Helping a Dear Friend (By Sucking)

Tags: Blowjob, crossdressing, gay, oral, reluctance, friendship

I posed in front of the mirror and flaunted my outfit to the reflection. My red ribbed high neck crop top meshed well with my black skater skirt and the thigh high socks were icing on the proverbial cake. I shifted my heart shaped spiked collar and licked my lips like a newly minted onlyfans model.

I was having a great time enjoying my new fem clothes, especially in the new red lacy thong I had recently acquired. It fit so well against my cock and I loved how it looked with it hugging my ass too.

I lifted my skirt and fished my cock out of the lacy black panties and started to stroke my cock slowly. I let out a soft moan as I stared at my painted nails against the throbbing erection.

Sadly my fem session was cut close as my phone on my bed began to buzz several times. I rolled my eyes and picked up my phone lazily and furrowed at the screen.

I had known my best friend Zane for more than a decade, from high school to college. He was the ultimate bro, in the best way possible, he was super friendly, kind, and overall a sweet guy. He was one of the only people who knew about my penchant to dress enfemme.

But if there was one thing you could say for sure, it's that he had the worst luck with girlfriends. Seriously, he had been cheated on, broken up with, and ghosted by almost every girl he had met. Which was crazy, the man was quite attractive. Zane was a footballer so he was a 6'2, milk chocolate, amazing abs, and a blue eyes black hair legend back on campus.

But sadly as I had expected a month ago I let out a large sigh and prepared for the onslaught of depression.

"Hey bud, everything okay? You don't usually call unless-"

"Yeah, Mary-anne broke up with me. It fucking sucks dude." he interrupted me abruptly. His voice was both wavering and low.

Mary-anne was probably my least favorite girlfriend of his, a total liar and a piece of shit overall. Plus I'm pretty sure she just stole my punk aesthetic and clothes several times. It was another note in a long line of an alphabet of failed relationships.

"Listen bud, why don't you come over we'll get high and shoot the shit man." A long silence held between us. I could hear the gears turning in his brain slowly mixed in with the sniveling of his cries.

"Yeah I'll be right over. Be there at 10." I hung up and looked in the mirror, I didn't really have any time to get out of my fem stuff so I dug out a few joints from my nightstand and grabbed a lighter.

Zane blew a puff of smoke in the air and slumped further into the sofa chair, I watched sadly as he dragged his hand across his face to try and rub off his depression and unfortunately it was not very effective.

"Fucking unbelievable!"

Yeah there it was. I laid down on my own sofa looking up at the ceiling and took a drag of my joint.

"I know buddy, so what did the bitch even say in the first place?"

"Hey don't call her that. She broke up with me cause she had to go back home in Wisconsin suddenly and she just said she felt like she couldn't continue the relationship." He rambled on so quickly that I caught every other word.

I sat up and held the joint in my left hand and did my best to look apologetic.

"Sorry mate, I really am, I'm just defending your ground I am." Another drag of my joint and I brushed my skirt down and blew looking up at the cieling.

Zane groaned and held his head down, he scratched his neck like a beaten down dog.

"Yeah, I know man. I'm lucky to have you as a true and blue mate." He blew out a ring of smoke and he ashed out. "It's just I'm just so frustrated" he huffed out in anger.

"I bet, I know you'll find some girl eventually. You were always the crown prince of our college" he looked...bothered from my attempt to reassure him. I snorted and watched as he pitifully looked down.

"Yeah but dude, she had me like..." his voice hushed to an exaggerated whisper, a sign he was truly high. "Edge, y'know, I haven't done the thing in awhile."

I let out a chuckle and rolled my eyes. "So what, a day, two, a week, a-"

"Two months."

I swear you could see my slack jaw from outer space. My friend, the deadly handsome lady killer that was Zane, was more than pent up.

"Holy shit dude how have you not exploded. Or even masturbated yet? Shit I hate the girl you fuck next!"

He got uncomfortably silent after that and I could tell something was causing him to shake his large leg restlessly.

"None of my exes are in town and I just don't wanna see anyone and... I tried masturbating but I can't seem to y'know?" He mumbled so I barely heard him but I felt everything he was saying. The man was blueballed for months!

"Shit dude, wish I could help but I don't have any of my friends that are single." I shrugged apologetically and put my hand on his shoulder gently.

