Gabrielle d'Estrees, 1594

Wednesday, October 13, 2010

Tales of Conditional Sex

Have you ever had to compromise or obey certain conditions to be in a relationship with someone?  Or even more brief – just to sleep with someone? I think we all have in one way or another. These are some conditional sex stories that I love and frequently share. 

I once took a wild trip to Miami with a group of about a hundered women.  Needless to say, there were dozens of scandalous memories from that trip, but this one is my favorite, hands down.  A Colorado woman in her late forties went out to a club one night and met a hot, 20 year old Latin boy.  They danced the night away and despite their age difference, had a hot sexual chemistry.  Her experience mixed with his good looks proved to be a great combination and a few hours later they were back at his place, having the kind of wild sex that can only be had in Miami. She woke up the next morning when her guy frantically jumped out of bed. There was a look of panic on his face. He was over an hour late for work. So he gave her his number and politely escorted her out the door.  A half hour later, she got a text. Turns out his tardiness was enough for him to loose his cashier job. Partially blaming herself, she felt for this young man. And being a successful entrepreneur, she began thinking of opportunities she could offer him.  An hour later, she called him back and made him the offer of a lifetime.  An offer any cougar loving man couldn’t refuse.  She invited him to stay at her Colorado mansion in the mountains. She promised to fully support him as long as he met three conditions:

1: He had to prepare a home cooked meal for her every night.           
2: He had to clean the house daily.
3: He had to pleasure her upon request.

Not a bad gig, eh?  Well the guy seemed to think so to because on the last day of the trip, he returned to Colorado with her to begin his new life as a man slave.  It certainly beats being a cashier.

Another friend came to visit me in college a few years back and I introduced her to a cute guy who lived upstairs from me.  Things went really well over the next few days and these two were almost inseparable.  On her last night, she snuck out of my dorm room and rushed upstairs.  He invited her into his room and they had an impromptu cuddle session. But when she started reaching down his pants, he stopped her.  He admitted that hadn’t been entirely honest and upfront with her. It turned out he had a girlfriend back at home.  She jumped out of his bed and was halfway out the door when he told her that he and his girlfriend had a special agreement while he was off at school: It wasn’t cheating if it was over the clothes.  This was enough to convince her to stay. So they got back in the bed and he started to feel her up… over the clothes, of course.  But every so often, she’d feel frisky and went to unzip his pants. And each time, he’d stop and yell “Over the clothes!” If this was a real condition, I have to give the guy credit for sticking to his guns. It takes a lot of self-control to stay on second base in college. But at the same time, a semi-open relationship is just ridiculous.

My last story is short and sweet.  One girl was stuck in a nearby city and needed a ride home after last call.  No one was answering their phones so she had to resort to calling an old flame.  This guy knew he was in control when she begged him to come and get her.  So he told her he would only pick her up if she would come spend the night with him.  Knowing that she had no other options, she regretfully agreed.  But that wasn’t the only condition. He had also been craving a roast beef sandwich (not an innuendo) from one specific sandwich shop and was short on cash.  So when he drove up, she gave him last four bucks in her purse.  They got the sandwich to-go, went back to his place, got it on and then she watched as he enjoyed his roast beef sandwich after the sex. Talk about adding insult to injury. She should have resorted to walking because that cab ride cost her a roast beef sandwich and her dignity.   

So that wraps up this week’s hump day. And what’s the lesson this week? Hmmm… I’d say we should all seriously consider the conditions of our relationships and hookups before jumping into bed with someone. Sometimes it’s the cost of a roast beef sandwich and sometimes it’s a lifetime of sex slavery. In any case, don’t ever be afraid to ask yourself “is this really worth it?” I asked a bunch of my guy friends that same question when telling them about the Colorado cougar. Each of them had the same response. “Absolutely.”

And for last week’s hump day stories, click HERE.


  1. It's interesting to think about how people would react if the tables were turned and it was a young girl living with a rich older man in exchange for sex. I'm guessing that it wouldn't be too positive.