The Guildmaster didn’t make a sound as he made his way to an adjoining room. His stride smooth and even — almost as if gliding, not walking. My body still humming from the kiss, I followed expectantly at his heels. Once he settled into an armchair, I found myself quite self conscious, searching around the room as to what to do with myself.
“Get on your knees,” he gestured towards the empty space between his thighs. My face heated up at the thought, scenes of a hundred-some ‘massages’ flashing through my mind. Licking my chapped lips, I did as he said, though my nervousness made it quite apparent that the entire situation was very much out of my experience.
“I think you know what I want from you next, don’t you kitten?” His fingers traced the side of my face, tucking loose locks of hair behind my ear. “How many times have you had to watch someone else do it?” My face flushed even deeper. I did watch — of course I watched. What started as curiosity quickly evolved into something further, stoking a burnishing heat in the pit of my stomach.
“… I lost count ages ago.” My gaze shifted sheepishly from his face, to the waist of his pants, and then back up again. Trying to still my breathing, I placed my hands tentatively on his inner thighs, noting the familiar brush of roughened leather under my fingers. Unsurprisingly, it seemed to be made from much the same material as the standard Guild leathers, but dyed black. I bit my lip as my hands slid upward, feeling an insistent and undeniably live firmness straining against its leather confines. Molding my hand tentatively in its shape, I committed it to memory as I rubbed the flat of my palm up and down. Most of the masseuses seem to have employed a similar kind of motion, though mine was no doubt clumsier and unpracticed. A hand wrapped itself in my hair as I fumbled with the fastenings of his pants, eyebrows knitted together in concentration. As the swath of pale, taught skin dusted with coarse, grey hairs came into view, I found myself leaning in, stopping myself short just in time. “I, um- I’ll have to touch you now.” It was a serious warning, but the Guildmaster only snorted in amusement.
“Yes, that’s the idea.” His fingernails scraped roughly against my scalp, though it was oddly comforting. “Get on with it before I get bored.”
That was all the warning I needed to shift the rest of his clothing aside, retrieving his length as if it were a priceless treasure. Cradling it in my sweat-damp palms, I had to force myself to not spend too long observing — memorising the path of veins which spread from base to tip, or learning the rhythm of his heart as it echoed in my hand. I pressed my parted lips where the base meets torso, breathing deeply of his heady, intimate scent. As the intoxicating musk swirled throughout my senses, I found my body moving on its own; meticulously laving every inch of skin as I made my way up his shaft, while my hand stroked what my tongue couldn’t yet reach.
“Good girl.” I let out the breath I didn’t realise I was holding as I felt Mercer relax in his chair. The encouragement only spurred my efforts, and soon his entire length was covered in a thin layer of saliva. My hands could now glide up and down easily, but I glanced up at the Guildmaster, nervous about what I’ve seen is yet to come. “You can take it slowly, for now,” he rumbled, voice lower than I’ve ever heard it. “… But I’ll indulge myself in that cute little mouth before we’re done.” His dark promise, rough and striking, yet leaving a warm resonance in its wake, like the fresh sting of a blade — it sent a shudder through my entire being as I let out a whimper, free hand clinging to his thigh. A thick, heady trance drowned out my thoughts once more, interested only in pleasing the man who has me kneeling between his legs.
Compliant, I began to ease him into my mouth, being mindful of teeth as I adjusted my position to accommodate the intrusion. I could hear a shift in his breathing, but it was too difficult to concentrate on any such observations against the heated mire stifling my senses. If I could, I would have studied exactly what and where served him the best; documented the subtle tension in his abdomen, and the tightening grasp of fingers as he received his gratification. Instead, I only managed to cling to his form, making short, desperate whimpers as my inadequate lips slid along his shaft.
“Keep using your tongue, like you were before,” I heard it as a rumble, deep within my core. His hand held my head further in place, giving me less room in between each stroke. “And take more of it in each time.” I hummed in acknowledgment, though it sounded closer to a moan, and in response he began to shift his hips in time with my mouth. As he maintained the pace it started to prove difficult to keep up, both my jaw and tongue starting to ache from the rigour. I had to keep going; I had to be good. Even as my knees rubbed raw against the wooden floor, and he slid further into my mouth than was ever comfortable, I had to persevere. I had to. Mercer didn’t seem to mind all the clear signs of my struggling to keep up — no, with each new strangled moan escaping my throat, he only plunged deeper into my mouth, and the tighter I clung to him for purchase, the further his nails dug into my scalp as he directed my head to suit his pleasure. Even if I could keep my eyes open I wouldn’t have been able to see anything, being held flush against his body as he surged unbidden into my mouth.
“Finally.” His growls were feral, each word punctuated by a vigorous thrust. “A woman—” His movements grew frenzied— “who knows..,” —each upward rush— “her fucking place.” —more savage than the last. A tremor went through his entire body as he pinned my head in place, a deep, guttural moan resounding heavily in my ears. As a thick, caustic warmth erupted in the back of my throat, I choked immediately. The Guildmaster would have none of it however, grip unchanging as his other hand rubbed the back of my neck. “Swallow it all, like a good little girl,” he purred, smooth honey coating the steel of his voice. Only once I had finally managed what was asked of me was I released, body quickly giving out as I slumped in his lap, panting and spent. Mercer played with my hair for some moments, combing it between his fingers as we both regained ourselves.
Eventually, I regained awareness of my surroundings. Did all of that just happen?
“Oh. Sorry, I’ll fix this up for you..,” I mumbled, re-fastening the Guildmaster’s pants. My voice came out hoarser than usual, throat tingling. Apparently it did happen. Was I supposed to leave now? That’s what generally happens after his massages…
“Hm. Maybe you’re not completely useless after all.” He cracked his knuckles before rising to his feet, gripping my wrist to pull me up with him. I winced as feeling returned to my legs, knees sore from remaining in the same position for too long. “Unless that was too much for you,” he added, noticing my reaction.
“No! No… it’s alright. It was worth it, I think.” I could feel my face heating up again as the evening’s events flashed through my mind. I wasn’t sure if I just imagined the smirk pulling at the corner of Mercer’s lip.
"I need you to go to Whiterun. Talk to Mallus Maccius at The Bannered Mare."
“Okay. I’ll just have to let Delvin know before I go…”
“I’ll tell him. He’s sick of you hassling him for work, anyway.” He is? I had always been treated so kindly by him — perhaps I’ve only been a nuisance this entire time?
“I…-Alright.” Maybe it’s for the best that the Guildmaster said something. I’ll have to watch myself from now on.
“I expect my coffee in the morning before you leave."
"Of course! I'd never forget it."
"That's my girl." He cradled my cheek in his hand for a few moments before turning to leave, disappearing into the shadows of the adjoining rooms. I could feel his warmth enveloping my still beating heart, comforting and stifling all the same time.