A Fun Surprise

Sam

I woke up alone in the hotel bed and checked the clock on the bedside table. 9:43 AM. Mark must've let me sleep in after another late night of orgasms, rather than waking me as he was leaving for work.

I moaned contentedly and luxuriated in the cozy bed, stretching my limbs and enjoying the soft, cool sheets on my bare skin.

As I reached onto Mark's side of the bed, my hand brushed over something. I found a postcard sized piece of hotel stationary near Mark's pillow. On it, he'd written an address (1550 Center Avenue), a time (12pm) and nothing else.

I smiled to myself, lots of questions running through my mind and tingles between my legs as I imagined what kind of fun adventure Mark might have planned for me.

I texted him to let him know I'd received his directions.

Sam: I got your note lol

He responded a couple of minutes later.

Mark: ;)

Mark: Your Uber will be there 20 minutes before the time

My smile grew as I saw Mark was apparently going to keep things vague. Although I had no idea what I was in for, I felt excited that he had put some thought into whatever it was with me in mind.

Sam: Do I get any hints?

Mark: What kind of hint do you want?

I thought about it, not wanting to pressure him to spoil anything. But there was a more practical question I had.

Sam: What should I wear?

Mark: Other than the thong, it's up to you ;)

Mark: But I want to know what you choose

Sam: Okay :)

Sam: Should I be nervous?

I realized I was biting my lip as I waited for Mark's response. The three dots bounced over and over as he seemed to decide how to respond.

Mark: Do you trust me?

I smiled to myself.

Sam: I do

Mark: Then no ;-*

Sam: Okay <3

And with that, I tried my best to focus on the excitement rather than my nerves as I got ready to go.

Since the mysterious appointment was at noon, I hoped there might be time for Mark to meet me there over his lunch break. It didn't seem advisable to meet a stranger alone in an unfamiliar city. But even as I thought about that possibility, the line between excitement and apprehension was blurred.

I wore a t-shirt dress over a lace cami bralette and the thong Mark had already picked out. The t-shirt hung off my shoulder a bit, hinting at the lace underneath.

Then I looked at the clock again and realized I was ready early, which left me some time to scroll on social media as I sat with my anticipation.

Mark texted again at 11:30. Maybe he'd meant it as a reminder alarm for me, as if I wasn't checking the time every two minutes.

Mark: ;)

Mark: Ready to go?

Sam: I am :)

Mark: What are you wearing?

Sam: A t-shirt dress, the thong, and a lacy bra top

Mark: Mmm

Mark: Feeling tingly? Wet spot on that thong?

I reached under my dress and rubbed two fingers over my pussy to feel the dampness there.

Sam: Yes, it's growing

Mark: Good

Mark: Better head out soon ;)

Sam: I will :)

With the reminder from Mark, I went down to the hotel lobby a few minutes early to wait for my ride.

The driver was right on time.

"Sam?" he asked as he got out of the car and came around to my side. He was a little taller than me with dark hair that was buzzed short, and nice eyes.

"Yeah, that's me," I replied with a smile.

"Nice to meet you. I'm Ryan," he said, smiling as he opened the back passenger side door for me.

Something about the smirk on his face as I got in the car and he shut the door behind me made me wonder just how much he knew about where he was taking me and why.

"How are you liking Boston so far?" Ryan asked once we were on our way to wherever he was taking me.

"To be honest, I haven't seen a ton of the sights so far," I answered, blushing. "But what I have seen has been pretty great."

"Cool," he said, agreeably.

And there was that smirk again. I couldn't resist asking, "So, do you know where we're going?"

"I do," Ryan answered, looking up at the rearview mirror to meet my eyes. "I take it you don't?"

"No," I admitted.

"Well, you'll find out soon enough. We're about there."

Looking out the window, I saw we were pulling up to an industrial office park. I frowned slightly in confusion. I don't know what I was expecting, but it wasn't that.

Then I had a momentary panic that Ryan had intentionally brought me to the wrong place. But when I looked at the address on the building, I saw it matched what was on the card Mark had left for me.

Even through the uncertainty, knowing that I'd arrived wherever Mark intended me to go kept me excited.

"Here we are," Ryan said, putting the car into park. "And this is for you."

He handed a small gift bag back to me, and I peeked inside. There were four pairs of fuzzy handcuffs, a matching blindfold, and another note on the hotel stationary.

