Alluring Barista Ashley

She was very cute, kind of petite, and even though she was rather plain looking, and came across very innocent, she had an allure about her. She seemed kind of shy but I sensed she was hiding a more playful side. Her name tag simply said, “Ashley,” and as I continued to check her out as she made my drink, I couldn’t help but smile thinking how nice it would be to be with her.

Like I said, I could tell she had a slight frame under that green apron, but the way she carried herself was attractive. She had hazel eyes and dark brown hair that she always had in a ponytail, and whenever she would French-braid it, I found her very sexy. She had a nose piercing and I could see she had a few tattoos on her arms, which only exemplified that she probably had a wild side.

From the first time I saw her, I was curious, and tried to visit this particular Starbucks whenever I could, just to see her, always wanting to interact with her. As time went on, I found myself obsessively wanting to see Ashley every morning, hoping I’d find a way to ask her out, but it never presented itself.

I always tried to flirt with her and made sure to give her a generous tip after ordering, always thinking she’d realize I was interested. I didn’t want to come across desperate and never came right out and asked her but continued to search for ways to let her know I was attracted to her. I even went so far as to contacted the manager and Starbucks directly to compliment her, again hoping she’d notice the attention I was trying to give her, how could she not.

I wanted her to feel obligated to reach out to me too, but she never did, until one afternoon, I decided to stop in to see if she might be there as I headed home from work,. It surprised her a little I think as I walked in, but after a double take, she smiled. Approaching the register, I tried act nonchalant but eventually as we looked at each other, we smiled. It was obvious she wasn’t expecting to see me in the afternoon, but after a pause I innocently asked, “How’s it going?”

This made her blush a little, and then after giving me my coffee, I said thanks and casually went over to sit at one of the tables. Sitting there contemplating my next move, I hoped she might get the hint and come over and talk with me. Continually looking over, trying to get her attention, she eventually did venture over and when she asked, “Can I get you anything?”

Searching for something to say, I nervously shifted in my chair. I didn’t know what to say, and as I looked at her, I hoped the words would miraculously come to me. I wanted to ask her out and after exchanging some simple pleasantries, I nervously asked, “Do you want to sit down.”

Smiling, she glanced back at the counter briefly and then feeling a little obligated, she eventually sat down. I could see she too was searching for what to say, and then when she blurted out, “Thanks for sending those complimentary emails to my boss.”

I couldn’t help but look at her questioningly and thought to myself, “How did she know,” but quickly realized it was probably obvious.

As I looked at her, struggling for what to say, she questioningly asked, “It was you, right?”

Smiling I nodded and said, “Yea, you’re a great barista.”

This made her smile too and after a second or two she again said, “Thanks.”

As we talked, I couldn’t help but nervously flirt with her, all the time hoping to get up the nerve to ask her out. However, I could see she too was a little nervous, and soon said, “I better get back to work,” as she stood up.

I’m sure she realize there was a mutual attraction, and not wanting to loose the opportunity, I said, “Thanks for talking.”

Smiling, Ashley said, “Sure,” and just as she turned to leave I boldly asked “Hey, would you like to go get a drink sometime and talk a little more?”

Ashley seemed hesitant but then after looking over at her colleagues by the counter, she turned back and smiling simply said, “Sure.”

I couldn’t believe it, but then as we looked at each other, Ashley glanced at her watch and said, “My shift is over in a little bit.”

I was speechless, but then she asked, “Do you want to wait.”

I couldn’t believe it, but then realizing it was my chance, I smiled and confidently said, “Of course.”

This made Ashley smile and after a subtle little nod, she went back to work.

“Oh my god,” I thought as I sat there nervously watching her walk away, I couldn’t help but continually look over at her.

She was talking with some of the other baristas and when they looked over at me smiling, it was obvious Ashley had told them what was going on.

I’m sure she could tell I was much older and I tried to ignore the fact, hoping it wouldn’t get in the way, but it was constantly in the back of my mind.

