My First Time With An Older Woman

This is the true story of my first time with an older woman, except that I have changed the names of the other women, to protect their privacy, and of the shop, to protect my job. I have embellished details and conversation only where needed to make the story flow; it is largely how it happened. I hope you enjoy reading about my delicious experience.

I had worked in a ladies' fashion shop for two years, since graduating from high school. It mainly caters to the professional crowd, so the clientele is often in their 30s and 40s.

I am sometimes asked to help in the change room. I had previously flirted lightly with a woman if she smiled at me a lot, but nothing close to this had ever happened before.

The Friday afternoon is slow, and I'm bored. Amanda, the other shop assistant, has just gone for her lunch break. I mosey through the shop, straightening the racks three times to pass the time.

Then I see a woman come in. She's very attractive with her curly jet-black hair in a chic short haircut wearing stylish pants and a knit top that displays the shape of her firm boobs. I guess that she is in her late thirties.

I walk up to her, smiling. "Good afternoon, welcome to Millie's. How may I help you?"

She glances at my name tag and then says, "Hello, Mary. I need a bra. I'm in town for the weekend on business and we have a dinner tonight for which I'm going to wear this dress." She holds up a bag. "It's low-cut, and I forgot to pack an appropriate bra."

"I'm sure we can help you. Please follow me." I take her to the aisle between two racks of bras. "Can you hold up the dress so I can see?" She takes the dress out of the bag and holds it up in front of her. I see the plunging neckline. "Oh my, that is deep. I hope we can find one."

"I have worn this braless, which is fine for going out on a date, but this is a business dinner, so I don't want to jiggle too much." Her comment takes my gaze to her boobs.

"Let me guess, you are 34B?"

"Very good, Mary. I guess you've seen a lot of breasts."

I smile and say, "Well it's my business to know." I don't tell her that my girlfriend was 34B, and I see that their boob shapes are identical.

"And you are 32A?" she replies.

I blush and say, "Yes."

I wonder, "Is she flirting with me?" We cast knowing smiles at each other as I flick through the racks, selecting a few candidates. I hold them up to me one at a time, and she selects three.

"I'll show you to the change room." I walk there and open the door.

She asks me, "Can you help me fit them? I know it's important to have them adjusted properly."

"Of course." My heart skips a beat as I close the door behind me, knowing that I will be seeing this lovely lady's naked boobs. I maintain my professional demeanour, however.

I take the dress from her and hang it on a spare hanger. I hang the bras on another peg. She takes off her top, then her bra, which I also hang. Her boobs are lovely - nicely full but very firm, with prominent nipples. I hold one bra up for her to slide her arms into and place the cups over her boobs, trying not to squeeze them as my fingers are itching to do.

I turn her to the mirror and fasten the back clasp on the middle hooks. I run my fingers under the straps in the back and under her shoulders, to remove any twists. Then I reach in front of her shoulders and hike the straps up, pulling the cups up.

"Did I hear a faint gasp?"

I adjust the shoulder straps and then come around to the front to have a look. I frown and say, "They seem loose, don't you think?"

"Yes, perhaps."

I say, "I think I'll go one tighter in back." I return behind her and redo the clasp tighter. "How does that feel?"

"Yes, better, I think."

"Let's check to make sure." From behind, I slip my fingers under the shoulder straps in front and slide them down. My boobs press lightly onto her back, and that makes me shiver with excitement. She leans back, increasing the pressure on my boobs, and I feel sparks from my nipples shoot through me.

My fingers continue inside her cups and swing side to side above her nipples. "The top half seems fine," I say. My fingers push lower, outside her nipples.

I am going mad with desire, my body reacting to my fingers on her boobs and her back against mine. I again slide my finger from side to side, this time over her nipples, which have become hard.

"Mary, stop it!" I yell inside my head. I reluctantly withdraw my fingers and ask, "How does that feel?"

"That felt fine, Mary. Shall we try the next one?"

"Did she mean the fit of the bra or my fingering of her nipples?"

"Of course." I unclasp the bra and let her shrug it off and down her arms. She turns around to face me and smiles broadly as she hands it to me. I gaze adoringly at her exquisite boobs while taking the bra from her and hanging it on a peg.

I put the second bra on her, but she doesn't like it, so we take it off of her.

