A Courtesan Becomes My Confidant

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August, 2020

Here is my preamble to this story and my comments as I get near the end of the series.

Generally, readers seem to enjoy my stories and I am grateful for the views, votes and comments.

Actually, some of the comments I didn’t appreciate and I deleted those as soon as I read them.

I started writing these stories in the summer of 2017 to see if I could write fiction after writing non-fiction for many years.

It turns out that I can actually make stuff up and put words on paper (or the screen) and, surprise! —– I am pretty good at it.

Let me make it clear I am not saying I am great.

But my stories have been interesting for me to create and write and for people to read.

More than a few people have asked me where they can find a directory of my stories so let me state that you can find the entire list under my biography tab.

But here is the complete list and if I ever have time to go back through all my stories I will be sure and include this directory on every story:

1: I Hire Monica the Maid

2: Monica’s First Day as My Maid

3: Monica the Maid’s Three Hole Day

4: I Partner with Linda, a Salon Owner

5: I Massage Monica the Maid

6: Hot and Sexy Business Opportunities

7. I Become a Therapeutic Instructor

8: The Affair Continues in Las Vegas

9: I Rub an Asian MILF the Right Way

10: Going Where No Man Has Gone Before

11: Cumming Where No Man Has Cum Before

12: That Was The Weekend That Was

13: I’m Rewarded for a Job Well Done

14: Fun in Las Vegas with my MILFs

15: That Was The Week That Was

16: I take My MILF Lisa to Mexico

17: I’m Ambushed by a Very Hot MILF!

18: The CFO Gets Her Assets Worked Over

19: In Hot Pursuit of a Very Hot MILF

20: The Second Time is Twice as Nice

21: Roadblocks Pursuing the Hot MILF

22: Nirvana! My Hot MILF Likes Pussy!

23: Las Vegas Swimsuit Photo Shoot

24: Three Models in a Vegas Hotel Room

25: I Enjoy Two Threesomes in Two Days

26: I Take a Short Trip to Mexico

27: I Travel from Mexico to Las Vegas

28: I Celebrate Turning 35 in Las Vegas

29: One Wild Night in Beverly Hills

30: My 35th Birthday Weekend Continues

31: My 35th BD Party Ends with a Bang!

32: I Deal with Her Ex and My In-Laws

33: I Reflect on an Interesting Year!

34: An Interesting Evening in Las Vegas

35: A MILF Neighbor Shows Her Gratitude

36: A MILF Neighbor Comes Clean

37: A MILF Neighbor Plays All Night

38: I Play with Three MILFs on Vacation

39: My Wife Gives Me a Hall Pass!

40: The Perks of Flying First Class

41: I Join The Mile High Club!

42: Why I Eat a Lot of Pussy

43: I Hit a Grand Slam in Seattle!

44: Have You Ever Changed a Diaper?

45: I Learn about the Hot To Trot Club!

46: Send Lawyers, Guns and Money!

47: I’m Running on Empty Ch. 01

48: I’m Running on Empty Ch. 02

49: I’m Running on Empty Ch. 03

50: I’m Running on Empty Ch. 04

51: I’m Running on Empty Ch. 05

52: I’m Running on Empty Ch. 06

53: Men Want to be Me, Women Want Me

54: Separated, I Play Hard in MILF City

55: I Seduce a MILF at The Adult Pool

56: I Rub My New Banker the Right Way

57: The GILF Gets It in the End

58: I Convert Two Lipstick Lesbians

59: Her Boardroom is our Bedroom!

60: Justice is Delivered

61: How I Spent My Summer Vacation

62: Three MILFs Make My Morning

63: An Afternoon to Remember

64: It’s An Offer I Can’t Refuse

65: A Divorced Asian Submits Her List

66: A Divorced Asian Earns Her Spanking

67: A Divorced Asian Closes The Deal

68: About That Offer I Couldn’t Refuse


I want those that read this story that my goal when I started writing in July, 2017 was to get a rating of 4.00 or higher on every story.

For those of you that remember getting a report card, that means a B. Or B minus.

Only one story has not hit that standard but I am okay with that.

So, having rambled on a bit, this is story 69.

It takes place right after story 67: “A Divorced Asian Closes The Deal.”

Let me suggest you first read, or re-read, that story first before diving into this one.

This is an adult sex story, all fiction, make believe and made up.


I spent the next three weeks in Sedona, Arizona.

When I emerged I was a changed man.

