Broken – I Can’t Believe This

It was a few days after I spent that first night with her and she was different. I couldn’t tell what… just in those few days, but she gave me quite a few “you better hurry” jokes. But I brushed them off as her being charming. We liked to needle each other in a fun way. It was part of our rapport.

Broken is a story that is best read Chronologically to start from the beginning – Prologue

It was a few days after I spent that first night with her and she was different. I couldn’t tell what… just in those few days, but she gave me quite a few “you better hurry” jokes. But I brushed them off as her being charming. We liked to needle each other in a fun way. It was part of our rapport.

My family vacation was coming and likely the last one I would probably have. And I really needed to switch gears and prepare for myself. But it also signaled a time and space where it would be a month til we could see each other.

She would go away a few days after I left and then be back a few days before I got back but then would leave again. If it sounds confusing it was. We just knew we wouldn’t be able to see each other til late July. Hailey always said “I hate when you go on this trip”. I never understood this she even said it last year even before she was separated. Not to mention she was going away with James and the kids after her separation. And I wondered… “how is that any different you have only been on your own a few short days.”

In my logical brain I knew that there would be a transition after separation. A moment of sadness and a hard time logistically as you entered a new phase of family and spending time away from the kids. It wasn’t this way with her. She was instantly in single mode. I thought- Ok this is probably what it’s like after 14 years of marriage. She had already been out with me and girlfriends just in the first week. But I thought that is just Hailey

Then on the day I was leaving we were messaging and I was trying to see if she had places to stay and enough plans. She said she would be homeless for about 10 days and would try to figure somethings out. This broke my heart. I even offered to pay for a room for her.

Then in the course of our conversation she blurted out “something is different” and “things have changed”. I asked “what are you talking about?” “Well I am just dating a married man now” Hailey said. “And one that isn’t available”. I honestly didn’t know how to respond. My heart sank. Didn’t we tell each other we loved each other just the other day? How could this be?

Then she hit me with it… “Someone asked me out to dinner and I was flattered.” Instant heartbreak. There is something about me where when someone no longer wants me I shift into goodbye mode very quickly. So I started to shift into final language. But she reeled me back. She said “I am not going but I need to think about this and where I am at.” Even as I write this now I can feel my heart rate elevate and get warm from adrenaline. I am a cut to the quick type of person so I ask… “Does this mean you are done?” She said “not necessarily”. Just ugh.. to the bathroom to cry before I get on the plane.

Looking back Hailey would always drop these leading and open ended statements like “Someone asked me out to dinner and I was flattered”. It was the first time I ever thought I may never see her again. And unfortunately it wouldn’t be the last.

Broken – Hailey’s Single

It was June and the house was sold. The process of moving had begun and James had already found a townhouse in the city right next door. Hailey found a place that wouldn’t be ready til August.

Broken is a story that is best read Chronologically to start from the beginning – Prologue

It was June and the house was sold. The process of moving had begun and James had already found a townhouse in the city right next door. Hailey found a place that wouldn’t be ready til August. Here is why you look before you leap. I questioned this and but she had a bunch of vacation planned and would spend some at her friends, AirBnb, and nights with the kids at James’.

I hated that plan but there was little I could do. Her first night as a newly single person I managed to free myself. We met for drinks but she was upset because I didn’t offer her dinner. And of course we could have had dinner. But I never remarked that this was a special occasion. Was I supposed to? There is sadness in this day as well certainly? I wasn’t sure a celebration was in order.

She never mentioned it to me until later and looking back I know why. But we had our drink and then decided to have some fun in the parking lot. I wanted to give her such pleasure. She looked really good. I laid her down in the back seat and I am sure she would be convinced I would fuck her. But I wanted to just give her an endless supply of pleasure. I may have had it in the back of my mind that she was a free person and it felt sudden that it happened. But I wanted to remind her no one could make her feel like I could.

