The Challenge

Caitlin lived in the apartment next door, on the 15th floor of a highrise complex in Philadelphia, overlooking the clock tower of Independence Hall. She didn't work, so it was obvious her parents were paying her rent. At 21 years old, she was 15 years younger than me. She was a short blonde, 5'3" and very curvy. She wasn't skinny, but she also wasn't fat. She was thick, just the way I liked. Her tits we big, easily DD, with a beautiful plump ass to boot. And she knew how to dress to accentuate her figure. I fantasized about her often, but because of the age difference, I never approached. Sure, we'd share exchanges in passing, but nothing more than that. And she never called me by name, always just 'Lieutenant'.

It was Halloween and I had just finished a long 12 hour shift. As I arrived at my door, I'd noticed Caitlin was having a party. There we two people at her door, dressed as Mario and Luigi. As I was putting my key in the lock, Caitlin looked over at me and gave a smile and wave. Mario and Luigi slipped passed her and into the apartment. She closed the door behind her and scurried over in my direction, with a White Claw in her hand.

"Hey Cait. Partying tonight, huh?" I said, as I pushed my door open.

She was dressed as a schoolgirl, wearing a short blue and green plaid skirt, white blouse, white knee high stockings, and blue and white saddle shoes. Her blonde hair was in pigtails and I could see her black bra through her blouse.

She looked at me and smiled. "It's just a small get-together with some friends. You should stop over for a beer," she said, excitedly. I could tell she had already put on a slight buzz.

"I don't think I should," I declared. "I'd feel like the creepy old guy around everyone your age," I said with a nervous chuckle. "...besides, I was challenged to do a Sober October by some buddies, and I made it this long."

"Sober October?", she laughed. "I could never do a challenge like that!" as she took a sip from the drink in her hand.

I looked at her and smiled. "I didn't think I could either, but I'm not one to back down from a challenge." As I started to walk into my apartment, she had followed.

As I emptied my pockets on the table by the door, Caitlin started talking. "Well, if you won't come have a drink, can I at least offer you some food? There's plenty next door," she says.

"You know what, that sounds nice. I'm going to take a quick shower, and then I'll swing by for a plate," I say.

She laughs and sarcastically exclaims "No, no. I don't want you to be the creepy old guy just showing up for food." She points towards my kitchen, "Leave your door unlocked and I'll drop something off while you're showering."

"That sounds good, I'll do that," I say. "Okay," she quips back, as she turns and heads for the door. Before exiting she turns back and looks at me with a devilish, almost sinister look in her eyes.

"Hey Lieutenant," she says quickly; "I challenge you to do No Nut November!" I look and raise an eyebrow. "You said you can't back down from a challenge, so now you HAVE to do it!" She laughed to herself and left my apartment, closing the door behind her.

"No Nut November?" I thought to myself. "I would never be able to survive the whole month without blowing a load, and she'd have no way of knowing if I did." I shook my head and headed for my bedroom, ready for my post-work shower...

########

I step out of the shower and grab my towel, drying my body. I walk to the sink and wipe the fog from the mirror, looking at myself. My 6'2" frame stares back at me, showing a bit of a gut. Dad bod, as it's called these days.

I open the bathroom door and start walking down the hallway to my bedroom, pulling the towel over my head to dry my hair as I walk. As I enter the room, I hear a voice.

"Took you long enough, Lieutenant!" she says.

I stop in my tracks, completely startled. "Jesus Christ, Cait!" I shout, dropping the towel to cover my exposed dick. "What the fuck! What are you doing?"

Caitlin is across the room, on her knees, sitting on the heels of her feet. Her blouse is open and she's no longer wearing that black bra. Her tits are covered by the opened top, but barely. She falls forward onto all fours and starts slowly and seductively crawling towards me, her large tits now fully exposed. I see her reflection in the full-length mirror on the closet door, and see that she's not wearing anything under the skirt. She sees me looking passed her, stops crawling and looks over her shoulder at the mirror behind her.

"You like what you see, Lieutenant?" she whispers, as she slowly runs her right hand down her body between her legs. Her middle finger runs up and down the length of her freshly shaven pussy, before she slides it inside. Pulling it out and bringing it to her mouth, she locks eyes with me. "Mmmm, I taste good." she whimpers.

I'm caught off guard. I don't know what to say, as I stand there like a statue; my bulge slowly rising beneath the towel.

She begins crawling to me again, stopping at my feet and pushing herself back to her knees.

"You know," she says, "as I got back to my apartment, it dawned on me that if you're going to do No Nut November, you have to start the month empty."

I look down into her piercing blue eyes as she bites her bottom lip. She reaches her hands up and places them on my chest, slowly running them down my body. As she inches her hands lower, she snatches the towel and tosses it aside in one fell swoop. Her eyes gaze down at my semi-erect cock.

"Oh my fucking God!" she says, gripping the base of my cock with her thumb and forefinger. "I think we're both going to enjoy this very, very much." she says, just before giving a little flick of the tongue to my tip.

She looks up at me, bites her lip again and starts to beg.

