Sex in exchange for something (should I cut my loses?)

This is kind of a twisted story so I'll give the basics before I get into the meat of it.

I'm a 55 year old male and yes, I use the services of escorts from time to time. I have a regular girl I hook up with a few times a month or so and pay her a little bit for sex. She gives me what I want and I give her what she wants. Myu brother also uses the services of escorts but he is more into it than I am. He'll see a few a week spending sometimes $100 or more each time. For about a year or more he's been involved with this one girl. She posts ads and lets anybody get a ride as long as they pay. He started liking her and they sort of got into a relationship. She got pregnant by a client but wasn't sure who the father was and my brother thought it was his. He was happy. So much so that he began parading her around the family as his girlfriend. After the baby was born a DNA test was done and he wasn't the father. In speaking with him he told me that this particular girl was off limits to me, meaning, I couldn't see her. However, he would always send me the link to her ads when she'd post one so he pretty much gave me her contact information. They are constantly arguing and he'd tell me he was done with her only to get back together a few days later, even though she was still escorting, fucking everyone. I wanted to see what all the hype was with this girl and why she was so off limits to me so I hit her up. After texting with her for a while I told her who I was and that my brother told me she was off limits. She said that he has no right to tell her who she can and can't see. What we do is between us.

We linked up that night and it wasn't that bad. It wasn't great either but not bad. We have continued to chat ever since then. We've hooked up 3 times in the past few months. The first time was a paid visit. The 2nd time we linked up she had gotten a hotel room and she was smoking and was high. Apparently no clients were hitting her up and she was horny so I rolled through and hit it for free. A few months later she needed the brake pads replaced on her car so she made a deal with me that if I changed her brakes she'd let me hit again for free. No problem, changing brake pads is an easy job so I helped her out and she helped me out.

At one point, she ended up staying with my brother at his place for like a month and he'd leave her in his apt while he went to work. I literally asked him what would he do if he found out she was seeing clients inside his place. My brother is do naive that he literally told me that she couldn't because she didn't know his address. Duh, how hard is it to ping someone your location on your phone OR since you're already in his apt look for a piece of mail in a drawer or just laying around. A few weeks later they had a falling out and he had to call the police on him to get her out. Later she told me that she had fucked several guys in my brother's apartment when he'd leave for work, on his sofa, on his counter top, and I'll bet you they even fucked on his bed.

She found a job doing housekeeping at a hotel and for the past few months she's been telling me how this one guy who also works there has been fucking her during the day while they're at work. He'll trap her in one of the rooms and they'll fuck. She's loves getting fucked and doesn't care when or where. This guy has fucked her quite a few times at work. She's told me that the neighborhood guys have fucked her while hanging out with her outside her and her mom's place. She's what you would call the neighborhood jump off.

