My Darkest Secret: The time I [F] Accepted $500 cash to have a hot foursome [Group]

Warning that this is a super long post – this is something I have never told a soul, so I thought it warranted a little backstory. Scroll to **~~Action starts here~~** if you want to skip ahead.

So far on Reddit, I’ve written about my sexual adventures and misadventures fucking my coworker, cheating, and masturbating at work. But there’s something I’ve never told anyone before; offline or online. When I was 21 (I’m 25 now), I went through a phase for about a year where I was meeting up and hooking up with older men from the website SeekingArrangement. For those of you that don’t know, SeekingArrangement is a sugar daddy website where younger girls can find an older man who will agree to support them financially either through an allowance or through one-off payments. After I graduated from college, I was working a really low paying job at a non-profit, and I live in a pretty big city where the cost of living is high. I had just broken up with my boyfriend of 3 years and I was exploring my sexuality. I felt the desire to explore my submissive side more, and I thought, why not make a buck while doing it?

I have always looked quite young and innocent for my age, and always received a lot of attention from much older men. I am 5 foot 4, and about 115 pounds with perky C-cup tits. I have a really exotic look to me, due to my mixed ethnic background. I probably slept with about 10 men from this site, and made a few thousand dollars total. Looking back, I don’t really know what drove me to create a profile on the site. I have always been a straight-A student, went to an elite university, and had a steady boyfriend for most of my time as a student. I think that after I graduated I wanted to let my naughty side loose. What thrilled me the most was that my family and friends would never guess in a million years what I was up to. When I would meet up with friends and they asked me what I did the previous night I got turned on as I gave them some vague excuse, knowing that they’d never guess the truth. When I think back to this time, I do feel a little bit ashamed at how extreme it was (and even a bit dangerous): showing up at hotel rooms to meet complete strangers, fucking them, and leaving with a wad of cash in my purse.

I read an article online about how some girls were paying their way through college through finding sugar daddies on the site, and I got a little wet just reading the article. I rushed to make a profile the next day. It’s not that I badly needed the money, *per se*, but knowing that a man was paying me to pleasure him turned me on immensely. I knew that I wouldn’t be able to say no to anything they wanted from me and that I would be under their control completely. As soon as I made a profile, my inbox was flooded with men ready to offer an “allowance” in exchange for a fuck almost immediately. I was off to the races…. and totally out of my comfort zone.

While there are plenty of stories I could share, I wanted to share the time that was the most extreme, and arguably the sexiest. I started to chat back and forth with a somewhat attractive doctor, who we’ll call Tim. Tim was about 45. Tim said that he was coming to visit my city and that he’d love to have some fun. His message stuck out because he was just visiting which was perfect for me – I love the thrill of a one-off encounter. As we started to message and exchange pics, he sprung on me that he’d be bringing his ongoing sugar-baby girlfriend with him. He texted me a few pictures of her, and she was about my age and very cute. I am bisexual so this started to sound like even more fun for me. Then he sprang something else on me, his sugar baby really wanted to invite another guy along. He asked if that was okay with me. I said, as long as we are all practicing safe sex, I am down for anything. In the days leading up to this, I got pretty nervous and considered backing out. Sex with 3 complete strangers at once? I had literally never done anything like it. But when the time came I put on a sexy dress and called an uber to their 5-star downtown hotel.

I head up to the floor he told me they were in. It turns out to be a big penthouse room with a great view. When I get there it’s only Tim, his sugarbaby, Anna, and me. Tim was a very average looking guy in his mid-40s, with a total dad-bod. Anna had a really sweet girl-next-door type of face, and was about my height and also slim. I sit down and we make small talk. Honestly, I was feeling kind of awkward. Thank god they had some bottles of liquor. I start throwing back a gin and tonic, wondering when this other guy is going to show up. Over text, Tim had been really dominant and very sexually forward. In-person, he was slightly more reserved and Anna was more of the talker. About 10 minutes in, there’s a knock on the door. Another young fairly attractive guy with dark hair shows up, he might be in his late 20s? I’ll call him Andy. Andy sits down and has a drink and the conversation starts to flow a little easier. Anna asks us a little bit about the craziest things we’ve ever done sexually and we all start to share. Turns out no one had ever had a foursome before, which put me a bit at ease.