I blushed, noticing that there was no tissue paper or anything else to keep Ryan from seeing what was in the bag that Mark had apparently given him at some point. That must've been what his smirk was about.

I took out the note first.

"Go into the first room on the left, inside the main door. Sit in the chair and wait," the note said.

I felt more tingles and bit my lip, getting a clearer image of what Mark might have planned.

I got out of the car and thanked Ryan for the ride.

"My pleasure. Have fun," he answered with a wink.

"Thanks," I said, smiling and laughing a little in response, feeling awkward.

The building's main entrance was unlocked, and there wasn't anyone around as I stepped into the lobby. I spotted the door to the left that Mark's note had indicated. It had a room number, but no other label or sign telling what type of office this was.

I opened the door slowly and peered inside to find a bigger space than I'd expected. The chair Mark had referenced was in the middle of the room. There was another door on the opposite wall, some other stacks of chairs, and a few tables pushed out of the way. The room was dark, other than some indirect sunlight seeping in through a window on the front-facing wall.

And there was another note waiting for me on the chair.

"Get naked except for the thong. Then put on the cuffs and blindfold," it read.

I smiled and followed Mark's directions, stripping my clothes off with little self consciousness. I set all of my things aside and sat down before connecting the restraints to my wrists and ankles. Then I put on the blindfold and sat back to wait.

As I settled in, I realized I could hear and feel my heart pounding hard and fast in my chest in the otherwise silent space. The building seemed to be deserted, but Mark had been very specific about my arrival time. I wondered how long he intended to leave me waiting here alone, mostly naked.

I didn't have to wait long for my answer.

After just a couple of minutes, I heard the door behind me open and close. Then footsteps padded on the carpet, coming closer.

Two hands ran over my shoulders, my neck and cheek, and then down my chest. They cupped and squeezed my breasts, thumbs rubbing over my nipples, making them hard.

I moaned softly, squirming in the chair and arching into the touch.

Light fingertips brushed down my arms, warm breath on my neck. Then he pulled my wrists behind my back, and I felt and heard the cuffs clicking together.

His hands covered my breasts again, cupping and feeling their weight, caressing them, then pinching and tugging on my nipples gently. Then he moved along, down over my stomach, thighs, and calves, stopping occasionally to squeeze and massage my tense muscles.

I smiled and bit my lip, already struggling with being unable to see anything. Every time I almost convinced myself that it was Mark touching me, I would feel or hear something that left me wondering.

Then he repositioned my legs and clicked the ankle cuffs around the legs of the chair so that I was fully restrained.

Moments later, I heard the door behind me open and close again, and someone else came into the room, pushing what sounded like some kind of cart. They rolled and positioned in front of me, and then another set of hands pushed my knees further apart. They slid up my inner thighs and pressed into the fabric of my thong, rubbing around between my lips.

The unexpected touch caused me to gasp and moan louder. I wondered if the second guy was actually Mark. He had a more confident touch than the first guy. The uncertainty was making me wet, much more of a turn-on than I'd expected.

Breathing harder and moaning steadily, I pressed into the fingers, grinding as they rubbed up and down along my slit, between my lips.

Then there were more hands pulling my legs apart from each side, running up my inner thighs.

The guy in front of me reached up to grab my hips and dragged my ass closer to the edge of the chair. He slid a finger under my thong, pulling it aside and exposing my wet lips. Then he explored my wetness, rubbing around and pushing inside of my slick opening.

I moaned and squeezed around his finger, back arching as I writhed and tugged at the restraints. Mark likely would've used more than one finger right away, knowing I could take it. The thought that it was likely a stranger's finger in my pussy had me close already.

"Please..." I begged. It came out as a soft whimper.

"Please what, slut?" asked a voice that definitely didn't belong to Mark.

"Oh god!" I moaned. "I need to cum!"

His finger moved around inside me, alternating in and out, deep and shallow. His thumb rubbed circles around my clit, occasionally flicking or pressing over it.

More hands grabbed my tits, squeezing and cupping them from behind. Still more touched me all over: cupping my cheek, rubbing my face, and all over my chest and stomach, squeezing my hip and ass. I had no idea how many people were groping me and helping to make me cum.

That thought sent me over the edge. I moaned and yelled out loudly enough that the sound echoed and reverberated in the mostly empty room. My wrists and ankles tugged at the restraints as I writhed in the chair.

