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."
