Tag Archive | pushing boundaries

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!

I’m anal about anal, but(t)….

Anal_Warning

Okay, so I have never been into anal sex.  My first experiences with it were not pleasant and I generally tell my lovers I am not interested.  Still, I’ve never completely discounted that I might do it for *some* guy, at *some* point, if I liked him enough and he was careful.

Most of the men I have been with haven’t pushed it.  They might make suggestive comments once in a while, or ask, but when they see my lack of interest they let it drop, or never actually follow through.  I’ve been especially happy with the men in my life who have done it but aren’t all that into it and don’t even try. 

What can I say?  I know in this day and age it is practically prude not to want anal but it’s just not something that gets me excited.  I don’t even like a finger up there.  Ouch.

Actually, there was a guy once, a long, long time ago, who used to like to stick his finger up there while I was riding him.  It wasn’t so bad and at times I even enjoyed it. I don’t remember it hurting.  Yet when someone tries now, it does.  Go figure.  Maybe the guys I am with now just have bigger fingers?  Hmmm…

As for actual anal, the first time I had it I was 13.  Yes, you read that right.  It was with the first guy I ever had sex with.  We were having sex in a public sauna, near the swimming pool in a hotel, and he suddenly decided to stick his dick in there.  He tried to talk me into it, a little, AS he was doing it, but mostly just shoved it in.  All the way in…. and started pounding.

I got dizzy and lightheaded.  Not to mention it HURT.  I begged him to stop.  Afterwards I nearly threw up.  It wasn’t fun.  My body was nowhere near ready to handle anything like that.  We were young and I have no idea how big his dick was but I would guess somewhere between 7-8 inches.  He wasn’t small.

My second experience, I was 16.  I was seeing that crazy drug dealer guy I have mentioned a few times before, and he would have been like 21-22 at the time.  This guy was ROUGH in bed.  Really, too rough for my liking, to begin with.  The anal, he totally took me by surprise.

I was bent over the bed and we were going at it, when he pulled out and just RAMMED it up my ass.  HARD.  And kept going. My body practically went into shock.  I had a very similar reaction, in that I got so dizzy and lightheaded I nearly fainted, and then felt like I was going to vomit.  I don’t mean just KIND of “felt like,” either time.  I was doubled over and not feeling well for quite a while.

Since then there has been nothing attractive to me about the idea of anal.  Nothing.  Add fear of having my asshole stretched out, or getting hemorrhoids and possible disgusting messes, and yuck…   

On top of that, I have heard some real horror stories regarding anal experiences.  One was actually from a guy who is really into it and was sharing an experience that his roommate had.  According to him, this girl had some issue of backed up constipation.  In a drunken state, she and this guy had anal sex, that ended up in crap, ALL.OVER. THEIR. APARTMENT.   He told me the story in way too much gory detail and I don’t even want to share or you’ll all be retching over your keyboards.  Nasty. 

Being someone who is kind of obsessed with personal hygiene, this stuff REALLY did not appeal to me.  Then there were the stories of enemas.  I guess some women take the time to take THOSE before engaging in anal, you know, to keep it more “clean”.

 Um, the ONLY time I have ever used an enema was before labor was induced with my very first child.  No thanks to my mother in law, who offered this advice, I thought that would help make labor and delivery easier.  Please.  I have had four babies since then and that experience was by far my most difficult.  Never again will I take an enema.  It didn’t help with jack during labor and instead left me doubled over in massive pain, lying on the bathroom floor (but still not in labor) when I needed to get to the hospital for an induction. 

So we’ve pretty much established that I have a “no thanks, I’ll pass” general reaction to anal advances.  If you read my story of my first swinger party, you’ll know a man tried to stick it up there during my first six-some and I wasn’t too thrilled with that either. Still, I know it makes SOME guys happy and that a lot of people are really into it.  I’ve heard stories of women who loved it or even had orgasms from it and sure, I’m still a little curious. 

I’ve been curious if, as an adult and with someone more skilled and careful, my experiences might be different.  I’m still put off by some things (like shitty stories) but there was nothing nasty in either of my previous anal adventures, so I know it isn’t something that HAS to happen.

Keep in mind I’m pretty prim and proper most of the time when it comes to even DISCUSSING anything to do with bathroom habits.  I prefer to pretend it’s not something I ever do, being a “lady” and all.  Heck, I won’t even use terms like “shit” in real life and it’s even hard to type, lol.  People “use the restroom”, they don’t “take a dump” or “crap” or do disgusting things like that.

With all that out of the way, let me tell you what happened today.  I had a date with the Referee, who has been driving this way about once a week for a lunch date.  He again got a room at the Marriot and took me out to lunch at Applebee’s.    It was kind of freaky because the waitress, who waited on us the last time we were there, three weeks ago, said she remembered me ordering exactly the same thing.  Nevermind that I hadn’t remembered my exact order, or even the fact that she had waited on us before, lol.  Wow.  It wasn’t anything unusual or altered from the main menu either.  Crazy.