A better man.

I was the house guest of Marie, my massage therapist from “Bliss” in Scottsdale.

Marie was a mature Asian. I had no idea what her age was, or anything about her background but she had come recommended by someone I trusted so I went into her place for a massage.

In the beginning she was all business, but it didn’t take long for her inner beauty to surface.

And she had a great body to match.

But …

My visit to Marie’s healing and massage salon was truly blissful until, benevolently drugged with relaxants and bursa escort tenderly tied down, on my belly with my legs spread, I had a large rubber dildo stuffed up my ass as I got butt-fucked by Caroline … the hot Asian divorcee.

Caroline really got off, meaning she had large, loud and earthshaking orgasms as she took me deep, shallow, fast and slow with that expensive, custom made strap on.

I thought for sure I was going to be split in two.

I can’t tell you how many times she said in the midst of her thrusting, how tight I was.

And that it was her job to loosen up my tight ass.

My very tight ass.

“Do you need more lube?” she’d tease me and while I always choked out “YES!” she rationed it out … she dripped it out as if it was gold.

The truth was there was no shortage of lube she was just being a bitch and wanted me to suffer.

Well, I did.

Getting fucked up your butt hurts a lot.

Especially the first time.

Lube makes it better, easier, but there is still a lot of hurt (I mean HURT!!!!!!!!) and it gets worse when the penetrating object probes deeper and deeper and deeper.

It was painful, humiliating and what made it worse was how my body reacted to the penetration or should I say invasion, and her non-stop pushing and thrusting; each time she pulled out (but not completely) and I breathed a sigh of relief she’d cackle and push her hips forward and that rubber cock would go even deeper into my tight bat cave.

I don’t mind saying I shed a tear or two and my knuckles were white from gripping the sheet on the massage table.

When I took Caroline’s virgin rosebud I did it lovingly, slowly, lots of anal play, a massage to relax her, penetrating her with lots of lube and starting slowly with a single finger and when Caroline got more comfortable, I applied more lube and introduced a second finger, gradually opening her up.

I was in no hurry, we’d been fucking for a few days and she knew it (me fucking her ass) was going to happen at some point.

She’d actually agreed to it.

But I was a slow and very gentle lover.

I might not have always had a lot of patience in my business dealings but when it came to taking a woman’s anal cherry, you couldn’t find a nicer guy.

It took me a long time to get my rock hard cock all the way inside of Caroline’s back passage and I stopped several times when I could sense her tense up.

I would pull out a bit, give her time to adjust, add some more lube and gently, oh so gently, push in a bit further into territory that a penis had never visited before.

She had a very, very tight ass and God how I loved fucking it and I know she actually enjoyed it, or so she said.

Caroline didn’t give me the same kind of experience.

She was on a real power trip.

I was her boy-toy.

Her man meat.

Her fuck hole.

What was beyond humiliation — was that even possible? — were there stages of humiliation? —– was that I started to react, respond, to her thrusting.

Not at first, when I was trying to squeeze my cheeks together to stop her penetration; her poking, for that I got some very hard slaps and spanks on the most tender part of my ass as punishment.

“Open up baby and let me in” Caroline teased me, “I bought your virgin ass and it’s time to take possession.”

At one point she sort of pulled me up a bit by the hips so she could fuck me deeper, faster, harder.

I protested against her wanting to push that monster to the hilt but she was merciless.

She was not going to be denied.

When she finally stopped pushing in all the way and started fucking me, in and out, slowly at first, it was almost natural to start to fuck her back, despite the pain, despite the fullness of my bowels and despite the humiliation of a 36 year old man being “taken” by a woman.

Caroline quickly noticed my new found, what will I call it … enthusiasm (!) and teased me that I was a maybe I was a switch hitter because apparently I liked it in the ass.

“Good boy Jack, take it deep for your lover” Caroline cooed at me.

I moaned.

“This is only the first time Jack … from now on your ass is mine. I’m going to fuck it all the time.”

A groan surfaced from my throat in protest but I kept my mouth shut.

When she stopped thrusting but I continued to rock on the rubber and I heard a smile in her voice when she shared that “Jack likes it when I’m fucking his tight ass, doesn’t he?”

I moaned again, in pain this time as she grabbed my hips and plowed me deep, pushing every millimeter of that rubber baseball bat into me.

She ground into me, saying “Take it Jack, that’s a good boy” Caroline whispered to me as I really started to respond to her thrusts.

