Took a trip, and am I tripping?


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:

And my lovely bubbling drink at the steak house:


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.

Pressure on dates…. ugghhh


Last night I went out with a new guy. He was someone I met off the swinger site. He had like 60 validations and from his pictures he was hot, hot, hot!! The only face pictures I saw were not straight on. Like he was looking down or had the camera slightly in front of him but from what I could see he was good looking. He was really muscular and had a set of six pack abs. His cock was….gigantic. Maybe on the level of “too big” that I mentioned in the previous post about Big Black Men. I wasn’t too concerned about that though and I never asked him his actual measurements.

In any case he lives 3 hours away so I was a bit surprised that he had emailed me. I responded once and then had forgotten about him until the Professor had gone to a swinger party in another town and I had ended up here alone after not finding any sufficient men off Craigslist. It was then that I emailed him back and we got to texting. He seemed pretty cool, other than an annoying habit of calling me “babe” and sounding a bit full of himself.

Still I figured if we were to meet he would probably be someone I’d sleep with. When I asked him about the distance between us he claimed it was no big deal and he travels frequently. He didn’t mind driving up here to meet me and said he was looking for a “swinging partner” to join him at parties. I kinda let him know that I had that already but he wasn’t deterred.

Anyway, I again forgot about him for a bit, until he texted early in the week to let me know he would be coming through my town on his way to a big city a few hours away. So we agreed to meet up. We flirted a little over text and he asked for more pics of me but I didn’t send him any.

I told the Professor I was going out on a date, which was kind of hard but he didn’t say a whole lot. I asked if he was cool with it and he said “It doesn’t matter. I am sick anyway and you are free to do what you want”. Not really encouraging and I felt bad that it was when he was sick but I went out anyway. I still don’t feel like we have completely worked things out from the other day. Nevertheless I still care for him and think I want to keep seeing him. I asked if he had slept with anyone without telling me and got a very adamant NO!!!!

So, onto my date. At first he had tried to squiggle out of taking me out beforehand and wanted to come straight to my place. I wasn’t having it. There is no way of telling if he would be a creepy stalker type or if I even want to have sex with someone without meeting them in public first. Being at my house is just too much pressure on me if I decide I DON’T want to and guys can really lay that pressure on thick. Plus he’d know where I live. One of the guys I slept with once last year STILL freaking harasses me and I am SO GLAD he doesn’t know where my house is. He tries to make me feel guilty for not wanting to see him again when actually the first night I did because I was under a lot of pressure and he basically ripped my clothes off and just started licking me. Then he was holding me down and not letting me get up to leave when I wanted to. I have had other experiences before where I ended up sleeping with someone I really wasn’t that excited about because I felt obligated and just in case I wanted a chance to assess things in a public setting.

I was an hour and a half later than I expected for meeting him. I felt bad but had to run my kids to their dads and come back which took about an hour and then was trying to clean up around the house before having anyone over. That’s another reason I don’t really like to have guys over at MY place. I have kids and there is always some cleaning up to do after they leave and it interferes with me trying to get ready to go out. Like, who wants to be cleaning the toilet and sweeping right before a date and right after showering? UGGH. It’s not putting me in a sexy mood, lol, and I start feeling resentful like can’t this guy just get a hotel or something and here he is wanting me to hurry and get there. Don’t worry, I kept him updated as to when I was coming and I had TOLD him beforehand that it was just an estimate as far as the time, but he did have to wait awhile.

What kills me is that later he claimed he was getting a hotel here in town because he wasn’t planning on driving straight through due to it being late. WTF? Then why the hell didn’t he get a hotel BEFORE the date and spare me all the extra cleaning (I had told him that is what I had to do). Why did he need to come to my house? SMFH Driving my kids to their Dad’s house is annoying to me too. It’s way out of my way and costs a lot of gas money. His vehicle isn’t working and I feel like in some ways he is deliberately sabotaging things for me. He’s passive aggressive like that. He keeps making our lives more and more difficult and I think it’s a continuation of the emotional abuse that went on in our marriage.

