It was Saturday, and I had a portrait photo session set up for 11am. It was supposed to be just a normal head shot session for a guy who sold real estate locally. The session would probably only last about 30 minutes, and we would shoot about five different angles and lighting scenarios with maybe a change of clothes. It was to be a straightforward, easy session and then I would edit the five images and send them to him by e-mail and I would be done for the day. Was I surprised at how much I was wrong about this shoot! It would turn out to be anything but ordinary and simple!
I had gotten to the studio about 30 minutes earlier than the appointment to make sure everything was in order. I set up the lights for a regular headshot session. Got a chair set up for him to sit in to help pose for the photos. Made sure all the camera equipment was setup and the memory cards were clean. About that time, he knocked on the door, and I let him in.
He was a thin, and not too tall person. He had short black hair that was just starting to turn gray. His shirt was light blue, button down and he had on dark blue slacks and brown shoes. He was wearing a tie that brought together the shirt and pants. He really looked like a normal real-estate agent.
“Hello,” he said. “Jack?” I nodded and let him into the studio further. “I’m Chris. I usually don’t get my picture taken, so I am a little nervous about this.”
“Don’t worry about Chris. It won’t take long and I will coach you through the whole thing. We will get about five photos with different lighting and poses, just to make sure you have what you would like to have for your business cards and website. Did you want to change clothes at any point?” I told him as he sat in the chair in front of the lights.
“Yeah, I brought another set of clothes, just in case. Glad you know what you are doing because I have no clue how to make this look good in front of the camera.”
“Great! Not a problem. You can put your extra clothes over there behind that divider and fix your hair, I think that wind got to it.” I pointed to a little spot that models use do their makeup and hair. There were some outfits and lingerie back there along with some makeup and accessories that the models can use during photo sessions. He put his clothes down on the bench in front of the vanity and then came back out and sat back in the chair. He looked a little distant when he came back to the chair, I just figured he wasn’t used to being around that much lingerie and was a little more nervous now. No big deal, a lot of the guys are like that.
“Ok, so are you ready?” I asked him as I picked up the camera and turned all the lights on that we would be using.
“Yeah, Yeah I think so!” he stammered as he regained his composure.
I walked him through about three different poses, then moved the light a little to change it up and walked through another few poses. The images looked good, he was doing a fine job and didn’t need too much coaching. The first round took about 20 minutes.
“Alright, go ahead and get changed into your other outfit and we will do some more poses and we should be about done!” I told him as I turned around and went back to my desk. I offloaded the images to the computer, as he went back to the changing area. Once the images had been copied over to the computer, I put the card back into the camera and sat on the couch waiting for him to finish up getting changed.
It was taking him a little longer than I would have thought to get changed. Usually, a guy can get changed in like a minute. It had already been ten minutes and I was beginning to wonder. I didn’t want to walk around the divider or anything, but I had to make sure he was alright.
“Hey Chris, everything alright?” I called out from the couch.
“Yeah, just getting ready.” He said.
“Alright, just checking!” I said, and I relaxed for a little bit to wait for him to finish getting changed. Still not quite sure what was going on.
I was starting to get worried again after another 15 minutes passed by and I kept checking on him. Each time he said he was fine and apologized for taking too long. I was about to be really surprised when he came out from the dressing area.
I heard him walk out to where the chair was and looked up from the camera and I was completely taken by surprise. I could not say anything, I couldn’t move. I just stared at him and looked him up and down. It took me about a full minute before I could say anything. Now it was my turn to compose myself and be professional about this and go ahead and do what the customer wants.
“Wow, Ok. Well, you definitely caught me off guard with that one. But you look amazing. Great job on the outfit, the makeup and the wig! Why don’t you twirl for me, so I can see what we are going to be working with?” I told him as I stood up and started to move the lights as they would not work for this new style of photography we were about to do.
He didn’t say anything, though he did twirl slowly for me. The outfit he had chosen was sexy as hell, it wasn’t something you would want to be out and about in. He was wearing a red bra with breast forms filling the C cups. The bra was lacy, and you could see the nipples on the forms through it. Over the bra he was wearing a translucent black top, that didn’t do much to cover anything. He had on a black leather type skirt, fake leather, but still great looking with the top he had on. His wig was a long wavy black- and red-haired wig that came down to the middle of his back. His legs were covered with fishnet stockings and his feet were in a pair of red patent leather 6” platform heels.
Once he had finished the twirl, he stopped, and I could tell that he was extremely nervous about what he was doing. He was very shy and kept looking down but looked up every now and then to see what my face was saying. He had done an excellent job on the makeup, it wasn’t overdone, it covered the “manliness” of his skin and contoured his face well to make it look a lot more feminine.
“Well then, it looks like I was working with Chris, but now I am working with Christina? And it seems that you have done this before. Do you have any particular photographs that you would like to get done for your modeling portfolio Christina?” I said to him as I finished moving the lights around and changing the settings.
He still didn’t say anything but moved to get on his knees. When he got down, he put his hands upward on his knees and bowed his head. Now, I am not an expert in BDSM, but I know that this pose is a pose of submission. I wasn’t sure what he was submitting to, but I decided to start taking pictures and see what he did next.
I moved around him and got images of him in this position from a lot of different angles and then moved the lights around and tried out different colors and lighting angles. As I was moving the lights he moved a little. When I had moved back around to the front, I noticed that he had lifted his skirt so that you could see the panties that he had on. The panties matched the bra, very lacy and see though. I could see his cock tucked into the tight panties with the skirt pulled up as he had it.
