Surprise Sex With Top Gun

It's not often that a Kitty gets a re-do with an Ashley Madison guy. I'm not sure if any of you remember Top Gun but Kitty met him way at the beginning of my Ashley Madison days...three years ago to be exact. We met for Chai at Starbucks, texted a little bit after that and then lost touch. Kitty got the impression Top Gun was trying to ditch me so I let him go. He was single at the time and Kitty of course was married to Angry Guy.

Well, the other night while Kitty was checking out the latest and greatest on Ashley Madison, I saw Top Gun logged on to the site. I emailed him immediately. Before long he emailed me and then called. We made a date to meet the next morning at the very same Starbucks and potentially a walk on the beach. He made a few comments about breaking in his hotel room. Oh yeah! Kitty forgot to mention that Top Gun commutes back and forth between the East Coast and the West so while he is in town, he is in a pretty nice hotel.

So we meet at 10:00 "SHARP" because Top Gun is a retired military guy as well as a pilot. He has his chai and Kitty splurges and orders a pumpkin spice latte and a blueberry scone. Top Gun decides to order himself a scone as well. So we chat like old friends. We recount the past three years. Top Gun's looks haven't changed at all. He is tall, dark and handsome. I later find out that he is half Portuguese. After coffee I offer to take Top Gun to the beach. Even though he has lived in the surrounding area on and off for the past three years he has yet to see my favorite beach so we go, we walk then we sit in the sun on the most gorgeous morning of the summer so far. We flirt and we begin to touch and then Top Gun kisses Kitty and suddenly we are on a date.

We decide to go back to his hotel. In the car Kitty confesses that I prefer men who use iPhone over the alternative. I'm thinking since Top Gun is using his iPhone he would appreciate my humor but he just thinks I'm crazy.

Once back at the hotel Top Gun confesses that he requests the top floor so that he can get his workout by walking the stairs and even though Kitty is way out of shape at this point I walk up four freakin' flights of stairs in the hopes of feeling Top Gun's cock inside of me.

Although breathless Kitty makes the climb and we enter Top Gun's suite. Kitty kicks off my sandals and begins to take off my jewelry. Since Top Gun was making all sorts of comments over coffee and at the beach then immediately apologized Kitty said, "You can say whatever you want to me here. Don't be shy and don't apologize."

Top Gun began to kiss Kitty. We remove each other’s clothes. Kitty exposes Top Gun's beautiful, long erect cock. He moaned the moment I touched it. After a brief conversation on the beach where Top Gun revealed that he doesn't necessarily crave oral the way most men do, Kitty opted not to suck on his cock right away.

Top Gun immediately took charge. He moved Kitty to the bed and immediately put his hard cock inside of my already wet pussy. We all know by now how much Kitty loves a man who takes charge. Top Gun worked damn hard and thrusted for a good long time taking breaths to ask a few questions. "How often do you expect to meet when I am in town? What are you going to write about me in your blog? Did you cum yet? Can I cum inside of you?"

When I explained that it would probably be okay but that I could still possibly become pregnant he asked, "Hypothetically what would happen if you became pregnant?" Now, when Kitty is being fucked especially when I am being fucked hard like Top Gun was doing, I can barely speak much less think so my answers were brief and now looking back I suppose we should sit down and discuss these questions probably with clothes on and probably without Top Gun's cock inside of me.

When Top Gun pulled his cock out of me for a brief moment I was able to slip it in my mouth. I'm thinking he decided he liked it after all since after a few short minutes of me sucking the head of his cock he asked if he could cum in Kitty's mouth. Ahh another convert.

Now something happened when Kitty was with Top Gun that has never happened to Kitty before with an AM lover. After Kitty and Top Gun both came we lay for a moment in silence. We slipped under the covers then Kitty and Top Gun curled up together in Top Gun's plush bed and fell asleep in each other’s arms.

