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Took a trip, and am I tripping?

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I haven’t even had a chance to tell you all about another man in my life! We will call him Chicago. He lives here in my city half the time, but travels back and forth to his home in Chicago every couple of weeks. He works from home doing some kind of computer engineering, but prefers living there, to here (where his child is) so he has condos in both places.

Actually, he recently flew ME to Chicago to stay with him for a weekend! He wined and dined me and took me to my first comedy show- to see Cedric the Entertainer. It was an exciting weekend for me, with getting to travel and experience new things. His condo has a beautiful view of Lake Michigan and he took me to a delicious steak house, where he dropped well over $200 for dinner.

Here’s the view of Lake Michigan from his condo:
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And my lovely bubbling drink at the steak house:

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I’d had some car troubles, thanks to my teenager (long story), so Chicago covered rental vehicles for me to take my kids to their dads, and also paid for my gas. His brother drove me to the airport. Obviously, this guy is doing alright financially. 😉

Actually, he’s been probably more of a Sugar Daddy than any of the others, buying and giving me things here and there. He gave me a brand new printer for my computer and bought me a shawl so I wouldn’t need to borrow his jacket when we go out. He’s taken me out for lots of dinners at nice restaurants and to the movies several times.

Sounds fabulous right? Well, not quite. I’m really, just not feeling this guy. I just can’t bring myself to LIKE him that much. I’m trying, really I am, but it’s just not there.

He’s obviously doting on me, and being a nice person. He claims to like me a lot. Yet, some things just really bug me. I’ve finally figured out that he reminds me of my ex husband.

He reminds me of him in SEVERAL ways. One, is how he acts in the bedroom. We just can’t seem to have good sex. There is like, NO chemistry. He’s doing some of the same things that other guys do, at least trying to be good, but it’s just not working for me! It’s so weird.

One of the things that bothers me, is that he just doesn’t seem to be able to, or maybe he’s just not interested in, reading my body language. If I don’t like something, and try to make it clear, he just keeps trying to do the same damn thing!

Like he has an obsession with trying to lick my nipples. Sometimes I like that, but not the way he does it. He will lunge toward my nipples with his tongue flicking out and I am like cringing. I’ll kind of push him away and he comes back again in full force. So I actually covered my nipples with my hands and he tried to pull them off! I wouldn’t let him so he’s laughing about it, what you don’t like that? I said they feel sensitive and now he harrasses me about it, major turnoff. He is constantly trying to do what I have made clear I wasn’t feeling.

What’s crazy is that my ex husband would try to do that very same thing and act the very same way about it- annoyed with ME for not enjoying something. Get over it already and quit trying to do something I’m obviously not liking! Sheesh!

That’s just one example. The rest of the sex just isn’t working well either. I just don’t like it.

I’m sure some of it, is that he’s just NOT the Cohort. I’m emotionally attached and it makes it hard for me to be with someone new. I only started seeing this guy after the last miscarriage, when I wasn’t sure what was going to happen with he and I.

Still, it’s not just the bedroom where he’s acting insensitive. He doesn’t seem to pay any attention to the things I SAY to him. It’s like he cuts me off or changes the subject or just says “uh-huh” like I’m not saying anything interesting. It’s very upsetting to me to not feel heard when I am talking. That too, is very much like my ex, who brushed off anything I wanted to talk about (outside of the Bible or politics) as unimportant.

He also has a tendency to over-explain things to me, like he thinks I am an idiot or something. It makes me feel like a child. He took me to a park the other day (and to eat afterwards) and insisted on looking up the history of the park on his phone and reading to me about how it was donated by some woman whose husband owned a biscuit factory, like he was giving me a lesson. TOTALLY like my ex husband, who was always lecturing about something.

He actually wanted to talk about scripture on our last date. Uggggghhh… he said because it was something “different” than what most people talk about and he thought it would be a nice change of pace. I spent 15 years talking about the Bible. I didn’t want to be rude but I really didn’t feel like elaborating on my thoughts about various passages of scripture. It felt torturous.

He wants to hold hands, and be “romantic” all the time but it makes my skin crawl. I feel guilty, but I can’t help it! It’s frustrating.

