Nandita To Nandini
- 4 years ago
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The Photographer And The Sissy free porn video
I was 2twenty-two, closeted fully and living out my sex life in fantasy and on the internet. I had discovered my love of dicks in my teens, followed a few years later by my fetish for dressing up like a girl. I have no idea why, but the sight of my own body in tights, knickers, stockings and heels made my boy pussy (dick) wetter (harder) than anything else, straight or gay.
Luckily, I lived alone (in a private studio apartment, in a major city in the Netherlands), so I could basically live out my fantasy at night as much as I wanted: ordering clothes, shoes, wigs and make-up to be delivered to my doorstep in discreet packages, dressing up in front of the mirror and - quite often - giving little shows on webcam. I even made an occasional bit of money through a Dutch site similar to Chaturbate.
Less luckily, I was also very shy. Although I'd had a handful of sexual encounters and a short relationship a year before, I did not dare set up anything with a guy who ahem liked a girl with a little extra in her pants. I have to admit I ghosted a fair few guys, not intentionally but I would always get cold feet when they wanted to meet up in real life. I was afraid of meeting people at their or my house, and a date in a public place didn't really feel like an option as I didn't want to go out into the open in my dress and lingerie yet (and meeting as a boy felt like an instant turn off).
Then, one evening, I got dolled up and opened my laptop to see what was going on online. I went on a gay forum that I had posted some pictures on, and checked my messages. There were a few thirsty guys (as usual, for some reason most of them German), and I gave out some semi-flirty responses to the ones that seemed halfway hot. The fourth message in was very different, however:
"Hi Tanja, my name is Rick. I'm a photographer in [PLACE], I do non-erotic work but also a lot of sensual stuff, including LGBT. You can find my website at [WEBSITE].
I'm doing a study on transvestitism and crossdressing. The idea is to capture the female in the male, to show that even 'men' can express femininity with the right clothing, body language, lighting - and hopefully the right photographer. I was wondering if you might be interested in doing a session. I have a few clothes you can put on, if you don't have your own. You are in charge - if you're uncomfortable at any point we can stop right away. I'd like to publish the pictures, but I can make you unrecognisable if you want. I can't pay you, only your travel expenses, but if things go well I might be able to offer you some paid work too. Let me know!"
Naturally, I went straight to Rick's website. It was a well designed page, clearly the work of a pro. The front page contained examples of his non-sexy work: weddings, families, nature... I noticed a button for 'erotic' in the banner and clicked it, then clicked 'yes' for the (slightly redundant) 'do you want to see 18+ content?' pop-up.
This was a different world altogether. This page was full of all kinds of kinky picture galleries, each one lit and shot beautifully. There was a steamy gallery of a naked older women caressing a twenty-something girl in lingerie, one of a nude man and women in a forest, kissing up against a tree, and one of three men in a darkened studio - where in one picture two of them very strongly were suggested to be fucking.
Then, I found the crossdressing stuff. This was wonderful. His favourite model appeared to be a red-haired (wigged), very skinny 'girl' in her early twenties. She was in several galleries, posing in provocative dresses, heels and lingerie; in some cases tied up for a slight BDSM feel. If he could shoot me like that, I thought, I would never stop cumming over those pics...
Naturally, I replied and we got chatting. He seemed like a good guy: he was (slightly) flirty in complimenting my looks, but not overtly sexually aggressive in any way. The fact that he had a legitimate website gave me the idea that he was on the level. Ever hesitant, though, I asked for a picture that wasn't published but was part of a series that was, so I could verify that he was who he said. I also referenced the red-haired girl, hoping to see a little more of her...
I got what I wanted. The picture he sent had the red-haired beauty pictured from the side, her tongue sticking out all the way so that the tip just about touched something...
The tongue was reaching out to the head of what was likely the biggest dick I had ever seen.
We set up a date. No strings attached. I could come over on a Saturday, bring all my clothes and stuff, get dressed privately in my own dressing room, and take some pictures. Rick would help me with my make-up, lend me some stuff to try on and direct me. The pics would only be published if I was OK with the results. Naturally, I shaved EVERYTHING the night before...
On the train ride over, I could not stop thinking about the tongue pic. Was it Rick whose dick the red-head was about to lick, or a model? Did they actually have sex? Was he expecting to have sex with me as well, regardless of his 'no strings attached' vibe?
I rang the doorbell to his studio. A tall, well-built, crew-cut guy in his mid to late forties opened the door and smiled handsomely and confidently. His grey eyes had a mischievous sparkle. "You must be Tanja," he said, smiling away. We had coffee and chatted, him confident and open, me slightly awkward and guarded. He then showed me to my dressing room, which was like a large walk-in closet full of racks of clothes.
