Her Dark Side

Her Dark Side

I had been dating Cindy for a little over 8 months. Her angelic Asian face was matched with a rail thin body. She was a touch over 5’ and weighed in at about 105 pounds. Her tiny breasts matched the rest of her physique. While she had a wonderful personality, I was disappointed to learn that she really wasn’t that sexual. I certainly got my fair share of hand jobs, but she rarely let me lick her beautiful pussy and she had only sucked me off one or two times (and they were lousy). We had a below average amount of sex for a new couple and I was constantly frustrated as she pranced around in tank tops and shorts when we headed to bed.

It was Thursday night and we headed out for dinner and a few drinks. As always, she was stunning, wearing a turquoise see through blouse with a white tank top underneath with her form fitting jeans. I couldn’t help thinking about her sexy body as we drank our wine and ate our food. As dinner wound down, we decided that we could spend the night at her place. As we walked into her apartment, she changed into her standard outfit of a tank top (black this time) and boxers. When she broke open another bottle of wine and told me to change for bed, I had a hunch I was going to be getting lucky. After a few glasses of wine, we started to make out a bit, with our tongues interlocking and my hands groping up and down her legs.

Being her usual self, Cindy kept her hands confined to my back and arms. She led me to the bedroom and turned off the light. We always did everything in complete darkness as you might expect with her. We headed to the bed wear we pulled off our shirts. Laying on top of her, I could feel her bare breasts against my chests. My dick started to grind against her pussy and she could feel me getting hard. With out tongues still going at it, she whispered: “I want you to fuck me, but first you have to get me really wet.” I assumed she meant that she wanted me to lick her pussy before fucking her. I couldn’t wait to flick my tongue all over that hairy pussy and lick that big clit of hers. I pulled off her boxers and her black panties and started to nibble on her neck, and then down to her tits. Licking those tiny nipples was so erotic, I was starting to dribble pre-cum thinking about licking her pussy. I started to head south kissing her ribs and then her tummy and belly button when she stopped me – “Just touch me to get me wet, it’s dirty down there.” I was so mad, but I sucked it up and said, “OK”. As I moved back up to kiss her lips, I reached my hand in her pussy and began what had become a regular routine. I rolled my eyes and unenthusiastically rubbed her clit.

A few minutes later, she arched her back and had her orgasm, telling me how good that felt. I was ready for the standard, “Let me rub your dick, Sam” when she surprised me and said, “I still want you to fuck me”. She pulled off my shorts and I started to get on top of her (her standard position), when she said, “Let’s do it doggie style”. I was shocked and delighted. She got up on her knees and waved her sweet ass in front of me. As I rubbed my dick to get myself hard, I couldn’t believe how deprived I had been. I had never seen her bare ass in 8 months because we had always done it in the missionary position. I entered her from behind and she moaned as my thick meat entered her. She didn’t really talk much during sex but she squealed a few times as I went deeper and deeper. That let me know that she was enjoying it. As I kept going, I placed my hands firmly on her ass cheeks and kept squeezing harder and harder, pulling her cheeks apart and widening her asshole. It was so tempting for me to stick my cock right up that hole and I thought that it might be my chance to break her out of her shell.

I licked my fingers and slowly rubbed the perimeter of her asshole as I kept thrusting in her pussy. She didn’t say anything so I assumed she was OK with it. In one swoop, I took my dick out of her pussy and jammed it in her ass. “Ah!” she yelped in a scream of pain. Nothing was going to stop me though, it was so tight and felt so good, I couldn’t wait to cum in her sweet ass. On every thrust, she shouted, “Oh God, please stop, no, it hurts, what are you doing, stop, shit, ow, fuck, stop, no” and then I came in her ass. What a sweet sensation as I spurted my gunk all over. As I pulled out, there was no noise coming from Cindy, I could only hear her sniffling. “That was great, baby. It felt so good.” I said as I lay down next to her. She was sniffling and maybe crying from the pain a bit, but I didn’t care at this point. I had a feeling deep inside she really liked it. She got up to go to the bathroom and I fell asleep right there, tired from the wine and sex.

I awoke the next morning and Cindy had left for work before I woke up as usual. There was a note on the kitchen counter as I was leaving; talk to you during the day, it said. Feeling refreshed and satisfied, I headed to work. After lunch, around 1:00 PM, I got an e-mail from Cindy.