With the third bra, I repeat the fitting process. My body is now in flames at my desire for her, and I work hard to contain myself. But this time when I rub her nipples, her hands fly up, cupping the bra, trapping my fingers inside. "Don't stop," she whispers. I finger her nipples until she gasps and whispers, "Ah, lovely, enough for now."

My heart is pounding at the knowledge that she has wanted me to excite her nipples. Struggling to be proper, I say, "Let's try on your dress to see if this works." I pull away from her and hand her the dress. She pops it over her head and pulls it down.

She looks in the mirror and says, "I think it is good! What do you think?" She turns around and slowly pivots from side to side.

"Wow, you are stunning. I can't see the bra, which I was afraid might happen. It pushes you up a little to create a delicious cleavage. You are going to turn heads."

"Why, thank you, Mary." She turns back to the mirror and checks herself out. "Not bad for forty-one, eh?"

"Oh, not bad at all! You look hot for any age."

"Well, aren't you so sweet? Okay, I'll take this bra." She pulls herself out of her dress and hands it to me. I hang it back up. She undoes the bra and hands it to me, and I stare at her boobs again. She grins.

She whispers again, "Do you like what you see, Mary?" The question penetrates the haze of my passion. I can't speak, but I nod slowly. "I'm so glad that you do." She puts on her original bra and top. I pull myself together and collect her dress, the bra that she wants and the two rejected bras.

When she's dressed, she whispers, "Are you busy tomorrow night?"

I am shell-shocked that this sexy woman has invited me for, well, I'm not sure what. I think for a moment and say, "No."

"Excellent!" She sits on the bench and pulls a notepad and pen from her handbag. She writes her hotel name and room number down, handing me the page, which I put in my pocket. "Is 6:30 okay?"

"Uh, yes, I guess. I work until 6:00."

"Great. We can order in room service for dinner. Oh, by the way, I'm Sonya."

My body is glowing brightly from the activity of the past few minutes. I open the door and take everything to the desk. I fold her dress and put it into one of our branded bags. I ring up the bra and have her tap her credit card. I toss it into the bag and hand it to her. "Thank you for coming in, Sonya," I say in my practised customer service voice.

She says, "My pleasure, Mary," and then whispers, "and our pleasure tomorrow night." She smiles as she walks out.

My head is spinning at how she has taken charge of my life, at least as far as tomorrow night is concerned. Now that I'm alone in the shop, my professional control evaporates and my body churns. I feel my pussy gush, soaking my knickers.

I stride to the front door, lock it and put up the "Back at" sign and set it for ten minutes. I run back to the staff toilet and yank my skirt down and hang it on the hook. I then peel off my soaked knickers, toss them on the floor and sit on the toilet.

My legs spread and my fingers fly down to my pussy, playing over my dripping lips. I am panting. The image of Sonya's beautiful boobs comes to mind and I imagine sucking and licking her hard nipples while my fingers rub madly.

I plunge two fingers into my pussy, retrieving a copious amount of juice and spreading it over my shaven mound. I rub furiously, making my clit harden and throb under my fingers. I have been so excited by Sonya that it takes less than a minute for me to cum hard.

I stifle a scream as my body shakes. My orgasm pulses through my body in waves that never seem to end. Gradually they subside, and I stop rubbing and just hold my hand on my mound.

My panting slowly eases, but my heart pounds relentlessly. After a few minutes, when I can think again, I grab wads of toilet paper and soak up my sopping wet pussy and wipe off my fingers.

I pick up my knickers, put toilet paper on both sides of the wet spot and twist hard, soaking up as much juice as I can. I dump all of the toilet paper into the toilet and pee. Wiping myself again, little sparks shoot into me again.

I have to sit and calm myself for a few minutes before I can stand, put on my knickers and skirt, flush and wash my hands. I look in the mirror and see that my face is bright crimson.

Finally composing myself, I put on my game face and step to the front door, remove the sign and unlock the door. Fortunately, no customers are waiting outside, so I return to the sales desk and sit, pondering the events of the past half hour.

My body is still buzzing. Sonya has really gotten to me. I wonder how often she seduces young girls like me, not that I'm complaining. She has made me feel so alive.

Amanda comes back from lunch and asks, "Hi, Mary, did anything happen while I was out?"

I suppress a choke. "Oh, just one customer," I reply, not giving anything away.

"Yeah, it's been so quiet. Everyone's waiting for our sale tomorrow."

"I guess so."

"You're almost done today, right, Mary?"

"Yes."

"Why don't you knock off, I can handle it."

