Men I’ve Loved Fucking
The Other MILFs — Lee Again (Probably)
I woke up because someone was pulling my shorts down.
In previous chapters, Tori regaled her therapist with selected highlights of her extensive sexual history in a vain effort to provoke him into adding his cock to her collection. He chose not to fuck her, but to hold out the promise that he might in future… if she kept coming to see him, confessed her slutty sins, and accepted whatever penance he assigned. This is part 25b (between “Quentin” and “Santa”) of what was meant to be a 26-part episodic series… but I couldn’t give up on the character. Each chapter is a stand-alone story. You can find them all here…
God, I’m an idiot! I thought I was playing Quentin for five weeks by teasing him with my filthiest stories… then last week, when I eventually got my hands on his cock, he teased me with it.
My first thought was that he’d been playing me all along, but it was even worse than that: I’d been playing myself. I got fixated on his cock, then I established a routine where, every week, I’d sit in his office and spend an hour staring at him, while I got aroused by my own memories and the thought of him fucking me.
It’s a Pavlovian response now. I got tingles in his waiting room, and when I entered his office my cunt fluttered, even though I know he’ll go nowhere near it.
He’s my confessor now, not my therapist. I’m supposed to turn up with one story then spend the rest of the hour making my ‘penance’, whatever that means. I have to assume it’ll mean anal or a blowjob, because that way, I’ll need to come back next week, and every week, in the hope he’ll eventually let me complete my alphabetic collection with his Q-cock. I don’t know how long I’ll tolerate that arrangement, but it had better end in a proper fuck one day.
At least Quentin’s out from behind his desk again. Last week he put a barrier between us, but now his comfy chair has returned, at ninety degrees to mine, within touching distance.
I don’t want us to be at ninety degrees, though. I expected to be facing him, like last week, with my short skirt riding up and my knees apart. That’s why I’m not wearing knickers again: I hoped I could at least torment him for a while before he used me.
I almost didn’t come back this week, but he doesn’t seem surprised to see me.
“Welcome, Tori. Please, sit. Do you have a confession for me?”
“Yeah, doc. Quentin, I mean. Yes, I have one. Do you remember Lee?”
“An old school friend of yours? You and he have a sort-of ‘free use’ arrangement, where you’re sexually available to him at any time, unless you don’t want to be?”
“That’s him. This is from a few years ago, after I’d broken my ankle falling off a motorcyclist.”
“You crashed?”
“We weren’t on his bike, Quentin. We were on my bed. I got over enthusiastic and fell awkwardly. Anyway, I was going to be in a cast for a few weeks, and I needed help with showering and other stuff, so I asked Lee if he’d be able to pop over sometimes to give me a hand.”
“To aid you in the shower? I imagine he was eager to assist.”
“Believe it. I gave him my spare key, in case of emergencies and so I wouldn’t have to hobble to the door and let him in every time I needed him. One evening, he came over to help me balance while I showered with one foot dangling outside the bath.”
“Couldn’t you have just sat on stool or something, with your cast resting on the rim?”
“And miss the chance to tease Lee? Of course his hands were all over me, helping me ‘wash’, but I wasn’t in the mood so I shut him down. Then I felt bad about flaunting my body at him, so I asked him to stay for a while. I put my pyjamas on, cracked open a bottle of vodka, rolled a fatty, and we got wasted together. It was a great night: we listened to music, talked shit about our friends, told stupid jokes… no sexual tension, just mates having fun. It was like we were teenagers again, back before he fucked me the first time.”
Quentin unzips his fly, pulls his limp cock out, and starts stroking himself. “I see. Will you be getting to the sex part any time soon?”
Rude! “I was about to. Eventually we were both struggling to stay awake, so I sent Lee stumbling home, and I crawled off to bed. I’d got into a habit of sleeping on my stomach with my cast propped up on cushions, and that night I was asleep the second my face hit the pillow. I don’t know what time it was when I woke up. It was still dark, I know that, and I know I only woke because someone was pulling my shorts down. A man was lying over me, his weight pressing me into the mattress while his greasy cock probed between my buttocks.”
Quentin raises an eyebrow. “It was Lee, I assume, using his key and his free use privileges?”
“Yeah, that’s what I assumed too. I still wasn’t in the mood, but I felt bad about denying him earlier, and I was drunk, so I just let him get on with it. His cock slid around for a second, blindly trying to find the hole. Then he connected, and suddenly his entire length was in my ass.”
Quentin’s perfect six-inch cock is fully erect now, his fist wrapped around its tempting solidity. “Go on.”
I don’t want to. My cunt tingles at the sight of his foreskin sliding over his knob — covering and revealing, covering and revealing — and there’s a hunger building inside me. A need. I don’t want talk, I want action.
But maybe unsatisfied desire is my penance?
“Not much else to say, doc. He fucked me. Slowly and gently, thankfully. Lee’s not a small man, but he was lubed, and I’d recently drunk a lot of eighty proof muscle relaxant, so I was feeling no pain. In fact, I think I dozed off at one point. I was definitely awake when he thrust hard, once, balls deep, then grunted and flooded my ass with hot cum. That kind of annoyed me, because I prefer him to use a condom, but I wasn’t in the mood for an argument. He withdrew, and as he crept out of my room I could feel his spunk leaking out of my ass, dripping onto my bed. I thought, he’ll have to come back and help me shower again. Then I must have fallen asleep.”
