My First

Story Info
She loses her virginity to her former boss.
1.6k words
3.98
37.6k
5

Part 1 of the 3 part series

Updated 09/22/2022
Created 12/11/2012
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

His lips trail a fiery path down my body. They start at my breasts and end at my core. His mustache tickles my thigh as he moves lower. I'm clutching the sheets so tight in anticipation. Nobody has even done this to me before, and I'm eager to feel the sensations I've only dreamed of.

He teases me by placing small kisses on the top of my thighs, but makes no move to do what I really want. I wiggle my hips and lift them up. When I lower them back down, I see the arrogant smirk on his face. I would be mad, but there's no point. He probably needs some validation that I really want to do this.

His hands slowly caress my body, making me want him even more. He's trying to be gentle, and I love it. I also hate it because I want him so badly. He promised me so much pleasure, and I want him to deliver it.

His right hand reaches the triangle in between my legs. It touches the landing strip of hair I have before running down the seam of my lips. A moan escapes my lips.

He takes this as an invitation to use his tongue. Warm, wet flesh grazes my clit, and I practically come apart. He does it again, and I reward him with a groan. His finger touches me there, pulling me open so he can have better access.

Gone is the gentleman from earlier, and here is a man whom I've only seen glimpse of. Licking, sucking, nibbling at my core, he attacks me with ferocity.

I'm twisting and turning on the bed. The room feels too hot, and I'm ready to explode. My hips are thrashing about as I receive the most intense pleasure I have ever felt. I feel hand press down on my hips, and I realize he is trying to keep me still.

I try to limit my movements, but then I feel a single thick finger slide into me. It's a slight discomfort at first, but with him licking my clit, pleasure takes over rather fast.

I can feel the sensations building in me as he continues to use his mouth and finger to pleasure me. My mind is empty of all thoughts except achieving that orgasm. I want it so badly, and he knows it. He slips in a second finger, making me wince a bit. I quickly adjust to the feeling, and I'm headed towards the finish line once again.

Right as I'm about to achieve that glorious moment, he stops. He lifts his head and removes his fingers. I have never felt so empty and void in my life.

He moves up my body and plants his hands on either side of my face. I close my eyes to avoid his gaze.

"Look at me," he commands. His voice leaves no room for argument, so I open my gray eyes to stare directly into his brown ones. There's softness in his eyes and some unrecognizable emotion. I know my eyes are glazed with lust, and that's all I want him to see.

"Are you sure you want this?" he asks. I nod eagerly and arch up against him to prove my point. He seems unresponsive to my gesture. His eyes continue to stare into mine. He's serious.

"It will hurt, and once I start, I might not be able to stop," he warns. I lean up to kiss him hungrily, and finally he responds.

I pull back to answer him. "I really want this. I know it's going to be painful, but I want it."

He seems to be content with that answer and covers my lips with his. His mustache and beard scratch my skin, but I don't care. His lips are firm and skilled. His tongue strokes mine and caresses it. I want him so badly. And from the thing prodding my thigh, I can tell he wants me too.

He settles his hips over mine, and I feel his erection nudging at my entrance. I take a deep breath and tense up as I feel pressure. He stops as soon as he feels my reaction.

He breaks our kiss and says, "It will hurt less if you relax." He moves his hand to my back and starts stroking it in small circles. It's comforting, and I try not to think about the upcoming pain.

I feel the head of his member push into me, and I force myself to remain calm. He's stretching me so wide. I didn't consider him to be that big, but it feels like that thought is wrong.

As he pushes farther into me, it really starts to hurt. I dig my nails into his skin to make him the feel the pain I was experiencing. One final push, and he's all the way in.

It hurts so much, I can barely breathe. It feels like he's tearing me apart. Tears come out of eyes and fall down my face. He kisses them away, and I feel slightly touched at the gesture.

"I'm sorry," he whispers in my ear. "I'll make it better." He pulls out a little and reaches his hand in between our bodies.

His fingers find my clit, and his lips find my breast. I'm still stinging from his entry, but this attention feels good. He circles my clit with his finger which makes me hips involuntarily jerk. It makes him slide all the back in, and I bite my lip from the pain.

"Ow," I mutter. His lips suck my nipple and his tongue generates an amazing sensation. I slowly rock against him even though it hurts. I want the pain to end. I want to be able to enjoy my first time.

"The pain will go away soon enough. Until then, just feel." He pulls out of me completely, and then slowly sinks back in. This time it feels different. The friction feels delicious.

"Again," I murmur. He pulls out and thrusts back in. I moan at the feeling.

