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Dark Alley

By: Unrepentanthedon



Chelsay firmly latches onto my arm using me for balance as we leave the bar laughing, her heels clicking along the sidewalk. "I stayed up in the tree for like eight whole... freaking... hours! I was just too scared to jump down. Can you believe that?" Chelsay massages my forearm as we both chuckle. "And years later I had to laugh because when I went back to that tree it was only like three feet from the ground. I was such a silly little girl." A car honks off in the distance, causing Chelsay to turn her head quickly. Her long blonde hair skims across my neck causing perfume waft up at me. I look down to see her chest lowering and rising with each breath. When she starts telling a story she often forgets to breathe and now her little lungs are trying to catch back up. 

She is wearing a tight, low cut shirt that hugs her breasts together pushing them out at me. And in that moment I can feel my palms getting sweaty and the muscles in my shoulders tense up. Licking my lips I watch this beautiful blonde out of the corner of my eye. Even in her heels she is still much shorter than me. Her skin almost glows in the dim street light. And finally I just can't take it. I pull Chelsay into me which forces her to meet my eyes. I feel her body get a little weaker. Smiling out the side of my mouth I ask, "Well, then how did you get out of the tree in the first place?" 

Looking down, she answers into my chest, "Actually, my dad had to come find me. He helped me out. It was a good thing he did. At that point, I had decided I was going to live in the tree forever; a completely reasonably life choice at the age of eight, I think." 

I slowly brush her hair back behind her ear and for some reason she can't look away from my chest. I gently touch her chin lifting her head so she has to see I am looking right into her eyes. And then, I lean in so slowly. I press my lips against hers giving her soft little kisses until her lips part just slightly, allowing my tongue to find hers waiting for me inside her mouth. With my hands on her hips and my much larger body engulfing her something comes over me. I can feel my heart beating a little faster as my hands push harder into her back. We were not a couple who were big on public displays of affection but right then, I didn't care. 

Pulling away from our kiss I glance over my shoulder and then back at Chelsay. Her face is flush as she stands on her toes, waiting. I quickly look up and down the street and see sporadic pockets of people. It is a Thursday night and downtown is active but not too crowded. 

In her best little girl whiney voice, Chelsay asks, "Why did you stop?" 

Grabbing her by her hand and leading her away I say, "What makes you think I stopped?" 

I lead Chelsay into an alley. The further we get the less light from the street finds us until it is almost completely dark, and then I swing her up against a cold brick wall, pinning her there with my body. The bricks are coarse and no doubt digging into her back. But she doesn't protest and instead lifts one of her legs and wraps it around me, using it to hold me closer. Her chest is heaving when I slide my hand up her side, and then along the back of her neck into her soft hair. I grab hold and turn her head away so I can lean in and kiss her neck. Little kisses lead to big kisses lead to biting and Chelsay begins to moan softly as she rubs me through my jeans. 

"Do you feel that?" I ask almost whispering. 

"Yeah... I do." 

"That's how much you fucking turn me on. Do you feel how fucking hard you make me? Jesus you are so fucking sexy." 

"Yeah well you should feel what YOU are doing to ME." And with that Chelsay takes my hand and puts it under her skirt, pressing my fingers against her soaked panties. I can feel her lips through the soft lace as I rub her. I dive back into her neck kissing more aggressively as I make my way to her chest. Her hands touch my face, fingers tickling my coarse beard, and then she move her hands to my head gently playing with my hair; ever so slightly pushing me lower. So, I go lower. Lifting her shirt above her breasts I peel back the cups of her bra, exposing her perfectly formed breasts. I take one of her nipples between my lips, sucking softly and then nibbling a little. As soon as my teeth touch her skin she grips my hair hard and moans probably loader then she should. A noise pulls Chelsay's attention away from what I am doing. People on the street laughing walk by but none of them peer into the alley. I am quick to move to Chelsay's other breasts sucking and nibbling even harder on this nipple. And this brings her back to me. 

