My Night With Lara Flynn Boyle

“Rub it in deep. Plenty of it.”

She watched my hands at work at my dick. “Be sure to put a lot along the back edge of the head. And the shaft as well.”

“It works fast. I can feel it tingling. It’s making my fingertips numb, too.”

“The towel’s on the floor.”

I scrubbed my fingertips on the towel, but it was too late. Most of the sensation was already gone. “How long does this stuff last?” I dropped the towel on the floor once more.

She barked her sexy laugh again. “Long enough. Come here.”

I walked on my knees until I was in between Lara’s legs. She flicked a polished fingernail hard against the head of my cock. “Feel that?”

“Just barely.”

“Good. Look at that beautiful thing,” she said staring at my cock and fingering herself again. “Standing up, throbbing like that. It’s like a weapon. It’s going to stretch open my little hole, slide up through my narrow canal, filling me till it almost hurts, pushing deep inside me until I can feel it in the pit of my belly. I don’t know why I dried my pussy. I’m just getting wet all over again.” She lay down once more and pulled her knees up and back towards her shoulders. Soft squishing noises came from Lara’s pussy as she finger-fucked herself harder.

Then she crooked her finger at me, gesturing, “Come here.”

I leaned forward, put my hands beside Lara’s shoulders, and looked straight down at her. Her arm went between our bodies. “Feel that?” she asked.

I shook my head, and she smiled up at me. I looked down between us and saw Lara digging all five fingernails into the head of my cock.

“I’ll guide it in for you.” I watched as she gripped the shaft; I couldn’t feel that either. But I did feel her pulling me down on top of her until my hips were close enough to hers to feel her body heat.

“Okay,” Lara said, “the head is between my lips. Now don’t move.” She slid both hands around my hips and onto my ass, giving both cheeks a strong squeeze. “Don’t push. Let me pull you into me. I love the feeling of a cock sliding in and filling me up.”

Lara closed her eyes as she pulled my hips closer to hers, and once more I saw the famous face that I had been seeing on television for years. I concentrated on my cock, waiting to feel the heat, the tightness, and the slipperiness that I hadn’t felt in five years.

But I felt nothing.

Lara smiled, her eyes still closed, and she moaned soft and quiet. “Oh, wallflower, good…thick…cock.”

Lara kept pulling me by my ass and I kept sinking deeper into her. But I felt nothing until my balls came to rest under Lara’s pussy and my hips rested on top of hers.

I started to withdraw, wondering how I would know when to push forward again when Lara dug her fingernails into my ass.

“Not yet! I want to enjoy this for a little while.” We lay there motionless for several seconds, and the heat from Lara’s body warmed me. Her body was much warmer than mine. “Don’t lean on your elbows.” She used her upper arms to push my elbows from under me. “Put all your weight on top of me.”

I lowered myself completely on top of her as gently as I could; I was suddenly worried that her willowy body might to be too frail to support my weight. Her small breasts flattened under my chest, and she let out a long satisfied, “Ahhh.” I buried my face in the right side of her neck, smelling shampoo, perfume and a trace of cigarette smoke. Lara put one hand on the back of my head, and the gesture somehow made me feel safe and protected and wanted. Her lips brushed my ear as she said, “You have a wonderful cock, wallflower.” Her warm breath raised goose bumps down the side of my neck.

She buried her nose in my neck and inhaled deep and loud. “Good smell: clean, manly.”

She moved under me and I felt the insides of her thighs slide up onto my sides and the insides of her ankles pressed into my hips. She pulled my face harder into her neck and whispered, “Fuck me. Fuck me good.”

I pulled my hips back what I guessed was a couple inches and pushed forward again and Lara sighed. “Yes. Short, slow strokes.”

It took only a few seconds for me to get an idea how far I could withdraw and stay inside her. I lengthened my strokes and Lara sighed in approval.

But before Lara could get used to the longer strokes I began mixing them up, varying longer ones with shorter ones. And I kept changing speeds.

Lara grabbed a handful of my hair and pulled my head back. Her eyes were open now and she was beginning to breathe through her mouth again. “That’s good! Keep doing that!”

Still holding a handful of my hair, she pulled my face down to hers and kissed me hard and rough, her tongue forcing its way into my mouth. I licked her tongue and fought the urge to cringe from the taste of cigarettes. Instead, I sucked her tongue, bad taste and all.