Hey baby,

Meet me at the Claremont Inn tonight at 9:00, I got us a room for the evening — and I bought some things for you; can’t wait to see you.



Well, of course, the rest of the day went by so slowly that I almost left early. I actually went to the bathroom at about 4:00 and jerked myself off to relieve some of the tension. Had I released a sexual side of Cindy last night? Was she going to turn into a sexual animal?

At 5:00 I received another e-mail:

I’m already checked in and waiting for you – I have to run some errands before you come over tonight – see you at 9:00, come to room 519.


I went home and had a beer after work and then went home to change and shower. I arrived at the hotel at just about 9:00 and went to room 519. I knocked on the door and she answered dressed in an unbelievable outfit. A purple bra and panties with a long see through robe over it. I was floored and instantly my dick was hard. “Take down the bed, undress completely, and lie down, while I freshen up in the bathroom”, she said gently. I did as I was told and she came out a few minutes later with some handcuffs. I couldn’t believe how unbelievable this was. I had turned her from a conservative and boring lover into a kinky sex fiend in just one night. She grabbed my right arm first and handcuffed my wrist to one side of the headboard, and my left wrist to the other side with another. “I can see you are pretty hard” she mentioned. “That means you like it, huh, this is turning you on?” I nodded, as my dick was stiffer as it ever was. “Hang on a second, I’ll be right back”, she said as she headed back into the bathroom. I sat there wondering what she was going to do – I was so turned on and was a little frustrated that I was unable to stimulate my dick because I was tied up. Cindy came back out and walked over to me and slid her panties down her legs to expose her beautiful pussy. She got up on the bed and straddled over my face.

“You like my pussy?”
“I love it.”
“You want to taste my pussy juice, right?”
“I want to eat your pussy all the time.”
“Beg for it baby”
“Please let me lick your pussy. I love the taste and how your juice drips all over my chin when I eat you out”
“Are you sure you want my pussy juice?”
“Please, stop torturing me and let me have it”
“OK, open up your mouth and stick out your tongue.”

I stuck out my tongue as she dangled her cunt over my mouth. Seconds later, piss gushed into my mouth and all over my face as I gagged. The piss kept coming and I was trying to spit it out as fast as it came in. She finally stopped and I coughed and coughed trying to get the piss out of my throat. I was drenched in it and it smelled awful. “What the fuck?!?” I shouted. She had got off the bed and walked into the bathroom. “What the fuck was that?!?” I shouted again. There was no answer. I tried to free myself but the handcuffs and the bed frame were too strong. Cindy was still in the bathroom. “What the fuck was that?!? Get the fuck out here you fucking cunt!!!”

Cindy emerged from the bathroom dressed differently. She was now wearing jeans and a sweatshirt. “You didn’t like that?”, she smiled coyly.
“No, you bitch, why the hell did you do that, let me out of here.”
“Calm down, now, or you won’t be going anywhere.”
“What the fuck are you doing?!!!”
“That’s it, I’m going to shut you up.” Cindy went back to the bathroom and brought out some tape and stretched it right over my mouth. My muffled screams really didn’t make too much noise and Cindy sat down in the chair. She turned on the TV and sat for a few minutes without talking. I eventually stopped screaming and waited for her to start talking.
A few more minutes passed and there was a knock at the door. Cindy got up and looked at me with a smile as she opened the door and let in a 5’2”, 300 lb. black woman. She came in dressed normally in a black blouse and jeans and a suitcase.

“Hi”, the woman smiled at me. “My name is Monique and Cindy here tells me that you have been very mean to her…now I see she has tied you up and put some tape over your mouth as I’m sure you have been screaming.”

She reached back and opened her suitcase. I couldn’t see what she was doing but when she turned back around, I saw that she had some rope with her. “Sam, I am going to make sure that you can’t get out of here by tying up your legs.” Monique started to make a complicated knot around my ankles and roped these underneath the bed to make sure that I was firmly stuck. At this point, I really had no ability to move. She then reached back into her bag and pulled out a ball gag. I was really freaking out now.

