A Unique Backstage Encounter
My hand came crashing down, slicing my pick across the guitar strings as I belted out the ultimate chord of the penultimate song of the night. The fading boom from the sound system warred with the rising cheer from the crowd as I gazed out over their screaming faces. On any other night I would have spared a little attention over the entire crowd, but tonight I was drawn to one pair of blue eyes in particular.
She was demure rather than brazen, politely clapping with a soft smile instead of punching the air and screaming her head off like the rest. But what she lacked in outward enthusiasm, she more than made up for in her eyes. In spite of their cold ocean-blue color, her eyes burned with an unmistakable passion, enhanced by the way she fingered the pass hanging around her neck.
I’d first noticed her in the crowd five concerts ago, in Manehattan. She was one of six, make that seven, young women I’d known in high school. If not well, then at least by reputation, they’d been prominent in a series of rather infamous incidents. I’d heard in passing that she in particular had moved to the big city in order to be closer to the heart of the fashion business, so aside from tickling my memory, her presence hadn’t been particularly noteworthy at first.
When I spotted her the following nights in Whinnypeg, Vanhoover, Seaddle and Las Pegasus, I knew it had to be more than coincidence. Our last tour stop was in our old hometown of Canterlot and, no surprise, her name showed in the sales roster once I’d bribed the venue manager to get a look at it. Another bribe ensured that her ticket had been upgraded to a backstage pass.
I stepped back up to the microphone, my fingers strumming the slow, opening chords of our final song for the night. We usually ended on something fast and hard, but tonight I’d convinced my bandmates to end on a power ballad, slow and romantic. I caught her beautiful blue eyes again as I started to sing and kept her lidded gaze through the entire song. My thoughts drifted off to my dressing room, and I wished I could cancel the autograph signing that I’d have to sweat out before I got there.
I let out a sigh as I finally closed the door of my dressing room behind me. I shook my right hand, slightly sore from both playing a dozen songs and signing posters, albums, arms, and even a couple pairs of breasts. I stared at my hand, flexing my fingers as I wondered if his services would be needed tonight. Normally there was no shortage of groupies, eager and willing to get a little action, but the woman I’d implicitly invited to visit me had much more class than that.
My performance outfit quickly hit the floor as I stripped out of it and reached for a can of body spray. I had no time for a shower, but the venue was well air conditioned and my outfit breathed easily. A little fresh scent and fresh clothes from inside out made me presentable just in time to hear a knock at the door.
Of the seven famous (or infamous) young women I’d known years back, two especially had caught my eye at different points, but I would have welcomed a visit from any of them, not least of all the one now standing in my doorframe. She was wearing a blue and gold dress that matched my skin and hair, but it was low and short, showing off quite a lot of her pearl white skin as well.
“Rarity, come in,” I said, holding open the door for her and sweeping my hand toward the sofa. “Have a seat.” I could smell her perfume over my body spray as she walked past me and I snuck a glance down her dress. She was showing off, so I thought I’d enjoy the view, even if I wasn’t going to be getting lucky.
“Thank you, darling.” Rarity had a way of making anything she said sound sultry. She sat down on the sofa, crossing her long legs and adjusting the hem of her dress.
“Drink?” I asked, indicating the collection of half-filled bottles lined up on top of the mini-fridge. “Anything you see, or I can send out for whatever.”
She eyed the selection, mostly hard liquors. “I usually prefer wine, but we don’t wish to be disturbed, now do we? I see gin and vermouth. A martini will do nicely.”
We don’t wish to be disturbed. I felt a throb in my pants as I mixed our drinks, her words echoing in my head. I handed off her drink as I sat down beside her, not too close, but still on adjacent cushions.
We caught up on old times, sipping our drinks slowly. Her contracts and contacts in the fashion world and beyond were many and varied, and we even shared a few in common. She inquired about my career even as I asked about hers. Neither of us mentioned her attendance at my last few concerts, though we both knew it.
Her eyes lit up in amusement as I asked about her friends. I tried to sound equally interested in all of them, but she saw right through me, and knew who I really wanted to know about.