So I’m not in the best mood but I got myself together and all fixed up and headed to the sports bar where we were meeting. It was packed and he was sitting just inside the door. He doesn’t look nearly as attractive face to face as he did in the pictures. He’s still a decent looking guy but there is just something I don’t like and can’t put a finger on it. I smell something that smells vaguely like, well…. shit, lol, but I don’t know where it is coming from because there are a lot of people there around him. I notice his teeth are a bit messed up in the front. Apparently he was careful to hide that in the pictures.

He hugs me and says that maybe we should just leave or go someplace else since it is so crowded. I sense that he is trying to get out of buying me a drink, which is a turn off too. I suggest maybe we should just sit at the bar and he agrees. We order our drinks and the guy cards us, so I whip out my ID (it cracks me up to get carded when I’m only 4 years away from 40 but whatever, lol, it happens every time I go out). However, he doesn’t have his ID and has to go back out to the car. He takes a long time and I start to wonder if I’ve been ditched but chat a bit with the bartender (who is a cute, kinda hot blonde guy). He apologizes for carding us but says he has to. I start to wonder about the guy I am with and how old he actually is. He does look kinda younger than I expected and I can’t remember what he told me before.

So finally the guy comes back and has his ID. I ask him how old he is and he states 26. Yeah, that is a little on the young side for me. I’ve never really been a cougar and my one experience with a 22 year old made me feel awkward even though he was handsome and nice and okay in bed. It just felt weird and I couldn’t do it again even though he wanted me to. Generally, I Iike men my age or older, though a few years younger is okay. My fuck buddy just turned 29.

I think I smell that smell again and I am almost sure it is coming from him. Gross. I’m starting to think I definitely don’t want to do this. However, we talk for a bit and he is nice. He is in college and majoring in Psychology, which is what I got my degree in. He works in a group home which I have also done in the past. He’s nice but I’m still not feeling the connection. Something about the look in his eyes, I just don’t feel it…and the smell. He’s not bad looking or anything, but not what I expected and while he looks muscular it’s not nearly so much as he seemed in the pictures. He’s very tall though and says 6 foot 3.

When the bartender asks if I want another drink I say no, thinking I don’t want him to have to pay too much since I am not really feeling him. He says come on have another one and tells the bartender to get me another Mojito anyway.

After our drinks he pays and we head outside. He asks if I want to head back to my place and I say I’m really not sure that I do. He says oh, you are nervous huh and says he will walk me to my car and we can talk a bit. So we are standing by my van and he keeps saying I must be nervous. He tries to kiss me and I kind of pull away. He keeps talking about how nervous I am and I tell him I’m just not feeling much chemistry and not sure I want to do this.

He keeps telling me it is because I am nervous and says I will change my mind once we get back to my house. I say I don’t know that I want to go back to my house and he says I am just nervous and we should sit and talk in my van for a bit. I reluctantly agree and he gets inside. He tries to kiss me again and yeah there is a faint smell of crap. Yuck! Did he step in dog poo or is he unwashed or what? Ewwwww…. I pull away and say I am not ready for this. So he starts trying to put his hand between my legs. I push him away and say I really just don’t know if I want to do this.

He starts asking me if I have ever brought a guy back to my house the first time we met from the site and I say no, which is true but I have done so from other sites. Still I don’t want to encourage him. So he goes on about how I am just nervous and will change my mind once we are in a different setting. I say I really don’t think I will so he launches into an argument about how this is the “perfect time” and we have “a great opportunity” to do this. I tell him repeatedly that I don’t feel the chemistry with him and also he is younger than I expected (I later looked at his profile again and it says he is 110). He keeps saying he thinks I am hiding something that I will end up telling him later. So when that doesn’t work I use the Professor as an excuse and say I am in a bit of an open relationship but I don’t want to hurt him too much by sleeping with just anyone unless I am really feeling the chemistry.