“Now, Sam, I am going to take off the tape and put this ballgag in your mouth and secure it around your head. If I hear any screams coming from me, you are going to see some serious shit. There are a lot of things in my bag that I don’t want to use, but I bring them for my difficult clients. Do you understand?” I nodded cautiously. She pulled off the tape and stuck that gag right into my mouth and tied it around my head. I looked over at Cindy and she was hardly paying attention to what was going on.

Monique snapped, “I need you to keep your attention right here, OK?”
I nodded again. “Don’t you look at that gorgeous woman. You don’t deserve her. She told me that you raped her last night and I’m here to help rectify the situation. It’s going to be a long night for you.” I wondered what would be happening next when Monique stood up and took off her blouse and jeans. She stood in a huge bra and panties. The fat was folded all over, it was pretty nasty, but for some reason I got a hard on as she undressed. Of course she noticed. “You like my big tits and ass, huh? You are one sick fuck, even as I am about to hurt you, you are thinking about sex.”
“He is a sick fuck” Cindy chimed in. She came over and spit right on my face. Monique laughed and grabbed my balls and started massaging them – “Does that feel good? Answer me you little bitch, does that feel good!” I nodded and she laughed again. “Too bad” As she said that she gave my balls a hard squeeze and my body cringed. The pain was so bad up in my gut, that I came near to tears. Monique then took more rope from her bag and tied my balls real tight. I was in so much pain that I never even heard Monique ask me a question. “Well, if you don’t decide, I guess that mean both, huh?. She went back to her bag and took out a bag of binder clips. She gave a handful to Cindy and kept a handful for herself. They slowly placed 6 clips on the underside of each of my arm. At that point, tears came from my eyes, I was crying from the pain. “Oh, Sam” Monique said. “You should have thought of this yesterday when you were so aggressive. The second option of her question became apparent when she went back to her bag and pulled out a paddle. “See, I would always choose the paddle, because once it’s done, it’s done. Those clips don’t come off for a while. But you must really like this, you asked for both and your dick is still hard!” She laughed again. She railed the paddle 20 times on my right thigh and I actually went numb for that last few it hurt so bad. She circled the bed and whacked away 20 more times on the left thigh. My thighs were bright red now and I was sobbing from the pain.

“Oh, crying like a little baby. This will all be over soon, Sam. You will know I am through with you when I finally cum.” With my balls tied up and my arms in pain, I could only sit and listen and try not to move to much. She took off her bra and mounted me with her humongous tits hovering over my face. “Don’t you want to clean him off first, my pee is still on his face”, Cindy said. “Oh, I almost forgot!”, replied Monique. She then moved up to straddle my face with her disgusting fat cunt and peed all over my face. It smelled so bad and went up my nose and into my eyes. “Now, where was I.” Monique again got in position with her tits over my face and proceeded to smother me with her flesh. Almost a minute passed and she sat up as I tried to catch my breath by breathing through my nose. She repeated this a few times and I was getting light-headed. She then scooted up and again put her giant pussy over my face and proceeded to sit down on my face and rub her clit against my nose. She started to get wetter as she kept rubbing herself into my face for 30 seconds or so and then release to let me get some air. Eventually she got off of me and said she would take the ball gag out of my mouth but I had better not scream or I would be in for a longer night. She took the ball gag out and explained that she wanted to hear me moan as I tasted her pussy. She straddled me again and sat on my face as I tasted her clit. She rode on my face for a few minutes as I moaned in pleasure, trying to get her to finish quicker. Eventually, her body flexed and the full weight of her torso came crashing down onto my jaw as she came. She got off me and stuck the gag back in my mouth. “Thanks, Sam, that was pretty good”. She proceeded to take the clips off of my arms and pack up her stuff. She put on her clothes and headed out. It was near 11:30 now and I didn’t know what was going to happen next. Cindy looked at me and smiled and said that I would remain tied up for a few hours until she got back. Then she left and I was alone in the room, at least she had left the TV on.

