The Other Job - The Virgin

Info BenRosewood
03 Mar. '20

I take one final bite of my lunch before I exchange some more small talk with my co-worker. With my meal finish, I decide to check my phone, finding that I have a new email from my other employer. 

'Greetings Amelia

A client has requested our services and we've decided you'd be ideal for him. The client is an 18-year-old male who wants to lose his virginity. He wishes for you to come to 72 Ocean Avenue, where he resides, on this upcoming weekend.'

It might be odd, but I've always liked popping a cherry. Sure, these kinds of clients don't have any experience, but there's something special about molding a boy into a man, and letting him know what a potent, sexual being he is. Plus, by the time I'm done, he's going to be an expert when it comes to satisfying his partners.

* * *

On the weekend, I prepare for my next client. For now, I keep it basic with a nice purple summer dress, and a duffel bag filled with goodies. Once I'm dropped off at the two-story house, I ring the doorbell and wait to see exactly who I'm working with. When the door opens, I'm greeted by a lanky 18-year-old with short brown hair and thick-rimmed glasses wearing a Ricky and Morty shirt and a pair of track pants.

"Uhh, hey." He stammers.

I flash a smile, hoping to put him at ease. "Hey there."

"You're Amelia, right?"

"That's me." I smile.

"Uh, come on in."

I follow the boy inside to the living room. "So what's your name?"


"Pleasure to meet you James."

"You too." His voice still trembles with anxiety. Poor thing must be so nervous.

"You got the house to yourself this weekend?"

"Yeah, my parents are on a trip, so I've got the whole place to myself."

"Perfect. So could we sit down somewhere? I wanna talk for a bit before we get to it."

"Sure. My room good?"


James leads me to his room, which looks like the typical nerd den. Posters and figurines of various pop-culture characters litter the space, including the computer desk on the right. Next to the desk is a standing mirror as tall as me, and on the left is the bed, where the magic's gonna happen. We sit on James' bed, where he says "So, you wanted to talk?"

I put a hand on his thigh. "Well, communication is always a good thing before you get intimate with someone."


"So, what do you want?"

"Well, it's my first time doing it."

"Sex. Say sex."

"Right. First time having sex."

"You got any fantasies?"

"Well, uhh... I mean..."

"You can be honest with me James. I don't judge."

"Well, I haven't really done much. I mean I've kissed a girl, but that's about it."

"That's okay, but today, I don't want you to hold back, okay?"


"I've got a few outfits in my bag if you're into role play?"

"Uhh, I'm a bit vanilla."

"Vanilla's still tasty to me. You know I bought a set of lingerie just for today."

James perks up. "Really?"

"Yeah. Always love an excuse to add to my collection." I stand up and strut in front of James, who watches as I pull at the straps of my dress. It falls to my feet, flaunting the lacey-purple lingerie I'm wearing. His jaw drops, but I still ask the redundant question: "What do you think?"

"I uhh... I don't think words could do it justice."

"Mhmm, that's very kind of you. Now, come over here."

I lead James over to the mirror and make him face it. Leaning into his ear, I whisper "I want you to know that I don't do this job for money, I do it for fun. If I saw you in the club all dressed up, I'd think you're the cutest, most handsome guy around."


"Oh yeah." My hand squeezes on his crotch and... Oh my God, is that real? Maybe he's wearing one of those cock extension things. I have to fucking see for myself. With haste, my hands tug down and sure enough, I unleash an absolute behemoth of a cock.

"Oh my God... James. You're huge." I gasp. 

"It's not too much?" He asks.

"Not at all sweetie."

"I had a girlfriend, and she found my size to be uhh... intimidating."

"Some girls will James, but not me. In fact, I can't wait to show you how to use this massive cock of yours."

I wrap both hands around his girthy cock, which still isn't enough to cover his entire length.

"How long are you James?" I purr.

"12 inches."

"Geez, I think that's the biggest I've had." Normally I'm lying on the job when I say that, but not today. 

"It's not too much?"

"Oh don't you worry about me." My hands start stroking his humongous cock. "When's the last time you came?"

"Last week. I wanted to have a big load for you."

"Mhmm... You wanna give me a huge facial?"


My hands let go of his shaft. "Turn around for me."

I step back, giving James and his massive manhood room to turn. Once he's facing me, I get down to my knees and kiss his tip before dragging my tongue down his entire length. Next, I suck on his plump ballsack, letting his massive piece of manhood rest on my forehead. I'm already gushing at the thought of how built up he must be. That release of his is going to be huge, and I can't wait to get him there.

