Busy Week

So hot. I’d love to get a woman to wear it for me before she wears it on her wedding day. That’s still a goal and something I haven’t done yet.

She wore her bridal lingerie for another man..

No condom; lots of cum

Every so often I take a calculated risk without a condom. One of those nights happened tonight as a neighborhood housewife, who I fucked in the past, came over to hang out tonight. It starts out as grinding against each other, with a bit of alcohol in our blood. Her juices lubing my shaft up as she slides her pussy lips along it. We play Just-The-Tip and it goes along rather than it should. My big head disappears into her and we forget as her pussy stretches tightly on my big cock. She gasps and keeps taking more until I bottom out in her. I ask her if she ever cheated without a condom, she says no. She tells me to let her know before I cum. Eventually I tell her and she says, "Good," and presses herself on top of me until all of my thick load is inside her. She tell me that she loves it and through the night I find two more loads to shoot into the depths of her pussy. She loved it and said it made her feel like such a slut. That her bull deserved the honor of being the only cheat to not only fuck her without protection, but to cum in her as well. She admitted to fantasizing about it. She is such a fucking knockout that I couldn't help myself.

Is it wrong to keep trophies? I like to review and revisit pictures of conquests.

Separated; a COVID affair

Last year, I met a woman who (to this day) is going through a divorce. We met on a dating app, since she was feeling bored and lonely with time on her hands. My profile leaves no questions as to what I'm all about, so it does a good job weeding out unnecessary matches and interests. It's funny the way women will reach out to me. They fall into three buckets.

1 - They are blunt about their interests and the heavy-handed flirting kicks off right away.

2 - They match and talk to me like I'm any other guy, perhaps conveniently ignoring the darker parts of who I am that I'm pretty upfront about.

3 - They are shy and awkward, trying to find a way to be 1, above, but lacking the resolve or sexual confidence.

My new friend is a 3. Typically 3s are boring as hell because they cannot be honest with themselves. There is this song and dance they expect you to go along with to make them comfortable and oftentimes there is not a payoff because they don't know what to do with the comfort once they have it. I'm all about cultivating that connection and comfort, but I stop putting energy into conversations if I do not get any back.

My 3-Friend broke through that barrier quickly and jumped into being a 1. It was like unleashing a beast that wanted to be let out inside her. Very pretty girl-next-door that got married young to some pathetic dude that did not appreciate what he had. She's still pretty young and without kids, but she ended up getting a boob job since I guess her tits were pretty small before. It brought a spark to the bedroom, but that eventually waned. But where her husband attention dropped off, she was realizing she was getting attention from other guys.

In 2019 she worked a booth at a conference for work. The first night she hit it off with some guy at the hotel bar, let her guard down, and ended up fucking him back in his room. The first night was a shock to her as she said she felt an immense amount of shame walking back to her room. She thought it was a one-time and one-off thing and struggled with both feeling incredibly guilty and excited. She worked the booth the next day and a different guy was really chatty and flirty with her. He asked her to grab dinner and she went. They ended up in a lounge later that night, making out and fucking in his room. The next day was uneventful, but the fourth night she was relaxing by another bar since her work duties were done. She intentionally ditched her team to just see what kind of flirting was out there without prying eyes. She met a few guys, but she had chemistry with another and fucked him back in his room.

The experience changed her and she realized she needed to live a different life than the one she seemed unhappily stuck in. To this day, she still hasn't admitted much of that to her friends and she only fucked one more local guy before separating in the middle of the pandemic. After breaking down her walls, she very quickly moved to opening up about her experience with me the same night I started talking with her. I first matched with her and it took a few days for us to chat in real-time, but once the spark was there, there was no denying it. She was only a week and a half into not living with her man anymore and she was thrilled to meet someone she could confide in and not judge her. She knows all her friends would judge her or guys would feel threatened by her sluttiness, even if just a few moments in her life.

I let another week go by to make sure she wasn't the psycho type that wanted to quickly and desperately meet and she appreciated the space and time. We sexted regularly and decided to meet for coffee. We clicked quickly and I followed her back to her place. She gave me the tour and it was clear that she wanted to linger in the bedroom. She went to the bathroom and came back out with her rings back on and said that she knew I liked that kink. I just put my hand behind her head and grabbed her hair as I pulled her closer to kiss her. She pretended to resist and played along, telling me she shouldn't be a bad wife. I found her matching bra and panties with freshly shaved pussy, so she came prepared. I ate her pussy slowly and warmed her up for a while. I was hard when I stood above her and she laid down on the bed, legs spread. She saw how big my cock was and tried to hide her reaction. I ran the length of my cock through her pussy lips. She took a bead of my pre-cum and put it in her mouth. I teased her some more, mostly until she couldn't take it and she began to talk dirtier in her lust. I was breathing heavy and she started to kick me with her heels, trying to get her hips closer to me.

