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Missed Opportunites

"I thought I'd missed opportunites with her, not this time..."

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I originally met Marti at a company I used to work for.  She was older than me, but I wasn’t sure how much.  I’m guessing ten years or so, as I was in my early thirties.

She was thin and tall with the heels she always wore.  The thing that caught my eye about her, was the way she sashayed when she walked.  She had a very nice figure and an absolute killer ass. 

I believe she was married as she sported a wedding ring.  I got to talking to her occasionally at some Friday after-work happy hours.  Her husband never seemed to be around, so one night I asked her, and she told me he had been working out of state and wasn’t around too much.

We became pretty close over the next few months.  One time she picked me up at the car dealership and gave me a ride to work.  I noticed when she drove, she kicked off her right high-heel shoe.

I don’t know why, but I just thought that was such a turn-on.

When she dropped me off, I asked her if I could buy her a drink sometime for giving me a ride.  She said that would be great.

The closer we got, the more time we spent having drinks.  Sometimes we even had drinks at my house, but I never tried to hit on her because she was married and because I didn’t think she’d ever have any interest in someone like me.

One Friday, I went over to her office and asked if she had any plans that night.  She said no, so I asked if she wanted to grab something to eat.

She said, “Don’t you have a girlfriend, or should I say, girl friends?”

“No, I don’t have much luck in that arena.  My last girlfriend and I broke up about six months ago, so I’ve been dealing with that.”

“Well, you’re a catch, so you should be out there playing the field.”

“Perhaps, I’m just not looking for anything serious right now.  I just like hanging out with you.  I feel that I can just be myself.”

“I like that in you.  Why don’t we grab something to eat after work?”

We went to the local watering hole after work and had a couple of drinks and appetizers.

Then I said, “Well, I’m getting a little sauced, I think I’m going to head home.”

“Pretty early for a Friday, don’t you think?”

“Well yeah, I guess I’m just a lightweight.”

“Why don’t I grab a bottle, and let’s go to your place for a bit if you want to?”

I was floored and didn’t know what to say.

Since I was feeling pretty good, I said, “You’re not going to try and take advantage of me, are you?”

“Mmmm, maybe…”

With that, I picked up the tab, and we headed for my place.  All I could think driving home was what was going to happen once we got there.

Once inside, I heard the doorbell, and it was Marti.  I opened the door, let her in, and took her coat.

She was wearing tight slacks, and kind of a see-through white blouse and black pumps.

She handed me the bottle and I went into the kitchen to open it.  As I was doing that, I felt her get behind me and put her arms around me.

“Everything OK?”

“Ye, I’m just watching you open that bottle.”

I got it open and poured us each a glass.

We walked back into the living room and sat closely on the couch and start to sip our wine.

It was quiet for a while, and I was trying to figure out what was going to happen next.

Then she said, “Boy, you sure are quiet!  Is anything wrong?”

I replied, “Well, I’m sitting on my couch, with a really hot lady, who’s married, so I will say, I am somewhat confused!”

“I understand.  Let’s just say, I really like you, and even though I’m married, our marriage is very dull and unexciting.  I’ve tried to make it better, but it seems like he’s really not interested.”

“Wow, why the hell wouldn’t he be interested?”

“I don’t know.  Maybe he has a girlfriend where he is, who knows?  The question is, are you interested?”

“Ahh, ye.”

“Tell me, why you’re interested, and I want you to be totally honest.”

“Totally honest?

“Mmm hmm.  Tell me what you like about me.”

“Well, I think you’re a great person, you’re sweet, and have a great sense of humor.”

“No dipshit, I mean physically.”

“Well, the first time I saw you, I said to myself, that’s the nicest ass I’ve ever seen.”

“Oh, so you like my ass?

“Yes, is that bad?”

“No, that’s good.”

“What do you like about me?”

“I think you’re very hot, and you have a nice ass too!”

 With that, we finished up our wine, and I got up to get us a refill.

Marti said, “Are you trying to get me drunk?”

“No, I’m trying to get me drunk!”

“Why’s that?”

As I handed her the glass and sat back down, I said, “I’ll be honest, I’m pretty nervous right now.”

“Awe, don’t be nervous, I don’t bite.  I bet if you kissed me, you wouldn’t be nervous anymore!”

So, I grabbed our glasses and put them on the coffee table.  I leaned into her and we started kissing.

It got pretty heavy, pretty quick, and I started getting a massive hard-on, and it was really hard to hide.

We hastily enjoyed making out, sucking on each other’s tongues and probing into each other’s mouths.  She was really good with her mouth and I just couldn’t wait to see what she could do with my cock in it.

I started to unbutton her blouse and she helped me get it off.  Then I got her bra off in a matter of seconds.  I then climbed on her and straddled her lap as she helped me remove my shirt.

I then got off of her and laid her down on the couch as I removed the rest of my clothes.  Then I unbuttoned her slacks and slid them off.  As I slid them down her thighs, I noticed she had nylons on.  I removed her shoes to get her slacks off but wanted to leave her stockings on, as I loved the feel of them.  Then I put her shoes back on.  She just laid there watching me do all this with no facial expression whatsoever.

