I Hooked Up With an Older Lady From the Bar for Money, and I Hate Myself | Reddit Stories

I hooked up with an older lady from the bar for money and I hate myself. Posted by you one_metalbad_man. So this has been happening for over a month now, but the gravity of the situation just hit me today.

So I, 31M, am not in a great place in life right now. I was doing great in my mid20s, but alcohol and gambling have turned my life into living check to check. I work two jobs.

I'm single, have no kids, but I'm still in a hole of debt. I did save quite a bit of money into retirement funds in my younger years, and perhaps I'll have to take a loan out against it soon to delete other debt, but not yet. I frequent a bar that's across the street from my apartment.

Most of the regulars are now friends, or at least familiar acquaintances from as young as 21 to as old as 75. One of my good friends, Lynn, who's a regular at this bar, is in her 50s, and she's beautiful, especially for her age. Literally any guy at the bar would take her home if she ever let them.

Lynn lives close to me and I've started hanging out with her outside the bar. It's always a fun time when it's just me and her, but some of her friends are a bit much. Most of her friends are older single women who like to drink heavily and live loud.

One friend in particular, Barb, clearly took a liking to me the first time Lynn introduced us. She was rather upfront about how attracted she is to me, but she's older than my mom and I'm not attracted to her in the least. Barb apparently also lives close by Lynn and me and she started to go to the bar and always sat next to me.

It was nice at first and she always bought me a drink or two, but she really started to become a buzzkill, especially because I couldn't hang out with Lynn without Barb being there, too. And I missed it being just Lynn and me. Now, don't get me wrong, Barb is actually pretty hilarious and a fun time, but just knowing how badly she wanted to sleep with me always made me feel a little awkward, especially because I had a crush on her friend.

So, about 3 weeks ago, Barb texted me and asked if I could help hang up Christmas lights in her apartment. She said I could drink and eat anything at her place if I helped her. I was a little drunk at the bar when she texted me and had just gambled away the rest of my cash, so I obliged.

Barb lives in a building that just opened up this year and I had been in it to visit a friend before. Very upscale apartments, great views, brand new. However, what I didn't know about this place is that they had some crazy condos in that building.

So, I got to the top floor and her place is huge. Everything was so nice. The ceiling was so high.

There were stairs that led up to her bedroom. So, I told her how amazing her place is and she immediately spilled out her life story. This was a bit weird because for as long as I'd known her, she never really opened up about herself much.

Anyway, nasty divorce. Still in court with her ex-husband. One daughter talks to her, the other doesn't.

She's sexually starved. That one hung in the air for a bit. I listened to her, told her how sorry I felt for her, helped myself to a few beers, and began hanging Christmas lights in her windows.

She has tons of tall windows, so it was taking a while, but we were laughing and having a good time and getting drunk. For 9:00 p. m.

on a Wednesday, I was irresponsibly drunk. I still don't know why I did this, but she asked if I wanted to take a shower with her, and I did. Didn't even have clean clothes to change into.

So anyway, we were showering and I wasn't impressed with her naked body, but for whatever reason, I got excited down there and she immediately grabbed my thing and started feeling it. I told her that she can touch it, but I don't want to have sex with her. We went to lay down in her enormous bed.

Actually, her whole room is huge. Her place is amazing. So, we were watching Young Sheldon or something, and she flat out asked me, "What would it take to get you to lick my PC?

" And for some reason, in my drunken stouper, I immediately responded, "20200 bucks and a frozen pizza. " She looked at me with a dead serious face and said, "I'll give you 400 if you make me CM. " Oh crap.

She pulled up her night gown and yeah, I got $400. I actually really needed that money, so the disgust was just sitting in the back of my mind and I was able to ignore it for the most part. A week later, I got a text from Barb asking me to come over.

Once again, I was at the bar drunk and broke from gambling, so I walked over. When I got there, she asked if I wanted to have sex. I told her that I don't have sex without condoms, and she reassured me that she can't get pregnant.

I told her that it didn't matter. I always wear a condom. She respected that and then asked if I could eat her out in exchange for a BJ.

Awkward. I asked her if I could get paid like the last time, and she apologized and claimed she only paid me because she was so drunk and horny. We discussed the previous night for a while and she ultimately offered me $50.

I haggled the price up to $75. The whole conversation was so long, uncomfortable, and awkward I can hardly type this brief summary. I went to the bar that Friday and Lynn was there.

It was the first time in a while I had hung out with her without Barb being there, and it was great. I mentioned that I helped Barb hang up Christmas lights and was really impressed by her condo. That is when Lynn revealed something that raised my eyebrows.

