Room Service, with a Smile

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A mature woman gives a special tip for room service.
2.9k words
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"Room service? Yes, room 732. May I please have the grilled salmon with a house salad? Yes, some wine would be lovely, what would you suggest?" Carol breathes into the phone. She kicks her shoes off as she orders. "Excellent that sounds delicious. 30 minutes? Thank you."

Slipping out of her blouse, she drops the phone handset back into its cradle. Carol stands in front of the full length mirror next to the closet of her hotel room and examines herself. Her petite body is framed by the mirror as she removes the bra that seems almost unnecessary, since her small B cup breasts seem to be permanently immune to the effects of gravity. She has always considered herself lucky that she was never "blessed" in the breast department, especially now that she was 42 and her breasts were still as perky as they were when she was in her teens. Her nipples stand proudly atop the upturned mounds, stiffening as she brings her hands up to cup them. Glancing at the clock, Carol turns into the bathroom, collecting the robe hanging from the hook on the back of the door. She walks back into the room and removes her slacks, picking them up from floor and dropping them and her blouse into the laundry bag in the closet. She steps out of her panties and drops them into the bag as well. Now completely naked, Carol examines herself in the mirror again, her hands moving slowly up and down her body, admiring her athletic form. Her smooth legs curving into her hips, her hand continues their journey up her sides and up to her breasts once again. She can easily pass for a woman at least 10 years younger than her current age, if it wasn't for the eyes that meet her gaze. Her eyes and the wrinkles around the edges are the only hint of her age. Lost in her thoughts, she loses track of time, brought back to the present by the insistent knocking on her hotel room door.

"One moment please," Carol calls out, choosing a pair of sheer black panties and pulling them on. The silk fabric feels good as it slips over her bare mound. Carol grabs the robe as she looks through the peephole in the door. She smiles as she sees the skinny young man in the hallway. Carol puts the robe on, letting it fall open. The rough patch of the hotel's monogram scratching over her sensitive nipple and causing her to shiver. She decided to let it stay open, held against her body by only the slight cleavage between her breasts. She looks down, disappointed that the robe is too thick to show her nipples. Taking a breath, she opens the door slightly, just enough to peek into the hallway.

"Hello, maam, I am Thomas, from room service."

"Hello, Thomas," She greets the young man. Carol looks at him sideways and asks, "You seem pretty young, are you sure you are old enough to be serving that wine?"

"Yes maam," Thomas replies, his voice breaking slightly, "I am 18."

"Well, no need to keep you waiting in the hallway, come in," Carol says, stepping back out of the way and opening the door. Stepping into the room, he moves over to the table and sets his tray down. He turns around to see Carol sitting on the corner of the bed, her thighs on either side of the mattress. A gasp escapes his lips as he notices Carol's robe, barely holding onto her breasts. She leans back and arches her back, pressing her breasts against the robe. The boy swallows hard, trying to take his eyes off of the bare skin showing between the openings of the robe. "What can I give you for a tip?" Carol grins knowingly.

"Um, Any... uh, whatever you like, maam," Thomas stutters, his hands opening and closing as he takes in the sight of Carol's black panties.

Carol lies back, stretching her arms above her head. She stretches languidly as she breathes in deeply. Her movements pull one side of the robe, making it slip off of the tip of her right breast, baring her small thighs, hovering over her silk covered sex, the sheer fabric allowing him to clearly see the outline of her outer lips. They move higher, over her smooth belly, before finally settling on her bare nipple. His hands sweating now, he tries to speak but nothing comes out of his suddenly dry mouth. Carol brings her left hand down, gently tracing her fingers between her breasts. She hooks those fingers along the edge of the robe, pulling it aside as she circles the hard nipple of her left breast.

"Isn't there something special I can offer?" she almost whispers, spreading her thighs a little more. The boy takes a small step toward her, his legs moving robotically. He licks his lips nervously as he approaches the woman before him.

"What can I... I mean, what would you, um," his voice trails off into silence.

Rising up and propping herself on her elbows, Carol looks at the young man, "Would you like to touch me?"

Thomas just nods, his eyes wide as he moves closer. His hands shake as he reaches for her thighs. He places his hands on her smooth skin, gently moving them over the woman's flesh.

"No need to be nervous, Thomas, you can touch me," Carol whispers. She sighs as his hands move over her thighs, back forth just above her knees, as if he was afraid to move higher. "Thomas," she asks as his hands continue to shake slightly, "Are you a virgin?"

Thomas just blushes and nods, his hands now resting motionless on her legs.

"Don't be embarrassed, honey, its ok." Carol sits up in the bed, taking Thomas' hands and holding them. "Don't be upset, we are all virgins at first. If this is too hard for you, I can give you a normal tip."

"Um, no maam, this, um, this is ok." Thomas mumbles.

Carol smiles and takes his hands, placing them on her breasts. "Here, they aren't the biggest. I am sure you have seen bigger ones on your computer."

"Well," Thomas blushes again, his hands just cupping her breasts "To be honest, yes, but yours are nicer, I kind of like them like this anyway."