As I came down, hands continued to hold and squeeze my breasts, and the finger slipped out of my wet, throbbing pussy. More hands held my knees apart, pushing my legs open as wide as possible.

Then I felt a cold, hard, wet object pressing in between my lips. It felt much thicker than a finger, and harder than a cock as it moved up and down, under and around my clit. I guessed it might be a dildo. But as I felt it being pushed down towards my opening, I didn't really care what it was. I just knew that I wanted, no, needed, it inside me, whatever it was.

My lips spread around the hard object as it pushed in a little deeper, stretching my pussy open. Someone eased it in and out of me, going gradually deeper, causing me to groan with each thrust.

Then I heard a click, and the sound of a machine turning on. The phallic object continued thrusting into me at a growing pace, moving in and out, gradually deeper.

Meanwhile, hands continued to roam all over my tits, face, stomach, and legs.

I moaned louder as the machine increased its pace and depth until the dildo was fucking me mercilessly. Hands rubbed and squeezed my skin, pinching my nipples. I felt hot breath and lips on my neck and shoulders, kissing and biting.

Then one hand moved down over my clit, rubbing fast right away as the machine got louder and stronger, sending the dildo in and out faster. Hands pulled and twisted each of my nipples gently.

"Fuck!" I yelled out amidst a steady stream of moans as the toy pounded into me, in and out non stop.

Then I heard Mark's familiar voice from a few feet away, behind the machine. "Cum. Cum for them, my slut."

"Oh god!" I gasped, realizing that none of the hands were Mark's after all.

Someone else kissed my ear, biting down on the lobe. Two other mouths clamped down on each of my nipples.

I moaned and gasped, realizing that I was also smiling.

"Cum," Mark ordered once again. And I thought I could hear the warmth of a smile in his voice, too.

I came hard as the machine drove the dildo faster and deeper inside me and a stranger's fingers continued to rub over my clit fast. My whole body tensed up as much as the restraints allowed. My back arched, my thighs shook violently, my toes curled and pointed, and my feet went rigid as hands and mouths roamed everywhere. My pussy clenched and pulsed around the dildo as it continued thrusting away.

My clit was always sensitive after cumming, but as I was restrained in the chair, there was nothing I could do to stop the stranger from rubbing it, or the machine from continuing to pound my pussy. And they didn't seem to have any intention of stopping anytime soon.

"Mark!" I yelped, unable to form more words, hoping he'd know what I needed.

"Try to push past the feeling," he coaxed, and I could hear him moving closer.

"I can't, it's too much!" I yelped, trying to arch away from the overstimulation.

The guy who had been rubbing my clit pulled his hand away, to my instant relief. But then I heard a click, followed by a new buzzing sound. A moment later, I felt another toy vibrating on my inner thigh, moving up to my pussy right away.

"Fuck!" I yelped, bucking in the chair. My movement knocked the dildo machine out of line. I heard it continuing to thrust, but it was no longer fucking me.

Then hands cupped my cheeks.

"Focus on me for a minute," Mark said.

I forced myself to calm down, taking deeper breaths and turning towards him, focusing on the feeling of his hands cupping my face.

"Do you trust me?" he asked again.

"Yes," I answered, automatically. The reminder allowed me to breathe a little easier right away.

"I want you to push past that feeling of needing to pull away. Try to let it feel good."

"I don't know if I can," I said. I'd never tried pushing past that feeling before. Even when I was alone and masturbating, I'd always given myself a little rest between orgasms. "I might need a safe word."

Mark chuckled a little. "What word do you want?"

"I don't know," I smirked. "Maybe I can just say yellow if I need it to slow down, and red to stop."

"That works," he agreed, caressing my face affectionately.

I tilted my head into his touch, and his fingers brushed the side straps of the blindfold.

"Don't suppose you'll also agree to take this off and let me watch?" I tried.

"Not yet," he said.

Then I heard and felt the fucking machine being repositioned.

"Hold her legs open," Mark commanded.

And then I felt my legs being pulled apart from both sides. Someone else wheeled the machine closer.

I gasped as I felt sudden, cold drips on my pussy, followed by rough fingers, rubbing the lube around before inserting the toy once again. Then they flipped the machine back on, and the attached toy resumed thrusting in and out of my opening.

I moaned, my pussy clenching up right away, gripping the toy.

