A Very Unexpected Encounter

I've posted stories based on my life in a few places and gotten requests to write more. The events have had profound effect on my life which led me to go into more and more detail. Next thing I know, it became a small novel. A few details have been changed to protect people's identities and prevent an "I know him/her" moment. What is written is about 95% - 99% as they occurred. The back and forth conversations between me and one of the persons did not always happen as written. Some details have been lost over the years but what is included are things we have said to each other and mirrors how we interact even to this day. The person I had the encounter with helped me write the post and recall the little details.

Part 1 - Background

I stood on the street corner staring into my phone on a nice spring evening. Through the usual street noises, I hear someone call my name. Turning around, I slowly scanned through the crowd of people and saw a familiar face.

"Zoe!"

"That took forever and a day. Not only does your hearing suck but you need to get you shitty eyes checked too."

"Zoe, I'll never know why we didn't work out and how a great catch like you is perpetually single."

"Go fuck yourself with a sandpaper dildo!"

Back in college, "Zoe" and I dated for about 3 years. The student body was 85% male and finding a mate was challenging. Zoe was one of the single hot chicks up for grabs. She knew she was beautiful, knew it and flaunted it. Those confident enough to approach her usually got scared off by her very assertive personality. To me, it was all part of the fun. The best way to describe our relationship is best captured in the music video for the song "Try" by pop artist P!nk. It was a strange love where we seemed totally into each other yet always at each other's throat. She had a razor sharp mind attached to an equally sharp tongue which she wielded like a Scottish claymore. I usually gave as good as I got and fired off many preemptive shots to keep Zoe on her toes. One friend seemed to think we intentionally provoked the other in some kind of perverse game of mental chess. Deep down, I think there is quite a bit of truth in that hypothesis. Each loud argument seemed to end in a long "angry fuck" session. The mental sparring turned in physical sparring. The rough sex often left us bruised and battered but that's another story.

I noticed that she was with "Claire" who recently joined our social circle. She and Zoe worked together and somehow became fast friends. Claire was a hottie herself but seemingly the polar opposite of Zoe. She was polite, upbeat, geeky and bubbly. "Adorkable" was the description that came to mind. Her hanging out with Zoe was like a naive baby lamb being led through life by an aggressive honey badger.

"Hey asshole! You listening?" Zoe shouted and she snapped her finger in my face, "I'm not speaking ancient Greek here! Let me ask you again very slooooowly. What... are... you... doing... here...???"

My mind shifted off Claire and back to Zoe. Yep, she hasn't changed one bit all these years.

"Well, I figured I'd first ruin your night by stalking and cockblocking you every chance I get. You'll then end the night playing finger puppets on your worn out, hot dog down a hallway cunt."

Before she could get her usual last word in, I cut her off.

"I'm supposed to meet my brother for dinner but his car has a dead battery. Road service said it will be at least an hour. Guess I'm on my own for food. You?"

"Claire and I had a shitty week and need to get our drink on. You might as well join so I can hear your story tomorrow about how you fell asleep on the toilet trying to jack off your limp whiskey dick."

"Zoe, if I can't get it up, it's because I had a bad flashback of those awful, toothy blowjobs you give."

The back and forth exchange continued until we sat down at the bar. We ordered and downed the first of many rounds of drinks. The conversation started with the usual topics. Work, gossip, summer plans, etc. As rounds of booze were consumed, the alcohol began to set in. Everyone got a bit looser, discretion began to melt away and the talk became less PG13. Still, I avoided topics I thought would scare Claire away. As usual, Zoe did her best to egg me on.

"Hey remember the time we all went down to Miami and Raphael picked up that really hot Brazilian girl only to find out it was a man with a 9 inch dick? Nearly broke his fucking leg jumping off the balcony to get away. Bet you would've let him stick it up your ass and tickle your tonsils from down below."

"Then there was the time dumbass here hid in the bushes with a queasy drunk girl as the cops busted the party we were at. She was laying on top of him and blew chunks. He took a facial of half digested burrito and about 10 shots of tequila. Not the blowjob you were expecting huh?"