In my mind, I knew I had missed opportunities with her, but not tonight.

I climbed onto Marti’s chest grabbed her arms, and placed my cock by her mouth.

Looking at me, she started licking and kissing it gently.

Growing harder with anticipation, I grabbed my cock, and as she opened her mouth for me, I guided it in.

As she closed down on it, I started to push further into her mouth, then pulling back some, then pushing back it.

This went on for a while, and as she adjusted to me, I eventually got most of my seven inches into her.

I started face fucking her, and she seemed to be enjoying it.

I wasn’t going to be able to last long.

I pulled out and said, “Sorry, I’m not going to last long, where do you want me to come?”

“Wherever you want to baby!”

Her calling me baby, made me all the harder. I put it back in her mouth, and we got back to our previous rhythm. I was going a little harder and trying to go as deep as I could without causing her any discomfort.

When I got ready to blow my load, I just pulled back a bit, and we made eye contact. Waiting on the explosion, she kept sucking on me and using her tongue. I finally blew what seemed like a gallon into her mouth, and I just kept spasming.

Not a drop was lost.

After I pulled out, she pulled me to her to kiss. We made out with her mouth still filled with cum.  I had never done that before, but I will say, that it was a bit of a turn-on.  I thought it was the least I could do for her letting me get off in her mouth like that!

“Marti, I’m sorry, I came so soon, I’m out of practice.”

“That’s fine, I’m out of practice too.  I hope I made you feel good.”

“Oh, it was very good!”

“Let’s go into your bedroom.”

We got up and headed for the bedroom. When we got there, she pulled the sheets back and motioned for me to get in first.

Then she said, “I want you to lay on your stomach and just relax.”

I had no idea what was to happen next. Then I felt her climb onto me.  She started kissing my back and worked her way down to my ass. She then tried to move my legs apart to expose my ass, so I helped her ease the task. Was this really happening?  Was she going to do what I thought she was going to do?

Next, I felt her kissing and licking her way to my ass hole. She spread my ass cheeks apart and started kissing and licking my ass hole. I had never had this done to me before, and apparently, she had been down this road before. Marti knew what she was doing.  She licked and kissed and probed my ass for about ten minutes before she tried to fuck into my ass with her tongue.

I moved around to expose myself to make the job for her as easy as I could. I eventually ended up on my knees, holding my opened exposed ass to her tongue.

She tongue fucked me for a while, I’d say until it probably got tiresome for her. Just as I thought she was done, I felt her start to probe me with her finger. She worked a finger or two in my ass and finger fucked me for a while as she grabbed onto my cock and tried to jack me off.

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Occasionally, she maneuvered herself down and sucked on me for a while. She never got me to cum again.  She knew what she was doing.  She was saving it for later.

When Marti was done treating me to anal pleasure, she came up to me and whispered in my ear, “Did you like that?”

“Oh Marti, that was great, I’ve never had that done to me before.”

“Would you like to do that to me?  You can if you want to!”

I didn’t need her to ask twice.

I swiftly positioned her on her stomach in the middle of the bed, and for a minute, I just looked at her.

All the times I thought about being with her, and it was actually happening.  Not only was I amazed we were having sex, but for her to be so into anal and offering her ass to me, was just unbelievable.

I climbed on top of her, kissed her on the cheek then started to work my way South. I gently kissed my way down her back, taking my time, and savoring every second. Once I got to her ass, I sensually caressed and kissed her cheeks before working my way to Ground Zero.

I grabbed both of her incredible ass cheeks and spread them apart from one another exposing her opening. I gently placed my first kiss on her, then more, as I let some saliva fall out of my mouth onto her. Then I started licking around her asshole, until finally gently probing into it softly for the first time. I heard Marti sigh as I continued to work my tongue into her.

I took my time, savoring every second of pleasuring her ass.  How long I had fantasized about doing this?  How long I fantasized about having my face in her ass, and here I was. I was going to take my time, like this was the only opportunity I would ever have with her.

I would say I had feasted on her ass for at least half an hour, doing everything I could with my mouth.

How bad I wanted to fuck her ass now.  I was so hard.

I placed a finger in my mouth and got it as wet as I could and placed it at the entrance of her ass. Gently circling, I started to push in, and to my surprise, I started to enter her pretty easily.

Marti sighed as I gently pushed in.  Once fully inserted, I playfully circled, then pulled back on it only to re-enter her.  Once she seemed comfortable, I added some more saliva to my fingers and went into her with two.  Once I got them into her, Marti was sighing and moaning a little differently than before.  Maybe showing signs of some discomfort now.  I just took my time with her.

Once she got used to my two fingers, I thought I should try to get a third in, even if it was just through her ass opening.

I gently pushed in with three, and she at one point tried to pull away.

“Are you OK?” I asked.

“Yes baby, just go slow for a bit longer.”

I did as she requested and finally was able to get three fingers into her opening. At one point I just left them there motionless, letter her relax with her asshole open to me.

I moved up to kiss her and gently kissed her on her cheek. She never opened her eyes, she just lay there relaxed.

I wasn’t sure what to do next. Then she looked at me, “Are you going to take my ass now?”