All this ass fucking and teasing got me hard as a rock.

I don’t think I had ever been as hard or as big as when Caroline was fucking my ass that afternoon.

Man, it wasn’t very long at all long since Marie had me dropping a load into her throat and here I was.

Ready to cum again.

How about a reach around? My cock was large, hard and pulsating; ready for bursa escort bayan some relief.

But it wasn’t going to come from Caroline; she was in her own little world of causing me pain and getting off on her own selfish pleasure fuck.

Caroline loved to be in control.

Total control.

She was totally into domination.

But Clare, who was beneath the massage table verbally added in her two cents on my length, girth and hardness … while she was in awe of my size she was also a mean bitch and just teased my cock relentlessly with her fingers with absolutely no intention of allowing me to cum.

I loved Clare touching my hard cock and almost sobbed when she stopped just teasing me as my cock thrust into the air searching for something to rub against.

I don’t think I had ever been denied an orgasm to this extent in my entire life!

When I did drip some precum, all Clare did to help was to use her index finger and massage the white sauce into my very sensitive mushroom head, which made my urge, my need to cum that much more pronounced.

As Caroline’s fucking continued, I was soon begging to cum … Clare just laughed.

Marie didn’t say a word.

Clare made it worse for me by quietly yet sensuously teasing my tight sack with her fingers and her fingernails, knowing full well that all it was doing was manufacturing more little swimmers that had no place to go … I was soon begging Clare, bargaining with her … trying to bribe her … with money … travel on my private jet …. trips to Vegas … new clothes … jewels … all to no avail.

As for Caroline, of course the first poke, that initial penetration of that rubber cock was painful, despite the lube … then when I attempted to tighten my cheeks and then tried to expel the monster size rubber cock, Caroline gave me no mercy … being very, very gentle was not in her tool kit … she slapped my ass, hard and suggested that what I was going through was not as bad as what she experienced when I took her virgin ass just a couple days before …

Caroline pounded away … she seemed quite experienced with the strap on … surely this was not her first time because soon I could hear her breath start to quicken, her hips moved faster and she pulled on my hips so the rubber cock would truly plumb my depths and causing my belly to convulse in pain … all which she ignored on her quest to bring herself to an orgasm … time after time … good Lord this woman loved to cum …

Her condescending, sarcastic, teasing attitude that she shared with the other two ladies in the room, Marie and Clare, about how she’d been waiting to do this, this butt fucking, for months, ever since I turned her business deal down went on non-stop from the first poke to her finally collapsing on my back.

Having cum more times than I could count, when Caroline finally collapsed, her flawless nude body coated with sweat, and proceeded to hug me tight while her shuddering slowly subsided.

Once she regained her breath she sat up and slowly, very slowly, pulled the large dildo out of me.

My starfish was gaping; winking at her as it slowly closed.

My asshole felt like the entrance to the Holland Tunnel.

Open wide for business.

I could even smell my own shit as it wafted out of my no longer tight water sealed starfish.

Caroline slapped my ass a few times simply because she could and announced “That was the most money I’ve paid for a piece of ass but it was the best I’ve ever had.”

Caroline got off the massage table, bent down and kissed my cheek, something I did not expect, as in a moment of tenderness from this Asian Bitch (with a capital letter).

“Jack, now you know what it was like for me to take you the other night in my ass. The dildo I used on you is from a cast that was made of your big, beautiful cock in Las Vegas last Fall. You can thank your wife for giving me one as a gift. I was saving it up to use on your virgin ass. I’m looking forward to using it again on you.”

With that, Caroline left and headed home.

But not before taunting me and slapping, very hard, my bare bottom more than a few times and laughing at me.

Her parting words were “You’re my bitch Jack and I own your ass.”

My cheeks burned red. Both pairs.


Marie, who hadn’t said a word during the whole pegging thing, gently rubbed my ass, soothing me, and that was fine until she started in with her needles, you know, acupuncture, to help me rid my body of the pain from my sciatic nerve being out of whack. Which was the reason I went to see her in the first place. It seemed like months ago but it had only been a few hours.

I guess she figured with a throbbing starfish and a bowel that had never been an on-ramp before, only an exit, the needles would seem less painful.

She was wrong, the needles fucking hurt too.

Clare, Marie’s sister, helped me under the massage table and alternated her time and attention to my raging hard on with her lips, tongue, mouth.