Ok, here's the meat of why I'm typing this. Last week I was sitting at home on my day off and she hit me up saying that she was sitting on the side of the road with a flat tire and asked if I could come help her out. She offered that if I paid for a used tire she'd let me fuck for free 4 times. I drive across town where she was, take the tire off and throw it in my SUV. Drive to a used tire place close to my place and pay for the tire then drive her back to her car and change it. She rarely wears panties so this particular day all she had on was a long flowing type of sun dress. I asked her if she had on panties and she said no so I told her I wanted to play with her while we were rolling to the tire store and back to her car. She lays the seat back, kick her leg up on the seat and I started fingering her. I did that both ways. Even while sitting in the used tire place waiting on the guy to put the tire on the rim. We literally were sitting in my truck, she had her legs up and I was playing around. Anyway, I get back and change her tire. She tells me that she was on her way to get a room and she'd tell me where it was so I could swing by later. Since then I haven't been able to tie her down to link up. We text almost everyday and she'll tell me about the clients she sees but when I ask when can I come over she seems to catch an attitude with me. Screaming about how she's gotta make her money first then I can swing by but she never texts me to say she's ready. Every day it's something different. Yesterday she text me to say she just woke up around 11:30 am and she was going to shower then go get something to eat. She asked if I wanted to go with her then we go back to her room. She asked if I wanted to just take her and she just ride with me. I said sure and I was on my way. Halfway there she calls me saying something came up and she would just go get her own lunch then call me when she gets back to her room around 2:30 or 3. Yeah, that's 3 hours later. I can see the writing on the wall. I'm sure some paying client hit her up wanting to see her so she opted to make money over following through with our deal. Around 3 I hit her up to ask what she was doing and she then tells me "I'm ordering my drink now." So at 11:40 when you first hit me up about going to get lunch what have you been doing since then. Yeah, she probably saw a client or two and just pushed me off. I told her I could just meet her at her room and she said she wouldn't suggest that because her "friend" was there. Yeah, probably another paying client. We went back and forth and I told her that she offered the 4 free fucks if I paid for a used tire for her car and changed it, which I did, but It seems like everyone can fuck her but me. She likes to go the route of "well, I need to make my money first, I'm not brushing you off but I gotta take care of me first making sure I have somewhere to stay." She keeps telling me I just need to be patient. I asked her how many of her other "friends" did she hit up when she was sitting on the side of the road and how many of them came. I really was only looking for a bj or maybe just one free fuck but she was the one who offered 4 because she was stranded on the side of the road. Long story short, I never linked up with her yesterday. This morning she texts me saying she is leaving my brother's apt after spending the night with him. Yeah, I'm sure he paid but at this point I'm not looking to get anything free from her at all. On one hand I'm tempted to go cut the tire on her car just to put her back where she was before and just cut my loses and move on. But on the other hand I'm trying to get at least 1 free fuck from her just to recoop the cost of the tire.

What would you do, hang in there or cut your loses? At some point she's going to hit me up crying how she needs help with something else and I'm not gonna be so quick to jump up and go save her even if she promises 20 free fucks.

 

I would have cut my losses before they became losses. If nothing else, she's your brother's "problem" to deal with and I guess that, now, you see that maybe you should have heeded his "she's off limits" thing. Water under the bridge; all that matters now is what you're going to do about her.

 

Cut the losses! Move on!!

 

Yeah, I'm all but ready to do that but at least I'm going to hang around for maybe one more free fuck. She keeps telling me to be patient however we can get into a text conversation that will last an hour or more. During that time you're just sitting in your room texting with me that could be the time she'd say, "hey, come over real quick." Yeah, she's my brother's problem and she even told me that it's sort of a fantasy of hers to be fucking two brothers. She even told me that she wants to ask my brother to do a three-some with me, him and her. He definitely won't go for that since he doesn't know I've fucked her. The only thing I'm out is $45 for one used tire and maybe some gas back and forth that day but the promise of help me out and I'll give you 4 visits for free excapes me. Again, this is a girl who will hang out with her neighbors in the front of their apartment and because it's dark one of them will bend her over and fuck her. The neighbor she's next door visiting and cooking in his kitchen will bend her over the counter and fuck her because she likes being used and slutted out. The co-worker who traps her in a room she's cleaning and has fucked her several times over the past few weeks. Not to mention that she's fucked three guys if not more in my brother's apt when he leaves her there to go to work. He was happy to come home to a girl sitting naked on his sofa who had been sitting there masturbating all day long no knowing that when he's fixing his plate on the counter some guy had her ass up on it several hours earlier. He sits on the sofa probably in some juices left behind by another guy and she just says it was her squirting while masturbating. Not to mention what she did on the bed. I'll cut my losses and move on but I'm going to see if I can get one more freebie out of her.

 

Is the pussy that good that you're willing to get in over your head with her and more than you've already experienced?

 

Let me put it this way. This girl is easy. Is the pussy that good? It's descent plus she loves anal. Is it worth constantly loosing money over, no. Would I play the game to see if she's gonna let me fuck her 4 times for free? Yeah, I can play along but I promise you there will be no more running to her rescue or doing any work on her car. If I could just get 1 free fuck I'd call it a wash on the tire but she was the one who said 4 free fucks.