On the drive over he was playing porn on the dashboard, he said to “get me in the mood”.  Haha…as if I needed that. 😉  He kept telling me how much he likes me, how I have him “addicted” so much that he is driving a couple hours just to see me and getting obsessed.  Yeah, yeah, I’ve heard that before.

He said you aren’t supposed to get this way in the Lifestyle and he knows that but that he has it bad.  He keeps telling me he wants me to be his “wife” and then saying “I’m not trying to scare you though”.  I *think* he is kidding?  :p  When I told him about the party I went to recently he says of course no guy is ever going to want to share me if we are together.  He says I have that “effect” on men and that is going to make it hard for me to swing.

Oh, and he was claiming later, after sex, that he likes me so much that he has pretty much stopped having sex with whoever else he was sleeping with.  But then he let some comment drop about how this woman he normally sleeps with was complaining that he normally nuts 3+ times in a session and that he must be giving it all away to a “younger, hotter, girl”.  Yeah…still trying to discern how full of it he is but I guess you never really know with men.  Some of them just looove to talk like they are all about you, when they are not. 

I’m leery.  But I do like him a lot.  I just don’t want to fall for all the stuff I know I have a tendency to fall for, and he’s really laying it on thick!  He’s like “I want to be your Daddy”, “I want to take care of you”, “you make me want you all to myself”, “I’ve been liking you for a year and a half”, “You’re so beautiful and I like you so much I could wife you up”, “if I’m not careful I am going to want you to have my baby”, “I’m gonna have to get snipped so I won’t want to make you pregnant”, “I don’t want to just fuck when we are together, you are too beautiful for that, I want to treat you special”, “other girls aren’t like you” and “I get depressed when you leave”.  He’s even told me “I love you” a couple times, in bed.

I’m trying really hard to keep all his words from affecting me because I know men say things they don’t mean. It’s just so hard sometimes to be able to tell.  He calls me a couple times a day and likes to call first thing in the morning too.

Anyhow, back to anal.  That’s another thing he’s been on.  Wanting to be the only guy who I am willing to have anal with.  I’ve suspected since the beginning he was angling for that and he’s made it pretty obvious with the stuff he does during sex to try and “prep” me. 

He’ll get his tongue all up in there and spit on it during sex and try and slide his finger around the hole.  He’s asked about anal in the past, and that was the first thing he wanted to know if I’d done with the other guy at the swinger party.  He said I should save it for “Daddy” and then was like “just kidding” but it was obvious he wasn’t really.

Surprise, surprise, this time he went for it.  Before our second round of sex he brought out a vibrator.  It was a vibrating dildo, with a smooth gold surface, but no attachment for the clit, like the one I have.  He put it in me and turned it on.  I’m not sure how much the vibrations actually do INSIDE me because it doesn’t feel like much but it still felt good. 

He moved it in and out and eventually started playing with my ass, licking and eventually trying to stick a finger in it.  He went in for regular sex with me on my stomach, while getting things extra wet, playing with his finger and with the vibrator in front. 

Later, he slid his dick out and started rubbing it around my asshole.  He slowly started trying to ease his way in.  I tensed up a bit but didn’t resist.  He was sweet talking me a bit and promising only to put in “just the head” (yeah, yeah, we all heard that one in high school).  After moving it in and out just a little bit, with the head, he grabbed a bottle of Liquid Silk and started pouring it on. 

That helped it get in just a little bit further, but not much.  He held me still for a while with it in place and would start to move but I’d whimper and he’d pull back a tiny bit or go in just a little bit more.  He maybe got a third of his dick in after a while and was slowly rocking back and forth.  At one point he said he was going to cum, but didn’t.

Then he pulls out and goes RIGHT IN MY VAGINA.  OMG.  I am totally freaking out, thinking he is going to give me some kind of bacterial infection, but I didn’t say anything and he finished off.  I’m still trying to decide how to tactfully bring up to him that I don’t want him to EVER do THAT again.  I am REALLY susceptible to infections, even as a kid I was super sensitive to soaps or bubble baths or anything in that area and have always had to be very careful and hygienic. 

We cleaned up and had a couple more rounds of sex.  He tried to go in my ass again but it was SORE (and still is, hours later) so it wasn’t working.  Since I left, he has texted asking if I am going to let him put it all the way in and that that would make him happy.  Yeah, well, we will see… 

Just a little bit ago Mr. Motorcycle texted and I was busy writing this blog.  He asked if I was getting my freak on and I said “I wish”.  I didn’t mention the fact that I saw the Referee today, because he’s asked me not to tell him if I sleep with other guys.  His response was “yeah, you save that shit for me”.  I was like “is that what you want?” and he said that is one of the things he wants.  I thought we’d gone over this.  Sigh….