“Twilight still visits on occasion, but she spends quite a lot of her time with Sunset these days.” Rarity chuckled, covering her mouth as she did so. “They think it’s their secret, but even Applejack has noticed.”
I felt her hand caress my shoulder, her neck craned to look me in the eye. “You’re not still pining for them after so long, are you?” She smiled, gesturing toward my performance outfit, now hanging up. “You seem to have your choice of female attention these days.”
“No, not really,” I said, sitting up straight. “But it’s hard not to think of the ones that got away, especially when something reminds you of them.”
“Oh.” She gave a soft gasp. “Yes, I can understand that. Perhaps not in love, but the fashion industry is rough, and I don’t always land every contract I set my sights on.” She pursed her lips. “Speaking of, perhaps I can offer a distraction.”
“Huh?” Whatever it was, I already felt it working.
“Well, I didn’t wish to take up our time tonight talking business, but in view of the circumstances perhap I should.” She opened her purse and pulled out a small photo album, handing it to me. “I’d like to expand my business a bit more into men’s fashions, you see. Not just the suits and formalwear I do now, but flashier items as well.”
I flipped through her album as she spoke. The first couple pages were of well-cut, but drab suits, boring business stuff. But flipping through a bit more, I started to see more colorful outfits. Casual, tropical-themed styles, playful parodies of business suits in wild colors, and beachwear from moderate to flamboyant and possibly against public conduct laws on most public beaches.
“In order to be successful, though, I need advertising, and of course models.” I looked up in time to see Rarity batting her lashes at me.
“Me?” My voice hadn’t cracked like that in years.
“You, darling.” She smiled, taking her album back and flipping through it herself. “Naturally, we’ll have to have our agents and such haggle over the details, but I believe we could help each other.” She drew my attention back to my outfit hanging up in front of the wardrobe. “Your present ensemble is certainly nothing to sniff at, but variety is always nice. I could design a few additional outfits for you and your band, which would get my name out in your circles, and you could model some of my new line, which would get your name out in my circles.”
I felt her fingers drifting over my chest and looked down to see her straightening my buttons and adjusting my collar.
“As a personal touch, perhaps I could design a few things for your everyday use. These off the rack clothes are adequate, but they don’t flatter you much.” She scooted closer on the sofa and I felt her breasts press up against my arm as she held out her photo album. “Something like this, perhaps?” Her finger traced across a picture of a guy with skin about the same color as mine, dressed in a two-tone blue shirt that reminded me of Vinyl Scratch’s hair. His shirt collar dipped low, showing off a bit of his chest.
“All your stuff looks pretty sweet,” I said, catching Rarity’s eye. “My agent has a vacation lined up as soon as this tour is over, starting tomorrow, but I’ve got some money to burn. I might as well get some nice clothes, and then we can start talking about the rest when she gets back.” My only experience with modelling so far had been impromptu sessions with Photo Finish and her henchwomen back in high school. Rarity didn’t strike me as quite that manic sort of person, but it couldn’t hurt to have a few days to check out her style.
“That sounds wonderful, darling.” She slipped her photo album back into her purse and pulled out a rolled up measuring tape and small notepad and pen instead. “If you’d like, I can take your measurements now and get started on some designs right away.”
“Sure, alright.” Her arm was still brushing against mine and her batting eyelashes seemed more than eager, so I agreed. Besides, I wasn’t about to pass up an opportunity to have Rarity put her hands all over me.
I stood up and offered Rarity a hand, helping her to her feet. She let her fingers brush my shoulders as she walked toward the door and locked it. I raised an eyebrow and asked why.
Rarity smiled at me. “We can leave it unlocked if you wish, but to take your measurements correctly, I’ll need you to take off your shirt and pants.” She winked as she walked toward me again and toyed with the buttons on my shirt. “Most people like privacy, but maybe you’re the exhibitionist sort.”
“Privacy is good!” I chuckled nervously, starting to unbutton my shirt. “So, just my shirt and pants?”
She tsk’d at me, but she was still grinning as she unrolled her measuring tape. “Unless you’re wearing long underwear that should be enough. Start with your shirt so I can get your chest and arms, then we can work our way down.”