 

It's more like you have to promise yourself not to keep running to her rescue... just to get the pussy for free. I know I wouldn't to get in deeper with her and especially when she's a working girl and kinda/sorta living with your brother (and working out of his place) and I know it's just me but I wouldn't continue to be involved with her and no matter if the pussy was free to me. Sex in exchange for favors is as old as mankind and women have kinda always been like, "If you do this for me, you can have sex with me..." AT the end of the day, I suppose that you gotta do what you gotta do.

 

The problem with my brother is that he only cares about himself. He has told me on several occasions that one particular girl he has seen, who doesn't allow her clients to nut in her, that he'll use a condom but cut a hole in the top so when he's having sex with her the condom will slide up his dick so her can fuck her raw and nut in her. Then he'll have another condom stashed somewhere within reach so that when he pulls out of her he can reach down and grab the condom with a little bit of lotion squeezed in the tip. He said he's done this girl like this several times. When I asked him if he cares that she might get pregnant he said that she is probably having sex with so many guys daily until by the time she finds out she's pregnant it'll be hard to track it back to him.

In regards to the girl in question, I'll still text with her because she is fairly cool on that level but rest assured, she will need another tire or a jumpstart, or the rear brakes changed, etc at some point. At 6:33 this morning when she text me to say she was leaving his place and heading back to her room she asked me what I was doing. I'm off today so I told her I was just laying in bed. That's the last I heard from her. I'm going to let her and my brother keep kicking it. What they do doesn't bother me. But I know she's gonna text me one day about how my brother has screwed her over yet again and she doesn't know why she keeps going back to him. Well, I'll tell you, because he's paying you. I don't know too many escorts who turn down money for sex.

 

He does what? That's illegal in some, if not all, places! A DNA test can easily track it back to him if he knocks her up! What the fuck is he thinking about? Not my problem but that's some fucked up shit. What she needs is a man who is (1) going to support her and (2) be 100% okay with what she does for a living instead of depending on you to bail her out and in exchange for some pussy.

 

Yes, my brother does this and has done it on several occasions. Sticking a condom with some lotion in it close by then when he nuts in the girl he said that she'll say something to the effect of "man you really got me wet." My brother doesn't care about nobody but himself. I've told him that was illegal not to mention what if he catches something a shot can't get rid of. Back to the girl in question here, remember she got pregnant and wasn't sure who the baby daddy was so that means she's letting guys nut in her too. My brother was so excited the baby might be his until he goes out and starts buying baby stuff, car seats, etc only to have the DNA test done after the birth and it wasn't his baby. He wants to be in a serious relationship with this girl but why would you want to be in a relationship with a woman who, when times get hard or she needs/wants some extra spending money, will post an ad to fuck a few guys. Or, when she gets horny and you're not around will call an old regular and tell them to swing by your place because she knows you're at work. Little does he know that this girl has fucked a few guys in his place. And the girl is not what you call cute or beautiful. On a scale of 1 to 10 I'd give her a 5 maybe a 6 but that's pushing it. And that's only because she's a descent fuck, I can overlook her looks.

Recently my brother had a girl over to his place who had gained a lot of weight since they started fucking. Yeah, she charged for sex too. She had agreed to let him fuck her raw and nut in her for like $80. He then had another girl lined up the next day who he called "baby momma" because she had 6 kids by 5 different men and was still selling pussy. This girl was allergic to latex she made my brother wear this thick condom, according to him. This girl was charging him $100 to nut in a condom but the first big girl was only charging him $80 to nut in her raw. What did he do? He paid the first girl to come over but then faked an orgasm with her to save his nut to bust in a condom the next day. Low and behold the 2nd girl never showed up the net day.

I can tell you stories all day about my brother. Here's another one. He's 55 and had signed up for Facebook dating and linked with a 19 year old girl who lived about 3 hours on the other side of our state. This girl told him she wanted to be turned out by an older guy. My first thought was, are there no older guys in the city you live in. Then she told my brother she was going to drive to our city to have sex with him. He ate that shit up. It was around Super Bowl time and he text me that Sunday to say that the girl was coming to town with her family to watch the Super Bowl with some friends in our city. Secondly, who drives 3 hours just to watch a football game with someone? Apparently when the S.B. gets here she told my brother she was on her way but surprisingly hours later she goes silent and never hits my brother up. She only texts him when they are about to leave. He truly believes she came here. I asked him how was he just gonna roll up to somebody's house as a 55 year old man, and pick up a 19 year old girl and how was she gonna get missing for an hour or so while they go back to him place and have sex. My brother said, "that's her problem, not mine."