She never used her fingers on me, and never lost contact with my cock once it was in her mouth.

Clare did tease escort bursa me with her fingernails, but that attention was devoted exclusively to my balls.

I didn’t last long the first time with Clare; my cock had been throbbing for relief and she passed her oral exams with me!

I came loudly and it seemed like my orgasm went on forever as I spurted gobs of my hot sticky goo into her mouth.

While I have to confess I didn’t much care for her when she was teasing me when Caroline was fucking my ass, Clare proved her worth to me with her oral finesse.

She gratefully allowed me to cum very quickly that first time as my pent up baby batter rocketed up my cock into her warm, wet mouth of hers.

And, to her credit, she did not allow me to soften; she worked her mouth, tongue, lips and throat like a Beverly Hills escort and in only a few short minutes she was sucking my timber down into her willing tight throat, coaxing a second load in no time flat.

The third time Clare had to work for it but God bless her, she stayed at it, reviving my sapling back to a redwood like no other woman I had met could.

Each time Clare gratefully swallowed my load without choking or gagging on my creamy white sauce.

After taking care of me, fully draining my balls, Clare left to go home too.

She said a few words in Japanese to Marie and once Clare left, she said “Clare loved your cock. She said it was the biggest one she’d ever played with. And she said to tell you that your cum tasted sweet. Next time she wants you to fuck her. I told her that we’d see about that.”

Which made me feel just a tiny bit better about myself.


Marie stripped down, and got me off the table and into the bath. She showered with me, cleaning every crevice I had (one of them very tenderly and softly) and then bundled me up in some pajamas and slippers and took me north to her three story Sedona home with 360 degree views of the surrounding red rocks.

I slept alone that first night and I had no idea how long I had slept or what time it was when I woke up.

Marie came into my dark bedroom with a cup of coffee wearing her birthday suit.

“How did you like getting fucked in the ass Jack?” Marie asked me with a sly smile.

No “Good morning.”

No “How did you sleep?”

No “Are you hungry?”

Just right to my ass being fucked the day before.

“It hurt like hell” I replied back, not looking at her, “It’s not something I care to have happen again.”

I looked at her and she nodded in understanding.

Then she said something that stuck with me for a long time.

“You didn’t put up much resistance Jack. In fact, you didn’t put up any resistance at all to getting butt fucked.”

I finally looked at Marie and nodded and she replied “You need a time out to get your bearings and that is why you’re here with me. I’ve been planning this little retreat for you for a long time. That ass fucking should be a wake-up call for you. Your life is pretty fucked up right now. It will get worse before it gets better.”


With those not so encouraging words, I got out of bed and used the bathroom to do my thing and then met Marie out on the rooftop patio.

I couldn’t find anything to wear (my clothes had disappeared) so I went outside naked as the day I was born.

Marie was still naked and while the sun was high, it would be moving west in an hour or so, and the air would cool the land down at the mile high altitude.

The outside fireplace was burning as we sipped our hot black gold.

“Now you know what it’s like when you take a woman’s ass for the first time” she shared.

I nodded again and then she continued with “But it sure looked to me like you got into it” and I shyly smiled at the thought of Caroline fucking me from behind while I was begging Clare to give me a hand job.

Hindsight is always 20/20, right?

“If you think you’re going to fuck me in the ass Marie, you’re on drugs.”

She laughed and said “I’m into anal sex about as much as you are right now.”

Marie took a sip and said “Oh, you’ve been getting fucked Jack, big time, and you don’t have a clue. Even the fucking Caroline gave you was signed, sealed and delivered weeks before you arrived in Scottsdale.”

“What are you talking about?” I answered, getting a little pissed.

Marie took another sip and answered with “You’re going to find out why I brought you here. But first you need to relax and get a clear head. By that I mean, no booze, food that it good for you, lots of rest and no clothes. If you’re good I will let you have your phone back. Down the road. For now you’re disconnected from the world.”

With a knowing smile, she set her coffee cup down, got up and walked over to me, knelt at my feet, pushed my legs apart and lowered her head to my soft cock.

It didn’t stay soft for very long.

God that woman could suck a dick.

It turned out that she had many more redeeming qualities but for now I was just fine with her oral skill set.


Another day passed, we did some chit chat, getting to know you stuff, nothing serious.

The truth was that we had been nude the entire time we’d been on her property. She had told me when I was first getting on the massage table in Scottsdale that “I like my men naked” and she wasn’t kidding.

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