Not Out of The Game Yet

Kitty has to admit that I was feeling a little low at the beginning of the week. I had waited to hear from the Cowboy in hopes that after his awkward text he would call Kitty to reschedule our visit out to his farm. When Sunday came and went Kitty had all but given up hope. Typically Kitty makes excuses when this happens…maybe he was busy…maybe he forgot…maybe he had a terrible tractor accident and needs Kitty to nurse him back to health. But Kitty has grown over the years and in the end I was resolved to the fact that the Cowboy was simply not interested in a friendship with Kitty. Since Cowboy is a client and as Surfer Dude pointed out, “It’s unprofessional to fuck a client.” Kitty had no choice but to let it go.

There is one problem with this in Kitty’s mind. Kitty just hates the awkward silence. So as Kitty was mentally preparing to fuck Esq. I began to think. Kitty has to resolve this silence with the Cowboy and make sure we are okay as Client/Kitty.

The Cowboy’s folder is front and center on Kitty’s desk. I can’t do anything without glancing over and looking at it. I had to do some work for his brothers, sisters, mother so his name has been in my head for weeks. Kitty can’t get away from thinking about the Cowboy. So Kitty did the ultimate high school girl move. Kitty called the Cowboy under the pretense of his situation as a client.

Kitty: “Hi, it’s Kitty from ****”

Cowboy: “Hey! What’s up?”

Kitty: “Nothing. I was wondering if you’ve heard anything.”

Cowboy: “No, I thought that maybe you had and that’s why you are calling.”

Kitty: “No but we should hear something soon. Please let me know if you hear anything and I will do the same.”

Cowboy: “Okay and HEY call me on Sunday. If the weather is nice you and your daughter should take a ride to the farm. It will be a nice day.”

So Kitty’s heart…or what’s left of it took just a little leap as the Cowboy and I discussed the weather and farming and business. His voice is so sexy to me and although he uses words like “ain’t” which typically drives Kitty crazy, I can’t help but get a little wet when I think about fucking this man who is really the epitome of the American man.

Kitty does have a little confession to make and I know those of you who know Kitty in person are going to give me all sorts of shit for this but Kitty can actually see myself potentially “settling down” with the Cowboy. Kitty can almost see myself being…MONOTONOUS…MONOGAMOUS.

There is something about the simplicity of his life style that appeals to Kitty. He gets up in the morning works hard until the end of the day then eats and goes to bed. Kitty doubts the Cowboy has a computer, Ipad or any electronics other than his cell phone. All of his business dealings are done through his mother and through Kitty. He has no time for nonsense and doesn’t quite get Kitty’s humor which is abundant to say the least.

The Cowboy is the kind of man that Kitty can see spending holidays with sitting around the family dinner with his absolutely huge family which I already know quite well via telephone. Oh sure, I know. Kitty is getting ahead of myself and believe me Kitty realizes that it is highly unlikely that I will get my fairy tale ending with the Cowboy.

The good news? Kitty is not out of the game yet.

Cloudy With a Chance of Threesomes

Were any of you wondering how Kitty’s threesome went last night???? Wouldn’t you know as soon as Kitty posted about it Esq. texted to tell me that Sidekick was traveling for work and would not be able to attend “this time”. I’m sure my disappointment was obvious but then Bestie Bill and I agreed that Kitty needed to drop the subject. We had a feeling that Esq. might be getting a little jealous and may have re thought sharing Kitty with Sidekick. First off there is no way Kitty can have any direct contact with Sidekick. Strange don’t you think? When Esq. explains it, it makes sense to a degree but COME ON GUYS!!!

So for the time being Kitty dropped the whole threesome issue but secretly hoped that Sidekick would be at Esq.’s vacation home waiting when Kitty arrived. “Text me when you get on the bridge” Esq. said. Kitty thought…”maybe just maybe”. When I got to the house I didn’t see Esq.’s car. Good sign. Maybe Sidekick drove.

Esq. greeted me at the door and explained that he had parked around the back leaving “The Queen’s” spot for Kitty. He welcomed me into the house. He had candles lit and music blaring. Just a side note, one of Kitty’s Raw Vegan friends informed me that candles are toxic. These were over powering as was the top 40 music. Kitty is not one to complain but the music had to go. Esq. turned the music down and Kitty encouraged him to come upstairs right away to get away from the candle fumes.