Eventually her shift ended, and when she came over to where I was sitting, I smiled at her and stood up to greet her. Taking off her apron now she asked, “Where do you want to go?”

I couldn’t help but check her out as she rolled up her apron, wanting to soak her in. She really was small, but I was so excited, and not realizing I was staring, I hastily looked back up. I was a little embarrassed, but smiling she suggested, “How about Chili’s,” and then explained, “It’s close by.”

It sounded great and after a smile and a nod, I agreed. Ashley continued to smile and as we headed out, she waved to other baristas. In the parking lot I asked, “Do you want me to drive?”

Ashley immediately said, “Why don’t you follow me.”

At first, I was a little worried, but then realized she just wanted to drive her own car. It was probably best, I couldn’t blame her and being I was really nervous, I simply said, “Okay.”

Following her, I felt this was my chance, and not wanting to blow it, I tried to gather my composure before we got there. I had wanted this and as we walked into the restaurant together, I hope the right words would find there way into our conversation.

We decided to get a booth and after ordering some drinks, and an appetizer, we immediately started asking each other a lot of questions, trying to get to know one another. I was curious about her and I think she was too. I wanted her to know I was interested in her too and when I eventually asked, “How old are you?” There was a brief pause.

Ashley then smiled and asked, “How old do you think I am?”

I didn’t want to embarrass her or myself but eventually said in a questioning voice, “25?”

There was another pause but she again smiled and said, “No, I’m 22.”

Ashley definitely carried herself more mature, or maybe she was nervous, in either case, being she was so much younger she still seemed very innocent. As she looked down, sheepishly smiling, I nervously thought, “There’s no way this is going to happen.”

I wanted to keep our conversation going, and as I searched for what to say, I grabbed my drink and took a big pull off the straw. Ashley immediately looked back at me and as I put my drink back down she asked, “How old are you?”

Nervously looking over at her, I smiled and said, “Well, I’m a lot older.”

Smiling, Ashley pressed me, saying, “Come on, you’re not that old.”

I didn’t want to tell her just how much older I was but I could tell she was waiting for me to say something, and after clearing my throat, I smiled at her and hesitantly said, “I’m 50.”

She seemed a little shocked but after a moment, she smiled and said, “You don’t look that old,” and as I continued to look over at her, she said, “I thought you were maybe in you late 30s.”

Cautiously smiling as we looked at each other I jokingly asked, “Maybe I’m too old for you? “

Right away, Ashley said, “Too old for what?”

It was obvious she was trying to get a reaction and feeling myself blushing as I looked at her, she giggled and took a drink of her Coke and whiskey. Nervous, I too took another big drink and then immediately looked around and motioned for our waitress so I could order another.

I was worried she might be playing me because there was a long pause, and I figured since I was so much older, it was never going to happen, not now. However, as we both searched for something to say Ashley asked, “Are you married?”

“Oh no,” I thought, because I had been married, and even though I had been divorced for awhile, I figured the minute I told her it would be a turn off.

However, as I explained, she seemed to listen intently and not wanting to scare her off, I tried to make light of it by asking her, “Are you married?”

I knew she wasn’t because she wasn’t wearing a ring and after an inquisitive little smile she giggled and said, “No.”

Needing to steer clear from anything that made me seem too old, I followed up by asking, “Do you have a boyfriend?”

I wanted to find out more about her and as she smiled and leaned toward me she said, “Yea.“

I was a little taken aback and not knowing what to say I thought,“What should I do now?”

However, before I could say anything, Ashley blurted out, “Don’t worry, it’s okay.”

She smiled kind of shyly and when I saw this, I suddenly felt, “Yea, maybe I do have a chance.”

Ashley then suddenly asked, “Do you have any kids?”

Yea, I did have a daughter, but again not wanting to come across too old, I decided to tell her no.

I’m sure she could sense a little apprehension on my part and seeing it was starting to get late, I thought, “How can I get her to come over to my house?”

