An older woman kinda ruined me.
I was 16 at the time and it was my first time having sex, I admit. However, this older lady that took an interest in me gave me her phone number. I had no car, I had no money, and I just went to school and came home. She offered to take me to school instead of the bus on mondays and tuesdays and I said that would be great. She wasn't someone I knew directly but her top friends were the mom's of my classmates, but I wasn't that social to begin with to really know the moms of my classmates or the classmates themselves too well. I only sat well with everyone, I realize now, because I played football. We texted pretty much all the time for a week before she even offered to take me to school. It felt like genuine kindness at the time. She drove me to school for those first two days. Roughly 10 minutes of a drive. I didn't tell my mom because I don't really see her much as she worked two jobs that ate up all of her day basically everyday and I figured I'd tell her later. I didn't like taking the bus, mostly because of the 5 minute walk to get there and the two really harsh bus drivers.
Anyways, the first monday and tuesday went on fine. The second Monday is when she drove me elsewhere that wasn't school. She took me to a breakfast place and said I can skip school for a day and have breakfast with her instead. That was fine for me as I skipped classes here and there, almost twice a month, mostly to play video games. My mom wouldn't get mad really, because my grades were pretty good and I always did the extra work from the missed days anyways.
So we had breakfast at this small restaurant that opened super early to serve coffee and donuts and was next to small outlet stores. We sat and ate for maybe a couple hours and talked about our day to day. She was actually really nice to talk to. She had kids older than me and they used to go to my school, now graduated and in college but they still lived with her. She had a husband that she didn't really talk about much, that should have been my first clue on her intentions during prior texts, but I was not the cleverest guy at that time. After the breakfast that she paid for, I thought we were going back to my house, which would have been fine. Instead she drove me to a hotel and said she has it booked for a couple days and they even have a pool and so on and so forth. It was a holiday inn. Probably a pretty normal holiday inn. I honestly didn't know what I was doing and kind just went with it and became somewhat quiet. We got to her rented room and she said she was gonna take a quick shower. Me being kinda overwhelmed because honestly she is somewhat attractive, actually nice, and smells really good I kinda just listened to whatever she said. I liked her and did have some interest in her but I never really flirted. So obviously it was pretty exciting to know this woman was taking her clothes off and taking a shower in the hotel room I was in. She didn't strip down in front of me and I just lounged around and turned the TV on after looking out the window. I didn't find anything to watch and settled on a FX movie showing of Xmen with wolverine in it. No longer than 10 minutes she came out with just a towel and she asked if this is okay with me. I said yes, completely in denial of what is happening. It was very awkward to me and in hindsight she was very comforting during my first time. She was on top. I don't think I would have had the confidence to be on top at the time. To my credit, I lasted enough to at least have her cum first. I knew because she told me and was very vocal about her pleasure.
The next time we came together was at her place on a Sunday and basically every other day or more we would find time to meet at the hotel or her house when her kids and husband weren't home. We had planned out the nit being late too much for my first class. I was in heaven. I did tell her I felt this was all wrong and I was scared we were gonna get caught, but she had us promise to keep it between us. I won't mention her name or her features. I will say, at the time she was 38 years old. Over the next two months it would keep going and somewhat intensified as she brought one of her friends, someone I didn't know at all into our affair. It took a while for me to be okay with it, but being sexually intimate with people is a powerful ice breaker. This too continued for a while and then all of a sudden I was just left in the cold.
It broke me inside and I felt lost and probably depressed though I never want to admit that. I was ghosted even by the second woman.
During college I became somewhat of an addict and really went after older women, but no one ever felt right. I was chasing that high and I loved getting it with older women. I have had many partners by this time and even had several girlfriends my age, but there is always this hollow section in my chest that doesn't allow me to enjoy the sex or the dates than the times I have had with that first older woman in my life. I didn't have it in me to break the promise I made and I also don't want to condemn her by ever mentioning this to anyone. I'm 33 now and I have a loving partner of my age that I do love, but it eats at me when I remember the times with that older woman and I find myself lusting after many older women I come across. I hope she's doing well, but I feel I have been altered in a manner I shouldn't have been.