Anyway, when we got back to his place, I decided to play a little game, just to test and see if he actually does listen to anything I say. I asked him some questions about myself to see if he knew the answers to any of them, all things I had told him before. I was like what color are my eyes? He said “blue” (we were in candlelight and my eyes are green). I asked how many siblings do I have, where did I go to high school, what did I major in in college? He got them ALL wrong. Then I let him ask me stuff and I got every single answer RIGHT. Because I actually freaking LISTEN when someone is talking to me!

It bothers me so much, that I don’t know if I can stand it much longer, even with all the perks. His birthday is coming up soon and he has decided he wants me to make him a picnic with wine and grapes and strawberries that we feed each other on a blanket outside, and then I give him backrubs. It sounds kind of like Hell on earth. Not sure how to get out of it without being rude though.

I guess all this kind of explains why my trip to Chicago, while fun in some ways, just wasn’t what it was cracked up to be. The whole time I was really missing the Cohort and wishing he was the one with me. We would have had SO much fun, doing those exact same things together. Heck, I can have a blast with the Cohort at the grocery store! Lol

Chicago took me to the store with him the other day and I was miserable. He took like an hour to buy stuff and it was soooo boring. It reminded me of being a kid and getting dragged along on errands with old people. Bleah.

I was positively aching for the Cohort the whole time I was away in Chicago. He didn’t even know I was gone (it was two days, one night) but I missed him something awful. Then he called, right as I was boarding the plane. I told him where I was and actually ended up getting MAD at him for no reason. I think it was just all that pent up resentment that I was spending my time with someone else, when he was who I’d rather be sharing all this with. At that time we were trying not to have sex with each other.

We couldn’t talk after the plane took off, so I stewed on my thoughts for awhile and finally figured out that was what it was. So I told him the truth and said I missed you and the whole time I was here I wanted to be with you. Being with this guy was mostly meant to take my mind OFF of him, but it hasn’t been working very well.

I am so a city girl ;)

Ahhhh….life in the city. Despite all the setbacks with moving here, I am loving it! It immediately felt like home to me, and the little suburb we are in just really fits.

I’m so close to all these things I’ve never had a chance to do or try, stuff that it seems pretty much everyone else living in the real world has done. I was so sheltered for so long, and even though my teen years were wild, I was still pretty young when I met and started dating my ex husband. I was married and had completely STOPPED drinking before I ever turned 21, lol. Some of the men I have spoken with here have been shocked that I’ve never been to a casino, a karaoke bar, a comedy show, or any of a myriad of other basics that I missed out on during all those years I was living in a radically religious environment.

I’m like a kid in a candy store, only I’m held back a bit because I have actual kids. So my time is limited. My responsibilities haven’t changed, though I do have family nearby and more options for babysitting. Even though I love to play, my children are still a priority.

Well, money holds me back too, lol, but I’ve been beginning to discover that there are seemingly men all around in this lovely metropolis that have plenty of it to share. 😉 In fact, I went out with a man yesterday who paid $45 to have my laundry done for me so I wouldn’t “have to sit in the laundromat” (my dryer broke and I am waiting on a new one to arrive). He also took me out to lunch and tonight he wants to take me to a casino, possibly in one of the limo’s he says his business owns. I’m assuming I get to play with his money, and he is getting a room there as well. ::: squeal :::

This guy is kind of an interesting situation. I met him on Craigslist, where he was looking for a submissive, white, female, but he is on the swinger site as well and I had seen his profile before (though there are no pics). It says he is 49, but I am suspecting he may be a little older. He was different, in that he wasn’t looking to play with married women, but only single ones. His swinger profile says something about wanting a poly relationship.

Over lunch he made a comment about another woman he is seeing. He later told me he would like for me to meet her, but that there will be no pressure to play together, its entirely up to us. He’s actually been pretty cool so far about being fine with me doing whatever I want as well.

He’s decent enough looking, if older, and owns his own business, which clearly makes some bank. He was talking about how he likes to do things for people and wants to know what I’m dealing with because he may be able to “help out” in some way or another. According to him, he told one woman he is not a “sugar daddy” but then he is kind of belying that with his behavior. So I guess we will see. I’m not trying to take advantage of anyone but if he wants to pay for stuff I am totally cool with that!! 😉

He even mentioned the possibility of buying me a new phone! Mine is having major issues so that would definitely be nice! I’m not getting half my texts and some aren’t going out. It is driving me crazy! It really messes up communication with people and kind of fucks with my abandonment issues (as well as others). I’m trying to keep my cool and figuring the people who want to stay in my life will, regardless.

