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Guest Stories

Pimped Out

By Cattywumpuss

We were traveling and had found a gay club around the corner from our hotel. We spent the evening there, drinking and dancing and watching some of the more colorful characters gyrating around the dance floor in very little clothing. One of the guys who was dancing close to us kept smiling and winking at me. He was younger than me, with blond hair and piercing light blue eyes. I smiled back a few times, unsure of the attention. Shortly before we left the club for the evening, he approached our table again. You motioned for him to come over and he bent down as you whispered something in his ear. I couldn’t hear what you said due to the music thumping loudly in my ears. Whatever you said made him grin though.

We left and went back to our room. It had been a fun night but I was tired and was looking forward to some sleep. I didn’t realize then you had other plans for me.

After we got up to our room, we undressed for the evening. I slumped on the bed, tired. You were still full of energy though, buzzed from our time at the club and also because you were in a strange new place with me. You jumped up on the bed beside me and said we should have some fun, pawing at me to try and get me up and moving around again. I rebuffed you, tired and not wanting to do much. “Not now I said, I’m tired” as I tried to push you away slightly with my hands. “But I’m horny” you implored me . . . Lifting your top and flashing your breasts at me. “The girls need some attention.” I smiled back at you, but did not move. You whined and thumped me as you could tell I wasn’t going to move. You turned the TV on and I drifted off to sleep, with you sitting there beside me.

I woke up a while later. I had been dreaming and was in some kind of fight. I felt I was being pushed and pulled around, and slowly came to realize it wasn’t a dream and that I was being maneuvered around the bed. As I slowly woke up I felt a tug on my right wrist. You were turning me over on to my stomach. I realized there was rope around my wrist . . . and my other wrist too. I felt rope around my ankles too. Confused and not too sure what was going on I tried to get up. I made it to my knees and couldn’t move anymore. The ropes had tightened around my limbs and you had tied them off to the legs of the bed so I could only move so far. “What are you doing?” I said sleepily, still trying to figure out what was happening. “Just having some fun” I heard you giggle back at me as you flitted around the bed, double checking your knots.

“I was trying to sleep” I moaned at you. “Leave me alone.” I heard you sigh, and as you shoved a couple of pillows under my tummy you told me to quit whining and go back to sleep if I wanted. You sounded a bit angry and frustrated. I was still tired and kind of comfy with the pillows propping me up on all fours, so I kept my mouth closed and put my head down to sheepishly drift back off. I wasn’t asleep for long.

I didn’t hear the cane swish through the air, I was half asleep again. However, I felt it connect with my bottom. The searing pain shocked me awake and made me jump. I cried out as the burning sensation spread through my bottom. I heard you chuckling behind me. “Oh good, looks like you are awake now”, I heard you say.

I tugged on the ropes but you must have tied me down a bit better after I drifted off again, as I really couldn’t move from my prone position on my hands and knees. “Swish” I heard the cane come at me again . . . . I realized you must have pulled my boxers down too as there was nothing between the cane and my skin when it found it’s target the second time. I gritted my teeth and grunted as the pain flowed through my ass cheeks again.

“I wanted to have fun” you said to me, in an accusatory tone. “What the Hell” I said . . . still trying to get my head around my predicament. I heard the cane swish again and braced myself for the impact, grabbing at the bed sheets and ropes trying to pull myself away from you but getting nowhere. I cried out as the cane hit my ass again, hard.

“What are you doing?” I asked as you chuckled at me. “Teaching you a lesson” you said, as I caught you drawing you arm back again out of the corner of my eye. I closed my eyes and buried my head in to the mattress, taking a deep breath in anticipation of the impact again.

You continued to cane me. The pain built and I started to plead you to stop. As welts started to appear on my bright red bottom, I started to beg you, my eyes watering with the pain. “Please, I’m sorry I went to sleep . . . please stop, please” I managed to get out between the hits and my gasps.

My ass was a criss cross of cane marks, swollen and red, the skin barely holding together under some of your swings. My knees gave way and I slumped down a bit lower on to the bed, the pain spreading throughout my body. I heard you say something about not ignoring you again but didn’t clearly hear the rest as my head was swimming in sensations of arousal and pain. I started to sob quietly.

You hit me some more and then you suddenly stopped. I heard you gasp a little and then felt you tenderly poke at my ass cheeks with your finger. My bottom had gone partly numb with the pain a short while before, but I became faintly aware of something warm and wet trickling down the back of my thigh, I think. You disappeared in to the bathroom and came back out. I felt you place a cold, damp flannel on my ass. Dabbing at something. “I’m so sorry” I heard you whisper, dabbing at my ass cheek

All I could do was faintly moan, as I saw you go by headed back to the bathroom. I think I saw some blood on the flannel, but was not sure at that stage. You returned from the bathroom and started throwing some clothes on. You said something about going to see if the front desk had some first aid supplies, then there was a knock on the room door. I just lay there, not really caring what was going on at this stage. I was happy I wasn’t being caned anymore and was starting to relax.