It was nice to finally be with her and feeling no pain, and not wanting to appear desperate or turn her off in anyway, I nervously tried to think of what to say. However, I didn’t have to worry, because Ashley suddenly asked, “Do you want to go over to my apartment?”

“Really,” I thought, “of course I did,” and when she said, “It’s not far,” I desperately tried to hide my excitement.

Continuing to try to stay composed as I looked at her, I smiled and said, “Sure, that sounds good.”

Ashley immediately smiled too and then replied, “You can follow me, okay?”

It was hard to contain my enthusiasm and yea, I was nervous but I had wanted this and after signaling for our waitress, I quickly paid the bill and we left.

At her apartment, she motioned and said, “Come on.”

Smiling, I walked toward her and as we headed in the door together, we immediately went up a flight of stairs. Her apartment was on the second floor, and as we went in, I quickly looked around. It was modestly furnished with a small couch, an arm chair, a couple tables, and a big screen TV.

Following her toward the kitchen area, she asked, “Do you want anything to drink?”

Moving closer to her, I didn’t reply right away, and feeling a little bold or maybe a little drunk, I thought about making a move. Ashley now turn to face me and seeing me smiling she asked, “What?”

Continuing to smile, I put my hands on her waist, and as I went in to give her a kiss, Ashley leaned away and looking at me she asked,“What are you doing?”

Smiling, I quickly responded, “I want to kiss you,” and as I backed her against the wall, Ashley now smiled shyly.

Leaning into her again, she closed her eyes, and as I gave her a subtle little kiss, I couldn’t help but smile. It was nice and after giving her another kiss, she open her eyes and looked at me smiling. Smiling back, I glanced down at her chest, and then reaching my hands up, I started feeling on her tits.

She really was small, but her boobs were definitely firm, and being she wasn’t wearing a bra, I could feel her hard little nipples pushing against her top, which made me hesitantly look up. I was apprehensive, but seeing she was smiling kind of sheepishly,I smiled too. Kissing her again, I let her erect little nipples slip between my fingers, and as I gave her tits a little squeeze, Ashley looked down. It was only for a moment and when she looked back up, she raised up on her tippy toes and gave me a kiss.

Pushing my tongue into her mouth, Ashley hesitated at first, but eventually our tongues playfully twisted in each other’s mouths. Ashley now put her feet flat on the ground, which made me have to lean down as we kissed. It was awkward, but I didn’t want to stop, and when I did lean away for a second to catch my breath Ashley asked me, “What?”

Smiling and shaking my head, I moved my hands down to her waist and then sliding them behind her, I grabbed her plump but firm little ass. It made her smile and when we again kissed, I pulled her close. I wanted to fuck her, but I didn’t want to push it, and so I backed away, thinking I should slow things down a little.

It was nice to be with her and I didn’t want to ruin it, but I think Ashley sensed a little nervousness and when she said, “Let’s go to my bedroom,” I couldn’t help but smile.

Ashley now turned and as she took my hand and led us toward what I felt was her bedroom, I was nervous but excited. As we went through the door, I let go of her hand and immediately held her waist from behind. Her room was dark, but there was just a little light coming in from down the hall. As we stopped, I moved right up behind her and leaning down, I kissed her neck. Ashley instinctively turned her head slightly giving me better access, and after moving her hair out of the way, I continued to kiss her supple neck.

Continuing to suck and nibble on her neck, I brought my hands up to again feel on her little tits. Ashley immediately turned to face me and after a subtle little smile, she gave me a sly look, and then looking down, she reached down to feel on my crotch.

I was hard, and it wasn’t long before Ashley’s hand was on it. Inching back a little, we looked at each other, but then looking down, wanting to see, as she felt on my cock, I could see she had a big smile on her face. As she kneaded my cock through my pants, I watched, hoping she wouldn’t stop.

Giving me a quick little kiss, Ashley suddenly went down to her knees, and started unbuttoning my pants. As she got them unbuttoned, she glanced up at me smiling, and then her focus returned to getting my pants down.

