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The Jerk Journals: The Indecent Proposal, Her Man Said She Should Sleep With Me

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Photo By Mateo Bertolio

My name is Xilla, and I’m a self-absorbed jerk. It was by any means an indecent proposal. There was no money involved, no one wanted to sleep with my girlfriend and technically I wasn’t asked to do anything I haven’t done in the past, but I’ll admit I was a bit shook. I’ve slept with girls who were involved before. In fact at one time I only slept with girls who had boyfriends, and looking back maybe this was payback for all of those times, but when shorty told me she her man gave her permission to have sex with me, I was dumbstruck!

It all started when a former Cinderella came to vacation in New York City. She hit me on facebook, and a few days later we were sitting down having a late lunch. I wanted to rekindle the spark we shared many moons ago, but over the years she had a baby with another man. That baby was sitting on her lap, and I could tell in her eyes our relationship had moved back to the friendship zone where it belonged.

I tried any way, and let it be known that while she was in town we should bump and grind a little more. I reminded her of how great it was and while I tempted her, she wasn’t about to cheat on her man. We hugged, went our separate ways and a few days later she gets on facebook and what happened next, left me perplexed.

In the course of conversation she said “My boyfriend said I should of had sex with you” I laughed out loud, replied something like well next time you’re here we should do the 14 new positions of sex that will leave your toes looking like Quasimoto’s back! She laughed and explained that her boyfriend said “If she wanted to, she should have fucked me, and as long as she told him about it, he would have been cool with that.” My brain started doing the cook up dance, I am Pusha T’s tangerine suit.

In my ignorance I put on some macho, ‘I’m the man music’ and continued our conversation then went about my day. She wasn’t close any more so it was all for not. Then she hits me on facebook again. Tells me it’s her boyfriend’s birthday and ask me what can she do for him to make his born day special.

I give her this whole drawn out plot on how to sex her man up. A few days later she hits me up again, and I ask her how it goes. She said she didn’t the plot I gave her b/c she was too shy so she just let her man stick it in her ass.

My jaw dropped, now she’s an anal queen! I laughed even louder this time, people from the next office came over to see what I was laughing at. It’s something about when someone laughs super hard that makes other people around you say, “what’s so funny I want to laugh too,” but I digress.

Again in my macho man ignorance I start thinking, if she’s giving up the ass then I should be able to stick it in her ass too. This is when she lands the bombshell. She old Roy Jones Jr’d me when she tells me “you can stick it in my ass, as long as my man can watch.” My face crunches up like a raisin, tilts to the side and I look at my computer screen like it just told me it ate out my mother. What the fuck?

Again in my macho arrogance, I say something slick and she comes back with, he might join in. I tap out, I hit the canvas. I’m a sexual Intellectual but this is too much.

Ok wait. First of all I’ve ran a train before. My boys and I would get a chick and each have our way with her, but these were my boys. I clearly knew what they were about. This guy I know nothing about. He’s a stranger, and this whole swinger lifestyle isn’t really my cup of tea. I’m not about to play the joust with my ManXilla. While I know sometimes you need an audience, I am not about to ask about another man’s role in my sex life. We are ‘pose to take turns fucking her in the ass, and then what? I’m sorry! No, not for me. I have to gracefully bow out of this one. But I would like to know what would you do in his situation?

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10 Responses to “The Jerk Journals: The Indecent Proposal, Her Man Said She Should Sleep With Me”

  1. Sexy26 says:

    Lmao… She scared the Xilla… Damn! Her man dnt mind sharing (I wonder what’s the reason behind that *scratches head *)…she should have just give him a 2 girl threesome instead of asking u but clearly u remind her how good the manxilla was and she wanted y’all both…haha…go get em tiger dwfl…

    • SQUIRTER33 says:

      XILLA!!!! I’m shocked that u aren’t up for this challenge. While I pride myself as being an INTELLECTUAL (sexual that is) am also bi and have been a swinger for over 7 years. I think it’s a thrill knowin you runnin up in sumthin that belongs to somebody else…however wouldn’t it be nice to have those permissions to do as you please? AND IN THAT BOOTY TOO!!! Man u better climb her ass like a gorilla!!!!

  2. LetsFilmThis21 says:

    Lmao. This is hilarious but I agree with you. This one was completely out of left field. I wouldn’t have done it either. I mean, who knows what kinda freak this man is?? He probably would have tried some shit with you then this story would have had a completely different ending. Lol. Still funny as hell though.

  3. LetsFilmThis21 says:

    Lmao! This is hilarious but I agree with you. This one was completely out of left field. I wouldn’t have done it either. I mean, who knows what kinda freak this man is?? He probably would have tried some shit with you then this story would have had a completely different ending. Lol. Still funny as hell though.

  4. G says:

    Haha! My 1st thought was that if he’s giving her permission then he’s probably cheating. My 2nd was that dude is into some seriously freaky ish if he was the one who initiated the three cause y’all don’t know each other from a can of paint. I can’t think of any man that I know of who I was sexually involved with who would go for a 3 with a guy I had slept with. Maybe someone I was interested in but not a dude from my past. JUST SAY NO!

    • Xilla says:

      Yeah that’s my thing. If I knew dude… it would be a totally different situation, like yeah we can run a train on ole girl. But I don’t! Weird!

  5. LS says:

    Her man may have a thing for you, You never know she may be trying to bait you so they can share … You did the right thing because you don’t know that man or his motives what you do know is it’s not a common practice amongst men to share their main thing with anybody… let alone a past conquest she obviously still has a thing for…

  6. ZY says:

    the phrase “running a train” seriously turns me off, just had to say that. lol

    as for this story… i was in TEARS by the time I finished it! I don’t see why you didn’t do it though. maybe her man was ok with doing it with you because she knows you and he wanted her to feel comfortable since you two had already had sex. that’s the way i surmise it anyway. lemme find out ole dude had the Xilla shook, LOL!!

  7. squirt says:

    I am currently dating a guy into the swinger lifestyle. I am not interested, but date him on the premise of honesty. Since women are usually viewed as the emotional creatures and men the physical ones many don’t realize that there are women capable of having sex without attachment. When you evolve to a certain degree it becomes about how much you trust one another, no the sex act itself. It’s mindset and I can say that I would prefer to be with a man that tells me who/when he is sleeping with another woman as opposed to a brother that’s creepin. According to them it’s like interactive porn…lol

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