I found myself kissing her chest and pulling up her sundress. Then putting my hand on her and touching her. Feeling her wetness and rubbing her. She really loved when I touched her and I really liked to touch her as well. I slid my fingers inside and felt around for her spot. Once I find it, I relentlessly touch it with a variety of speeds and pressure I want her to feel it all. I put my mouth on her clit and make out with it if it were the lips on her face.

I kept going until she came. I love that moment where it all gets tight you can feel it and feel the abdomen, the arch in the back, the collapse on your way down. It is my very favorite thing about sex when giving that to someone. And then when satisfied I climbed on top and pushed myself in her. Looked deep into her soul and made love to her.

It was a good night but she was particularly harsh on letting me go that night. I had to be home at a normal time, but she had all the freedom. Something was different. I knew she had a patience problem but already? And instantly I felt her angst around the juxtaposition of our situations. Overnight I felt insecure.

Note: Bonus extra daily post for a couple special readers (Nora, Cara) you guys keep me going and encourage me when this story can be hard to tell at times. Thank You!

Broken – “I Love You”

We were about 3 months into our relationship and after a series of sexcapades everywhere and anywhere we decided we wanted some romance and spend a day with each other. I got a room and checked in. She was there shortly after me.

That day we decided to make love it was the really first time we altered our routine of any typical fun we had. We undressed got under the covers and kissed forever. The way we kissed was electric and it was but there was something special about that day. We both felt it.

I kissed her body all over but didn’t go down on her I just wanted to feel her skin on my lips. I never even touched her which I loved to do. I just climbed on top and said “I just want to be inside you”. We barely had to move it felt so good. I went slow and deep the entire time. Kissing her, eyes open staring into her soul and she did the same thing.

My heart was so full. I would grab her ass so I could pull her while I pushed just to be deeper. I love this part. It was connecting with each other in a spiritual and physical way. She was in heaven I could tell by her moans and the way she looked at me. When I was with her I always gave her my heart even when it was on the more dirty side.

While just inside of her not moving and looking at her and her looking back at me she said “I love you”. Months ago I would have thought this would have floored me made me retreat and call and end to the whole thing. Without hesitation though… “I love you too.” That’s it we were in love and it was a near perfect movie-like moment – but ugh, now what…?

Broken – Sweet Side and Red Flags

While the foundation of our affair was based on sex and intimacy it started to balance itself with a very sweet side. That is my default mindset is to be nice and kind always steering it to stability and peace.

Broken is a story that is best read Chronologically to start from the beginning – Prologue

While the foundation of our affair was based on sex and intimacy it started to balance itself with a very sweet side. That is my default mindset is to be nice and kind always steering it to stability and peace. Hailey loved this about me. A few times she called me the most adult person she had ever met. I found this fascinating because she was such a social butterfly and knew so many people.

I admired that about her, she had an ability to invite people in and was very open. I am more naturally introverted and an empath. So my natural state is to feel people out before I trust or let them in. We both found the differences in us attractive. It balanced us. I would ground her and she would push me. It was Yin and Yang.

We would talk so much about our lives and childhoods we shared our traumas and fears, hopes and dreams. Really everything and anything. Nothing was off limits. It was refreshing but also could cause a few issues. She had a side I could never, and even to this day, figure out. It would manifest itself in cold periods and harsh statements. I never knew where this came from.

Early on in our relationship, one night, she wanted me to pick her up from a friends house because she was drunk and wanted sex. It was 10PM on a Thursday or Friday. I never had left the house at that hour of the night for no reason. Of course I wanted to, I think she did as well. But her reaction to “I would love to, but can’t.” was strange to me. She didn’t care in that moment what kind of ask that was. She wanted what she wanted, when she wanted it. Along with being overtly upset she gave me a little shit about my dynamic at home. About how little freedom I had and I had no balls.

She wasn’t way off base but my dynamic at home was always impasse. If my wife didn’t like it I couldn’t do it without it affecting us for months. It was very black or white with her. I am a peace keeper so it was natural for me not to push her boundaries. Going out at 10PM suddenly, I may as well be telling her “I am going to pick up my girlfriend”. I wasn’t going to get away without a reasonable explanation and there wasn’t one. After our exchange she was like goodnight abruptly and I didn’t hear from her the rest of the night.

