Getting Pleasure

I've never not worn underwear before. Even if I ran out of clean undies, I would at least turn them inside out. It never crossed my mind not to wear them. And to go without a bra! Everyone would know and see my nipples through my shirt.

These thoughts racing through my mind excite me, but I don't understand why. I leave the house wearing a large sweater to hide my bouncing bosom from my parents.

"Isn't that a little unprofessional, Sally?" My dad, always judgemental.

"Mr. Smith said I can wear whatever is comfortable and this feels comfortable today, okay?" My smart-ass remark makes my dad set his newspaper on the counter. I follow up quickly with something about menses and he quickly gets back to reading.

My heart is racing the whole drive to the house. Before I get out of the car, I remove my sweater and leave it on the passenger seat. I can clearly see my puffy areolas and nipples through my white T-shirt, and I can feel moisture pooling in my sweat shorts. I couldn't bring myself to wear a skirt or dress my first time going commando. It just seemed like it would be too chilly.

I'm distracted while making our coffee and have to make a second pot before heading upstairs.

"You're late, Sally." Mr. Smith's tone is stern and concerned--his eyes immediately on my chest. "I had to pee without you today. But I can forgive you wearing a cute outfit like that. Come sit closer." He pats the bed covers next to him. Usually, I perch on the edge near his feet while we chat and sip our morning java.

I crawl my way to sit next to him and cross my ankles. I hand him his mug and cozy up to my own. There isn't much room for me, and he doesn't make any adjustments to let me have more space. Our legs are touching--mine above the covers and his underneath. Our bare arms squish together, and I can see my nipples making tiny tents over my chest. My face blushes as I sip my steaming mug.

His hand closest to me rests casually on my bare thigh while he sips his coffee with the other. "Are you wearing any underwear today?"

I shake my head and bite my lower lip. The comforter starts to tent around his crotch.

"Good girl." I smile and sip my coffee, feeling more relaxed.

As we drink, his hand on my thigh wriggles its way between my legs and I unhook my ankles. While he tells me about his dreams last night, his hand grazes my clothed labia as if he doesn't mean to. I wonder if he can feel how wet I'm getting.

He reaches over me to set his mug down, brushing my still hard nipples with his hairy arm and takes my mug as well. "I have a special surprise for you today, Sally."

"Oh, really!?" I'm excited to see what is in store today.

"Mm-hmm." Still hovering over me, he kisses my lips and explores my mouth with his tongue. I accept his advance since we've done this before. I did like making out with him. It was much more enjoyable than with my sister.

"I want you to relax." His hand grabs my breast over my T-shirt and squeezes hard while he continues to kiss me.

I yelp into his mouth and my body stiffens. He releases my breast and grips at my waist, moving his lips to my neck and bites lightly. I melt into his bed and can feel his hard penis against my leg through the sheets, tempting me to grab it.

He lifts my shirt up to my breasts trying to remove it. I lay there, unhelpful, not knowing where exactly this is going. He shifts out from under the covers and easily moves my small frame to the middle of the bed--my boobs jiggle at the jostle. His cock behind his boxers is at attention and weeping through the fabric.

Skillfully, he pulls my shirt over my head and my globes lay firm on my chest. His mouth attaches to my nipple and starts to suck and bite.

"Ow! Mr. Smith, um--" And he takes the other nipple and does the same. "Oh! I don't--" Goosebumps prickle across my whole body.

"Just enjoy this, Sally," he almost commands and kisses me again, quieting any objections I might have while he works at my shorts.

My hands fly to his to stop him. Is he trying to have sex with me? Are we really doing this? He tosses my hands away and swiftly yanks my shorts all the way off. I'm completely naked in front of him. I've never been exposed like this to anyone before.

My arms cover my warming chest subconsciously, so he grabs my wrists and pins them on to the pillow. His knees on either side of my hips keep my body where it is beneath him. His belly squishes against mine as he lowers his head for more kissing.

He grinds his rod against my exposed slit while his tongue slithers to the back of my mouth. Involuntarily I moan into the escalating events.

Releasing my hands, he scoots down and makes a trail of kisses from my neck, over my breasts, to my navel, and then--

"Mr. Smith! What exactly are you doing?" My hands are in his hair trying to push him away from my neatly trimmed pussy. He ignores my protests and licks my clit gently making me giggle.

"Hush now, or I'll have to gag you." I look at him with wide eyes. Gag me?

He continues to lick at my crotch, sucking my clit into his mouth and I can't help myself. I laugh again at the odd sensation and embarrassment of this old man licking me where tongues were not meant to be. With obvious frustration he removes his boxers, wads them up, and shoves them in my mouth.

The smell and taste of his cock invade my senses as his tongue again laps at my clit and pussy lips. He makes out with me down there just like he does with my mouth. His tongue dips between my lips for access and pushes past my hole stirring deep pleasure inside me.

My muffled squeals soak into his boxers. It's too much. I can't take it. This is when I would normally stop touching myself when I masturbate but he doesn't afford me such luxury. I try to push his head away to no avail.

