Tag Archive | rich men

An anal adventure…..

borisk

So many interesting stories to tell, but time to write in my blog has been eluding me. Life has kept me extremely busy lately. Some of it has been working my new job, which I really am enjoying, but I have also been having some play time! Just wait till you hear about my most recent sexscapade!! 🙂

FINALLY, after months of failure to sign in, Tinder started working again on my phone! Yay!! Of course, one of the first people to pop up on my screen was the Cohort. 😦 Reading his profile was excruciatingly painful but I managed to make myself swipe no and move on. We haven’t spoken in over six weeks or seen each other in months and I’m still struggling to get past it and him. Not that its kept me from dating or having sex, but my heart hasn’t been in it.

So of course, right away I went and responded to the poor guy that I left hanging after a wonderful date because the app stopped working! He was happy to hear I hadn’t gotten married and disappeared while he was off on business trips and quickly invited me out again. I still liked him, even though he talked A LOT and only hugged me at the end of the first three dates.

I actually complained to Mr. Firm that I was getting impatient, like, why isn’t this guy trying to fuck me yet?? Lol I was like he’s hot, he’s wealthy, he’s a former college football player, I know he can’t be that shy about making a move! He even made comments about how Tinder was a hook up site, yet, he didn’t seem to be trying to hook up!

I was getting a little frustrated, though it wasn’t like I wasn’t having sex. I’ve been with the Boring guy and Radioman a fair amount of times lately. Radioman has been pretty good in bed too… Sometimes he surprises me with a little kinkiness and he’s done stuff like spank me over his knee (blushing). I saw Chicago once more, and it still just didn’t do it for me. More recently, I got to see Mr. Firm, which was super hot as usual!! I hadn’t seen him in ages and he definitely still wows me in the bedroom! Then there was this new guy that is barely worth a mention, except for he took me to some really expensive restaurants. We did finally have sex but it kind of sucked and I hated the way he kissed. Oh, and the Pilot, he met me one day at work and we snuck away for a quickie (terrible I know) in an empty parking lot. It was fun but that was after I finally slept with this new guy.

I will call him The CEO. He is a big deal boss at his job and flies all over the place. A comment he made after we had sex, makes me pretty sure he is a millionaire. Not really surprising given where he lives and the company that he works for. I did a quick bit of research after that and some of his co-workers are making 7-8 million a year. He’s actually pretty down to earth though and not really flashy about it.

He’s almost too good to be true, good looking with pretty hazel eyes, built like a brick house, quite the gentleman, remembers to text, plans ahead and calls me beautiful…which makes me wonder if he’s hiding a wife somewhere. I guess you can never be sure, but he claims he’s not. We did have our first encounter at a hotel because he said his sister was babysitting his child at his place.

Suspect? Lol Maybe, though who knows, he could be for real. He says women always think that he is married or sleeping around because he travels a lot, but that he is not and doesn’t have all the time to be sleeping around that they think because he is working so much.

That is what he says, though after sex with him, I’m going to say I understand why they think that!! That, and who are all these women that are saying this stuff if he’s not getting around?? LMAO Not that I really care… 😉 He’s away on business trips all the time, out of sight, out of mind. 🙂

So, our first night together, he invited me back to a hotel room he had rented for the sole purpose of our “date”. It was a very nice hotel, almost more like a condo. It had a living room with couches and a fireplace, a full kitchen, plus a separate bedroom. He poured us glasses of a delicious wine and we talked and hung out for a good long time before he made any moves whatsoever. I was still wondering if it might not happen.

Finally, he asked if I wanted a massage. Wow, a man who actually gives massages! So many promise or allude to it and never do! He was very good with his hands too, massaging my shoulders and back. Then he wanted me to straddle his lap for a kiss. I was starting to worry that he was going to want to be dominated, lol. He had made this comment on a previous date, asking about when I was going to make a move on him and that had kind of put me off. Like ugh, ME make a move on HIM? No thanks…

Anyhow, I obliged and did as he asked. His kisses were nice and he soon suggested a move to the bedroom.

In there, he turned into a BEAST. I kid you not, I was completely floored by the change in demeanor once the clothes came off! They came off quickly too, lol. He was complaining that I had too many on at first (it was a little chilly and I was wearing leggings under a skirt). He practically ripped my leggings and panties off before grabbing my legs and yanking me across the bed so he could attack my pussy with his tongue. He was gooood at that too!!