I was actually hurt and sad, I thought I had lost her. Her life was different from mine and she had this freedom, or so she thought, and I did not. And she judged me for it. I didn’t realize at the time what the root cause of this was and it would take me the better of 2 years to figure out. Because the next day she apologized and said. “I am sorry you are a nice guy and I should be asking or expecting you to come out in the middle of the night to do that.” I accepted and said “no worries. I am sorry I couldn’t make it happen for you.” This was a red flag that I missed. I apologized for something I had no business accepting accountability for. It was a pattern we would repeat many times…

Broken – More Sex

It had been about a month and I probably had more sex with Hailey more than I had in the last 4 years of my life. We did it everywhere in my office, hotels, cars. Pretty much where ever we could.

Broken is a story that is best read Chronologically to start from the beginning – Prologue

It had been about a month and I probably had more sex with Hailey more than I had in the last 4 years of my life. We did it everywhere in my office, hotels, cars. Pretty much where ever we could. We didn’t even need to be naked or playing, just our kissing and fucking mostly clothed was still unbelievable. Our chemistry and connection were that special.

We would sneak in so many one hour parking garage/lot visits. But my absolute favorite was when she showed up in camo yoga pants and sports bra. I just felt always so lucky to be with her especially when she looked like that. I am not a shallow person at all I required a deep connection. And because it was there her beauty made it more so. One could argue that she wasn’t the most beautiful girl I ever dated or had been with but she was the one I was attracted to the most. Anyways back to the parking lot…

She pulled in and she always drove the most notable cars a big SUV. She pulled in next to me and we hopped in my back seat. I had pretty well tinted windows there wasn’t much anyone could see. I thought it was a typical day and we would kiss and she would climb on top of me and we would fuck until I came inside her.

This was different. She pulled down my pants and was on her knees on the floor of the car. She looked right at me as she started to wrap her lips around my dick. This is what sexy and sex is supposed to be. She made lots of eye contact and varied between making love to my cock and going faster and more deliberate. I could tell she wanted me to cum in her mouth and that only accelerated the process.

She continued to look up at me when she would kiss and lick the top of me and make me shudder every time she would go fully down on me. I knew it was coming soon. Normally i might close my eyes or wince because it is so intense. Especially when I am getting a blow job. But I stayed looking at her. I say what I mostly say. “I am going to cum” she looked at me and I exploded inside her mouth. She swallowed most of it but did something I didn’t expect she let some of it drip out of her mouth as she smiled at me. Mind blown, she really new how to deliver sexy visuals.

She then climbed on my lap and we kissed. Breaking the fourth wall here… Guys let a woman kiss you after. You never taste it and it makes them feel better. It’s an easy thing to get over as the reward is great. Off my soap box. Another great experience in between all the others. This one was filed away in the spank bank and is used quite frequently. How many more could we have like this…

Broken – Routine and First Real World Encounter

Broken is a story that is best read Chronologically to start from the beginning – Prologue

We would alternate between a few hotel visits and my office. We would see each other a few times a week. We would talk extensively throughout the day. She would always say “tell me something…” and that was her cue to have me write another story about her. I made a video for her. It was me cumming. Fortunately i was gifted with the ability to shoot and I had a pretty full ejaculate. For a woman who was sexual they would like it.

She would continue to send me sexy pictures. I was over the moon. It was getting sexier and sexier. But we were also having a dialogue we started to peel back layers. It was easy to talk to each other. We operated on a similar frequency. And even our non verbal communication connected. We had a similar sense of humor and had the ability to laugh at ourselves.

As we were talking we both realized something. It’s school orientation… “Shit!” I thought. We will have to be in the same area together. This stressed me out and maybe excited me a little bit. But much more stressful. I arrived early with wife and kids. I was honestly hoping we would arrive at very different times. After all she wasn’t always on time…. Yep “Nope!” She was one of 10 people standing in the lobby. We locked eyes half smiles. She looked great as usual. I wanted to grab her and kiss her right there but for obvious reason would never.