My tongue begins the journey back up his shaft. Once my tongue is just under his tip, I grip his shaft and begin swirling my tongue on that sensitive cluster of nerves.

"Oh yeah..." James coos.

"Mhmm... I'm just getting started."

I finally wrap my mouth around his tip. Let's see how much of this bad boy I can take. As I look James in the eyes, I slowly push down his length. When I get down to about a third of his length, James smiles at me, before moaning "Fuck yeah..."

I continue to take more of his cock in my mouth. To my surprise, I make it to my hand, which has to be past halfway on this monster. Drool is coating his cock and dripping out of my mouth, but I'm sure I can take more, so I move my hand and wrap my finger and thumb around his base. Then I continue down.

"Holy shit..." James coos.

That's when I hit my limit, with what has to be two-thirds of his cock buried down my throat. For a few seconds, I gag on his cock before retracting my mouth from his cock, leaving it drenched in my slobber.

"Fuck..." I gasp, looking at his spit-soaked shaft.

"Damn Amelia... How did you take that much?"

I look up to his surprised face as I remove my bra. "I'm a fucking pro, baby."

Then I wrap two hands on his drenched cock and stroke away.

"You reckon you're close?" I ask.

"Yeah... Sorry."

"Don't be sorry. I want that fucking big load."

That's when I put my lips around my tip, and swirl my tongue around it. My efforts soon reward me with a drip of pre-cum that lands on my eager tongue. Before he blows, I decide to retract my mouth.

"Mhmm you're oozing pre-cum, but I want more baby. I want it all. I want you to drain your fucking balls on my face."

"Ohh fuck..." He gasps.

"You getting close?"

James nods, so I open my mouth and stick my tongue out, ready to receive his seed. I know every stroke his bringing him closer to the brink. His breath grows heavier and heavier as his face tenses up. This is it. I've got him on the ropes. Any second now and he's going to erupt.

"FUCK." He growls, right as he explodes. Rope after rope flies onto my face, from my hairline to my eager tongue. Some even lands on my chest and dribbles down to my breasts. It's a pure miracle he missed my eyes. As I continue to pump his shaft, I say "Wow... what a huge load."

"Yeah..." James states, basking in his post-orgasm afterglow.

After I swallow what's on my tongue, I ask "How do I look?"

"Like you're covered in cum."

I chuckle for a second. "Do you like me being your cum covered slut?"


"Mhmm, how about you return the favor?"

"It's only fair I guess."

Sitting on the edge of James' bed, I then peel my panties off and say "How about you finger me?"


I then spread my legs. "Come here."

James moves in front of me and then gets down to his knees. There, he asks "What should I do now?"

"Rub my thighs."

Nodding, James proceeds to do exactly that. The nervous look on his face tells me he won't go further. Not without encouragement.

"Now lick the outside of my pussy. Don't enter just yet, okay?"

"Yes Amelia."

He drags his tongue along the lips of my entrance before looking to me for approval. I nod, so he continues, licking up and down my lips.

"Ohh that's it James."

He stops licking me to say "You sound so sexy Amelia."

Looking down at him, I reply "Mhmm. Just wait until you're fucking me... Now you see that little nub at the top of my pussy?"


"That's my clit. That's where the magic happens."


"Touch it gently."

James puts a thumb on my clit and begins rubbing slowly.

"Mhmm that's it."

"Can I finger you?" James asks.

Nodding, I say "Yeah, but do it slowly."

He then inserts two fingers from the same hand. Despite his excitement and inexperience, he follows my instructions perfectly, his fingers and thumb work slowly in unison to pleasure me.

"Ohh James... Finger me like you're trying to reach my belly button."

Somehow, James reaches my spot near instantly. Maybe it's beginner's luck or maybe it's just good instruction, but I don't fucking care. I'm not going to question how good he's making me feel right now.

"Ahh... now move your fingers like your motioning someone to come over."

Again, James follows my instructions just right, making me moan with ecstasy.

"That's it... That's good honey." I coo.

"You feel really wet." James replies.

"That's how fucking wet you've made me James... Keep doing that and make me cum."

As he continues to work his fingers and thumb, I grip the edge of his bed tightly. His smile grows as my face tenses up and my breathing becomes more rapid. Even an amateur like him would know he's got me on the ropes. Then again, he's done everything I've told him to do, so of course he has me losing my mind.

