she didn’t even make eye contact, just stared at the blank wall over the TV. And I mean blank – there was literally nothing on any of the walls and nary a stick of furniture in her house. The place was barren.
When the movie was over she stretched her arms and said she had to go to bed. Alone? Yup. All righty then. I gathered my stuff and she walked me to the front door. She asked if I wanted to have another movie night sometime, and I shrugged and said sure – thinking in the back of my mind “maybe there’ll be sex next time.” Either she didn’t mean it or that was the wrong answer, because she unmatched with me on Tinder by the time I got back home. I already knew there wasn’t going to be a next time. Thus concluded one of the weirdest encounters I’ve had. Not in the Top Five but definitely in the Top Ten. Strange shit.
#69
I made sure to confirm with this one that she knew I was looking for something casual. For all the griping I see about men not reading women’s profiles, I can’t tell you how often I’ve been balls deep in a conversation only to get an “oh wait, I just looked at your profile – I didn’t realize that you were looking for a FWB.” But this one was on board, so all that was left was to meet and see how we hit it off. She was a cute little 29yo blondie and we met at the local brewery. We’ve never been there before and it was a pretty cool place (note to self for future dates). However she didn’t seem that interested in me. I guess my looks were not enough to overcome my personality… or vice versa. Damn. I suggested the ol’ “come over and watch a movie” and left the ball in her court, but it’s been a week and a half without hearing from her. We’re still matched on Tinder but… it looks like the end of the line.
#70
This one lived a little ways away from me but I was in the area and we met for an afternoon of coffee and cards. She was 28 and better looking than her pictures. I was digging her but wasn’t sure if she was digging me. Finally I asked if she was okay with the FWB thing, because this was feeling more like a regular date than anything. “I’m not actually sure I’m looking for that right now. I thought I’d be okay with it, but some things have changed and now I’m not sure I want to do that.” Jesus Christ. But she had fun and thanked me for a great time, and that was that.
I was started to get a little fed up again, but then things changed in a way I never expected…
(to be continued)
The Virgin Mary
I gave it a month after my breakup before I re-downloaded Bumble. I noticed a couple of changes. First, they no longer show when someone’s read your message. Second, they have swiping limits now. I hit them during my first few days on the app, but haven’t since. Anyway, I picked up a bunch of matches, albeit at a slightly slower pace than during my last few stints on Bumble.
#63
I thought I hit paydirt with this one. 31, Lived only a few miles away, didn’t want kids, cute as hell, and the conversation was fire. She was willing to meet sooner rather than later, so we set a date at a craft brewery the following night. Things seemed off from the get-go. As soon as I showed up she was low-energy and a bit meh. I did my best but things didn’t flow like they did online. This has happened to me quite a few times and it’s frustrating as hell. It’s even more frustrating when you feel like the only one making an effort. I’ve literally made up index cards of questions and topics in the past and studied them beforehand in case things lagged. I didn’t do that this time but – social media ninja that I am – I’d found her on Facebook and combed through her interests. Even working some of those into the conversation didn’t breathe more life into the proceedings. The last straw was when she picked up her phone for the tenth time and it looked like she was messaging someone on Bumble. Okay. I downed the rest of my drink and told her good night.
#64
This one definitely went better than the last. 29, also lived a few miles away, also didn’t want kids (woohoo!), but her pictures were a tiny bit suspect. We met at a bar, and I warmed up to her over the course of the evening. For once the in-person banter matched the online banter. We traded stories back and forth, compared dating experiences, talked about our crazy families. We sat at the bar stools with our legs touching, and I was going to go in for the kiss afterwards but I got the cheek instead. Oof. Okay. The next day I texted her to reiterate what a nice time I had, and she concurred. I dithered about, wondering if I should ask for a second date. In the end I took my indecision as a sign and just left it at that.
#65
Finally! A great first date and an even better second date. The two best dates I’ve had in a long, long time. Unfortunately there won’t be a third…
She was 28, lived a little further away, cute as hell, but unfortunately wanted kids. That came up pretty early in our online conversation, and I warned her that I didn’t and that wasn’t going to change. So if that wasn’t going to work for her, I’d understand. Nevertheless she persisted, but I knew this was going to have a short shelf life. That’s okay, though – I’m open to short-term dating.
Our first date was at a board game cafe, which worked out perfectly because she loves board games and hosts regular game nights. We were there for three and a half hours. Afterwards we waited outside for her Uber and I put my arms around her to keep her warm. “You know, we have time for one more thing…” I said.
“What’s that?” she asked, grinning up at me. I leaned down to kiss her in response. It was a bit awkward with the height difference, but it was still really nice. We made out in the shelter of a doorway for a minute until her ride pulled up, and I skipped across the intersection as she pulled away. Now that was more like it! Finally, a great first date. There was definitely going to be a second. It was a week and a half before she had another free night, during which the anticipation was killing me.