**~~Action starts here~~**

As the conversation started to get a little hot and heavy, Tim suggested we move from the living area to the hotel’s bedroom, where there was a massive bed. We head over and Anna and I are the first to start making out, while Tim and Andy watch. Tim comes over, behind me, and starts to feel both me and Anna up while we’re making out. He starts to take off my shirt from behind. Suddenly all awkwardness is gone and I’m starting to get wet. I love the feeling of making out with Anna’s very soft lips, putting on a show for two needy men. After Tim took off my shirt, I temporarily break the kiss to turn around and look around. Both Tim and Andy are starting to stroke themselves above their pants. I break the makeout and I crawl over to Andy and take his dick out. It’s nicely sized and clean. I start to give Andy head. I glance over, and Anna is doing the same for Tim. After about five minutes, we switch and I start sucking Tim’s cock, which is a little larger. I start getting really enthusiastic and sloppy with it. I loved being a little preformative knowing that Anna and Andy could watch. I also knew that Tim was the one paying me for this, and I wanted to show him my slutty appreciation. He starts getting close to cumming, so he stops me.

I took this chance to crawl back over to Anna. Andy is standing up near the edge of the bed and Anna is sucking his cock. So I get behind her and start eating her pussy. This is only my second time eating pussy and I love it. I work my way from her clit upwards, every once in awhile wiggling my tongue inside of her. It was around this time that I started realizing I was bisexual, so I was truly enjoying the experience, and I could tell she was too as I heard her moaning into Andy’s cock. While I was eating her out, Tim had put a condom on and entered me from behind. He started fucking me hard. My mind was spinning as I realized I was being fucked by a man twice my age, eating his girlfriend out, while she gave another gave head. Honestly, I still wasn’t sure at this point who exactly Andy was or how he was connected. We were literally all in a chain pleasuring each other about half an hour after we met for the first time. Tim kept fucking me and I felt myself reaching the edge. He wasn’t the most attractive man in the world and his dick was quite average, but he could really fuck with some force. Every once in a while he gave me a hard spank. I was loving it. I had to take a break from eating Anna out, and I started to cum hard.

After I came, we decided to switch it up. I had mentioned earlier my interest in sucking dick while getting fucked at the same time. Andy put on a condom and came behind me. Tim laid on the bed and I started sucking his cock again. Anna was sitting next to Tim and making out with him. The whole thing was very erotic and very natural. We did this for a while until Tim was about to cum so he stopped me again. By this point, I had cum again, even though Andy was a little bit less enthusiastic and less forceful. After this Andy laid back down on the bed and told me he wanted me to give him head. I started working on his cock and he started getting really forceful and specific with his instructions. He instructed me to play with his balls, and kept ordering me to go deeper. It was kind of clear that Andy was much more attracted to me than Anna, and maybe not as enthusiastic about the foursome. He was getting entirely wrapped up in me giving him head, and I was really enjoying being told what to do, and obediently obliging. As I worked on him, I felt his body start to tense, and his cock started to quiver. A moment later he was filling my mouth with his warm cum, and telling me to swallow. I obediently swallowed every drop of this stranger’s cum. I had had one night stands before with someone I met at a bar or party, but I had never swallowed a complete stranger’s cum like I was just then. After Andy came he really lost interest in what else was happening and kind of went to the other side of the bed to watch.

Tim had been fucking Anna and seemed ready to cum as well. I crawled over to their side of the bed, and he pulled out of Anna and ripped his condom off. Anna spun around and we both laid next to each other under his hard cock. He started stroking his cock, and we opened our mouths. A second later he was cumming over both of eager faces. This might be one of the hottest moments of my life. After he came, Anna and I started making out with cum all over our faces and putting on a little bit of a show. I love being a little exhibitionistic with another woman while men watch.

After we were done, Anna and Tim went to shower off. I cleaned up a little in the bathroom and sat on the bed with Andy. It turned out that Tim had met him on SeekingArrangement as well, and was paying him to be there too. He got my number and told me he wanted to take me out and fuck me again. Anna came back out of the bathroom and told me and Andy to go in; I wasn’t sure why. When we went in, Tim was in there in a bathrobe and handed Andy and I each a wad of cash… $500 each. I found all my clothes, got dressed, and left alone after that. This was a Friday evening and we were done by about 10pm. After that, I went out to a bar to meet some of my friends who were having drinks. I told them I had just finished babysitting – which was my other side gig at the time. I felt super dirty knowing that my friends had no idea what I had actually just been doing and that I had not even showered off, before coming to meet up with them. When I got home later that night, very tipsy, I immediately grabbed my vibrator and re-lived the whole experience again. I have other stories I could share, but I’ve never done anything *quite* like this again.

I am happy to answer questions if I left anything out or if you have questions about my time meeting up with strangers for money. Thanks for reading :)

Source: reddit.com/r/gonewildstories/comments/gbif9y/my_darkest_secret_the_time_i_f_accepted_500_cash