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The Proposition

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He rested his knee on the bed. His palm curved around the back of her neck as he lowered her to the mattress. Grace scooted backwards against the cool sheets until her head met the pillow. Tom leaned over her and planted his hands either side of her body.

He took a moment to drink in the view of her. Her nipples tightened and her skin heated under his gaze. Her body shifted restlessly beneath him until desire and curiosity got the better of her. Grace's eyes darted down his body, to the pulsing shaft between his thighs. Her cheeks flushed at the sight. "I want to touch it," she said.

Tom straddled her and ran his fingertips from her neck down to her belly. He leaned in and flicked his tongue over her nipple. A sudden smile broke across his face. "Touch what?" he asked, raising his brows.

Grace closed her eyes. He understood full well what she meant. For some reason he wanted her to say it. "Your cock," she said softly, building the courage to look at him again.

His elbows came to rest either side of her head. His chest brushed hers as he pressed a kiss to her lips. "Do you have any idea how appealing you are right now?" he asked. He moved his mouth over her throat, licked the lobe of her ear. "Anywhere, Gracie. Touch me anywhere."

She smiled. Grace looked into his eyes and spread her palms over his chest, enjoying the crinkling of hair under her fingertips. She caressed his nipples, taking pleasure in the tremor that ran through him. "I like your body. Always have."

He took her mouth with gentle abandon, pressing his tongue against hers. "I've wanted to get my hands on you for years," he said against her lips.

"Really?" Grace let her palms glide over his stomach as he hovered above her. His muscles clenched beneath her fingers. She loved the way every small touch garnered a reaction. "I never would've guessed. You've always been such a pain."

"What can I say?" Tom dipped his head and licked her nipple. "You bring out the best and worst in me." His breath was warm against her skin. He drew her nipple between his lips, suckling on the tender bud.

Her mouth dropped open and her hips slowly undulated. She followed the line of dark hair down his stomach until her hands wrapped around him. His groan of appreciation vibrated against her breast. He was hot and hard. He gave a shallow thrust into her palm and tugged on her nipple with his lips.

The breath caught in her throat. The skin of his shaft was silky smooth. She ran her fingertips along the length of him and tentatively stroked his balls. Moisture dotted the head of his cock. Grace used her thumb to spread the slick droplets. "Am I doing this right?"

He lifted his head and nipped at her lower lip. "You're doing everything right," he said. He lowered his body until his chest pressed against hers and her breasts flattened under his weight. "You're perfect."

She smoothed her hands over his back as tenderness swelled inside her. He pressed his lips to hers and sank his hands into her hair. His tongue swept over hers, his erection nudging her belly. She writhed beneath him, desperate, yearning for something she'd never experienced.

Grace parted her thighs and broke the kiss to gasp as he settled between them. His cock probed her entrance, and she wedged her hand between their bodies to touch him again. She loved the feel of him, the heat, the silky skin. Her fingers encircled his thick length, and realisation had her brows drawing together. "Are you going to hurt me?"

Tom pulled back from her and kissed the frown from her forehead. "I'll try my best not to." He scanned her features as if searching for something in her expression. "Do you still want to do this?"

She nodded and squeezed his length, sliding her thumb over the slick tip again. "I don't want to wait any longer. I need you inside me."

He made a deep sound in his throat and captured her mouth with his. His lips moved over hers patiently, thoroughly, stirring chaos inside her all over again. She swept her hands down his back, curving them over his ass. He rubbed his cock against her pussy, making her hips move and her breath catch as he slid inside her just a little. He moved his attention to her breast, working her nipple into a taut, aching peak with his thumb.

She felt the mounting pressure. Bit by bit he pushed further inside her, and she stretched to accommodate his girth. It wasn't an easy fit, but his hands and mouth kept her so busy she could barely concentrate on the discomfort.

When he finally bottomed out, Tom pulled her hands up beside her head and interlaced his fingers with hers. He leaned back and looked into her eyes. "We made it."

She smiled and wrapped her legs around his waist, hooking her ankles at his lower back. "It feels strange, almost like you're too big."

He gave a soft laugh. "Gracie, you're so good for my ego." Tom squeezed her hands and pulled back so he could slide into her again, slowly, as if he was worried he might hurt her.

She bit her lip and closed her eyes, surprised to feel the burn, but each time it got a little easier, and it didn't take long for her to adjust. His thrusts soon became slick and smooth, and she started to feel pleasure rather than discomfort.