Every time I thrust my hips forward, Lara huffed her hot breath into my mouth as we kissed. My cock was completely numb; all I felt was my balls slapping Lara between her pussy and asshole. I wondered if I might come anyway. Just because I couldn’t feel the friction Lara and I were creating, it was still there, doing what evolution intended it to do.

Lara caressed my face with her other hand, and I felt her nipples stiffen nipples against my chest. Her ankles slid up and off my hips and she dug her heels into my ass, trying to pull me deeper inside her.

I broke the kiss and put my face back into Lara’s neck, inhaling deeply, smelling things I’ve always associated with women: perfume, clean sheets, the flowery cachet from Lara’s bed linen. She kept a firm grip on the back of my head, holding my face safely against her neck. The air in that space between her neck and her pillow was warm and close and feminine.

I switched from long, slow strokes to short, fast ones and Lara moaned and giggled into my ear in response, sending another wave of goose bumps rippling down the right side of my body.

She let go of my hair and slid her arms around me so that both her forearms were pressed against the back of my neck pulling me down – hard. She had strong arms for such a slender woman. And as hard as she was pulling down on me, she continued to pull still harder.

Her breath came harder and faster, and with her mouth against my ear, I couldn’t hear the rustling of the mattress under us. And she hugged the back of my neck still harder, causing me real discomfort. I needed to get her to stop pulling me so hard without breaking the mood.

I stopped thrusting, pulled completely out of her, and got up on my knees. Before she could say anything, I gripped her behind her calves and slid her down the bed, closer to the footboard. I quickly put all my weight on top of her again her and slid forward into her pussy. When my balls slapped above her asshole, I put my feet against the footboard and continued to push, driving as deep into her as I could.

Lara squeezed her eyes shut and cried out. I couldn’t tell if it was a cry of pleasure or pain.

“Oh, baby, yes! Do that! Do that!”

“It doesn’t hurt, does it?”

Her eyes snapped open and they bore into me. “It hurts so good,” she said, gasping loud. She grabbed my ass, digging her fingernails into me and pulling me hard into her. “Make it hurt. Make it hurt good, baby.”

I had gone from “wallflower” to “baby” with one move. And I wasn’t even thrusting; I was holding one steady push trying to get as deep inside her as I could go. And she was trying to help me get in deeper by pulling at my ass.

“Hurt my little pussy, baby,” she said, her womanly, smoky breath hitting me in the face. ”Drive that thick club in deep. Make my tender pussy ache.”

“I don’t want to hurt you.”

She slapped me on the ass hard. It sounded like a small gunshot

“God damn it! Do it! I want it!”

I kissed her – or tried to – but Lara caught my lower lip between her teeth and sucked on it hard enough to cause real pain. I pictured myself leaving the house with a huge hickey on my lip. She pulled harder on my ass. I tried to push deeper into her but when I saw her flinch, I pulled back.

“No! Don’t keep pulling back like that!” she ordered, still holding my bottom lip between her teeth. “I told you: I like it!” I slowly pushed back in as deep as I could, then I tried to go a little farther and Lara again cringed with the ache. “Yes. Like that. Fuck me deep.” She sucked even harder at my bottom lip – so hard I started to worry my lip would split open.

I wasn’t sure about any of this but I did as she asked and slid my cock into her again, staying deep inside her, pulling back just barely, only an inch or two before thrusting in again.

Every time I pushed into Lara she winced. She let go of my lip, rolled her head back on the pillow. Her face relaxed slightly when I withdrew and then she cringed when I slid forward.

Her heels slid off my ass and she dug her feet in between the front of my thighs and the mattress. When I thrust into her, she used her feet to pull up against my thighs. It took several strokes before I realized what he was doing: each time I pushed into her, she pulled up with her feet to rock her hips downward so her clit would be in direct contact with the shaft of my cock as I pushed into her pussy.

As each of my strokes slammed into her, she cringed. And each time she cringed, I flinched inside. But she was getting that urgent look in her eyes between the cringes. Huff after huff of warm breath smelling of alcohol and cigarette smoke hit me and combined with the smell of perfume, floral sachet and clean sheets. She didn’t blink; she just stared and cringed up at me, gasping, humping her hips downward with each inward stroke of my cock.

“Harder.” Her voice just a raspy pleading hitching a ride on her loud exhales. “Baby, make it hurt just a little bit more.”

I tried to push deeper with each thrust. And as my pubic bone hammered Lara’s, she began to whimper out loud. Our rhythm was perfect and the sound of our bodies clapping together filled the room. I thought if anyone were in the house, they would instantly recognize the sound.

