Updated: Oct 3
Back in 2011, Paula had been dating a guy named Frank. He was a lot like us in that he had a background as a Baptist minister but had moved in other directions later in life. She really liked him, but just as they were moving from making out to their first time in bed, Paula’s father passed away. After that Paula didn’t date again for nearly a year and by then she had lost touch with him.
We were both surprised when in November of 2012 I got an email from him. It seems he had been following my first blog, and he had read how the previous summer I had written a piece on how I had finally self-identified as bisexual. In the year or so since we had heard from him, he had begun to experiment with something else he had been thinking about for decades. He had begun to experiment with cross-dressing. In this he had been greatly assisted by his new girlfriend. He had discovered he really liked wearing women’s lingerie. He sent some phone pics to me for my opinion.
I let him know that he certainly had the body to pull it off. I large part that was because, even though he was in his late 50's was working as a tennis pro. Unsurprisingly though his self-made photos were terrible. He wanted to know if I could shoot some photos of him in lingerie.
In December I went up to Asheville to his place for a test shoot. The shoot was informal, I didn’t even bring my lights and we talked more than I shot photos. I was surprised at how much it turned me on after I’d put away the camera, when he turned on music and danced for me, taking off his panties. Even though I identify as bi, I normally don’t get aroused by men’s bodies (only hard cocks). But, dressed up in lingerie, make-up and a wig, I found myself imagining kneeling in front of him sucking him off and bending him over the couch and fucking him.
I asked him if he would like a blow job, he declined, but did let me play with his cock. When I left I knew he was confused with his desire for me to do what I had suggested. The transition to cross-dressing was a jump for him, but he just wasn’t ready to try sex with a man.
We carried on email for some time, then in March of ’13, he sent an email asking if I was interested in doing photos of me giving him a blowjob. Of course I knew that the photos were mostly a justification to let me go down on him. We made plans for the next evening. I went to his place and set up my lights and tripod with a radio controlled shutter release. I was correct in my prior evaluation. He most definitely wanted to guise his first homoerotic sexual contact as acting for a photo-shoot. I was also nervous since this would be the first time I’ve been with just a man (not part of a threesome).
I set up the shoot as telling a story. I was a sales-man and he was a “housewife”. The first set of photos was of us at the door fully dressed.
Then I reset the lights and we sat on the couch. He surprised me by quickly getting into my pants to give me a hand job.
I reset the lights and shot photos of me undressing him as he stood in the living room. I went to my knees and I made oral love to his beautiful ass and cock. Repeatedly he had to stop me from what I was doing out of fear he would climax before we were done. The best part was when I sat on the floor against the couch and he stood in front of me and fucked my mouth, shoving his cock down till his pubic bone was pressed on my lips and his long cock was down well into my throat.
His penis was longer than any that I'd ever had in my mouth before and so it went significantly further down my throat. He held it in for a long time then began to stroke in and out, i.e. to actually fuck my mouth. The feeling of being pinned back while he fucked my mouth was thrilling. Later he did the same thing as I sat, and he stood on the couch forcing his cock down my throat. I loved every second of it. Though he briefly sucked me in 69, the "photo-shoot" was nearly all of him fucking my face.
The combination of his feminine appearance and masculine behavior was something I had never experienced. He has an ass any woman would be proud to own, and I kissed and licked it generously that day. The photos came out great, but he asked me not to show his face or anything identifiable in the room when I posted the photos of us on my Tumblr blog.
When I got ready to leave, I could tell he was confused. I helped by giving him the language of “That was fun. It doesn’t change who I am, it was just having fun”. He agreed, but it was three months before I heard from him again. Just like before with no warning, he requested a “photo-shoot”. In our email discussion, I mentioned that Paula had wanted to come so we could have a threesome. He was all for it, after all they'd not had sex when they'd dated before, and both of them wanted to get together. Sadly, the morning I was packing to go, she was called into work. She wished me well and told me to have fun.
It was mid-summer at that time and the room was hot. He had really improved his make-up and bought new lingerie. He looked good enough that I have no doubt he could have gotten more than a few self-professed straight guys to go to bed with him. He'd also gotten down the art of walking and talking like a sensuous woman. I got an erection right off thinking what his behavior seemed to indicate he wanted to do. However, when he'd get really close to me, like he wanted to kiss me, I could tell he was torn between his desire and his religious background.
As the "shoot" went on, he became even more nervous and sometimes seemed distracted and/or unsure. This time, he couldn't keep his hands off my hard-on. He really seemed to enjoy holding it and jacking me off. However it was odd in that while he spent a lot of time with my penis in his hand, he also seemed even more uncomfortable with his homoerotic desires that were now fully realized. At one point when he sat on my lap and jerked both his penis and mine at the same time, he slid down to the ground in front of me and put his mouth very close to my dick as he played with my erection. I could tell he was getting up the courage to just let himself go and suck my cock without shame, but he never did.
Later I tongued his ass hole while I jacked him off, something I did not do the last time. He was really getting into it. I told him how I was so ready to fuck him. He did not say yes, but didn't say no either. His whole body was responding and there was no question that he, for a moment had let himself really enjoy. I was sure he'd brought the lube out and put it on the coffee table because he was at least thinking about having me fuck him. After all, that would be the way to really feel like he was a woman.
I was sure he was about to ask me to use the K-Y and drive my cock all the way into his ass; but, suddenly he tensed up, like he had come to a decision. Our "photo" session ended right after that and neither of us climaxed. He seemed in a hurry for me to leave.
As for the photos, my radio control unit was not working. I set the camera to shoot one frame every minute, so the pics did not come out nearly so nice as the last time since we didn’t know when it would shoot. When I sent him the edited photos, he made an interesting request. He wanted a photo of me masturbating to orgasm. That seemed to tell me he was still thinking about having a full sexual contact session. I tried to make the photo. It turned out a difficult thing to shoot on my own. He also seemed very excited about the prospect of Paula and I joining him for a threesome. It appeared that he was wanting to continue his transgender/homoerotic exploration.
However, before we could make the plans, he stopped answering email. I never heard from him again. I don't know if he pursued his female identity and sex with men further, but whatever he did, he did not ask Paula and I to join him in it.