That time I went full-send into an age-gap fling

September 10

This was late June when she liked me on Hinge. I’m tall and traditionally masculine, with a gentle and nurturing side. So I attract girls with daddy issues, and to make a disclaimer right now — I’m very responsible with the hearts of people I sleep around with. I’ve done my time with serial monogamy, and it’s not worth getting into a relationship just for fun. If I think there’s a chance someone will fall and it won’t be reciprocated, I cut it off — as should all of you reading this.

Let’s call her Lucy. Lucy had turned 18 the week before, and she had been really into dom/sub kink and didn’t take long to venture into calling me Daddy. Obviously given the age gap, I was already a little hesitant. Younger women are obviously attractive, but the “barely legal” thing is where it usually gets a little gross. But here this girl was throwing herself at me, and I don’t mean to be crass, but she had some of the biggest tits I had ever seen. Like warm, soft cantaloupes that she was more than forthcoming sending me pictures and videos of. She was otherwise thick but not fat, had long brown hair that was even thicker than mine, and cute hazel eyes.

The first time I met her was just over lunch at a cheap place to meet each other publicly, and she was cute and charming. I could already tell that this was only going to be a short-term thing. She was extremely nervous and smiley, and barely ate anything. Before she got picked up to go home, she asked if she could sit in my car with me for a while. I told her that that’s dangerous and she should be careful offering that to just anyone, but I happily obliged. I took her to the car and started kissing her, and she was a surprisingly good kisser. We took each other’s hair down and started making out more heavily. I put up the car sun shade for more privacy. She tried to suck my dick, but I didn’t let her quite yet. However, I did pull down her panties and give her the first orgasm she’s ever had from fingering (leave it to mediocre ***age boys to make me seem like a sex god). I also gave her the second through sixth orgasm she’s ever had through fingering.

After sending her home, we obviously began plans to see each other again. I took her to the mall and got her a bra from Victoria’s secret with daisies on it, after a literal hour of trying them on, because most of them were too small. Lucy had expressed past trauma from her parents and an ex boyfriend that would make her feel indebted or guilty when they’d buy things for her, so I emphasized: “Me buying you anything by is my choice. You do not owe me anything, not do you owe anyone who buys you something on a date anything ever.” You’d think she was about to cry from happy tears.

We also swung by bath and body works where I got both of us candles and stuff (I like them too), and then we went to the movie. We’d talked previously about using a remote vibrator in public (she’d used many vibrators before), and she was really excited about it, so I revealed the one I’d bought a few days ago and put it in her in the back row of the theater. After about 30 minutes into inside out 2, I’d been teasing her for a good long while, pressing the remote at random times and driving her crazy. The thing gets pretty strong. Eventually, I was worried she was going to scream in pleasure, so I turn the vibrator up and make her cum for what seems like a minute straight, covering her mouth. I make her cum probably a dozen times throughout the movie before she seemed exhausted and I gave her a break. I left the vibrator inside her and gave her the remote and bag it came in.

After that, we’d made plans to see the fireworks show together. I filled a cooler with our favorite snacks, threw it in my SUV, and got some sunshades that covered every window for complete privacy. We set up our fireworks tailgating and laid in the back, kissing and just chilling. We had a tiny bit of weed just to relax, and climbed all the way in and shut the trunk. You’d think my cum was made of solid gold the way Lucy ripped off my shorts and tried to get it from me. She pushed me on my back and impaled her face on my cock, and it wasn’t long before I came down her throat. I ate her out in turn, and lost track of how many times she came. She’s still capable of more orgasms than any girl I’ve ever met.

We made out for a while longer with the engine and A/C still running, and continued to undress as the fireworks went off. I sucked on her tits for a while, kissed her neck, her thighs, her pussy, tasting her everywhere I could. Eventually I pulled her on top of me. She’d gotten her IUD just long enough ago that she could have sex, and we both knew it. I’d just gotten STD tested for this very reason. Lucy was straddling my hips and I teased her pussy with my cock. I don’t exaggerate when I say I felt her juices DRIP down my cock. I did this until she couldn’t take it any longer, because I wanted her to be the one that started it. We made eye contact, both of us teasing one another longer than either of us thought the other would hold out. But finally, she brought her hips down on my cock and we both groaned a sigh of relief. She wasn’t overly tight and it didn’t seem ***ful or anything, but she felt absolutely perfect around me. We just continued to kiss deeply but slowly as I had my arms around her, her on top but me controlling most of the penetration. I can still sounds she made in my mind as we both started to pick up intensity. I held out just long enough for her to cum, and that was my signal to fill her pussy while our tongues intermingled and our hands were all over each other. I’d brought a towel (don’t forget it) that I laid her down on as we continued to kiss more, and we eventually got dressed when traffic started to die down. We put the cooler in the car and I took her home, where she told her mom she had a good time.

I don’t talk with Lucy anymore, mostly since I didn’t want to risk her getting attached, but I still think about her sometimes, and I hope I’ve helped her learn in a positive way.