His tongue juts in and out while his thumb presses hard on my clit and his other hand squeezes my tit mercilessly. When he twists my nipple, my body is flooded with both pain and pleasure and I'm so confused.

But there's no room to have a thought when an odd awareness creeps up from my groin and into my belly. I moan in increasing volume through the precum-soaked fabric. Something is building within me, and I have no control over my actions anymore.

Instead of pushing his head away I find myself grabbing his hair and pressing myself into his face. My body shakes as if I'm having a seizure as every corner of my body is flooded with pleasure, release, and desire.

Mid-scream he yanks the boxers from my mouth, and I'm surprised at how loud I sound. I've never made noise like this or felt so good in my life.

"Good girl," he says, watching me pant and convulse as my very first orgasm dissipates. I feel almost like I've had some of that wine again. Lightheaded and dreamy.

I'm sweating and grateful that it's over. He pushes me back down when I move to get up. Too weak to try lifting myself again I lay there and let him spread my legs apart with his knees. He rubs his wet cock on my even wetter clit sending shivers across my frame.

"Wait," I breathe, "Mr. Smith...are we...going all the way?" He just smiles and slips his mushroom head up and down my slit. "Please, I'm a virgin...I don't think I should do this."

Without pausing the rhythm of his cock, he says, "You know how this works, Sally. Do you want to say no?"

I'm torn. I feel so turned on that yes, I want to have sex. But I don't want him to be my first. I always thought my first time would be with someone I loved like all those romantic comedies.

Before I can give an answer, his tip is inside me. It's invigorating and my body wants more but my hands try to push him out and my legs feebly attempt to close. He shoves my knees apart with his belly as he lowers his much larger body on top of me, shoving his cock inside another inch.

My mom never covered sex during homeschooling. In fact, I don't even think she knows that I know anything about sex. Not that I know much--or knew much before working for Mr. Smith. Vaguely recalling the sex-ed I'd seen on TV shows, I whisper in a desperate breath, "Sh-shouldn't we use a condom though?"

He ignores me. It feels impossible to accommodate his girth and I try to wriggle away but his weight is too great. His face shows annoyance at my motions. Still inside me, he reaches for his nightstand drawer where I hope he's grabbing a condom from. Instead, he pulls out the fuzzy handcuffs I'd seen before.

"If you're not going to sit still then we'll need these." He quickly attaches the cuffs to one wrist and snakes the other half through the bars of the bed frame above my head and clicks it around my other wrist.

My heart quickens and he slowly presses on with his penis. I can feel my heart and his hardness in my pussy. I clench and he moans fitting more of his massive cock inside me.

"You are such a tight little thing. My wife was a virgin when I had her first too. But she wasn't as tight as you!" Slowly, steadily he slides deeper and deeper into my little cave.

I feel almost prideful when his balls rest on my ass. My small hole fit him completely. I didn't think it was possible. The feeling of fullness is incredible. He must be 8 inches or so. I didn't think it was supposed to go all the way in like this. And it didn't hurt like my friends told me it did for them. It feels more like pressure and pleasure as my walls accommodate his size.

After resting for a bit, he starts to pull his cock out and I hope this is it. That he just wanted to dip inside and take my virginity and go. Such wishful thinking.

He pumps in and out with his full length, making me gasp each time his head breaches my entrance. It's bulbous and thicker than his shaft. He picks up the pace and grunts each time he bottoms out.

I pant in unison with his grunts and can tell he is restraining himself from climaxing. An alert springs up inside me and I blurt out, "Wait, what if I get pregnant? Please don't cum inside me, Mr. Smith!" His wicked smile creeps across his face. He fucks me harder and faster, ignoring my plea.

Again, I feel the new and amazing sensation take over my body. I feel myself fucking him back against my better judgement. I cum over his cock and he groans loudly as he releases his sperm inside my no-longer-untouched pussy. Pinching my clit between his thumb and finger, I cum again milking ever drop from his old balls.

When he's finished, he collapses and rests his head on my heaving breasts. My body continues to suckle the juices from his cock as my insides spasm.

Tears fall from my eyes, down my cheeks thinking of possibly getting pregnant at 18. My parents would never forgive me. I don't want him to think I'm upset with him so I quickly wipe the tears away with me arms as best I can.

His cock is relentless, still stiff inside me while he kisses me deeply. He starts to pump again, and I accept defeat. It's already done.

I can feel our fluids pooling under me on the sheets when he finally pulls out. He holds his cock with one hand and grips my breast with the other as he lowers his angle. I feel pressure on my anus like when he touched me that first day. He rubs his cock up and down my slit again but this time he slips from my clit down to my asshole. Over and over until every bit is slick with both of our cum.

Hoping he is just teasing I let him dip inside my pussy again. But then he rests at my asshole, and I feel more pressure building until it's too much and I realize what he wants.

"No, no, no, no. Mr. Smith, not that, please!" With my hands still in the cuffs I only have my words to defend me.

He stops immediately but doesn't remove his cock from where it sits just outside my tiniest hole. "Are you sure you want to say no to me right now?"

