Anonymous Confession #338: “My 1st Sugar Baby Sex Date”

[CW: sex work, some explicit discussion of sex]

Published from an interview with Stephanie Pakrul, November 2018.

Stephanie: Thank you for talking to me today! You once told me about your first sex date as a “Sugar Baby” and I’ve asked if you would share your story here. What was your motivation for agreeing to do this? #338: I believe that living without self-deception is the essence of bravery. I may not be brave enough to share this with people in my everyday life, but I’d like the world to know more about the raw, honest truth behind this kind of sex work that goes on everywhere.

Stephanie: So tell me how this “first date” came to be? #338: It was 2013 and I was broke thanks to a major breakup and medical bills. I loved sex and knew I could be charming to men, so this was like a “why not?” kind of thing. A few days before, I had created a profile on the most popular Sugar Daddy/Sugar Baby dating site and spent most of that week studying what to expect and fielding messages and coffee meetings with POTs (POTential SDs). Tom [not his real name] and I went out for drinks and dinner, which turned into negotiations by the end. I felt lucky that he was experienced at this because I was pretty nervous. He had a business trip soon (they always do! haha) so we agreed to meet the next day at his place, for sex.

Stephanie: You had agreed on money at this point? #338: Yeah. Based on my research, I wanted to have a set monthly allowance arrangement, but I was his third SB and he didn’t like the “restrictive” approach, so we agreed on $500 per meeting. This was less than I wanted, but I felt okay with starting there. We sometimes call these Splenda Daddies.

Stephanie: Did you have concerns about safety? #338: Oh definitely. I had a basic plan in mind to always have a safety buddy who I would tell the name and phone number of the person and address of where I was going, and any other details I had before any date. They would be on alert until I sent them a message to check in after the date, and the person I was on the date with knew this. A friend had helped me get into a private forum for sex workers, so I picked up a lot of knowledge about stuff like this from there.

Stephanie: So, it’s first paid sex date day! How do you prepare? #338: This is the funny part of the story. First of all, I had to buy condoms, and this was something I think I had literally never done and was feeling stupidly embarrassed about that. They were always either from free clinics or something my partner had, if we even used them at all. But obviously this was not a case where I was going to rely on the common sense of a horny dude!

And then at Walgreens, I realized I had trimmed my pubes, shaved my bikini line, done makeup, dressed nice… but literally forgot to shave my legs. Rookie mistake, right? So next thing you know, I’m sitting on the toilet in the handicap stall at the Oakland Museum, five minutes before closing, dry shaving my legs. I even went BACK to Walgreens after to get some lotion.

Stephanie: Oh my, I can picture it! Poor legs. So you show up at his place. How would you describe it? #338: Meh your usual nicer Bay Area apartment. Cool but way too much generic IKEA for someone who is a VP of Engineering at a startup I’d actually heard of. I ask about the ethnic cookbooks and he starts talking about his marriage difficulties, and actually he kinda blows my mind by saying that while he wants a real open relationship with her, they’re in therapy and she’s okay with him having sex with other women, but only if he pays for it.

Stephanie: That’s an interesting boundary. How did that work out? #338: The idea was to keep out emotional involvement, but not that we really have much control there. I ended up seeing him for a while and as far as I know they’re divorced now and he’s much happier. Of course being a SB is usually even more about being a therapist than having sex, so you get to hear a lot of interesting relationship details.

Stephanie: How are you feeling once things start getting intimate at his place? #338: He’s actually pretty young and attractive and kisses well, so that helps. Also, sexy accent. I’m anxious because it’s all so new and I’m fresh out of a long term relationship, but feel like I know what I’m doing and have practiced my boundaries. Clothes come off and the sex is pretty enjoyable! He’s pleasantly well-endowed and we have a good connection in bed. I remember that he complimented me about the way I moved on top and that got me excited.

Stephanie: You mentioned boundaries. Was there anything that felt like it pushed a boundary of yours? #338: He wanted to have anal sex. This was a big thing for him going forward that I was cool with, but was not first date material.

I know he was disappointed, but in my mind, being a sugar baby is somewhere between a girlfriend and an escort. Yes, as the wealthy guy in the equation, you get a lot of control and ability to smoothly skip ahead in terms of an intimate physical relationship. But I’m not an escort with a menu of services (not that there’s anything wrong with that, just not for me!) so I have always tried to make sure these relationships were as mutually genuine as possible, like with dinner dates out in the real world and stuff too. So a big part of that is reminding them you’re a real person with real feelings and there’s gotta be a natural progression of things.

Vladislav Reshetnyak

Stephanie: What happens post-coitus? #338: We each showered, I reassembled my hair and makeup, and we enjoyed a luxurious tasting menu dinner at a nearby restaurant. I wasn’t exactly sure how the money exchange part would work, but he handed me $500 in twenties on the way, so that was easy. We parted after dinner on a nice kiss and actually ended up seeing each other like this for a couple of years.

Stephanie: How did you feel after the date? #338: I couldn’t stop grinning the whole way home. It was empowering! The power of pussy! I had a potential way out of the financial bind I was in that I actually didn’t hate. I definitely needed to do some self-care, as I have tried to do before and after every working date since, but it was a really positive feeling, like I was good at my job.

Stephanie: Thank you so much for sharing! What would you like readers to know about you, the person, and not just the sex worker? #338: Even though I’m not doing sex work these days, I’m proud of what I gained (and gave back) during this part of my life and it made me a better person all around. My compassion and understanding of relationships grew massively. I see the slogan “sex work is work” and this seems like an important message. What are athletes and farm workers and surgeons if not also just people who get paid for the skills and labors of their body?

I know we are focused on the message of women right now with #metoo and that is very important for rebalancing things. But there is so much pain trapped in men too, and in my experience they don’t have nearly as much support for handling it in healthy ways, and that sometimes scares me. So, treat your sex workers well and remember they are people too, with complex, beautiful lives, providing a skill to be valued in society!

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Stephanie Pakrul 🌈🖤🦢

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Talk to me about mental health, nerdy things, entrepreneurship, sex work, polyamory, web dev, & life in a hippie hacker dorm in San Francisco.

Not A Victim

Confessions of love, fear & shame, in your own words