Kat's First Ashley Madison Encounter - Chicago Guy

It was a Sunday afternoon and I was working in my office at home. Correction:  I was procrastinating in my office at home. I had seen one of those faux Ashley Madison commercials on TV (brilliant marketing ploy, by the way) and I decided I had the time to take a look. I had also recently decided that it was time to start prowling again.  It had been about 7 years since my last fling (yes, that's right, seven...long....years) and I was ready.  I was more than ready. 

I signed up quickly using one of my rarely-used web email addresses and a fake name. It was simple. So far, so good.  I set up a profile.  All those check boxes were annoying, so I wrote a few lines, not trying to impress anyone at all - just trying to get through the stupid profile creation process without a blank profile.

Then I started browsing. 20 miles from home.  50 miles from home. Wow!  So many choices! Within 20 minutes, I was getting messages.  Lots of messages.  I started answering them while still browsing. Within an hour, I had a few men I was chatting with and I stopped answering the messages for awhile.

Chicago Guy was one of the first messages I received that day.  He was in town for a couple of weeks on business and he said this was his first time trolling on AM, and that he had never had an affair before. My heart sank a little because I was really looking for someone local for a longer term thing, but he was a nice guy, so we continued to chat.

He was in town for a couple of weeks, but I use the term "in town" very loosely.  Apparently, he wasn't familiar with northern California when he was browsing in my area.  He was actually 90 minutes away. Oh well, another strike against anything ever happening with this guy.

There was flirting.  There was naughty conversation. There were exchanged photos (hmmm...not bad). Then came the requests to meet that day.

Not gonna happen, I thought.  First, it was Sunday.  I never just take off on a Sunday.  Hubby would never buy it.  And this guy was 90 minutes away.  No way.

So I told him, sure, as long as he was willing to drive an hour my way.  I'd drive 30 minutes in his direction, and we could meet at a hotel near a shopping destination that I'd use as my alibi. I knew the answer would be no.  What guy would drive an hour for sex?

To my surprise, he said yes and asked when he should leave.

Holy maloney!  It was now or never.  I told him to leave right then.  I went to hubby and made my case for an escape for a few hours. Then I cleaned up a bit and left.

I got to the room first and checked in and waited.  To say I was nervous would have been an understatement. As I sat there in the quiet thinking, all sorts of terrible thoughts occurred to me. What am I doing?  He seemed too eager.  He must be an axe murderer. What if he doesn't like me? (Why I was concerned that an axe murderer like me, I'll never know.) What if he doesn't look at all like his photo? What if we have no rapport in person and the sex sucks?  How long do I have to stay if I change my mind?

My terror thoughts were interrupted by a knock at the door. I walked over to the door and looked through the peephole. Relief.  Not only did he look like his photo, but he was quite handsome. He was tall (6'2") and muscular with a shaved head and a goatee. He wore jeans and a Chicago Bears jersey, and he looked perfectly comfortable.  If this was his first time, why wasn't he nervous like me?

I opened the door and we smiled at each other. I stepped aside so he could enter and we uttered some quick greetings as he walked in.

"Kat? Hi," he said.

"Chicago Guy?" I replied.

(By the way, I'm not using an initial for his name like I usually do here because, well, I don't remember his name.  I know.  What a slut, huh?")

Unexpectedly, he pulled me close and kissed me as soon as the door closed. We stood there kissing for what seemed like the longest time until the heat started to build and clothes started to come off. He kept his mouth on mine constantly so I couldn't ask him the critically important question I had in mind.  I thought I'd ask it as I pulled his jersey off over his head, but then I got a look at his chest and decided that this was not a time for talking.

As soon as our clothes were off, he turned me around, put a hand on the back of my neck and bent me over the bed. I threw my hands down in front of me to catch my fall as he pushed my legs apart with one of his knees and pulled my hips up, indicating that he wanted to me to stand, bent over at the waist.

