My Side Job Leads to Fun

My excursion into the escort world started after 15 years of no sex with my wife. Through the years I got to know some of these ladies very well. One even told me about a customer she had where the husband would come and watch his wife have sex with her. He had another fantasy where he would watch his wife have sex with her and a man. She had me come to be the man. I even got paid. But that's another story for later. Another lady by the name of Mindy had pictures of her on the internet that didn't do her justice. I took some pictures of her with my camera and did a little photo editing to them and sent them to her. She loved them. Thus was the start of a new side business for me, taking pictures of escorts for their advertising.

This is a story about one of my most fun photo shoots. I had already done 2 photo shoots for Hilary. The Holidays were coming up and she wanted photos showing the Holiday spirit for some specials she was going to run. Plus she was going to have Mindy come so I could do photos of her and them together for their special doubles sessions.

I told her I would only charge them $150 a piece since I didn't have to set up at two locations. We set photo shoot for Thursday at Hilary's apartment at 2:00 p.m.

I arrived at Hilary's right on time with all my camera gear. I walked into her apartment and Hilary greeted me with a hug and a kiss.

Mindy was just taking off her jacket as she arrived a few minutes before me. Mindy hung up her jacket and came over and gave me a hug and a kiss then reached down and gently squeezed my cock and said, "How have you been? I haven't seen this guy in awhile."

I told her, "I have been fine. I like to see a variety of women. Plus it gives me a chance to promote my business to other ladies."

The 3 of us sat down and had a glass of wine to discuss what we were going to do for photos. Each had 3 outfits they would be using and Hilary staged several areas of her apartment for spots to take photos. After they were done with their separate photos they would do photos of them together.

Hilary was already dressed so she went first while Mindy changed. Let me tell you about Hilary. Hilary is a very nice lady with a bit of a head case. Hilary was on an HBO documentary about escorts so she thought of herself as a movie star. She also prices herself like one at $500 per hour. Hilary has long light brown hair down to her shoulder blades. Light green eyes. She has a cute face. She has a slender 5'4" body with the most perfect boobs I have ever seen. It is hard to believe that she actually had a breast reduction as they are a natural DD. Her areolas were the size of a 50 cent piece and they were neither dark nor light in color. To me her areolas were my fantasy type.

Mindy started off wearing a short green dress. To which later I photo shopped it to a black dress in a few pictures. We did photos of her sitting at a high top sipping wine, standing by the fireplace and sitting on the couch. While on the couch she hiked up her skirt a bit so you could see her neatly trimmed pussy.

Now it was Mindy's turn. Mindy you would never guess it but she is a grandma! She had her first child at 16 and her daughter had a child also at 16. Mindy is 38, 4 years younger than Hilary. Mindy's best features are her face and hair. Her face is like a model with a roman type nose that accents her features. She has sparkly blue eyes that naturally smile. Her smile is gorgeous as she has straight white teeth framed by her perfect lips. Her hair is blonde and very wavy. It hangs down just below the middle of her back. The rest of her body is very nice too. She stands 5'6" on a medium frame. She has a cute tight little ass. Her boobs are a D cup with slightly smaller areolas than Hilary's.

Mindy comes out in a black tight V neck sweater, black leather skirt and black high heel boots. No need or photo shopping this outfit, I love it. We do the same shots as I did with Mindy with the exception of the pussy tease on the couch. On the couch I have her lean over and I get some nice cleavage shots with her face looking up at me.

Hilary comes out and it's her turn. Hilary is wearing a black bra, black lace panties, black garter and socks and black stiletto shoes. To top it off she wore a pearl necklace.

I tell her, "Wow you look great."

Hilary replied, "Thank you. You like my pearl necklace? Maybe later you can give me one!"

I laugh and say, "Maybe I will."

I am taking photos from every angle I can think of with Hilary. I have her slowly remove her bra and got about 20 shots of just that. With her bra off I can feel a stirring in my cock. I try to concentrate on what I am doing and not let my other head distract me. We finish up with the lingerie and partial nudity shots.