Kitty has to admit that this time around went much better than the first time with Esq. which was awkward. Although his personality can be a bit grating, Esq. has a really nice cock.

Kitty let Esq. take charge this time which was a welcome change although Kitty had been texting Esq. for the past few days EXACTLY what Kitty wanted. Really what Kitty wanted was to suck Sidekick’s cock while Esq. fucked me from behind but in the end Sidekick was just not there.

Esq. had mentioned that he had never done reverse cowgirl or “cowboy” as he said. OMG! I know RIGHT?!?! See, when Kitty hears things like this from a 50+ man I feel as though it is Kitty’s responsibility to give these men what their wives clearly have not!

So, yes, Kitty rode Esq.’s super nice cock both cowgirl and reverse cowgirl. Esq. threw a little doggie in there and for our second round Esq. went old school and fucked Kitty missionary.

We lay in bed chatting and Kitty let Esq. bring up the subject of Sidekick. “You will never have direct contact with him just so you know. Any and all contact will be through me,” Esq. informed Kitty.

This kind of sucked because Kitty and Bestie Bill were hoping Kitty could play with Sidekick alone as well as alongside Esq.

Esq. asked, “Do you think you would enjoy sucking his cock while I fuck you from behind?” Luckily the room had become dark at that point because the smile on Kitty’s face could not be stifled. In an effort to seem nonchalant Kitty said, “Sure, that sounds like a lot of fun. But don’t you think I should have some alone time with him first? I mean this is the first time he’s done anything like this and to start out with a threesome? It could potentially disastrous. Shouldn’t Kitty make sure Sidekick and I have the same great chemistry that you and I have?” Kitty can be super sly when I want to be.

Esq. replied, “Sure, I’ll watch. I’d like that.”

And so, even though Kitty’s threesome was postponed, it is not completely out of the question.

Kitty's First Threesome

I know…RIGHT?!?!?!?!?! Kitty was SO excited yesterday!! And Kitty’s blogging bestie Bill texted that he fell off his chair he was so excited for Kitty!!

Kitty has so much to catch you all up on but let’s start with the threesome which is tentatively scheduled for this Thursday.

Kitty hasn’t heard from Esq. in several weeks since our play date. In light of the fact that Kitty found Esq. personality annoying I just let it go. In addition Esq. is totally paranoid about texting and emailing anything naughty and that is pretty much the opposite of Kitty. I mean JEEZ-US! The guy is not running for office anytime soon so WTF?! And Kitty sure as hell isn’t going to get him into trouble.

So on our last play date after we both came Kitty and Esq. lay in bed chit chatting for a bit. Kitty asked Esq. how he got involved with Ashley Madison. Like Kitty, one of Esq.’s besties recommended he get on. Esq.’s bestie “Sidekick” is also super DUPER paranoid. He’s basically living vicariously through Esq. and in his case I can sort of understand. He works for a high security agency and can’t take any chances with any of the fucknut women on AM.

So Esq. and I lay talking a little about Sidekick and as off color as my vanilla friends may take this, Kitty suggested giving Kitty’s info to Sidekick. Esq. agreed that it wouldn’t be such a bad idea. His logic was that we would most likely be sleeping with other people and that at least he trusts his bestie. Umm….OKAY!!!

So weeks have gone by and Kitty has gotten the occasional cryptic text from Esq. about the weather and coming down to his vacation home etc. Kitty replied with snarky texts but really Kitty enjoys the occasional, “I can’t stop thinking about fucking you again,” text.

Well yesterday of all days Esq. began texting Kitty at work. He seemed a little more responsive. He asked what my week looked like and we settled on a tentative night for a play date. During our back and forth Kitty boldly asked, “What’s up with Sidekick?”

Esq., replied, “I was going to ask if he’s available and invite him along for a drink if that’s okay.”

Ummm WWWHHHHAAAATTTT?!?!?!?!?!?! Kitty knew there would be no drinking so was this Esq.’s way of introducing the threesome???