His voice sounds an awful lot like The Professor’s. Kinda funny. In a way I sort of like that. I wonder what he will be like in bed??

I’ve not had as much sex as you might expect, so far, living here, but I have been super busy with life in general. I did sleep with the Host once since I have been here and most recently I met another new man. He is an interesting situation as well!

This guy, I also met on Craigslist. I did a little browsing and responded to a few different ads the other day. 😉 Turns out he is a guy who had ALSO hit me up recently on the swinger site. Damn, us sex addicts are always on all the sites, lmao.

Anyhow, this one I had actually responded to, and he had emailed back but we just hadn’t taken it further yet and then we met on Craigslist. Kinda funny. He too, was specifically seeking out white girls. What’s REALLY funny is that it turns out he used to date a girl I went to high school with!

She is blonde, short and curvy and has a very pretty face. I think she may have been a cheerleader. I remember her from back in the day because she was running around with some of the same crowd and dating some of the same guys that I was. We weren’t personally good friends or anything but I don’t have anything against her.

Still competing with the same girls I was in high school, for the same guys though, lol, how fucked up is that?? I’m in a totally different city, HE is in a totally different city than either of us, wtf?? Hahaha What’s even funnier is that very recently I have seen a lot of pics of her on Facebook, because she is working with one of my GIRLS from back in the day, peddling a beauty product.

This girlfriend of mine and I used to get into hella trouble, so I know she is no angel, lolol. In fact I had halfway considered getting her to come to some swinger parties with me when I ran into her again on Facebook. She is a tall, slender but curvy, black girl that is now rocking her natural hair and has always been a fashion queen. She used to CRACK me up at parties with her side comments to me about things people were wearing. Things I would never even notice, like the fact that some guy had come with a rope holding up his pants instead of a belt, lmao. She’d be all under her breath “would you check out THE BELT” and have me on the verge of spitting out my drink. Hahahaha

We grew up on the poor side of town and none of us had money, but her mom was a crackhead and her dad was homeless. Her mom had these giant wine glasses in the house that were the size of your head and we used to steal them to go to keg parties where you had to pay for your beer by the cup. Somehow we managed to get away with it, lol, and ended up with a free beer buffet.

She also used to do all her makeup at the store. Like, we’d walk in and she’d be opening up packages and just put on her face right there plus a little perfume. Haha… Somehow she never got caught and always ended up looking good. We’ve all grown up, but I’m not sure she isn’t still a klepto, especially when it comes to clothes.

I love her to death but I’m not sure hanging out with her at this point in my life would be a good idea, lol. I also know how she is about guys and she likes the pretty ones…really good looking but super conceited and complete assholes. I haven’t seen a whole lot of her “type” at the swinger parties.

Anyhow, this guy said he was with the BOTH of them this past weekend, his ex and my friend. He said they were at a bar and my friend got stood up by some guy and was pissed. Yep…I told you, she likes the assholes, lol. She even dated the guy I refer to as “The Asshole” in some of my other posts, a former fuck buddy of mine, for a bit. Never!! I couldn’t stand him like that! 

Not sure what that means with this guy and his ex/”friend” but I don’t really care. I told him just not to tell them where he met me and he was like “uh, same to you” LMAO. It did make him seem like a safer option than some of the other guys I had talked with off Craigslist and I ended up hanging with him. I even accidentally stood up another guy I had planned to meet later, at a hotel. Ooops!! I got a little occupied and totally forgot!!

He took me out for dinner and drinks at a very nice restaurant in the heart of the city. We talked a lot and I got a little tipsy and we went to a hotel around the corner. He ran in to see how much it cost and said it was a lot but he told the guy at the front counter “fuck it, it’s worth it” and paid. 😉

This guy working there was a trip. He was a young black man, maybe in his 20’s, with dreads. After the guy I was with went in the restroom, he kept asking me about what we were up to that night. He was like “you two are gonna kick it aren’t you?” alluding to the fact that he knew we were about to have sex. Well, yeah, no luggage, Sunday night…last minute…um…

Then I ran into the restroom and when I came out the guy I came with was like “that guy is really interested in you, and he kept asking me if we were going to ‘kick it'”. LMFAO!

