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Camera Shy

"Crossdresser seduces reluctant cameraman"

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Author's Notes

"Monica Cheeks is an amateur cross-dresser and author."

I’d been getting a lot of negative feedback about my camera work. Bad angles, glaring lights, occluded shots, and missing things completely; most recently, the money shot of a full load that went everywhere: my eyes, ears, wig, lips, bra, throat, etc. while the camera was close-up on a bedpost. Audio was clear, so viewers knew what they were missing and were displeased.

Most videographers just leave those shots out, but I leave them in because there’s something tantalizing about them. Something left to the imagination. Like my shots from behind, where you can see me on all fours with my tight skirt lifting to show my seamed stockings and cute little ass in black silk panties, as my long strawberry blonde wig bobs up and down in a man’s lap. I like those shots, but they infuriate viewers who want to see my painted lips wrapped around the guy’s cock. 

Okay, so give them what they want. CAMERAMAN NEEDED FOR AMATEUR CROSSDRESSER’S SEX SCENES. I’d become fairly popular on the site (as Monica Cheeks) and so received several offers the first day. My only requirement tends to be a circumcised penis, but I greatly prefer straight, middle-aged married men. Like myself. It’s just the right level of wrong from my perspective. So I chose the applicant who best fit that description, presuming he’d be a participant in the video. Manning the camera, but up for a little POV when I felt the urge to reach through the glory hole of the fourth wall. 

So when he showed up first, and I greeted him at the door in t-strap pumps, little black dress, seamed stockings, silk panties, fake breasts in lacy black bra, etc., etc., I expected to have a little warm-up session before my leading man arrived. I offered him a seat, informed him that my co-star was running late, and suggested that we… set the mood, as it were. He was just my type. About six feet tall, paunchy, fifty or so, with a defeated bourgeois expression. (I've managed to stay in shape, but I love a guy who's let himself go a bit.) As always, I was crazy nervous, but forced myself to my knees and laid my palms on his thighs, smiling up at him and then looking down at what I expected to be a blooming bulge, but was just a smooth inseam. The man abruptly stood up and informed me, “No, no, no, I’m just here to shoot the video, that’s all.”

My confidence shaken, I rose from my knees and stammered out, “Oh, yeah, of course, sorry, didn’t realize…sorry.”

I expected a reassuring “no problem”, but instead received awkward silence as he looked around the room to avoid my gaze. I felt a bit humiliated and offered him a drink which he accepted without looking at me. Feeling self-conscious, I adjusted my tits and my wig and sat down cross-legged across from him, rather than, as I’d wanted, cozying up next to him, where he sat with one hand holding the camera I’d given him and the other shielding his crotch. Instead of feeling sexy in my tight dress, stockings, and heels, I was suddenly feeling like an object of ridicule. This was something new. I was used to guys eagerly whipping it out before we had the foreplay I so desired. They couldn’t get it into my mouth and/or ass quickly enough. But here was someone who wasn’t into it? Just a looky-Lou? Perhaps he simply enjoyed watching others demean themselves, maliciously laughing at them from the other side of the camera? Small talk seemed an absurd alternative, and so the silence was extensive and excruciating….as I checked my texts for the ETA of my willing participant (for the sixth time) there was deliverance: 

Knock knock

Who’s there? 

Man wanting to fuck you doggy style. 

Man wanting to fuck me doggy style who?

Relief washed over the film of humiliation as I rushed to the door (almost tripping on the four-inch heels I would never walk gracefully in) and with my most seductive, low-key smile welcomed in the man who would soon be looking down at my crimsoned lips parting to receive the throbbing head of his erection. Or maybe there would be no erection? Maybe he also thought I looked ridiculous and turned off, was having second thoughts? Maybe this was a disaster and the two men would apologetically backpedal out the door and leave me all dressed up with no one to blow?

This second arrival was also my type, but a little shorter, about 5’8, so we were immediately (temporarily) eye to eye. His paunch was more of a full-on belly – his thick, hairy arms dangling down like an idle mechanic’s. (I almost wanted to get a wrench for him to hold. And use?) I asked him if he’d like something to drink, and he followed me into the kitchen where I grabbed a beer out of the fridge. I was so nervous now I had begun to shake and was unsteady on my pumps, beginning to feel mortified about being dressed as I was in front of two complete strangers and rethinking this whole escapade. But in one gesture, the romantic lead dispelled all his co-star’s fear, lifting my dress and clutching my ass as he reached around with the other hand to squeeze my left breast. I put the beer on the counter and let out a relieved, inviting, almost ecstatic “Mmmmmm” as I thrust my ass back into his crotch, grateful to feel a forming erection nuzzled between my cheeks.