"God, Rob. Fuck! I love the way you touch me. I don't want you to stop but I am kind of a little scared. I really don't want to get caught like this." I can feel her breasts push into me with each deep breath and still her hands are in my hair pulling and tugging just a little but definitely urging me to go lower. So, I go lower. 

I kiss my way down to Chelsay's stomach as my hands slide up the backs of her legs under her skirt, squeezing her ass through her panties. "And what exactly do you think you are going to do down there, sir?" She asks skeptically. 

"What do you think I am going to do?" 

Chelsay shrugs her shoulders. "You think I am the kind of girl who lets guys go down on her in dark disgusting alleys?" 

I laugh, pressing my lips softly against her pussy through her skirt giving her one little kiss. "I think you are exactly the kind of girl who will let me go down on her in a dark disgusting alley." 

And with that I lift one of Chelsay's legs over my shoulder, massaging the soft skin of her thighs. "I'm going to stop you. You know that, right?" 

"We'll see," I say and then kiss her knee. 

"You're a good guy and I don't want to hurt your ego. That's the only reason I've let this go on for so long." 

Hands on the back of my head apply pressure pushing me further up her thigh. So, I go further. I kiss her again. "Really? You are worried about my ego? I think you might be the first girl to ever make that one of her concerns." 

Chelsay sighs deeply. And with that she grips my hair hard pushing into her. I continue my way up her leg until my lips are pressed against wet lace panties. She throws her head back against the brick wall. Groaning she lets out, "Fine! You win!"  

"I do, do I?" I quickly kiss my way back down to Chelsay's knee and she reacts just as quickly trying to push my head between her legs. "Wait, what are you doing?" She all but yells out. 

Again noises come from the street but Chelsay doesn't seem to notice. I glance up from below to see panicked eyes looking down at me, her teeth digging into her bottom lip. I carefully reach between her legs to push her panties to the side, exposing her soft wet lips. "I don't know," I say in an irreverent tone. "You might be right. We could get caught." 

"Ugh! You are such a fucking asshole. You would do that wouldn't you? You would stop once I give in." 

"No, here... let me up. We should stop. We can continue this at home." I move to get up but Chelsay locks her leg around my shoulder and holds me down. 

"I fucking hate you! God, I hate you so fucking much. You're gonna make me beg aren't you?" I just smile and shrug my shoulders again, kissing her knee softly. 

Here head sinks before she says, "Fine, alright! You win! Please..." 

"Please, what? I ask kissing her knee again. 

"Rob, please kiss down there." 

"Kiss you where, here?" And with that I kiss a little further up her thigh. Chelsay slides her hands behind my neck and pushes. "No," she whines. "Kiss my pussy, PLEASE!" 

I kiss further up her thigh. "How bad do you want my tongue inside you right now? How bad do you want my tongue on your clit?" 

"Oh my god, Rob! I want it so fucking bad! Please just put your fucking tongue on my pussy already. This is killing me! Just do it. I will give you anything you want. Please!" 

"Anything I want?" 

"Yes, I am yours. Just please lick me just once. That's it. That's all I want." 

And with that I take my tongue and find the bottom of Chelsay's pussy. Slowly I run the tip of my tongue between her lips parting them, tasting her, pushing my tongue inside against smooth skin, moving higher and deeper making my way up her pussy until my tongue finds a tiny little nub. I give one quick flick. Chelsay throws her head back and almost screams, "More! I want more!" So, I give her more. 

I move my tongue around and around her little clit, she cries out "Please, don't stop. That feels amazing," my tongue moving in slow big circles, around and around, on her clit and then off her clit, her hands pulling my hair, "please go faster, please!" and still I keep moving in slow big circles, her hips grind in unison with my tongue, around and around pushing down into me, her moaning getting louder, my hand holding on to the leg wrapped around my shoulder, massaging her thigh, licking her clit a little faster now, "Yes that's it. Please, more. God, baby, you own that pussy! It's all yours! Please, I want more!" my other hand making its way up, sliding a finger inside her pussy as my tongue moves faster, around and around, on her clit and then off your clit, in faster little circles, juices dripping on to my face. 

