Part 1
Sitting on my couch and looking at my phone, I find myself reflecting on an eventful Tuesday. This morning I broke up with my girlfriend of eight months, Lisa.
Lisa was a hair dresser that I had met when she was subbing in for my regular barber one day. I was in my mid-thirties and she was eleven years older. Despite the age difference, she took care of herself well. She was a 5’3″ natural redhead and had a pretty tight little body, small breasts, full lips, a tendency to wear a little more makeup than necessary and a smoky voice that I thought was sexy. I asked her out when she finished cutting my hair and things moved fast after that.
It started out as an intense relationship for a few reasons. She seemed like exactly what I was looking for – someone who knew what she wanted and wasn’t “high maintenance”. It also didn’t hurt that we were all over each other, all the time. It wasn’t uncommon for us to fuck a couple of times a day when we had the chance.
Things started to go downhill after three or four months. As she started getting comfortable with us as a couple, it became clear that she wasn’t as self-confident as she pretended. Turns out that she was actually remarkably insecure in many things. Our age difference, female friends in my life, our future, etc. That insecurity started manifesting more and more in drama that I just didn’t want to deal with.
At the same time, the sex life was cooling off. One thing I had overlooked due to the intensity of the sex was that, well, her pussy was really loose. It was getting harder to get pleasure from fucking her because the physical sensation just wasn’t there. I’m not saying it was like throwing a hot dog down a hallway but it wasn’t anywhere close to tight.
I had asked her early on in the relationship what she thought about anal. She told me she wasn’t into it and I reluctantly respected that. One night, about five or six months in, she was riding me and my cock came out of her pussy. She grabbed it to put it back in but rubbed it around her asshole to tease me a bit. I grabbed her hips and pushed upwards a bit and the tip slipped in. She froze but after a few seconds pushed down so that the head of my dick popped into her ass. She held me there for a bit and then pulled back out.
When she rolled onto her side, I wasted no time curling up behind her and pushing the tip of my cock back into her ass. She didn’t fight it so I slowly pushed myself into her, pausing when her hand gripped my thigh tightly.
I fucked her in the ass that night, which started a new pattern that I enjoyed quite a bit. We would start having sex and at some point be on our sides. I would fuck her pussy for a while and then subtly reach over and put some lube in my hand without her noticing. I would thrust harder into her and “accidentally” pull out. Grabbing my dick with the lubed hand, I’d get it slick and then glide myself into her ass.
That was the pattern for a couple of months. We would fuck vaginally, I would switch to anal and we’d go until I emptied myself in her bowels. Sometimes I could see her in a bit of pain, but that kind of turned me on. Either way, we never talked about it until one day, late in our relationship, she asked, “Why do we always have to have anal?” That conversation went downhill and I stopped fucking her ass.
So now we had sex I didn’t particularly enjoy combined with constant drama and insecurities. It culminated last night during a dinner party with two friends who had come over to my place for dinner. She lost her shit in the middle of the meal over some innocent comment someone made and I was mortified. To spare our friends the awkwardness, I suggested they leave early which they were only too happy to do. Once they had left I was furious but stayed calm. I told Lisa to go back to her place, I didn’t want to deal with her shit. She cried but she did what I said.
This morning when I woke up, I decided it had been the last straw. I packed all her things up in a bag and brought them over to her place on my way to work. She was stunned. She tried to ask why but I just said, “Are you fucking kidding after last night?” I left for the office and largely ignored the calls and texts from her that blew up my phone.
So now I sit here, chatting with the friends from last night to see if I can’t make it up to them and go out to dinner. For the first time in a while I feel pretty good about the future and am definitely confident that I made the right decision.
As I tap away on my phone, I hear the door to my fifth floor apartment open. Confused, I stand up and walk to the entrance where I see Lisa using her key to my place that I forgot she had. She’s tiptoeing in clearly knowing she shouldn’t be here. Her eyes are puffy from crying during the day and she’s used makeup to cover it up as best as possible.
