This story happened on New Year’s 2015/2016. I was 30 at the time, and a couple months earlier had gone through a really brutal breakup with a girlfriend of five years. Jump ahead to *** to skip to the action.
My first date post-breakup was with H. She was 32 and very slim and tall, about 6’0” or 6’1”. She had delicate features, pale skin, and wavy dark brown (almost black) hair down slightly past her shoulders. Kind of similar physique to me, actually — I’m 6’3”, skinny, messy brown hair and geeky glasses.
H and I had gone on 2 dates in December. Both times we went to a bar, had a few cocktails and joked around. She was funny and we had a good laugh, but nothing happened beyond that. We didn’t kiss, and I don’t think we even hugged after those first couple dates. We bantered a lot, but it was more friendly than flirty, and our rapport wasn’t particularly sexual, as far as I could tell. I liked her and I could tell she enjoyed my company, but I wasn’t sure if she saw me as just a friend or if she wanted more.
Flash forward to NYE. We haven’t seen each other in a few days. I assume we will be going out again at some point, but we haven’t made any plans yet. We’ve texted a bit back and forth, and she’s already told me that she’s got plans to go to a party that night.
I get quite drunk, and, throughout the night, we send a couple texts back and forth, just talking about how we’re bored and making fun of the different parties we’re at. At 1:12 a.m., she sends a text that says, “Are you still in a partying way? We could could join forces if you are not sooo tired.”
*(Fact check: the snippets of dialogue I have included in this story are obviously approximate, since this happened five years ago. I still have the record of our text conversation, however, so those quotes and timestamps are exact. I looked it up when writing this, so even the typo of “could could” is exactly what she wrote.)*
I tell her I’m going to call her, and she texts back back “Do it.” I step out of my party and give her a ring. “I have some friends throwing a house party on your side of town,” I tell her. “They do it every year and it goes pretty late. I could walk over there and meet you?”
“Yeah totally!” she responds, sounding excited. At this point, I already know something might happen tonight. Even though our prior meet-ups hadn’t been hot and heavy, why else ask to hang out with the person you’ve been on two dates with at 1 a.m. on NYE, right?!
It’s almost 2 a.m. by the time we finally meet up, and once we get into the party, I can see quite quickly that I’ve misjudged things because the party is already winding down. We have a couple drinks there and we’re having fun, but one of the hosts doesn’t seem too happy that I showed up unannounced at 2 a.m. (The host was also friends with my recent ex, so maybe it was weird that I brought someone new with me.)
“We should probably leave,” I tell H, and we throw on our jackets and go outside. As soon as we get to the sidewalk, we instantly start making out heavily, our arms wrapped around each other. I honestly don’t know who initiated it — I’m pretty sure she did, since I certainly didn’t make a move, but we just kind of fell into it spontaneously. After a minute or two of kissing outside of the house, she says, “I’ve been wanting to do that ever since we met.” Same!
“You live near here, right? Can I walk you home?” I ask, and she agrees. We head off, holding hands. It should have only taken us about 10 minutes, but we get kind of lost on the way (we’re drunk, after all), and we stop a couple of times to make out. At one point I have her on the hood of a car, and we we’re groping each other over our clothes even though it’s freezing cold.
Once we finally stumble up to the front of her building, we start saying an awkward good-night. I’m hoping she will invite me up, but when she doesn’t, I ever-so-delicately suggest it myself. “My roommates are home and probably asleep, and I didn’t planning on bringing some dude home tonight. But if we’re quiet, sure,” she decides. Some dude!? Is that what you think of me? Ah who am I kidding, sounds great to me!
So we go upstairs and we we’re whispering because the apartment is dark and her roommates are clearly asleep. She shows me around the dark apartment a bit and makes a self-deprecating joke about how messy it is. There was some shelf reorganizing going on, and there are piles of books everywhere. Like she said, she didn’t plan on bringing anyone back that night.
***
We get into her room, she flips on the overhead light, and we immediately fall onto her bed, making out and ripping off clothes. I was kind of surprised to find out that, despite her being dressed in fairly modest jeans and a long-sleeve shirt that night, her panties are kind of sexy — purplish “boy shorts” that show the bottom half of her butt and have a slight lacy frill. She reaches back to unclasp her bra, revealing perfect perky tits. She’s got perfect, average-sized pink nipples and upturned B-cups. Not that 32 is old at all, but these tits are particularly perky for someone in her 30s.
After spending a good long while sucking her tits, lightly biting and passionately circling her nipples with my tongue, I peel off her parties to reveal her trimmed-super-short pubes and already wet pussy. Like I said, I hadn’t gotten a super sexual vibe from her on our dates, so I’m excited to see that she’s very well-groomed. I dive in for a taste and, after a couple minutes of quiet gasps and moans, she fumbles with my belt and takes my cock into her mouth.
We’re both completely naked and I’m lying on my back while she sucks me. She moves up my body and kisses me, and I ask if she has a condom. (I don’t have one with me because I hadn’t planned on going home with anyone either.) She grabs one for me and lays back with her knees up; I put it on, get between her legs, and she moans softly as I slide inside her in one thrust. My dick’s a pretty normal size — more than 6”, less than 7” — and she takes me all the way to the balls.
We flip over and she rides me, at which point I realize how brightly lit the room is thanks to the overhead light right above the bed. But I’m not complaining, since it gives me a great view of those perky tits as she bounces up and down on me, her eyes closed, head titled a bit back, and mouth slightly open in an “O” of pleasure. She has a move where she’s riding my dick, reaches back behind her butt and plays with my balls at the same time as fucking me. To be honest, my balls aren’t all that sensitive, but it’s hot to have her playing with them and giving me pleasure. I’ve never had anyone do that particular move before or since — I’m guessing she had a past partner who was into it.
Following a little doggy style, which gives me a great look at her toned ass, I flip her onto her back and go down for a little more pussy eating. Eventually, I lay back, exhausted.
By this point, it’s like 5 a.m., the alcohol is beginning to wear off, and I’m a little spent. With all the drinking, I figure that cumming probably isn’t on the cards for me tonight, which is fine. We cuddle a bit and, even though she doesn’t say anything, she clearly wants me to cum. Just when I think we’ve wrapped things up, she slides down my body and, once again, takes my dick into her mouth. She’s bobbing up and down harder and harder, sucking the head and swirling her tongue while she jerks the base of my cock and milks me into her mouth. After a few minutes of pretty intense oral, I groan and reach down to lightly touch her shoulder. “Mmm I’m going to cum,” I moan, wondering if her roommates are in the next room listening to every word.
She doesn’t skip a beat and my back arches, my cock twitches, I blow a huge load into her mouth. She promptly swallows every drop. The sensation of her lips wrapped around my shaft is super intense; I often take a long time to cum from oral, but when I do, I cum like a rocket, and this time is no exception.
She looks up at me from next to my dick, smiles devilishly and says, “It’s true, then — vegetarians’ cum really does taste better.” Hell yeah.
After that I have to leave because my dog is waiting for me at home, probably wondering where I am. It was almost light out by the time I got home, and I got maybe an hour’s sleep before the dog needed a walk. I felt like trash, but I still went for a polar bear swim in the cold ocean that day. Happy fucking new year!
Source: reddit.com/r/gonewildstories/comments/kxh74n/my_hot_nye_hookup_after_getting_out_of_a_longterm