I pressed the head of my cock into her pussy and felt the stretch and heard her moan. She was dripping, but so tight on me. I wanted more and I roughly thrust deeper into her. Her intake of breath was sharp between her teeth each time. I fucked her and edged across positions to prevent myself from cumming and felt her waves of an orgasm take over her before my own. She could tell I was edging and told me she wanted me to cum in her. She assured me she was on the pill. I kept the edge going for a while longer, but eventually thrust deep into her while she was bent over, pulling her hair roughly as I came in her. I stayed hard and slowly thrust in her over the course of a few minutes to recover and I began fucking her again.

I ended up spending the night there and we have kept up the affair to this day. I've been a crutch for her to help her get through the divorce. It's great that she doesn't expect anything more from me other than the intermittent companionship and sexual favors.

You know its good when you need to change the sheets to hide a huge wet spot in a number of places so he doesn't find them. Just hope he doesn't see the cum-soaked panties that night.

Date night

Last night I went on a date with my mid-20s, single slut that I’ve been fucking.  Ton of energy and a cool-ass personality.  We’ve been fucking a lot lately and I declined her invite for me to be her NYE date with all of her friends.  It was a strong girlfriend-signal that I didn’t want to get into.  Anyway it’s hot because as we kiss and engage in foreplay, we share stories about our adventures.  She has a gorgeous girl-next-door face, big and unreasonably (and real) perky D tits, and petite frame despite her strong, dancer thighs.  She loves sex too much to not fuck guys after a date or two, so she has had trouble with guys only using her for sex.  Kind of like me, I guess.  We do more than just fuck, so maybe not like me.  Who knows.

Anyway, she shared stories as well as some pictures and videos of her sexual adventures.  Very hot and I showed her some of my own media, mostly of cheating wives.  Her hottest story was from two years ago when 7 guys fucked her as part of a bachelor party.  She went to a strip club with a group of friends, chatted up some guys, exchanged numbers with one of the guys, and instead of going home, she went to the hotel where the guys were staying.  Super risky since she was by herself, but she ended up making out with and playing just-the-tip with the bachelor.  The guys watched and cheered them on and she said fuck it, and sat on his cock down to the hilt.  Again, super risky, no condom and since she was on the pill, she let him cum in her.  By the time the bachelor pulled out, another guy had his cock out, ready to take his place.  All 7 guys had a chance with either her mouth or pussy, 4 of them were married, and 5 came in her pussy and 2 in her mouth.

For the next almost-year after that, the guys reached out to her to party, be it for a birthday party or whatever, each time ending the night with a gangbang.  One guy got caught cheating with another woman and it freaked out the group of guys and all but one of them ghosted her.  Lucky guys while it lasted!  Most guys have to pay for those situations!  I told her she could have made some money!

Really the moral of the story is that she’s a slut, lots of fun, and clean after STI testing!  I’m the first guy she told that story to, because she has been terrified of guys judging her slutty behavior and not wanting anything to do with her.  She said it turned her on to tell me as we were fucking.

Such bullshit.  They almost always come back.  It makes me even harder next time.  Yeah, you were done cheating?  Then why am I fucking you again?  Oh yeah, because you’re my slut.

Look, just put the guilt aside and spread your legs like a good girl.

In Chicago; Will travel

I have a lot of people reaching out to me about where I’m local to and if I travel.  I’m in the Chicagoland area and I travel all the time for work.  My travel includes mostly the domestic US and sometimes Canada (mostly Toronto or Montreal).  

-Yes, I’ve fucked married/taken women while traveling.  Often, to be honest.   -Yes, I’ve met couples and married women online to fuck.   -Yes, I’ve met women/couples online and during business trips in their area, fucked them (the women).   -Yes, I’ve fucked women/couples from Tumblr.

Guys

If you are reaching out and want me to fuck your wife - yes, I’ve done this before.  The vast majority of the time the setup includes her knowledge.  If you are expecting me to travel somewhere (or even as part of my own business trip) to just try to seduce her without her knowledge of the experience, then just know that those setups are hit or miss.  If she doesn’t know you are setting it up and has no idea that you are interested in it, she will very likely *not* engage with me if you are around.  Sometimes these situations require some cultivation over time, which can be difficult remotely.  Have I done it before?  Yes.  Many times; but mostly with couples/women local to me where I have the ability to be local and cultivate that connection for seduction.