"Are you cumming?" He asks.

"Yes don't fucking stop James."

Caught in all the excitement, James starts fingering me faster. My legs begin to tremble whilst I feel the sensation near its conclusion. Suddenly, I hit my climax, which causes me to throw my head back as my body spasms. James' fingers leave me as I catch my breath and then look down at him with smile.

"Oh baby... You sure this is your first time?"


"That was so good."

"You weren't faking?"

"Oh no way. I mean I'd be pretty stupid to tell you what to do and have it not make me cum, right?"


"Mhmm, put your fingers in my mouth."

Standing up, James then puts his fingers on my lips. I suck on them, tasting my juices as I do so.

"Mhmm. Now, I guess you're ready for the main event, aren't you?"

"Yeah I sure am."

"There's some wet wipes and lube in my bag. Could you go grab them for me?"


Whilst James moves to my bag, I lay down on his bed and spread my legs.

"What about condoms?"

"You can if you want, but I'm on birth control."

"You sure?"

"Yeah. I want you to feel everything."


James comes over to me with both items in hand. He passes me my box of wet wipes and I quickly clean my face. As I do so, he takes initiative and pours lube onto that huge cock of his.

"Pour some on my pussy too babe."

"Sure thing."

He does exactly that, before moving on top of me and stroking his cock, spreading his lube around.

"Now remember. Nice and slow."

"Yeah. Okay."

"Ready to lose your virginity?"


"Anytime you're ready."

After a deep breath, James presses his tip against my entrance. As it sinks inside of me, I gasp whilst being reminded that he's not only long, but thick as well. That cock of his sinks deeper inside of my craving channel, stretching it out as he does so.

"Ohh baby... That's sooo good."

"Yeah?" James says.


"Ohh you feel so fucking good too."

That python between his legs continues to snake further inside of me. Looking at his shaft, I see that about half of it's inside of me, but it feels like so much more is there. He then starts to piston carefully. He's so cautious, and that just makes it so much better. I'd expect most virgins to just ram me like I'm a porno slut, but James is doing his best to make sure I'm comfortable.

"How am I doing?" He asks.

"Fucking great James. Just keep doing that."


"Yeah... You're such a good listener baby." I reach for my clit.

After a chuckle, James grasps my left breast.

"You can kiss me if you want."

Without hesitation, James bends down to kiss my lips. We exchange kiss after kiss as he continues to thrust. Fuck that dick of his huge. It's stretching me just right and combined with my finger rubbing my clit, I'm being driven crazy.

Between a kiss, I turn my head and say "Kiss my neck."

James does exactly that, allowing me to fill the room with moans. Praise for that gigantic cock of his to pleasure me, and for how he's using it. Then again, I wouldn't mind if he'd go a little faster now that I'm getting used to his size. Maybe a little bit more encouragement will get him there.

"You can go a bit faster now baby."

Ever the avid listener, James does exactly that. Not too fast, not to slow. Just right. The bed rocks as I put my other arm around him. His pace is working just perfectly for me, and it's making me moan. It's making my hands clench into his back and it's making my legs tremble. Most of all, it's making me cum.

"Ohh fuck... Just like that James. Make me cum agaaain..."

My climax hits right as the words leave my tongue. I'm shuddering underneath my lover, who pauses to catch his breath. When I come down from my orgasmic high, I look to James, who's panting and sweating like he's just hit the gym hard.

"You good?" I ask.

"I think I need a break." The sentence comes out as if it's just one long word.

"And I've got just the thing baby."

"Lay down for me."

Once James is on his back, I kiss him on the cheek.

"We're gonna need to work on your stamina."


"It's okay. Just something to keep in mind."


I start tracing my finger down his chest. "Plus, you did fuck me pretty good. Especially for a first-timer."


Biting my lip, I reply "I think you deserve a reward."

"What kind of reward?" He asks as my finger glides down his belly.


James eyes go wide. "Will it fit?"

"Mhmm, it'll be a challenge." My hand wraps around the base of that thick challenge. "But I like challenges."

"Well I won't say no."

"What kind of view do you want? Front or back."

"You know, I'd love to watch your ass bounce up and down my dick."

"Sure thing."