As she unzipped them and then tugged at the legs, I reached down and after wiggling a little, I let them fall to the floor. Stepping out of my pants and adjusting my boxers, Ashley immediately started feeling for my cock again with both hands. When she eventually got ahold of it, Ashley started to rub it and then as she pulled it through the little flap, I couldn’t help but watch as she stroked and pulled it, making sure it was all the way through the flap.

Looking up at me briefly and seeing me smiling as I watched, she gave me a sly little smile. Reaching out, I placed my hands on her shoulders, and as her gaze dropped down to my cock again, Ashley subtly pulled the skin down slightly, exposing the head. Yea, I was circumcised, so it didn’t take much and then as she took it in her mouth, I looked up with my eyes closed.

I couldn’t believe it, it felt so good, and as she stroked it, letting my cock move in and out of her mouth, I again thought about wanting to fuck her. Yea, I wanted to cum, but not yet, and after a few minutes, I gently pulled her to her feet.

She seemed a little confused, and after asking, “What’s wrong,” I kissed her and said, “Nothing’s wrong,” as I tucked my cock back into my boxers.

Looking down, she smiled, and then as I tried to take off her top, she smiled and instinctively lifted her arms, and let me slip it over her head. After tossing it toward her dresser, I looked back at her. I didn’t want to let on just how much of a turn on she was, but she really was cute, and seeing her hard little nipples pushing against her lacy little maroon camisole, I couldn’t help but reach up to feel on her tits.

Ashley put her hands on my chest now too and then after feeling on my chest, she tried to take off my shirt. Helping her, I pulled it over my head and as I dropped it to the floor, she immediately felt on my chest, running her fingers through the sparse little tufts of hair I had.

She was smiling and then as I tried to unbutton her pants, she stepped back, allowing me to get them unzipped. As I inched them down, I looked up when I noticed her panties were coming down too. Ashley felt it too and immediately reached down and adjusted them as her pants fell to the floor. Her panties matched her camisole, lacy maroon and sheer. Standing back up, I quickly lifted her on the bed and after scooting her back, I moved until I was between her legs. Smiling, I moved her further up on the bed and then as I climbed on the bed with her, I moved on top of her, holding myself up off her.

Eventually, I moved to lay next to her, wanting better access to feel on her crotch, and as we kissed, I moved my hand down until I was feeling on her mound. Letting my finger dip down and press into her slit, creasing her panties, we looked at each other smiling.

Immediately going down, kissing her chest and tongue her erect little nipples, I move on top of her slightly. Not looking up, I kissed my way down her stomach, until I was nuzzling against her pussy. Wanting to eat it, I mouthed it through her panties and eventually pulled them to one side.

Seeing her fleshy little pink pussy and noticing she liked to keep it trimmed was such a turn on, I looked up at her. Ashley was resting on her elbows, watching and when I smiled cautiously she asked, “What are you doing? “

She had a foxy little smile, and as I got on my knees, I smiled and immediately started pulling them down. Ashley immediately lifted her ass off the bed and as I got them over her feet, I threw them off the edge of the bed.

She nervously kept her legs bent and together, but as we looked at each other I subtly spread them apart. She only had a small patch of hair in the shape of a triangle and seeing her little labia pushed out, I couldn’t help but smile.

I wanted to eat her pussy and after shifting back a little, I leaned up to kiss her. Ashley closed her eyes as we kissed and when I moved my hand to touch her warm little pussy, she gasped and opened her eyes. Smiling, I moved down and as I lay between her legs, I pressed my cock against her pussy. Ashley now brought her knees up, and when I reached up and spread her pussy lips with my one hand, she laid back.

Immediately going down, I slipped my tongue in her slit, and started tonguing her clit. She squirmed a little and after another gasp, she reached down, touching my head. I couldn’t stop, and as I pushed my tongue into her, I looped my arms around her legs, pulling her closer.

