Making out, fingering, and fucking my way through a break up [MF] [MF] [MF]

If you read my first post then you know how awkward I was in my early 20s. This story happens last year, about a decade later, after another long-term relationship ended. I’d like to think I was a bit more confident and had a lot more fun:

This relationship was one that should’ve ended long before it did, we both hung on, thinking it would eventually work. It didn’t. It ended friendly enough, we don’t talk, I mostly felt relief when she left my apartment for the last time.

And within hours I was swiping on apps: Tinder, Bumble, Hinge, you name it, I tried it. The first month and a half after the break up was fun, I ended up going on a lot of dates, but the three most memorable from that first month are Sally, Anna, Nadine.

**Sally**

48 hours after the break up I fucked Sally. We matched on Tinder and chatted for a few hours, our conversation full of sexual innuendo. Sally was South Asian, short, a little bit of extra weight at 5’3” and around 130lbs, but she was cute and clearly looking to have fun.

She agreed to come hang out at my apartment on a Tuesday afternoon as neither of us had to work. After an hour of listening to music and continuing where we left off in our text messages I asked if she wanted to make out a little.

She smiled. “Sure.”

After a few minutes she broke off the kiss. “You’re good at this, huh?” My trick is go slow, build tension, don’t rush. After making out off and on for 20 minutes I suggested we go lay down. She agreed. We made out for a half hour, our hands exploring each other. I pinched her nipples, kissed her neck. Finally teasing her around her waistband for what felt like forever. She was moaning into my mouth, encouraging me between kisses…so I decided to see how wet she was.

She. Was. Soaked. She was dripping wet. As I explored her pussy, teasing her clit, she stopped kissing me so she could lay back and enjoy. Her eyes were closed as she focused on her building orgasm. But I stopped just short each time, continuing to tease her.

Eventually she started unbuckling my pants, grabbed my cock, looked me in the eye and said the magic words: “I hope you have condoms.”

Sorry to disappoint you: we had boring, uneventful sex, even though the build up and foreplay was fun. We fucked once, mostly in doggy style, and she came hard and I came shortly after. We texted a bit later that day but never met up again.

**Anna**

Anna and I matched on Tinder about a week later and agreed to meet up for wine. She was much more hesitant and playing it safe (smart!) and wanted to meet in public, promising twice that nothing would happen on a first date.

We met at a dark, quiet wine bar on a weeknight. There were a few regulars at the bar, talking about the differences between some malbecs while I ordered two glasses of merlot.

Anna was from Ukraine and had a very slight accent. She was 5’6” with blonde, curly hair. She had a cute face, small tits, and was toned from being a runner. We talked about our jobs, our friends, where we were from. We ended up getting a second glass of wine and continuing our conversation.

When we finished I asked if she wanted one more drink at my place, because I lived nearby, “No pressure though, I totally get it if not!” She thought for a few moments, smiled, and said “I think that would be fun.” I was still not expecting anything to happen since she had assured me nothing would, but maybe we’d make out a little.

We sat down on my couch with some whiskey and continued talking. I turned on some music, she asked about it, we went through some Spotify playlists while sitting shoulder to shoulder, our knees bumping into each other. She kept accidentally touching my leg or my arm, the alcohol probably having some effect but neither of us were drunk.

Eventually I asked, “Is it okay if I kiss you now?” She said, “Hang on.” She grabbed her phone and sent a text—later she said she was just texting her friend that she was okay and I was not a creep. When she put the phone down she leaned in and we were making out instantly, our tongues exploring each other’s mouths.

Before long we were laying on my couch, uncomfortably, but neither of us cared. I tested the waters, grabbing her tits over her sweater, she encouraged me with small moans. I reached under her shirt and played with her nipples, felt her tits, and traced lines down her stomach, teasing her for a while. She kept encouraging me, moaning ever so slightly more as I inched closer to her waist.

Eventually I moved to below her skirt, teasing her inner thighs. She spread her legs, inviting me to continue, and before long I was rubbing her pussy through her pantyhose.

She paused. “Should I just take them off?”

“It’s up to you,” I said with a smile. She tore them off instantly.