Much to Zoe's chagrin, I managed to bite my tongue and dodge her provocations regarding past misadventures. Overall Claire and I got along quite well. We laughed at each other's cheesy jokes as well as get in a bit of poking and tickling. While fun, it didn't feel like there was any sexual connection. Guess Claire just wanted a night of drinks and getting in her panties would have to wait for another night. I got a twinge of guilt going after such an innocent gal anyway. In the meantime, Zoe was the third wheel and not being the center of attention always irked her. Eventually she got bored and made the executive decision to call it a night.

"Hey! gimme some money so I can pay and get to more important things like picking sand out of my vagina."

"Sand? Small boulders and Japanese subcompact cars can get lost in that cavern you call a pussy."

"Better than your mom's asshole that she used to shit you into his world."

Wanting to continue chatting with Claire, I tossed Zoe my wallet and told her to pay whatever share was mine and Claire's.

Part 2 -- The Encounter

To save on cab fare, Claire and I agreed to share a ride. Her place was closer to mine and she would be the first stop. She only had just enough cash to cover her leg of the ride. I reached down and suddenly realized my wallet was with Zoe.

Our plans changed, it was decided that Claire would pay for the ride to her apartment. I would get in contact with Zoe to drop off my wallet. Once at her place, she invited me inside and I sat down in the living room trying to get in touch with Zoe. Unsurprisingly, she didn't answer her phone or reply to my text messages. Life with Zoe was scheduled around her convenience. Didn't matter if it was an emergency. You could be bleeding out from a severed leg and she would insist on swinging by a coffee shop on the way to the ER.

Claire reappeared and asked if I minded that she took a shower to freshen up, I told her to go ahead. By then I had given up on Zoe and was thinking up a new plan to get home.

"I'm coming out, can you please turn around?"

Being a gentleman, I turned my head but I did try to sneak a peek out of the corner of my eye. All I saw what a blur of Claire with towels wrapped around her body and hair zip by. After hearing the bedroom door close, I let her know that Zoe was not answering and I would likely have to walk home. Being it was past midnight, she thought it wouldn't be safe to walk home buzzed. Claire suggested I take a shower to clear my head a bit and I accepted the offer.

The warm water felt good and I savored the nice steamy shower. Feeling refreshed, I hopped out and reached for a towel to dry off. All I could find was a hand towel. Took a while but the little 2' x 2' cloth did the job. Then I realized my clothes were gone. Very strange. I cracked open the door and called out to Claire but got no response. I waited a minute and called again. Still no response. At that point I decided to walk out to find her. With one hand holding the little towel over my crotch I slowly stepped into the hallway. As I turned the corner into the living room, there she stood.

It was not the Claire I was expecting. For a second, I questioned whether I was drunker than expected and hallucinating. There stood a woman in a leather and latex bustier, leather corset, leather thong panties, long latex gloves, knee high boots, thigh high stockings, and garters. Her hair was pulled back in a tight ponytail. In her hand was a menacing riding crop. The dark makeup along with the expression on her face was all business. Her excellent figure was further accentuated by the tightly cinched corset. Tall platform heels on her boots almost closed our height difference. Standing practically naked in front of and fixated on bizarro world Claire combined with a booze addled mind prevented me from coming up with a sound action plan.

At this point, I have a confession to make. I was not at the restaurant to meet my brother and the meeting with Zoe was not by chance. Zoe had told me that Claire recently broke up with her loser boyfriend. The guy had a dead end job, only interested in playing video games all day, got shitfaced or high most nights, and never paid his share of expenses. He once cheated on her and passed on a bout of chlamydia. Another time he got sloppy at a company event at Claire's workplace and started a fight with a senior exec. When he was really drunk, he would push her around and blame her for his failures. She finally gave him the boot a month back. Before jumping back into the dating pool she first wanted to have some fun to get her confidence as well as mojo back. She put up with years of shitty, unfulfilling sex and craved more excitement. Zoe got in contact with me and asked me to help guarantee Claire a great night out. The bonus being that I may have a chance to hook up with her. I may have ended up with more than I bargained for.

"Drop the fucking towel!"

"Huh?"

She walked up and slapped me across the face. Holy shit, I saw stars and my face burned.

"Don't make me say it again or your ass is out the door just the way you are."