It had begun. And I could feel myself sinking down into this role: sexy slut ready and willing to please her man in any way he desired. Literally sinking to my knees, I turned to face his bulge veritably bursting from his jeans, which I awkwardly unzipped after a few tries, releasing my hero’s not quite hard (but rapidly en route) member. 

So where does the video begin? You may be surprised to see our hero’s hand on my ass in the opening shot, as the reluctant cameraman had already begun filming, which I only noticed after the fourth or fifth pump of our hero’s cock into my mouth, its smooth shaft gliding to and fro over my stiffened tongue. I had completely forgotten this inimical other presence until I noticed the third man in the periphery. With my hero’s dickhead tickling my uvula, I turned to face the camera and the man holding it. Surprised at his diligence, I smiled (as best I could, half-gagging on my movie star’s ample and now fully erect penis). 

My knees were beginning to hurt, so I let his manhood slide from my mouth, gripping it firmly in my right hand as I rose to face him. With his dick in my hand, he leaned in for a tres romantique French kiss, his tongue thrust in as his wiry, salt and pepper beard tickled my lips and cheek, eliciting a girlish giggle from me. Lost in the passion of the kiss, I once again forgot the presence of the third man who I now noticed was panning up and down, to the kiss and then back down to where I firmly gripped my lover’s thickly veined cock, gently tugging on it each time his tongue thrust against mine or darted to my cheeks.

Then I suddenly had that moment at, which I fully recognized what I'm doing and what I'm wearing while doing it (could at once feel the seams in the stockings, the tight panties sculpting my ass, the tits in the lacy bra, the blush, eyeliner and lipstick, the strawberry-blonde wig, the pumps barely supporting my swooning weight) and felt a rush of ecstasy that, combined with a heel catching a groove in the linoleum, knocked me off-balance and jerked me out of the kiss. I struggled to regain my balance on the four-inch heels, and both lover and cameraman laughed, but not maliciously; it was part of the fun. Part of the game. We were getting on.

Hand in hand, my hero and I proceeded to the bedroom, where I’d left the shades up. There was a frequented walkway within view, and I didn’t have a problem with Peeping Toms. I sat down on the bed to get eye level with my man’s now throbbing cock and thrust it into my mouth, wildly sucking and groaning, occasionally releasing it to flick my tongue all over the head and down the shaft to where his tightening balls now lifted a bit, as he moved his leg so I could get my whole face underneath, dropping his sweat-glistening balls into my mouth. And as I slurped at them like a scoop of ice cream, I recalled the presence of the third man, who was now inches from my face, capturing the sights and sounds of my slurping. I craned my neck to face the camera and let it (him) watch my lips and tongue caressing, kissing, sucking and even ever so gently biting the tightly packed testicles, as I could hear the approving oohs and ahs from above me. 

While the camera obscured most of his face, I could see the cameraman’s mouth and felt as if I could see it twitching, clenching, watering. I could almost feel him wanting to tighten the shot until his face was where my face was, maybe giving me a peck on the cheek, or thrusting his tongue into my mouth as I sucked on the balls. Though maybe this was my imagination. To heal my wounded pride.

I came up for air and flashed a wicked smile at our hero who gave me a “good girl” and lifted my chin to where the still firm head of his cock was itching to plunge back into my mouth. I accommodated this plunge and resumed my wild, sloppy sucking of the shaft, now pumping the base with my sweaty palm as his cock continually plunged in and pulled out, half from my movement and half from his thrusting. We were poetry in motion. Sweaty, drooling, gagging poetry in motion. I released the shaft to clutch his thighs, but continued sucking, “look ma, no hands!” and I could feel some foreshadowing cum spill into my mouth as I slipped my palms over his hips to his hairy pot belly, which was now dripping with sweat as I head-butted it with each plunge down his cock. As I pulled the shaft out to bounce it on my tongue, a few drops of sweat from his belly and pubic hair splashed my cheek and dropped onto my tongue like a draught of ambrosia as I immediately swallowed the cock whole again, early ejaculate and crotch sweat streaming over my taste buds and down my throat.

“Yeah, suck that dick, baby,” he crooned. (Originality was not his forte, tended not to be for men who wanted what he wanted from me.)

After a few more wild pumps of the shaft, now hungrily dragging my teeth a bit as if tempted to devour it, I took it out and the head made a little “pop” from the suction of my lips. I so badly wanted to swallow it whole and in a fit of violence slapped it against both cheeks and closed mouth, as if punishing myself for being such a bad, bad girl. At which I heard my man repeat an ironic “good girl” above me, followed by the hero’s cliched, but no less thrilling next line, “Swing your ass around here, baby, I wanna fuck you from behind.”