She came with just her oldest and friends. Most of the kids sat in the back together and the adults sat closer. I knew she was just a couple rows behind me. I was nearly sweating as I am was thinking i hope I am attractive from this angle. The orientation was over we half smiled one more time.

I got home she messaged me… “You looked so cute and good I couldn’t stand it”. I was riding so high. I haven’t felt that way in over a decade. She was beautiful and fun and knew how to make me feel. We survived the first in-person run in. And it was a little fun. What would come next was all I could think about…

Broken – First Hotel Date

So I drove to the hotel. It was midweek and I had to check in at 11AM. This was always the worst feeling. I am naturally a risk adverse person and there is so much risk. You give them your name and a form of payment. There is a record of you being where you are not supposed to be.

Broken is a story that is best read Chronologically to start from the beginning – Prologue

So I drove to the hotel. It was midweek and I had to check in at 11AM. This was always the worst feeling. I am naturally a risk adverse person and there is so much risk. You give them your name and a form of payment. There is a record of you being where you are not supposed to be. Not too mention there is always a strange look from the front desk about checking in mid day when you live near by. You would think they would just be trained to ignore it but maybe I was thinking they were looking closer than they were. Anyways… swallow hard and get past it.

I was there earlier than her. I brought some alcohol. I needed to calm my nerves and it always gets me more in a mood sexy, risky, more aggressive. Being an INFJ empath there is a natural state of trying to feel the vibe and analyze the surroundings. But i needed to be bolder and less in my head. Booze helps. I downed two drinks of vodka with a mixers. Always my go to. I would plan to have one when she go there.

I nervously awaited her arrival. Excited and ready as well. She arrived and brought some wine with her we both had a drink before I pulled her in and kissed her. It was magic when we kissed. I brought her over to the bed put her up there on her knees and grabbed both her arms and with one hand pinned both her wrists behind her while continuing to kiss her. I even teased her a little and this drove her a bit crazy. She looked so sexy. She was in jeans and a shirt. We got her out of those quickly. I wanted to have lots of foreplay and had her naked before I removed one item of my own clothing.

I undressed her and she was naked still had tan lines from her trip and my god she looked sooo good. She had hips to die for, her boobs were amazing, fake but not terribly so. Her nipples were perfect. I kissed her and started to touch her. I rubbed her clit until she was wet and then slid my finger in her. There was something about her that brought out my inner primal side. I grabbed her there as if I owned it. And she loved it. I played with her, went down on her but she wanted me. I started to relinquish back some control.

She unzipped my pants and took me in her mouth. It felt soooo good. She gives a sexy bj. I continued to play and touch her while she was sucking my cock. The more I stimulated her she moaned with her mouth full of me. I love that! And then she said what every guy wants to hear. “Fuck me please”.

I climbed on top and pushed inside her and started to fuck her slowly. I think she wanted it rough. But I was afraid I would cum in like 10 seconds. I started to get nervous again after that last finish. I should have just taken control again and told her I wanted it this way but didn’t. I have had so little sex in the last several years that I didn’t have any feeling for my stamina. I started to go faster and anytime i felt it getting close I would slow down. Except one time I felt it getting away from me. I pulled out of her and couldn’t tell if I stopped it or I came. “Oy vey” was all I could think in my head. What just happened? I don’t even know. For christ sakes Matt get your shit together.

Whether it was an orgasm or a faux one I still don’t know to this day but I went limp. And all I could think of “Are you fucking kidding me, I get a hard on in a decent wind. You have a hot girl here what the holy hell is going on.” I couldn’t explain it. All i would tell her is that i get overheated, which is true, but I am not sure that was the case.

