So, my next post was supposed to be about politics and dating, and indeed I have several pages of rambling notes I’ve been agonizing over. I’ll get to that post eventually, but I have to write about something else first.
I met someone new. Here’s how it happened:
It all begins with Winery Girl. We still talk on occasion even though she’s had a boyfriend for the past two years. Funnily enough, she actually took his virginity. He had to wait six months to have sex with her though because – as she put it – she’s not a whore. Uh… okay. I wasn’t sure what to say to that.
She’s not too crazy about her boyfriend. He’s basically a seat-filler because she can’t stand the thought of being single again. She’s also been using the BFF function on Bumble to find new female friends. She’s having a hard time of it, since all she sees are girls with nose rings and that’s a huge turn-off. I know that because she’s been griping to me and sending screenshots.
Winery Girl dared me to go back on Bumble to see how many nose ring girls I could find. Ok, why the hell not? I thought it might be funny. And since I was treating the whole thing as a joke, I put in next to no effort. I only posted one (albeit unique) picture and put one sentence in my profile. Within a couple of hours I had nearly 40 matches from my careless swiping. I hid my profile before things got crazier.
I spent the new few days culling the herd. I decided that if I was going to entertain anyone on the app, then they’d better stand out. A good portion expired without a message. Many messaged with nothing more than “hi” or “hey” or “what’s up” so I deleted those. Several messaged me and I responded, only to hear nothing further. I deleted them as well. The remainder matched me in goofiness and witty banter, and Jane was the finalist (no nose ring, btw).
We got on so well that I asked her out, despite my original intention not to ask anyone out. (Yeah yeah, I know…. so much for swearing off online dating.) Our first date was a few days later at a wine and cheese place, and we were as fun and flirty in person as in text. However she had a few more extra pounds than were evident in her photos. Hmm… well, okay. Not enough to be a deal breaker.
It was light and easy and comfortable with her. I could relax and be myself. Still missing that spark from meeting the old-fashioned way, but still better than most other online dates. We spent a good chunk of our first date planning future dates, and we were at the place until closing. I walked her back to her car, which happened to be a few spaces from mine. We stood there talking until the well ran dry and then there was a slightly awkward silence. “I don’t know what happens now,” Jane giggled nervously.
I did. I wrapped her in my arms and kissed her. I didn’t hesitate or wonder if I could or should, I just went for it. I wasn’t even nervous. Big change from when I was going on dates three years ago. She really got into it, too. Almost immediately she was frenching me and running her fingers through my hair, and almost immediately I was super hard.
Our second date was that Saturday. Jane needed help stringing Christmas lights on her tree so I gallantly offered my services. She proclaimed that there would be no sex until at least Date 5 or 6. No problem, I assured her. However, I remembered Rebecca wanting to wait, yet we fucked on Date 2 when we couldn’t control ourselves any longer. So with that in mind I came packing a box of condoms. Just in case.
When I got to Jane’s place I couldn’t help notice the lavish furnishings. She seemed a bit materialistic, which she confirmed by telling me how much she liked to shop. She also told me she liked being spoiled. Fortunately I’d brought a bottle of wine along, but I frowned to myself. I wasn’t going to overthink things, but I couldn’t help imagine our lifestyles clashing down the road. No matter. I decided to not worry about the future and just enjoy the present.
I also couldn’t help but wonder whether Jane wanted kids…? It never came up in conversation, and she was already 38. In fact she was a year younger than Rebecca was. Hmm. 39, 38… for some reason older women seem to be the only ones I’ve been having any real success with. Interesting. I do seem to connect better with those a few years older. And I do find them appealing in a way. That is, as long as they’re child-free.
We ate take-out and then I helped her put the lights on the tree. Unfortunately, while the boxes were labeled the same, the two strings of lights didn’t match. Dammit. We sat on the couch gazing upon her half-and-half tree. Then we snuggled together to watch the rest of The Santa Clause on TV. That didn’t last long. I’d been there for over an hour, and I was running out of self-control.