"Let me see that," Mark said to one of the other guys.

A couple of moments later, there was another click, and then the buzzing vibrations resumed.

Mark brought the toy to my arm first, so I could feel it on a neutral part of my skin. Then he slowly grazed it over my chest, circling each of my nipples. He traced it up to my neck, brushing it lightly over the skin above my shoulder, behind and under my ears.

I moaned and tilted my head, wanting to feel more.

He drew the toy over my cheek to my lips.

"Suck on it," he commanded.

I obeyed, opening my mouth for it and sucking the toy cock eagerly right away, thinking about how much I wanted to do the same with Mark's cock.

He allowed me to suck at my own pace for several moments before gripping a fistful of my hair to hold my head still. Then he pressed the toy further down my throat until I gagged on it, flinching and gasping in a breath as he pulled the toy back.

"Good slut."

I felt the wetness from my saliva as he brought the toy to my clit next.

"Oh, fuck!" I yelped, clenching up yet again.

He used his fingers to spread my folds, rubbing the toy in circles over and around my clit as the dildo attached to the machine continued fucking me.

"Still green?" Mark asked, checking in.

"Yes!" I yelled, feeling suddenly close again. "More!"

"Turn it up," Mark said to one of the others.

And then the noise from the machine whirred even louder, and I felt the dildo thrusting faster while Mark held the vibrating toy right on my clit, pressing in.

"Fuck!" I yelped, quivering.

"Cum again, Sam!" Mark commanded.

More hands were on me again, rubbing and groping everywhere.

"Pull her hair!" Mark told someone.

And then I felt a rough tug, and my head snapped back, causing me to yell out again.

"Cum again, and you can have a cock in your mouth," Mark said, knowing what those words would do to me.

And he was right. Moments later, I moaned and clenched around the toy, cumming hard.

"Good slut," Mark commended, more gruffly.

My ears were ringing as I struggled to come down. The machine did not let up its thrusting pace, and Mark continued rubbing the vibrating toy over and around my clit.

"Still green?" he asked, when I tried flinching away.

"I don't know," I gasped, trying to fight the urge to yell, "Red!"

I kept moaning and squirming, trying to squeeze my thighs together, but the hands holding them apart were too strong. A steady stream of curses flowed from my mouth. I felt close again already. Or maybe it was a lingering feeling from my last orgasm. It was difficult to tell. Either way, I pushed myself to lean into it.

Grinding my hips and pressing up into the vibrations, I tried to let myself go completely.

"Cum again," Mark commanded, pressing harder onto my clit with the toy and rubbing it around. "Right now. Fast."

The feeling was intense, and building. I wanted to cum again so much. I wanted to do it for Mark. And for myself, to feel more of the intense pleasure.

"Get ready to feed her your cock," he said to one of the other guys.

And then I heard a belt being unbuckled, and a zipper opening.

Fuck.

"Oh, my god!" I yelped, another orgasm overtaking me as I anticipated another stranger's cock in my mouth.

I came again, hard. My ears were ringing, so I wasn't sure just how loud my screams were as I was held in place and forced to endure more and more of the intense pleasure.

Then I felt hands on my head, turning me until someone could push his cock through my lips and down my throat. He held me down hard right away, gagging me on his thick length with a groan.

"That's it. Use that slutty mouth. There's nothing my slut loves more than gagging on a big cock," Mark said.

His words made my pussy clench on the dildo yet again.

As the stranger continued groaning and fucking my face, I realized two things. First, there was a flaw in our safe word plan, because even if I had been at red, there was no way for me to relay that to Mark while my mouth was full of cock. But second, I realized the distraction of having my mouth used made it easier for me to endure more pounding, and more stimulation to my clit. Either that or Mark was right, and I'd been able to take more than I thought all along.

From there, I got lost in a blur of orgasms. They turned up the speed on the machine a couple more times, as different guys took turns feeding me their cocks.

I didn't want it to stop. But at some point, I could feel the pain and numbness overtaking the pleasure. So, I finally spoke up when one guy pulled his hard cock from my lips.

"Yellow," I said, my voice groggy as I gasped for breath.

"What do you need?" Mark asked.

I tugged at the restraints and tried readjusting as much as I could while the machine continued thrusting.

"I think I need to change positions. I feel sore. And losing circulation."

"Okay," Mark agreed easily.