As I tried to fuck her with my tongue, she reached down, taking hold of my head. Ashley now tried to get me to come up, and when she softly said in an out of breath voice, “Stop,” I knew she was close. Not stopping, thinking I might be able to get her off, I reached up to steady her by putting my hand on her stomach.

Continuing to tease her clit as I vigorously licked at her pussy trying to get her to cum, Ashley started to squeeze my head between her legs. It kind of hurt, but I wasn’t going to stop, and this time when she actually tried to pull me up, I looked up at her. Wiping my mouth, I moved back up on top of her and immediately took hold of my cock, trying to push into her.

In an out of breath voice Ashley said, “No, don’t,” which made me again look up.

I could tell she had cum and seeing she was still reeling, I desperately wanted to be in her. Pushing into her I could see it was going to happen, but suddenly I felt I needed to be a gentleman. Stopping I said, “Maybe we should use a condom.”

I had one in the pocket of my pants, and as I struggled, reaching for then as they lay on the floor, Ashley not thinking said, “it’s okay, I’m on the pill.”

I think she was caught up in the moment and maybe a little drunk, in either case as I came back up, and lay there on my back, I asked, “Are you sure?”

Ashley now looked down and seeing how hard I was and realizing that she might have made a mistake in judgement, there was a pause. Smiling as she looked back up at me, I leaned up and kissed her. She was obviously trying to hide her apprehension and not wanting to let on, I think she felt she had to trust me.

Looking up at me smiling, we kissed as she reached down and took hold of my cock briefly. I was rock hard and as she move to kneel along side me, she started stroking my cock. Ashley seemed to be focused on giving me a handjob and as she looked up at me smiling, I again leaned up so we could kiss.

Ashley let go as we hugged and kissed, and then as I laid there and we looked at each other, my hard cock started to jump a little in anticipation. I couldn’t stop it, and when I happened to embarrassingly look down, Ashley look down too. Smiling, she reached for my cock again, and after giving it a gentle squeeze, she again started rubbing it.

It felt good and when I leaned up grabbing her by the waist, I pulled her to climb on top of me. Smiling and shifting a little as she looked at me, she eventually swung her leg over me and as she straddled my waist, I gently held her hips. Ashley then leaned forward to kiss me and after giving her a hug, she sat back up.

I think she wanted to do it as much as I did because she now reached back and took hold of my cock, giving it another gentle squeeze, wanting to feel how hard I was. Smiling as she looked at me, she scooted back a little, an immediately tried to guide it in her. I could feel the head of my cock pressing into her wet little slit, and seeing she had her eyes closed, I pushed her back a little more.

As she continued to guide the head of my cock into her, Ashley slowly started rocking back and forth, letting it go in. She was tight and as I held her waist, Ashley arched her back slightly, letting my cock slip all the way in. Instinctively, I now reached up to feel on her tiny little tits and as I did, she leaned forward and smiled.

Ashley now slowly started bobbing up and down and when she happened to lean forward to kiss me, I said, “It feels so good in you.”

She smiled and after a kiss, Ashley slowly let my cock slide in and out of her. It really felt good to be in her and as she continued to carefully move her ass up and down, not wanting my cock to slip out, I moved my hand down to her waist.

Eventually, I pulled her forward and kissing her, I slid my hands to feel on her plump little ass. Continuing to guide her to move a little faster, I wanted to cum. I was going in and out of her a little faster, but whenever she happened to lean forward, my cock would inadvertently slip out. Of course, I would hastily put it back in, but after a couple times of this happening, I eventually rolled us over so she was on the bottom.

Immediately getting between her legs, I quickly grabbed my cock and hastily put it back in. I think it must have hurt a little because she did squirm and push on me as she asked, “Go slow.”

Even though she was wet, she was still really tight. Kissing her, I carefully tried to push deeper into her, but I eventually had to force it in a little. Slowly moving my cock in and out of her now, she put her hands on my sides.