I have more stories about my brother that I just can't go into details here. Back to my OP. The same girl hasn't hmu since this morning and I've not hit her up either. I'll tell you what will happen. She'll text me late tonight to say hey or she'll text me in the morning to say she spent the night with my brother again.

 

Your brother is a piece of work. I don't have any issue with you and your brother "sharing" this pussy but trading favors for pussy, I dunno, man, that can go bad pretty quickly and no pussy is truly free - you're always going to pay for it in some way that isn't cash or credit card. And really. why would you care or want to know that she spent the night with your brother? If that girl was really 19, then she was a legal adult and able to consent to sex with your brother although her family might have pitched a bitch about their differences in their age but if she's over 18, all her family can do it pitch a bitch... and maybe try to off your brother because some families can be like that.

Or, worse, she lied about her age and your brother gets caught up in a sting operation and one that involves Feds and, well, he's not going to fare well...

 

I totally agree with you on everything you said. No, I don't care to know when this one girl spends the night with my brother but she will casually text me the next morning to say she's leaving his place and heading back to her room. Trust me, I'm not asking "did you stay with my brother last night?" "IF" I get the chance to link up with this girl again I'll never know but there have been times when she was available and was willing to let me swing by her place, however, those visits would have to be a paid visit because "I need to pay for my room." My thing is this, I'm not making a promise to someone in exchange for them doing me a favor without doing my best to satisfy that bet ASAP because I don't like someone holding something over my head.

My brother has been married twice and both marriages ended with divorce due to infidelity on his part. His 2nd wive and he lived in an apartment complex and they worked together to get their credit cleaned up then went through a program to have a nice house built from ground up. They were in that house maybe 2 possibly 3 years before they were forced to sell it because of his infidelity. They just stopped paying the bills. My SIL was a nice person but when she found out my brother was cheating on her she had had enough. My brother would take girls into his home and have sex with them on their marital bed and he'd take naked pics of the girls and text them to me. I told him he needed to stop but he told me I don't tell him what to do with his money. His biggest complaint was that he wasn't getting the amount of sex now that he was when they were just dating. This woman had an autistic son from a previous relationship and that little bot latched onto my brother like crazy. I told my brother that by the time this girl gets off work after working a full time job, come home, fix dinner, and then get her son situated for the night she's probably tired and the last thing on her mind was laying there for my brother to jump up and down on 4, 5 or 6 times a week. When the house was sold each of them walked away with around $26k as a settlement. Since he didn't have a place to stay he ended up back at our parent's house and slept on their sofa with his own son from his first marriage. The other brothers and sisters told him he had 3 months to get his crap together and get back out our parent's home. That 3 months lasted 2 years only because mom has a soft heart and wouldn't put him out. Oh, and the $26k, he blew that. He's a member of a church and because the other church members were getting newer vehicles, he wanted one too although there was nothing wrong with the SUV he was driving. He takes almost $17k and blows it on a newer used SUV.

Again I say, I have stories on top of stories on top of stories about my brother.

 

Move on from your brother as well! Set new goals with strong boundaries.. just my thoughts!! ;-)

 

If you're getting with her and paying her, okay - it's what she does for a living and it's a... cleaner version of transactional sex as opposed to, "I need a new tire and if you get it for me, you can fuck me for free!" because one "favor" leads to another, then another and you're thinking that you're getting the better end of the deal by getting free pussy... but the price of those favors adds up, don't they? I get that you're not asking her about staying with your brother... but why is she telling you this?

Your brother sounds like a couple of guys I used to know; couldn't keep their dick in their pants, any money burned holes in their pockets, marriages ruined by various means.

 

Yeah, if that was my brother, I'd left him in the dust a long time ago and I wouldn't have fucked her and no matter how much I needed some pussy.

