I Read A Post Called The Event Friend. You Ended Up Role Playing As Stripper/customer. You Also Had Concerns

Boston Trip

Recently I had a work trip to Boston for a week.  I only had business out there for two days, but I stayed an extra day.  There is a sexy Tumblr friend that I met in person a few months ago, from New Hampshire, and she met me in Boston for the duration of my stay.  She is very married (is ok with me posting this as long as it is anonymous) and told her husband that she had training in Boston for the week and it was easier for her to stay there instead of driving in each day.  She obviously didn’t have training for work and took some of the days off to enjoy her time away from husband and two kids.

She met up with me later in the day on the first night and attacked each other in the room.  During our time together, she played dress-up for me and wore a few, various dresses and new lingerie that she picked out while I was at meetings.  It worked to get us hot and bothered for her to send me sexy pictures of herself while I was busy.  She even wore a jeweled buttplug and one night I spent some time working my cock into her ass for the first time.  It was a very sexy time that required patience, but I thoroughly enjoyed the experience.  She was gorgeous and amazingly tight on me, especially as she came when her ass squeezed my cock.  The dirty talk took over and was amazing as she begged me to cum in her ass, which I did.

Overall, it was a great time and a good mini-vacation for my friend from her familial duties.  It was great how the week was so hot, it spilled over into our sexting to one another and planning another trip out there.  Her husband missed her and she fucked him the night she went home, despite feeling sore, but she wouldn’t let him cum in her, because she still wanted to feel owned by me.  To this day, it still makes my cock hard thinking about how he had no clue that his wife’s pussy was used and claimed with loads of my cum.

Great time and great friend.  I love to travel and meet new people!  I can’t wait to go back to Boston!

Facebook Acquaintance

I finally fucked a Facebook acquaintance that I’ve been flirting with since early-summer. I met her at a golf outing that she ran (vendor-side) for my company.  She added me on Linkedin and eventually on FB.  I saw, in early summer, that she posted a few sexy bikini pics of herself on vacation with her husband.  I sent her a PM, complimenting her, and we sort of flirted on and off.  I thought it was a dead lead, but once in a while we would joke around and reconnect.  Anyway, she posted some pics on FB this last weekend from a Halloween party that she went to as a sexy mermaid.  I reached out with a private message again and the flirting resumed.

On Monday, she was on a business trip and she sent me a pic of her getting dressed for her meeting and asked if she still looked good out of costume.  She did, but I just teased her with non-committing answers.  Eventually I told her that I’d have to save that picture for later.  She asked why and I didn’t respond to let her think about it.

Later that evening, she drunkenly sent me a pic of herself in her bra and panties and told me that I should use that pic instead.  I said it was too late.  She immediately Facetimed me and wanted to know what I meant.  I told her that I already jerked off to her other pic as well as her other pics that she posted on Facebook.  She said at least I’d have that recent pic for the future then.  She told me it was a shame I already jerked off and then she slowly pulled her tits out of her bra.  I pulled my cock out and let her see as it came to attention.  She was very interested...I jerked off and she played with her pussy as we played show-and-tell while talking dirty to each other.

She told me to not tell anyone and that her husband couldn’t ever find out.  I told her it wasn’t a problem and that I never fuck and tell.  She said, “But we didn’t fuck!”  I told her, “Not yet, but I’m going to fuck you soon.”  She asked how I could be so sure.  I told her to deny that she wanted it; she couldn’t.

We made plans to get together after she got back from her trip on Tuesday afternoon.  Her flight got in a little after noon and she came over with time to space before her husband got off of work.  We started making out the second she walked in the door...

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.

So, when traveling and I meet a single woman, I'll oftentimes flip the script. Even though I don't have a ring, I'll pretend and sell a story of being married.

Sex addiction

Someone I’ve been fucking lately started probing and asking me questions about myself.  Things like, why I do what I do.  The topic of sex addiction and maybe understanding where my promiscuous and taboo-seeking nature comes from.

I haven’t seen anyone professionally about this, but I will say (and many of you can deduce) that I’m addicted to sex.  I always seek it.  There is a form of validation that I receive when I fuck new women, sure.  It comes in the form of a thrill that I’ve attracted someone to the point that they will fuck.  The taboo is interlaced with it in that I validate my own sexuality when someone will cheat on their husband with me.  I see attractive women with wedding rings and I get hard.  I feel compelled to talk to and flirt with them.  I’m an attractive male with a big cock that makes a lot of money in my sales job.  It makes it relatively easy when you couple that with my confidence.  I feel that validation when I see a woman’s eyes and absorb her responses to flirting.  I feel it when she feels my hard body against hers and she appreciates how I look and feel.  I feel it when she sees the size of my cock.

That winning feeling of beating her husband because he isn’t giving her what she needs and (in the majority of situations) he simply cannot give her with an inferior cock.

I work out because I love it.  The endorphins I get and the high of working out is an addiction as well.  It’s the thrill and the feeling that just pumps through your veins.  It makes it easy when one addiction helps the success of another.  Thankfully I don’t have an addiction to any hard core drugs, although I’ve met a fair number of women who love to couple drugs, like cocaine, with their cheating habits.

There have been times that I tried to pull away from this lifestyle, but the addiction is too strong.  I have no anchor, as only a few close friends know about my vice and those that do are fucking me.  This isn’t something that I can easily and readily share with close friends, due to the immense level of social judgment that comes with the territory.  I travel often for work, so I’m oftentimes in random cities by myself and unless I lock myself in my hotel room, I am like a kid in a candy store, hopping from location to location, looking for interesting women to meet.

