[M]y [F]ormative years with a divorced MILF.

I received nice feedback in DMs on my first post — asking to share more. I’ve been thinking about my youth and how atypical my formative years were with regard to relationships and sex.

For most of my youth, my Mom taught dance at our home. I thought nothing of these women in our den dancing in front of wall mirrors. Yet, to say I never noticed would’ve been a lie. However, I never had any true interest. The biggest deterrent was death by both guilt and possible bodily harm from my Mom. Secondly, I had attractive girlfriends and female friends in and out of my house. It just was not really on my radar.

One Saturday, some of Mom’s students had stayed after class to hang and swim/tan. I worked late weekend nights as a DJ or roadie (story for another time). I got up late but I was asked to clean the pool as a couple of students were going to swim.

I’m out there finishing up. The ladies come out in their suits securing lounge chairs and laying out towels. They’re cackling and talking. I join in for a bit of banter, but I recognized this is a girl’s only party. One of my Mom’s students (Tamara 35/divorced) catches my eye in her two piece. She’s in fantastic shape. I’ve known her and her son for years. But this exact moment was very different. I caught a glance and a smile from her. My head started spinning as I walked into the kitchen to get a drink.

Now, I’m hanging out inside trying to check them out and figure out if I can get a chance to talk to Tam. Btw, I’m already thinking ahead of myself. See, her son (four years younger than me) has always looked up to me. He’s a good kid but kinda the little annoying puppy dog that follows you everywhere. It got worse by then at 14 y/o as he was having social issues as a Freshman. I finally ignore this red flag and make a move when she comes in to use the restroom. I make myself available in the kitchen and she sees me and joins for water.

We have small talk and I tell her how great she looks. She immediately blushes, but gives me a push in the chest – admonishing me as she’s known me too long. While laughing, she grabs my arm and is feeling my arm up. While we verbally joust, I catch her off guard and begin teasing her a little. I can’t remember exact dialogue, but I was/am pretty bold. My Dad taught me early on that ‘fortune favors the brave’. I wanted to taste her mouth right there but I let it go. She played the game well, but it was only flirting. I called it at that point and went about my day.

Days later, I’m thinking about Tam in her black bikini all lotioned up w/ beads of sweat — smelling of coconut, etc. Tam and her son lived a mile away from us. Her son used to bike over for help with various things from me or I was asked over to help move something. Anyhow, I take a chance the following weekend to visit. Her son’s home and I’m now stuck for a good hour.

I know I sound annoyed with him but he was alright in small doses. I do my best to be nice. It’s noticed and Tam and I eventually get a free moment. She asks why I’m there with a smirk. I tell her some stupid reason. She scoffs and I come clean that I couldn’t get her off my mind. It became real and she‘a momentarily deep in thought. I know she’s thinking about her friendship with my Mom as well as her son. I’m not oblivious to the risks here. However, I’m out of my depth as well. I’m not dealing with an 18-19yr old girl now. I decide to pull back and tell her I should be going.

For the next few days, I went from nervousness to resignation. I took a shot and missed. It happens. I figured I’d make myself scarce on Saturday until it blows over. Except, Tam asked my Mom if could come over to help with something. Nothing uncommon here and frankly, I didn’t think anything of it other than expecting awkwardness for the first 10 min.

Once I stepped foot in her house, I realized this was no ordinary visit. I learned her son was at his Dad’s this weekend. I’m usually cool under pressure but my stupid grin gave me away. She laughed, came forward, and took both my hands. I’m with a real woman now. My cockiness has slightly dissipated. She leads me to her bedroom and asks me to take a shower. I was dressed for manual outdoor labor. I was soon undressed for manual labor.

I’m lathering up when she joins me. I should describe Tam. She’s a gorgeous Korean woman who was in fabulous shape. Short with jet black hair past her shoulders. She had a cute trimmed bush. Her hips were broad and ass was full/tight. She had nice, perky breasts with light brown nipples which I got acquainted with immediately. Just a great hourglass figure and tight tummy.

We washed each other and she let me feel her out as much as I needed to. I still laugh at my reaction to her washing my ass with her sudsy hand. That was a first. We made out under the water as we rinsed off. Things started getting amped up now. We jumped out, toweled off and jumped into bed.

The shower helped calm me down and get my head into the game. I was determined to make her feel good. I was eager, but she had other plans. She wanted to take care of me. The first 15 minutes were filled with the occasional giggle along with “I can’t believe….(fill in the blank). Options incl: ‘you’re naked’; ‘in my bed’; ‘I’m holding your dick’, etc. It was good fun. Lots of laughter as we navigated this new chapter. Her tongue was amazing. She’s very oral. All over my neck…kissing my face, chest, balls and eventually teasing my cock. Her mouth was on me forever as it was a huge tease fest. I remember how amazing her ass felt in my hand. It was really the only part of her I could reach as she serviced me. Once I was ready, she wanted to fuck even if I wanted to return the favor. This was going down the way she envisioned so I finally gave in.

She mounted me slowly. She had this way of teasing her opening with my head. She did this for a while all the time. Eventually she’d sink down carefully as she was tight and I’m larger than she’s used to. I saw her hips move in a new and far more pleasurable way. Dance class had its advantages.

I’m seeing this woman I’ve known for years riding my cock. Riding me raw, no less. She’s repeating my name and is very pleased as she rode. My view was ridiculous but I had enough and flipped us both over. I fucked her hard and fast. Not my proudest moment with the jack rabbit fucking but I needed to cum. She loved the enthusiasm and kept urging me to cum in her. We were both in overdrive: panting and sweating. I remember how much she loved when I would unload in her. She’d squeal a little and coax every drop out of me.

We were spent but we laughed after the absurdity of it all. We laughed a lot actually. We talked a lot that day. She was very curious about me and women in particular. She’d ask my preferences in women, what I liked and disliked in bed, etc. I later realized she’d taken feedback and applied it.

We jumped in the shower again as I had a gig that night. Once finished and dried off, I had to have her again. She offered little resistance. I didn’t have much time, but I was determined to taste her. I took my time as I needed to leave with her wanting more. Giving oral is not a chore for me. I made her cum and she was wiped out (she had powerful orgasms). I was running out of time and completely blue-balled myself that night.

I was invited back on kid-free weekends off and on for about 18 mos (attended commuter Uni so close by). We had quickies as well as weekend long romps. This lasted until winter break of my sophomore year (she got into a relationship which she deserved…she was a catch). We had one last Sunday together which was a little emotional. It was a sad yet happy ending to our affair.

By that Summer, I was transferring to my preferred Uni. I learned a few things then. First, she talked after it ended. Girls night out inebriated story telling, apparently. Her loose lips got me a semi-regular hookup (another story altogether). Second, my Mom’s not an idiot. I was an adult and her friend needed someone trustworthy. Yet, she would not find the fling with her other married student funny at all. Tam’s wine night kicked off a conquest that I was utterly clueless about.

Source: reddit.com/r/gonewildstories/comments/klvskg/my_formative_years_with_a_divorced_milf