Over and over he keeps trying to convince me (by arguing, totally unsexy) that this is our opportunity and that if I don’t do it now I will regret it later and be texting him and wanting to meet again to feel the chemistry. He says he is not good at conveying chemistry till we get to the bedroom. I tell him again that I don’t feel it now and don’t think that will change and don’t want to go back to my house. He asks what it is about him that I don’t like and was like “you liked my pictures, didn’t you??” I said it’s not anything about his looks and that we had a nice conversation earlier but I’m just not feeling him. He kept demanding I be more specific as to why I didn’t like him. I wasn’t gonna say “you smell like dogshit” but also I didn’t feel it with him at all so kept focusing on that. He didn’t like my vague reasoning, but what was I supposed to say?

He starts to get a little angry and I tell him I feel too pressured. So he asks if it’s because I am afraid he is going to have a one night stand with me and never talk to me again. I say no. (Oh, Hell no, more like I am afraid he would become clingy, needy, annoying as hell and turn into a stalker like a couple of guys I have slept with once in the past). This went round and round and round with him trying to argue and me trying to get rid of him for OVER AN HOUR AND A HALF. A couple times he tried to kiss me again and tried to rub my clit over my pants. I pulled away and told him I just didn’t want to do this and that he was pressuring me and he said he wasn’t going to force me to do this but that it was a “perfect opportunity”. Sigh…guilt trip after guilt trip.

One of my children called me on the phone (thank God) and I said I need to go pick them up. He acted angry that I wasted all this time being “unsure” when we could have been doing other things and said he would like to meet me again on Sunday when he comes back through and maybe then I would feel the chemistry. He asked where we were going to go from here and whether I would want to talk to him again. I said “I wouldn’t waste your time” and he said “oh but it’s not a waste of my time at ALL, you are gorgeous”. Repeat about 5 times. No, I am not feeling it, DON’T WASTE YOUR TIME. I am sorry this isn’t going to work.

He acted like I was breaking up with him or something and looked like he was about ready to cry. I felt bad but I just didn’t want to have sex with him. He blamed me that he was too tired to drive through to the other city but he had known beforehand it was going to be late when he left. I said he still had plenty of time and he said no he had been planning to get a hotel and stay here because it was too long of a drive. He knew darn well I wasn’t gonna have him stay at my place because I was due to get my kids. At least he should have known that. No way a strange man is sleeping at my place with my kids there.

FINALLY, he gets out of the van, slams the door like he is angry and looks like he wants to cry. I feel bad but I just had NO DESIRE to sleep with the man. This is why I HATE going on dates with new people. You just don’t know for sure if you are going to like them and guys cannot take it when you say no. UGH, UGH, UGH!!! I wanted him to leave so badly but he just wasn’t accepting it. I don’t know how I could have been any more clear other than to say “GET THE FUCK OUT” which is not something I am comfortable saying. I am way too polite for that and hate to hurt people.

I thought the Professor would be glad I didn’t sleep with the guy but when I told him the short version of the story (that this guy had spent an hour and a half trying to argue me into sleeping with him) he was like “well, what do you expect, you met him on a sex site!!” I asked if he felt that meant I was obligated to have sex with him and he said no but that is what guys are going to think. Surely they have to understand that it may not work out in person just because you liked them online though!! How hard is that to comprehend? I did not make him drive to my city, he was supposedly coming through anyhow. I don’t like this kind of pressure at ALL and truth be known I am pretty darn picky. It makes me DREAD meeting new people in the future and possibly having to go through all this again.

Just because someone’s pictures look good does not mean in person they will be what you thought. I have come across that more than once and was bound and determined NOT to have sex with anyone I didn’t feel completely comfortable with and turned on by, from a sex site or anywhere else! How the hell would I be turned on enough to have sex after an hour of him trying to ARGUE with me and debate and convince anyway? He was NOT doing anything to make me excited to sleep with him. I definitely need a little bit of that from a guy to be attracted. I do feel bad that his time was wasted but I don’t owe him sex. I’m actually proud of myself for standing by my guns and saying NO despite all the pressure. I can’t believe the Professor didn’t get that. MEN. Sheesh….