Rarity walked behind me as I pulled my shirt off, and I had to suppress a moan. I could feel her breasts press against my back as she leaned in to wrap the tape around my chest, covered by her dress below, but bare on top. Her fingers brushed my chest more than was probably necessary and I bit my lip. I’d have to take off my pants in a minute and I wasn’t sure how she’d react to a fully pitched tent.
I got a little bit of a break as she measured my arms and stepped back to jot down the numbers on her notepad. I took a deep breath, thinking about a cold shower and I felt my growing erection relax.
“Now I’ll need you to take off your pants, darling.”
I peeled down to my boxers, glad that I wasn’t showing any obvious arousal, but keeping that up (or down as it were) suddenly became much more difficult. As soon as I stood up, Rarity dropped to her knees and started measuring my waist and legs. Even if I didn’t have a full view of her cleavage, her face was right near my crotch and I couldn’t help thinking that I’d usually be staring down at a cute groupie in exactly that pose by now.
I had my eye squeezed shut, trying hard to think of every frozen thing that I could when I felt Rarity poke the tip of my erection through my boxers. “Oh my, darling. I didn’t realize having your measurements taken was so exciting.” I felt her fingers trace the waistline of my boxers. “Or did you want me to measure that as well?”
Before I could say anything, I felt Rarity slip my boxers off and my hard cock spring free. I looked down to see her grinning, the measuring tape already wrapped around my erection. “Rarity, what are you doing?” I let out a moan as her fingers brushed my cock.
“Measuring you, darling. Four inches around, roughly,” she said, unwrapping her tape and laying it along my length. “That’s about an inch and a quarter wide, respectable without being destructive. And almost seven inches long.” She gave the head a little flick with her fingertip. “Such a nicely proportioned tool.”
I gave another moan as she stood up and circled me, pressing against my back again. Her fingers reached down and barely teased my cock. “You’d like me to do more, though. Wouldn’t you?” she asked, her hot breath tickling my ear.
I nodded.
“I certainly hope you treat your usual paramours well, but as a lady, I insist on fair treatment.” Her hand wrapped around my shaft, giving it a soft squeeze. “You have a very nice penis and it would please me to service it, but only if you’re willing to repay me in kind.”
“Deal.” I agreed. My usual groupies always seemed to be after a quick fuck, but it’s not like I didn’t know how to show a girl a good time.
Rarity’s hand left my cock just long enough for her dress to slip out of the way, leaving bare breasts pressing into my back. “I saw you staring at them earlier,” she purred, her nipples growing hard against me as both her hands now teased my erection. “Other women might see it differently, but to me being noticed is a compliment, thank you.”
She rubbed her tits against my back in small circles and softly jerked my cock while teasing the head until my knees started to shake and I thought I might cum. I staggered back onto the couch as she stopped just in time and let me go as she stepped to the side.
I took a few deep breaths to calm down as she knelt down in front of me, sliding her dress down to her stomach and cupping her naked tits.
She leaned in and planted a kiss on my cockhead. “Do try to last as long as possible, darling. When I put a penis in my mouth, I like to savor the feeling.” Before I could say anything, her hot mouth engulfed my cock.
I gripped the couch cushions, bearing down on my groin to hold back as Rarity slowly worked her mouth over my length, sucking as she pulled up and licking as she sunk down. “Oh fuck, Rarity,” I groaned as she blew me. Her lips stayed sealed tight, bumping against the flare of my helmet and tugging at it at the top of her stroke.
Once in a while, she bottomed out and I could feel my cock head poking the back of her throat as her tongue tickled the base of my cock and the top of my ball sack. I let out a groan as her hand came up and started fondling my balls, rolling them in her palm under my loose skin.
After all her earlier teasing, it felt too good and I couldn’t hold back any more. “Rarity, I’m gonna cum!” I clenched as hard as I could, trying to give her time to prepare for wherever she wanted my cum, but she didn’t move and I felt the head of my cock flare against her lips as I unloaded in her mouth.
