Tammy and the Blindfold [MF]

Before it became unusable, OKCupid was an amazing way to meet women. No fees, no message limits, it was perfect. One night while I was recovering from surgery I connected with Tammy. I was 38 at the time, she was 49, 5-4, petite, red hair, and green eyes. We got to talking and I found that she was divorced about 10 years, and lived alone about 45 min away from me. The fact that I was married didn’t slow her down, and found that despite her very reserved and somewhat innocent appearance, she was quite adventurous.

In the course of talking, I mentioned to her that one of my favorite fantasies was to meet a woman for the first time with her waiting in bed for me blindfolded. Shockingly, she thought that would be fun, and suggested that maybe we give it a try once I was fully recovered, to which I immediately agreed.

2 very long months later, I was all healed and ready to go. We planned for a weeknight after work, so I left the office, grabbed some dinner and showed up at her place around 7. I parked the car and texted her that I was there, and her response was limited to, “Apt 34, door is unlocked”.

Robin and the Bet [MF]

I first connected with Robin on the same dating app a few weeks after the last time I met up with Melissa. Robin was 48, two kids, divorced and had her own home about halfway to my job at the time. The first time we met was at a bar in the middle of a snowstorm. We had both gotten out early because it had already snowed about 10″ and wasn’t going to stop anytime soon. Since I wasn’t expected home for a few hours later, I suggested that we grab a drink.

We met a the bar, conversation was OK, but I didn’t think it was going anywhere. After an hour or so, we decided it best to each get headed home due to the snow. Our cars were the only ones in the lot, and parked right next to each other. I walked with her right to her drivers door to say goodnight, and there was an extremely awkward pause, like she wasn’t quite ready to leave, so I went in for a kiss. To my surprise, she kissed me back. We spent the next few minutes standing there kissing, until the cold got to us and we parted ways for the night.

My Night with Melissa [MF]

This is the story of the first time I strayed from my wife, and first time sharing this story with anyone. Assuming it is well received, there will be more to come….I met Melissa on a dating site, I was 35, and she was a year older than me, 5-6, blonde and very sexy. We texted back and forth for close to a month until one day I mentioned to her that I had to travel to Providence overnight for a work meeting. We both lived in the Hartford area, so she suggested that I pick her up on the way, and keep me company in the hotel. I was very nervous, but against my better judgement I agreed.

A week later I pulled up to her house, sent a text that I was there, and she replied that she would be ready in 5 min. 10 Min later she walks out the door looking absolutely stunning. Low cut blouse, tight jeans that made her ass look amazing, and 3″ snakeskin heels. I helped her with her bag, we got in the car and were on the way.