Hunching over her and hooking my hands under her shoulders, I kissed her on the cheek and as I tried to fucked her, I didn’t want her to stop me. I wanted it to last, but it didn’t take long before I was close. Again, not wanting to cum to soon, I stopped and as we looked at each other, Ashley asked, “Are you okay?”

I was definitely okay and after a subtle kiss, I slowly started bucking my hips into her. She was really wet now and I so wanted to cum, and then as she wrapped her arms around my neck Ashley said, “I want you to cum.”

She now moved both her hands to my ass and kept pushing me to go deep into her. I tried to concentrate, wanting to cum and as I kissed her, I scooted up.

“Oh yea,” I thought as I got close, and then telling her, “I’m going to cum,” I pushed deep into her and held her close.

She tried to keep me moving but as I tried to hold her still, I asked her in an out of breath voice to stop. My cock was jerking and pulsating, pumping cum deep inside her, and when I instinctively started to slowly move my cock in and out again, Ashley wrapped her arms around my neck.

I’m sure she could feel it now, because as I started to fuck her again, I could feel cum had started to seep out, and it was so slippery, I had to make sure my cock didn’t accidentally slip out.

I was done, and when I stopped and kissed her cheek as I held her she asked, “Did you cum?”

Smiling to myself, I lifted off her a little and then smiling I chuckled and said, “Oh yea,” and then leaned forward to kiss her.

Looking at each other for a moment, not saying anything, Ashley smiled and then suddenly said, “I’ve never been with a guy so much older.”

I didn’t know what to say, but seeing her continuing to smile, I gave her a hug. I knew she was just poking fun at my age, but when she hugged me back and said, “That was great,” I knew she meant it.

Kissing her again on the side of her head, I could feel my cock going limp and so I reached down, squeezed the last little bit of cum out into her and gradually moved down, letting it slip out. Kissing her chest now, Ashley put her hands on my head and when I glanced up at her I asked, “Are you okay?”

I could see she was a little flushed, but was beaming as she nodded, which made me move back up to kiss her. I had cum a lot and feeling it dribbling out of me a little, I knew cum had probably leaked out of her too.

Rolling off her, and laying on my side next to her, I watched as Ashley reached down to her pussy. It was obvious she could feel cum seeping out, and then after bringing her hand up to look at her fingers, and seeing they were covered in sticky cum, she looked at me. Trying to smile as we looked at each other, Ashley suddenly looked down again. She eventually caught herself, and then looking back up at me, she smiled sheepishly and said, “I’ll be right back.”

Ashley slid off the bed and as she scurried into the bathroom with her hands over her pussy, I couldn’t help but watch her plump little ass shake, which made me smile as I watched her close the door. I knew I had cum a lot and she seemed to stay in there for awhile, and when she didn’t come back right away, I started to worry. However, it really wasn’t very long before I heard the toilet flush and then as the door open, I nervously leaned on my one elbow.

As she came back, I tried to put on my best smile and as she got close I scooted over so she could get back in bed. I again asked her if everything was okay. She had a concerned look but said, “Yea, I’m okay.”

It was obvious something was weighing on her as we laid together, but what was it? Holding each other, I felt maybe she was looking for validation and when I leaned away and then gave her a kiss I said, “That really was great.”

It made her smile and then as she hugged me tight, we kissed and she said, “Yea, it was.”

I knew she was worried and felt that maybe she need some space, and being it was getting late, i felt I should probably get going. We continued to lay together with our legs tangled but we didn’t say anything and when I subtly said, “Maybe I should go,” Ashley asked, “Really?”

I tried to tell her I needed to go and yea, Ashley did try to get me to stay. I didn’t want her to feel it was a one night stand, but I didn’t want her to regret what we had done when we woke up together in the morning.

Eventually, I did leave and as I headed home all I could think about was her. I wanted to be with her again and every time we would see each other at Starbucks, I think about asking her out again, but because I knew she had a boyfriend I never pursued it.

We still talk and flirt with each other, and I do think she’d be open to going out again, but as of now, neither of us have made a move, but it’s always on my mind when we see each other.

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