"Okay, thanks, Amanda."

I collect my handbag from the back and put Sonya's note in it. I wave at Amanda as I leave and walk to my bus stop. I hardly remember getting home, but I find myself undressing in my bedroom, hanging up my skirt and tossing my blouse on the floor.

I undo my bra and toss it onto the dresser, and strip off my still-damp knickers, tossing them by the blouse. Naked now, I climb onto my bed and replay the scene in the change room.

As I get to the point where I rub Sonya's nipples, I rub my own, feeling them get so hard. When I remember her turning to me, showing me her naked boobs, and asking if I like what I see, I imagine licking them while fucking my pussy with one finger, then two.

I want her so much, and she seems to like me a lot. I mean, why else has she invited me to her hotel tomorrow, told me that dinner will be room service and said, "our pleasure tomorrow night?" As I remember that comment, I rub my clit, pinch my nipple and cum. I hold my mound and cup my boob as I settle.

Glancing at the clock, I see that my sister will be home soon from school, so I crawl out of bed, put on fresh knickers and a tracksuit and dump my blouse and knickers into the laundry basket. I spend the rest of the day in a daze, talking to my sister and mum as needed, but always thinking of Sonya.

I have to finger myself again after going to bed, and in the morning when I wake up. That's not unusual, of course, but it's more intense with the anticipation of my evening with Sonya.

At breakfast, I say to Mum, "I'm going to be in late tonight. I'm meeting friends for dinner."

"Oh, okay. Anyone I know?"

I lie. "People I work with and some of their friends."

"All right, I'm sure that we can amuse ourselves." I smile, knowing that I will certainly be amusing myself with Sonya.

Work is hectic, with our sale bringing in lots of customers. I help a few ladies in the change room but none of them flirts with me. That's fine because I'm charged up, thinking about this evening. Time flies, and it's quitting time before I know it.

I get my bag and wave goodbye to Amanda and Millie, the owner. I head to a café to get a coffee before I walk to the hotel. At the table, I pull out my phone to confirm the location.

I wait until 6:20 then I walk the few blocks to the hotel. I am so nervous that I hit the wrong floor in the lift, but get to her floor and step down the hall. At her door, I take several deep breaths before knocking.

She opens it and says, "Hi, Mary, I'm so glad you could make it." She's still in her work clothes, a well-tailored suit.

"Thanks, Sonya, I'm happy you invited me," I say, with a quiver in my voice.

"Did you have a good day?"

"Yeah, very busy - we had a big sale today. How was yours?"

"Good, thanks, productive but I need to relax now. Oh, before we get too involved, call me so I have your number." I call her and she hangs up. "Got it. Now I'll call you." She does, and I see it, hang up and make a new contact.

"I'm happy you didn't chicken out, Mary."

"No way, Sonya. I've been thinking about you for the past day. I feel sticky, though, can I have a shower?"

"Oh, me too. Let's do that." I blink as I haven't expected to shower with Sonya, but it sounds great to me. She starts undressing, and I watch her lovely body being revealed to me again. She hangs up her skirt and jacket and tosses her blouse onto a chair.

She looks at me and says, "Well, are you going to shower in your clothes?"

I laugh and say, "No, I guess not." I kick off my flats and take off my skirt and lay it over the back of a chair. My blouse follows. She's taken off her bra and I adore her boobs again.

I remove mine, and she says, "Mmmm, lovely little boobs, Mary."

I blush at her compliment and say, "Thank you."

She sits on the bed and peels off her pantyhose and knickers, flinging them on the floor. I see that she has a dark, curly bush, very full but trimmed.

"Do you mind that I'm hairy, Mary?"

"Uh, no, not at all. I just haven't seen a woman with more than a landing strip."

"Well, good. Now let me see what you have."

I take off my knickers and she looks at my smooth pussy. "I hope you don't mind that I shave," I say.

"Of course not, I love variety. My wife is shaved, too."

"Oh, I didn't know..."

"Of course, you didn't, but don't worry, we have an open relationship. I called her at lunchtime today and told her about you, and she is excited for me to be with you."

"Oh, really, well, okay."

"Now let's get clean."

"Did you say we were ordering room service?"

"Oh, yes, that's right. Let's find the menu and order before we shower."

We choose our food and she calls in the order. "They said it would be at least half an hour, so we have time to shower at leisure."