The prospect of getting home wearing just a face towel with no money or ID sunk in, I reluctantly dropped what little protection that shielded my dignity. There I was standing butt ass naked in front of what was the sweetest girl just 30 minutes ago. She walked around me like a cheetah stalking her prey. Claire looked hot and my dick was beginning to respond.

"Stand up straight, eyes forward, spread your legs, and hands behind you back."

"Okay"

The riding crop slammed into my ass cheek with a loud crack. The sharp pain radiated from where leather met flesh. Dammit!

"Every answer ends with, 'Yes Mistress Claire' That was your one warning. The next one will really hurt."

"Yes Mistress Claire."

I felt leather cuffs being cinched tight against my wrists and snapped together. My ass got another whack of the crop. Circling back in front, she took one of my nipples in her hand and pinched hard. I winced in pain. Seeing the expression on my face, she squeezed even harder. I gritted my teeth. Walking behind, she gave my ass another smack with the crop. Walking back in front, she grabbed my hardening cock and gave it a painful clench.

"I see you are beginning to enjoy this. Hope it's up to the task. You don't want to know the consequences of failure."

With that she gave my penis a quick swat of the crop. Dammit.

Walking behind, a finger went between my ass cheeks and pushed against my asshole.

"This hole will be penetrated. The more you satisfy me, the more lube for what I feel like shoving in you will get. Disappoint me and you get a dryfucking you'll never forget."

Another swat of the crop hit home. Dammit. A feeling of dread came over me. Why do I let myself get into these situations?

Claire walked over to the coffee table, picked up a collar, leash, and some clothespins on a string. She walked back and snapped about a dozen clothespins all over parts of my body. The initial sting as they clamped on soon became a manageable, dull pain. The collar was tightened around my neck and the leash given a quick tug. This was followed by a forceful pull to bring my head down below her level. She buried her lips into mine and we kissed deeply. Our lips and tongues locked and danced in a sensuous oral ballet. I savored her soft lips. It felt tender. A hard bite on my lower lip before she pulled me away brought me back to reality. Dammit! An instant later, she tugged the string attached to the clothes pins and each one snapped off my body in the blink of an eye. Fuck! It felt like my body was on fire. I cried out in pain and fell to my knees. This led another slap to the face. Her hands then grabbed and pinched the sensitive flesh once gripped by the clothes pins to force me back on my feet. I groaned in pain. Fuck that hurt!

"Shut the fuck up! Shut up!"

Five rapid fire swats with the crop on my ass reinforced the order. I gritted my teeth as the pain very slowly subsided. She was slowly breaking me down.

"If you make me unhappy, that will be the least painful punishment you see all night."

With a tug of the leash, she led me into her bedroom. Less than an hour ago, it was a cute bedroom with all the accessories expected of a trendy girly girl living in the big city. The plush, seafoam colored comforter was pulled back to reveal a hidden darker side. Various pieces of bondage gear such as cuffs, clamps, gags, blindfolds, and harnesses were laid out alongside dildos, plugs, and vibrators of various sizes. The smallest dong looked like a modest 6 incher but there was also a 12 inch phallus as thick as my wrist. She pointed behind me at the closet.

"Look"

Among the fun fashions expected of someone like her, I saw my clothes and phone sitting inside a small safe. She reached over, closed the door, and pulled the handle up locking the safe tight.

"It has a six digit combination. Put in the wrong code five times and the keypad locks out for ten minutes before you can try again. My phone is hidden somewhere in the apartment. You will never find it. You decide whether you want to try something stupid. Fuck me over and your ass is out the door just the way you are."

I knew I was out of options and completely at her mercy.

I was walked across the room, cuffs separated and pushed face forward onto the bed. She then climbed onto the bed and laid back against the headboard. Snapping off the buttons on her bustier, her perfect breasts spilled out in front of me. She grabbed a handful of my hair and pulled up my head.

"Massage them, lick them, make my nipples hurt."

Lust came over me and I complied. Both my hands started kneading those wonderful mounds of flesh. I scooted up and took a nipple in my mouth. My tongue swirled around as they got harder and harder. I lapped up and down and gave them an occasional nip. After a few rounds, I switch over to the other breast all while continuing to massage the other. Following orders, I would take my mouth off and give each nipple a hard pinch. She yelped in pain but seemed to enjoy it. If I lingered too long, the leash got a yank reminding me to pleasure the other breast.