“What the fuck are you doing here?” I ask loudly.
She jumps in surprise but recovers quickly. She walks down the entrance towards me as I back up. “I needed to come see you, this is a mistake Craig! We’re so good together, we can’t break up,” she exclaims.
“Breaking into my place, key or no, is not how you tell someone they made a mistake.”
She blushes slightly and puts the key on a nearby desk. “I just wanted to talk, make you see my side of it,” she says.
“I’m not interested in whatever you think that is. You need to go,” I reply.
Tears spring to her eyes and she rushes towards me, trying to hug me. Surprised, I fall backwards onto the couch with her awkwardly landing in my lap. I quickly push her off and she stumbles, trying to keep from landing on her ass on the floor. She ends up on her knees in front of me.
“What the fuck!” I yell.
“I’m sorry, Craig! I’m so sorry. Whatever I did, I’m sorry!” She’s almost in hysterics.
“I don’t care! This is so fucked up!”
She holds up both hands and closes her eyes as if to say “pause” and collects herself. She takes a deep breath then looks at me and says, “Listen, I know that things didn’t go great last night but I wanted to come over and make it up to you.” She puts a hand on my thigh.
“Lisa, what the fuck. This is so idiotic.”
She quickly moves her hand up my leg and grabs my crotch gently. My cock involuntarily stirs and she notices. She presses her advantage and moves closer.
“You really just don’t listen to what the fuck I say, do you?” I mutter.
“I think I can convince you to see things my way,” she replies with a small smile.
My cock is slowly enlarging as she softly strokes it through my shorts. I’m about as angry as I can recently remember but the little head is definitely not listening to the big head.
Finally I swat her hand away. “Enough.” I say resolutely.
“But-” she starts.
“Shut. Up.” I reply. “You think you can come in here and convince me to take you back with a bit of sex?”
Looking like she’s about to start crying again, she says quietly, “It’s all I could think of.”
I look at her for a few moments and a decision is made. “If I’m going to take you back, you’re going to have to work for it tonight. I’m not talking about a quick blowjob and everything is copacetic. You do what I tell you to do without question. If you fail, you’re out. Understand?”
She’s already nodding before I’ve finished my statement but there’s a tinge of uncertainty in her eyes. “I’ll do it. I’ll do anything. I can’t lose you, Craig!”
I sit back on the couch and think for a second. Finally, I say, “Get naked. Throw your clothes over there.” We both pull our clothes off fairly quickly and before long I’m back on the couch with my legs spread while she is standing in front of me expectantly.
“Get on your knees and blow me.”
She’s on her knees in a flash and has one hand around my dick. I’ve got a nice sized member, roughly eight inches and thick. It’s not a monster but I get no complaints.
She lowers her head to my knob and starts licking it. Before long it’s in her mouth and she’s swirling her tongue around me. Her head begins to bob up and down as she takes me about halfway. I sit back and watch her red hair bouncing up and down in my lap. She begins moving her hand in time with her mouth and lightly scratches her nails down my thigh with her free hand.
“Go deeper,” I say. She complies by taking in another inch. “Deeper,” I repeat. Lisa has never deepthroated me and I have no idea if she can. She stays at the same depth as if trying to think of something but she starts pushing further. I feel the back of her throat touching the tip of my cock and then she suddenly lurches up with a quick heaving motion as her gag reflex triggers.
She looks at me and I return her gaze. She looks back down and engulfs me once again in her mouth. She pushes down again and again I feel the back of her throat before she snaps away again. Tears pop into her eyes as she looks at my impassive face and goes back for a third try.
This time she tries to go slower and as I feel myself get close to the back of her throat, I take her head in both hands and push hard. Her hands snap to my thighs and nails dig into the flesh as I keep pushing her down. My dick is smashed up against the back of her throat and her stomach is making a heaving motion but I maintain the pressure. With a croaking sound emanating deep from within her, her throat suddenly opens up and my cock slides past the barrier. I can see her feet start beating against the floor and her body is twisting as I force her head down until her nose is pressed up against my pubic bone. I hold her there for a second until she pounds her hands against my thighs and forces herself up off of me. She sits back on her heels, taking huge gulps of air and is trembling. She looks up at me and her mascara has begun to run down her face.
