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!

7 thoughts on “An anal adventure…..

  1. Done correctly, anal should not hurt and should give you fantastic climaxes. The big thing is to slowly work the head in and once you’re in past the sphincter STOP. Then wait until the girl relaxes before starting slow short strokes and gradually get harder and longer.

    • He has done that but I still tensed up. It still hurts me and we’ve done it a handful of times now. This last time was better. He was more gentle and I was more relaxed. I let him do it for longer and it wasn’t too bad but he could tell when I was getting super uncomfortable and he stopped. I doubt anal is ever going to be my favorite thing and I bleed after and have pain for a while. Even now, its been a week since the last time and I’m a little sore. Maybe some women are just built differently than me, I’m not sure. I do get to the point where I kind of want him to do it again because he’s making me feel so incredible in other ways and I want to make HIM feel good. I think its more a submission thing than actually enjoying it though. It just doesn’t feel all that great to me, its super uncomfortable having something up your ass.

      • If it’s making you bleed, then you probably should rethink it or get a boyfriend with a smaller dick. LOL If you want to pursue it, maybe get a small vibrator or dildo and practice with it. Use some good lube also. My wife loves it and so do several of our girlfriends, to the point of preferring it. But if it hurts then it may not be for you.

      • I’m not that keen on anal stimulation at all, the only reason I do it is for him. 😉 Yes, it makes me bleed. He has used lube before but it did then too. This last time he had everything all wet and used his tongue there and I did better than usual but it still bled after. I don’t really understand these women that love it at all, lol.

      • Well it sounds like anal should not be on your bucket list at all. Having sex should be fun and if it’s painful and not fun then you shouldn’t do it. Well that is except for the nipple clamp and whips crowd! Wifey loves it and will even stick a finger or two up her back door when we’re having “normal” sex. She loves the climaxes from anal but to each his own and you just might have to stick with watching it on your computer.

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