I heard you say something about plans changing and that you were sorry but when you had invited him up earlier you thought I was going to be up for some fun or something. I moved my head slightly to look over towards the doorway and saw the blond-haired guy from the club that we had seen earlier. I started to laugh to myself, wondering what he was thinking with me lying in a heap on the bed, boxers around my knees, my ass cheeks a red, raw mess. I heard you say you would be back and then the sound of the door closing behind you.

I was lying there half awake, half asleep. I realized you hadn’t untied me, probably didn’t think of it after you got a bit panicky when you made me bleed. I had stopped struggling ages ago, and hadn’t thought about the ropes either. Suddenly I became aware of somebody standing at the bottom of the bed behind me. “Oh you are a mess, aren’t you?” I heard a strange voice say. It dawned on me that you had left the blond guy in the room while you had gone downstairs. “Hmmm” I agreed with him, as I lay there. Still too far gone to really care much.

Suddenly I felt something cold and wet fall down in between my ass cheeks. Then I felt fingers, spreading the cold wet substance around. After a few seconds I realized it was lube . . . . partly shocked, partly panicking, partly afraid . . . all I could do was let out a soft moan as the blond guy slid his lines up finger in to my asshole. Instantly I tensed up, but as he started working his finger around inside me I started to relax again. Besides, I didn’t have the strength or energy to fight back, and I was still tied to the bed. I groaned softly again, as he started rubbing inside me near my prostrate. It felt good, and pleasant sensations washed over me. I felt my cock getting wet again, down between my legs.

After a few minutes he stopped, and withdrew his finger. I let out a sigh, that may have sounded more like a moan. After the evening I had been having it was hard to tell. Next I felt the mattress move, as the blond guy climbed up beside me and I felt his knees down beside my thighs as he climbed on top of me. “What are you doing? I asked, weakly, too quiet perhaps for him to hear me. I asked him where you were and then asked him to untie me and leave me alone. I don’t know if he didn’t hear me, or just ignored me.

I felt his hand in the small of my back, pushing me down in to the mattress holding me still. His other hand brushed up against my ass cheeks as he spread them a little and pushed his cock towards my now lubed up hole. I couldn’t do anything and felt him slide in to me, I let out a soft moan as I felt his member fill me up. My skin still raw and tender on my ass cheeks, hurting and stinging every time he brushed against them. He moved his hands to my hips, and pulled me towards him as he thrust deep in to me.

My ass felt like it was splitting, but then the intermittent stinging and throbbing from the fresh cane marks on my cheeks kept filtering in and was overloading my senses. I surrendered again, for the second time that night as the blond-haired guy started grunting and moaning as he thrust in and out of me. The sensations started becoming pleasurable again as I relaxed and submitted. I started to groan softly as I felt my breathing heat heavier and more rapid. My own cock was semi hard and really wet . . . .

He started to get louder as his thrusting suddenly slowed, I felt his grip on my hips tighten . . . “Oh fuck!” I heard him shout as I started to feel his cock pulse inside my asshole. Feeling him throb inside me like that made me climax a little as well. I felt my cock twitch and pulse a bit in response to his, and I think I felt more wetness between my legs. It was hard to tell though, as I was already such a mess.

I felt him withdraw from me, as I exhaled and felt my asshole shrink back to somewhat normal. I just lay there, sore and hurting, somewhat aroused, really tired and spent, so many feelings and emotions flowing through me all at the same time. I have no idea what the blond guy did afterwards, but shortly after he had shot his load in to me I heard the room door close and assumed he had left. Shortly after that I heard the door open again and you called out to me, apologizing for being so long. I heard you say something about the front desk not having first aid supplies and then you started to untie me.

I didn’t have the strength or energy to move as you lifted my limbs up one by one and removed the ropes from them. The red marks deeply ingrained in my skin. You asked where the blond guy was, I faintly motioned at the door. You started dabbing something on my ass cheeks, I guessed it was some kind of anti-septic given how much it stung again. I gasped with each dab. You continued cleaning me up until you you got further down towards my crotch.

You suddenly stopped as you realized something was up . . . as you tenderly parted my ass cheeks the blond guy’s load of wet sticky cum started to ooze out of my hole. “Oh my God” I heard you cry out, as you let go of my cheeks and started to cry . . . . “What did he do to you?” I felt you fall on the bed beside me, cuddling me and sobbing as you rested your head on my back. I was drifting off, too worn out and tired to move from where I was, despite the now damp messed-up mattress I was lying on. My eyes grew heavy as my breathing slowed and I fell back asleep.