Grace opened her eyes to find him watching her.

"Am I hurting you?" he asked.

"No." She pulled her hands from his and shook her head with a smile. It wasn't nearly as bad as she'd expected, and she couldn't imagine sharing this moment with anyone but him.

Tom leaned on his elbow and wrapped his other arm around her. He pulled her close as he thrust gently in and out of her. "Does my cock feel good inside you?"

She looked into his eyes while his hips pumped against hers and nodded. "Does it feel good for you?"

He gave a hard thrust that had her mouth dropping open. "You have no idea."

He stroked her hair, kissed her lips. He whispered words of encouragement to her, all the while invading her body with his hot length. Grace was swept away with the pleasure of it all. His hair-coarsened skin grazed her softness. His rasping stubble made her feel so feminine. Her every sense was heightened.

He buried his face in the curve of her shoulder and kissed her throat. His cock withdrew almost all the way and plunged back inside her. Grace tilted her head on the pillow and gasped. The gentle pumping of his hips made her moan; his powerful thrusts made her stomach flutter and pleasure streak through her.

She had a suspicion he was holding back, taking it slow for her benefit. She could feel it in his bunched muscles and the strained breaths against her neck. "Can you... can you do it harder?"

Tom kissed the underside of her jaw, flicked his tongue over her chin. He dipped his hands into the sides of her hair and held her still. "You want it a little rougher?" His eyes met hers and a corner of his mouth lifted in a sexy smile.

The deep tone of his voice sent a shiver running through her. Her nipples tightened. Grace barely recognised the breathy whisper that came next. "Yeah, I do."

He rested his forearms either side of her head and ground his hips against her. "You're just full of surprises, aren't you?" Tom pressed a kiss on her brow and shoved his length hard inside her. "Tell me when to stop."

She slid her hands along his back, hooking them over his shoulders. "I won't."

He spoke softly against her ear. "I like a challenge," he said. With that he scooped her rear into his palm and lifted her slightly from the mattress. He raised his chest from hers and braced himself on one hand. Tom looked into her eyes and drove his cock inside her.

Grace felt her back bow with the pressure. Her initial pain was long forgotten, now replaced by the most intense pleasure. Her head tipped back, and she cried out. She pulled her hands from around him and swept her palms over her breasts, caressing her nipples, rubbing her fingertips over the hardened buds. Her body jolted with the strength of his thrusts.

"You like that?" He watched her closely. Through the haze of pleasure it dawned on her that he was keeping a close eye on her, looking for any signs of discomfort.

"Yes." Her breaths panted from her. She turned her head restlessly on the pillow and pushed her breasts together, teasing her nipples.

"You want more?"

Her body twisted and she let out a loud moan when he altered the angle of his thrusts.

"I guess that answers my question," he said. Tom settled back on his haunches and slid his hands up her thighs. He gripped her waist and pulled her back against him to meet each glide of his pumping hips.

She met his gaze. The intensity of the eye contact alone almost made her lose the little control she had left. Her hand drifted down her belly, fingers dipping into her heat. She caressed the place where their bodies joined, enjoying the feel of his slippery cock as it plunged and retreated.

"You're gonna make me come doing that." Tom's mouth curved in a half smile. His fingers dug into her hips and tension gathered in his forearms.

For some strange reason, she felt proud of herself. Grace returned his smile and rubbed her fingertip over her engorged clit, sliding through her wetness. An ache built inside her, gaining pressure until she felt she might burst. Her limbs tightened. She flicked her nipple and stroked her clit. Her lips parted, and she watched him through half-closed lids.

A vein pulsed in his neck and his jaw clenched tightly.

Grace arched her back and pushed hard against him. Her hips lifted from his hands and she let out a long, guttural moan as her body convulsed.

"Oh, Christ." Tom leaned back over her, pressing his body along the length of hers. "You sexy, sexy woman."

He crushed his mouth to hers as she shuddered beneath him, keeping her in place with his arms braced either side of her. His continued thrusts drew aftershocks that left her weak.

Grace wrapped her legs around him and gripped his forearms. He let loose then, the breath shaking from his nose as he kept his mouth joined with hers. His cock pulsed as he thrust hard and emptied himself inside her. His body tensed for one long moment, and he groaned deep in his throat.

His limbs suddenly seemed to turn to water, and he collapsed on top of her. His stomach clenched against hers as he drew in air.