Carol arches her back, pressing her tits into her palms. She sighs softly as his hands finally begin to squeeze and massage her breasts. She shrugs out of her robe, now bare except for her panties. Her hands reach out and run up his legs, pulling his pants tight over his bulge. She reaches for his belt and begins pulling the leather strap out of the buckle.

"How about we get rid of this belt?" she asks, looking into Thomas' eyes. He just stares back and nods. Carol pulls the belt free of the buckle and reaches for the button of his pants. "This too?" He nods again. She quickly unbuttons and unzips his pants, his bulge now concealed only by his underwear. She pulls his pants down his hips and he steps out of them as they hit the floor. "And now these?" She asks again, making Thomas blush. She hooks her fingers in the waistband of his underwear and starts to pull them down. When Thomas makes no move to stop her, she gives a quick tug, slipping them down and letting them drop to the floor on top of his pants. Carol smiles as his 5 inch cock pops free of its prison, almost hitting her in the face. She looks up at Thomas' face as she wraps her hand around the rock hard shaft.

"That feels... "Thomas mutters as his hips begin to shake. Carol just smiles up at him and licks her lips.

"Would you like me to kiss it?" she asks, her lips closing on the tip without waiting for an answer. His knees almost buckle when her tongue swipes over the round tip. "Maybe we should get more comfortable," Carol sighs, moving higher in the bed and inviting Thomas to join her. He quickly pulls his shirt off and climbs in next to her. Pushing him onto his back, she sits up beside him, leaning over and taking his cock into her mouth. He moans loudly as she sucks him deep inside. She pulls her mouth off, looks up at him and smiles. "When the time comes, just go with it, let it out, ok?"

Thomas nods and moans as her lips find his cock again. Slowly she draws him between her lips, allowing her teeth to very gently scrape along his shaft. She feels his hips moving to meet her mouth when she took him deep. She hummed along his length as she moves up and down, swirling her tongue over his cock. She heard him moan and gasp, his body suddenly going stiff. She closed her lips over his glans and wrapped her fingers around his shaft, pumping him into her mouth as the first burst of his salty cum bathed her tongue. She continues pumping and sucking, milking his cock, drawing his musky cum into her mouth and swallowing his gift.

"There, that wasn't so bad, was it?" Carol grins, smiling up and Thomas. The young man's eyes closed tight as he nods. Carol moved up along his body, rubbing her flesh against his. "I guess you have to be heading back to work soon?" She speaks, phrasing it as a hopeful question.

"No," Thomas says softly, "Your dinner was my last service. Clocked out right before I headed up."

Carol smiles mischievously, running her hand up his chest, feeling the slight growth of hair there. "Good, because your tip isn't finished yet." She takes his hand and guides it to her belly, pulling him onto his side as she rolls onto her back. She spreads her thighs, giving him permission to explore. His fingers start to move lower, still shaking slightly. His fingertips brush over the top of her panties. She moves her hands down her hips, lifting them so she can pulls her panties down. She bends her legs, pulling her feet out of the silk fabric and kicking it across the room. Thomas' hand moves lower, brushing over her mound, he teases the little tuft of fur he finds there, amazed at its softness. Her legs spread, inviting him to move between them, an invitation he seems eager to accept. Fumbling fingers brush over her moist sex, almost ignoring her clit. She smiles and reaches down.

"Sit up, honey, let me show you", Carol whispers in his ear. Thomas sits up as she spreads her outer lips. Her fingers move upward along her slit until she reaches the hood covering her clit. She pulls the flap up, showing Thomas her stiff clit. "This is my clitoris, when you are with a woman, this is one part you should always make sure to never ignore."

She takes a sharp breath as his finger glides over the sensitive nub. She moans as a finger slips lower, pushing through her open lips and stroking the entrance to her sex. He strokes along her wetness, gathering some of her juices and smearing them over her clit. Carol moans, her body now starting to thrum like a well-tuned instrument. Her hand reaches out for Thomas, touching his side as it finds its way down, feeling his hip and moving toward his middle. At last, her fingers find his member, feeling his pulse in the veiny shaft as it fills quickly with blood, growing to match his desire. He pushes a finger tentatively against her pussy, feeling her nether lips part to accept his invasion. He pushes it deep, feeling the soft folds of her body surround his finger. He begins to push in and out, his eagerness counter-acting his inexperience. He turns his wrist to move his thumb over her clit, not wanting to ignore the hard button. He moves his finger and thumb in unison, drawing soft moans and mews from the woman next to him. Her hand squeezes his thickness almost painfully.

"Thomas, sweetie," Carol moans, "you are going to make me cum."

Thomas just moves faster, finding that he can push a second finger into Carol's dripping pussy. He starts to thrust hard, his thumb pressing hard against her clit. She lets out a loud breath, then takes a sudden inhale as her body jerks, her climax exploding in her belly. Thomas' hand stops, afraid that he hurt her. He looks at the woman with concern.

"Are you ok, maam?" he asks, worry clouding his brow.

"Oh, I am more than ok, Thomas, in fact, I think you earned an extra tip." Carol smiles, pulling the young man on top of her and allowing him to move between her thighs.

