Cougar Date Story #3: A Double-Date Gone Horribly Wrong

One of my first encounters with a Cougar came a few years back. I’m not really sure what I was thinking, but I agreed to go on a double-date with the woman I met on PassionSearch.com, my buddy Samir (he’s a goofy Albanian dude), and her friend (also a Cougar). When my lady mentioned she had a friend that wanted to double-date with us, I thought this was the perfect opportunity to invite Samir along. I knew he had a thing for Cougars. As it turned out, this was the dumbest decision of my life. And that says a lot!


The 4 of us met up at an Over-30 Club. Basically, this is a place where mostly older men and women go to dance, drink, and hookup. It’s probably the easiest place to get laid. Unfortunately, the majority of the women under 250 pounds have fucked up teeth because they’ve done so much Meth. Occasionally, an in-shape woman that wasn’t smacked hard in the face with the ugly stick goes in there. But chances are she’s younger and not looking to hookup. It’s still a fun place to go. The music is pretty good, beer is cheap, and looking at the other patrons in the bar helps boost my self-esteem.

We arrived at the club at about 10:00. My date looked good and my friends’ date wasn’t too bad on the eyes either. So we were both happy. We gave each other the thumbs-up to show our approval for each other’s dates. After meeting, we grabbed a drink and then headed to the dance floor. I wanted to get my date in the mood. A couple of drinks and sum bumpin’ and grindin’ will do that. Things started off well. She was definitely into me and her friend was definitely into my buddy. We knew early on we were going to get laid.

Normally, if I’m on a date, I try to move the party to my bedroom as quickly as possible. I don’t want a woman to lose interest before I hit it. That didn’t work out so well on this night because it wasn’t just me and my date. I had problems getting her full attention. Since we were in a group, thdies e 2 lawere interested in chatting with both of us and each other. So this prolonged the inevitable (me getting laid). Don’t get me wrong, I was never worried about getting laid. This chick was easy and I could tell that from the beginning. But I don’t like to wait to get laid. What was I supposed to do? Go beat it in the bathroom to tie me over?

My date looked good

My date looked good

The longer you stay in a bar, the more alcohol you – and those with you – will consume. By 1:00 in the morning, we were still at the bar. But now we were all rather intoxicated. I was the most sober of the group and my buddy was in decent shape. Finally, we left the bar. There was a convenient store next door that we stopped at. I grabbed a box of condoms and some gum. The ladies went to pee (together, of course). After I paid for my goodies, I went back to the condom aisle to check on my buddy. I wanted to get going because I was ridiculously horny. So horny that I would have shot a load if anything made contact with my dick. The holdup was my friend didn’t know what condom to buy. I didn’t know if he was a virgin. Never had that conversation with him. But he asked me to help him make a purchase. To which I responded, “hell no, man, you’re on your own!”

I’m not about to help another dude buy condoms. What was I supposed to do? Ask him to whip out his cock right there in the store? So I walked away and headed for the car. Everyone followed shortly after. My date hopped into my car, his date hopped into my friends car. Since we were quite far from either of our houses, we decided we would just find a secluded area and fuck our ladies. There was a gravel road nearby that we found. He pulled his car about 200 feet away from mine. I was too tired for sex, but I was still horny. So all I wanted was a good blowjob. I ended up getting perhaps the best head I’ve ever received. Who says drunk chicks can’t suck a mean dick?

I’m not about to help another dude buy condoms

I’m not about to help another dude buy condoms

Both women live together. So we left my car at the gravel road and got back in his car to take them home together. After dropping them off, Samir and I shared with each other what we did in the car. I told him all I got was a BJ because that’s all I wanted. He said that he fucked his woman. I high-fived him like any proud friend would do. But then he said something that was a bit disturbing…

“I didn’t use a condom”. Say what? He didn’t wrap up with a woman he had just met. For all he knows she could have STD’s or not even taking any birth control. He was 26 years old at the time. How can he be so stupid? And it’s not like he didn’t have the opportunity to purchase a condom. After all, we did stop at a convenient store for the sole purpose of getting rubbers. “I didn’t know what to buy. You wouldn’t help me”. Why a 26 year old male doesn’t know how to select a condom is beyond me. The next day was quite entertaining. He was freaking out that he contracted an STD or knocked her up. So he called her constantly to make sure she’s clean. She wouldn’t answer. She never spoke to him again.

Sexual experience

Sexual experience

My woman told me her friend spent most of that day making fun of my buddy for his lack of sexual experience. I wanted to get together with my date again. But because my friend was such a goofball, neither of them wanted to speak to either of us anymore. I remember the text I received – “sorry dude you should have picked a better date for my friend. Bye”. Lesson learned.