Hello,
This happened a few years ago with a girl (let's call her Livia). We met at a wedding and got along well. She was gorgeous and fun to talk to. I didn't know if she was into me or just a naturally friendly and flirty person and I didn't have the nerve to ask.
We exchanged numbers and started hanging out afterwards. I didn't ask her on a date but we became good friends. At some point, the topic of relationships came up and I told her I was a virgin (despite being 26 at the time). She thought it was hilarious, teased me a bit about it (nothing too mean).
She told me a bit about her dating life. Started off vague, told me she had a couple of BFs back in college but since graduating (she was 23), she had started seeing people casually on dating sites.
I should say at this point, we lived in a very conservative culture where people rarely talk about sex and relationships. So, it was exciting to talk about it, even if vaguely.
We started talking more freely since then. She told me she regretted not sleeping around much in college, so was making up for it now. I actually enjoyed hearing about her flings but tried not to seem too excited because didn't want to be seen as a perv.
Anyway, she texted me one time and asked if I could pick her up for lunch. After college, she'd moved in back with her parents and was taking some time off before getting into work. So, most of the time, I was the only one with money when we hung out, so I'd usually pay her bills when we'd eat out. I didn't mind since I was making good money and liked her company.
So, I drove over to her place, expecting to take her out to a usual lunch but when she came out, I had a jolt run through me! She looked stunning, all made up, with makeup and hair done like I'd never seen on her before.
She looked so gorgeous that I must've stared too long in the car and she started laughing which snapped me out. I was wondering if this was a date but then she asked if it'd be okay if someone else joined us too.
I said sure, but was still wondering if I was now on a date or not. Thought maybe she wanted a friend over in case I was too awkward (I used to be a really shy guy, and was very nervous sitting next to her all made up in the car). I tried making small talk but she was distracted and spent most of the drive on her phone, so I let her be.
Anyway, once we got to the place and seated ourselves in a private booth, she told me that this WAS a date, but not with me. Rather the "someone" (let's call him Paul) who was coming to meet us. I was a bit upset, told her she should've told me about the date.
She apologized and explained that she genuinely hadn't realized she didn't call it a date because she was caught up in texting him. I don't think she was lying btw. She really looked very excited so I believed her (and still do) about forgetting to explain.
Anyway, she told me that it's her first time meeting Paul and she'd feel safer if I could be there. That it'd be a huge favor. I agreed to stay and to drop her back to her place after lunch.
When Paul arrived, he looked annoyed at seeing me there but Livia got up and whispered in his ear for a bit. He still looked a bit suspicious but sat down with Livia after a bit, opposite side of the table as me.
I'm paraphrasing here but the date was very awkward for me. Paul initially included me in the conversation but Livia started asking questions specifically to him, ignoring me and I guess he followed her lead.
Quickly felt like I literally wasn't there, they were just talking to each other and because they were close enough, they began whisper-talking, so I couldn't even catch what they were saying. I was embarrassed and didn't want to stare so just started using my phone to avoid eye contact, after a few failed attempts at starting a conversation with them.
You can probably see where this is going. Livia and Paul got increasingly flirty, her giggling more and more and him mostly just speaking into her ear and an arm around her back. After the meal, Livia got up and came over to me. Whispered if I could drop her to Paul's place instead of hers. My heart stopped, I just went "s-sure" and mumbled something I don't remember. She said they'd wait for me at my car and they just left me sitting there.
Then I realized they hadn't chipped in for the bill. It's strange but I think this was the first part that felt humiliating. I was embarrassed at being ignored during the date but not humiliated until I had to pick up the bill. I'm not sure why.
Maybe because as friends, I usually just went along with whatever Livia asked me. Like I said, she wasn't working, so driving her around and paying for her food was the norm when we went out. But adding another guy who she was apparently ready to fuck and having me pay for his food... that felt humiliating.
I had rubbery legs and wasn't really thinking clearly, paid the bill and went out to the car, where Livia and Paul were making out pretty intensely. I could see his back, he had her against the side of the car and her arms were locked around him.
I unlocked the car, they got in the backseat and continued making out without shutting the door. I felt a mix of humiliation and arousal to be getting the door for them.
I got in the driver's seat and asked for directions. They ignored me. Paul had his hand up Livia's shirt by this point and she was squirming and panting as he just kissed her all over her neck. I got hard looking at them. It was incredible! Like I said, I live in a very conservative city, so this was the first time in my life I'd seen people make out in front of me and my legs were shaking with how much more intense it all was compared to watching porn.
Paul stopped when he saw me looking, and they both straightened up. Livia looked flushed and was still breathing heavily. Paul gave me his address and I drove them there. They didn't make out on the way but kept whispering and pawing at each other.
When they got out, Livia told him to go on and she'd be with him in a minute. She turned to me and asked me if I could please wait for her and give her a ride home. I was really, really aroused (even though I didn't know I was a cuck back then) and would've agreed to anything she asked for then.
Livia followed Paul into his place and the door shut behind them. At this point, I was practically squirming around, desperate to jerk off but stayed in the car. I couldn't stop imagining the scene from the backseat, with panting and moaning and Paul all over her, face buried in her neck.
I eventually got myself under control but remained antsy. I hadn't thought at all how long Livia and Paul would be in there. Ended up waiting in the car with just my phone to keep me busy for nearly 3 hours before the door opened and Livia came out alone.
By this point it was getting dark, but I could still see she looked like a total mess when she got in the car: her hair was all over the place, makeup ruined, had lipstick smeared and honestly... I found her sexier than ever lol. She stunk too, first time I smelled sex on a person, for lack of a better description.
She put her arms around my neck and kissed me on the cheek. It was our first kiss. I turned to kiss her mouth but she gently put her hand over my lips, so I didn't push. She kissed me a few more times on the cheek, then put her hands on my face and gave me a deep kiss on the lips. I was a bit awkward, a bit too passive, so I'm glad she took control. Her lips tasted like sweat (or maybe it was cum? Can't totally recall).
After that she collapsed back in her seat and lazily reached a hand out over my crotch. Patted my hard-on and said "Looks like I'm not the only one having fun."
She then ordered me to drive her back home and I did. We didn't talk too much on the way there, she looked exhausted and even fell asleep for a bit. She kissed me again (this time a quick peck on the lips) when we reached her place and thanked me for the lovely night.
I was hard the whole time and it was only later that night, after jerking off that I realized how weird it was to be aroused at paying for the date and driving the girl I lusted for around after she fucked someone else.
After that, we became a lot closer and it became a pretty regular thing for me to drive her to her dates whenever she wanted. My phone is full of her texts, dating site pictures (she asks for my opinion), nude pics she send to her dates and more. Livia takes up most of the space on my phone too.
Here is what she looks like. And to this day, the smell of sex from that date with Paul is like a cuckold trigger for me.
Dan
