Tag Archive | surprises

An anal adventure…..


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!

The orgy weekend culminates (part 3)


Okay, so when I left you, I was stuck at my grandma’s house, with a broken down vehicle.  Don’t worry though, I still managed to squeeze in some more sexual escapades.  😉  Bet you’d like to know how.

While I was having all these issues and trying to figure out what to do, I was getting texts from a guy I had met at the last swinger party.  He’s a 24 year old, very nice looking, biracial, bodybuilder.  He just got out of the military and is currently working as a bouncer at a nightclub, as well as working on his bodyguard license.  At the party, he’d had trouble getting it up, due to it being his first swinging experience, and he REALLY wanted to prove to me that he’s not always that way, lol.

It was actually kind of annoying because I was trying to get stuff done and when family heard I was in town, of course, they wanted to see me.  I have siblings there and they were like, what are you doing sneaking into town without telling anyone??  Thankfully, my family is not very nosy.  They didn’t press much as to what I was doing.   I just said I was at a party in the city.

God, sometimes I really get homesick.  I’ve been thinking for a long time I would like to move back up that way.  Maybe I’ll be able to make it happen here eventually, it would be nice to be close to people that could help me in times of need.  I really don’t have anyone here, now that I am divorced. 

My grandmother still lives in the same place she did when I was coming up.  It’s a mostly black neighborhood and the community is so different from where I am now.  Some people might consider it a “bad” area, but to me it never really felt that way.  Even though the people are poor, there was always someone there to help you out if you needed it.

My memories are full of summer parties in the street outside her house.  Parents, grandparents, teenagers and young ones all running around, dancing and drinking.  BBQ’s, people sitting out on their porches and always available to talk.  Being one of the only white kids in the neighborhood, strangely, I never really felt out of place.  Even now, I love that the neighbors look out for and help my grandma.  You don’t see a whole lot of that here.

I spent much of the afternoon with my sister’s friend’s dad, a dark skinned, black man in his mid 60’s with BLUE eyes.  I was like where’d you get those eyes and he said his great grandfather was Irish and Indian (Native).  He said my baby sister is like a daughter to him and that I drive just like she does, hotrodding it, lol.  He was getting onto me and later I was getting onto him because he told me he refuses to get a vasectomy because of his age but that he also doesn’t wear condoms when he is playing around.  No idea how we got to talking about that!  lol  At the store, when we were buying transmission fluid, we ran into one of his cronies, an older white guy, who thought I was his girlfriend.  He was like, NO, she’s like my daughter!  Haha

Anyhow, my vehicle is shot, but by the time we’d taken care of that and I’d run over to one of my sisters houses for a bit, and showered, it was getting really late.  Mr. Bodybuilder wanted to come to town and hang out anyway.  He said we could go for a movie or out to eat.  I’m thinking it might even be too late for that (it was nearly 10 pm). 

Meanwhile, I had realized that I left one of my favorite bras at Mr. Host’s house.  Dammit!  He wasn’t bothered though.  He said if you come and get it you can stay the night. 

Hmmm…that would also put me near Mr. Bodybuilder.   I talked to my grandma a bit and it was decided I would take her car to drive back home. She was cool with me heading back out to stay in the city that night.  I warned Mr. Host I might be pretty late but he said that was cool, as long as I was staying over.

Mr. Bodybuilder and I decided to go out to eat.  We talked and hung out for awhile and then he said maybe he could get a hotel.  I was thinking, there is no way I want him to spend $$ on that, when I will have to jet fairly quickly, in order to get over to Mr. Host’s, but I didn’t tell him why.  I just said I would have to leave before too long and maybe that wasn’t a good idea.

He is currently staying with his sister, on her couch, lol, as he JUST got out of the military and hasn’t had a chance to get settled with his own place.  He says he doesn’t want to waste his money on a crappy home when he can earn a little more and get something better. 

We decided we would just go over there, but I’d have to be really quiet because she and her boyfriend (and toddler) would be asleep.  Oh man, this felt like high school all over again, haha, sneaking in someone’s place, but…okay.