In any case, the sex was pretty good. He was maybe not quite as dominant in bed as I would have liked but I did get to cum. He kept stopping right before I would cum several times and was trying to hush me a bit, which I hate, but whatever. For the most part it was good and he was good with his tongue and fingers too, which I haven’t had much of lately so I was enjoying that. 😉 He wants to meet up again later this week.

I’ve been talking to some more guys but I don’t have time to explain that all at the moment. We will wait until something actually happens. 😉

Was I wrong?

Tonight I am questioning myself and the conclusions I jumped to regarding the Pilot.  Maybe I was wrong.  Maybe he really was telling the truth and I assumed the worst about him.  If so, then I was totally unfair. 

Yes, he did sign up for a party right after cancelling on me but his excuse, that I had blocked him or he wouldn’t have done it, may have been a valid one.  He may have reacted to my actions with anger and signed up to spite me.  Not very nice but then neither was deleting our profile we had just created.  That cost him money too. :/

We haven’t spoken but I’m debating apologizing to him.  Even if I was RIGHT then I probably shouldn’t have called him an asshole.  To be fair he didn’t react in kind. 

I’m not saying I’m okay with being cancelled on at the last minute, but it was a first time offense.  He’s never done anything else to piss me off before and actually seemed to like me quite a bit.  That may have changed now and I’m not expecting anything to go back the way it was but I’m thinking the right thing may be to apologize anyhow.

A couple things got me thinking in that direction and one was my date with the Producer last night.  He took me out to a bar that is run by some swingers here in town and we were chatting when the topic came up about what had happened with the Pilot.  Even though he was jealous of him before he was like you STILL haven’t forgiven him for that?  He said I was “harsh” and he wouldn’t want to be on my bad side, that he was going to try and avoid pissing me off, haha.

Then tonight, the Married Man texted me wanting to hook up.  His wife is out of town and if you all recall, the last time this happened he stood me up and I got pretty pissed at him.  Nevertheless, he’s too amazing in bed to stay mad at for long and I finally agreed to try and work with him on some last minute plans.  Okay, if I can forgive him repeatedly (because he’s pulled this crap several times), how can I be so angry with the Pilot for doing the same thing?

Well, guess what happened with Mr. Married Man?  He cancelled on me AGAIN!  Only this time I actually believe it was for a legit reason.  He got injured playing ball and cut his mouth open and said his tooth almost went through his lip.  He was texting me pics of it and asking what he could do to stop the bleeding.  It was actually kind of cute because he seemed to think I was going to know what to do and kept asking me questions.  What does he think I am, a nurse?  LMAO.  Fortunately I did know how to help because I have some very active boys and have spent far too much time in the ER. 

After things settled down a bit and he told me he was in so much pain he wanted to cry, he says he wouldn’t be able to go down on me if I came up and sent me a sad face.  He said he wanted to be able to satisfy my whole body and not just with his dick if I was going to travel all that way (he lives near the Pilot).  He was like “I am soo sorry”, and this time I feel like it was sincere.  I mean, sometimes people really do just feel “not up to” having sex and want to give you their best.  It’s possible that could really have been the case with the Pilot.

I know some of you all on my blog were questioning too.  I don’t know.  Maybe I should just suck it up and say I am sorry.  Of course from there he could still be really pissed or unforgiving but I guess the outcome isn’t really what matters.  My biggest concern with that is that he really WAS being an ass and then I am making a fool of myself or letting him take advantage of me, but if it ever happened again then I guess I would know.  Seriously considering it.  I feel bad for blowing up at him.

While I was mad at the Pilot, I spent a little time talking to the Professor.  He says he misses me.  He made some comment about me not believing him about things that made me wonder if I’m extra suspicious.  I know I’m not the most trusting person on earth.  I’ve been lied to way too many times. 

Anyhow, he sounds sad, and says he really hasn’t played much since he was with me.  He said only with some people he knew before and once at a party he went to but acted like none of it was that great.  According to him he’s only been with that married woman once this entire year, the time we got in an argument.  I told him a little about the Pilot and what happened because he knew about our couples profile and that I’d been to a party with someone.  He seemed a bit jealous that I have been going out and getting laid more than he says he has.

