I was sitting down outside with my dog this past summer time seeing the evening sunshine after having a day that is certainly boring. I had this sudden urge to try something new. After surfing the web on recent dating websites I had visited for the past one week, which I put up a Craigslist posting seeking older women along with a merchant account on a cougar dating site. I then realized that I had racked up dozens upon lots of matches, whom most of them were “mature” women and it also gave me a better idea that I was likely to try and get wined and dined by sugar mummies without leaving a date too soon.
The chance of dating an online hot, mom-type figure may be the dream on most straight men growing up, but getting sugar mummy is one different thing. This is a full commitment to a different lifestyle and also a way of being treated. It was something I needed to try jus to know if the real thing lived up to the hype.
Rose was the first person to send me a text after setting my profile. She liked nothing but the forwardness I displayed in my bio and she also admired how I was hard-working at such a very young age. However, our online conversation quickly turned into more shallow words, such as how she wanted to kiss my sexy neck and how I also thought her butt was hot.
Since this was my first time dating women only slightly younger than my mom, I didn’t actually know what to expect and I got myself prepared to leave if shit got weird or uncomfortable which I expected to be the case. On the basis of the “horror” stories I’d heard from buddies that have gone on dates with people much older, occasionally things go awry when they discover the person is desperate to have a kind of kinky sex or treats the person like a fresh crop to be harvested.
When I arrived at the spot we both planned to meet, I was surprised to find Rose already sitting in an opposite direction to a subway station with her car keys on her left hand, patiently waiting for my arrival. She looked stunning, too. In a way, she reminded me a lot of my favorite movie actress whom I have always had a crush on. That alone got me motivated to flow along with her.
When she saw me striding over, she did not stand up. Instead, she made unbreakable eye contact with me like she did want to know my soul. Since I am also tough staring contest opponent, I kept my gaze locked as I stretch forth my hand and made the introductions.
“How are you?” I asked, to which she replied. “Great, great. Can we get going she asked? And I replied yes in a manner of approval. We left the north-end subway station around noon in her brand new Audi that smelled like fresh leather and expensive things. When I got in the car, she gave me a warm hug and greeted me with a big smile. She had a great laugh and also incredibly well-spoken. I was very comfortable, for the first time, it didn’t feel like I had to ease into the situation or fake little talk. She was quite fun to be with.
Rose was clearly into fashion. I am talking of layering and color coordination that even the most fashionistas can be pretentious and would lose their shit over It made me feel a form of underdressed, specifically because I became in my greaser regular getup. Either way, Rose didn’t seem to care as much as I did.
When texting each other beforehand, we had already planned to grab lunch and scope things out, to see if it was a perfect fit to go on further dates. I was pretty much happy with that idea, especially considering the fact that she probably had as many reservations on dating a strange young man as I did by dating a random older woman. We ended up choosing an Italian eatery in a trendy part of town. I truly looked forward to the prospect of being taken good care of by an older and more successful woman. It was actually a flip on the typical stereotypes of male and female interaction, and I love free food, so why don’t I give it a try?
After a few minutes of small talk, the ice melts quite easily. We ended up having a longtime dinner which cost $75, a bottle of wine for $30, and we both spent the rest of the evening walking together around the city slightly intoxicated. Throughout the whole night, my expenses were all covered. Rose was an accountant and she made it very clear that she wanted me to pay for absolutely nothing. I finally made the disagreement that I am getting worried about letting her pay for the whole dinner, so she agreed and let me buy us coffee when we stopped by a downtime diner which.
When it got to the time for us to part ways, she became very forward with me. She came closer to me very quickly, which I gave into with no protest. Obviously, for the first time in a long time, I really had to do virtually nothing on my end of the equation. We kissed for a bit on top of a park bench and parted ways. Before I left her, I told her that I’d be down to do that again.
It wouldn’t be until the final end of the summertime that we did actually meet up again for a coffee. When I ran into her this very time, the thing was a bit different. She seems to be a little less on edge but a slight more drained. Her energy was reduced, she was not smiling as much, and she appeared to be here out of a show of courtesy rather than to really have some fun. When we started talking and I asked her how things were, she told me that her step-mother passed away recently and things have been a bit rough.
We both spent the rest of the day talking and walking around the city. It was a bit gloomy that day because of the rainy weather and we ended up our conversation at a church. Rose told me that she would need some time to herself, so I gave her a warm hug and we parted ways. We never ended up meeting again, I tried texting her to check up on her and she said she is doing much better. She also told me that she really wants to quickly meet up soon to grab more Thai food. But I told her that I was totally down, even though that was a bit of a lie in order to finally stop her from feeling any worse than she currently was from her mom’s death.
If there is something I pulled out of the whole experience of being a male sugar baby, it’s that dating people way older than you are is a slight balance between challengingly exciting and might also be really uncomfortable.