If your wife knows that you want to set this up then its important to know if I would be a first for her.  Basically it depends how experienced the couple is in cuckolding, sharing (vixen/stag), etc.  I will *NOT* meet any couple quickly and without getting to know them.  I’ve had a lot of my time wasted in the past or strange situations where the guy is a lying about the situation, the woman isn’t really into it or she doesn’t know what is going on.  I will *NOT* meet any couple where I’m not very physically attracted to the wife. I know, I’m an asshole, but I own it.  I enjoy fucking married women, but I don’t just fuck anyone.  I need to be very attracted to them.  They wouldn’t waste their time with me if they weren’t very attracted to me, right?  HOWEVER, regardless of attraction, I’m happy to talk with couples about the situation and provide recommendations on how to go about things.  Everyone can use more friends; right?

I am not into anything sexual with men.  You can watch, you can clean up after me, your wife and I can talk dirty to you; whatever.  I’ve had men try to ask me in the heat of the moment to do something with them and the answer will always be, respectfully, no.

Ladies

Thanks for reaching out and continue to do so.  I love hearing your stories and the different walks of life or situations that you are in.  Like men/couples above, I will not meet you quickly.  I need to get to know someone before I meet, single, taken, married or whatever.  I’m happy with one night stands when traveling, but when I meet someone off the internet, there needs to be more there because there is so much that can be hidden as we connect only online.  I am 100% discreet and am not looking for any connection other than friendship and sex.

That’s really it.  I love talking to and meeting new people, so continue to reach out.

have you ever had sex with someone who is happily married? like someone who is married for like 20+ years? If so, how did you get her?

Of course.  In fact women that have been married for that long have either cheated and are looking to again after a while or they are open to experiences after being with their husband for so long.  Usually those relationships don’t have as much passion and a woman enjoys the spark again.  It’s dangerous though, because those passionate moments are intense and addictive.  I’ve seen completely true-blue, married women, moms and all, turn into slutty lunatics that start to have sex consume their thoughts and energies. Those women honestly take more risks. Things from letting their guard down with hints that husbands may pick up on or worse - being neglectful toward their family.  I’m not trying to break anything up; especially if women have kids.  Thankfully my travel is a natural barrier from someone always wanting to meet and multiple times a week.

Don’t get me wrong, not all women that are married 20+ years are like that.  Of course that isn’t the case.  I get a LOT of questions like there is some silver bullet that makes women drop their panties.  That’s simply untrue.  Yeah, there is a method to the madness to not be a fuckboy or douche, but it only works with women that are already open to those thoughts.  You can’t physically make someone do something and overwhelm their rational thoughts with words when, at their core, they don’t want to.  I’ve had a lot of failures here and seen women flirt, but then get awkward and bail when things progress.  That’s cool.  I don’t push it because those women aren’t feeling it or they aren’t the kind of women that want to cheat.

When women put themselves into situations where they let their guard down (alone, drinking, traveling, etc.), they oftentimes are open to the suggestion of cheating.  When they are completely in control of rational thought, they KNOW they are putting themselves in those environments and situations.  Consent is always a priority, so I absolutely do NOT advocate sexual abuse or assault.

That said, I’ve fucked plenty of women in their 40s that have been married for 20+ years.  When I was in my early 20s I had a cougar fetish and I loved pursuing married women between the ages of 35-45.  Now that I’ve entered that age range, it’s pretty easy to find women in that age range.  Not a lot of guys still commit to keeping in shape!  That and I noticed that women are more comfortable with my age because they assume it comes with more maturity than a guy in his early-20s (which the jury is still out for me!  hah!).

Event friend

A few months ago I met a friend of an acquaintance at an event.  There was alcohol involved with an open bar, so inhibitions were lowered enough to get her alone, flirting, and her number.  She was invited by her friend who I am only acquainted with and don’t really know well.  She is married as well, so it allowed her to let her guard down with the alcohol and flirting.  The event was large enough to where we were not worried about crossing paths with our mutual friend.  It didn’t go farther than flirting and “innocent” brushing against each other, but the chemistry was there.

Over the months, since we met, the texting would come and go in spurts.  The content of our texting was flirtatious and dirty, so a lot of it needed to be hidden from her husband and not while kids were around.  The conversation would turn very dirty and sexual when she was traveling for work.  I got her brave enough to send nudes and call me to talk dirty when she was alone in a hotel.

Recently she texted me on a Friday asking if I had dinner plans.  I didn’t so I agreed to meet up.  I asked about the hubby and kids and she said that he just left to go out of town on a weekend guy’s trip.  She planned for the kids to stay at her parents’ place for the weekend.  Dinner was amazing, without any awkward moments.  She warmed up quickly and flirting kicked off right away and the chemistry we had over text and calls was the same in person.