I began taking more pictures showing the new details that had, “come to light”. I could see his cock twitch every time I moved in closer to get a more detailed photograph of the panties. He still had his eyes closed, but he could hear as I moved around him. His cock was reacting to each movement I made. He was holding completely still other than that.
As I moved around behind him again to get some other shots from that angle, he moved again. This time when I came around front, I could see that he had released his cock from the confines of the panties, and he was completely hard. The cock was twitching to the rhythm of his heart. He was very turned on now, that was quite obvious. He was having a difficult time keeping his hands still and his eyes closed.
I admired his cock for a few moments and then started taking more images, showing the details of his flesh, hard and sticking out a few inches past the end of the skirt. It was a beautiful specimen. Great dimensions, not to thick, wonderful length, not too bent, but not completely straight. I was having a difficult time not reaching out and caressing it and feeling it in my hand.
Like he could read my mind he slowly opened his eyes as I was taking more detail shots of his cock. He looked up at me and reached out and placed his hand over my crotch. When I didn’t move away, I guess he took it as an invitation and started to undo the zipper of my jeans. I didn’t know what to do or what I wanted, so I did what I knew best and started to take photos of the whole process.
I just continued shooting while he undid my belt and the button holding my jeans shut. I wasn’t wearing underwear and my hardening cock popped out as he started to pull my jeans down. I watched him lick his red lipstick covered lips as he saw it and reach out for it. He wrapped his hand around my shaft and started to move his hand back and forth slowly and lightly on it, savoring the feeling. I could see the lust in his eyes as he did so. My cock just jumped at the touch and I continued to take photographs while he stared at and stroked me.
Christina slowly moved his hand up and down my shaft while I took closeup photos of his hand in various positions in the motion. The red fingernail polish on his thumb reflected the lights to varying degrees in each of the photos. My cock was completely hard by this time and he was licking his lips even more with each stroke of his hand. I focused on his lips and the wet red lipstick covering them and took more photographs showing the movement of his tongue over his lips. In the pictures you can’t tell they are men’s lips, and the images were quite sexy.
I kind of figured what he was going to do next but wasn’t sure when or how he would approach it. I saw him move his other hand down to his own cock and lightly brush his fingers over it while he continued to stroke mine. His eyes never left the tip of my cock and he almost looked completely mesmerized by it. He kept stroking me and himself for another thirty seconds or so and then he leaned in closer and touched the tip of my cock with his lips, like a gentle kiss. This made for a wonderful photograph and an intense tingle shot up my spine at the same time.
I wasn’t sure I would be able to keep taking photos for much longer if he went any further, which just then he decided to take the head of my cock in his mouth and run his tongue side to side on the bottom of my head. I took a couple more picture while he was doing this and then I gave up on it. I placed the camera on a chair nearby trying not to pull away from him and closed my eyes to enjoy the sensations of his mouth around my dick.
After sucking on the tip for a little bit longer he took more into his mouth, going a little further and pulling back out to just the tip each time. Soon, he had the full length of my cock in his mouth. He took the full length, and I could feel the back of his throat. He didn’t seem to be gagging at all and began to moan a little with each stroke. It felt really good. He had a lot of practice at this and was extremely good at it. He moved his hand in time with and against the strokes of his lips over me. HIs eyes were closed again, and I wasn’t sure who was enjoying it more, him or I.
I didn’t know what to do with my hands, so I put one on my hips and the other I placed on his head as he continued moving up and down my cock. I couldn’t believe how soft his mouth was. It felt so good, I closed my eyes and just enjoyed the feeling he was giving me. I felt him pull back till he had just the tip in his mouth and he wrapped his hand around my shaft. I looked down and he was pumping his cock under the skirt with his other hand as he really went to work on my cock.
He started pumping me with his hand and sucking harder on me. I wasn’t going to be able to hold out much longer and I think that he could tell. He was jerking himself off harder and faster as he sucked harder and faster on me. I could see the tip of his cock on each stroke of his hand and it was starting to get a little pre-cum on the tip and each of his strokes was spreading it over his head making it a little shiny.
He moved his hips a little and I saw his cock start to shoot his first load onto his skirt and top, straight up towards me and under his face. He sucked harder on me and his strokes got a little sporadic while he was shooting his loan all over his clothes and the sight pushed me over the edge.
I closed my eyes again and moaned loudly as my first shot caught him a little off guard. He recovered quickly and swallowed, pulling me deeper into his throat and I continued to shoot a couple more shots directly down his throat. It felt amazing!
I was spent finally and had to sit down once he slowly pulled his lips from my cock and licked all around the head getting as much cum as he could. After licking his lips clean, he stood up and went back to the changing area. I got up after a couple of minutes and went to the computer to move the images from the camera to the thumb drive for him.
He came out about twenty minutes later and was once again dressed as himself. All traces of femininity were gone, no makeup left on his face, no wig, no breast forms. He was completely back to himself. I smiled at him and handed him the thumb drive. He started to reach for his wallet, and I put my hand on his and smiled wider at him.
“I think you are paid in full on this one Chris.”
“Thank you, Jack. I had a good time, and I am sure the images came out great!” he told me as he pushed his wallet back down in his back pocket.
“Oh, they came out great, and I am sure you will enjoy them. I hope to be able to work with Christina again sometime and get more erotic art images of her!” I said smiling again.
“I am sure she would love that!” he said as he walked out and waved before closing the door behind him.