Didn’t have to ask me twice. I released his cock, my palm caressing each raised vein it slid away from (goodbye cock, see you again soon!) and then swung my ass around as instructed, splayed arms out, face first, bent over the bed, wiggling my ass in anticipation. My leading man clutched my hip and slipped his fingers under the crotch of my panties moving them aside as his now rock-hard dickhead probed for entry. It was dripping wet, I could feel it dribbling at the entrance to my ass. Again I thought of (having again forgotten) the third man, who I now saw in the periphery, getting a side shot and moving in to show penetration.

Which. Was. Now. OCCURRING.

As the head crossed the threshold and the shaft slid in, I let out a moan so loud, it startled him and he stopped for a moment.

“Is it okay?” he asked, thinking it had hurt. Which it had, but was so so so okay. 

“No, no, baby, I’m fine, don’t stop. Come on baby, give it to me, fuck me, baby. Fuck my ass.”

(Was originality anybody’s forte in the throes of passion?) 

He seemed okay with that and started to pump, but slowly, gingerly as if afraid to hurt me. My groan had backfired: FUCK ME HARDER!!! I begged and he did. A little too hard to be honest, but I was so on fire it didn’t matter. And that’s when I noticed, over my shoulder, the cameraman getting an overhead shot of the ass-fucking. Which is to say I presumed it was an overhead shot from the angle, because all I could see was that…he’d taken it out. In one of my oblivious transports of desire, he’d actually gotten his pants off and it was out. The combination of this sight and the penetration of our hero’s cock and his hands clutching my waist, murmuring sweet nothings above me brought me to the brink of actually cumming (as he thrust I was rubbing against the bed), when there was a loud SLAP which I simultaneously heard and felt. Startled, my heart skipped a beat and then again, he smacked my ass.

“You like that, Monica? Huh? You like that?”

Before I could answer in the enthusiastic affirmative (his having said my name brought me back to the brink), he slapped my ass again and I once again became aware of the silk panties clinging to my cheeks and the seamed stockings encasing my thighs and calves down to where stockinged feet were tightly wedged into the sleek black pumps, and again came the overloud groan. But this time he recognized it for what it was and brought his palms down in a punctuating slap of both my cheeks and said, “You gonna make me cum, baby? Huh? Huh!?!” The last Huh!?! way too loud (I do have neighbors).

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“Oh my God, yes, baby, come on, sweetheart, let it go. Cum for me.” (The old standards in the throes of passion.) But then regained my composure to contemplate this culmination which was coming (so to speak) too soon. “You want to cum on my ass, baby? Or you want to cum inside me?” 

His reply, “What do you want baby, where do you want my load? Huh baby? Where do you want it?”

Hmmm, what was I in the mood for? I LOVE having a man’s cock throb out its orgasm into my ass as he shuddered and sputtered behind me, but I had to think of my audience. What was best for the video? Give them what they want.

“You wanna shoot your load on my face, baby?”

“That what you want, Monica? You want my cum on your face.”

“I want your cum ALL OVER ME, baby.” 

He came to an abrupt stop, was apparently close and so I ceased squeezing my cheeks and thrusting back into him. We needed a spectacular finale for this scene. He slowly, carefully pulled out and I returned to a seated position on the bed. And that’s when you see the POV shot: me gingerly holding his hard cock (careful not to detonate it) and looking up into the gaze of the camera’s eye. But it was the cameraman holding the camera in front of my ravisher’s face. And at that position, you can guess where the cameraman’s cock was (it was out, remember?). Fully erect, swaying a bit as he tried to hold the camera still, his member no more than a few inches from my pretty red lips. Was he offering it to me? I was kind of busy at the moment and unsure whether I should risk a cool-down with my co-star, but I wanted that cameraman’s cock in my mouth more than anything I had ever wanted in my life. 

But was that what he wanted? I was under specific instructions not to involve him. Still stung from the rejection and feeling shy, I returned to the member at hand. Smiled up at my chubby stud and started sucking wildly again. Maybe he preferred a slow, sensual blowjob, but his thick, veiny cock drove me wild and as soon as I wrapped my red lips around its pronounced pink-purple head I lost all control. All the while, I could see the other’s swaying dick (which was quite, quite hard) out of the corner of my eye, and with all my inhibitions gone in the ecstasy of an approaching cumshot, I grabbed hold of the cameraman’s member (still holding fast to my lover’s, though I’d lifted my face to look at the other man’s cock) and stroked a couple of times before he pulled loose and moved around behind to get an overhead shot.