He looks down and sees her hand still stroking his now hard cock. She guides it closer to her wet slit. His breath coming in rapid gasps as he moves closer to her slick sex.

"Umm, maam, shouldn't we use a condom?" he asks nervously.

"I think a young man's first time should be skin to skin, but we can use one if you want to." Carol replies, almost disappointed.

"But," Thomas stammers, "What should I do, you know, when it happens?"

"That is up to you, honey, you can pull out and shoot it on me, or you can stay inside, your choice."

Thomas nods slightly, his arms shaking as he holds himself over her. He looks down between their bodies and watches as she guides his cock to her entrance. Placing the head of his cock between her lower lips, she moves her hands to his hips, holding him in place.

"When you are ready, sweetie, push yourself into me."

Thomas just stares down, his cock throbbing against this strange woman's pussy. His mind is almost overloaded with emotions. He looks up along the gentle curves of Carol's body, losing himself in the beauty of this strange woman. He reaches her breasts, heaving gently, her hard nipples standing proud atop the small mounds. His eyes move higher, up the narrowness of her throat, over her pointed chin. Her lips, parted in pleasure as she breathes deeply. He lets his gaze move higher, looking into the eyes of the sexy stranger. She opens her mouth to say something, Thomas preempts her words by lowering his hips, sinking his turgid cock deep into her welcoming folds. Her hips move up to meet his initial thrust. He stops, letting the feeling of her body wrapped around him sink in for a moment. Her hands move up and over his firm backside, holding him deep inside her body. He leans close, his lips searching for hers. Finding his target, he kisses her for the first time, his heart pounding in his chest. He can feel her hard nipples pressing against his chest and he starts to move his hips. Up and down he moves, picking up speed with each thrust. Carol's body matches his in both speed and desire. Her hips roll up to meet his. She slips her tongue past his lips and kisses him deeply.

Breaking the kiss, she pulls his head lower, needing to feel his lips and teeth on her breasts. He takes the invitation, enveloping her hard nipple with his lips. He suckles at her breast, using only his lips and tongue.

"You can nibble there too, sweetie, just not too hard."

Thomas hears her over the pounding of his own heart and gently bites down on her nipple. She groans and bucks her hips wildly against his, her body growing closer and closer to another climax. Carol can feel the muscles of his ass as she grinds her pussy onto his cock. He starts to shake harder, his own climax growing in his groin. She leans in and nibbles his ear.

"Do it baby, cum for me, on me or in me, you choose."

Thomas grunts as he hears her ask for his seed. He slams his hips against hers, hearing her grunt almost painfully. His body shudders above hers as he hits his peak. Her hands grip tightly on his ass, pulling his as deep as she can, her own climax crashing through her body to match his. He groans loudly as he cums, his cock swelling and pulsing in her tight pussy. He jerks inside her, his cock erupting deep inside her body. She cries out as he sprays her inner walls with his seed, her muscles convulsing around his thickness. They both collapse onto the bed, Thomas panting against her small breast. Her hands move up and down his back, stroking him softly.

"Now that is what I call a tip." Thomas chuckles.

"Cheeky boy," Carol laughs, swatting Thomas' ass playfully.

"I really should get going, ma'am, but I work tomorrow too, and I get off about the same time." Thomas says, rolling off of Carol and sitting up, "By the way, what is your name, seems silly to call you "Ma'am" now, doesn't it?"

"Oh, I think I like it when you call me that," Carol giggles, stretching in the bed as Thomas' thick seed dribbles from her slit. With that, Thomas gets up and dresses quickly. He leans over for a kiss. Carol lifts her head and gives him a peck on the lips. "Well, if I order room service tomorrow night, I will make sure to request you," she promises as Thomas slips out the door, looking forward to work the next day.

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6 Comments
AnonymousAnonymousover 2 years ago

What a way to lose your virginity, wish I lost mine that way! I would have loved to have had this experience and I am sure I would have been a deer in headlights just like him. She was very patient with him and made him feel special! Thanks for the good read.

WatchedBethWatchedBethabout 3 years ago
Sexy

Wonderful story x

AnonymousAnonymousabout 7 years ago

This might only be a story but it really happened to me. At 59 I was much older with huge boobies and a full hairy bush and my young man was 19. I also had room service delivered and 'accidently' let my robe slip open. My young waiter lost his virginity that night and visited me every night for the next week. I gave him blowjobs, rimmed him, prostate massage and let him cum in my mouth and on my boobies. I taught him how to eat pussy and how to pleasure the clitty. I even let him have anal sex and let him shoot straight into my bowels. We even bathed together, peed on each other and tried ever position we could. My lover came to me as a virgin boy and by the end of the week he was a man.

erotikoserotikosover 8 years ago
Lucky fellow!

Ah, this is the stuff of which dreams are made!! Very good story, nicely written with excellent grammar, syntax, punctuation and spelling--all the elements of good writing, combined with a unique plot twist and an age-old fantasy for any young man and the older woman who would teach him the ways of the world. A most excellent job here, and clearly a five star effort. Do keep up the good work and give us readers another go with your fine style.

AverygoodlayAverygoodlayover 8 years ago
Nice!

Hope she teaches him how to eat pussy the next tme.

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