 

Your guess is as good as mine why she tells mwe when she's going to my brother's or when she's leaving. They have a volatile relationship as well. The last time she spent some time at his place, almost a month, my brother was texting me every morning saying how he was tired of having sex. She was wanting to get fucked every night. Sort of contradictory to my brother's mindset of always wanting sex but when he has it at the ready nightly he's tired of it. But now, she likes the thrill of fucking two brothers. One minute they're good then the next she's texting me complaining about something he's done.

I asked my brother once does he ever get tired of paying for pussy from so many different women and he said no. He used this analogy. If you had to go to the same restaurant every night and eat the same meal wouldn't you get tired of it? My reply to him was this. If you have someone at home, i.e. a girlfriend or wife, then you can go to the same restaurant but you don't have to get the same meal each time. Get the chicken one night, get the fish the next night, try the steak on another night. Then if you wanna try to chicken again, throw some hot sauce on it. Spice things up a little.

 

And yet another story.......

A week ago my brother texts me the pic of a girl who did an outcall to his place. She looked like she was no older than 22 or 23, if that old. He said that they agreed upon her coming to his place and having sex while he recorded. He said that when she got there and started taking her clothes off she told my brother, and I quote, "did my people not tell you I'm on my cycle so I can't actually fuck right now?" The first thing that came to my mind was "did my people tell you..." To me that means you weren't talking directly to her but possibly her pimp or handler. And secondly, she told him that if he wanted to reschedule and she could come back after her period was done she would. So she left without getting paid. One thing I know about girls who do this, they aren't coming to your place then leaving empty handed. They want money for their time and gas. When he told me that I told him it sounded like a set up. She wanted to get into his place to see what he had, furniture, electronics, so that "her people" could come back later and possibly rob his place. My brother will not or prefers not to do an incall at a girl's hotel room, home, or apt because he feels he might get set up and robbed. However, he has zero concern about giving out his address to a total stranger to come to his place or going to pick them up and bringing them back to his place.

I have my main girl I go see from time to time but I'm not seeing her ever week or even every other week. I have a life to live and bills to pay. I don't have time or money to be paying for sex 2, 3 or 4 times a week. I may see my girl once or maybe twice month. Sex is fine but when you're neglecting your household bills for it then you have a problem.

I've gotten to the point to where I told my brother to stop texting me about the girls he sees or plans to see. Several weeks went by and we didn't text each other until last week when he just had to hit me up about the one on her period. A day or so later he texts me to say that the girl hit him up saying her period was off and wanted to know if he wants to reschedule. My last text to him was "I don't care!"

 

It seems to me that having sex workers in your home can and will set you up to be robbed and even killed if he's home when they break in. To me, that's way too fucking risky and, really, if she was on her period, why was she "working?" How much would you bet that he rescheduled with her?

 

My guess was that she wasn't on her period and that she just used that as an excuse to (A) not have sex with him and (B) get into his place to scope it out. What escort do you know that will drive all the way to a guy's place then walk out without making a dime? You would have thought she would have offered oral sex just to get paid or something. Nope, she put her clothes back on and said "we can reschedule."

And yet another story.....

Remember the one girl he calls baby momma, the one with all the kids. Well, remember she was coming to his place one night and her car broke down and that ended up being a saga for him. That following monday, my brother is off work (yet another story) so he text me while I was at work asking what I would do. Apparently, this girl, since her car was down, asked him to take her about an hour away to another city so she could file court papers on one of her baby daddies. He asked me if I think he should do it. Given that's an hour away I asked him what was she willing to do for it. You know me, I like a deal. I asked him if he took her could he get a free fuck. I mean, you're asking me to do at least a 3 hours round trip road trip so you could go handle one of your baby daddies. He told me that he asked her and she said no. I told him then she would find another way to that city. My time and my gas, plus the miles on my truck driving you an hour away has gotta be worth something. He then gets hot with me saying how he didn't mind doing it. Come to find out he has been running her around quite a bit for free but still paying for pussy.

 

I know guys will do a lot of "stupid shit" for pussy... but this is taking the cake.