We step into the bathroom. I'm still a bit amazed that this has happened so fast. I'm not nervous anymore; her calm attitude has made this seem so natural.

She gets the stream nice and warm and has me step in. She follows and closes the door. I rinse my face, then I feel her soapy hands washing my back, then sliding down and washing my bum, sliding a finger between to clean there too.

Then her hands reach around me and wash my neck and shoulders, down past my boobs to the stomach then up again, her slippery fingers running over my boobs. I moan a little.

She plays with my nipples and makes them hard, only to abandon them to slide down again, washing my mound. I press against her hand and moan again. She presses in and cleans my lips.

Her hands disappear, and then I feel her washing my legs. I'm a bit disappointed that she hasn't continued the stimulation, but I figure there's plenty of time for that. Then she says, "Okay, let's switch places and you can wash me."

I stand behind her and put body wash on my hands and wash her back and bum like she did mine. Then I get more wash and reach around her, pressing my boobs into her back. As she did, I wash her neck, shoulders and stomach before moving up to her boobs.

I feel her nipples under my palms, already hard. I wash them and then play with her nipples, stroking them and eliciting moans from her. I pull my hand off for more wash, then rub it into her bush, combing it with my fingers. I delight in the novel sensation.

I poke between her lips and wash in there, before completing the wash by soaping her legs.

"Ah, that's lovely, Mary, let's rinse the soap off." She turns all around, letting the soap slide off, then steps aside for me to move and rinse myself. She turns off the tap and opens the door, handing me a towel and drying herself off with another.

She steps out and finishes drying on the bath mat. I gaze at her amazing body, so fit for her age. "Well, are you going to stay wet?" she asks.

I giggle and dry myself. She moves off the mat for me to step out onto it. The room doorbell rings. "Oh, that was faster than they said," Sonya says. She wraps her towel around her and walks to the door and opens it.

"You ordered room service?" I hear a woman ask.

"Yes, we did. Please bring it in." I hear the trolley being wheeled and dishes being set on a table. I'm hiding in the bathroom, a bit embarrassed. I finish drying, and I hear the door close. I step out and see the meal laid out on a small table with a chair on each side.

Sonya has ditched her towel. She says, "Let's eat. It smells good. I'm starved." I drop my towel and we dine naked as if everyone does it.

"Are you okay being naked, Mary?"

"Sure. It's new for me at the dining table, but it's fine."

"Molly and I rarely wear clothes at home."

I can't keep from gazing at her lovely boobs as I'm eating. She looks at me from time to time but doesn't stare like I'm doing. We converse while eating.

"So, Mary, is this your first time with a woman?"

"Uh, it's my first time with an older woman, but I had a girlfriend for a year, so I'm no virgin."

"Nice, are you still with her?"

"No, sadly, she moved away."

"Aw, I'm sorry. You must miss her."

"Yes, of course. We still call and occasionally have a video session, though."

"That's nice. Have you been with anyone since?"

"Only my fingers and toys."

"Haha, well I'm so glad you have joined me tonight."

"How long have you been with Molly?"

"Oh, like forever, about fifteen years. We got married as soon as the law changed."

"Cool, you must love each other very much."

"Oh, yes, we do."

"And you're sure she doesn't mind my being here?"

"No, Mary, as I said, we're open. Our only rule is to share our experience when we get home, telling the other about it. Are you okay with that?"

"Sure," I say. This is all new territory for me, but Sonya is so calm and matter-of-fact about it that it seems fine.

We finish eating. Sonya goes to the loo and comes back. "Do you need the loo, Mary?"

"Yes, I guess I do." I go in, and when I return to the bedroom, Sonya has turned down the bed and is lying on her back. I walk up to the side of the bed and admire her from head to toe.

"Do you like what you see, Mary?"

"Oh, yes, Sonya, very much."

"Well, you are beautiful yourself. Come lie on top of me."

I climb on and lie on her. She parts her legs and my legs fall between them. She reaches up and pulls me gently down to her, our boobs touching. She pulls my head down and gives me a soft kiss.

I kiss her back softly. We slide our lips around each other's, touching very gently. The tenderness of her kiss sends gentle sparks into mine. She slips her tongue out and gently licks my lips. I open my mouth a little and moan into her mouth.

My little boobs press into her larger ones, and the soft sensation adds to my fever. I slide the tip of my tongue out, finding hers. We fence with our tongues until my body ignites and I plunge my tongue into her mouth, kissing madly.