As if on cue, a car roared by outside, but the sound couldn’t drown out the slapping of our groins or Lara’s whimpers.

I began to feel more confident. Lara was genuinely enjoying the discomfort. I could have looked at her forever like that: her dark-brown ponytail laying across the white pillowcase, her blue eyes staring urgently up at me, her neck, chest, and shoulders, flushed pink, a thin film of sweat shining on her forehead.

I began to wonder again how long the desensitizing cream would work when Lara gritted her teeth and her whimpers changed to what sounded like hisses.

“Faster, do it faster,” she grunted between her hisses.

I did as I was told, and immediately Lara began nodding her head. I listened to her hisses and realized she was grunting, “Yes” with every in-stroke. Lara tried humping her hips downward to match my strokes but she couldn’t find the right timing any more and our rhythm became ragged. But Lara was too far along to care. She kept up as best she could: hissing and humping and pulling at me.

And then her eyes opened wide for a moment before squeezing shut. She stopped hissing “yes” at me and gritted her teeth and growled. She arched her back so far I was able to slide my arms around her body, and again I was struck by what a tiny thing she was, and I held her tightly to me. She bent her head so far back that the tendons at the front and the sides of her neck popped up and strained under her skin. The tops of her feet pushed up against the tops off my thighs so hard that my feet slid up the footboard, and I had to grab the top edge of the footboard with my toes so I would be able to keep thrusting into her.

She held her neck and upper back in that arched position as a muffled growl from deep in her throat filled the room. Her fingernails dug into my ass so hard I felt a burning sensation and, for a moment, I wondered if she would break my skin.

After ten seconds later, she collapsed back onto the bed her arms and legs going lifeless.

I stopped thrusting and gently lowered myself on top of her, feeling proud of myself.

Our breathing slowed and our bellies kept sticking to each other by a thin sheen of sweat on our bodies. I felt Lara’s heart thudding against my chest.

We lay there like that until our breathing had returned to normal and she took my face in both her hands to look at me. Her eyes darted around as she looked at every part of my face.

“Wallflower, you are a prize.”

She pulled my face down to hers and kissed me, long and soft and loving.

She broke the kiss and asked, “Is the cream still working?”

I nodded.

“Good. One more time.”

“Again? You said your clit gets too sensitive…”

She shook her head. “That’s after someone goes down on me. I can come two, sometimes three times in a row from fucking. Hurry!” She slapped my ass. “Don’t let my pussy cool down.”

“What am I? A cock for hire?” I joked.

“’For hire’?” she asked, lifting an eyebrow. “’For hire’ means you get paid. You’re just a stud for the night,” she said coldly. She stared at me for five full seconds with a stern expression on her face. And then she winked. “Nothing more,” she added with an unmistakable tone of affection in her voice. She kissed me tenderly – and held the kiss longer than I expected her to. When she broke the kiss, she pulled my face to hers so our foreheads and noses were touching and she looked me in the eyes and whispered, “Please make me come again, baby.”

I lifted my feet against the footboard and slid deeply into her.

“No, no,” she said. “Gentle this time.”

Once more, Lara hooked her feet under my thighs and we fell into a tender rhythm.

Hidden away from the rest of the world, the two of us quietly rocked and rolled our hips in a slow, steady rhythm, kissing and smiling and breathing in each other’s breath.

Our tongues danced and sparred. I gently sucked her top lip (and caught a slight taste of beer) while she sucked my bottom lip – tenderly this time.

Lara dragged her fingers up and down my spine, sending wave after wave of goose bumps running across my back.

As I looked at her, the first impression Lara made at the Ball came rushing back to me: defiant in sparkling bright red in a sea of plain black and white, the only one who dared to smoke in the ballroom: she was confident and beautiful and womanly. And now she was lying under me, staring up at me, kissing me, her arms around me, and her thighs gripping my hips.

And then I felt just a hint of the heat and pressure of Lara’s pussy around my cock.

“The cream is starting to wear off.”

“You can feel me?” she asked, still kissing me, her words going into my mouth.

“A little.”

She smiled a contented, loving smile. “Okay.” She pulled me down off my elbows and hugged me tight. Once more her lips brushed against my ear. “Fuck me, wallflower. Fuck me slow and deep and gentle.” She rocked her hips a little faster and harder.

