I (then-20F) had a five-month fling with a much older woman (49F) that I still daydream about all the time. She was my first experience with a strap-on. [FF]

I went back and forth on whether to share this or not, since I’ve revealed a lot of personal info already, but I’m gonna go ahead and do it.

So I’ve talked about my friend Samantha before, and going on that visit to her client [where I watched her get spanked](https://www.reddit.com/r/SluttyConfessions/comments/khie8c/you_guys_asked_so_here_it_is_i_never_actually_did/). (So hot!) I mentioned that I actually went down on her about a month after that. That hookup was pretty straightforward… she came over, we watched a movie, drank some box wine, cuddled, started making out, and then she asked if she could go down on me. I’d never had a girl eat my pussy but was incredibly ready to try. She was amazing, and after, I asked if I could do her. My brain basically melted…

But this isn’t about that!

**[The backstory – skip this if you want]**

I started hanging out with a few of Samantha’s friends, and eventually a couple of them invited me to this supper club-type thing at this lady’s house in town. Her name was Kathy. (Changing her name here obviously.) She was some kind of senior administrator at our college. She was 49 and apparently did a lot of mentorship with young women at our school. She held these monthly get-togethers at her house with a group of like 10-15 women from our school where we’d talk about our goals, women’s issues and help support one another over some homemade food and wine. It was really cool.

I was pretty blown away by Kathy. She was gorgeous (blonde, very in shape (she had 3 kids!), green eyes, fashionable dresser) and super kind and comforting, but still firm. Kathy was also married – to a guy. We rarely ever saw him – he mostly kept out of sight. We met all 3 of her kids, though. The oldest was a few years older than me, the youngest was still in high school.

I started trying to dress to impress her when I’d go over there. I knew exactly what to wear to get a guy’s attention… but a girl? Let alone an older woman? I was clueless, and I felt weird asking someone, so I just guessed. (I went with flowy skirt and a blouse that showed a little skin, but not too much.) I sort of developed a girl crush on her. And I guess she noticed…

**[Okay, the good part]**

Before I left one night, Kathy sorta took me aside and asked if I’d like to talk one on one about a thing I’d said earlier. I said I’d love to. She told me to come over the next night, so I did. I fussed over my makeup for an hour before. When I went over to her house, it was just the two of us. None of the other girls were around, and her husband/kids were gone too. She cooked me dinner while we chatted, and somewhere in my second glass of wine, I realized that this was really like a date. She was even flirting with me – touching me a lot – and I was reciprocating in a way we never did at the supper clubs.

After dinner, we were sitting at her kitchen bar with our wine, our knees touching, and she’s sorta stroking my hand with hers. I was so excited but didn’t know what to do. Then, she puts her hand on my thigh and kisses me. I kiss her back, feeling her tongue enter my mouth and moaning a little. Then she asks, *”why don’t you let me go wash your hair?”*

My heart almost exploded. I asked if her husband wouldn’t be home soon, and she said he was out of town, and so was her daughter (the high schooler). We had all the time in the world. So I nodded, and she got up and took my hand and led me back to their master bathroom. She drew a warm bath in his enormous tub, undressed me (with a lot of kissing in between) and then told me to get in while she stripped down too. (She was in REALLY good shape for a woman her age.)

Then, Kathy washed my hair with and used the hand shower to rinse. She sat behind me in the tub, letting me mostly sit back against her. Occasionally she’d lean down to make out with me while fondling my breasts or something. When she was finished, she brought the hand shower down to my pussy. She used it while playing with my nipples or letting me suck her fingers to bring me to this incredibly intense orgasm. One of the best I’ve ever had, honestly… I was writhing and moaning up against her the whole time. I cried out loud enough that her neighbors probably heard.

After that, she got us out of the tub, toweled me off, and asked if I’d ever *”had oral sex with a woman before?”* (I laughed a little when she said it like that.) I said yes and asked to please let me do her, and she did. We went back to their master bedroom and I did the best I could to eat her out. And then she went down on me. I stayed the night there with her, and before she got up to make me breakfast the next morning, we did it again.

*(Sorry, this is getting way too long, it’s just a really vivid memory for me so I have to write it all out)*

AFTER THAT, we saw each other pretty often for the next semester. She and her husband had kind of an “arrangement,” I guess, though I never asked directly and never saw/spoke to him. I sometimes went over to their house in the middle of the day when we knew her daughter was still at school. This only backfired once, when her daughter came home in the middle of the day while Kathy and I were 69ing in their bedroom. If she’d come upstairs, she would’ve definitely seen us together (or at least hear me about to cum). But I think she was just picking something up because she left right away.

Kathy liked to be pretty domme, which was perfect for me. She had this big strap-on that I honestly loved. I’d ask her for it. She sometimes made me suck it first (she said I looked so cute sucking her “cock”) before she’d fuck me in missionary or doggy style. More often, we’d take a bath together and then 69 or give each other oil massages that usually turned into those porn massages you see online. ?? Kathy also made sure I did my homework and kept me in line.

Over that next summer, Kathy got another job at a bigger university out of state, so they moved. I was really sad about it. I’ve seen her three times since then, though, and we’ve gotten together at whatever hotel she’s at…

I don’t think I was Kathy’s first supper club hookup. I’m not even sure if I was the last! But holy christ it was hot. I had only just started fooling around with girls, and getting a full grown woman as my guide was… just incredible. I wish everyone could have the same opportunity. I still daydream about Kathy fucking me pretty often.

Source: reddit.com/r/gonewildstories/comments/kqx3sq/i_then20f_had_a_fivemonth_fling_with_a_much_older