“And did he come back?”
“Yeah. I called him in the morning. He came over and washed me, then he changed my bedding. While he was putting the sheet in the machine, he asked me what the stain was. I don’t even know if he was joking. So, doc, that’s my confession. How do I atone?”
Quentin leans back in his chair, smiling. “The penance should fit the sin, I think. So why don’t you bend over my desk,” he stops stroking his beautiful cock long enough to point at it instead, “I’ll lube this up, and we’ll see if I can keep you awake.”
“No.”
He gives me a look that’s half-surprise, and half-expectation. “What, then?”
“If you’re going to fuck my ass, with the way your cock curves it’ll be better for me to lie on my back, with my knees on my chest.”
“Just as you sometimes fantasise doing with Niall while he punishes you for stealing?”
“You made more notes about my sex life than my psyche, didn’t you? But yeah, exactly like that. Except your little cock isn’t as scary.”
He heads for his desk, and I follow, pulling my skirt up around my waist. He takes a condom and a bottle of lube from his drawer, and as he prepares his cock, the cheeky bastard tries to switch back into therapist mode.
“Tori, I’m a little concerned about the numerous instances of dubious consent in your story. Free-use is a problematic concept of itself, but for Lee to fuck you while you were heavily intoxicated and still sleeping is worrying. He didn’t even use a condom.”
I hop up onto his desk, lie back in the foetal position, and expose my own perspective. “Quentin, I don’t care what you think about free-use: if that’s not your kink, don’t get involved in it. Also, I love being woken with a cock, I’ve had some of my best sex when I was hammered, and I’ve never had condom rules with Lee. If it even was Lee. But whatever: obviously I was a dreadful slut, and only your cock can cleanse my conscience. So get on with it.”
He finishes lubing himself up, and starts probing my asshole with a greasy finger.
I do want the beautiful, condom-clad cock that’s inches away from my butt, but he’ll get another piece of my mind before I take a piece of him.
“Anyway, doc, what about my dubious consent in this situation? You know how much I need your cock, that’s why you didn’t fuck me last time. You wanted me to come back this week, and every week, to blow you, or take it up the ass, in the hope you’ll eventually fuck me properly. I’m only consenting to anal today because you’ve made it a condition of giving me what I really want in the future. How questionable is that, exactly?”
Quentin stares at me for a second, expressionless, then slides the head of his cock between my labia so it’s pressing against my entrance.
It’s only disbelief that makes me say, “No!”
He smiles, says, “Yes,” then raises a single, questioning eyebrow. “Yes?”
“Yes!”
I’m glad he’s lubed. Watching him wank didn’t get me that wet.
He pushes — slowly and gently, thankfully — and I open up to him. My cunt complains a little, but I’m not listening: I’ve waited a long time for this, and I will not turn it away now.
He doesn’t stop pushing until he has to, until almost his entire length is clasped in my warm, tight embrace, and only my awkward position prevents him going deeper.
He saw my eyes widen as he entered me, and he checks in. “Is this okay?”
Okay? It’s better than okay. My collection is complete: I’ve got my Q. He doesn’t even have to cum to qualify… but it would be a shame to waste this opportunity.
“It’s fine, doc. I could have used a little foreplay, but keep going slow and I’ll catch up soon enough.”
He lifts my feet, easing them apart, encouraging me to wrap my legs around him and draw him closer, deeper. I hold him there, his perfect cock mine in its entirety, just for a moment.
His first withdrawal is as slow as his thrust. I feel every inch of him, every ridge and vein, as my cunt walls cling to his shaft, and that glorious curve drags his knob across my G-spot.
His second thrust is easier, my lube mingling with his now, my muscles relaxing, my cunt welcoming his unexpected intrusion.
I feel like I should be more involved, but a truly remorseful woman accepts her penance in silent, shameful atonement, so I rest my ankles on his shoulders, lie back, close my eyes, and let him do all the work.
He only speeds up a little as he feels my body’s resistance ease: he fucks me as though we have all the time in the world, and I’m glad I can’t see his clock telling me we don’t.
Every slow thrust sends a shiver through me, adds to the pressure building behind my clit, pushes me closer and closer to orgasm.
But I don’t want to come. If I do, I’ll be too sensitive and we’ll have to stop. I want him to cum. I want to feel him pulse inside me, deep inside, to know that I’ve taken everything his cock can give, to know my collection is truly complete.
“Fuck me, Quentin! Hard. Fast. Use me. That can be my penance for coming here today, for even thinking about submitting to your coercion.”
He doesn’t need to be asked twice.
He stops me as I’m walking out of his office. “Tori! I… I just wanted to say it was a pleasure to have you as a client. While this final session obviously can’t qualify as therapy, per se, I do hope it helped with your guilt.”
“For god’s sake, Quentin! I thought you were smart. I never had any guilt; I’m happy being a slut. Oh, and one more thing, before I leave: make sure you have a flavoured condom in your drawer for next week. I’ve got a face fucking story you’re going to love.”