Grace leaned her head back and stared up at the ceiling. She swept her hair from her forehead and stroked his back while her pulse settled. Her body felt used... in a very good way. Relaxed and languid. She was tender now the passion had subsided, but it was a pleasant pain; a reminder of the wonderful moment they'd shared.

And now it was over.

Grace shifted beneath him, uncomfortable and awkward now their desire had been spent. She didn't want to overstay her welcome, but she didn't want to run like a scared rabbit either. She'd been under no illusions going into this; she wouldn't start entertaining thoughts of a future now.

"What happens next in these situations?" she asked softly. "Am I supposed to go?"

"Like hell." Tom kissed her neck and rolled onto his back, dragging her with him. He encircled her in his arms and held her close. Her heart hammered with hope as she leaned on his chest. He swept his thumb over her cheek and gazed at her. "Stay with me, Gracie."

She watched him in silence, surprised by the look of uncertainty in his eyes. She'd never known him to be hesitant about anything. He'd been tender and kind today when she'd needed him most. He'd looked after her like she'd known he would.

A slow smile spread across her face as he urged her mouth down to his.

Maybe she'd entertain thoughts of a future after all.

12
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140 Comments
AnonymousAnonymous3 months ago

It kinda surprised me it was so slow and tender. It moved at the perfect pace. The descriptions were perfect, It was a pleasure to read and I would like to read more from this author.

AnonymousAnonymous5 months ago

Such a sweet, tender, although hesitant story. He is surprised as she is. Yes, I see a future.

AnonymousAnonymous5 months ago

Nice story. Real simple. Realistic. Could have had a little more of her thoughts as things were progressing with and within her. It was her first time. The first time for women has a little bit of fear of possible pain and not knowing what to expect and feel like when he is inside her. You can tell this story was written from a male's point of view. He was considerate of her, respected her for offering herself up to him, but still her view in more detail given the story more punch.

strawboystrawboy6 months ago

A fun read of a well written story.

100faces100faces7 months ago

Touching story. One of the few stories I have read that needs to contine. Being so many years later l doubt it will be. I can only hope. If still follow your feed back just maybe. I will read more of your stories.

LudvigBlomSELudvigBlomSEabout 1 year ago

I liked it nut with a feeling that a page or two is missing ;-)

BigotedeFocaBigotedeFocaabout 1 year ago

Longer it went, hotter it got, surprise surprise! You do nice work, thanks for sharing.

AnonymousAnonymousover 1 year ago

I like the improvements that have been made to an already very good story. You want to root for them to stay together.

MikeykeithMikeykeithover 1 year ago

FREAKIN' AWESOME.

AnonymousAnonymousover 1 year ago
Great 5 stars

Love you Lisa...

roveroneroveronealmost 2 years ago

Just as sweet ...the third time?

Can't remember when I first read this...you hit it out of the park.

UncertainTUncertainTabout 2 years ago

Excellent little story, just right.

AnonymousAnonymousover 2 years ago

Lovely premise.

Nicely written.

Wondering why she wouldn't have been more inquisitive when handling his cock. Do you like it when I do this? This? Is it better this way? This way?

Wondering why she didn't even think to kiss it.

Not even a bit of reluctance/concern concerning possibility of pregnancy? Odd.

He's wanted to get his hands on her body for years. She doesn't wonder what he's wanted to do to/with her?

Four stars.

AnonymousAnonymousover 2 years ago

Wow I really need Tom although I lost mine years ago now with a dud

AnonymousAnonymousalmost 3 years ago
WOW the sweetest story

It's obvious she already loves him and what she doesn't know is he loves her to and has for a long time. Yes they do have a future.

a_reader_from_germanya_reader_from_germanyalmost 3 years ago

I see this story has recieved many comments of approval. Since I have nothing to add really, I just want to join the choir of praises and to say thank you, from the heart of my bottom, or was it the other way around...? But heck, this tale of losing something, but gaining so much is really beautiful on several levels. I will be re-reading this more than once in the future.

Sman4444Sman4444almost 3 years ago

Wow - such a wonderfully romantic story - great work!

Marshall52Marshall52about 3 years ago

Excellent story and perfect descriptions of first time lovemaking. It was like I was there in the room with them. This is one of my favorite all time stories on Literotica.

Thank you Lisa.

mrdata9770mrdata9770over 3 years ago

(7/15/2021)

This story was sexy, tender, romantic, with also a bit of suspense, and so was very well done. This was a very enjoyable read. Thank you for submitting your story. What more can I write? I loved it.

