As a Christmas gift to himself, a young man makes good on an online flirtation.

M/transM with depiction of female bondage

Click the cover image to download MOBI, ePub, or PDF through Instafreebie, or keep scrolling for plain text.

If you like what you read, there's another free erotic short for subscribers to my email list.

Join the Rainbow Advent Calendar Facebook group to find more great stories.

Download from Instafreebie

The Observer

Despite my nerves, I was humming Jingle Bells as I strolled down the hall to Thomas's apartment. And why shouldn't I be feeling festive? This was my gift to myself, after all. After so many months of thinly veiled online flirting, I'd be seeing him in the flesh. I'd driven two hours for this. If I wasn't feeling festive then what the hell was I even doing here?

The place was nice. One of those shiny downtown gentrification condos, all brushed aluminum and mod carpet. Many of the doors I passed were decorated with evergreen wreaths or twinkle lights, but when I arrived at his number it was unadorned. I consulted my phone before knocking. No messages, no missed calls, so that should mean everything was going according to plan. For once I'd managed to hold up my end of things by being on time, which was important, because the whole thing had been planned to within minutes. Just as I was about to knock, the door opened and there he was.

In my experience, I can tell everything I really need to know about an online acquaintance the moment we meet in person. Either their physical presence supports and reinforces the connection we've already built, or it falls flat. That being the case, I probably should have arranged to meet him for drinks or a coffee or something first, but I had a good feeling, and if I was going to make the drive anyway there might as well be something more interesting than a Starbucks waiting for me at the end of it. The gamble was paying off. He was every bit what I'd hoped, and that sense of already knowing him hung there in the air between us. I could only hope that he was experiencing something similar, because this feeling could quickly become awkward if it was one sided. He was smiling in a way that suggested we were on the same page though, one eyebrow slightly cocked as he made his inspection.

“Were you having second thoughts?” His voice. A pleasant tenor. Maybe a little reedier than I'd imagined.

“Not at all.” Especially not now. “I just took a minute to check the time and... there you were. Can I come in?”

He waved me through the door. The apartment matched the design of the hall, a well lit studio space with one wall of floor to ceiling windows. It was made homey by a couple of shelves groaning with books and a nicely made bed in one corner. He took my bag, saying, “Marissa will be here in a few minutes. I thought you could observe from there,” he indicated an upholstered chair by the window. “She knows what's expected of her. You don't need to do anything but watch, but I'll let you judge for yourself whether you'd like to step in and be more involved.”

It was hard to imagine what I might do on the spur of the moment to “involve” myself. That need for split-second certainty was one of the reasons I was shy of topping. When, in the course of our endless chat threads, I'd confessed that I might like to see him in action some day, I'd been clear that I saw my role as merely a voyeur; but I appreciated the collegial trust he was offering me and acknowledged it with a nod.

I couldn't help but feel a little lost, standing there in the middle of the room wondering what to do next. I could take my seat and wait, but... Thomas caught my eye. “Doing all right?” What I really wanted was to explore that connection I'd felt in the doorway while it was still just the two of us.

“Yeah, just... come here and help me get my bearings.”

He left my bag on the bed and crossed to me, placing his hands on my shoulders. The pressure was grounding, reassuring, and I reveled in the warmth of his hands through my jacket. I took him by the hips and pulled us closer. He smelled faintly of cologne, something woody and aromatic, and there was a twinkle in his eyes that suggested mischief. He seemed to be doing his best to suppress a smile. “It's good to see your face. For real. Moving and emoting and stuff.” At that, his smile started to break through, and I rushed in to catch it on my lips. He met me eagerly, and I let myself get lost in exploring his mouth while my hands took in the topography of his back and buttocks. It wasn't the time for this, not really, but after fretting so long over a relationship that felt half-imagined, I needed to make it physical before our company arrived.

At that thought, there was a soft knock on the door. We separated, and the vibe in the room made an abrupt shift as Thomas collected himself and became suddenly businesslike, flipping on some soft opera music as he took up a thin, elegant cane and went to answer. For my own part, I smoothed my hair, gave my waistcoat a straightening tug, and took my seat, leaning back with ankle over knee and assuming what I hoped was an air of causal interest.

A young woman, Marissa, I assumed, was standing at attention just inside the door, eyes fixed on a spot of empty floor. She was wearing a long wool coat and very high heels, a lush red scarf gathered up against cheeks flushed from the cold. Had she walked here in those shoes?

“Coat off, shoes on please.” His voice was soft, gently authoritative.

Without taking a step, she lifted the scarf over her head and hung it on the rack by the door, then started on the buttons of her coat. My attention grew a little sharper as I realized that beneath the coat, she was wearing nothing. Thomas seemed unsurprised but appreciative, his eyes grazing warmly over her curves, echoed by a stroke of his cane. Applying light pressure at the small of her back, he herded her a few steps in my direction.