I could feel her throat contract, swallowing my load as I slumped against the couch. She sucked softly, making sure I was drained before pulling off and smiling up at me.
“You could do with a little more fresh fruit in your diet, but your taste was certainly not unpleasant.” She stood up and turned her back, sliding her dress to the floor and showing off purple panties that matched her hair.
“I’ll remember that for next time.” I grinned, part of me hoping there would actually be a next time. I felt certain she wanted me to last longer than I did, and under less surprising conditions, I was sure I could.
“But in the meantime, I believe you owe me something.” She grinned at me upside down as she slid her panties past her knees and gave her hips a slight shake. “Just stay put, I prefer to stand.”
I was about to get up and offer my seat when she said that. As a result, when she stood up and turned around, I almost slid right off the couch.
Instead of a pretty white triangle with perhaps a patch of styled purple hair, I saw a patch of styled purple hair, but it was sitting on top of the base of a hard six-inch cock, white at the base, fading to a soft pink at the tip. “What the fuck?!”
“What’s the matter, darling?” She grinned, her finger caressing her hard shaft. “You promised you’d repay me. I gave you a blowjob, you give me a blowjob. Fair is fair.”
“But why do you have a dick?!” I couldn’t tear my eyes away from her crotch and the cock sticking out of it that she was slowly stroking.
“Because I do, darling. There’s a reason I let boys admire me from afar during high school.” She lifted my chin with a finger, breaking my gaze. “That wasn’t a very discreet environment and rumors would fly. But we’re alone here, no one would ever suspect anything from outward appearances.
“Only a select few people know, and none of them saw me come in here. To everyone else, I’m a beautiful woman and they’ll fill in the blanks with what they expect.” She grasped my chin with her thumb and tilted my head back down until I was staring at her cock again. “Men are always curious, but you’ve been conditioned not to act. Isn’t it wonderful that I’m offering you the opportunity to try it discreetly and with a lady at that?”
My mind swirled as I stared down the barrel of her gun. The word ‘curious’ stirred up old memories of finding my first porn on the internet as a young teenager. Jerking off just didn’t quite hold the same appeal after the first time I watched a girl putting a cock in her mouth. I licked my lips and felt Rarity’s hand run through my hair as I recalled figuring out just how flexible I had been.
I heard Rarity moan and felt her grip my scalp as I closed my lips around the head of her penis. My heart beat hard in my chest as I tried to come to terms with having a cock in my mouth. As a teenager it had been thrilling, but uncomfortable because of the contortions involved. Despite the fact that this was someone else’s penis and that was raising alarm bells in my mind, it felt a lot a lot more natural right-side up and without having to fold myself in two.
“Mmm, Flash. I knew you wouldn’t disappoint a lady.” Rarity put a soft pressure on the back of my head and I felt her cock sliding deeper in my mouth, the head rubbing against my tongue. With nothing left to lose, I tried running my tongue around the flare of her helmet. That had practically been a necessity to stimulate myself, so I wasn’t sure how it would work, but it did lead to more moaning from her.
I don’t know if it was her voice or if I was just in denial about enjoying dicks, but the alarm bells in my head quieted down and I started to get into it. I grabbed her ass and sucked on her cock as it slid in and out of my mouth, and dammit, I liked it. It felt like the oddest cross of eating a banana and sucking on a really warm, but unmelted popsicle, except for the way it throbbed in time with her moans. There really wasn’t anything bad to say about it once I really got going, it was almost comforting.
“Oooh yes, darling. Your reward is coming, so don’t you spill a drop.” Both of Rarity’s hands gripped my head as her cock started to throb harder in my mouth.
With her holding me in place, I knew there was no escaping, so I just sucked her cock harder and pressed my tongue against her firmly. When I had my own cock in my mouth, I had the same sort of non-choice. Trying to get unfolded without losing all my progress would have been too tough, so I just bit the bullet and came in my mouth. I remembered it was warm and gooey.
Rarity’s cum was also warm and gooey, and actually pretty sweet. I felt her pull back and bump her flared helmet against my lips as she started pumping her cum all over my tongue. I tasted my own a little when I was younger, but I always ended with my cock head near the back of my throat and just swallowed most of it straight down. Rarity gave me quite a mouthful.