Rejected again. Still feeling the ghost of his girth in my palm, I started to get angry this time rather than hurt. I gripped the shaft of my hero tight, looked up and, with a menacing, all-business scowl, said, “Cum on my face. I want your load all over my face.” (The old standards.) And as he looked down at me, all my anger melted away (he was kinda cute with that scraggly beard, beer belly and workman’s forearms). “Come on, sweetheart, cum for me.” And I had to stop myself from saying, “Come on lover, give it to me.” 

Lover? What? I get so wrapped up in the role sometimes I think I’m falling in love.

And it was with that unspoken declaration of love that a first jet of cum shot onto my lower lip and dripped over into my mouth, as my lover let out another too loud groan. Two more jets of cum hit my lips and cheeks and I let out one of my own too-loud groans as I swallowed back some of the cum. I was now cupping his balls and frenetically pumping the shaft, aiming it squarely at my face, but my strokes were so wild and there was so much shooting out it went everywhere, much like the cumshot I’d missed shooting recently. (Lips, cheeks, wig, dress, bra, etc.) Dazedly, I muttered Yes over and over and over into the cum shower.

You’ll be pleased to know this moment was recorded for posterity by the cameraman who was now standing above me with his balls nested in my wig. There was just so much cum. And, as I say, everywhere. I greedily swallowed down all of it that got in my mouth (less than half, but still quite a bit) and licked it off my lips and fingered a gob off my bra strap, thrusting it into my mouth like stray syrup from a pancake. His dripping, spent cock softened in my hand and I sucked the last drops out of it, gently now. Lipping a few stray drops out of his pubic hair and licking both thighs in the splash zone. Shamelessly, I even got down to all fours and licked up the many drops that had spattered the hardwood floor. This made both men laugh at me and it was utterly, thrillingly humiliating.  

From down on all fours, I suddenly looked up at the cameraman like a dog begging for a bone. But he wouldn’t look at me. He was visibly embarrassed and put his pants on, as he put the camera back on the nightstand. My lover was now fully clothed again and pressed a kiss into the top of my strawberry blonde wig, picked up his car keys, and bid me farewell. An embrace and one last passionate kiss would be nice, but I know how guys are after they’ve shot their load in my face, and so the condescending kiss on the head was more than I expected. Was actually kind of sweet. 

The door closed behind him, and the cameraman and I were back where we had started: in awkward silence. He put his jacket on and was about to leave without even saying goodbye. He was clearly one of those guys who couldn’t overcome their shame from these interludes.

And suddenly the anger returned. His hand had turned the knob and as the door creaked open I almost shouted, “Shut that fucking door and get back in here,” keeping the lilt in my feminine voice as best I could.

He turned to look at me, more frightened than confused. What the hell was I saying? Doing? Yelling at this poor man with another man’s cum still plastered to my face? 

“I let him shoot his load on my face for the sake of the video. But I really wanted him to cum inside me.”

He turned back to the door as if to flee. 

“I want someone to cum inside me. You’re not leaving until you cum inside me. I don’t care if you’re embarrassed or uncomfortable or you think I look ridiculous. You are going to fuck me and cum inside me.”

And now I was peremptory, I wasn’t asking, I was commanding. “You are going to take those pants back off and let me take your cock into my mouth and when I’ve gotten you nice and hard, you’re going to fuck me in whatever position you like. I’ll let you choose how, but you ARE going to fuck me. And when you feel like you’re going to explode, you’re not going to pull out and get it all over my pretty dress and panties and stockings and you’re not going to straddle my face and shoot your hot load into my mouth. No. You’re going to just go on thrusting until you cum inside me. Clutching my ass the whole time until your emptied cock goes soft in my ass. And you’re gonna leave it in until I say you can take it out.”

He looked at me for the first time since I’d greeted him at the door, then looked back down at the floor, seemingly seized by a moment of fight or flight. The silence was getting awkward and I was losing my nerve, but I firmed my resolve and cut through the tension with, “And as you could see, I like to be spanked.”

At that, I motioned him to the bedroom as I strode back in with uncharacteristic balance on the pumps, even swaying my hips a bit like a starlet, lifting my dress to show him what he might be missing from behind. I knew I was giving him an opportunity to escape, but felt the situation called for bold strokes, as it were. I sat down on the bed and waited. And waited. The door did not open, nor did his footsteps approach. 