“I don’t know if I can do that,” she says.
“You just did,” I reply.
“I mean… again.”
I look at her for a moment and simply say, “Lick my asshole instead.”
The change in direction catches her off guard. I coerced her to do this once while we were dating and it wasn’t something she enjoyed. That said, she seems relieved to not be swallowing cock so she leans back down. I rest my heels on the couch and tilt my pelvis under to expose my ass.
Lisa tentatively gets closer to my ass and slowly spreads my cheeks. I feel a soft, exploring tongue barely touch me and I snap, “You’re going to have to do a lot better than that.”
I hear a squeak escape her lips and soon feel her tongue slowly licking up and down my ass. It feels amazing. She is working up and down and I can tell from the moments that I can see her closed eyes that she’s not enjoying herself.
“Faster,” I say. “Deeper. Don’t be shy.”
She starts lapping at my asshole at a quicker pace, her tongue getting stiffer as she circles around the puckered surface.
“Deeper.” I say forcefully.
She takes a quick breath and then spreads me apart further and slides her tongue into my anus, spearing it. She goes in and out, tonguefucking my ass. The nerves in my asshole are firing and I am loving it. My sphincter clutches around her tongue every time she thrusts in, trying to keep her from escaping.
Finally after a few minutes of this, I say, “Enough.” I let my legs back down and she pulls back quickly, happy to be done with the task at hand.
“Get on the couch, on your back. Feet up over the back of it.” She looks at me confused, not sure what I’m asking. “On your back, head hanging off of the seat of the couch.”
This is definitely not something we’ve done before so she’s cautious in getting into position but she does what she’s told. Once she’s in place, I crouch over her face and grab her head to stick her mouth back in my ass. Realizing what’s happening, she whimpers but starts licking again. I start riding her face, sliding my asscrack up and down, letting her tongue find every ridge in my asshole.
After a few minutes, I stand back up and say, “Now, deepthroat me again.” There’s a quick panic in her eyes but she doesn’t have time to respond before I’m already pushing my cock past her lips. She opens up and tries to take me all in. She puts her hands on my hips to try and control the pace.
When I hit the back of her throat, I wait a moment to see if she’s going to let me in. For a moment I think it’s going to happen but I stay locked out. In response, I start pushing. Her head has nowhere to go as it’s against the foot of the couch. Her hands grip my thighs tightly to force me back but I grab her wrists and force them to her sides and continue to push.
Lisa tries to twist her head to the side to escape but my thighs keep her in place as I increase the pressure. Finally with a popping sensation, my balls are suddenly sitting on her nose as my cock is buried in her throat. Her legs start flailing about and I pull back slightly. Thinking that I’m going to pull out completely again, she starts to relax only to heave again as I force my way back in. Soon I am fucking her throat relentlessly, every thrust greeted with a croaking sound coming from her mouth. Finally with a strong kick against the back of the couch, she is able to get me off of her, pushing me back enough for my cock to slip out of her mouth and for her to sit up.
Annoyed, I sit back down on the couch next to her. She is out of breath and panting hard. “Fuck…” she says. I look at her, eyes calm, and say, “Go to the bedroom and get the lube.”
Part 2
Lisa looks at me cautiously and makes no move to get off the couch. “We can just fuck right here, right now,” she says.
“Go. And don’t delay.”
Her chin drops to her chest and she pauses for a moment. She seems to make a decision and stands up. I watch her walk out of the room quickly, thinking about her tight ass as she goes. It had been a while since I’d buttfucked her and I was looking forward to it. I grab my phone and send a quick message to my friends apologizing for not being able to make dinner.