I’m not looking for sympathy, I just have this blog to vent my stories and experiences.  It’s good for me to tell my stories and be able to have a level of anonymity that comes with it.  I plan on sticking with this lifestyle for as long as I can.  I have zero desire to get married and make enough money to be that old rich guy on a boat, inviting women to come travel with me.

Thoughtful day.  Don’t try to stop me.  Come play with me!

Cheating wife on the 4th

My friend had to work on the 4th, which sucked for him, but it allowed me to get together with his wife.  He doesn’t know, but she came over shortly after he left and brought a shaved pussy and matching bra, panty, and stocking set with heels.  She wouldn’t let me touch her until she got dressed for me.  My friend hadn’t fucked her since the last time we were together, which wasn’t too long ago, but it is a waste of a beautiful woman with long black hair, flat stomach, petite little butt (although I prefer them bigger), and fake tits.

We kissed and our lips were devouring one another and I grinded on her until I couldn’t take it anymore.  I took her bareback with my hand pulling her hair and we fucked for 2 hours before we had to peel ourselves off of one another. 

She showered at my place and we went to a 4th of July party at a mutual friend’s place.  Her husband showed up after dark and he has no clue.

Team Meeting and Hookup

A few months ago, I was traveling with my larger sales team to get together for a week. There is a coworker I have low-key flirted with that lives in another city, but never met in person. We both flew in the day before meetings, from separate cities, and hung out. We went to grab an early dinner after we checked into our hotel with a lot of flirting in the cab and during the meal. We had a few drinks to loosen up and when we hopped in a cab she went in head first and just shook her ass at me and refused to move until I grabbed her and moved her playfully.

We grabbed a bottle of wine and went back to her room to hang out since she didn't feel like being social with everyone in the lobby. Back in her room, the flirting was always on this edge of inappropriateness, because shit can get really weird with coworkers. She went through her carry on and intentionally tossed her panties and bra on the bed while she was looking for something. I grabbed the pair and asked her if her husband bought them for her. She laughed and said no and asked if I liked them. I said yes and that I was going to keep them. She said I had to earn them. I told her to come over, which she did, and I she knew what was up as I kissed her. We made out for a while and I asked her if I earned it yet. She said I had to try harder than that. I asked how hard exactly. She said harder than than her husband, who doesn't care about her panties.

The kissing continued and hands roamed across each other. I laid her down on the bed and spread her legs, pulling her panties off, and took my time devouring her pussy with my hands feeling her ass, hips, tits, and greedily groping for more.

She reached down and motioned to for me to move up, so I slowly made my way up her body to kiss her hard. I asked her what she wanted and why she wanted me to stop. She said I knew. I told her I wanted her to say it and she didn't want to. I had my cock out and I put the tip of it against her clit and her wet slit and told her to say it. She said no. I leaned my weight on her, grabbed the back of her hair, and told her that she needed to tell me what she needed because I'm having a hard time understanding. She told me through gritted teeth that she wanted me to fuck her and I pressed into her roughly. She was already wet, but the tightness eventually subsided as I continued to plunge into her.

I asked her if that's what she needed. She whimpered a yes and asked why it took me so long to get the hint. I said I had to play my cards right with coworkers, because you never know. She said well now I knew that I could use her pussy whenever we were on the road. I asked her if it was her first time cheating on the road and she said she fucked 8 other guys in the past three years when she started. I asked her her husband knew and she said he didn't. We spent a few more nights together and it was a great week. I haven't seen her again since, which is a real shame. We have sexted on the side pretty frequently though. I took two pairs of panties home from her as a trophy.

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.

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.

Coworker Escape

I recently met a coworker on a business trip.  It was actually just her and I working a deal and we were staying a few nights together.  She is married, but the trip gave us a get-away together.  It’s great to have a love nest to get away.  It’s better to be able to not have to deal with the anxiety of being on a schedule when cheating.  Cheating while traveling is the best.  She’s in her late-20s and no kids.  Easy for getting away and not worrying about anything domestic or having to call home and check up on things.

When we met up it was mid-morning and we didn’t waste much time.  The greeting hug went to a kiss, which turned passionate very quickly.  The foreplay and wandering hands went on until she pulled herself away to use the bathroom.  She came back out in an iridescent outfit that was part sexy clothes that may fit in at a rave and part lingerie.  It was skin tight on her petite frame and she danced for me, sexy heels and all.  She straddled me and the foreplay with wandering hands continued.  There was no penetration, but the building tension was so hot.  You know the quick, sharp, shallow breaths you have when you’re excited or turned on?  You feel that on your ears and neck and you just feed that energy right back at the other person.  It was intense with interlaced dirty talk.

Our first session started with so much foreplay that we lost time.  By the time I ripped out the crotch of her outfit, my cock had been hard for a long time, begging to fuck her, which her wetness reciprocated the feeling.  It was slow at first, but the fucking picked up the pace.  I would change up speeds to slow things down just to be still with my cock in her as I massaged her back, ran my fingers through her hair, or gently let my hands just explore her.  I edged multiple times, slowing down for the hopes of a bigger orgasm, knowing my pre-cum was seeping into her pussy.  It was a very gentle, but sometimes rough experience.  When I finally came, it was an amazing load and release after edging for so long.  After we both came, we just laid there and enjoyed the silence.  We eventually went to take a shower and fucked her in there as well.

From there we got some work done, we fucked again after dinner and chilled.  The next day we went to the meeting with our client and took them out to dinner.  After our client excused themselves, we went back to the room to play some more.