JBluejayzzJBluejayzzover 3 years ago

Very nicely done. This is one of the most erotic and intense depictions of a young woman giving up her virginity that I have ever read. This is not just sex and fucking; it is a wonderful story about making love. I was right there with her when she reached down to feel where their bodies were joined. It's been 50 years since my first time, but I could feel it when they came together.

XactoXactoover 3 years ago
That was lovely.

I’d read a few of your pieces before I had an ID. I loved this story. Sweet and sexy.

GoofyRobGoofyRobalmost 4 years ago

WOW, WOW, WOW. Nicely done - that's what she said.

AnonymousAnonymousalmost 4 years ago
WOW 5 stars

I have read this little story many times. It's one of my all time favorites and Lisa is an all time fav author. I hope she is successful as an author on pay sites.

WisheswerehorsesWisheswerehorsesover 4 years ago
Awesome

Just perfect in too many ways to count. Favorite story.

thisisme115thisisme115over 5 years ago

I read this story all the time and it’s my number one go to story .

AnonymousAnonymousover 5 years ago
I love this story 5 stars

I've read it many times. I read it when I need to feel good. It's obvious Grace loves him and now he loves her. He's wanted her and then she gave him permission. So this is a First Time story, but a Romance too for me...

RegretsRegretsover 6 years ago
The right way round. Forward planning.

This is how a young woman should conduct herself. Grace has left it rather late,23,but she got the main parts right. Too often,women tell of their first time,chatted up by some strange boy and then somewhere quiet for a few minutes,all over in seconds and feeling unsatisfied. And still feeling wronged,years later. Some forward planning is required. The girl should slowly realise that she would like it to be...him! And she may be shocked by this inner voice which tells her who HIM is to be. He might be the wrong person entirely,apparently,her best friends father,or the quiet,efficient,very competent,but dull young lodger who lives by her piano teacher,but his strange violet eyes...ooohhhhh.

The absolute wrong way for a woman to go about her first time,is to wait for that moment when she is chatted up and suddenly the “compelling” aspect which women admire in men,shows itself,and she can not say NO,just then,but regrets the hurried experience ever afterwards. But,this time,things were done the tight way round and Grace made her choice being in tune with her inner voice and making herself responsible for her successful first fucking. All credit to her. The passivity,in women,is what brings about the unsatisfactory first time that many remember. If they,instead,made a habit of coming to conclusions about all sorts of matters in these inner dialogues that we have I feel sure that happy first- time experiences will become more common. Passivity should be abandoned and Acting Deliberately,should be adopted. A girl who knows what she wants is made more attractive in that way alone.

getalyfe1getalyfe1almost 7 years ago
Hot

That was the hottest story I've ever read! So caught up in your descriptions that I could feel it myself! Fixing to look you up, hopefully there's more stories, but if not, please please write more.

benjie4benjie4about 7 years ago
Criticism?

Sorry, I know you ask for constructive criticism, but I am hard-pressed to find anything to complain about. A few obviously British words and phrases, but that is not by way of criticism. Great job: lovely descriptions of their surroundings and their emotions and reactions. I will certainly read more.

TwilightfanTwilightfanover 7 years ago
2nd?

I don't like to beg, but, Please, Please, Please, write a 2nd!!!

lowkeyonelowkeyoneover 7 years ago
WOW

What a great, well told story. Excellent.

I knew ' Orie ' has good taste.

AnonymousAnonymousover 7 years ago
I love this story

I've read it several times because it makes me feel really good. Grace picked Tom because she is in love with him and always will be...the rest of the story is left to the imagination of the readers and a million different ideas...

Luvu78Luvu78over 7 years ago
Very well written

The clarity of your writing is extraordinaty. The story line quite believable. Keep practicing your art.

MisshotlaramieMisshotlaramieabout 8 years ago
Wonderful

I love your writing in this story. Tenderness, humor, passion. Perfect.

AnonymousAnonymousabout 8 years ago

Can this be part of a series? Please?

It was so good! The sex and the characterizations.

AnonymousAnonymousabout 8 years ago
Nice

Well written. Very nice story! Hope to see more stories.

AnonymousAnonymousover 8 years ago
Goodonya

Beautifully written.

MissClassyMissClassyalmost 9 years ago
Lovely!!!