“Oh, Flash. That was so nice,” Rarity purred, running her fingers through my hair while her cock finished unloading. “Swallow if you must, but I just adore kissing my lovers with a fresh load of my cum still in their mouth.”
I didn’t have to be asked twice and tilted my head back as she pulled away. She leaned down and slipped her tongue into my mouth, dipping it into the pool of her cum. I reached a hand up to her tits, fondling them as she sucked half her load from my mouth. We tongue wrestled for a bit as I slid my hand down her stomach. I was already committed, so I didn’t hesitate to wrap my hand around her softening shaft.
It didn’t feel too different from having my own cock in my hand, aside from being backwards, and it made Rarity moan into the kiss. But I broke the kiss and involuntarily swallowed the rest of her cum as I slid my hand down farther. Instead of finding a pair of balls as I expected, I found a pussy. Puffy, wet, a little higher up than normal, and fitting right into the base of her cock, which seemed to have taken the place of her clit.
Rarity giggled as my fingers felt up her pussy. “I suppose I neglected to mention that, but it can be so difficult to break through your social conditioning sometimes.” She pecked at my lips, licking up a little of her cum that had dribbled out during our kiss. “Perhaps you’d like to couple with me, promising to bear in mind that I am still a lady, of course.”
I nodded without hesitation and she moaned as I slipped a finger inside, testing the waters. She really did seem to be a lady with just a few extra, inexplicable bits. And even those weren’t too bad once my brain shut up and just enjoyed it.
She dipped down a bit as I pulled my finger free, and I felt her slide her softening cock against my hardening shaft. I moaned softly as she wrapped a hand around both of us and rubbed our cock heads together. It felt a bit like I was siphoning off her erection.
Soon enough she slid forward, mounting the couch as my cock prodded at the entrance of her pussy. We moaned together as she sank down on me until her soft, but not completely flaccid cock rested against my stomach.
Rarity’s breasts pressed into my face as she rode me, so I sucked on them, which just added to her happy moans. Fucking her felt about like fucking any other girl who was good at being on top, apart from two things: First, the firm little patch inside where her g-spot should have been was anything but little and it seemed to set her off more than usual as my cock rubbed across it. Second, her slick cock rubbing up and down the center line of my stomach. As she grew hard again, Rarity leaned her hips into me, pressing her cock more firmly against my abs.
Eventually her cock head nestled into my belly button as if it belonged there. Just like with it in my mouth, I couldn’t really find anything bad to say about the sensation and I began to suspect that I had more than just a passing interesting in penises.
Rarity’s pussy began to clench down on me and my cock throbbed inside her, muddling my thoughts, but making me feel sure that I my enjoyment of pussies hadn’t diminished any under the circumstances.
“Nnnnnnnng, Raaaaaarittty!” I popped off of her tit and hunched back into the sofa as I blew a load deep inside her. She sank down and ground against my hips, trapping her cock between our stomachs as mine filled her with cum.
“How naughty,” she purred, bending forward to nip at my lips. “Not even a warning this time before you came inside me. You’re lucky I’ve taken precautions.” Her lips tugged at mine as she stood up, a dribble of my seed barely visible trailing down her leg. She turned and pulled a small bottle from her purse. “But I’ll forgive you if you keep your promise to remember that I am a lady.”
“Wha?” My mind was still a bit hazy, but something about that phrase seemed familiar.
She grinned, squirting something from the bottle onto her hand and then wrapping it around her hard shaft. It glistened when she released it. “A lady must insist on fair treatment. You filled me with your cum, now I intend to fill you with mine.”
Feeling her cock prod against my ass as she lifted my legs sobered me at once. At least the prospect of sucking her cock had seemed less far-fetched when I remembered experimenting as a teenager, but apart from scrubbing clean in the shower, I’d never so much as touched my backdoor.