I reached over, cupped her chin in my hand, and tilted her face up to meet mine. A heavy make-out session ensued. God, it felt so good to do that again. First time in a year and a half. Before long I was sprawled on top of her. After a while of grabbing at the hem she finally pulled my shirt over my head. Yes! This was happening! Once it was off I asked whether she wanted to move things to the bedroom. At the very least it would be more comfortable than the couch.
“We’re not having sex, but we can do other stuff,” she said. I assumed “other stuff” meant oral. Who’s the lucky boy? I thought to myself. I’d never gotten a BJ to completion before, so it sounded like it might be a good night! We resumed making out with some ferocity, and eventually my hands made their way to her chest. I hesitated a bit, wondering whether she’d let me cup her breasts through her shirt. She did. Yes! Her shirt came off shortly afterwards, followed by her bra.
I’ve fantasized about it many times, but actually removing a girl’s shirt and bra is truly a magical experience. I don’t think it’ll ever lose its luster. I relished the skin-to-skin contact, spending eons with my mouth on her neck and tits. I started inching my way down, sucking and kissing and licking and nibbling as I went. As I approached her belly button, I wondered how much further I could go. No girl had ever let me go down on her before.
One time with Rebecca, I’d barely started on her when she pulled the blankets around her and proclaimed she was cold. I guess that meant we were done? After that, anytime my face ventured too far south she’d stop me and tell me she wanted me inside her. Wasn’t going to argue with that. Plus, I figured that like a lot of women she was self-conscious about how she looked or smelled or tasted down there, although she looked tantalizingly perfect.
After a period of time Rebecca told me she wanted me to go down on her, and I said I’d be happy to oblige. I sent her descriptive texts about how I wanted to put my head between her legs. Unfortunately that was also around the time she started getting weird and told me she was feeling overwhelmed and needed space. Who knows whether my texts contributed to that, but in any case I approached Jane’s nether regions with caution.
I hooked my fingers in the hem of her pants and pulled them down. Her panties came with them, and she assisted me in pushing them off. Then I started to tease her. I worked my mouth along her inner thighs, first one leg and then the other as her breathing intensified. I kept teasing her until finally I was face-to-vagina. My mouth hovered over her lips as I waited for the red light, but she didn’t seem like she was going to stop me. She was naked and waiting.
So I took the plunge. I went all-out, working my tongue in and out and all around. I kept that up for a while, occasionally coming up for air and another mini-makeout session before going downtown again. This time I stuck my tongue in even deeper, sucking on her clit while working my fingers inside her, trying to remember everything I’d ever seen or read. Her moans and cries grew louder and louder and I smiled at her reactions.
Suddenly I felt a wave of heat as her body shuddered, and she wrapped her legs around my head and nearly yanked my hair out as she came. Wow. That was intense. I made her cum two more times like that before I stopped. I’d been at it for at least a half-hour and I needed a break. My mouth was parched. She held me tight to her chest and I enjoyed being suffocated by her 36Ds (I’d peeked at the label when I took her bra off).
“You’re bad,” she said. “You’re not as innocent as you look.”
I gave her an evil grin. “Definitely not,” I said.
“I didn’t think we were going to do all that…”
“I didn’t so either,” I said, laughing a little.
“What’s so funny?”
“Can I tell you a secret?” I asked, then immediately debated whether I should. Ah, why the fuck not. I wanted to see her reaction.
“You’re actually the first person I’ve gone down on…”
There was a pause. “What do you mean??”
I told her I meant just that. She actually sat up and made me look her in the face as I said it again, because she wanted to make sure I wasn’t lying. Then she goggled at me.
“But… like… how did you know how to do all that?” she sputtered, astonished. “YouTube?”
“Google,” I grinned. “Was it really that good?”
“Yeah,” she said, sinking back into the couch again. “I’m still trying to catch my breath.”
“Well, I’m sure there’s room for improvement.”
“Well, you can practice as much as you want on me,” she said with a kiss. And then I revealed a little more of my history to her, which further shocked her. She couldn’t believe that not only was she the first I’d given head to, but only the second I’d been intimate with. “So I’m your first vagina…” she said dreamily.