We had agreed that, for the first shoot, I would dress myself entirely without input from him. As I was still a little apprehensive, I started with a slightly more muted outfit: a slightly plain but tight-fitting grey dress that covered the front came up about halfway above the knee (pic below with different stockings, taken some time earlier at home), with a curly brown wig. I put on some fairly plain black lingerie, as there wasn't much to peek under the dress. I decided to make a statement with the stockings - stripy black/sheer numbers - and pretty black six-inch stiletto pumps.
Rick nodded approvingly. "Yes, this is something we can work with!" He complimented my slim frame and 'feminine' bubble butt, and helped me with some beautifully understated make-up, which took much longer than I usually did on my own but with a much better result to show for it. We finished it off with some bright red lipstick, then got off to shooting.
There was a white canvas area to use as a background, about three square meters on the floor and covering the wall behind it. I posed just upright at first, first front then back, then legs crossed slightly. Rick directed me to get in touch with my femininity as much as possible, think like a woman and move graciously like a woman. I struggled at first, but started to find my flow a little.
He then put a chair in the middle of the area and directed me to pose around it: sitting cross-legged, leaning over from the back, then leaning over from the front with my butt to the camera. I started loosening up a little, shaking my booty somewhat provocatively for the camera. "Work it, girl," Rick said, snapping away.
After the first session, Rick helped me remove my make-up. We started chatting about the next outfit. "I don't really know how often or with whom you do this," Rick said, "but do you ever, like, role play?"
"What do you mean?" I asked.
"So as part of the drag or crossdressing culture, some 'girls,'" he said it with air quotes, and a wry smile, "like to take on a sort of persona, like a character?"
I was intrigued. "Ok... like what?"
"Well, for instance, the red-haired 'girl' you liked, she liked to play around as a nurse. Here, I'll show you." He pulled the picture set up on his laptop. The pictures showed my crossdressing idol in a tight white 'sexy nurse' outfit: short white dress, pink stockings, hot pink wig with a little nurse's cap, and a stethoscope as a sort of prop. She posed provocatively on her knees, lying on her side and bending over while turning back to the camera.
"Nice!" I said, feeling a tingling in my panties. "So... what sort of character would suit me?"
Rick stroked his pencil-bearded chin. "I was thinking, because you're pretty pale-skinned, maybe a classic French maid? You know, black dress with an apron, sheer stockings, a duster... Like that"
I was all in. This sounded mega hot. Rick had an outfit ready - he said he picked it out when I told him I'd come over, as he thought it would suit me... And it did. The dress was silky black with white accents on the sleeves and bottom, fitting tightly around my bubble butt. It came up much higher than the previous one, the hem halfway up from my knee. It came with some long white satin gloves. The stockings were gorgeous quality garters, I enjoyed just running my fingers over them. But the kicker was the shoes: they appeared to be actual Louboutin heels! Couldn't really tell but they had the logo and (of course) the red soles. These were something else...
I picked out the underwear from the sets he had on hand (it seemed to be clean)... Losing my inhibitions ever so slowly, I went for a slightly racier number: dark red bra and panties with a Chinese-style print, complete with a garter belt. I kinda felt like showing it off in the next photo session.
Rick gave me a black 'bob wig' and a duster, and started shooting. I pretended to dust things put onto the photography area: a standing lamp, a chair, a small table... I provocatively turned my butt towards the camera and started bending over, crossing my legs. "YES!" Rick said, snapping quickly. "I love how you do that!"
We took a little break. "Rick," I asked, courage gathered. "In that last picture, you sent me... I noticed that there was someone else in there... someone... naked?"
He laughed coyly. "Hahaha, well... How do I explain this? Sometimes, when I get very comfortable with a model, I like to take my clothes off when shooting her. It's like... It helps make everything loosen up, you know, the whole atmosphere gets a bit lighter. That model in particular just feels a lot more free when she's not the only one showing herself. Does that make sense?"
I paused for a second. "So... that was you in the picture?"
He grinned. "Guilty..."
"Impressive!" I said, attempting a seductive wink. He laughed, a little embarrassed. "We could... try it out if you like?" I suggested, not knowing whether I was overstepping or something. I wasn't. Rick got out of his jeans and t-shirt (he didn't appear to be wearing underwear) like lightning. He had a nice body, maybe carrying a few pounds too much to be considered athletic but very firm for his age. His dick was... clearly a grower, not so much a shower - it didn't look THAT impressive when soft.