“This is our guest, Mr. M. He's here primarily to observe, but anything he asks of you, you should treat as if it were coming from me. You may bid him good evening.”

“Good evening,” she offered, her eyes flicking curiously to mine for just a moment.

“Eyes!” Thomas snapped, simultaneously raising a sharp welt across her buttocks with his cane.

“Sorry sir.” She resumed her focus on the floor, but with an almost imperceptible tightening of her lips that might have been a smirk.

I wondered what she thought of me. What she knew of this whole arrangement. I had dressed carefully, hoping to cover my uncertainty with dapper trappings, but I suspected that what Marissa saw in her fleeting glance was something other than the image of myself I'd cultivated in the mirror. Just as well that her attention would soon be elsewhere.

Thomas gathered a few items from a nearby table and walked Marissa to the kitchen counter, where he instructed her to stand perfectly still, facing the windows. He spent a little time taking her in: cupping her breasts, stroking her flanks, taking her measurements, it seemed, in a profound and intimate way, while she was forbidden any response. She really was lovely. I could appreciate a woman aesthetically, even if I wasn't particularly interested sexually, and could see why she might be a favorite for Thomas.

He leaned over to pick up a length of hemp rope and, finding his face directly adjacent to her breast, gave a quick and playful nip that elicited a sharp intake of breath from her, but nothing more. He eyed her, maybe looking for an opening for further discipline, but chose to move on.

He worked the line with skill and accuracy, his movements fluid as he measured, folded, and placed the first coils on Marissa's body. The rope seemed unduly course against her supple flesh and he drew it tight enough to turn her smooth silhouette into a series of undulating peaks and valleys, but she didn't flinch.

I felt myself suspended between the two of them as I watched -- mesmerized by the meditative precision of Thomas's actions but kept on edge by Marissa's extreme poise as she was encased throat-to-hips in rope. My hand moved to my lap and I began to stroke idly, teasing myself through the thin fabric of my trousers.

“Do you think,” Thomas began in a an offhand manner, as he knelt to hobble her legs, “that the neighbors across the way are enjoying the show?”

That got her attention. She swallowed. I could see her chest begin to rise and fall a little more quickly, and though her gaze stayed fixed on the floor, she was practically vibrating with the impulse to look out the window.

I, being free to move, did look. It had gone from twilight to full dark outside, and the blinds were wide open. Anyone paying attention in the building on the other side of the street could have seen what was going on in perfect detail. Just now, I could see someone preparing dinner and someone else engrossed in the TV news. It didn't appear that anyone was taking an interest in our little production yet, though.

I glanced back to find Thomas binding off the last of the hemp near her knees. She was cocooned now, arms bound to the elbows, torso constrained to a strict upright position, legs left with just enough slack for torturous, mincing steps.

He stood and took a step back, admiring his work.

“Not bad. You've done very nicely.” There was tenderness in his touch as he tucked an errant strand of hair behind her ear, and she leaned her cheek slightly into his palm. “Now,” he whispered, loud enough for me to hear, “let's give them something to really write home about.

“Bend over the end of the counter and show your ass to the neighbors.”

For the first time that evening she hesitated, taking a breath and squaring her shoulders rather than moving to comply. I found my own breath caught in my chest as I waited to see what would happen next.

“Really?” His tone remained level. “Things were going so well, and now you're going to throw it away over what some strangers might think. Assume the requested position, please, so that I may remind you whose opinion is of primary importance here.”

There was a subtle creak as the lines shifted with her movement.

“That's right. Spread your legs as much as you can and bend at the waist. You may rest your forearms on the counter.”

He had set the cane aside to concentrate on his ropework, but now he took it up again. He gazed at her ass like an artist considering his canvas.

“I'm afraid you'll have to explain these marks to Lenore. I'll gift wrap you after, so at least they'll have a pleasant presentation.” And with no further warning he cracked the cane across her upper thigh, raising a fresh welt directly parallel to the one from earlier, when she'd dared to look at me.

“One, sir,” she got out with only a hint of a gasp. He gave a small nod of satisfaction.

It was fascinating to watch. I knew from our correspondence how carefully Thomas thought these scenes through, the level of perfection he held himself to when entrusted with another body. He was thoughtful to the point of being slightly neurotic, keeping a constant mental tally of his own perceived errors and oversights. And yet, outwardly, he seemed supremely sure of himself. Not cocky, no need for swagger, he was simply a force. I was half inclined to submit to him myself, though bondage had never really been my area of interest.

I got lost in my own thoughts for a while, and when I returned my attention to the scene at hand six red lines crossed Marissa's buttocks and upper thighs, placed with admirable precision. She had counted off each blow, clearly trained in the procedure.

