bigliva2020's Blog

Shortly after that amazing first session with Miss K, I was invited back for our first photo shoot. She wanted promo photos for her website and I was flattered to be asked back.

When I arrived she was in a big sweatshirt and baggy pants. A bit disappointed but undaunted, I asked what she was hoping for but she brushed me off with a glass of wine and questions about Erica. How did we meet, how often does she work and how much does Erica's pay site make. Katherine was very straight forward about her intent. She wanted me to duplicate all that for her. When I told her that it's alot of work and commitment, she smiled and told me that I'd be well taken care of.

When I told her the pay site would need 3 photosets a week plus at least one 5 minute x-rated video, her response was let's get started.

I followed her into her bedroom, the largest room in the house with a very wide walk in closet jammed with clothes, lingerie, leather whips, handcuffs, a dildo shelf and more.

She picked out 5 outfits and we went to work with various poses on her bed. The first photo set ended with her in a see through bra and panty outfit. The last few shots of were of her pulling the panties aside expose a huge clit. Fat and at least an inch long. The next two shoots were of Katherine playing with a dildo. In her mouth, pussy and butthole. She was not shy.

At this point I was aroused. Couldn't help having to adjust my hard on in my pants. She knew and I think she enjoyed my discomfort.

For the fourth set, Katherine took us to her adjoining bathroom. she got naked and lay down in the tub. Spreading her legs she began pissing.
Her spray was strong. Reaching up a good foot above her body then splashing down all over her tummy and tits. Miss Katherine had breast implants making her boobs very erect and round but also hard. Her pee bounced off of her tits like a hard rain on pavement. Made for a great photo.

For her video Katherine stood up in the tub and rubbed her clitty fast and hard then using a dildo rammed herself even faster and harder. Very soon after she began squirting. at this point I was leaning into the tub for a close up and I sure got it. All that pussy juice blasted the lens on my camera. While it made for a great ending for the video I was quite nervous about it ruining my camera.

Once she was done squirting. She simply asked if that was enough to start the website to which I replied definitely. That's the hottest thing I've ever shot. You'll do very well.

Good she said turning on the shower to clean off which I took as a hint to leave but Mistress Katherine had other ideas. While her rain forest shower head gently poured over her naked athletic body she asked me if I thought the bra and panty outfit was sexy. Well of course I said, definitely.
"Good, then go put it on and show me".

I couldn't believe what I was hearing but didn't hesitate. Back into the bedroom, I stripped, pulled on the white lace panties, snapped on the see through bra and returned to the shower for Mistress Katherine's critique.

My erect dick was showing in the too tight panties and the bra kinda hung down since I don't have boobs but she was complimentary then told me to join her in the shower. The warm stream of the shower quickly soaked the panties making my hard on very easy to see.

Mistress began rubbing my cock then knelt down onto her knees removed my erection and took it all in her mouth. The water splattered against her naked back and trickled down my chest. The sensation of the warm water, the moist mouth my cock was in felt so wonderful.

My eyes were closed but all my other senses were in overdrive. Mistress Katherine's oral skills were amazing. I began thrusting myself deeper into her mouth. She responded by matching my rhythms. Both her hands had grabbed my panty covered ass cheeks and were squeezing my ass quite hard.

I came. I had to hold onto her hair to keep my balance. She didn't flinch. She deep throating my exploding cock and kept sucking every last drop of cum out of me.

Her laugh is loud and infectious. As she stood up wiping a drop of my cum from her lips she said that should keep you happy til next week.

"Throw those undies in the hamper, dry off and join me in the kitchen." With that she wrapped a towel around herself. Slowly. Making sure I had a long final look at her toned body. Her boobs standing straight out, a tight flat tummy, perfectly waxxed pussy mound and her thighs were enormous. Perfectly contoured like a bodybuilder. The towel closed the show and she left me dripping wet in her bra and panty set.

Mr. Thicke invited me along because he wanted to have a dick in his mouth while His Dom pegged him.
That vision definitely peeked my curiosity.

We arrived at a well groomed property at the end of street in an equally well groomed neighborhood.

We were greeted at the door by this 5 foot 5 shapely woman with a tight tank top form fitting jeans and blazing red and blonde streaked hair.
Mistress Katherine greeted both of us with a warm hug and fulsome laugh as Mr. Thick introduced me.

We were invited to sit down, served a coffee and seemed genuinely interested in my photography and web building hobby. She even knew Erica and asked if she and I could talk more about that later.

Mistress Katherine had Mr. Thicke give details of his fantasy. I was impressed at how excited she was about each detail of my bud's request. She offered up detailed questions and ever suggestions like did both of us want to told to suck off her strap on? Finally she brought out the strap on harness and asked Mr Thicke which size of cock attachment he thought would be best to be fucked with.

What I remember the most about this first encounter with Mistress Katherine was how into the scene she was. Wearing surgical gloves she buried two fingers into his butt hole to lub him up. Her voice changed to a more stern but amazed tone as she said her little faggot ass boy was going to take all of her cock and like it. She directed Mr. Thicke at every step making him beg for her to pump the strap on deeper into his ass. She'd spank his butt cheek if he didn't answer fast enough. Punished him with a strong stroke if he let my cock fall out of his mouth. She also used a whip on his back. All this torture only turned Mr. Thicke on more.

He got his wish to have my dick in his mouth as his ass was being pounded. Most amazing of all was that he shot a load without touching himself.

Once the sex of the session ended she removed the strap on and cradled Mr. Thick between her large enhanced breasts. She even invited me to jerk myself. Her voice was intoxicating. Her words of encouragement had me cumming in no time. We all rested comfortably in her bed. Naked. Making small talk for several more minutes.

As we were leaving she asked for my number and I got a text from her on the drive back.