We lock lips as I grab the bottle of lube. I think I'm gonna use the whole bottle drenching this cock. As I pour lube onto his rod, I use my hand to spread it around. I then take that hand and use its fingers to tease my rear entrance, trying to prepare it as much as possible for the thick, long, hard challenge ahead. Whilst my finger enters my ass, I coo int James' ear "When I ride you, I'm not gonna stop until I drain those fucking balls off yours, okay?"


"When I ride you, I want you to talk dirty to me too. Tell me how it feels, or what your seeing, or call me names. Whatever comes to mind. Can you do that for me?"

"I can Amelia."

"Don't be afraid to touch me either."

There's no point wasting any more time. My ass is as ready as it's going to get. When I remove my finger, I sit upright and prepare to replace it with something much bigger. Now looming over his cock, I grip it with my right hand as I brace the other on his bed. This is it. Breathe girl. I lower myself down and feel his thick tip press against my entrance.

"Mhmm... You're gonna make me gape so wide baby."

"You like having your asshole stretched?" James asks.

"I sure do. How's the view?"

"Fucking perfect. Your ass is juicy as fuck Amelia."

"And it's all yours."

I start to lower myself down onto his tip. Despite my preparations, nothing could have prepared for how fucking THICK he is. I've had cocks up my ass before, but James' monster towers over the lot of them.

"Ohh James." I moan as his tip enters my ass. "You're fucking huge."

"You love it, don't you Amelia?"

"Ohh fuck... Absolutely."

I start to take more of his length inside of me. I don't think I'll walk straight for the rest of my life after this, but it'll be fucking worth it. It hurts a bit, but it hurts so fucking good.

"God that is fucking tight." James coos.

Looking over my shoulder to James, I ask "Does that ass feel good baby?"

"Oh... so fucking good."

"Better enjoy it whilst it lasts..." I squeeze on his ballsack as his cock sinks deeper. "'Cause I'm gonna drain your fucking balls."

He's about half way inside of me, so I start slowly bouncing up and down his shaft, taking a little more with every movement. I'm gonna take as much of this monster as I can. It has me moaning like a whore and swearing like a sailor, and I wouldn't have it any other way.

To my surprise, James then asks "Can I slap your ass?"

"Do it. Leave a mark."

I pause to make my plump rump an easy target for him, and in response, he slaps my right cheek.

"Harder." I growl.

BAM! He slaps the shame cheek.

"Ohhh harder! Leave a fucking mark."

SMACK! He slaps me once more.

"Ugh that's it. Who's ass is that?"

"Mine." James slaps me again, this time on the left cheek.


"I wanna fuck that ass doggy style now."

"Ohh absolutely."

"Go by the mirror and bend over."

With haste, I slide off of James' cock and somehow manage to walk to his mirror. There, I brace my hands on it and think about how empty I feel without his cock. It took so much work to get it inside of me, but now I feel so empty without it.

"Lube your cock up some more baby."

Soon enough, James' plants his shaft right between my asscheeks, before pouring lube onto it.

"Is that hole gaping for you?"

"Oh yeah."

"Give me that dick. Make me cum again."

Upon hearing my words, James presses his cock inside of me once more.

"That's it baby. Fuck my ass."

He starts inching inside of my tight hole once more as I look into the mirror. There I see myself, the ragged whore with cum drying in her hair and on her chest. I also see the man behind me, who's no longer a timid virgin. He's now the alpha male, fucking me with confidence. He's a goddamn stud who's gonna conquer the girls when he hits the college campus. James even remembers to put a finger on my clit, but I want more. I want him to fucking dominate me.

"Slap that clit."

Just like before, James heads my advice and begins slapping my sensitive nub.

"Oh fuck... yes yes yes yes!"

That's when he starts really giving it to me. I don't know where this newfound stamina has come, but I'm loving it. I swear that somehow I'm taking most of his length now, especially judging by how his balls are slapping against me. It's completely intoxicating, and it has me on the fucking brink.

"Fuck I'm cumming!" I scream, right as my body gives in, spasming throughout one more climax. I crumple into the mirror as James holds me up, giving me one last, hard thrust, before letting out a guttural roar that'll probably be heard throughout the neighborhood. His seed floods my ass as I turn to him. "Pump it some more. Get every last drop."

James manages a few more thrusts before slapping my ass one last time. He then stumbles back and sits on his bed, before laying down. After catching my breath, I join him, laying on top my worn-out lover.

"That good James?" I ask.

"Better than I'd imagined it Amelia."

"You and me both Stud."