It is then Chelsay opens her eyes and looks out onto the street to see three man standing there watching us. Looking right at them she says, "Oh God, your finger feels so fucking good inside me. Keep going, please." So, I keep going. Holding my tongue on her clit, shaking my head back and forth, getting faster and faster, her hips violently grinding on my face her nails digging into my scalp, her back slapping against the brick wall as her body convulses. She lets out one long groan that gets louder and louder, "fuuuuuUUUUUUUUUUUK!" I pull my tongue off her clit and Chelsay reacts by yanking my hair. I press my tongue on her clit and shake my head back and forth again. "Yes that's it don't stop!" Her grip on my head loosens and my tongue retreats back into my mouth. With both hands she yanks even harder this time, and I thrust my tongue up inside her gushing wet pussy. "FuuuuuuuUUUUUUUUK!" Moving her pussy up and down on my tongue my mouth fills with her juices as she comes, her body convulses violently, her heel digs into my back, as she cries out something utterly incoherent. 

We are both silent, except for Chelsay's gasping for air. Her grip on my head is still tight as if all the muscles in her body locked up at the same time. I start to pull away and just the slightest touch makes Chelsay's overly sensitive body squirm. I carefully lift her leg off my shoulder and place it on the ground, kissing her knee one more time. And even this makes her squirm. Standing up I kiss her sweat beaded forehead, and then I kiss her lips. Chelsay's mouth open's wide and her tongue swirls around my mouth and over my lips as she tries to taste as much of her juices as she can. Finally, I pull away. And just as I had led her into the alley I take her by her hand and lead her out, out past the crowed of people that had stopped to watch us. Chelsay can't help but giggle as she avoids eye contact with all the people. I wrap my arm around her as if to shield her from our audience massaging her shoulder with my hand to let her know, everything is OK.

Dark Alley Hardcore Strap-on Femdom



I'm in a dark alley very tired and not feeling like doing much. I am suddenly knocked out and overpowered. I wake up with nail polish and 5 inch stiletto platform heels on with my hands tied behind my back and my feet tied with a foot-long chain. I also have on lip gloss but cannot tell from the tape over my mouth.

I lean against a wall and use my legs and the wall to unstably get to my feet and stand in the 5 inch stilettos with great difficulty. As soon as I get to my feet someone pushes there body against mine and pins me to the wall, whispering in my ear, I can tell its a women saying, "You should be careful in the dark, and be more aware. But I'm thankful that you weren't tonight cause you're gonna be my little bitch *giggle*." 

As I am naked except for the heels, I feel something rubbing against my ass. The women's sensual voice calmed me down and I was relieved that I wasn't gonna be raped by some guy, but I freaked out and tried to get away from her but being very strongly restrained and extremely tired I was helpless against her surprising strength. 

She says aloud, "Turn around so you can get a good look at what's gonna happen. But I'll warn you, if you do something to piss my off like try to run away, you will regret it a lot." I slowly turn around while trying to balance in the heels and see the most beautiful woman I could imagine. My penis, already semi-hard from her being pressed against me goes fully erect when I take in all of her beauty. "I see you that you enjoy the view.

That's good because you may not enjoy what this beauty is going to give to you." I look down and notice a large strap-on attached to her naked body, looking about 7-8 inches long and 2 inches wide. My eyes grow very large and my heart sinks in fear as I realize what is going to happen. 