I went back to teasing her, but I could tell she was dripping wet, the moisture and heat radiating off of her pussy. I finally let my finger glide over it, she shivered, looking me in the eyes begging me to continue. I slipped one finger into her, ever so slightly finger fucking her, before bringing it to her lips.

She knew what to do, taking my finger in her mouth and tasting herself, she closed her eyes.

I kissed her hard and continued fingering her, alternating between teasing her clit, and finger fucking her. I stopped and mentioned “You’re so wet,” and she said “That’s what happens when someone teases me for 45 minutes straight.”

I finally made her come, her moaning getting loud enough I wondered if neighbors could hear. She relaxed into my couch, me mostly on top of her, and we made out a bit more. She reached for my cock, but I told her, “We have to save something for next time.” Our second date was the next weekend, and that’s a story I’ll write up later.

**Nadine**

Nadine was fun. We matched on Tinder while I was at a bar before a different date and she messaged me first. We chatted a bit and exchanged numbers. And then I get a phone call. I know it’s her, but I ignore it—I’m at a bar, waiting on a date, and I hate talking on the phone.

She texts immediately, “No answer?!” I ask “Who calls someone?!” She explains she always calls people to see if they’re serious about meeting or just messing around. I assure her I’m serious and say I will call her back later.

Nadine is hot. She’s short, has dark olive skin, an adorable face, and clearly has a nice body. Her ass was amazing, her tits were C-cups.

My date ends early, we didn’t click, had one drink, and head out. It probably didn’t help I was imagining fucking Nadine the whole time.

On my walk home I give her a call, it’s only 9:30. She answers excitedly, “Finally!” She had just gotten home from having a couple of beers with co-workers and is clearly a little tipsy. I boldly ask when our first date is and she says “Now? Where should we meet?” I pick a bar that is in the direction I’m walking and conveniently close to my place. She says she’ll grab a Lyft and be there in 30 minutes.

I’m waiting outside as she pulls up, we head into the bar, and it’s nearly empty. We grab drink, sit on a couch, and begin getting to know each other. It turns out we both recently broke up with someone, she travels a lot for work so hasn’t been on tons of dates. Eventually I just ask, “Want to go drink at my place?” She’s enthusiastic, so we begin walking. I reach for her hand, and she happily takes mine.

“I’m not looking to hook up tonight,” she establishes. “Oh, no, me neither,” I say, “but, I mean, making a out a little isn’t a hook up.”

“Oh, yeah, no, making out a little is okay,” she says and smiles at me while we’re waiting for the light to change to cross the street.

We get to my house, walking in the door, she turns around in front of me and we start making out. I grab her ass and she is in to it. I turn her around and press her into the wall, and continue for a bit before slowing down and asking if she wants a drink. She says sure, and we sit on my couch sipping whiskey, talking, and kissing on and off.

As we finish our whiskey the full on making out continues. My hand grazes her neck and she pulls away, moaning. So I ask, “Do you like to be choked?” She leans in to kiss me, breathing “yes” into my mouth. So I push the limits a bit, and each time she moans, getting in to it.

Eventually her shirt is off, my hand is down her pants, and she’s moaning. She eventually reaches for my cock, feeling around my pants, before getting it lose. She holds on to it while we’re making out and since she’s enjoying being submissive I pull away, grab her hair, and ask “Are you going to be good and suck my dick?” The alcohol is helping me be bold.

She nods and I guide her head down. She is giving a great blowjob. But she pauses, turns her head, and looks up at me smiling. I ask, “What do you want?” and she says, “Everything.”

I tell her to take off her clothes and head to my room. She is naked, walking down the hallway, and I am following her. We get to my room and without me even asking she’s on her knees, next to my bed, continuing where she left off. She looks up at me, holding my cock, and says, “I like to be slapped, too,” and so I give her a light smack on the cheek and tell her to get on the bed. She moans as I do and hops up.

I continue to tease her, and she whines, “Please fuck me already,” and so I do. She’s wet, she’s tight, and she is moaning while we fuck and I lightly choke her. She comes quickly while playing with her clit and seeing her come and after the blowjob I follow close behind. We cuddle for a bit, it’s 1am, and she says she has to head home but we should meet up again. And we did. Which is another story.

Source: reddit.com/r/gonewildstories/comments/k9wpiw/making_out_fingering_and_fucking_my_way_through_a