Gigolo to gay in one night.

[Tanbbottom]

Moderator's Note: This story contains brief mentions of straight/bi sexual content. If that will distress you, please do not read it. 

What started as me at 19 being hit on and paid by matronly women for sexual favors changed in one encounter when I was 23. 

This particular life changing night everything seemed as usual. An older well healed woman entered the bar. She sent me a drink. We engage in mutual flirting. She offered me a crisp new $500 bill, asks if I was okay with kink and we head off together to her place. 

Turned out she was from out of town, staying at a high end hotel. 

It's not 'til we get to her room that I start to realize I've drifted into something I hadn't counted on. 

This is what she'd meant when she asked if I was into kink. Maybe I should have asked more questions. The room was set up as a sex dungeon. Fuck bench, sling, St. Andrews Cross, straps, whips and a tonne of stuff I had never heard of or seen before. 

She ordered me to strip and stand facing the cross. My arms were lifted and strapped to the cross. My legs were spread and strapped to the floor. 

I thought this strange but decided to be a good sport. 

That's when the bathroom door opened and a naked 40 year old 6 ' 5" muscular man entered the room. He was already sporting an 11" erection. 

She introduced me to her husband and informed me she really liked to watch him have a good time. In case I hadn't figured it out I was to be his good time. 

I considered protesting but realized in my current position I didn't have much bargaining power. 

He started by nibbling at my ear and whispering things he liked about my body. Blonde hairy bubble butt, broad tanned shoulders, well developed hairy chest, six pack and substantial cock.

I was interested to notice that as he began to kiss and lick my neck my dick began to respond. I love sex so why not just go with the flow? Besides, it wasn't like I had a choice. 

Every cell in my body tingled as he kissed his way down my spine. When his tongue entered my hole I was so hard I feared I might blow my wad. 

I began to think, 'this might not be so bad after all. '

He worked my hole for ten minutes before he stood and moved in to hug my back. His fingers traced my chest and played with my nipples. I could feel his erect cock between my legs and brushing against my taint. 

His wife brought him a bottle of lube and he began working lube into my ass. One finger, two fingers, quitting at four penetrating my hole. 

His fingers were removed and I noticed she was lining up his naked cock.

Sex with matrons beyond menopause had never required condoms. I'd grown quite fond of the freedom. But this was a different matter. 

I was resigned to the fact I wasn't leaving this dungeon without taking my first dick up the ass; but, I sure as hell would do everything I could to protect my health. 

I stayed calm and asked nicely that he use a condom. She slipped a $500 bill into my hand and asked; "Will this do?"

Staying calm I responded; "No. He needs a condom to enter my sacred space. "

She smiled at me and placed another $500 into my hand. 

When I shook my head he placed a ball muzzle in my mouth strapping it around my head. 

She said "Final offer " and placed two more bills of the same value in my other hand. A total of $2500 for one nights work and the fact I really didn't have a choice. I moaned my acceptance and nodded my approval. 

She handed her husband poppers and he fed them to me one nostril at a time. My head began to swim and my ass began to relax to the pressure from his cock head. 

More poppers for both of us and his mushroom head popped inside my ass ring. 

At this very moment warm lips wrapped around my cock. A sweet young twink had arrived without me noticing. 

She introduced me to her newest sex toy. "I peg him on a regular basis. Tonight he's being served raw meat. Yours. "

He gave a great blowjob which helped distract me somewhat from the pole sliding deeper and deeper into me. 

Her husband finally bottomed out and the fucking began. 

I had never felt so full and the sensation I could split in two. Despite the discomfort I was not hating this. In fact I was very turned on by the [banned word] act of a raw cock in my ass and a guys mouth working my straight cock. 

It was then that I realized I was meeting each of "hubbies" in strokes with an equal and opposite push back of my ass. I was not just getting fucked bareback, I was actively participating. 

"I bought you the man, breed him. " crooned the matron. 

The twink pulled his mouth off my cock and managed to fit between me and the cross. My cock went into his eager ass hole. In this flash I was in my first of many raw fuck trains. 

Within a couple of minutes the husband was growling; "Fuuuuuuccck  ... yoouuuu  .... straight gigilo  .... pumping my load deep in your fuckin guts. Take  ... my ... fuckin ... load .... Arrrr!"

I didn't feel the cum, but I did feel the ongoing contractions. I was very pleased with myself for bringing him to such a massive release.

He pulled out far too soon for my liking. His massive tool was replaced almost instantly by the twinks 5 incher. 

Within four or five strokes I could feel the blast of every shot painting my guts and mixing with "Hubby's".

I was then released from all bondage and led to the fuck bench. The twink's ass was waiting for me to finish what we had started. 

As I entered him and started to fuck something entered my rear portal. The patron was pegging me with a strap on.

She did so for about five minutes until her husband was back in me on the verge of another massive climax. 

As he blasted in me I loaded the twink with one of the most explosive orgasms of my life. 

We three men went to the shower where Hubby bred the twink as I pumped a load into Hubby. 

The second door from the bath led to a luxurious room with a massive hot tub and three king size beds. 

The matron watched and instructed each of her men to breed me yet again. 

When room service arrived with two carts brimming with food she insisted that the two bell hops drop trou and dump two more fresh loads into my ass. 

6 loads from four guys all in one night for my virgin straight ass. My sex escort career switched gender lanes in one life changing experience. 

 

 

[Rondog]

Great story. Can't wait to see where it goes. 

[pozpopperpig]

Great start!

[Twochipigs]

Hot story, but if you're going for authenticity make the cash payments five $100 bills.  Starting in 1969, the Treasury and Federal Reserve Bank began removing $500 and $1000 bills from circulation.  Although they're still legal tender, most existing today belong to collectors.

Also, sorry to be a spelling nitpicker, but the proper spelling of the word in the title is "Gigolo."

[drscorpio]

3 hours ago, Twochipigs said:

Hot story, but if you're going for authenticity make the cash payments five $100 bills.  Starting in 1969, the Treasury and Federal Reserve Bank began removing $500 and $1000 bills from circulation.  Although they're still legal tender, most existing today belong to collectors.

Also, sorry to be a spelling nitpicker, but the proper spelling of the word in the title is "Gigolo."

Moderator's Note: Fixed the spelling.