I awoke as someone was trying to get in the room. The clock read 2:44 and I had fallen asleep. I was covered in piss and the dried cum from Monique and saw that Cindy had walked in with two men. “I’m Chris”, the bigger one said. The little guy said his name was Chris. I was hoping they were just here to let me out and make sure that I didn’t do anything to Cindy, but they quickly dispelled that notion as they stripped down to their underwear. The little Asian guy quickly laid on top of me and started to kiss my neck and chest while grinding his body up against my balls. I was completely grossed out but also completely helpless, I cringed at the thought of what was going to happen next. As Tim kept kissing me all over, Chris appeared at my head with another type of gag. This one had a dildo on the end. Chris explained, “I am taking out your ballgag and I am going to put this one on you. If you scream, you will be severely punished.” As soon as he took off my ballgag I let out a scream for help. As soon as I did, I felt the crushing blow of Tim’s knee ramming into my balls and the pain shooting up into my stomach. I cringed and the gag was put firmly over my mouth. “I told you not to scream. We can keep you here as long as we like and the more difficult you are, the longer we will stay. If you thought that shot to the nuts was bad, just try something again and you won’t know what hit you – Capice?” I nodded as the pain began to subside. Tim began to rub my nuts with his hand and as I got hard, Chris laughed, “He likes it, Tim, keep it going, but don’t let him come yet.” Chris took out some lube from his bag and rubbed his hand up and down the shaft of my dildo-gag. Tim then got up and proceeded to straddle my face and fucked the dildo. Up and down, his ass was getting closer and closer to my face. He was moaning and rubbing his tiny dick as he fucked my face. Faster and faster, he kept going and then he came – the cum shot up and landed on my nose and face. The rest dribbled down his cock and onto my face. He then got off and wiped the come on his hand onto my forehead. Chris then started to untie my legs. “Now Sam, once you cum, we are going to leave. The more cooperative you are, the better chance you will have to cum. I am untying your legs, and you better not kick or squirm, understand?” I nodded and knew that even if I were to scream for help and someone came to help, there was little chance that I would be spared from whatever they intended to do. My legs were untied and they replaced this with shackles and a bar that fixed my legs fairly wide apart. They then untied my arms and pulled me up. They asked me to turn around and Chris slapped my ass a few times. That’s a beautiful ass Sam, now I want you to bend over the bed and put your ass in the air. I bent over the bed and I knew what was coming. There was a few seconds of silence and I could see from the mirror that Chris was rubbing his cock to get it hard. His dick was big and I knew it was going to hurt as nothing had ever been in my ass before. He spit on his fingers and rubbed my asshole just a tiny bit to loosen it up. I looked up to see Cindy sitting in her chair just looking at me and smiling. She knew she was about to have her ultimate revenge and looked me straight in the eye and winked. Seconds later, a thrusting into my asshole gave me a burning sensation. I yelped in pain and Chris was thrusting his dick in my ass. The burning sensation was still strong as Chris mentioned that I was really tight. Tim was standing near Cindy and rubbing his cock which had started to get hard again after he had already come on my face. The pain from behind got stronger and Chris said “You are loosening up now, soon I’ll have my whole dick in there up to my balls.” Fear ripped through me as I imagined the pain, I already thought this was his whole dick! “I want to hear him sobbing by the end”, said Cindy. “Whatever you say, ma’am”, said Chris as he pushed everything into my ass. His big dick was thrust so deep in and it really started to hurt – as he kept thrusting and thrusting the burning got so bad that Cindy got her wish and the tears started to well up in my eyes. As he kept going, my nose started to run and I started to sniffle and sob. Cindy had a huge grin as she looked at me. I didn’t know what was going on anymore as I was in so much pain and just wanted to be done when I felt an extra something up my ass. It was Chris’ cum and as he pulled out (which caused some pain as well) the cum dripped out from my ass. “Now it’s your turn, Sam. Lie down on the bed and we want you to jerk yourself off.” This was the easy part I thought, and then I would be finished. As I started to masturbate, Tim came up next to me and started to kiss my neck and nibble on my ears. It became increasingly difficult as this man whispered into my ear how sexy I was and how he wanted to take me home and suck my dick. He then stuck his tongue down my throat. My dick started to go limp as I felt his stubble on me as he kissed me. He pulled back and said “You better kiss me back you sexy piece of ass, or you won’t come for a while.” He kissed me and I stuck my tongue into his mouth. As our tongues slipped around each other, I started to try to imagine that this was Cindy. After a few minutes of kissing Tim, I finally came. Tim got off me and stood up and started to get dressed. Chris removed my restraint and packed it away. Cindy stood up to leave. “Bye, Sam. Good luck. It’s too bad it didn’t work out.” She walked out the door, I would never see her again.

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