“I think that will be adequate.” Thomas propped the cane against the edge of the counter and exchanged it for a length of red satin ribbon he'd brought out with the rope. “Now we'll wrap you up and have you on your way.”

He held the ribbon in a bundle and grazed the soft folds over her wounds a few times, eliciting shivers.


With extreme care she pulled herself upright.

“Turn to face me.”

She did so, which also left her facing the window, still forbidden from looking to see if she had an audience of more than one.

Thomas looped the ribbon around her waist, keeping it flat and even as he knelt to focus on his work. He proceeded methodically, weaving between her legs and around her hips, applying tension that opened and exposed her. He was impassive, focused on the task, but Marissa, for all her discipline, was showing signs of arousal at such intimate touch. Her mouth sat slightly open, pupils dilated. Her nostrils flared and she took a sharp breath as he placed a length of ribbon just so, tracing a finger along the satin where it framed her labia to check for smoothness and proper tension. My hand strayed to my crotch again, stroking the soft bulge in my trousers as I imagined myself in a similar position.

He looped the ribbon back up to her waist and tied the ends in a festive bow over her navel. With a faint smile, he rummaged around in his pocket and came up with a bit of artificial mistletoe which he tucked in under the bow.

“There.” Thomas returned to his feet. “Hopefully Lenore will appreciate the extra effort. What do you think, Mr. M?”

The contrast between the satin and the hemp echoed the simultaneous elegance and brutality of her presentation. She was largely helpless, but carried herself with unimpeachable grace.

“Very nice,” I said with complete honesty.

Thomas pursed his lips and looked at his handiwork with a critical squint. “Good enough, anyway. We should be getting you home, Marissa. Go to the door, please.”

She did as instructed, proceeding delicately in her hobbles and impossible shoes.

He draped her coat over her bound arms like a cape and replaced her scarf before doing up the buttons. “Wait there,” he instructed her, as he crossed the room back to where I sat.

“I shouldn't be gone too long. Half an hour at the most.” He bent to give me a quick parting kiss, and I couldn't help but feel pleased, though it seemed Marissa had done far more to deserve his affection than I had.

As he headed out, Thomas grabbed the loose sleeves of the coat and used them as an impromptu lead to guide Marissa along behind him. The door clicked shut.


That had gone completely according to plan, and yet been entirely different than I had expected. I had thought I would be more detached, simply a pair of eyes, but instead I had ridden high on the energy in the room, identifying intimately with both players at once. Now, alone in the place, there was a vacuum.

I went to switch off the music. It felt like part of the earlier scene, and I was ready for quiet. I drew the blinds to block out any of the prying eyes Thomas had brought to our attention. And then... what?

There was a kettle on the stove. If he was walking Marissa anywhere he'd come back cold, so I put some water on to boil and went rifling through the cupboards for tea. He had the good kind, loose leaf in shiny foil packages, and a proper teapot with a cozy worthy of any grandmother's kitchen.

I smiled to myself as I warmed the pot and measured out the leaves. I hoped Thomas would notice that I'd taken the time to do things right.

While the tea steeped, I wandered over to the bookshelves. There was a lot of history, also a lot of erotica. I recognized a smattering of titles from my own shelves, but there were more than enough unfamiliar options to keep things interesting. I took down a book on historical naval uniforms, a slim volume on traditional American scrimshaw, and finally a collection of BDSM short stories and went back to the kitchen for my beverage.

The apartment was small, and offered only the chair I'd been in before and a couple of stools by the kitchen counter for seating. I felt like putting my feet up, so I moved my bag from where Thomas had left it on the bed, slipped off my shoes, and made myself comfortable on the mattress with my books and tea.

Not long after, while I was studying an illustration of an intricately carved pie crimper in the scrimshaw book, there was the sound of a key in the lock announcing Thomas's return. I could feel his eyes on me when he entered the room, but I decided not to look up, packing my barely contained excitement into a little knot in my chest.

“I made tea,” I offered, turning a page.

“You lifesaver. It's frigid out there.” I heard him pour a cup, then the soft pad of footsteps as he approached the bed. I relented and made eye contact when he hovered on the edge of my peripheral vision. He was looking down at me warmly. “You've got some of my best porn there, and you're choosing to read about pie crimpers?”

“What can I say? I like pie. But I was getting around to the other ones.” I closed the book and set it aside. Thomas sat and stretched out on the bed next to me, just close enough for our arms and thighs to rest comfortably together. “Maybe I can read some of my favorites to you later,” he suggested, as he took a sip of his tea.

He gave the cup an evaluating glance. “This is pretty good.”

“It should be, you bought it.”

He cocked his head in acknowledgment, but threw me a playful nudge anyway.

There was a stretch of comfortable silence before I asked, “Should I... feel bad about Marissa being sent on her way like that? I mean, I'm glad to have you to myself, but wouldn't she like to be here basking in some afterglow with you?”