However, I was getting the sense that she wasn’t going to reciprocate, and I was right. Dammit. While disappointed, I didn’t whine or complain or make her do anything she didn’t want to. Instead I was just glad I’d had my first opportunity to give oral and I did my best to make it count. And I quite liked it. I wanted to do it again. And I would have gone down on her again had my tongue not felt like sandpaper at that point.
By then we were halfway through The Santa Clause 2 (a sequel which did NOT need to be made). We cuddled on the couch for a while before moving to the bedroom, but only to sleep. I’d already figured on staying the night, especially since it was snowing and the roads were treacherous. She put on her PJs and I stripped to my boxers. It didn’t take long before we were fooling around again. We were spooning when she told me I could hold onto her breasts. No problem!
Her shirt came off once more and I went to town, especially after she told me she likes her nipples pinched and sucked, which I was more than happy to do. Then I sat against the headboard and told her to lean back against me. That way I had a great view and easy access to her tits, and I fondled them to my heart’s content. Finally I ended up lying on top, grinding myself against her. She bucked her hips against me in return, and went harder and faster until she came one last time.
Jane assumed I came too after I rolled off her, and was astonished to hear I hadn’t. Yeah… dry humping doesn’t do it for me. And her hands never ventured past my waist, true to her word that she wasn’t going to touch me. Which was a shame, because I had the biggest erection ever and would have loved to have shown it off. But getting so worked up for so long was a mistake. I went into the bathroom to whack off, but it was too late. Wham. Blue balls. Jesus that shit is painful.
But I had to relieve myself or else I was going to be wired all night. After that I was able to sleep, and as I drifted off I mused how surreal it was. If somebody had told me two weeks earlier that I’d be in a new girl’s bed, I’d have said that was crazy. Yet there I was, and her bed was comfortable as shit. I didn’t stay for breakfast as I had to get going, but we made plans to meet again during the week.
The following Tuesday we had a bonafide movie night. And I take movie nights very seriously. I actually watch the movie, and I even have my own popcorn machine. She was surprised, but even more so at my choice of movie: Bad Santa. Not only is that one of my annual holiday flicks, but I chose it specifically to test her sense of humor. That is critical to me, and I was having doubts.
Well, she did not find it funny. While I was roaring with laughter, she was going “awww!” every time the kid was onscreen. When it was over I wiped tears from my eyes and relayed the tale of when I saw it in the theater with my mom and brother, and people kept turning to stare at us wondering why we were laughing. “Yeah, I was wondering the same thing,” she said. Um, because it’s a comedy? Yup, as I’d suspected we were definitely a mismatch.
After that we had a quiet time snuggling and chatting. No fooling around, no groping, no making out… I wasn’t getting all worked up again for nothing. If she wanted to wait to get physical, then we were going to wait. Until then I was content with running my fingers through her hair, massaging her head and neck and shoulders… all the while marveling at how amazing it was simply to touch another human being.
Eventually we called it a night and I took her home.
We had a fourth date lined up – a Paint Nite – but there was more goddamn snow and it wrecked our plans. She said she was feeling sick anyway, so that put the kibosh on the next few days too. During that period I noticed our communication dropping off. I was holding up my end but she was getting quieter. My gut told me what was coming. I’ve been down this road a million times. So I waited. Finally the word came down the pike:
“I’m sorry for the late response I have been running non-stop and can’t seem to catch up! I am an idiot for taking up a second job- I have to be at work at 6 am. This is just such a busy time of year etc.. plus holiday, plus my trip, I’m not sure if this is really a great time for me to start a relationship. It’s not fair to you. You are a really nice, sweet, kind of guy and you deserve a girl that has time to give you. And unfortunately I can’t be that girl. I realized all of this today as I finally have a chance to catch my breath and think…”
My suspicions were correct. And it sounded like a polite way of saying, “I’m just not that into you after all.” Which would have been fine, because I was starting to feel that way about her. But I gave her a chance and it was fun while it lasted. So I told her “no worries” and that I understood. Thus concludes my latest dating experience. So while 2017 won’t go out with a bang, at least I got to eat pussy for half an hour and play with tits for another hour. It was a good thing I went down on her when I had the chance, because who knows when I’ll get another one.
Ha – and I still suspect that Bad Santa was the beginning of the end for her. Oh well.