Barb is rich. Like multi-million dollar rich. Like her ex-husband was rich.

Like she and her brother inherited land from their family and they just sold it for an enormous amount of riches. I knew she had to be fairly wealthy based on her place, car, and clothes. Then Lynn showed me pictures of Barb's house that she owns on the other side of the state, and holy effing crap, this woman's loaded.

I went to the bar all night for the next few days, waiting for Barb to show up and checking my phone constantly, waiting for Barb to ask me to come over. However, I actually won a hefty amount on the gamble machines and was able to maintain for a while. So, when Barb did hit me up to come over, I told her I was busy.

Of course, when you gamble, your winnings only last a few days, and I was broke, drunk, and high by myself in no time. Then, Barb hit me up again. It had been over a week, and she said she wanted to make a deal with me.

So, I stumbled over to her place, and when I walked into her door, all the lights were off except the Christmas lights, and she was naked. Barb said, "I need you inside of me. What will it take?

" And good lord was it cringey as hell. Now, this may be a good place to mention that I don't know crap about prostitution. I don't know what normal rates are.

I don't know what boundaries I'm supposed to have. Completely ignorant. But I knew Barb had millions.

Anyway, I asked for $1,500. She laughed. She said I'd have to last a long time for $1,500.

Cringe. She offered me $500 and I wasn't allowed to wear a condom. I didn't understand that part.

Do women feel that much of a difference if a condom is or isn't being worn? Why did that matter to her? I got her to agree to $800 with $1,500 being the price moving forward.

I don't want to talk much about the segs, but she was very satisfied. So much so that she asked me to come over the next day for the agreed price. Then two days later, she asked for a full service with a back massage, oral, and an hour in bed.

I asked for $5,000 just for craps and giggles, but she effing agreed. All of a sudden, I had made over seven grand in the past few days. I paid rent in cash, bought groceries, got my car fixed, and purchased all the Christmas presents.

And a welcome side effect of the constant hooking up was that I was gambling less, and spending less money on booze. I felt good, really was starting to accept the situation. I went to the bar in a great mood.

Lots of my friends were there, played some pool, smoked a joint in the alley. Great stuff. Then Barb came in.

She made her way around the bar saying hi to everyone, then sat right next to me and kissed me on the cheek. I'm stunned. My friends, who I was talking to, both dropped their jaws slightly.

She joined in our conversation and I felt my face getting red and hot. My heart was blasting through my chest. After a short while, I announced I had to go home and Barb asked, "Will I see you later?

" I don't know. Hit me up. Was my response as I got out of there.

This happened just 4 days ago, and I haven't been back to the bar since. I know that my friends know, or at least strongly suspect, that I've been hooking up with Barb. But one comforting thought came into my head.

They'll understand when I tell them I only effed her for her money. Then a cold realization flooded my brain. It will make it so much worse if they find out that I've been having sex for money.

I'm actually a whre, an alcoholic, gambling addicted WH. Now I think I'm just going to have to pretend I got drunk and hooked up with her for fun. This is the heaviest guilt and most insecure secret I've ever held.

I'm actually a piece of crap and I hate myself. I really effed up. If I just drank less and didn't gamble, I would never have gotten myself into this mess, but this is what my life's become.

Top/relevant comments. Commenter, I would be more concerned about the gambling addiction and alcoholism for sure. Commenter 2: Yeah, becoming Barb's personal jigalow seems more like a symptom of the addictions, not the actual screw-up here up.

you should probably take a good hard look at how you're living. Commenter three, I mean, this guy isn't going to get a better financial opportunity than this. He should work on quitting the drinking.

And if you got to gamble, learn how to play poker. Never gamble versus a machine or the house. You will not win long-term.

Only gamble versus people because people that gamble are generally idiots. Also, tap the f out of that old lady for as long as you can. You could literally change your entire life with the fortune you could make.

Easy, but shameful money. Just own up to it with your friends. Embrace the shame.

We're all whres for something. Commenter four. So assuming this is true, which I don't think it is.

I think it's a creative writing exercise. You tell your friends, "Yeah, I got really drunk and hooked up with her. I didn't want to be mean to her when she came up to me in the pub.

I'm going to let her down gently. I don't want to be a jerk, but I'm going to tell her that it was a one-time thing. " Then you go tell Barb, "This isn't a relationship.

Don't start acting like you're my girlfriend in public or we'll have to be over. This is not an insurmountable issue unless you let it be one. Update one year later.