I’m not exaggerating when I say that I waited like that for a full twenty minutes (or maybe it only seemed that way), with the movie star’s cum crusting over my lipstick and droplets still dampening the bodice of my dress. There were even a few drops on the floor I’d missed. With great restraint, I refrained from licking them up, for fear the cameraman would walk in at that moment and start laughing at me again. And so I just sat there waiting. And waiting. 

And then he walked into the bedroom, eyes on the ground. Stood above me, looking away. Unzipped his pants and let them drop to the floor.

It was literally the hardest cock I had ever seen. (Though not quite as big as my co-star’s.) The hardest cock I had ever subsequently (immediately) plunged into my mouth, sucked, grazed, slurped, slapped my cheek and chin and forehead with, deep-throated until I gagged. The tautest balls I’d ever licked and kissed and nibbled. The most terrified, besieged whimpers of discomfited pleasure I’d ever heard while doing so.

And when it came time to fuck, I refused to let him off the hook and fuck me from behind, going back on my word of letting him choose the position. No, he was going to face me. I went to my back, pulled my drooped stockings up, spread my legs, slid the crotch of my still wet panties aside and began to guide his cock in as I looked up at him: challenging, insisting, almost menacing him to look at me while he fucked me. 

He assented with his hard cock, probing as my previous lover had what seemed like hours ago now, but still, he refused to return my gaze. My somewhat sore, but still scintillated ass received his cock, and I whimpered up at him, almost begging him to look me in the eye. He returned my whimpers with his own hurt animal sounds until they transformed into grunts of extreme pleasure, and I could tell he was going to cum right away. At this point, it occurred to me that I might be his first. That maybe he had liked to watch, but had not yet had the courage to... participate?

“You gonna cum for me, baby? Look at me, baby. Look at me while you cum inside me. Look at me, sweetie.” I felt him trying to pull out and grabbed his ass with both hands forcing his cock back into me. “Don’t stop. Don’t you dare stop. Let go, baby. Come on, sweetheart, look at me while you cum inside me. Say my name while you cum inside me!"

And I jerked his right arm so that he lost his balance and came down on top of me. Face pressed into the pillow beside me, his five o’clock shadow having abraded my cheek, and I could now feel his hot breath on my neck. His cock had slid out in this motion, and he reached down to put it back in. Thank God. (I thought I had given him the opportunity to flee.) He held himself up with his right hand, his left hand pressing back my thigh where the garter belt clipped onto the stocking. And as it reentered my anus, the cumshot was instantaneous. Another too loud (way too loud) groan emerged from me and met his overwhelmed yelp. I could feel the first moist release, and I clutched his head with both hands staring him dead in the eyes, which he finally met with a grimace. 

“You’re cumming inside me, baby, you’re cumming inside me,” I informed him, though he was surely aware of this fact. I just wanted it to be made known, so I groaned it again, articulating each word, “You’re cumming inside me,” so loud the neighbors could not just hear me, but make out every word. 

I groaned louder, and he grunted louder and shot a load into me that was oozing out and down my ass long before he was done. The orgasm must have lasted two or three minutes (I’d be wiping his cum out of me for days). Thrust after thrust after thrust. Groan after groan after groan. But it just kept cumming. I held his face in my hands as he shuddered and pumped out a last squirt of cum. 

Exhausted, he finally pulled out and lay next to me on the bed. I almost chastised him for not waiting until I said he could take it out, but didn’t want to frighten him off. I wanted to roll over and kiss him and tell him I was falling in love with him, but as I say, I know how guys are after they’ve shot their load. I could barely move from exhaustion and the orgasm’s aftershock, but managed to slide down to where his limp cock was still oozing cum. I cleaned it off, sucking the last few drops out despite the tang of my ass, held the cock (beginning to harden again, just a bit) in my hand, and stated the obvious, “That was wonderful, sweetheart. That was fucking incredible.”

He wouldn’t look at me again, and I could see he was mortified. He quickly dressed, grabbed his backpack, and was out the door in less than a minute. I turned to the window and saw him traversing the walkway. No one was around, so I called out, “Thank you, lover! CALL ME!!!” 

But he dropped his head and hurried off. And I murmured “come back to me, baby” in his general direction, releasing a deep, satisfied, lovestruck sigh.

……..

The first part of the video can be viewed on the site, just type in Monica Cheeks. Unfortunately, there’s only audio of the second session. He’d left the camera on. Trained on the half-shut door of the bedroom. But you know exactly what’s happening at the climax because I play-by-played it.

You’re cumming inside me.” I told him and you can hear me telling him and imagine it happening.



Published 
Written by Monicalove96
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