I was about to pull away and just as I was, his hand shot back to grip my much smaller wrist. He stared at me straight into my eyes with his dark brown eyes. I was so startled that I couldn't move and just let him try to explain himself.

"Hey, so listen, you've been a great friend to me so please don't freak out about what I'm about to ask you?" I nodded my head slowly and his hand on my wrist squeezed gently.

"I really need you to suck my cock."

What.

"What." I may have well become as flat as Florida.

I tore my hand away from his wrist and glared at my obviously joking friend.

"Zane, seriously dude? This is such a dumb joke." He shook his head while rolling his hand through hair.

"I'm being serious dude, I can't fucking get off using my hand, haven't had any luck with any girls. I wouldn't ask you if I didn't need it. I'm begging you, no one has to know and it'll just be this one time, I promise." Each word felt like getting pelted by a meteor straight to the head.

"Bro." I groaned trying to pull my outfit a little more down just to cover myself more.

"Like, you're my friend but you're asking for a fucking lot. Plus you know I'm a top, you remember how I fucked that douchebag fratboy Nigel at that party. Like why me anyways, you could always go on grindr or something?"

I heard him gulp audibly and I glared even harder into him, doing my best America impression by digging into his soul looking for oil.

"Yeah, that frat boy bit off more than he could chew. And I know you're a top but you always dress like a sexy bitch. I don't trust grindr, you're always complaining about how shitty it is." Outside of the compliment I could see where he was coming from, Zane had heard many a rant about my exploits on grindr.

"So I get that this is weird but please dude, you're my best friend and I wouldn't ask you this unless I thought it was important.

So here we are, me, 'dressed like a sexy bitch' being asked by his best friend to suck his cock.

Best. Friend.

This was a guy who would take a bullet for me. A straight guy who has been my friend for more than a fucking decade. And he's asking for me to suck his cock and cum. He wouldn't ask this unless he was absurdly desperate and my mind battled with that he was asking for one measly blowjob.

The silence bloomed in both length and uncomfortableness. The clock in the room slowed to such slowness that it could have quit its one job to record us for a shitty endless podcast.

I turned away looking at the mirror to my lift and gave myself a once over on my outfit. Every single piece of clothing felt skimpy and slutty, high crop top left my curvy hips to my skirt which barely covered my ass and left no room for imagination.

Fuck me. Here we go.

I groaned in exasperation and pushed the palm of my hands against my eyes.

"Fine." Was the only word I could let out with a hiss through my teeth.

"Wait seriously?! Cause dude I'm genuinely serious about this." At least he has the gall to be a little skeptical about this. I put my hands on hips and gave him the most judgemental stare I could muster.

"Under much deliberation from the council dick. I honor you one goddamn stupid ass blowjob. So we can do it behind a blanket or something."

His astonishment over the acceptance of his request was almost worth it.

"Thank you so so so much. Trust me, no one will know and and I will do anything for you. But yeah, uh I kinda like to look at the gi-person while we do it. Plus you look pretty sexy in that skirt.

"Flattery ain't gonna get you anything else. This is a one time thing. So just get on the couch and we can...start." My harsh tone did let him know about my obvious disdain.

Awkwardly he plopped on the couch and zipped down his zipper. If this was a porn it would be a really fucking sad one considering how slow and awkward it was.

His hand found its goal and with an awkward grunt he let me see what was about to be in my throat.

I stared at my friend's cock with intrigue? At half-mast it was at least a 6 inch cock that was rather thick, it was definitely close to my own and was throbbing lightly to the beat of his heart. Zane himself looked away, suddenly fascinated by my apartment exit.

I felt like a moth to a raging flame as I walked forward, gazing at my future guest in my mouth. I stood in front of him and brushed the skirt down a little bit along with pulling up my thigh highs. Poor guy probably wouldn't want a view of my own cock so I'll spare him the details.

I slowly crouched down onto my knees and due to our height difference on the couch, I was facing face to face against my oral enemy.

"Hey dude, I'm sorry but can we like hurry along? This is torture..." he still couldn't look at me straight but I felt the urgency in his voice, a sign from his imposed chastity these past couple of months.

I rolled my eyes and spread myself to a more comfortable position. I let my hand rest gently on his muscular thigh and took an iota of pleasure watching him squirm.

But here we were him with his cock half hard and me dressed like a sexy bitch about to suck said throbbing cock.