We shot some more pictures. I was on my knees, dusting the floor and making flirty, girly gestures like putting my gloved fingertips on my mouth and making a 'good heavens' face as if startled by something. Rick was more and more excited- in his instructions, at least. "Yes, girl! Yes!" I started seeing it as a challenge to get his dick as excited as his directing was... I sat on the chair, legs crossed, then slowly uncrossed them Sharon Stone style to give him a look at my panties. It looked like something was happening already...
Next, I got up and turned around the chair again. Putting my knee on the seat, I started pulling up the hem of the skirt ever so slowly so that the tight panties around my butt and the garter were entirely visible. I turned around, trying to give a seductive look to the camera. Rick was still snapping away, biting his lip ever so slightly. His dick was at full mast.
Then, he stopped. He grabbed the tripod from behind him, put the camera on, then walked over to the 'props' we had been using. "I have an idea," he said. He picked up a small lampshade from a bedside lamp, then fidgeted with the camera. He got up next to me, giving me a close-up view of his highly impressive girth. "The camera is on self-timer. Here's what we'll do: You're dusting, then you start dusting the lamp, then you discover what's under it and you're shocked - remember to show it to the camera!" I knew exactly where he was going.
Rick rested the lampshade on his cock. I knelt down on all fours and dusted around him for a few seconds as the camera started snapping, then up his leg, then over the lamp. I tried to give my most stunned 'scream queen' look to the camera as I removed the shade to reveal his dick, putting my fingertips on my bottom lip and making a shocked 'blow-up doll' face.
Then, the clicking of the camera stopped. I looked up at Rick. I was on my stockinged knees, with his dick standing fiercely just above my face. He looked down on me with a coy smile. I couldn't resist anymore. I grabbed his thick shaft and took it deep into my mouth, until I nearly gagged. He tasted deliciously sweet.
The sexual tension was finally broken, replaced by actual sex. I was blowing him like no tomorrow, thrusting my head back and forth as he stroked my wig hair and moaned manfully. Suddenly, I got an idea. "Wait!" I said, getting up and traipsing toward the make-up table in my clicking heels. "Can you do the self-timer again?" I hollered to him, frantically searching through one of the make-up drawers.
"Uhm, sure..." Rick said, and he moved back to the camera.
"Ok, give it thirty seconds," I said, finally finding the hot pink lipstick I was looking for. I applied a thick layer on my lips as quickly as I could without making a complete mess, then got back quickly in from of the camera. "Now you go back to where you were."
Rick followed my instructions, looking a little puzzled. I shamelessly grabbed his shaft and sucked him, puckering my lips to make sure his dick got covered. Then, when the camera started clicking, I again made my 'surprised' face to camera, as if I had just been caught 'en flagrante', with the camera catching very clear evidence of what had happened...
Rick finally realised what I was doing, and giggled, "Nice touch!" When the camera finally stopped clicking, I wanted to get back to my 'maid duties', but Rick gently grabbed me and pulled me up. Pulling me close, he kissed my pink lips, and we made out until his mouth was the same colour as his groin. He helped me out of my dress and grabbed my (considerably smaller) cock in my panties, and we pleased each other with our hands for a while.
Then, Rick put his hand on my butt. First on top of the panties, then slowly sliding under and between my crack. I knew where he was going, but I wasn't really into anal at that time (and also terrified of his size...) so I quickly decided to kill that idea off early. Instead, I grabbed his hand, pushed against his chest and told him to lie down on his back.
I slid down to his large member again, and got back to working it like a good little slut, this time taking only the head and firmly circling it with my tongue as I stroked his shaft. Either my tongue work was amazing or Rick was already close, but soon after he gave me started to try to pull me away. I let his cum fly against my face, covering my right eye in something other than mascara.
I helped myself to a finish over his stomach quickly after, as he lay panting in recovery, and we laid down together for a few minutes, saying nothing. "Is that how you expected today to go?" He finally asked.
"I had no idea what to expect..." I replied. "The last picture you sent gave me a rough idea of what might happen though."
He giggled. "Yeah, somehow things work out this way," he mused. "So, would you like to do another dress-up session."
I gave it a second's thought, but decided that was enough for one day. "Not today, maybe next week?" I replied. "I'll let you pick out the outfit..."
He gave me a mischievous look. "Don't tempt me... I think I already have something in mind."
I couldn't help but wonder what this crazy imagination had in stall for me, as I slipped out in my civilian clothes...
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