"Keep going slave. I don't feel satisfied yet. Want your ass ripped apart with a dry dildo?"

I felt a finger uncomfortably pressed against my asshole along with a swat of the crop. Dammit. That was all the motivation needed to redouble my efforts. Not sure how long I was at it but my jaw was hurting and tongue getting tired. Any time I slowed, I got a nice crack of the riding crop on my ass. After a while, a tug of my hair signaled that task was done.

"Take my panties off and get to work. You earned some lube but it will not be much."

I scooted down and pulled down her panties. A huge gush of juices and completely soaked pussy met my eyes. I immediately smelled her. Whereas Zoe was strong and musky, Claire was lighter but still a nice womanly scent. The smell was heavenly. I fought every urge to stick my dick into her and pound away at that pussy. Instead, I inserted a finger and began to massage the inside. She threw her head back and moaned. It only took me a few strokes to try a second finger. Her soaking wetness and arousal opened her up and a second digit went in effortlessly. With some probing, I found her g-spot. Messaging the gear elicited more yelps of pleasure. At the same time, my thumb found her clit. By now she was making guttural animal sounds as I stroked away at her love buttons. Her hips lifted as she pushed into my hand.

I licked a finger on my other hand and smeared some of her juices on it. Massaging her asshole and adding some of her juices that had dripped down, I push it right in. She arched her back and moaned. Hmm... that finger met no resistance and she enjoyed being penetrated anally. I repeated again with a second finger and it too slipped in quite easily. It was not the first time someone has penetrated her there. Claire also did not protest the penetration or show any signs of discomfort. The good girl façade further crumbles. This fingering until I felt a tug on the leash and then a hand roughly shove my face into her pussy.

"Work my holes and lick me hard"

I did as ordered and moved right into the wetness. The position was very uncomfortable with both her vagina and asshole filled with my fingers and me hunched over licking her pussy was causing all sorts of muscles to ache, spasm, and cramp. Still, the thought of a more painful alternative drove me to continue. My tongue traced her her outer labia causing her to make soft sighs of approval. The teasing continued as I moved out to her legs licking and nibbling on her soft inner thighs. Slowly I moved back in and focused in on her engorged clitoris. My mouth took her in and tongue swirled around the hood. Her breathing quickened and she let out a deep moan. I picked up the pace of licking and fingers worked her g-spot.

"Two fucking wasted years. You are going to make up for all that lost time. I will so kick your ass if you slow down."

What!?! She dates some useless dickhead and now I have to pay the price. Down below it was like a dam burst. The flood of her juices from the arousal flooded my mouth. So much was dripping down her ass crack that I didn't even have to add lube to the fingers in her asshole. Her climax was building and I sense that she was getting close.

"Oh my god, Don't stop, Harder, pump and lick me harder. More... more... deeper.... more... go.... faster... ahhhhhhh......"

Claire's orgasm suddenly hit. Her pussy and ass muscles were spasming so hard it felt like they could snap my fingers in half. Using all the focus I could muster, my tongue found what got the best response and steadily worked her clit. A gush of wetness added to the already gooey mess. Her hands shoving my face deep into her and strong thighs squeezing my heads like a vice threatened to cut off my air supply. I could barely breathe and my nose was clogged with her sticky juices. After what seemed like forever, her orgasm subsided and I was able to get air again. A tug of the leash got my attention. It took a few minutes for both of us to catch our breaths.

"Clean up every drop"

With much of her crotch a wet mess, it took me a while lick everything up. It felt like I drank a liter of her juices. She scooted off the bed and pushed me onto my stomach. She pulled out two ropes that had been hidden behind the headboard. With the precision of a Boy Scout, she deftly tied a few knots through the D-rings on the wrist cuffs and I was secured to the bed. A ballgag was shoved into my mouth and the harness tightened around and above my head. A cold drizzle of liquid between my ass sent a chill up my spine. A finger pushed into my asshole. There was a pause and a few quick pumps. A second finger was then inserted and quickly followed by a third. A hand came down hard on my ass. Dammit. Claire leaned over and whispered in my ear.

 

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