Quick story about the first time we had sex. When we met, we’d initially just started out as friends, first exchanging a few emails and texts then meeting for coffee at the shop a block away from my place to talk on Sunday mornings when we were both free. We’d flirt a little and had had a couple of lunches but nothing that seemed like it was going to lead anywhere, just general chat about life and career, she felt that oral and intercourse should be for monogamous relationships. I wasn’t down with that, so we were “just friends”.
Background is that she had divorced an idiot she married young and was trying to figure out how to enjoy life after a traditional and conservative upbringing in a Catholic schoolgirl uniform, but wasn’t really loving her options. She could see that I was having a good time being single she liked bouncing ideas about life off of me, but mostly she was stuck with two pseudo-boyfriends who were in a hurry to get married. One was a dull ex she’d had to give the “let’s see other people” talk but who was still trying to lock her down, who she’d mainly kept around for occasional sex. The other guy was aggressively interested but they weren’t really on “dates”, and she didn’t know what to think and kept it to making out and heavy petting. There were some real dates with others here and there, but having only had a few partners, she was against racking up numbers.
One day, we meet for coffee on Sunday morning and she’s visibly troubled. She’d done something that made her feel gross: two different men in the same weekend. She was horrified, but personally, I was amused and thought it sounded like she was finally coming out of her shell, and started asking some probing “what were you wearing”-type questions as I drank my coffee.
She’d had a second date with a new guy scheduled Friday night. She’d thought it might be something fun in the long run and had dressed up, but for whatever reason, he started acting like an asshole when he picked her up. They barely got a block away before he made some snide remark about her shiny purse, which she loved, and she just got out at the stop light and walked home, then microwaved her own dinner. While she was eating, she got a message from the guy she’d been seeing asking if she was free to meet for a drink. She was already fixed up, so decided to go along with it, because she was pissed and wanted to do something to calm down.
He’d probably read her being fixed up as dressing up for him, and one drink turned into three, then she ended up giving him head while he drove her home. She kept her dress on, but he got his hands down her bra and got a good feel while she worked. She loves having her nipples played with and ended up touching herself while he teased them, then finished him in her mouth in the driveway and swallowed. They kissed goodnight and she went upstairs to get undressed and wear out her Magic Wand.
The next morning, she woke up, and realized she was supposed to hang out to have dinner with her ex-boyfriend at his house. She was tempted to cancel but over went anyway, and ended up on all fours in his bed, getting fucked doggy-style.
She hadn’t had a cock inside her since she’d seen him two weeks before, and was happy to get it, but there was no chemistry there and she was really bothered that she was now, in her view, having sex with two men at the same time.
That was when I had to break it down for her: that was a pretty typical weekend for me, and she’d done nothing wrong. It was two different days, she hadn’t promised either of them anything, and she used a condom.
I could tell she was surprised that I wasn’t taking this seriously like she was. Her Old World immigrant parents would have lost their minds. When I explained that I’d once been with three women without even taking a nap between them, and that one of them knew about the other two and didn’t care, she actually seemed relieved. Thank God, no judgment.
On the way out, she gave me her usual kiss on the cheek, then lingered a little bit, and I gave her a quick kiss on the lips. It startled her but after we parted ways, she texted me.
“don’t ever change :)”
A few hours later, I texted her back that there was a dive bar playing live music from a good band I knew, I was going to be hanging out, and that she ought to stop by. Sure enough, she found me, we shared a table, and after a couple of drinks I start feeling her up under her skirt. We had a heavy makeout session in the back of her car under a streetlight in the fast food parking lot next door, hands get everywhere and I find out her breasts are just as nice as I thought they were, she strokes my cock inside my pants, then she called a stop and wanted to go home. Just before we parted ways, I suggested we could hang out at her place if she wanted, and she hesitated, then agreed. We went straight upstairs, I got her undressed, she unbuckled my pants, and I got on top of her without a condom. It was stupid but there was no stopping us, then after we made out and cuddled for a while, I was getting dressed to go home and she asked if I could go again.
I wasn’t sure if I could, but she was desperate for it and that was a turn-on, so we went again, in the same position, and I filled her up with a second load before I left her there in bed. That made three different men in three days, which is still a record for her.
We texted daily for a while, and stayed in friends-with-benefits mode, having sex a few times a week with her in my regular rotation. Two weeks later she was supposed to meet the guy she’d blown, and asked me over lunch if I’d be upset if she slept with someone. I told her she can do whatever she wants, but suggested my Saturday night was wide open and she could swing by my place after the date if she wasn’t satisfied. She was horrified but thought I was being funny.
As it turned out, she couldn’t reproduce the moment: she tried to fool around with him after dinner in the restaurant parking lot, but he couldn’t get it up, and in disgust, she dropped by my place. Ended up spending the whole night and getting a parking ticket because she’d missed the “No Parking” sign in the snowfall. This week marks a decade of fun.
Source: reddit.com/r/gonewildstories/comments/akdhmr/wifeys_busiest_weekend_mf_mf_mf
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