We slipped in the front door quietly and onto the screened in back porch. It was cold. I’m thinking seriously?  What am I just going to bend over?  No, he had another plan.  He wanted me to sit on this tiny little nightstand.  It looked like it could easily tip over, but I did.

I sat there and he had me pull down my pants.  They are like legging style and I was wearing knee length leather boots.  Not conducive to this AT ALL, lol.  I had to put my legs over his head.  He went down on me for a little bit and then put in his very hard dick.  We fucked with me on the table with my legs around him, to where he was kind of trapped.

We kept hearing noises and he told me to keep an eye out for shadows on the wall in the kitchen.  Suddenly, someone turned on a light.  We jumped and I almost fell over, lol.  Had to get my legs up over his head and hobble around the corner to pull on my clothes.  We were trying not to knock into stuff.  Whoever it was, wasn’t there long.  The light went back out.

By then we decided we’d better head outside.  We snuck through the backyard and the high heel of my boot caught in a hole in the ground in the dark.  I fell and banged up my knee pretty badly on some cement.  He kept apologizing and we went to sit in his car.

It was getting really late and I was afraid if I took too long Mr. Host would fall asleep, leaving me nowhere to stay for the night.  Mr. Bodybuilder kept pushing to continue our fun and saying we could go at it in the backseat of his car.  I opted out, citing my knee and it being really late.  He reluctantly said okay but that he thought I was really hot, that this was exciting and he wants to see me again.  He said normally he doesn’t even like women with kids but thought I was in great shape.

Alright, alright, that was nice but I had to go.  I took off and headed to Mr. Host’s.  He had been lying down for a bit but managed to get up and answer the door, despite it being 2 am. 

Oh, WOW, am I glad I went back over there!!  We got in bed and proceeded to have some seriously hot sex, over and over, like ALL night long.  He came in me about 5 times before having to get up for work in the morning.  I actually made him like 45 minutes late but he said that’s okay because he’s the boss. 😉

I was really surprised at how good the sex was with him!!  I wasn’t expecting that at all.  It was like fireworks!!  I don’t know if it was just because I was sooo horny or what!!  I WAS ovulating, according to my little calendar on my phone, where I keep track of my menstrual cycle.

He was very dominant and got pretty rough.  He was pulling my hair, choking me, biting my neck,smacking my ass, you name it!  This is the same guy, who at dinner with that one woman had agreed with her that he could never choke someone in bed!  His hand was probably on my neck like half the time we were fucking!! He must have really took what I said about kind of liking it to heart. 😉 😉

Wow, in the morning he even got out this wedge shaped pillow and had me bend over it to where he could really penetrate deep. It felt good and the whole thing was really damn hot! He has been texting me for the past couple days going on about how freaking good it was! It almost took my mind off Mr. Firm, but not quite, he’s still hot as hell. 🙂

Mr. Host is now saying he’d like to take me to a bed and breakfast sometime, where we can fuck all day and all night and do nothing else. Sounds like fun. I’ll have to keep you all updated. 😉







I interrupt my regularly scheduled blogging to bring you this little bulletin.  I woke up to a text this morning from the Professor.  It said “check your front door”.  So I went out there and looked and he had left a box of donuts.

I’m not sure how to take this.  I thanked him and asked why he did it and he said he thought my kids might like it.  It’s a nice gesture, but….is it really?

Whyyy would he do this NOW?  It’s almost like he saw that I am slipping away and wanted to try and get me back on the string again.  Or maybe he is trying to fuck with my losing weight so I can look hotter for new guys, ha. I wonder if he peeked on the swinger site and saw that I had signed up for a new party.  It’s possible to discover that info from my profile if he clicks on a button that shows your events attended/attending.

Maybe he is just trying to be nice and I’m assigning all kinds of suspicious motives.  I don’t know, but now I’m really confused.  I guess he could just feel sorry for me or honestly be thinking about the kids, but it’s been 6 weeks.