"I've been waiting for this for years. I've been fantasizing about fucking you since you started working for me," he whispers as moves his member into me faster.

I'm meeting him thrust for thrust, and soon we find ourselves in a rhythm. He keeps his hand on my clit, pinching it hard. It helps get rid of the rest of the pain, and soon I find myself crashing over the edge.

He doesn't stop even as I come back to consciousness. He's still moving inside of me. I feel another orgasm building, and I don't even fight it.

A few more minutes of panting and thrusting, and we're both careening over the edge. I feel his cum filling me up. I'm on the pill, and we're both clean. Plus, he wanted me to feel the real thing my first time. I love it. Hopefully, we can do this more often.

He stays inside me for a few minutes, regaining his composure. I'm almost ready to go again, but as he pulls out of me, I can feel myself growing sore.

He sees me wince and kisses me on the cheek. "You'll be sore for about a week. You should try soaking in a bathtub. I hear it helps."

I attempt to laugh, but I'm too exhausted. Instead I turn away from him and let myself rest. I don't know if he's going to kick me out now that we did the deed.

I feel a hand caress my back. He's probably tracing the tattoos on my back.

"What are you thinking about?" he asks. I'm tempted to ignore him.

"I'm sore and achy. I'm pretty sure if I try to walk, I'll be in a world of pain."

"I can help with that," he says and leaves the bed. I hear him grabbing stuff in the bathroom, and then I hear the water running.

Shortly, he returns to the bed. He rolls me onto my back and opens my legs.

I sit up and look at him. "What are you doing?" I ask. He has a small bowl filled with water and a washcloth.

"Taking some of the sting away. Just lay back and relax, it won't take long."

I sit back and watch him. He dips the washcloth in the water and presses the cloth to my entrance.

The warm water against my vagina feels so good, so I moan. I swear his ears perk up, but he continues to apply the water to my area. He does his best to clean me as well. Then he grabs a bottle and squeezes some substance onto his fingers.

He slides a finger inside me and applies the lotion-like substance to my walls. It has a cooling effect that makes me groan in relief. I start to get turned on again and move my hips against his finger.

"Stop," he says. "I'm trying to take away the pain. If you keep moving, I'll end up fucking you again. And you need to rest."

As much it pains me to do so, I stop. Once he removes his finger, I feel better.

"Thank you," I say weakly. He presses his lips to my forehead.

"Spend the night. Rest up. You can leave tomorrow, if you want."

"If I want?" I ask with a smile. He shrugs.

"I could use the company."

"I'll still be sore tomorrow," I add. He shrugs again.

"I know that. We don't have to have sex. Just hang out," he suggests.

"Sure," I say and turn back onto my side. Exhaustion overwhelms me, and I slip into a deep sleep.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
AnonymousAnonymousover 8 years ago
First time

writers of this site need to understand what the hymen is. if you look at a vagina and pull the labia majora or labia minora open you will see a round opening. If the woman or girl is a virgin it is still a round opening, except the skin around the opening that is her hymen is just a short distance inside her vulva. Look at a picture on the computer and I'm certain you will find what it looks like, or talk you cousin, girlfriend or a person you know is a virgin to allow you to inspect her little puddy-cat. The hymen is not some blockage membrane that stretches completely across the woman's sex, and it can be totally blocked or slightly blocked if the hymen is imperforate microperforate hymen. The hymen has openings so a female's periods can pass from her body. Some hymens might have more than one opening. So before you write about busing some female's virginity or cherry, discover what such item truly amounts, too. Guess most of you have never looked up any female's tiny little opening of pleasure.

OleguyOleguyabout 11 years ago
Slightly lost.

I usually don't comment on the factual side of submissions to the system.

But from my very limited experience I never heard of a weeks discomfort after a defloration.

Also as far as I can find out, and this was backed up by my only experience, the hymen is right at the entrance of the vagina, not part way in.

Prolonged_Debut10Prolonged_Debut10about 11 years ago
Convincing

This is the best descriptive story about a first time experiece for a young woman I have read. The parts that are meant to join this story together are suspect, however her narration is riveting.

johnr9911johnr9911over 11 years ago

So exciting you sharing about your 'first time'

Great descriptions

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Amber and Jack Ch. 01 Jack offers the babysitter a ride home. What ensues?in First Time
Oh Baby, Baby Mister Conaway gives the baby sitter her first time.in First Time
Duty Ch. 01 The Kingdom needs an heir...and the King moves to action.in Romance
Cucked by my Father Ch. 01 My gf moves in and becomes involved with my father.in Fetish
My Grandfather fucks my Girlfriend All weekend long she was his.in Mature
More Stories