I went right back to playing with her for a bit. She never made me feel less than because of it but i knew she wasn’t happy. But I got playful. I took her by the hand and brought her in front of a mirror. I kissed her neck and ran my hands over her body and told her how sexy she looked. And she liked seeing my hands run over her tanned body. Then I felt it again, “Thank god” This time I went big I kind of half picked her up and shoved her on the bed with force. She gasped and I fucked her while standing at the end of the bed while she laid on it. Finally a good fuck and I came.

This was a great day probably one of my fondest memories of her. It is when our connection went deeper. I literally had meaningful conversation with her with my fingers inside her grabbing her pussy. It was silly, fun, sexy, and deep all at the same time. Could it ever be this good again…

Broken – The Aftermath

So we had our first date and I went home on cloud nine but also in a little bit of anxiousness. I wondered would she focus on the connection or my awkwardness. It could be endearing but some women like their men smooth and sophisticated.

Broken is a story that is best read Chronologically to start from the beginning – Prologue

So we had our first date and I went home on cloud nine but also in a little bit of anxiousness. I wondered would she focus on the connection or my awkwardness. It could be endearing but some women like their men smooth and sophisticated. I was capable of this but early on with her I was a mix of both. But would there be more?

We spent the next couple days talking and she wanted to see me again… Yes!! She had this amazing ability to make me feel so wanted. She would say “when can I see you again” I would live off her asking that for quite some time. So much so I forgot to ask her at times.

We talked about what’s next and the challenges of knowing each other and being in such close proximity. She would remind me all the time “2.7 miles”. She said “don’t fall in love with me” and explained men seem to do that with her. I told her ditto… I have always been described by those who know me with a great range of sweet and sexy. By default I am a nurturer and give people I care about my all. So I have had my share of girls that “fell” for me.

She asked what happens if it gets too serious I said “we will just have to say goodbye”. I meant every word of this and she said “Ok”. I never had an intention of leaving my marriage. Then she asked “how long do we do this” I said 4 years. That was the time when our kids would have graduated high school. She said “OK!” I was surprised initially by that. As i said it tongue in cheek but she was enthusiastic about it. And i thought to myself that would be awesome and could we get there.

After we had that discussion we quickly changed back to ok when and where are we meeting. We talked about sex, I sent her another story of erotica in what I would do to her, she sent me a dirty picture and I suggested why don’t we get a room. Her response “Yes!”. I set the day. It would be day time. I got excited and nervous again how will this go…

Broken – The First Meeting

As we narrowed our meeting to a day and time we had some obstacles to overcome. It would be a couple weeks from when we matched to the time we could meet. But that day was coming. In between that time I would send her long texts of erotica.

Broken is a story that is best read Chronologically to start from the beginning – Prologue

As we narrowed our meeting to a day and time we had some obstacles to overcome. It would be a couple weeks from when we matched to the time we could meet. But that day was coming. In between that time I would send her long texts of erotica. Stuff from my head that I would like to do to her. She really liked it. I tend to think different than most men when it comes to sex and the build up and she really appreciated that.

We decided to meet probably on a Wed. or mid week. We both had freedom from work and she said she could meet me near my office. At that time I was working almost solo out of my office. I was the only one ever there. There was a decent restaurant across the street. I invited her to meet me there and I would be at the bar. I arrived early and she arrived late… she was always a few minutes late. She is chaotic by nature but it wasn’t egregious, or at least at that time.

I was nervous and excited and finally saw the top of her head. She is around 5’4 with blonde shorter hair and petite but curvy. She has a beautiful all american girl next door face, but knows how to carry herself and she adds sex appeal. Think Jennifer Anniston. She spots me and comes sit next to me. We introduce each other and start with conversation.

Our conversation flows easily, she likes to listen to me and engages very well in dialogue. We even have a funny moment where I gasped at something we both liked. She teased me but I liked that. Because earlier when all was revealed she also teased me that she thought I was gay. Which would be an ongoing joke for a long time.

She made me feel confident and brought out a good kind of playful even risky side to me. This would factor into many different encounters in the future. But in that moment it felt great. I had to take a phone call in the middle of our lunch as she finished her french onion soup. I quickly came back 10 minutes later and she sat closer and i opened myself to her. I could feel this going in a sexy direction. She even ran her hand up my thigh I thought she would stop well short of my package. But nope she grabbed hold. I was in heaven.

