69plusoneCalifornia is just too far to drive from NC lol. There used to be a CD/Gentleman in Albermarle/Charlotte area named Brenda who used to have an entire ensemble of nice women's clothing and would help you do your make up in their basement and then do photo sessions with you. I went one time, I was very nervous as I am not a CD O am a masculine male with a very short professional goatee and as much as I love wearing lingerie I never had any non pervy looking photos. I brought a lot of my things for this photo session, they were already dressed more age appropriate with a longer floral dress, blouse, wig and makeup. I felt a little out of place but he assured me it was fine, he had sone many tasteful nudes, magazine shoots and things of that nature so I went forward with it. It was close to two hours of one of the best times I've ever had. Brenda was around 70 yrs old then but still very active and physically fit. I went into the back room where all the clothes were and got changed into a corset, stockings, panties and then I came out. He said it looked great but wanted to add a few touches. He had many pairs of women's heels, pumps, wedges and sandals that were all sizes up to 15 so for the first time I had some cute shoes to go with it. He had some basic color women's chiffon blouses to add to what I was wearing to get some more photos. Then he had many very slutty ruffle type sissy outfits and sheer bras I could get into. These changes all made me feel very comfortable and put me into a great mood. He convinced me I could touch myself if I wanted to enhance my look (or size) which I gathered meant to play with my cock. I was a little uneasy about that but I started rubbing my cock through my satin panties and the fact that I had taken Viagara to help hopefully add some size to manhood while taking the pictures for better pictures didn't take but a second or two and I was rock hard. Too hard to contain in the panties, a problem none the less he offered some sheer vintage panties with some garter belts. I said sure, not really thinking this was going in a great direction though at this point just go with whatever. Life is an adventure and not many times in life have I ever really regretted anything I have done. So he brought out a couple of Rago suspender belts, different colors, all I had was black and white stuff but he had many items. So I tried a few on, he would help put them around me and I would brush against my cock once in a while so it was at 85-90% full erection the entire time. However he made me feel very comfortable about being erect and told me it looked fantastic and how great I looked in everything that the harder I was the better it looked. In satin garters, with large sheer panties he took many photos, changing them out I was so fucking hard and so fucking horny. He never really touched my cock, he would instruct me to move it to the side, grip it with two hands, moisten it a little with some saliva. Standing, sitting in a chair, laying on a 50's vinyl couch, bending over from the rear he easily took a couple hundred photos. He told me to go ahead and masturbate if I wanted to, I had a very nice white ensemble on with a gorgeous blouse He kept talking to me and I must have have had the look because I had been edging very close for close to an hour. He said to me "it's okay if you orgasm", he knew it was going to be inevitable and asked me if I wanted him to video it? I told him okay as I was sooooo close. He switched his camera over to video mode and I did just that, videoed about two minutes of one of the most intense orgasm's I had ever had given myself. I shot 2-3 heavy ropes of cum, landing on my corseted stomach, stockings and all over my hand. I was drained, I didn't know he ket videoing though. Of course after a few seconds I felt embarrassed and he went and got me a hot wash cloth. When he got back I was already half changed I said thank you as I think I was embarrassed at that point. He knew it so he kept making small talk and he told me I think you're going to be very happy with the finish product. He took the flash card out of the camera and put it into his computer for me to see. They were all very high resolution photos and although his basement wasn't a great looking facility he had great backdrops and I didn't realize it but he had phenomenal lighting. The photos he took were amazing! he clicked on the video and it was the first time I had ever seen myself orgasm and watching it started making me hard again. I told him how amazed I was and how amazing he was. I paid him for one hour which was what we agreed upon in advance, he pulled the card out of his computer, handed it to me and I went on my way. I enjoyed it so much so I tried to get him to do it again a year later and he never returned my email. I have tried many times to reach out to him again but never received a return email.
Reading you post reminded me of my adventure and thought, someone who was truly vested in it, had photographer skills and invested some money could really make some people in our circles very happy. The hardest part would be remaining professional and not pursuing contact with them. I know I enjoyed it enough that if you were set up around here I would do it again in a heart beat.