Mindy comes in dress in the same outfit but in white. I go through the same routine with her as I did with Hilary. Except Mindy wants a bunch of close ups of her ass. Mindy keeps backing up closer and closer to me.

I tell her, "Mindy, I have a zoom on my lens. You don't need to get right on top of me."

She says, "I want to make sure you get a close up."

I tell her, "If you fart, I am going to be pissed!"

We both laugh and finish up our shots. We take a break and enjoy a glass of wine together. It seems weird I am sitting with two gorgeous woman, both are topless and I am having a casual conversation with them. They started to talk about different customers they have had and compared notes on them. One of them was a guy who had a 10 inch cock. Both of them said they hated to fuck him because he would thrust hard and deep right away and it hurt. But he always tipped them well.

Mindy looked at me and said, "Now you, if I remember, you have a big cock and know how to use it."

I smiled and said, "Thank you."

Hilary chirped in and asked, "Are you a grower or a shower?"

I answered, "What do you mean by that?"

Hilary said, "Grower is you are small but grow really big. A shower is your big but when it gets hard it isn't much bigger."

I replied, "I guess I am a grower."

Hilary laughed and said, "I remember you were good size, but never saw you limp. I also like how you can stay hard after you cum."

With that I suggested we finish up our last photo session of them together.

They each dressed in white lingerie. They put on Santa hats for some shots for their Christmas special they were going to offer. Two women for one hour $650. I had them slowly undress each other as I took shot after shot. I had them sitting on the couch playing with each other's boobs.

We then moved to the bedroom. They eventually got totally naked in the bed. I stood on a chair at the foot of the bed and shot down on them. My cock was getting hard and straining against my pants wanting to get out as I took pictures of them making out.

Then Hilary stopped and said, "I think we have enough photos. I have a customer in 3 hours and I have to get ready."

I put my camera equipment away then said, "I still need to get paid."

Hilary opened her purse and handed me $90 and said, "This is all I have right now."

Mindy said, "I forgot to stop at the ATM and get money."

I was not happy until Hilary said, "How about we give you a free double session."

Being that my balls were aching for relief and they were my two favorite escorts I agreed.

We moved into the bedroom and enjoyed a 3 way kiss. Mindy moved down and took off my pants while Hilary took off my shirt.

Then the two ladies got undressed and enjoyed another 3 way kiss. They worked their kisses down my body until they got to hard cock. They both kissed and licked my cock. Mindy slowly started to take my cock into her mouth a little at a time. Hilary started to lick and suck on my balls. While the worked my cock and balls over I ran my fingers through both of their long thick hair.

Mindy was doing an excellent blow job and I could tell it wouldn't be long before I was going to cum. Then to my surprise Hilary started to tongue my ass. This sent me into a whole new state of excitement that I didn't want to end. I started to pump my hips slightly into Mindy's mouth. Each stroke pulling out I could feel Hilary's tongue go a little deeper up my ass. Hilary had a good grip on my balls and they were aching to be released of their cum. I fought the urge to cum. I wanted to enjoy it a little longer.

Then Hilary replaced her tongue with a finger. Her fingered gently worked its way in and started to massage my prostate. While doing this she returned to sucking both of my balls into her mouth. This was pleasure overload for me and I could no longer hold back.

I filled Mindy's mouth with my hot cum. She couldn't take all of it as some ran from her mouth and dripped down on her beautiful breast. Hilary slid her finger out of my ass and then licked my cum off from Mindy's chest.

The ladies started to kiss each other then got up and moved to the bed. Mindy laid down on the bed and Hilary started to kiss her way down her body until she got to her hot wet pussy. I didn't need any recovery time as the site of them two gorgeous ladies naked together got me hard right away.

From prior experience at Hilary's place I knew she kept her condoms in the nightstand next to the bed. I went over and took out condom and slid it onto my eager hard cock. Hilary's fine round ass was in the air as she ate Mindy's pussy. I got on my knees and tasted Hilary's pussy. It was already wet and tasted sweat. I got up and slowly slid the tip of my cock into her pussy. She pushed back taking me deeper. A couple more pushes and I was deep inside her.