I felt him step back to look.  I felt so exposed, bent over the bed nude while he looked at me, inspected me. I heard him unwrap a condom and put it on.  Thank God.  We hadn't even talked about that. His hands started to caress by back, then my ass, my thighs.  He slid his hand between my legs and very slowly and gently pressed a finger inside me. I shuddered a bit.  He gasped and whispered, "So wet....very nice..."

He pulled out his hand and reached around, putting his fingers in my mouth. I sucked on them obediently, cleaning off every drop as I felt him lean against me. I felt him positioning his cock to enter me, but he was so tall and I was so short....I went up onto my tippy toes.  The extra couple of inches was all he needed, and he slid into me with one deep stroke.

That first experience of new cock is amazing, but this was particularly incredible because it had been 7 years since I had been with anyone besides my husband.  I started to push back against him, but I couldn't because he grabbed my hips and lifted me up slightly so I couldn't get my footing. He fucked me deeply and hard for about 30 seconds and then he came.

I thought, That's it? Surely we're not done.

I laid down on the bed while he disposed of condom #1.  We chatted a bit.  Then I remembered!  I had to ask the question!

"White Sox or Cubs?"

He laughed. He tried to kiss me, but I pushed him away.

"Answer the question first.  Then I'll decide if there's more."

He got serious, looked into my eyes, and said, "Cubs."

"Good answer, " I purred, and I kissed him.

He kissed his way down my neck, lingered for awhile sucking on my nipples, then down my belly. He shifted his body, repositioning himself between my legs, which I had spread wide open for him at that point. I felt his tongue exploring me, until he found my clit. He sucked on it for about 10 seconds, just long enough for me to let a hungry moan escape.

Then he pulled his head up, looked at me, and said, "Wait.  I have a question now."

"Seriously?" I panted.  "Can't it wait?"

"Nope," he said rather matter-of-factly as he slid a couple of fingers inside me and started rubbing my clit with his thumb.

"What is it?"

He teased, "Maybe I shouldn't ask it yet, but I can't let you cum until you answer and unless I get the right answer.  Do you want me to ask you the question now, Kat?"

By now, his finger had found my g-spot and his thumb had my clit and I was rocking my hips, pressing against his hand.

"Yes, ask the question," I moaned.

He stopped moving his hand.  "Maybe not."

"Please!  Please ask the question..."

He started moving his hand again.  I remember thinking, he'd better ask that damned question soon or I won't be able to think clearly enough to answer.

Then he asked the one question that I could answer under any conditions.

"Giants or Dodgers?"

"Giants!" I yelled.  His hand stopped.  For the first time ever, the thought actually crossed my mind that Dodgers might have been the correct answer.

Naaaaahhhhh.

He replaced his thumb with his tongue, finger fucking me while he gave me the best (ok, the only) tongue lashing my pussy had had in seven years.

As soon as I started to shake, he reached up and put his forearm across my belly, holding me still. I was amazed how that forced all of the energy and focus inside me as I came. It was more of an explosion than an orgasm. He kept working it all the way to the end, letting me enjoy every last jolt and shudder.

He gently slid his fingers out of me and climbed back up next to me, kissing me right away, making me taste myself.  He rubbed his wet hand on one of my breasts; then he leaned over me and started kissing and licking it it clean.

After about a minute, he found my mouth again (I was just laying there, dumbfounded and satisfied at that point) and kissed me deeply. His kiss wandered to my neck, then my ear, and he whispered, "Good answer."

We both laughed. We talked some more. Condom #2 and condom #3 were well used (maybe I'll share those details in another post).

Then we looked at the clock and it was time for me to go. We talked about meeting again as we got dressed, but we both finally admitted that it wasn't going to happen.  I had a busy week ahead.  He was flying home on Friday.

We kissed each other goodbye and walked out together. We waved goodbye as we each walked to our cars. That was the last time I saw him.

I drove away thinking, this AM thing may actually work out for me. It turns out that it did because the very next time I logged on, I met J (The Best Sex of My Life).