Our eyes both met as I glided my hand on the warm shaft and I felt it grow another inch as I started to stroke it up and down. Zane let out the softest of moans but I ignored it to continue on my quest. His shaft was thick and I used my other hand to trace the vein down his growing tower of a dick. Unconsciously I quickened my pace and took in how hard he was getting. Pre-cum started to roll down the slit of his cock down to shaft which dripped onto my hand,

"H-hey, can you stop teasing please?" I snapped out of my cock hungry stupor and stopped stroking to take a final look at my handiwork. His rock hard dick would dwarf most people's dreams and I was wondering if the reason why Mary-anne broke up with him would be the size of this thing, it's astonishing how much pleasure I was taking from this, feeling the hot attraction in my hand and watching it throb with excitement had awoken something in me that I hadn't felt in a long time. Worse was I felt my own cock angrily revolt against the lacy panties, threatening to break if it didn't get used soon.

"Y-yeah, one sec." I brushed my hair out of my face and decided to give in to fate, although not without a little tease first.

I lowered myself down to the bottom of his shaft and I made sure that he could feel my hot breath every inch of his gorgeous cock. I smiled in satisfaction as I heard him mewl from both pleasure and frustration, I lowered myself just a little further and let my hands explore his muscular thighs.

I was about to extend my tongue onto his shaft and just adored how he flinched in anticipation over the promised oral, but I couldn't leave it there so I gripped Zane's future invader and looked into his eyes as he got harder and whined from my stalling.

"Hey Zane?"

He looked down with a look that mixed confusion, frustration, and horniness.

"Y-yeah?"

I gave him the most evil grin I could manage, a look that would have made any fucking cartoon villain jealous.

"God, you're so fucking hard and so desperate, but I need you to beg for it, beg for my mouth." It was a cruel request but he was about to receive equal compensation for it. I saw him whimper and bite his lip as he tried thrusting his hips upwards, the cock hitting the side of my cheek.

"P-please, I need your mouth, I-I need you!" I gave him a sweet smile and bent down further to the bottom of his shaft. I kissed the tower of a cock and watched it throb in response as well as the hiss of pleasure from Zane's mouth.

I laid out kisses from his shaft and moved myself further up with every kiss, about halfway I started to grind my tongue onto the cock. The vein of it fought back with every touch of my attack, his cock somehow grew even bigger. A smell of sweat and precum hit my nose violently and filled me with a sense of pride of what I was doing to my friend.

Zane was biting down his knuckle, trying not to cry out in pleasure and squirm against my touch. At the same I felt my own erection through my panties and saw it jut out from the skirt, stealthily I fished it out of the lacy material and held it in my hand as it grew and pulsated.

I dragged my tongue all the way to the top of the cock in front of me and used my tongue to massage his head.

"P-please..." Zane's face was one of just pure exhausting pleasure. I was expecting him to be sensitive but judging how the precum had hit my tongue and let it string from my mouth to his cock, he was loving this.

And I was too. I started to stroke my own cock slowly as I continued to tease his girthy cock. I grasped the cock tightly which elicited a sharp moan from my friend and another throb from his groin made it feel so warm and firm. I circled the cock again with my tongue and in a slow motion I engulfed the head, looking straight into his eyes as I did. My tongue swirled around the head tasting the saltiness from his precum and let his member push forward into my mouth.

I engulfed the cock further, inch by inch I took more of his shaft as it raged in my mouth, begging for release. I bobbed my throat with his cock and didn't let him pull out with a tight grip of my lips, his precum was becoming addicting and I was starting to leak underneath my skirt too. I stroked my own erection at the same pace I was sucking him, each time that he would moan or hiss in pleasure I would grip my cock with the same fervor.

Despite my what I would consider 'expert blowjob skills', I still couldn't get Zane to cum with my mouth taking a majority of his cock, so desperate measures time. I gazed straight into his eyes again, warning him that what I was about to do was something that was going to be intense.

I flared my nostrils and took a deep breath through my nose and push down on his fully throbbing cock and hit the back of my throat. I fought the urge to gag against the huge invader in my throat and focused on taking it in full, and with a final push.

"Ungh-" Fuck it was hard, but I finally got all the way down to the base, my throat filled with his shaft and head, I felt it struggle against the vice grip that held onto his cock. Zane couldn't handle it and let out a loud gasp as I massaged his shaft inside my throat, I withdrew my mouth to the top of his cockhead, a trail of precum and drool trailed down my mouth and chin.

