While in my junior year of college, I ran into some financial problems and resorted in trying to find a sugar daddy to help me through the rough patch. It wasn't my best idea or something I was interested in doing for the long-term, but at the time after hearing a few success stories, I thought if I somehow got lucky and met the right person, it would magically solve all my money problems.
Not long after I made a profile on a sugar daddy dating site, a woman messaged me and said she would be interested in helping me. Her message stood out from all the other messages I received because she was a former professional WNBA player. Other than that, she didn't give me too much info about who she was but said her name was Darcy.
This really struck my interest because I was big into fitness and sports, and was a rising college track athlete. The world of professional sports and athletes was always something I was fascinated with and inspired by. I also considered myself to be bisexual, open minded, and was really drawn to the idea of trying out a sugar relationship with a woman first. This way, I thought it would be a lot safer compared to meeting a man.
After the initial back and forth messaging, it was hard to get in touch with Darcy to meet in person and at one point I thought she had forgot about me to pursue someone else. Eventually, we met at a bar near my campus. Darcy was 6'2", very built and fit, and probably in her late 40s. She was black and talked a lot about being a black female athlete throughout her professional career in the WNBA, the challenges she faced growing up. She told me she was a lesbian, looking for companionship with a younger woman. She told me I checked all her boxes: "attractive, white, blonde, fit, athletic college girl" - the type of person she always bonded with well during her college years.
I was very honest with Darcy and told her it was my first time looking for such a relationship and told her about my financial situation. Darcy responded by telling me she was willing to help, she was very experienced, she had more than enough money to splurge, and she was more so looking for a "hangout partner" to do stuff like hiking, restaurants, working out, tennis, shopping and whatever came to mind. She promised to give me money each time we met.
Most importantly to me, Darcy promised to help me get publicity, introduce me to "powerful people" (as she put it) in the sports industry. After hearing this, I was beyond excited to find an arrangement where I thought I would be getting paid to basically just hangout and talk with someone famous and influential.
There was a period of no contact until about a week later, when Darcy texted me to go hiking. It was an afternoon day hike at a local trail outside of the city and not super eventful. I recall we just had casual conversations throughout the hike, followed by some food. During the hike, Darcy asked if we could hold hands at times, and I agreed. There wasn't any physical contact beyond that. We finished the day by going out for dinner and cocktails. Darcy gave me $200 in bills at the end of the night.
A few days later we went to watch a movie before having dinner, again Darcy gave me some money before we parted.
Darcy was very private about her personal life and I really didn't know anything about her even though we talked for hours at that point. She said she never "came out" so her friends and family don't know she is a lesbian. She also told me many times to keep our arrangement discrete and act as if we are just friends if we ever ran into someone she knew in public (we never did). OTOH I was naΓ―vely open and told Darcy a lot of personal info about myself when asked, like where I grew up, which college I was attending, the place I was working part time, what my daily schedules looked like. Our conversations solely revolved around Darcy's professional basketball career, fitness and sports, or about me.
Our third get-together was a massage and sauna appointment at a high-end spa. It was at a place I always wanted to try but was too expensive for me, so Darcy paid for us. We did some workouts before the massage, some swimming, tea, and then the sauna.
This was also the first time I noticed Darcy taking a sexual interest in me. In the locker room, I caught Darcy staring at me while I was changing to my swimsuit. Afterwards in the spa area, Darcy took a few pictures of me in my swimsuit with her phone and made some compliments about my body. I was flattered and didn't think too much of it. In the jacuzzi, Darcy sat very close to me, with our legs touching. I was worried Darcy was going to take it further but some other people joined us in the jacuzzi right after and Darcy stopped her advances.
One Friday night, Darcy called to invite me to work out with her the next Saturday morning. She lived alone in a big apartment with a home gym. It was my first time seeing her place. Even though the apartment was really big with many rooms, there was not much in it and had very minimal furniture, kind of like it was a temporary place or she just moved in. During the morning workout, she showed me the routines WNBA and professional athletes did before a game, something I was really into.
After our workout, I was showering in the bathroom and I didn't notice Darcy walk in until she opened the shower stall door, stepping in. I was shocked at the time as Darcy stood behind me and began to caress me. It was like a big hug and I could feel her kissing my neck. I remember I could smell a sweaty odor from her. She was huge, lean, and strong, and she towered over me when she ran her hands throughout my body. Darcy probably noticed my nervousness because I was so tense and kept telling me to relax. I really didn't know what to do at the time, I remember kind of trying to laugh it off and play along as Darcy was kissing my neck and back. It was my first time being touched by another woman like that and I was not ready.
Eventually Darcy dragged me to the floor of the stall and had her hand between my legs, massaging me and trying to give me pleasure, telling me to orgasm for her. I was freaking out at this point. Darcy was also kissing me on the mouth, with her tongue licking my lips. Darcy at one point was holding me really tight with her long arm wrapped around me as I sat between her legs, where I had trouble breathing. I couldn't see but could tell Darcy was pleasuring herself at the same time. It only ended after Darcy had an orgasm (I did not).
I tried to be cooperative and wanted to go home after we finished showering but we weren't done. Darcy had us do stretches nude in the vast and empty living room where there was a lot of sunlight. She was said it was a good way to spent time as our hair dried.
Darcy clearly had the intention of trying to make me expose myself in the crudest way possible, for example instructing me to spread my legs apart and bend backwards, upside down bicycle exercises, doing splits, all while positioning herself behind me to watch. I can't recall my exact feelings at the time, but I was scared even though Darcy was never forceful or demanding in anyway.
As I was finally leaving, Darcy had me hug and embrace her at the door, which was uncomfortable and felt like it lasted forever. This time, Darcy only gave me a few bills totaling maybe $40 and said she didn't have enough cash but will make up for it next time, promising me a few hundred at least.
The sudden turn to intimacy really caught me off guard and made me feel uncomfortable for a period of time. Darcy also texted me after saying she hoped I enjoyed the "girl-on-girl fun" and thanked me for being "open minded about it" as she put it. Darcy invited me for lunch the next weekend and we didn't talk about what happened the previous Saturday.
I think Darcy picked up on the change in my demeanor and tried to make it up to me by inviting me to an advertising shoot for this beer brand I never heard of. It was basically me holding a can of the drink and running on the beach in a bikini. The clip would be included in the rest of the ad.