Her hips moved slightly, keeping her stimulated and smearing a bit of lube around my ass, as she seemed to be waiting for something. I stared at her smile as she watched me from between my feet. Her seductive, half-lidded eyes blinked once, her full lashes fluttering and drawing me in.
“Okay.” I grit my teeth as she pushed forward, gently sliding her cock inside me. It seemed like a fitting end to such an odd night. I’d already sucked her cock and swallowed her cum and enjoyed both. Taking her cock up my ass couldn’t really make things any worse.
Her liberal use of lube let her slip inside pretty easily once she got past the initial resistance, and I had to wonder if she’d done this with many guys before or if she liked being fucked in the ass herself.
She leaned over between my legs and locked lips with me, soaking up my moans with her mouth as she started to thrust. I could already feel my cock hardening and rubbing against her soft stomach as she fucked me, and mentally ticked off another way in which I apparently liked dicks.
“Oh, it’s so nice to find a willing man,” she moaned, leaning back and angling herself so that her thrusts started rubbing against my prostate. “I’m going to fill you up. Let’s see if I can make you fountain at the same time!”
She grabbed my legs for leverage and thrust firmly into me, making me moan and making my cock jump each time. Her lips were pursed and her face flushed as I could see her trying to hold back, but after a moment it was of no use and I could feel her cock throbbing and pumping her hot, sticky cum inside me even as she kept thrusting.
As sated as I was from cumming twice already, her cock rubbing right against my prostate and feeling her filling me with her seed set me off with a loud, deep groan. My mind swam and my head spun and I didn’t realize how hard I’d actually cum until the throbbing of my pulse died down and I felt my own warm semen splattered in a line across my stomach and chest, chin, lips, and nose.
Rarity slowly pulled out with a wet pop and leaned in, licking up the line of my cum from my navel to my lips, her tongue pushing my own seed into my mouth. I didn’t feel like refusing.
I had to agree with her, I wasn’t quite as sweet tasting, so I resolved to ask the road manager to stock more fresh fruit during our next tour and made a mental note to update my grocery list when I got home.
“I think a shower is in order, darling. Wouldn’t you agree?” Rarity’s voice whispered in my ear before she stood up.
I was relieved to see that her cock didn’t look any worse for wear than mine, aside from being covered in much more mixed lube and cum. But a slight rumbling in my gut told me that a shower was certainly in order, perhaps after some other bathroom tasks.
“Yeah, go ahead and get the water hot, I’ll just be a moment,” I said, standing up and clenching.
“I understand perfectly, darling.”
I felt better standing under the hot stream of water with Rarity leaning against me, soaping up my chest as her tits pressed into my back and her soft cock nestled between my ass cheeks. Until an hour ago, I would have been uneasy about the second, but now it felt natural.
“You’re not trying to escape,” Rarity purred, her hands dipping lower to soap my stomach. “I take it you enjoyed that.”
I turned my head to kiss her as her hands moved lower still, soaping up my cock and balls. “You really surprised me at first, but yeah, I did enjoy it.” Her hand slipped between my legs, soaping up my nethers. “All of it.”
“I’m glad, darling. I hate having to resort to blackmail when an encounter goes really wrong, but even when they enjoy it during, I rarely find anyone who will stick around afterward.”
“So, do you only ever go after men?” I couldn’t help asking.
“No, not exclusively,” she chuckled, “but willing female playmates are much easier to find and keep.”
My heart thumped a bit at the thoughts running through my mind, but I also felt my confidence returning. “Suppose you met a guy who definitely liked girls, but also found out that he didn’t know that he liked dicks and kinda wanted to experiment some more to find out for sure?”
Rarity leaned into me a bit more firmly and wrapped her arms around my chest. “This guy wouldn’t happen to be someone I might be working with pretty closely with in the near future, would he?”
“He might be. He might even think that would make him more willing to experiment in modeling and in private.” I turned around, wrapping my arms around Rarity. Down below, our cocks pressed against each other.
“He sounds like a keeper,” Rarity said softly, tilting her head back.
“I’d like to think so,” I said as I leaned down to kiss her.
Author's Note
No, I don't know why Rarity has a dick either, she just does.
I blame derpibooru.