I reached forward and cupped Hilary's heavy breasts and rolled her nipples between my fingers. They were hard and loving the attention. I slowly pumped my cock in and out of her wet pussy. I was ready to get down to serious fucking. I took a hold of her hips and started to fuck her faster and harder. The view I had was what dreams are made of. Hilary eating Mindy's pussy and her hands were massaging her boobs. Mindy's eyes were closed and her hands were holding Hilary's head tight against her pussy. I looked at my thick cock pounding Hilary's pussy going in and out. Hilary was moaning and so was Mindy. I could tell Mindy and Hilary were both about to have their orgasm and I knew I wasn't far behind. It was like a slow chain reaction. Mindy came first. About 5 seconds later Hilary came. Then 10 seconds later I filled my condom while inside Hilary.

Hilary and I collapsed onto the bed. I was between the two beautiful women. We laid there and kissed for a little bit. Then Hilary went down and started to suck my cock to bring it back to life, while I kissed Mindy and worked my way down to her hard nipples.

Mindy moaned as I sucked her nipple into my mouth and gently nibbled on them. My hand found her wet pussy and she was ready for my now hard cock.

Mindy said, "Time for me fuck that big cock."

With that she got up and inserted a female condom. Hilary pulled her mouth off my cock and Mindy lowered her hot pussy slowly onto my cock. This was the first time I had experienced a female condom and I couldn't even tell it was there.

Hilary said, "I need to have some fun."

Hilary moved up and startled my head then lowered her pussy to my waiting mouth. Mindy was riding my cock and Hilary was getting her pussy eaten from me. I reached up to cup Hilary's breast and found Mindy's hand were already there. Together we massaged Hilary's perfect breasts.

It seemed like I was in that position for a long time. But I didn't mind. Mindy started to rub her clit as she rode me. I suddenly felt Hilary gushing on my face as she came. Shortly after that Mindy came. She climbed off my cock and in about 10 strokes with her hand I shot hot jets of cum that landed on Mindy's face and Hilary's back.

Hilary rolled off my face then looked at the clock and said, "Shit I have to get ready, I have a customer coming in an hour."

She got up and headed to the bathroom to shower.

Mindy said, "Now it's just you and me. Do you have another one in you?"

I told her, "Maybe, we can always try."

I was still half hard and Mindy took my cock into her mouth and began a slow teasing blow job. It worked I was hard in a short time.

We went into missionary position. I arched my back up and put the weight on my arms so I could see her DD tits bounce each time I thrust in her. I pumped her like that for a good 10 minutes but was not feeling like I was even close to cumming. I lifted her legs over my shoulders and that felt a lot better as I was able to go deeper and it felt tighter. It didn't take long after changing positions and Mindy came.

I kept on going. I could feel it start to build deep in my balls.

About this time Hilary came out of the bathroom and said, "Jesus, you two still going at it? Hurry up, I need to change the sheets."

I looked at Hilary and said, "I am so close, I just can't get there."

With that Mindy reached down and wrapped her thumb and middle finger around the base of my cock. This gave me the extra pressure I needed.

Mindy said, "Oh god, oh god, oh god I am going to cum again. Cum with me."

That is all I needed and I felt 3 hot jets fill her pussy. I sat there inside her for a bit as she tightened her pussy muscles and drain the rest out of me. I let her legs fall off my shoulders and I pulled out. Mindy pulled her female condom and I could see my cum inside it.

Hilary said, "Get dressed and get out of here. He will be here soon."

We didn't get a chance to clean up. We got dressed and I grabbed my gear and Mindy took her suitcase full of the outfits she posed in and we headed out the door.

We hadn't gone more than 10 feet from the door when we met Hilary's customer coming down the hall. Mindy giggled and whispered to me, I guess he will be wondering why she seems so tired!"