Then he was sending me pics of what he ate for dinner, lobster and some kind of avocado and tomato salad and telling me he was thinking of me when he made it. I do love my avocadoes and raw tomatoes, lol.  We haven’t talked a whole lot since.  He keeps saying he misses me but he’s not making any moves to get me back in bed. 

I talked with my fuck buddy recently for a bit and we even discussed the possibility of going to a party together.   Not sure if we will do that but looking forward to sex with him again, it’s been awhile. He has started bringing up anal though and I can’t say I’m all that excited about that.  It’s like seriously, the guy with the huge 9 inch, thick cock just HAS to be the one that wants to fuck me in the ass, lol.  I was like your dick is way too big for that kind of activity!   Of course he claims his ex- wife hated it at first but then got used to it and would ride him reverse cowgirl anal and he loved it.  Sigh….

Actually, lately, the person I’ve been seeing the most of is the Producer.  He’s been coming through here about twice a week.  I haven’t really been pushing the gold digging thing but he seems quite happy to offer things on his own.  He says he wants to take me to Vegas with him in the fall and then maybe on a cruise in the Bahamas.  Hey, I can handle that! 😉 

Each time we meet up he makes sure to take me out and do SOMETHING with me so that is fun. He says he doesn’t want it to be “just sex”.  He’s also talking about doing something special for my birthday next month, so we will see.

Once he brought up wanting a threesome with this woman he says he has slept with here before.  She is like 21 and blonde and he sent me pics and I’m wondering why the hell he always wants to see ME instead of her then when he is here, but whatever.  He keeps saying what incredible pussy I have.  I can’t help that. 😉  He’s like, “it’s just sooo SOFT and wet and hot and GOOD”.  He says he can’t believe I’ve had kids. Yeah…  well, what can I say?  LMAO  (Other than one of my kids was 9 ½ lbs with a big head and I had them all natural, guess it hasn’t damaged THAT area too badly anyway).

He’s still bent on becoming the “best sex ever” for me and wants me to rate his performance afterwards and tell him what a big dick he has all the time, but whatever, I guess I can oblige that, haha.  Shaking my head…. The sex isn’t bad.  It’s not off the charts spectacular but it’s still fun!! 

When we were at the bar last night we met a single woman that we struck up a conversation with and she and I exchanged numbers.  This is more likely a hangout thing than a sex thing, though she was having an issue with being in a fight with a current lover while her fuck buddy on the side cancelled for the night.  She seems like she might be fun though, so you never know. We were texting a bit back and forth last night but I was decidedly tipsy.  I also sent a drunk I miss you text to the Professor. He said he misses me too and sent a sad face.  :/  Dangit I’m just all kinds of confused right now.

 

Pedicure for a Pounding?

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Some of the men who read my blog are going to hate this post, lol.  Today I decided to try my hand at a little gold-digging with the Producer.  Normally, that’s not my style but he almost seems to be ASKING for it.   Maybe it’s a fantasy of his to pamper a lady.  Some men do seem to get off on that kind of thing.

In any case he’s very into me, or at least into the sex.  He texts constantly.  He keeps telling me what amazing pussy I have.  Obviously, he enjoys my blow jobs.  Today he made comments about how no one has ever done it like I do.  Haha.  I do have a little trick that I’ve been pulling lately that really gets the Fuck Buddy going too. 😉  Actually the Pilot was enjoying it as well. I’m going to have to keep that one up.

Last night the Producer told me that he went to a swinger club/restaurant in the city where he lives.  He said it was a great place and that he ended up hooking up with some woman that was half Latina and a lawyer.  He said she was hot and there with her husband and that they told him sometime he should bring a female with him.

Then he went on to tell me how he was thinking of me, and my warm, wet pussy.  All supposedly right after he fucked someone.  Yet this guy is telling me that he only wants to be FWB, no emotions involved.  Okay, because I’m not going to get any for this guy, guaranteed.  So, I hope he means that.

I mean, in some ways we are setting things up well for keeping the emotions away on his part too. He has yet to ever kiss me and I don’t want to.  Today a woman texted him while we were at the hotel and he was complaining how she’d caught feelings and was now annoying him with her questions and demands.  I’m just not enough into this guy to go there and doubt I ever would be.