This time we went to an Italian restaurant, putting away the food and wine for three hours. Instead of calling another Uber, I offered to drive her home and she accepted. Five minutes in and she brought up the whole not-having-kids issue again. “I hate to be a debbie downer…” she began. She’s looking to get married and have kids as soon as possible, and if I was dead-set on no kids… but she really liked me and was confused as to what do. Maybe we could just date casually? I said I was open to that, yet she was still uncertain.
By this time we were back at her house. I pulled into the driveway and we sat there continuing our discussion. She was all in a dither about things. We interrupted our chat for another makeout sesh. This one was pretty hot and heavy. She tilted her seat back and pulled me over to her side so I could get on top of her. I lost track of the time but we must have been at it for a half-hour. She even let me feel her up and – after I confided being driven crazy by her low-cut shirt on our first date – she hiked her sweater up so I could pull her tits out of her bra for a better look. They were awesome.
Then she dropped another bomb. She was a virgin. Well, I can relate to being a virgin at 29. I even like the idea of being someone’s first. But she told me she was a “good Catholic girl” and saving herself for marriage. OMGWHAT? So if we were to date casually, there wouldn’t even be sex. Wtf would we be doing then? I knew she was politically conservative (itself a potential issue down the road), but to be sexually conservative as well? Yeah, this wasn’t going to work at all. So long story short we parted ways. Sucks because we got on so well and really liked each other.
So that’s the latest. If nothing else I got some kissing and titty action. Now if I could just find someone like her who’s also a huge slut…
Just wondering – should I bring back the date counter? What do y’all think?
So… I Had a Girlfriend
It’s been a while. The last time I was here, I had a handful of Hinge matches that weren’t really doing anything for me. I decided to junk the app. However, one of the girls I was talking to noticed I was gone and panicked. She messaged me on Instagram (slid into my DMs, as the kids say) and was suddenly a lot more conversational. Well, this was more like it! We went on our first date a few days later.
#62
Dawn, 28, a teacher and a local! She lived only a few miles away, and coincidentally on a road I frequently traverse. We met a local pub halfway between our houses. I normally detest meeting in bars and such, but it was a Monday and mercifully quiet. We got on pretty well, and as I walked her to her car afterwards I saw it was conveniently parked right next to mine. I took that as a good sign.
We stood there for a moment looking at each other before she giggled and said, “I always get awkward at this part, I never know what to do!”
“I do,” I said and I took her in my arms and kissed her. We made out for several minutes, ignoring the soft light rain that had developed. She told me I was good kisser, and she wasn’t afraid to use her teeth and bite my lips a little. Ooh, a biter! Does that mean she liked it rough? The thought got me super hard. There was definitely going to be a second date.
We went to a mac and cheese place for our second date, and across the street for brews and board games afterwards. However it was chilly inside and rainy and damp outside – much like our first date – so I suggested going back to my place where it was warmer. I worried she might take it the wrong way and question my intentions. Fortunately she was down for it, and we watched a movie and had a makeout session afterwards. But we didn’t go further than second base. It was only the second date and she didn’t want to rush things.
Third date was lunch and a hike, fourth date was dinner, and fifth date was dinner at my place. I’d always wanted to cook dinner for someone and I finally got my chance. I thought she might stay the night but she left at 11:30. Before she left there was some making out, some clothes came off, and my dick went into her mouth. I couldn’t cum though. I very nearly did, but I got some weird mental block and just couldn’t bring myself to do it. What the hell. And still no sex because now she was on her period. Didn’t bother me but apparently some women are icky about that sort of thing.
Sixth date was pizza and board games, again at my place. She brought her Chrome firestick and we watched the Zac Efron Ted Bundy movie on Netflix. It was very good. Afterwards we cuddled and kissed a little bit, but I held back because I didn’t want to get too worked up and develop blue balls. She was still spotting from her epically long period (her gyno said it was due to her switching birth control pills), but eventually I said “fuck it” and starting making out with her for real.
Eventually she kissed her way down and gave me a blowjob. This time I came in her mouth, and she swallowed. Holy fucking shit. It felt amazing and took me a while to recover from that. She was the second girl to ever go down on me and the first to go all the way with it. Definitely worth the 34-year wait. This girl was definitely a keeper. Even better, I awoke to the good news that her period seemed to be over! Did I want to try having sex? Pfft. You don’t have to ask me twice. I grabbed a condom and when it was over I had filled that thing to near bursting. Phew.
Over the next few months we had some great sex. I lost count of the number of times we did it, but it was certainly in the dozens. She had the most voracious appetite of anyone yet. One night she came over to my place wearing nothing but a trenchcoat over some sexy lingerie. That was one of my hottest encounters ever. We even experimented with paddles, handcuffs and blindfolds – more bucket list items for me. There was good orgasm equality and we often climaxed simultaneously or close to it. I scored some more blowjobs and happily returned the favor. Dawn was only the second chick to ever let me go down on her, so it was nice to get some more practice.