My tears look in his eyes pleadingly. "I...I don't know."

"Let's find out then," and he plunges forward breaking the seal of my sphincter with abandon. I feel like my ass is on fire and scream at the pain.

"Aaahh, Mr. Smith it hurts!" His boxers are back in my mouth, and he treks on, clearly unable to contain himself like he did with my pussy.

"If you relax it will feel much better."

My cheeks are hot and wet, and I don't do anything to hide them this time. He watches my face intently, biting his lower lip as he stretches my anal canal to an unnatural size. I scream into the boxers and inhale his scent. For some reason the smell of him helps me relax a bit which allows him to delve further into my forbidden depths.

"Good girl," he growls, and I am liquid. His cock easily glides all the way in.

My screams turn to moans as he pumps in and out. It takes all my concentration to keep my ass loose so that it doesn't hurt each time he drags his cock out. I try not to focus on the sensation that warns me that I might shit his bed which he makes much easier when he puts his thumb on my clit.

I can feel my inner walls contract and release--squeezing his cock inside me every time he presses my button. This doesn't last long as he soon forgets all about me and fucks me harder.

It's painful without stimulation to my clit and I'm screaming into the gag again. I think he likes this because he lifts himself up and hangs my legs on his shoulders. At this angle, with my ass off the bed, he fucks me even faster and deeper which I didn't think was possible. The pain finally subsides, and I just want him to finish. He jabs at my clit again and I feel another orgasm build.

He removes the gag in time for me to plead, "Please, Mr. Smith, please cum in my ass. I want you to."

He loves it. I can tell because he slams into me and stays put while rope after rope decorates my bowels and I climax right along with him. He doesn't remove himself right away like I hoped but keeps himself inside until he deflates enough to slip out of me unintentionally.

The sheets are wet and sticky with sweat and spunk. He takes the handcuffs off, and I curl into the fetal position, hiding my face in the pillow. He curls up behind me as the big spoon and whispers, "Good girl. Such a good girl." I shudder at the praise and nuzzle my ass into his groin.

I must have fallen asleep because I'm alone in his bed when he sets a cup of water on the nightstand. I weakly sit up and gulp down the offer.

"We'll take it easy today," he promises. "Let's take a bath and then you can wash the sheets before heading home early."

Feeling dazed I follow him to the bathroom, naked and dripping. The bath is still filling up producing hills of bubbles.

"That running water's got my water running. Help me pee first." He stands before the white porcelain and waits.

I kneel before him on the folded towel as previously trained and reach for his flaccid cock.

"This time, I want you to try and aim with your mouth. Here," he puts his hand on my head and places his cock sideways in my mouth--the tip poking out on one side, and his pubic hair tickling my cheek on the other.

I can taste that he hasn't showered since my double deflowering. He tastes bitter and pungent--a little sour.

This was going to be impossible to aim! I side eye the toilet bowl and do my best to aim for the water. His hot stream of piss flows without warning and ripples down the head around my lips and onto my lap.

I try lifting his penis to arch the flow, but it just makes it worse and drips down my face more. I angle downward but it lands on the seat and the floor.

When he finishes, he easily slips his cock right into my mouth for cleaning. I imagine he doesn't have anything left to cum again, but I'm wrong. He gets hard quickly and fucks my face harder than usual.

I barely have the strength to lift my hands to his thighs to try and stop the assault. He grips my hair into a tight ponytail and shoves my face into his pelvis. I gag and try to breathe through my nose while he holds me there unloading inside me again, straight down my throat and into my belly.

My belly. I remember that he came inside me without a condom and the fear of pregnancy creeps in again. Tears fall down my face as I try to swallow his cock and cum.

"Good girl. You truly are a treasure." He lifts me from the floor and carries me to the bath, cutting off the water.

I hadn't noticed how large his tub was before now. We easily fit together as he lays me on top of him. Our heads resting next to each other, he kisses my cheek sweetly.

The steaming water feels like heaven on my wrecked orifices. He spreads the suds over my heavy breasts leaving bubble trails over my spent nipples. The soapiness of the water makes it easy for him to glide his hands over my tummy and down to my pubis.

I want to protest but I just don't care anymore. My mind is tired and puzzled about how I feel. Leaning into the pleasures I'm receiving I allow him to do whatever he wishes. Fingers circle my clit and I gasp meekly. My face turns to meet his and our lips lock together.

His cock remains flaccid and I'm grateful, so I bring more enthusiasm to our make out session. Softly this time, he massages my breasts, and it feels wonderful. I welcome his gentle exploration of my genitals as he cleans out my jizz-filled cunt and anus.

It's uncomfortable at first when he slips his digit in my dunghole but I don't fight him. I appreciate the sensual care and slip my tongue deeper into his mouth. With his finger in my ass and his thumb circling my clit I feel another orgasm rising within me.

I beg against his lips, "Please make me cum, Mr. Smith."

He obliges and works my clit and asshole gently, edging me at first, until he finally allows me enter bliss for the fifth time in my life.

"That's my good girl. And you can call me Sir from now on."

"Thank you, Sir."