At that moment I asked her back to the office so I could kiss her. She accompanied me back and I made her feel at home took her jacket and then grabbed her face gently and kissed her sensually and passionately as if life depended on it. And wow!! It was electric we kissed the same exact way. It was insane.

I figured that is as far as it would go as that this is a pretty good start, but she turned around and pressed her amazing ass against my crotch and I couldn’t believe what we were about to do. I pulled her pants down with her help and then unzipped myself and pushed my way in her as quickly as I could. As I bent her back over my desk. It wasn’t about rushing, it was about feeling her as closely as I could. This was sexy but there was something underlying our connection. I began to grab her hips and thrust into her. She did one of the sexiest things a woman can do she looked back and looked me in the eyes.

I continued to fuck her right there in the office. And I thought wow! I can’t believe I am doing this. She wanted me on top of her. So she laid down on the floor and i climbed on top. I started to push my way in her and give her some more on the floor. But the funniest thing was happening. My knees were getting so rug burned it was distracting me something awful. I was also starting to overheat. So I was instantly a mess. I said let’s change. So I pulled out and stood up. I was so out of sorts that I started to cum while she was laying down and I was standing up. It went everywhere. On her, the floor, I was laughing, she was laughing. But I was also mortified. I looked like a clumsy oof and it kind of didn’t finish the way that encounter should have but, she has a great sense of humor so it kind of also worked too. She stayed a bit. I kissed her goodbye and thought… “will my embarrassing finish make her ever want to see me again” all I could do is text her later and hope…

Broken – Texting

After sending my message thanking her for understanding I was expecting a “you’re welcome” and that was about it. She started to engage more and started teasing me a little in a very flirty way. She said aren’t you curious to know who I am. I said “Of course!!”

Broken is a story that is best read Chronologically to start from the beginning – Prologue

After sending my message thanking her for understanding I was expecting a “you’re welcome” and that was about it. She started to engage more and started teasing me a little in a very flirty way. She said aren’t you curious to know who I am. I said “Of course!!” but respected her need for discretion. She gave me terrible hints. I had managed to figure out that she was a “School Mom” but that narrowed it down to 1200 kids. Not exactly zeroing in on it. But then she revealed something- she had stalked my Facebook account to which I immediately knew Facebook would give her up. No one really knows the algorithm for suggested friends but I am a tech person and knew that she would be in the suggested friends list based on her visiting my feed. Off to Facebook…

It didn’t take me long to find a school mom she was the second or third suggested friend. I knew we had met briefly before. But I wasn’t 100% sure it was her. I realized something else as I peered through her feed. I found a picture I ogled just months before. She was in a bikini and looked amazing. I knew back then she probably drove the other Mom’s crazy. So I started to get excited. Could this really be her? One of the hottest Mom’s in my town?

So back to texting her. I said I think I have you. She said “already?” I said “Yup!” I said are you “this person”? She said “oh my god how did you figure it out so fast?” I told her that her FB stalking busted her. And so here we were virtually face to face. What do we do from here? Most would think this is where it ends… We promise each other never to give the other one up and have a chuckle if we see each other and go on our merry ways. But there was this undeniable chemistry an ease of conversation like I had known this person my entire life.

From there we began texting. I didn’t know she was in the Caribbean with her husband. He was there on business and so she was alone by the pool or beach in what I could only imagine was something sexy.

I immediately started to flirt with her as I knew she wasn’t going away. We would exchange questions about sex… what do we like? what are we attracted to? history? fantasies? We covered quite a bit as she was there for 5 days. She even sent me a photo half naked and I almost couldn’t contain myself.

So what’s next… “Do we meet?” I asked. And she said “Yes! I am super curious.” But when we discussed it beyond that she would tell me about how picky she was. So it really tempered my excitement and even added nerves. I asked “when would you like to meet?”….

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