So why continue to have sex with him?  Well, one, it’s convenient.  He says he really likes quickies and he is in my town at least once a week.  Two, it’s not BAD sex or anything, just mediocre and he is good at going down on me. He was able to make me cum a couple of times last time and this time he at least did by eating me out. Three, well, he really likes to brag about his material assets and I kind of like the idea of being spoiled.

He loves to flash his money around and drop names, so it almost seems like he’s wanting me to be as attracted to THAT as to him.  Like today he was telling me about the movie theatre and video arcade he has inside his house.  I mean, if he’s got all this money and I have virtually nothing, why not milk it a little bit?

I’ve fantasized before about having a Sugar Daddy.  Wouldn’t it be nice to have a guy who would buy you all sorts of expensive stuff and pamper you with his money?  What woman doesn’t want to be treated like a princess once in a while?  I could go for that, lol.  He’s not much older than me and is only 39, but whatever.

So after reading some of the comments on my last post (thanks Rouged Mount)I thought I’d give it a whirl and see how he reacts.  He was getting a pedicure here in town today and I dropped a little hint about wanting one myself.  He jumped right on it (yay!!) and seemed happy to provide that for me, even making a comment about how it could be in exchange for “hitting it from the back”.

I ignored that comment, lol.  What would that make me?  A pedicure whore?  What is a pedicure, like $30?  Not sure I’d want to go there because that’s awfully cheap, lmao.  Still this could be a start to more luxuries in the future.  I just need to learn how properly dig for gold, haha.  Maybe there is a crash course somewhere online.  I’ll have to look that up. 😉  I’ve never been very good at asking people for things, I’m way too giving.  Heck I don’t know if I’ve ever even asked a man to buy me a drink. However, I will admit to being a great salesperson, so I can CONVINCE people of things if I need to and that might help. 😉

As for my pedicure, it was actually pretty nice.  They asked him, in front of me, if he wanted to get his lady the “extras” so of course he had to agree.  I got a hot stone massage and a wax and little designs on my big toes.

See?
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He knows the people by name and goes there every couple of weeks so he was chatting and flirting and having fun and I mostly just relaxed and enjoyed myself and not having to pay for it.  I would totally love if he did more stuff like that, especially things that would make me look good for other men as well.  Like, buy me some lingerie or something, lol.

Afterwards we headed back to the same hotel as last time.  He paid for a room and we talked for a few minutes before stripping down and him going down on me.  Actually I kept on my shirt and he pushed it up for a bit and was sucking on my nipples and fingering me.  It felt good.

Then I blew him for a bit but he had to ask me to stop so he wouldn’t cum. 😉  I made him agree to wear a condom this time, so he had brought a Magnum and had it sitting on the nightstand.  He never put it on though. He went in from behind and I could feel that he didn’t have it on, :::eyeroll:::.  At least its almost time for my period so the chance of pregnancy is virtually nil.

Lots of pounding hard from the back and then he wanted me to ride him, which he loved.  He didn’t like me making too much noise though, he would stick his thumb in my mouth.  Not sure why he would care in a hotel, but whatever.  Eventually I sucked him to completion again and he was really trying to cum in my mouth.  I let it get all over my lips and chin, but not inside.  I really prefer to only drink cum when I’m feeling someone.

As a side note, I am still happy with the Pilot.  No clue what he did last night but he stopped texting around 8 pm and finally texted me again a bit ago.  We’ve got this couple that wants to meet with us next time and tonight he says he is at a gay club watching a drag show.  He made sure to add that he was with a female friend and no he is not bi, haha.  I like that he is open enough to do stuff like that though, without feeling a threat to his masculinity.

Anyhow, the Producer walked me back to my vehicle and I drove home.  Now he’s texting again saying he’s staying at the hotel and wishes I could come back.  I’m pretty sure I won’t.  I’m thinking I need to make sure he does something or buys something for me each time before I agree to it.

I’m actually kind of turned on by the idea that I can get a man to do stuff for me simply with the power of a little pussy. I can see how some women get addicted to that power because it can be a bit intoxicating. I wonder how far I can take this? It’s sort of a challenge. 😉