"I need new pictures for my ads and a website. Interested?" I smiled all the way back to work.

Backpage got banned. Leolist prevailed. I got a new job. Most free time shriveled up.

For 3 long years, I was on my best behavior. Well almost. I'd kept in touch with Mr. Thicke, a client of Erica's.
Originally we met during one of Erica's parties but he needed computer help so we started own connection. Whenever he needed help I'd invite him over to my place. The man was always horny so after the work or lesson on VPN's or other security issues were done, he'd show off pictures or videos of his latest conquest. This usually got him hard. Knowing I was bi cause Erica and I had already sucked him off a few times, he was quite happy to just pop his dick out and start stroking right in front of me. Sometimes I'd join him, other times I'd get between his legs and enjoy his hard on while he watched porn on his laptop. It got to the point where I knew how to get him off within about 10 minutes. sometimes soon.

He came by his nickname honestly. Uncut, 10 inches with a bend in his shaft which was at least 4 inches thick. The best I could do was make half of his cock down my throat. No matter. He loved how I would rub his balls and just lick the tip of his head then cover only the head in mouth and facefuck him. His load wasn't a big one but the first shot always slammed against the back of my throat giving me quite a surprised. I loved that.

If he was in a hurry he suggested we stand facing each other so he could grab both his and my cock and jerk off. We got pretty good at coming almost at the same time.

He also liked watching me jerk off and cum all over his dick so he could use my cum as lube for himself.

For most of this period in my life Mr Thicke was my only extra curricular activity.

Then he invited me to join him and his Mistress. A dominatrix that would change my life.

After Erica help open the door to my bisexuality, cock was my primary desire. Thanks to Craigslist and now grndr I found myself giving and receiving bj's probably twice a week.

Still I was also attracted to women. Specifically boobs. Big Boobs. Really really big boobs which often came attached to large women.
These experiences were fewer and farther between.

Luckily the era of Backpage was just beginning. Through Erica I started a side business. Creating ads, then subscription websites and setting up cam sites. First for her and then her escort friends. My reward with Erica was essentially a barter arrangement. She kept the money and I got sex. Lots and a wide variety of sex with her, with her girlfriends and even some boyfriends. Within 6 months she was making on average $2,000 a month from the sites I'd created for her. She & I would create content once a week. Usually a few photo sets of her in different outfits, doing different things to herself or my cock. Plus 2 or 3 videos. I'd slip over at lunch time or later when her two daughters would be in school.

She shared me with a few of escort friends so within a year I was working with no less than 5 different girls. One in particular was a BBW named Meena. Erica, Meena and I would have 3somes to create content for their sites. I was in heaven. Meena loved to give specific instructions about how to eat her pussy which both Erica and I loved doing. The bigger thrill for me was titty fucking Meena. Her boobs were enormous. Even today I dream of her 42E boobs devouring my dick.

Erica had the idea of inviting clients to help make content so a few times I became the fluffer. How she found these well hung guys was always a mystery. Some white college students, a few older white guys but she had her favorite black stud. A tall basketball player type with 10 inches of uncut hard cock. She made at least 20 videos with him. He did a few with Meena to but wasn't attracted to her so either Erica or I or both of us would have to suck him off before he could pound that huge glorious mound of Meena's.

My job involved alot of out of town travel so quite often I'd have one of the ladies join me and we'd do their content in hotel rooms, deserted buildings, at the beach and even locals houses in exchange fore service.

If memory serves, I was having some form of sex 4 times a week, every week. When I wasn't making content for one of the girls then I was online finding cock to suck or experiment with. This lasted over two years. It was the craziest and best time of my life.

First dick in my mouth was about 8 years ago. Before that I'd visit escorts maybe once a month because sex with my wife along with the relationship had rerailed.

Erica became a steady or actually I became one of her regulars. She was different, I guess everyone says that, but I felt it. Before sex she would ask what I'd like to try. Since I lacked imagination at the time, It was difficult to get me excited with any of her ideas. she had perky little breasts with huge nipples, an hour glass figure with a cute ass and her pussy was always changing. Weird but I was always turned on by her bush when she had one, or her landstrip, or even when she was waxed. Erica was always changing it up and always inviting me to go down on her. Whatever idea she came up with seemed so natural, fun and she was definitely non judgmental.

My lessons started with various positions then one afternoon, at her place she stripped me down, asked me to get something from her back porch then locked me out. There I was for her neighbors to see. Only lasted maybe 5 minutes but when she let me in, she asked if it turned me on. It did. soon after we were having sex in public.

Next we would go to swingers parties as a couple. The first few times I got to watch her play with other men's wives. It always started that way then we men were given permission to join in. It was hot watching Erica having sex with other men. It was hot watching her with women. Hell everything about it was hot. On on particular night Erica spent a long time chatting, kissing and hugging this one chubby wife and they kept glancing at me while talking. We went to there room for drinks then the ladies sat between her husband and went to work on his very long cock. The chubby little wife then invited me to join her in sucking off her very well hung guy. Erica nodded encouragement and helped me lick up and down his shaft. She showed me how to keep my lips over my teeth and slowly take in the head. I loved it.

She knew I loved it. That first time, she encouraged me to take as much as I can. There was alot of gagging which if I recall turned on this guy and his wife. Erica finished him off while I serviced the wife but all I could think about and talk about later was how exciting having dick down my throat was.

She made a note and began setting me up with more opportunities to explore my feminine side.

Soon she had me over to suck off clients, then gay friends of her's. It didn't take long for me to learn that she really got off watching guys sucking dick.
Usually she would want me to eat her pussy right after which was also fun. I guess that's about the time I admitted that I was bisexual.

But I couldn't keep that up, Erica was expensive. Do I discovered Craigslist first and then Grndr.