I love the way you write!!!

TheHentaiTheHentaiover 9 years ago
experienced?

This work of art is actually a more than likely thing to happen. You know best friend bother crushing on lil sis's friend and all. I think you may have experienced this or you have a damn good imagination and writer

happy_blokehappy_blokealmost 10 years ago
Very nice story

Well written, erotic, arousing. Thanks for writing.

AnonymousAnonymousabout 10 years ago
Love your work.. :)

Great story beautifully told...keep up the good work.

AnonymousAnonymousabout 10 years ago
Lovely

This was so sweet.

AnonymousAnonymousover 10 years ago
by Malvo; Wonderful and Intense

Your story grabbed my attention not losing it for a moments notice, great work :)

rightbankrightbankover 10 years ago
just enough

for a start

WishFullWishFullover 10 years ago
Loved it

Excellent!

AverygoodlayAverygoodlayover 10 years ago
Wonderful

Wonderful! Full of love and tenderness for a young womans first time.

You write so well it's like being there watching it happen.

I know that I'm an old romantic but these are the stories I love best, there is no need for the huge cock and tits to make a story great and you DO make a story great,I'm just sorry I couldn't give you more than five stars.

Please never stop writing these type of stories.

arrowglassarrowglassalmost 11 years ago
An exquisitely sensual start..........!

What an intoxicating beginning...I sure hope their sublime passion continues in another chapter!!!!!!!!

OleguyOleguyalmost 11 years ago
O.M.G.

That was wonderful, Tom was a blessedly lucky man. Gracie was also blessed, how wonderful when she saw herself in the mirror as a woman for the first time,

Great job Lisa.

smc331smc331almost 11 years ago
Just wow...

You paint incredibly compelling word pictures - I've read before that "the mind is the body's most erogenous zone" - after reading this I have to agree. Absolutely, stunningly beautiful.

TwilightfanTwilightfanabout 11 years ago
CH. 2

I loved this so much!!! Why can't all men be like that for her first time???

Please, please, please, please, please, please, please, please, please, please write a Ch. 2!!!

dairetodairetoabout 11 years ago
Wow

This story was so erotic.

And so beautiful.

I would have loved there to be more about Tom and Gracie.

EuphoriaSlam69EuphoriaSlam69over 11 years ago
Year after year this story always excites!

It never gets tired! LOVE IT!!!

StoryTeller2002StoryTeller2002over 11 years ago
:(

I accidentally only have you 2 stars. You deserved 5 :)

AnonymousAnonymousover 11 years ago
Fucking Amazing

This is so reminiscent of the first girl I ever fucked, we were both fifteen and both of us were virgins. A night in a tent I shall never forget. Thank you Lisa for helping me remember it. PS Although I am married and that very first girl is too, we are still fuck buddies. Some things you just cannot let go of!

AnonymousAnonymousover 11 years ago
Nice. Tender.

Bot the sex happens too fast to be maximally erotic. It's be better with extended foreplay, step by step, what she felt, what he felt.

LadyFalconLadyFalconalmost 12 years ago
This will be the second time I've commented on this story...

I have had this story in my favorites for a very long time and have come back to it on several occasions. I've sent the link to a few friends over the years to share my enjoyment. I still get wrapped up in the excitement, her nervousness at first and then her pleasure. All your stories are good but this is still my favorite and I still want to hear the story from his pov. I was very glad to see some recent posts by you and have enjoyed/commented on them. Please keep writing and posting. :-)

phil2213phil2213almost 12 years ago
Absolutely a tender loving innocent story! Superbly written

The author captured a moment that is so important in the adventure of every young ladies life when the transfer of little girls fantasy to becoming a woman. The loss of virginity is a monumental step for most and the author elucidated with surgical precision the emotional and erotic nature of this incident. The author was empathetic to the handling of this matter in the construct of the maturity of the characters and the solemn handling in the respectful nature the characters held for the act and eachother. The author made you feel the gravity of the importance while pouring on the flow of the erotic nature of the act in a slow moving flowing anxious buildup to a crescendo of good delightful spirit in the ending. The artistic nature in handling a story of this nature was nothing short of sheer genius. This author is by no means run if the mill in the least bit. The quality of this story is not something that is learned from University training but an innate gift that some icons are blessed. The fact that I had an opportunity to read this is an unexpected happening especially for this site or any site in the network. Thank you author and may you write on and on and on. You're a phenomena!!!!

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