She comes back a little more reluctantly, resignation on her face, but she hands me the bottle of lube.
“Back on the couch, on all fours. Ass towards me, hang your head and arms over the back of the couch.” She follows instructions and is in position. I pop the lid on the lube and squirt a bunch in my hand. Although my cock is still slick with her drool, I coat it fairly well.
Using my index finger, I slide it into Lisa’s ass up to the second knuckle with one stroke. It’s a tight fit and the shock of it makes her involuntarily give a short scream.
She looks back at me with a begging expression on her face. “Why do you always want to fuck me in my butt? What’s so special about that?”
I look at her straight in the eyes and say, “Are you kidding?” She gives me a confused look back. I continue, “Your pussy is so loose, I can barely get any sensation out of it. It’s useless to me.”
She can’t cover up the shock of her reaction to this biting statement and she quickly gets angry. “My pussy is NOT loose! What the fuck are you talking about? You mother-” She starts to turn back towards me when I grab her by the back of the neck with my clean hand. I force her back over the couch as she struggles under my grip.
“Oh it’s not is it?” I ask heatedly.
“Fuck no it’s not” she shouts as she tries to free herself.
Looking at my lubed hand, I straighten out all four fingers and slide them quickly into her exposed pussy. I can hear a gasp from the other side of the couch.
“Do you think I could easily do this if you had a tight pussy?” I yell at her.
“Fuck you!” She exclaims.
“Fuck me? Fuck you!” I yell. I curl up my thumb and push.
Her body jumps but she stays in place thanks to my holding her down. She screams, “NOO!”
Ignoring her cries, I continue pushing, her pussy expanding around my fist until it pops in. I can feel the warmth around my hand everywhere as it bumps up against her cervix. This is something we definitely haven’t done before and I’m kind of amazed at the sight of my wrist disappearing into her cunt.
I can hear a combination of whimpering and sobbing on the other side of the couch as my hand turns around slowly inside of her. “THIS is why it’s always anal. You think I can get off with a pussy this big?” I pull my hand out with little consideration for her. She yelps in surprise and pain.
Without pause, I line my cock up with her butthole and push hard. I hear a fresh round of screaming as I thrust deeply into her ass until my hips are against hers, all in one go. I know it isn’t going to be feeling good for her due to not getting any warmup and not a lot of lube but I don’t care at that point.
Lisa is still screaming so I lean forward and wrap an arm around her throat, tightening it slowly. “Stop screaming or I will make you stop.” She bites down on her lip and quiets to a consistent stream of sobs. I release her throat and sit back, my cock still buried inside of her. Gathering up her long hair, I wrap it around my fist. I slowly slide out of her ass until only the head is still inside. Gripping her hair tight, I pull it hard as I thrust back in, yanking her head back as I slam back into her. To her credit, she doesn’t scream this time.
I slowly increase my pace as I plow her asshole. I eventually let go of her hair and she lays her head down on the back of the couch as I take her from behind. After a bit of time I realize that her attention is no longer on me despite the fact that she is grunting each time my cock pistons in and out of her abused asshole. I look to where she is focusing and realize that time had passed and it has gotten dark outside. With the lights on in the apartment, it makes the windows very reflective, almost like looking in a mirror.
“Are you enjoying watching your ass get fucked?” I ask her, panting as I continue to spear her tight hole.
“Ung… Nooo… Unnngh..” she says between grunts.
“Well maybe you need a better view then,” I reply. With that I reach my hands around both sides of her face and slip two fingers into each side of her mouth. Pulling back hard, I fishhook her fiercely, her mouth taking an ugly shape as it is deformed by my fingers. I turn her towards the windows, her gaping mouth beginning to involuntarily drool onto the couch as I continue to pound her butt.
“Is that what you wanted to see?” I seethe.
She whimpers in pain and her hands weakly scratch at mine to let her go but she seems to be running low on energy. I won’t lie, seeing her face all fucked up like that as I watch myself fuck her in the reflection turns me on even more. My thrusting becomes faster and more violent, her grunting getting louder.