“Yes, but only if you want me to.  Do you want it?”

“Mmm hmm.”

With that, I pulled my fingers from her and went to my drawer where I had my lube. I remembered the last time I had used this lube and fucked Dawn in her ass. It had been months. I was just hoping that I could really get Marti off without going too early. I really wanted this to be special, and so far, it was perfect.

I passionately started kissing Marti on her ass cheeks as I poured a gracious load of lube and started working it into her ass.  She seemed ready to go, and I certainly was, but I thought I’d give another load just to make it easier. It’s not like I have a huge cock or anything, but I just didn’t want to hurt her or make it hard. In the back of my mind, I could only imagine how hard and deep I might be able to fuck this ass just awaiting me.

Without saying a word, I poured a good amount of lube into the palm of my hand and greased my pole up nicely. It was time. I grabbed my cock, and push my head into her ass, and it just plopped right in. I slowly pushed it in another couple of inches, just so it wouldn’t pop out.

I slid my hand down the base of my rock-hard cock, and pushed in until my hand met her ass. She offered no resistance.

I just held still for a minute and felt her warm ass walls adjust to me, and I could periodically feel her tighten her ass around my cock and then release. It felt like she was now trying to use her ass muscles to pull me in.

After a few moments of feeling her asshole and settling down, because I didn’t want to blow my load before I actually got to fuck her ass, I continued to push in.

I was able to push all the way into her hot little ass with surprising ease.

Either she was used to frequent anal sex, or the lube was doing an incredible job.

Once I was balls deep into her, I fell onto her back and wrapped both arms around and under her.

I pulled her tightly to my body as I continued to push into her.

Once I got every millimeter into her, I gently pulled back some and started to pump her warm brown hole.

I continued pumping her with short gentle strokes.

As I became used to the feel, and as she got used to me, I continued and worked out further.

Eventually, I was able to pull out almost to the head of my cock, and push all the way back in.

Marti seemed to be loving this.

Surprisingly, I was able to not blow my load, which I could not wait to do, as I knew it would be incredible.

I grabbed onto Marti’s breasts as I fucked her ass harder now.

Kissing her on the side of her neck, she reached around and placed her hand on the side of my head holding me to her.

Then she said, “Oh John, fuck me, baby.”

“Like this?”, as I picked up my pace.

“Mmm hmm.  Harder if you like.”

Now that was good news to hear.

I started pumping her ass with long hard strokes and really pushing in when I was balls deep.

As I continued, I picked up the pace, and after a few minutes, was fucking her ass as hard and as deep as I’ve ever have done before.

I could not believe she wasn’t stopping me, as I thought I was hurting her.

So, I whispered to her, ”Are you OK?”

“Yes, please don’t stop.”
I knew I was moments away and told her that I was gonna cum.

“Fill my ass, John, fill it, baby!”

I then exploded with a load, and my cock just kept pumping like never before.

After my cock stopped throbbing, I just collapsed onto her with my cock still inside.

It felt so good as my hard-on expired.

We rested for a bit, and I was thinking of all the times I had thought about doing what just actually happened.

It had felt so good, I wanted to do it again if I was able to, and if she’d let me.

After a few more minutes, I started kissing her on the back of the neck, working my way down to her ass.

She just laid there, as if she was sleeping.

I kissed my way down to her ass, and spread her ass cheeks apart, exposing her cum filled hole.

My cum was draining out of her.

It was such a turn on seeing that.

I took my fingers and started fondling her asshole, wading through the puddle of cum.

She seemed to be enjoying it as I started to work a finger or two back it.

Marti started moaning with pleasure after a bit of this, and I was starting to get hard again.

The site was such a turn-on.

After most of my cum had dripped out, I gently kissed her right on her asshole and started to fuck it again with my tongue.

It was really starting to drive her crazy, and it was a huge turn-on for me.

I then climbed up onto her, and we started kissing sharing some of the cum I had licked out of her ass.

Then without saying anything, I grabbed my once again hard cock, and slid it back into her ass.

I fucked her again for a while, and I didn’t come as fast as the first time.

Marti was enjoying every stroke, hard and fast, or soft and gentle.

Sometimes, I just pushed into her as far as I could, and would just hold still.

Then I could feel Marti, squeeze my cock with her asshole muscles.

I eventually fucked her ass and came again.

We fell asleep and awoke many times through the night.

I really don’t how many times I fucked and came in her ass.

But I do remember, finally holding onto her and falling asleep with my hard cock still inside her.

The next morning, I woke up and made coffee.

She got up, came over to me, and gave me a big hug.

“John, that was absolutely unbelievable last night.”

“I know, I’ve never done anything like that.  It was something!”

“Yes, it was!  Why don’t you take a shower with me?”

We went into the shower, and once again, my cock found its’ way into her ass.

I had released another load into her ass, and she just couldn’t seem to get enough.

I was sore for a couple of days after that, and Marti and I continued to hook up and have a lot of sex and anal adventures.

I knew she’d be open to trying some of my anal fantasies with me.

I wondered if she’d fuck me?

I guess I’d have to find out…

Published 
Written by Jackson007
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