He licked and fingered me into ecstasy before telling me to take off the rest of my clothes and stripping off his own. I was all to happy to do as he asked and the minute he got on top of me the worries of him wanting a dominatrix were gone, lol. He was definitely the one in control and he was very good at what he was doing too!!

He had me in all kinds of positions and every one of them felt amazing! He was very dominant but very sweet and affectionate too, jusssst the way I like it! I couldn’t get enough of him! We kept going for hours and I gave him some really long blowjobs in there too, but he never did cum. Ah well, maybe next time… I could tell he was really enjoying himself and he was rock hard, but it didn’t happen.

The most surprising part though, was when he had me lying on my stomach on the bed, near the end. He had gone close to my asshole a few times, like he was thinking about anal and I’d kind of tensed up and let him know nonverbally that I didn’t really want to. He laughed it off and just went back to regular fucking.

This time though, after hours of great sex, I guess my reserve was worn down a little bit. It was so good I probably would have done anything he wanted at that point anyway. He got near there and I again flinched. He was holding my wrists and had me pinned on my stomach on the edge of the bed. This time he didn’t move away but started putting a lot of pressure on my ass with his dick, not actually going in. I tensed up, but didn’t say anything and he started kissing my neck and whispering in my ear until I relaxed. The very moment my body let go of control, he pushed his dick up my ass. I let out a gasp but I didn’t try to stop him.

There was no lube used or anything like that, but surprisingly it didn’t hurt. Granted everything was super wet down there already. He kept still like that for awhile and me pinned under him where I couldn’t wriggle away, letting me get used to the feel before he started to move. He was gentle at first, kissing my neck and he asked if I was okay a couple of times due to the whimpering but he didn’t stop and was fucking me progressively harder as time went on.

Like I said, he never came but he eventually let me up and was very affectionate afterwards. It was like 5 o’clock in the morning before I finally got up to go home and we never slept.

Its hard to describe how it made me feel. In a way it almost felt like he took my virginity. Only, I’ve had some anal experiences before but they didn’t last more than a few seconds and each of those was painful. This was different. I wouldn’t say I’d go out of my way to do it again, but I’m not entirely opposed to it either. I was a little sore the next day. My arms had bruises on them from where he was gripping me too.

The sex, and I’m not sure how much the anal affected it, overall, made me feel completely different about him than I did prior to sleeping together. During, and right after, I felt super submissive towards him. I was flooded with all those “in love” type chemicals and it even made me feel for awhile like I was over the Cohort. For days afterwards I was in a bit of a haze. I think I am finally past that part, but he is on a business trip and we have plans to meet up again soon. I’m going to have to be careful with this one!

Loving the “benefits” that come with this one

pocketing money

Let me tell you, there are some real perks to seeing a guy with money.  I’ve been spending more time with the Producer lately and I’m rather enjoying all the little “extras”.  It’s SO nice to be able to go out and do basically whatever we want, without having to worry about how much it costs! 

He’s been coming here twice, sometimes three times, a week and getting a hotel.  He has a house in his home city but travels south of here for work and stops through on his way.  However, his roommate situation down there is about to change and he’s decided to get an apartment here, closer to me, for when he is in town.

I admit I was a little concerned when he first mentioned wanting to move closer to me, rather than down where he is staying now. I guess it made me feel a little claustrophobic and worried that he wants more than a FWB thing.  He reminded me that he spends quite a bit on hotels here each week anyhow so it really would be more cost efficient for him.  That’s probably true, even if he gets one of these luxury apartments very close by.  For now, he’s on a waiting list for those and going to stay at another nice apartment across town. 

He had thought about getting a roommate here and a bigger place but every time he arranged to meet someone and they discovered he was black they bailed out.  He was getting pretty discouraged and finally decided it would be better to get his own place. If only they knew.  People are so stupid.

 He’s probably way better at paying his share of the bill and a better roommate than half the redneck white guys in this area.  This is admittedly a rather backwoods and racist area to live in though.  One of the women he works with, who lives on the expensive side of town, said that every time she’s had a black neighbor they’ve left within six months due to the way people act.  Despicable, but I am not all that surprised.

Anyhow, he’s moving closer and likely I’ll be seeing him even more.  That’s not such a bad thing and he’s still gone a lot to his other home and on constant trips across the nation and overseas.  So it’s not like he should be breathing down my back or anything, lol.  I do like spending time with him, just want my freedom to play with others as well, without any drama. 