I slid my arms between her and the mattress once again and held her tightly as our hips fell into perfect timing. We stared into each other’s eyes as our kisses became more urgent.

Each time I thrust into her, Lara raised her hips to meet me and grunted softly. Suddenly, she tightened her arms around me.

I looked at her, my eyebrows raised, silently asking, “Is it starting to get close?”

She flashed her perfect white smile and nodded. And a wave of genuine affection for this passionate, beautiful sexual woman flooded through me.

Each long slow stroke up into her belly made her grunt a soft puff of air creating a warm spot on my cheek.

Lara clamped her thighs around me tighter and tighter as she raised her hips harder and faster to meet my thrusts. Her exhales landed on my cheek with more force. She pulled my face to hers, caught the tip of my tongue between her teeth and gently sucked my tongue deep into her mouth.

I stopped thrusting – my cock as deep inside her pussy while she held my tongue deep inside her mouth, massaging it with her own. I pulled my cock almost completely out of her, and she pushed my tongue almost completely out of her mouth. When I slid into her, she sucked my tongue into her mouth. She did that again and again: when my dick slid into her, she pulled my tongue into her. When I slid my dick out of her, she pushed my tongue out of her.

The tingling in my groin grew. The warmth and pressure of Lara’s pussy were becoming more and more noticeable. So much so that I had to break the kiss.

Lara recognized the look of concern on my face. This time she raised her eyebrows, looking to know if I was getting close to coming.

I nodded and Lara bucked her hips harder than she had all night. Lara’s stiff clit pressed along the top of the shaft – I could feel it now, and I re-positioned myself, riding higher on top of Lara so she could make stronger contact between her clit and my cock.

Immediately, Lara closed her eyes, bucked her hips against me more fiercely, and let out a satisfied, “Perfect, wallflower.”

Then she opened her eyes again, and still smiling and staring at me, began nodding her head, encouraging me onward. Lara’s gasps drowned out the sighing of the mattress.

Lara pulled my head down to hers until our foreheads touched. Once again that urgent look appeared in her eyes.

She opened her mouth wide, breathing hard.

I reached under her ass and pulled her up to me each time I plunged into her. Still holding my forehead to hers, she nodded in approval, her eyes wide and unblinking. Sensation was quickly returning to my cock; each time I pushed into her I felt the walls of her pussy grabbing at me trying to stop my cock from sliding back out.

Her gasps morphed into soft sobs as we worked together to bring her to orgasm.

I squeezed her ass and pulled her pussy and clit against my cock with every in-stroke. Our foreheads and our eyes seemed to be locked together. Lara’s sobs got louder and tears welled up in her eyes.

Her pussy tried harder than ever to hold onto my cock—my sensitivity almost completely back now. We were now in a race to see which of us would come first. I wanted it to be Lara, but I wasn’t sure that would happen—the sensations were rushing back to my groin like a tidal wave. I wondered how intense my orgasm would be. I had had this hard-on for more than an hour and a half; I hadn’t been with a woman in five years, and Lara’s beauty and sexual aggressiveness were the stuff of my fantasies. I wondered if it was possible to come so hard that I do some sort of damage to my balls. That thought pulled me back from the brink of orgasm; the building pressure deep inside my lower abdomen faded. But it wouldn’t be gone for long.

Just then Lara’s opened her mouth wide, she inhaled suddenly and sharply, and drove her head back onto the pillow. She locked onto me with those blue eyes and gritted her teeth as her entire body went rigid under me. A loud groan tried to escape from her throat but she caught it and fought to keep inside. Her hips bucked up against me so hard we were both bouncing on the mattress. A single tear slid from her left eye rolled down the side her face towards her ear.

The sight of her like that: her blue eyes opened wide staring at me, her body rigid, the muffled moan, and that lone tear pushed me to the brink of my own orgasm. Now that Lara had gone over the edge, I desperately wanted to follow her. Instead of trying to ignore the twinge deep inside me, I focused on it, mentally encouraging it.

Lara went limp under me, her thighs fell away from my hips, her arms dropped to the bed, and the groan she fought to stifle escaped as a contented sigh. She stared up at me with a tranquil smile and said, “Come here and kiss me, wallflower.” Perfect, I thought, I want to be kissing her when I come.

It was our softest, gentlest kiss of the night: a long, lingering kiss of pure affection. And as we kissed I thought that this confident, beautiful, sexually aggressive woman had had four orgasms. Because of me. The tingling in my groin grew quickly, and I pumped my hips harder, more urgently.