She invited me over to her place after dinner and we made out on the couch for over an hour.  She straddled me and ground her crotch into me.  I took her skin-tight jeans off of her and left her thong on, pushed to the side, while I knelt between her legs to taste her pussy.  I took my time with her and my tongue felt numb by the time I got her to almost climax and edge, as I didn’t let her cum.  I pulled away and pressed the head of my cock into her wet pussy, which despite my size, she took well and eventually bottomed out close to my hilt.  In the moment, she willingly initiated dirty talk and told me about the other guys she has fucked since getting married.  I carried her up to her bedroom and fucked her, even feeling her squirt on me once, getting the bed wet.

We ended late and on my way out she said she asked if I wanted to meet up on Saturday night as well.  I told her that I was game if she could take more and she said that she wanted more, regardless of what she can take.  We made plans to meet up for lunch and I told her I would take her lingerie shopping.  We met up for lunch, which went well, and we went to an adult store to find some lingerie to wear.  We ended up with a teddy, some stockings, and a dress to go over it all.  I told her I wanted her to role play being a stripper for me and she loved the idea.

We got back to my place and she got dressed.  She came out and danced for me.  We shared some drinks and she straddled me to grind on me again.  This time I could feel her wetness emerging through her crotchless teddy.  When I tried to put my hands on her tits or pussy, she would push me away saying that it wasn’t allowed.  I touched her sides and massaged her shoulders.  I wanted to feel her in any way I could, as I was being driven wild and insane with her scent from her neck and hair in my face as she ground on me backwards.  She left her ring on and I asked about it.  She said that she was married, but was given the green light to strip because of all the money it brought in.  The rule was that regardless of what the house allows, hands are not allowed on her tits or pussy.  Whenever I tried to touch, she would gently push me away.

This went on until she took her dress off to reveal the teddy.  I grabbed her hair and kissed her roughly.  She allowed it and then pushed me away saying that it wasn’t within the rules.  I asked what the rule was on kissing and she said that she wasn’t allowed to kiss anyone.  I put my hand on her mouth, pulled her hair with my other hand to pull her head back, and kissed her neck, shoulders, and eventually down her to tits.  I let go of her mouth and she said that I shouldn’t, but I said that the rule didn’t say that *I* could not kiss her, just that she could not kiss me.  She thought about it for a second and agreed, letting me continue.  I pulled out some nipple clamps and told her to put them on, which she did.  I noticed that all the rules she had with her husband were that she couldn’t do things, but outside of my hands, I was allowed to do what I wanted.  I didn’t touch her pussy with my hands, but my mouth and tongue did...greedily.  She didn’t protest.  

I pulled off my pants and she asked what I was doing.  I said nothing, but that I wanted to touch her without my hands some more.  She said that we could get busted if someone saw us.  I said that we already had an audience of people in another private booth watching us.  She said we should stop because she didn’t want to get in trouble or have her husband find out that she was bending the rules.  I put my hand over her mouth again and made her put part of her dress in her mouth as I tied her hands together behind her back.  I told her that our audience was watching and the guys were stroking their cocks looking at her and what I was doing to her.  I put her on her back, dress partially in her mouth and she pretended to struggle as I spread her legs, holding her hands over head with one hand and holding her torso down by her neck.  The tip of my cock found her cunt and I pressed inwards with thrusts until she took most of me again.  She pretended to struggle some more, but eventually gave in.  I told her to look at the audience and she played the role.  

I asked if she recognized anyone and said her husband was one of those watching.  That he set me up to see if she would break the rules.  That he stroked his cock while watching his wife turn into nothing more than my slut in the dark moment.  She came twice and the sex was amazing.  After the first time she came I untied her and she took control instead, which I’m not entirely used to.  I had a condom on, but she role played that she was talking dirty to her husband that I was bare inside her and she was going to make me cum in her.  We pretended that her husband protested, but she was determined.  That she was fertile and she wanted him to watch a stranger get her pregnant.  I definitely came and filled the condom to the point I was surprised that it didn’t break.  Her second orgasm came while my cum-filled condom was still inside her.

We took a break and she spent the night at my place, fucking again in the morning until she had to go home.  She was a fucking mess by the time she left and her pussy was sore.  I took it easy on her in the morning.

She has since been more aggressively sexting me, but I’ve had to tone it down in how quickly I get back to her because I don’t want her to take any stupid risks.

We fucked again since and it was great.  No in-depth role play, but she wants to do more the next time her husband is out of town...and no, he DOES NOT know that his wife is my slut.