It took several texts from Kitty, “Is this a threesome you are talking about?” because Kitty wanted to be absolutely clear…I mean ABSOLUTELY!!

Kitty requested some pictures and forwarded them to my blogging bestie for confirmation that Sidekick is absolutely a cutie and when Esq. confirmed that yes in fact he and Sidekick had tossed the idea of a threesome around and would I be game Kitty said, “YES!”

Thankfully Esq.’s texting loosened up a little after that. He had to go into a meeting and once again dodged the naughty texting that Kitty so craved so Kitty texted a few scenarios for Esq. about how the threesome might work.

First, Kitty suggested playing with Sidekick one on one since Sidekick is a virgin as far as straying from his wife. Kitty thought that might put Sidekick at ease and then maybe Esq. could join in. Chances are there will be someone fucking Kitty from behind while Kitty sucks the other’s cock and then maybe they might switch. Kitty’s bestie Bill recommended the “Double Penetration” which Kitty is not opposed to but not sure if I can make that happen our first time. It seems a little ambitious but none the less if these guys can pull it off, Kitty is game. Bestie Bill also recommended Kitty get on my knees sucking Sidekick’s cock while holding Esq.’s in my hand and going back and forth. That is completely doable to Kitty.

Kitty asked Esq. what made him think Kitty would be up for that. Kitty must have an air about me or something but Esq. said we discussed it briefly in bed and although Kitty doesn’t remember, I was at one point hoping that Esq. would bring Sidekick along one day for a threesome play date.

Now keep in mind friends, this is still tentative. Last text from Esq. he couldn’t get a hold of Sidekick since he was traveling but the prospect of this threesome in the near future is as Bill says, “nothing cures a broken heart like a good old fashioned threesome.”

Kitty’s Melancholy Week Continues

Each passing day that I don’t hear from the Cowboy proves his rejection of Kitty eminent. It’s rainy and gross here today.

Kitty has been getting texts from Freddie…remember “Fast Freddie”? Well he disappeared for about six weeks. Nothing happened that Kitty could remember to prompt Freddie being angry with Kitty but never the less he disappeared. Since Kitty didn’t much care for Freddie’s ways I simply let him go…until he started texting Kitty.

Kitty has not encouraged Freddie at all nor WILL I but I did want to investigate a little theory that I had about WHY Freddie suddenly disappeared. Kitty had a hunch that Freddie went looking for something better…younger…thinner…prettier.

So last night while Kitty lay in bed feeling sorry for myself over Cowboy’s rejection I texted Freddie.

Kitty: “Have you been on any good dates lately?”

Freddie: “No. I haven’t been intimate with anyone since you. And that’s the truth. And that was July? August?”

Now how stupid is he to make a remark like that…so in other words he doesn’t REMEMBER?!?!?! WTF?!?!

Kitty: “lol August. Last text you sent me was Labor Day. I texted you a few weeks later and never heard back until the other day. By the way being intimate is not the same as a date.”

Freddie: “yes. POF They were just not for me. Two lied and one cheated on me after I expressed my feelings for her. They were all nuts.”

Now between you and me how can he possibly have feelings for this woman after a few weeks and then be stupid enough to admit it to Kitty after texting how much he misses me. WTF?!

Freddie: “One that I took out just didn’t click. I guess she forgot what she had already told me then on the date told me something different. Second one said she wanted a relationship then after 3 dates said she needed ‘me time’ and time with her son. Third one went on a few dates with me, said she’d be happy to be my girlfriend, then I caught her at the bar with another guy after she told me she was sick and going to bed that night.”

Sounds like Freddie got what he deserved if you ask Kitty.

Kitty: “Sounds like you’ve been getting out and about the past few weeks.”

Freddie: “Yes, but it’s a waste of time honestly. And a waste of emotion.”

Kitty: “Well I’m sorry but I waited and waited. I thought you were busy with work. You were dating other women.”

Freddie: “I’m sorry too. But I thought you weren’t really happy with me. Honest.”

Kitty: “You had someone kind, and funny and patient right in front of you and you thought you could do better. If you thought that you should have said something. I don’t play those games. I told you that and I meant it. Everything would have been fine.”

