Michelle's Past - The Gentlemen

Tom sat down in front of his computer and loaded his e-mail. His wife Michelle had left on a solo vacation and he was left to his own devices, which is never good and why Michelle always made sure he had emptied himself into her before she left. Then she would send him notes or videos throughout the trip, just to keep him on edge. A year ago, she sent him a picture of her deepthroating one of the guys in the hotel.

Seeing his gorgeous, busty wife sucking a massive cock with a look of pure bliss across her face got him so fucking hard that he nearly burst right there, with no stimulation. He did restrain himself until he could get home.

But this time, it looks like she was doing something else, he read her e-mail titled "My First Older Man" with his cock in hand.

Dear Tom,

I know that you're a horny little man right now and that's ok. Don't worry! I'll be fine. I really appreciate the new swim suits and lingerie that you packed for me. You'll see the pictures when I get home, unless one of my "conquests" really wants to keep them!

But I know you want something from me, so this is what I'm doing. I want to tell you a story about the first time I fucked an older guy.

I was 23, and just out of college. I was working in some small investment company and no, he wasn't one of the owners. It was women owned and kinda shitty, but that's a different story.

After I had been there for a month, I really, really, really wanted some sexy new underwear. So one day after work, I went to the mall and walked into whatever lingerie store there was. I found a few items that I really liked. Thongs, gstrings, one pair of boyshorts that were very lacy and oddly sexy in the weirdest way possible. I also found matching bras for all of them.

When I took them to the counter, my card was declined. Apparently I had forgotten to pay the bill and I was so embarrassed. But as I was sheepishly putting my card away, a voice behind me said "I'll pay for that Miss."

I turned around to find the source of the voice and saw a really handsome man. In my mind's eye I see him as giant, but he was probably of slightly taller than average height. I will never forget his icy blue eyes and salt and pepper hair, curly, but slicked back and tamed with something. He smiled a wonderful smile as he told me he'd pay for my items.

I graciously thanked him outside the store and he smiled rather wolfishly and said the way I could repay him was to show up at his home in two days, wearing my sexiest dress and the gstring with its matching bra underneath.

I clearly agreed as two days later I arrived at his house overlooking the lake. You know the one, it's not too far from where we live. It was one of those glass and steel modern homes that were popular.

I was wearing the underwear he told me to wear and I had on the only dress I owned that I looked the best in. It was dark purple, asymmetrically cut near my calves, with spaghetti straps and low cut, which showed of my ample cleavage. I had whatever heels looked the best, I honestly don't remember.

I entered and he greeted me at the door and complimented me how I looked. He escorted me down the hallway to the dining room and his private chef was waiting. He had prepared a five course meal for us, with wine pairings and I was too much in a daze to really remember it all.

After dinner, I remember we were laughing and he suggested we move to the patio outside. As I got to the door frame, he said over his shoulder "Drop the dress" in a very commanding voice.

I was stunned, but did as he asked and entered the cool night air in just my heels and underwear. I caught a glimpse of my ass in the windows and I knew I looked good.

He had me sit next to him and he draped an arm over my shoulder and gently fondled my breasts. He then said "You know, you're gorgeous. But I think it's time you paid me back."

I was a bit young and naive, so he reminded me with this. "Get on your knees and suck my cock young lady".

That voice made me tremble with arousal and I did exactly as he asked. His cock was average sized, with a small bush but he was clean and smelled divine. He tasted even better.

I sucked him on his patio, overlooking the lake, my ass exposed to whomever could see. He had some privacy, but I still get wet thinking about his neighbors watching me suck him.

He leaked precum rather quickly, quicker than I expected and eventually he had me stop. "Take off your bra and slide those panties to the side" was his next order. I once again did as I was asked. "Now ride me" was up.

I slid my wet pussy, god damn was I wet down his saliva slicked shaft and slowly rode him. My chest was in his face and he moaned into my cleavage. I don't remember if he said anything or just moaned, but I rode him for quite a while. Eventually he came and it was really powerful. I was shuddering the whole time and my pussy milked every drop of him out. It was like I was on autopilot.

He let out one more sigh and spurt. He told me to get off of him and lick him clean, which I did, and I cleaned him thoroughly, lapping up all of our combined cum with my tongue off his cock and balls, bush, even his pants.

He stood up and got dress and told me to leave my dress and bra for him. He gave me his dress shirt and told me to keep my panties. Then he sent me home, filled to the brim.

When I got home, I masturbated with a dildo I had had since college at least three more times.

So now dear Tom, I tell you this story so you can masturbate to something old, but new. Don't worry dear! I'm sure as you read this, I'll be getting fucked by someone, probably wearing the lingerie you packed for me. Perhaps I'll share that story when I get home. Until then, be a good boy and cum to this story as many times as you need to!

Your Loving Wife,

Michelle

Tom loved everything about his wife and he looked down. His hand was covered in cum. He was so engrossed in his wife's words, he hadn't paid attention. Fuck he married such a delicious little slut.

He cleaned himself off and went to bed, naked, knowing that Michelle was getting a good fucking tonight and tomorrow, he'd cum to this story again and again and again, until she came home with a new one.