So far that is actually going pretty well.  I haven’t had much chance to play with anyone else lately but I have been in contact with my Fuck Buddy and I’m pretty sure we will be meeting up again soon.  The Producer may not LIKE me fucking around with other guys but verbally he’s saying it’s okay because he is messing around with people too.

 He actually wants me to meet up for dinner with him and a woman he is considering sleeping with soon.  It’s her and her husband, who just wants to watch, and he says he wants me along because he thinks it’s a little bit of an odd situation.  However, after talking a bit with him over dinner last night, I think I’ve discovered the REAL reason, lol. 

According to him she is really into women too and he wants her to meet me. Surprise, surprise.  Men… sheesh. :p Anyhow, as long as I don’t have to sleep with her husband, maybe, I guess we will see.

I’ve been getting treated to a lot of dinners lately, and drinks, and he even took me to a concert the other night.  It was one of my favorite rap groups from back in the mid 90’s, lol.  Wouldn’t you know it, in this town, there was such a small showing of people it was ridiculous!!  There were like under 100 people in the venue.  It was crazy.  We are talking a group that was pretty damn popular back in the day and draws in huge crowds in large cities…at least ones where people have actually heard some rap music before, besides like, Snoop Dog (or is it Snoop Lion?  Is he even “rap” anymore?  More like pop, but whatever…)

We still had fun. 🙂 Because they apparently weren’t even expecting a big crowd, it was held in a place that wouldn’t fit a lot of people anyway, and we were right up close to the stage.  Oh, and while we were waiting through the mostly lame opening acts, we went and fucked in his car in the parking lot, haha…and afterwards in it again, in my driveway, when he dropped me home.  Bad, bad, bad…hopefully my neighbors were fast asleep… 😉

So here I got to see one of my dream groups from back in high school, all because I mentioned it offhand to the Producer that they were going to be in town.  He was like “then I’ll buy us tickets”.  It’s so easy for him!  I love that!! 😀 How am I ever going to go back to seeing guys who don’t take me anywhere fun and pay for it??  LOL

Oh and he bought go-cart passes for my kids and I because I had mentioned the other day we were there and I could only afford to let each of them ride one ride.  We’d been staying in a friend’s condo for a little vacation and it was fun but we were financially limited as to what we could do.  So he bought TWO passes for my family, which amounts to $240.   

He’s also taking us to get a couple’s massage on my birthday and I am excited about that!! Plus we went and saw “We’re the Millers” at the movie theater the other day too. (I thought it was funny, even if some of it was cheesy and over the top, haha)  I’m getting spoiled. 😉  He keeps talking about taking me to Vegas with him.  Ahhhh…the life ;).

Last night we went out to a bar with a woman we had met there previously.  She is another single mom and had shown up by herself. After we all got to talking, she took my number.  She called wanting to hang out and since he was going to be in town, we all went together. 

He bought us lots of shots and we had gone up to the jukebox to pick some music.  It cracked me up because she unknowingly picked a song that he produced, by the popular artist he has won Grammy’s for.  I went back and whispered that she had been the one who picked the song, not me, and he laughed.  He had told her he was a janitor.  I could tell she didn’t believe that one but it was amusing in any case. Later on he started name dropping when some guy who had his own band was talking to him and her eyes nearly popped out of her head.  I’m sure he probably gets a lot of women with stuff like that, lol.  Smh…

Right now what we have going on is pretty low drama.  I’m trying to keep it that way.  Obviously I’m a bit motivated by all the side “benefits” too, don’t wanna lose those, haha. 😉 I’m a little worried about the apartment thing, and hoping it doesn’t keep us from going out and doing stuff though.  He has dropped a couple of comments about how then I could cook him dinner.  Bleah.  Not that I don’t love to cook, I do, but I do it every day for myself and my kids so it would take the fun out of getting to go out, which is more relaxing.  It’s nice for me to be able to get out and get a break. 

Also, I’m a little concerned about what I am going to be able to do for HIM when his birthday rolls around.  There is no way I could manage to do anything comparable, price wise.  I may have to cook him dinner then, or something, but that still doesn’t seem like much.  It’s right before Christmas too, when I’m at my financial worst, trying to provide gifts for my children, one of whom also has a birthday at that time.  Guess I will have to worry about that when the time comes!!  In the meantime I’m making the most of what I can right now because who knows how long this will last?  Hopefully a while, but you just never know!! 

 

 

 

Pedicure for a Pounding?

SpringPedicure1

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?
toes
toes2

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. 😉