Freddie: “My mistake”

YA THINK?!?!?!?!?

Kitty: “Apology accepted. I hope you learn for next time. Although the chances of finding another woman like me around here are slim to none. LOL”

Freddie: “I understand. I realize that now. But keep me in mind if you find yourself single again. Best wishes to you. Goodnight Kitty.”

Kitty: “I’m not sure I could trust you Fred. I’d always wonder when you’d disappear again.”

Freddie: “I understand.”

The sad thing is I really don’t think he DOES understand.

The Cowboy

It’s a chilly fall morning here in Kitty’s part of town. Kitty has been wanting to write but life keeps getting in the way. Kitty is a little melancholy today but no worries. It will pass. It never fails. Just when things seem hopeless Kitty gets an email or a text or I run into a friend at the market. Kitty doesn’t let life get me down.

Kitty’s Ashley Madison life always seems so much simpler than my vanilla life. My Ashley Madison friends accept me for who I am. My blogging friends accept me for who I am. Who am I?

Well…Kitty is just about the same person in my vanilla life that I am in my Ashley Madison life only with clothes on. Kitty is bright, funny, loving and yes…somewhat over the amount that I would like to weigh. In my Ashley Madison life this plays little or no part but in Kitty’s vanilla life, it apparently means everything.

Kitty has been working with a client lately. He is a cowboy. Typically if Kitty is working with you, things are not too good in your life. But Kitty is also very compassionate and likes to see the good in people. The Cowboy is single and he is a man of simple means and for whatever reason Kitty is attracted to him. I’m attracted to his vulnerability I suppose. I’m attracted to the simplicity of his life…with the exception of the fact that the mother of his child is in and out of his house. Kitty can picture a vanilla life with the Cowboy while still enjoying my independence and perhaps a little Ashley Madison fun as well.

Nevertheless when Kitty wants something or someone, I go for it. So the Cowboy very casually invited Kitty and the kids to his farm for a visit. Kitty jumped right on it but I suppose his invitation was more out of politeness for Kitty’s overzealous interest in his business and his life in general.

We had planned for this past Sunday and although Kitty was dressed more for a date than a farm visit I mentally prepared to make the trek to the farm in good faith. A few hours before we were supposed to head over the Cowboy called and had to cancel. His reason was more than legitimate and although Kitty tried to convince myself that things on a farm happen and we can’t be touring in the midst of this business, the bottom line is the Cowboy just isn’t interested in Kitty.

When he called to explain why he had to cancel Kitty said, “It’s really no problem. Maybe sometime we can get a drink or something.”

The Cowboy answered, “well here’s the thing…I don’t drink.” Kitty wasn’t put off so much by the fact that the Cowboy doesn’t drink as much as the fact that he didn’t say, “But we can grab lunch or something if you want”.

Since I was in a public place when he called I texted the Cowboy later and said, “Sorry, couldn’t talk when you called. I meant to say if you want to get together another time to let me know. It doesn’t have to be for an alcoholic drink and it doesn’t have to be for a date. Just thought you might want to talk/vent…”

The Cowboy replied, “Sounds good. Thanks”.

While trying to over analyze the Cowboy’s short but clear message that he was just not interested Kitty was texting a blogging friend who said, “He could have had the blowjob of his life at a minimum.”

Kitty, “Looks are deceiving. Most single guys can’t see past my dowdy, somewhat overweight exterior and my soccer mom minivan. More often they will go for the hot chick who is using them for their money.”

Blog friend, “Well, I look at it differently. I guess because I am married the discreet soccer mom milf who knows how to shut her mouth is a huge turn on. By the time we are 50 we are all imperfect as far as our bodies but the flip side is we know how to be erotic. That is why I avoid younger and visibly hot women…I see drama…I see home wrecker…I see danger.”

And so…we will see. Kitty doesn’t hold much hope for the Cowboy but you just never know. Keep good thoughts for Kitty this week a playmate in my vanilla life is just what the doctor ordered and let’s face it…who DOESN’T want to fuck a Cowboy at least once in their life.