About a year ago, I made a brief post about how I began performing sexual favors for money while suffering from alcoholism and gambling addiction. Many of you seem to enjoy my story, and some of your comments changed the way I approached and felt about my situation. Therefore, I thought an update would be appropriate, though it is quite a late update.

I didn't see or hear from Barb for about a month after our awkward run-in at the bar, which incidentally spawned the original post in the first place. I started imagining that she was paying someone else for sex. Turns out she was visiting her brother in Arizona for a few weeks.

During the time I hadn't heard from or seen Barb, I did not bring up anything to my friends who witnessed our previous bar interaction. When I made the original post, my biggest concern was how my friends would react to my situation with Barb. In all actuality, nobody brought it up to me, and I certainly didn't bring it up either.

I think they had their suspicions, but nobody treated me differently, and it was easier for me to cope with the scope of the situation. Barb hit me up one night, January of last year, explained where she had been and asked if I could help take down her Christmas lights. I came over and to my surprise, she actually just wanted her Christmas lights taken down.

I explained my actions for running away at the bar. And she said that after I left, she told my friends that she was joking and that she felt bad for making me uncomfortable. Apparently, they thought I was being a spaz.

I asked Barb to keep things on the deal in public, but she told me that she didn't want to move forward with our previous agreement. She said she got too caught up in the heat and pleasure and ended up doing things she now feels uneasy about. She said we could still hook up for fun, but she did not want to continue paying for sex.

It made her feel filthy. I didn't have any interest in a friends with benefit situation because I'm not attracted to her, but I didn't tell her that. I expressed to her that I am willing to remain friends, but that I'm only interested in sex with girls I'm pursuing for a relationship.

I told her that I've only recently found out that I apparently make an exception for money. I also added that if she changes her mind, and if I'm single, I'd be down to do it again. This in particular was a response I made to Barb thanks to some of the opinions I read in the comments of my previous post.

Some of you encouraged me to get that bag. At the time, I had been participating in a mostly dry January with some friends, so I was clear-headed and separated from gambling opportunities. It was nice.

I also made a major career shift which resulted in less pay but now I only work one job and the work rellated stress is practically non-existent. I still drink a lot but socially I still gamble but much less frequently and at much lower amounts. Barb hit me up once in February and once in March for my services now we see each other at the bar every once in a while.

We smile at each other, we talk and we laugh, but I think we're both past that part of our lives. Things have been going truly well for me and at the age of 33, I feel very positive. I'm not exactly where I want to be or where I could have been had I made better choices the past few years.

But I am happy with who I am, how I treat others, and where my future is headed. Top/relevant comments. Commenter, well done.

I hope you can further reduce the gambling and drinking. Commenter two, funny, my reaction is OP is still willing to be a hooker when called upon. still drinking, still gambling, and for the moment, he's just keeping a tight enough lid on it, so the habits aren't entirely self-destructive.

Dude is hopping around on one leg near a cliff on a breezy day, and the only comments I see are, "OMG, I'm so happy to read you've changed so much and are doing so well. " Ops response, "This is a whole year later, and I'm doing much better. I smile more, have my credit card paid off, I enjoy going to work, and I work out.

My life is so much better than it was last year. I still have my vices, but they aren't debilitating me anymore. Commenter three.

Keeping a tight enough lid on habits to keep them from being self-destructive is pretty much exactly what everything in moderation means, right? Do you think that in order to be proud of something, it must be perfect? What does that attitude do to your mental health?

Commenter four. To me, the op just reads as, "I'm mostly still doing all the crap I've always done. " And it's a big game of Russian roulette, whether it spirals out of control every day, so much more than I feel like I got a handle on these things, and I'm in the driver's seat as it relates to my relationship with gambling and alcohol.

And I hope I am wrong in the jerk for that interpretation. But I'm surprised the initial reaction of others is that this sounds like an update from someone who isn't one bad day from being at Square One. Ops response: I don't think this is an unfair interpretation.

At the time of my last post, I had just left an abusive relationship, put down my dog, and absolutely hated my jobs. These were the major factors that led to my behavior being so destructive. I feel like anyone can spiral out of control in the perfectly disastrous situation.

I'm hoping I will handle things better now if such a dark cloud comes my way. Commenter 5: Is that the dog in the videos on your account? Why did you have to put it down?

Ops response. For some reason, after I got him fixed, he became a very aggressive dog. He mangled a dog at the dog park and bit a child.

I tried to get him hardcore behavioral training, but everyone refused after hearing he bit a child. I tried to send him to a sanctuary, but they recommended I put him down. It was devastating, and many people, including on Reddit, called me a dog murderer and made Christy Gnome related insults towards me.