“Not at all. Even if you weren't here, this is our arrangement. She and I have our fun, then I return her to her wife--”


“Right, I bring her back to Lenore to finish out the evening. Marissa and I hardly ever have sex.”

I hadn't said anything about sex, but it was gratifying to know that it was on his mind. I placed a tentative hand on his thigh and he leaned into me, almost imperceptibly, so I ventured a stroke of my thumb.

“I really enjoyed watching you.”

“I'm glad. I wasn't sure. You didn't really get involved, even though I'd given you permission. I was worried you might be bored.”

“No. I was riveted. You two seemed so perfect together, I didn't want to get in the way. It was a pleasure to just absorb it all. And...” I knew what I felt, but wasn't quite sure what to say.

“And?” he prompted.

“And it was really... arousing, to see you so in command and authoritative and to know that you'd be mine later. That I had a, sort of a backstage pass.” I slid my hand further up his thigh.

“You're with the band.” He joked, but his voice was a little husky.

“Yeah. Like that.” I moved to face him, a knee on either side of his thigh, and ran a hand down his chest. “You worked hard while all I had to do was sit there. Why don't you let me take over for a while?” He smiled and dropped his head back against the wall as I unbuttoned his shirt, trailing lazy kisses along the exposed skin.

“Do your worst,” he said with an indulgent sigh.

I wanted to take my time, get fully acquainted with this body that contained the mind I'd so enjoyed online. His torso was unremarkable, pale and lean with a smattering of dark hair, but when my fingertips brushed his nipples and he responded with an arch of his back and flash of tension across his face, it was the most beautiful thing I'd seen all day. I followed up with my mouth, nibbling with just enough force to result in a satisfying series of small gasps.

His erection was asserting itself against my belly, so I slid a hand down to caress and cradle it through the fabric of his pants. He sucked air through his teeth and arched harder at that touch, so I decided to relent and open his fly.

His cock sprang up as I grappled his waistband down over his hips. I threw the clothes on the floor and resumed my position straddling his leg so that I could grind out my own climax while I worked on his. I kissed at the tender crease of his groin and nuzzled my cheek against his inner thigh, resulting in more sounds of half-contained pleasure.

I took hold of his shaft and gave a few firm strokes before wrapping my lips around the head. He groaned and twined his fingers in my hair as I traced his coronal ridge with my tongue. Again, I was suspended between two poles: on top of him, driving the action, but serving him as well.

As I sucked his cock, I used my free hand to explore between his legs. I stroked his balls and trailed my fingers along toward his ass, which resulted in an enthusiastic buck of his hips. Change of plans then.

“Roll over.” I got off the bed and went to rummage through my bag while he did as I'd said. I'd packed lightly, so I was able to grab what I needed without too much trouble. My pants hit the floor and I shimmied into my harness, then popped my cock through the O-ring and arranged it just so. With lube in hand, I turned my attention back to Thomas's ass, which was now presented prettily on the bedspread. He'd even wedged a pillow under his hips in preparation.

I went back to work with my tongue, this time plunging right in to make up for lost time. He ground back against me making it clear that he was ready for as much as I could give him, but I licked and teased until he was keening for something more.

I stood up on my knees to open the bottle and fill my palm with lube, which I slicked generously over my cock. Thomas looked over his shoulder to see me looming over him, erect member ready for action, and gave me a smile that went straight to my crotch. A couple of fingers opened him up further, but he was still clearly hungry so I moved to give him something more satisfying. I tried to be gentle, to make my penetration suave and subtle, but he was having none of it and quickly drew me in to the hilt. That was fine with me, the impact of bottoming out providing the stimulation I'd been craving through the base of my cock.

I started to lose track of the chain of events then. There was thrusting, grinding, a lot of vulgar sounds, some his and some mine. I was an instrument of pure desire, providing us both with the payoff of an evening well spent. My climax was approaching, so I drove deep seeking the last bit of pressure I would need to get off while reaching around to stroke Thomas to his own finish.

He came, gasping, in a sticky flood over the back of my hand. I was only a moment behind, shouting through the intensity of the spasms that rocked me before I collapsed onto his back.

Once I regained my breath I rolled off to one side, which freed Thomas to chuck the pillow he'd been laying on and turn to look at me. His eyelids were at half mast and he had the dreamy look that follows a good orgasm. “Do you always wear a tie to commit acts of buggery?”

I looked down at myself, still half-dressed. “No, but it's a special occasion, so...” I raised a flirtatious eyebrow, then flopped back to stare at the ceiling.

He scooted over to rest his head on my shoulder and an arm across my chest. “That's right. Merry Christmas.”

I gave him a squeeze as I imagined myself at the family gathering, filled with holiday cheer that was the product of thorough and recent fucking. “Not for a few days yet, but it's hard to imagine things getting much merrier.”