I release her face and she quickly puts her hands to her mouth, trying to soothe the pain. That’s probably why she doesn’t feel me slide my arm under her throat again. I wrap my other arm over the top of her head and put her in a quick choke hold, all the while pounding her ass. Realizing what is happening, her hands leap to my arms, trying to pull them apart. She can’t get a grip and soon her hands are falling to the side, her head starting to droop in my arms.
I release the hold and continue fucking her ass. I wonder if I made a mistake in putting her to sleep because her asshole loosened, no longer clutching against my every stroke. But I don’t have to wait long as she comes back to consciousness with a start. Her sphincter clamps down hard on my thrusting cock and it pushes me over the edge. With one final thrust, I hold myself there as my cock explodes, shooting jets of cum deep into her bowels. My orgasm feels like it lasts for minutes as I pump round after round of seed into her ass.
Lisa collapses against the couch crying, no longer trying to fight. Her ass holds me in place until I finally pop out. I step back from the couch, my cock dripping cum onto the floor. “Get on your knees and clean me off.”
Still facing the back of the couch, her head slowly turns to me, confused. I grab her by her hair and drag her off the couch, roughly forcing her to her knees. I’m still rock hard and coated in cum, lube and ass juices. Her face twists up as she realizes what I am saying but there is no time for her to resist as I push my cock into her mouth. She makes a retching sound but that’s all it is.
Having learned from my previous experiences in the evening, I don’t wait for her to try. Instead I grab the back of her head and force my cock into her throat without hesitation. She starts panicking as I am thrusting in and out of her throat and she gets enough leverage to push me away and land on her ass, leaning back against the foot of the couch.
“Enough, please…” she whispers, cum dripping down her chin and starting to leak out of her asshole on the floor.
“Oh, you’re done then?” I ask, having to look past my hard cock as I look down on her. “Time to leave?”
More tears run down her cheeks as she sits silently. Finally she shakes her head slowly and says, “No… I’m… I’m not done.”
Part 3
By this time a pool of cum has collected underneath her. I look down at it and point. “Then lick that up.”
Crying, she slides to her belly, her tongue slowly starting to dip into the pool of cum from her ass. She begins licking it up and swallowing it. I step over her and sit back down on the couch. I rest a foot on her back while she finishes her task.
When she is done, she sits back up and looks at me wondering what is going to happen next. I pat my hip and say, “Climb on top.” She does as I tell her and straddles my hips. She takes hold of my cock and starts to line it up with her pussy.
“What are you doing? Did you learn nothing? Where does my cock go?” I ask angrily.
She whimpers but quietly says, “In my butt.”
“Correct.”
Lisa shifts her weight forward and sits down on my cock slowly, the tip starting to penetrate her ass. “Too slow,” I said, grabbing her hips and pushing down hard. She bottoms out in that thrust and cries out. She sits there as I start thrusting up into her ass and I suddenly feel tears starting to land on my face.
“Jesus Christ,” I say. “Turn around, I don’t need to see your pathetic shit.” She sniffles, wipes her eyes and nods. She starts to get up off of me but I hold her in place.
“I stay inside,” I say. Lisa awkwardly repositions her legs so she can turn while keeping my cock buried in her asshole. I can tell it is painful as she turns but she got there. She starts riding my cock and I am enjoying watching it disappear into her ass over and over. I can hear her whimpering quietly but soon she falls silent.
“Going all quiet on me?” I ask, slapping her ass. She doesn’t respond. Am I getting the silent treatment while she rides my cock in her ass? We can’t have that.
Grabbing her around the waist and burying my cock deep inside her, I push forward and stand up which makes her awkwardly have to lean forward to accommodate me. I use my momentum to move us toward the floor to ceiling windows.
“What are you doing?” she asks suddenly realizing that I have a destination in mind. I don’t respond and keep moving until I slam her up against the window. The impact makes her gasp and I continue pushing her up against it so that her whole body is pressed up against the window, impaled on my cock.
