Weekend Fun

Where are you from?

The Chicago(land) area.

Or he is passed out upstairs, drunk from the party you threw and we're fucking in the basement.

Offering massages has gotten me laid many times on the road. It is an innocent offer to open up a door to go somewhere private and touch someone.

Dating and open

I've been fucking/dating this divorced friend for some time and we have started referring to each other as the girlfriend/boyfriend. We still know it is not exclusive and she has really enjoyed time with me because of my open-mind when it comes to sexuality and her wanting to explore it for herself. She has gotten more dick since her divorce than before. I've helped her meet other guys and encouraged her to do so. I rubbed off on her with my vice for married women and she has gotten off by finding and fucking married men. We have played with some of her female friends and there is an understanding that I fuck them on the side if I want.

She joined me with some single women, but it wasn't until recently that a few married women I've been fucking have felt comfortable joining us. Typically they just want discretion and limiting who know they cheat in whatever circle. The hottest was fucking my friend's wife, who hit it off with her. I didn't blow my friend's wife's cover. She actually brought up sexual topics with my g/f and after my g/f confided in her about some sexual exploring, she picked up on how my friend's wife and I don't always get along in social settings (most people think we dislike each other), but she seemed interested in her. She put two and two together and asked her. I guess my friend's wife was stunned and her lack of answering was all the answer my g/f needed. Since then, we've found three times to get my friend's wife to get away from the fam, meet at my g/f's place and fuck.

I also fucked her with my neighbor, who was super interested in my g/f. The neighbor kept asking about her and when we admitted to a deeper level of dating, she insisted on meeting her. It's been a great adventure so far.

One night stand

I’m in Boston this week, for work, and last night I met a flight attendant at my hotel bar.  Her crew retired for the evening and she was looking for company.  She is married and in her late 20s.  The flirting was forward from both parties, with a lot of “if I wasn’t married” and “if you weren’t married” lines.  Those are usually pretty good indicators if someone is interested, if they are saying them or responding well.

Within an hour of talking, she said she didn’t have much time before she needed to crash for the night and if her being married wasn’t a problem, that I could join her in her room to hang out.

While we fucked, she kept saying how she should really stop and get to bed, but we kept going.  We spend twice as long fucking than we did getting to know each other.  I asked her if she cheated often and she said she cheated when she could and her husband doesn’t know.  It started off as revenge for him cheating, but she has cheated since her first episode.

Once you start, you can’t stop.  The thrill of the cheat is intoxicating.  Sometimes it is a connection with one specific lover. Sometimes it is the variety of fucking new people that do not care about your marriage.  You just need that you can love your husband while also enjoying the attention and dominance from another man.  You can hide everything except impregnation, so be careful.

Back to school moms

Back to school season was and still is kind to me.  I’ve had some moms proactively reach out and plan some day-dates since they have an empty house to deal with.  It’s hard to find time to get together with some stay-at-home moms during the summer with small kids running around.  After a summer of lacking time to sneak away, it builds up to the weeks when kids go back.

The short of it is that I had some sexy time with some local moms.  One mom had a traveling husband, so I went to her place without fear of having him walk in on us while we were fucking.  I have some day-dates set up for this week as well, as I fit it in with travel. I’m sure I will elaborate more on the subject as I have some time.

I wish there was something more crazy or wild to report with each of the encounters, but there wasn’t.  The ladies said they enjoyed getting more dolled up in a sexy way than they had in months.

I can tell, you’re not doing that on purpose at all.  Your slow clicks; pretending to peruse some content.  You intentionally burn seconds and play with your hair, pretending to sound miffed, like you are having trouble with something.  The look you give me over your shoulder as I catch your eyes says that you know you’ve been caught.  I say something innocuous that couldn’t be misconstrued as harassment, like, “we should get a drink.”  It lets you know that I am on to your game.  I don’t ask; I say.  Asking gives you an out.  Saying and stating lets you know that I know you’re a coward if you end your flirting right there.  Make an excuse to your boss why we need to step away.  Tell your husband that you’re working late.  I don’t give a shit.  Figure it out and feel your heart pound as you meet me for that drink.

Conference cheaters

I’m at a conference for work this week and Monday night, a coworker and I met two women that were also coworkers and they love to party.  We’re mid-30s and they were mid-late 20s.  My coworker is married, but cheats on his wife.  One of the women has a b/f and the other is married.  The married woman was the big flirt and the one to suggest partying up in her room.  When we were up there, the woman with the b/f was flirty, but kind of reserved.  The married one was making out with me while my friend was talking to the other.  My partner reached down my pants and pulled my cock out, enjoying seeing the size of it grow in her hands.  She happily sucked on me and let me spread her legs to fuck her.  It was hot hearing her complain about her husband’s small cock and telling me how much she loved mine; how it hurt and stretched her.

I pulled out and my coworker took my place, fucking her.  I went over to the woman with the b/f and she giggled nervously.  I sat next to her, looked into her eyes, let her nervousness dissipate with some joking around.  She settled down and I kissed her.  She kissed back.

We kissed for 10 minutes or so and I started caressing her, which she was open to.  I grabbed her and pulled her onto me as she straddled me and grinded on me through her panties under her dress.  She was wet, I could tell.  She kept saying that she shouldn’t.  I told her to tell me to stop if she was uncomfortable.  She said she was ok where she was.  We grinded a little more and I asked her if she was wet (obviously).  She said maybe.

We kissed and I starting pulling her thong aside.  She kept saying, “I don’t know.”  I asked her what she didn’t know and she just repeated the same thing.  I told her she could stop me, but again she just said, “I don’t know.”

The head of my cock pressed against her pussy lips and she kept saying, “I don’t know...”  She knew.  She slowly let herself slide down on me as I stretched her tight pussy with my big cock.  She was so wet it didn’t take much to prime her and get into her as far as I could go.  I bottomed out in her depths and her pussy strangled my cock.  I told her she should let go since she already cheated.  She let go.

She is a dirty talker and I love it.

We’re meeting up again tonight.  Hopefully it’s just as good.

which is a more powerful experience for you: when the husband knows or when he doesn't?

When he doesn’t, especially if he is an asshole or abusive to her. The “I fucked your wife” power is strong.