"Oh my God I love that look on you face, it makes me SO WET *giggle*." She looks my directly in my eyes and says with a smile, "I'm going to take your manhood and make you feel like the little bitch you are. It's going to hurt you so much and I will get so much pleasure from your pain." She then forcefully turned me back to the wall and made me bend over. The heels were not making my position more comfortable. As if reading my mind she said, "Do you like the heels and nail polish effect? I think they make you even more feminine and it turns me on." She stabbed a finger into my unready, unprepared asshole and as a cried out from the pain and shock said,"Wow, you're so tight! It's really obvious that you've never had anything in here before. I'm getting so wet knowing how much pain you'll be in from my big dick *giggle*! And you're yelling already? 

Wait till I really start to fuck you..." She pulls her finger out and I desperately think of some possible way to get out of my predicament, to no avail. She then rubbed the strap-on up and down my fearful and helpless asshole. It suddenly stops right in front of my hole, and my chest is pounding as I try to brace my self, relax, and think happy thoughts. 

She then says,"I don't care if you relax or not, cause with the way I'll be pounding your bitch ass it won't matter *giggle*!" After this, she plunged the strap-on all the way inside of me with extreme force and I yell at the top of my lungs and try to squirm but am helpless and under her control. She does not stop or rest for a minute but keeps pounding me and as she is, removes the tape from my mouth to make my semi-concealed yells of pain very loud and a magnet for any curious passerby. 

Though it was late at night, there was bound to be someone around. And as I continued to yell in the most excruciating pain and as I can faintly hear her giggles from her amusement and her moans from arousal, I note a women that looks to be about 22 appear. To my extreme humiliation, she covers her mouth and gasps at the sight before her. She shows no sign of trying to help or flee, however, but fascination. 

She comes closer and I notice that she is rubbing around her vaginal area, and with closer inspection, that she is fingering her pussy while watching me being raped and in excruciating pain! I lose hope, masculinity, and could not be in more pain or humiliation. At least that's what I thought until my rapist finally stopped. The pain however, did not cease and my ass was on fire and I still screamed in pain. 

She walked over to the voyeurist and they had a 10-second long conversation. To my dismay and horror, the women came over to me both wearing strap-ons! And the new young lady had one just as big as my rapist! They smiled and giggled evilly as I realized that my seemingly worst-possible-scenario had just gotten worse. My original rapist began raping my ass again just as I thought I could stop yelling from the barely diminishing pain and it hurts even worse this time because my ass is sore and was closing back up! As I yell the new women comes and shoves her strap-on into my mouth and facefucks me through my cries of pain.

At this point my humiliation and pain was so deep I just wanted it all to be a dream. But it was very real as I was forcefully fucked from both ends. After about 10 minutes of this and me still in just as much pain as the start, I hear my rapists cumming from the arousal of my pain. I think, "Finally this is over" as they stop, although I am still in pain and in more humiliation than I thought possible. 

As the ladies step back and I immediately fall to the ground, with my last breath and energy I say, regrettably, "Now please go away and leave me alone. You've had your fun it's over." The ladies looked at me and just laughed and simultaneously said, "It's not over until we're done." 

My original rapist begins to stroke my cock as the other gathers their toys and clothes to prepare to leave when she is done. I think to myself that I will at least get some pleasure out of this. And am overwhelmed with deep and vast emotions as the woman takes my entire cock entire her mouth. After only 10 seconds of this treatment, I was nearly bursting. She senses this and takes her mouth, hands, and every kind of contact away from my cock immediately and I am left in horror with a throbbing cock, longing for release.

As both the ladies giggle she says to me, "Don't worry I'll give you a little pleasure since we enjoyed you so much." She then starts back with her treatment and sucks me and I immediately cum more forcefully and with all of the energy in my body I felt more pleasure than I have ever experienced. She swallowed it all and smiled as I immediately went to sleep after the intense pleasure.

The two ladies left me there tied, in heels, naked, with nail polish and emasculated. They walk off giggling happy as ever and in conversation as I try to sleep away the pain and humiliation. 



Dark Alleys are Dangerous