“Craig, no… I can see people down there on the sidewalk,” she says, starting to panic. I start thrusting into her again and reply, “I’m sure they can’t see us at this time of night.”
I fuck her ass with a renewed vigor, the force once again making her grunt with every stroke. Her tits are pressed up against the window and her arms are above her head.
“Craig, I think they can see, people are starting to gather!” she says in a high pitch.
“Don’t worry about it”, I say. That clearly isn’t what she wants to hear as she starts to use her legs to push back from the window. I am starting to get close, the audience turning me on, and won’t let her stop me. I grab her around the waist and lift her off of her feet, slamming her against the window once again. Her legs flail uselessly as I continue to pound away mercilessly at her asshole.
I look past her down below and can indeed see the gathering crowd. I know that we are too high up for anyone to recognize us but they could definitely tell they were getting a show.
Lisa, helplessly suspended against the glass as I ravage her butthole, starts to cry once again. The fact that the crowd has started to cheer tells me they think she is just as into it as I am. That pushes me over the edge and I drop her from my grip, pulling my cock roughly out of her ass. She lands on her knees and I pull her away from the window. I start stroking my cock and force her to turn her face up towards me. My dick erupts as rope after rope of cum splatters across her face, gets in her hair, eyes and mouth. She opens her mouth to gasp and I force my cock right back in even as I continue to spurt. I once again force myself down her throat and fire shot after shot of cum directly into her stomach.
After what feels like an eternity, I finally pull out of her mouth and collapse onto the couch. Lisa lays on the floor, her face looking like she’s just been in a bukkake video.
After a few minutes of catching our breath, Lisa stands up unsteadily and feels the streams of cum starting to drip off of her chin. “I need… I need to clean up…” she says, one hand unconsciously moving to her inflamed and gaping asshole.
“You need to get the fuck out of here,” I calmly reply.
I see a brief flash across her face of not comprehending the words that I said and then suddenly her eyes widen and her mouth opens in a large O shape. “WHAT? We had a deal! You said you’d take me back if I did what you wanted!” Tears spring up in her eyes again and quickly mix with the cum that she tried to wipe away.
“I said you had to do it without question. WITHOUT QUESTION. You failed. Multiple times. Get the fuck out of my apartment!” I yell.
“I’m not going anywhere!” She yell back.
I grab the pile of her clothes and say, “Get the fuck out or I toss these out the window to your adoring fans.”
Her face turns crimson in shame and anger and says, “You wouldn’t.” I open the window and toss her clothes out in one fast motion.
Lisa’s shock is instant. “What.. what the fuck did you just do?”
“Get out!” I say pulling my shorts on.
“I need clothes!” she shrieks.
“You had your chance bitch.” I grab her up by the waist as she kicks and screams and hits at me. I open the door and throw her out, her naked body slamming against the door across the hallway.
“NO!” She screams.
I slam the door in her face and lock it.
She starts pounding on my door as I watch through the peephole. The door across the hall opens and my fat, creepy neighbor peeks out. Seeing Lisa naked in front of his door, he leers and opens his door wide. Through the door I can hear him say, “Hey, need a place to stay, sexy?”
Lisa tries to cover herself and runs to the nearby door to the stairs. I can’t see her after that.
Relaxed and satisfied, I drift back over to the window. The crowd has dispersed but I can see Lisa’s clothes down below. There are three guys down there, kicking at the clothes, clearly wondering why there were a bunch of women’s garments on the sidewalk and hanging in the tall bushes.
After a few minutes, I see Lisa, still naked, burst out of the building towards her clothes. The three guys are clearly stunned at the sight of her but recover quickly, grabbing some of her clothes before she can. She screams at them but they just laugh before one of them grabs her by the arms and pulls her into the bushes, his buddies following.
I sigh contentedly and sit back down on the couch. I send another message to my friends and ask if they are interested in a late night at the diner. I am starving.