Dawn helped me cross a lot of firsts off my list. I finally had someone to introduce to family and friends. I went on my first ever double date. I updated my Facebook to “in a relationship.” She joined me in the gym and we worked out together. We watched a fireworks display. I posted my first ever #wcw. And then just regular couples stuff I’ve long relished the chance to do. It was so nice to have someone to talk and text with all the time, sharing every weird or random thought. Sometimes I’d wake up and just watch her sleeping next to me, scarcely daring to believe my luck.
So what happened? Everything was going great as we approached the five-month mark, until I got the dreaded “we have to talk.” Turns out… she did want kids after all. In the beginning she said she didn’t want kids, but ended up changing her mind. I was afraid that was going to happen. She was a Pre-K teacher, and anyone who teaches kids likes kids, and anyone who likes kids usually wants kids. And if they want kids, then they have no future with me. Dawn was looking towards the future, so that put the kibosh on things. At least that was the reason she gave. I have no reason not to believe her, so I’ll accept that.
In the end I was dumped but at least we parted ways amicably and I have nothing but happy memories. I gave the relationship everything I had. Nothing was left undone or unsaid and I have no regrets. Disappointing to say the least, when she checked off so many boxes for me. And five months – that’s a new record for me.
All the girls I’ve had success with were fellow Sagittarius. I don’t put much stock in that sort of thing, but it’s funny how it’s happened that way. We certainly had a lot in common. Dawn was a brunette, which is also in keeping with the pattern…even if she did go blonde for the summer. They’ve also been trending younger: 39, 37, then 34, and now 28. Younger seems to be better in my experience. More fun and spontaneity, less baggage, and greater sexual energy and openness.
While I’m sad that my time with Dawn has come to an end, I’m also kind of excited to see what’s next. But I don’t know if I could go back to online dating. (Of course, I keep saying that…) Even with that as a tool, it takes an average of 1-2 years to find someone interested in me in return, expending a great deal of time and energy in the process. We’ll see.
Hinge
Well that didn’t last long. I was feeling certain urges, and since I’d heard talk of it I figured I’d try Hinge. I’m only a few days in and so far I’m not a fan. As the tagline says, there’s no swiping here. You fill in your stats, post a half-dozen pictures, and choose three questions to answer. The questions are things like: “Worst fad I ever participated in,” “A fact people are surprised to learn about me,” “My ideal first date is” or “I’ll fall for you if” etc. When someone likes your picture or answer, you can then message with them.
Unfortunately there’s no About Me and most people’s answers are generic and uninspiring. So while I come across many I find attractive, ultimately I have nothing to say to them. I need more to work with than basic pictures and “I like to have fun and laugh.” I’m also seeing many of the same faces from Bumble. Some of them I’ve even seen since I started online dating, which was several years ago. At least I’m not the only unlucky one out there.
But if you dig long enough you find a couple of prospects. I ended up with six, and I met one tonight.
#61
She lived only a few miles away so I picked out a wine bar at a nice halfway point. I had a seat at the corner of the bar and thumbed through the drink menu while I waited. She walked in a few minutes after I arrived and she looked just like her pictures. Nice. After we got our drinks I led her to a table in the back where it was a little quieter and more private.
We talked for an hour and a half, but despite asking about her family, her job, her life goals, her gym routine, and whatever else I could think of… I can count on one hand the number of times she asked me anything at all about myself. I even left a number of gaps in the conversation to give her an opportunity to do so. Instead I had to keep volunteering information. I realized this about halfway through, after which it started to annoy me.
Finally at 10 I announced that we should get going because they were closing (which they were). We walked outside and she lingered there. I wondered for a wild second whether she wanted me to kiss her, but I doubted that. I hadn’t gotten any sense at all that she was interested in me. So I just gave her a hug, said nice to meet you, and trotted off. I said nothing about meeting again. And that was that.
So. Online dating. Same shit, different day. I still have five other prospects, but there’s only one other serious contender and that conversation is rather one-sided too. No reason to expect things to be any different in person. It’s just really hard to find someone I click with and where the banter is fire. Like I said in a previous post, it’s 1 out of 100 matches. I’ll give Hinge another week, by which point I’ll likely delete that too.
In other news, if you haven’t seen my previous post I’m doing an Ask Me Anything. If there’s anything you ever wondered about me, head over there and drop me line. I may collect all the questions and answers into a future post. And if you want to participate, please comment on that post instead of this one. That way it’s easier for me to keep track of all the Q&As.
Ask Me Anything
….Literally anything in the comments below, and I’ll be happy to answer all your burning questions. I want to try something fun and different here.