"I really REALLY want to give you a blowjob right now. Can I? Can I suck your dick, Lieutenant? Can I show you what a dirty little slut I am? Can I show you how badly I want your fucking cum?"

"Puh-pluh-please" was all I could muster, still in shock at the events taking place.

She gently kisses the side of my now fully hard cock, just at the base, running her tongue across the underside. "Do you want to see how nasty I can be?" she asks, before kissing my cock again. "Do you want to cum all over my pretty little face?"

I can't even speak. I'm dumbfounded, but in a good way. She begins to tease me, running her tongue up and down my length, and down to my balls. She lightly licks on them before looking up at me and asking, "Are you going to tell me to start sucking, or are you just going to have me tease you all night?"

With that, she spits in her hand and begins stroking my cock. She brings her mouth to my balls, taking one of them in her mouth and pulling on it with her mouth.

"You really are a nasty little slut, aren't you?" I ask. "Try me" she quips back.

I push her head back and grip my throbbing member, slapping it across her face. Instinctively, she opens her mouth and sticks her tongue out. I slap it against her tongue a few times as she lets out an audible "Mmmm".

I lean in and spit in her mouth, and she takes it. "That's more like it!" she exclaims. This girl is a freak, and I'm loving it.

I grab my cock and put my hand on the back of her head, shoving it down, forcing my entire length down her throat. As I pull away, a string of saliva attaches my dick to her tongue. "No gag reflex!" she says with a wink.

I immediately grab her head and start fucking her face fast and hard, holding her head down every so often. The drool dripping from her mouth runs down to her tits, her blouse soaked. I pull away and walk to the bed, and sit down, sternly telling her, "Start sucking."

She crawls towards me and grips my saliva-soaked cock with both hands. With one hand at the base and one hand on the shaft, she takes me into her wanting mouth. She bobs her head up and down while using one of her hands in a jerking-twisting motion. All I can do is lean back onto my elbows and watch. She's a pro. It's like se was born to suck dick. She masterfully sucks me up and down, continuing the strokes with her hand, moaning out loud with every downward motion of her head.

She stops sucking and slowly starts licking the underside of my shaft up and down, and then makes her way to my balls. One at a time, she takes them both into her mouth, before inching her way lower. She licks up on down my taint, and without warning, she puts her hand under my thighs, raising my legs. Her tongue instantly goes to my puckered asshole, licking it gently, twirling her tongue around in circles. Her hand reaches up and grabs my cock, stroking me while she continues to rim me. Every time I think she's going to stop, she doesn't. She just keeps hungrily eating my ass.

She eventually stops and looks at me. "Are you going to give me a big load, Lieutenant?" she asks desperately.

I give her a nod and assure her, "Yes I am, slut."

No sooner that I say that, she goes right back to blowing me. Using her hands and her head simultaneously, eagerly sucking, working hard to get her reward.

I feel the orgasm building inside me, and I quickly push her head away and stand up in front of her. She sits back on her heels, tilting her head back and opening her mouth. And then she begs. And begs. And begs.

"Fuck yeah, Lieutenant! Give me that fucking load! Give me every fucking drop! I need it! I. Need. Your. Fucking. Cum."

I start vigorously stroking myself, before I finally explode. An eruption of cum shoots from my head, splashing her in the face. "Fuck yes!" she cries out. "More! More! More!" she screams as rope after rope of hot, sticky jizz blasts her face. I expel what seems like a pint of warm goo, before crashing down on to the bed. I look at her and I've never seen so much cum. She's covered. There's a stringed glob dangling from her chin. She raises her palm to catch it and brings it to her mouth, licking it from her hand. She opens her mouth, showing me what's on her tongue, but she doesn't swallow. Instead, she takes her hands and uses her palms and fingers to scoop everything off her face and into her mouth.

Tilting her head back, she opens her mouth again, making sure I see that she has a huge mouthful of nut. She moves her tongue around inside her mouth, the pool of jizz dancing in her throat. She eventually closes her mouth and gulps it all down, then opens her mouth again to show me that it's empty.

"Wow, you really are a dirty little cumslut, aren't you?" I ask.

"Yes, and I want to be YOUR dirty cumslut, Lieutenant. You haven't seen anything yet"

She stands up, her face still glistening with the remnants of cum, her blouse drenched in spit and saliva, her hair a mess. She begins to button her shirt before I stop her.

"If you want to be MY cumslut, as you claim, then you'd better do as I say."

She responds, "Yes, Lieutenant."

"Keep the blouse open, don't wash your face. I want to watch you walk back into the party looking the way you do" I say, in a serious tone.

"As you wish, Sir" she answers. "But don't forget... No Nut November. Think you can last?"

I laugh.

"It'll be worth it if you do, I promise" she declares, as she makes her way to the door. I follow her as she exits, watching her walk to her apartment. As she opens her front door, she looks back at me with a smile, shoots me a wink and blows me a kiss. I just wish I could see the faces and reactions of her visitors as she came back to the party so disheveled.

And with that, No Nut November was on. For the next 30 days, she made my life hell. Every day she would send me a new dirty picture, or sext me something kinky. But I survived...