Just as I was about to release his head and take a breather for the next part of his favor I felt a large hand grazing against my hair. I paused in confusion and was about to look up when I felt his hand grip the top of my head and held my mouth to his head. I looked up again into his eyes with a small tear in my eye, a gauge of how much effort I was putting into pleasing my friend.

"S-sorry but-"

There was no way he was about to do what I think he was about to do, I found myself fighting against his monstrous hand held against my scalp, gripping some hairs. I tried making him cum so I would be free from my friend's constraints but the only thing I was succeeding at was making him moan and get harder as my tongue swirled around his raging dick.

My eyes widened as I felt a great sudden pressure on my scalp, preventing my escape from Zane's manhood. Oh fuck.

I placed my hands on his thighs and held on tight and with Zane letting out a guttural growl I felt my head shift without my permission and I took his length back and forth in my mouth. I tried voicing my concerns but they were met with the sound of the cock thrusting into my mouth and Zane's ecstasy.

As the taste of his cock pistoned in my throat I whined and winced everytime his thickness hit the back of my throat. Despite my position and my inability to separate our bond of friendship (read: gigantic fucking cock in my throat), I wasn't going to say that this was the worst position I've been in.

And my own hardness in my panties tenting the skirt was proof enough of my own enjoyment. With every push and thrust of my new oral friend in my throat made my cock thicken and bounce, caressing it by the fabrics.

I let out a huff of satisfaction as my eyes rolled up and tears began to stream down my cheeks. I saw Zane close his eyes and used both of his hands to grip my head and shove himself in and out of my mouth. I could feel precum leaking out of the skirt and drops of his own cum dripping on my crop top.

I rebalanced myself and spread my knees out further, I grabbed my own cock and began to stroke it to the rhythm of his thrusts. My own erection was throbbing in my hands and every time I felt his cock hit the back of my throat my cock would let a little more pre cum.

Every second he was getting closer to cumming and so was I.

"I'm going. I'm going to-" Zane, not knowing anything about blowjob etiquette was about to gift me a free dinner with the main dish being shot into my throat.

I stroked myself faster to match the pace of Zane and mewled as a familiar feeling took over my body. My cock erupted with cum drenching the hell out on my skirt.

While I was fixated on my own orgasm, I tasted my fruits of oral labors as Zane let out a guttural roar of completion. His cock throbbed so hard against my tongue until I felt his whole body tense up to my efforts.

His whole body spasmed and his erection exploded a violent stream of cum that filled my mouth and throat. My previous oral skills were not prepared for the rush of his cum and some of it leaked out from the corners of my lips.

Free at last I pushed Zane away and reluctantly swallowed the lingering gift my friend gave me. The viscous substance dripped down onto my skirt, wet with my own cum. Unconsciously I licked my lips as a foolish attempt to wipe my face but I sat there, on my knees, cum all over me and my throat, in front of my high ass friend who had a dazed smile on his face.

I stood up after realizing what just happened, sticky and furious, and gripped Zane's shirt with my fist.

"Hey asshole, what in the fuck was that?" I shook Zane so hard that he was practically a rag doll. Looking in the mirror I saw how my face, top, and skirt were flush with his favor granted. I sighed still holding Zane who at least was trying to regain composure, Great now I look like a girlfriend who's getting mad at their boyfriend.

"H-holy shit, I'm so sorry. I just kinda lost it and y-your mouth was so good. I didn't-" I let out a harsh exasperated groan, glaring at him and gestured to the outfit.

"What are you gonna do about this Zane, this shit is not easy to clean! Plus my jaw hurts like hell and I'm pretty sure I just got breakfast, lunch, and dinner down my fucking throat!" I ranted at Zane who squeamishly backed away from my enraged form.

"And, And, A-And." I sighed, letting the anger fade to a low (medium-low) simmer. I let my shoulders roll back and leaned against the wall, I rubbed the sides of my temple, grumbling over a sore jaw and a ruined outfit.

"H-hey, I'm really sorry, I'll get you a new outfit and I'll clean everything up, I'll grab dinner and stuff." God damnit, It was so hard to get mad at Zane when he was genuinely sorry and got cute like that plus I was the one who could have stopped at any time.