The Barista and The Business Man(Mf, Extreme Age Gap, anal, fisting)

This I wrote not too long ago. I’ve been on a much younger woman older guy mood lately. This is by no means a true story but there are some things that are true peppered in there.

When I was eighteen I worked part time in a coffee shop located in a hotel. Lots of business people would come through. if there was a convention, some people would be out there for a whole week sometimes.

I have a dirty mind and sometimes would wonder how some people would be in bed. I wouldn’t dwell on it but it would be a fleeting thought. I enjoyed flirting with customers and getting some people’s day off with a bit of an ego boost.

I usually dated guys around my own age but had fucked quite a few older men. With older men it was usually about the sex. I loved being their little fuck toys and of course they treated me like I was a sex goddess.

I used to think men in their thirties and forties were at their best especially when they were hot however an affair I had with a fifty nine year old man the summer before I went away to college changed my perspective.

Older men in their 50’s and even into their 60’s became a bit of a fetish of mine. I loved watching porn, still do, with much older men and younger women. In time I didn’t care if the old man was attractive or not. Whether he was in shape or overwheight didn’t come to matter as well. The mere thought of being a young, hot woman being used by someone who could be my father or even grandfather got my pussy wet. Also I came to learn looks had nothing to do with how nice a cock a man had or how good his skills were in the bedroom.

Some of these business people would be in for a week if they were at a convention. As the week went on, I would sometimes get into conversations with customers and get to know them better. Nothing too deep but little small connections you make with people.

I’ve always been big chested. At eighteen I was a full C cup though I was only one hundred and fifteen pounds at five foot two. My full brown hair was long that went to my waist though I had to wear it up at work.

At the beginning of my freshman year I started dating a guy, Tom, in my class. I thought we were getting serious but then I caught him making out with another girl at a party. That was a Saturday night. I spent my Sunday crying over it.

“He doesn’t deserve you,” Ashley my good friend said. “You are way hotter than him anyway.”

“Thanks. It sucks because I thought he was a nice guy,” I said.

“You know what you need to do?” Ashley held my hand to comfort me.

“No.”

“Go out and find someone to fuck your brains out. It’s easy to get over someone when you’re under someone else.”

I laughed at her but she made me feel better. Tom wasn’t exactly my best lover anyway. Not bad. Not great. Average.

Ashley talked about a frat party we could go to the next weekend. “There definitely will be a hot guy down to fuck at the party. All you will have to do is ask.”

I appreciated my friend trying to help me get laid to mend my broken heart but I wasn’t interested in fucking some dumb frat guy.

Later that night I fantasized about seducing one of the bussiness men that come through the coffee shop. I had a shift at the coffee shop on Monday morning and there was a convention being held that week. I thought about how hot it would be to make some older man’s week while he was away from home.

My hand found my pussy and I rubbed my clit fantasizing about how old of a man I could seduce. I had to be quiet as I was in my dorm and my roommate slept in the next bed. Despite that I made myself cum three times thinking of men who could possibly be my father or even grandfather’s age. The older the better because at that time I was fed up with guys my age.

The next morning I was excited to go to work hoping I would be bold enough to hit on a customer. It was busy the first few hours as it usually was. A few older gentlemen caught my eye but other than brief harmless flirting I didn’t have much time to strike up a proper conversation. Then I thought maybe I should write my number down and hand them the piece of paper when I handed them their coffee.

As the morning rush died down and I only had 10 minutes left of my shift, I was dissapointed I wasn’t brave enough to set up a fuck date.

As I was thinking I was silly to think I would hit on a customer, a man with piercing blue eyes walked in. Those eyes were the first thing I noticed then I noticed the whole man.

I guessed him to be in his late fifties. Possibly sixty. He was at about five foot eleven and he wasn’t fat but had some weight on him. His arms looked strong though. Looking down, I noticed his hands were rather large. For a brief moment the thought of those hands cupping my breasts flashed through my mind. Also I wondered if large hands indicated if other things on his body were large. There also was a wedding ring on his finger but that only made him more attractive

He had a full head of grey hair and a neatly trimmed beard. My dirty mind couldn’t help but wonder what that would feel like if he went down on me.

“Large coffee, black,” the man asked.

I smiled brightly at him and gave him the total. I wondered in the few seconds he was in and I sized him up if he was doing the same to me. Was he having fleeting dirty thoughts about me, thought I was a cute girl or saw me as just another generic customer service person and was only thinking of his plans for the day?

For a second, I thought his eyes looked down to my body but that could have been my wishful thinking.

“Have a nice day,” I told the stranger and felt dissapointment as he walked away.

My coworker came over to take over the cash register from me.

“I’ll be right back,” I said and tried not to seem too eager as I walked out of the coffee shop to see if I could catch the man.

Luckily he was still in the lobby of the hotel.

“Sir, excuse me, sir” I called for him and he turned around.

“Yes?”

Suddenly I felt a little panic and my mind went blank for a second. Somehow my mouth found words to speak. “Hi, I’m Sandy.”

“Hi, Sandy,” the man smiled and looked at me like I had two heads.

“I apologize for being forward or if I’m bothering you but I found out my boyfriend was cheating on me and my friend said I need to get under someone to get over him. I’ve been with older guys before and I think older guys are hot. You caught my eye and I was wondering if you wanted to fuck me. Have a fun little affair while you are away from home.”

For a moment the man was speechless and suddenly I felt mortified.

“I’m sorry to bother you, sir,” I said and was ready to run away and die from embarasment.

“Are you serious?”

“Yes, I am.”

The man laughed only a bit, “How old are you?”

“Eighteen.”

“Shit. And you want an old man like me to fuck you?”

“Yes. I want you to fuck me,” I again felt my earlier confidence coming back since he hadn’t told me off. He seemed like he was open to my proposition but was in shock.

“Holy fuck,” the man was now the one trying to find words to speak, “Ok. Well I’m in room 1435. You can show up at ten.”

I smiled and I was definitely turned on wishing he would take me up to his room at that very second. “oh ok great. It’s a date.”

He flashed a devilish smile at me, “It’s a date.”

“See you then,” I turned around still smiling. Looking back, the man was still watching me.

I was excited but then it just occurred to me I didn’t get his name. It made me feel very slutty that I setup to fuck someone without getting their name. That fact only served to make me even hornier about the whole situation.

When I got back to my dorm, my roommate wasn’t in. My hand instnantly found it’s way to my pussy and I came hard imagining it was the stranger making me cum.

The day couldn’t move fast enough. I had two classes that day and I tried my best to concentrate. My thoughts kept going back to my date. Hopefully it would live up to the fantasy in my mind.

Later that night, I wondered what I should wear. I debated if I should show up in an outfit that made me look like a slut or something more understated.

I decided on wearing a sundress. Nothing too scandalous but I liked how it hugged my curves. It was a bit low cut and showed off my cleavage. I figured I wouldn’t be wearing it for long. Usually I would wear a bra, but I decided to skip on it as well as any underwear. My nipples were hard and the thin material of the dress didn’t hide them.

My pussy was so wet as I reached the hotel and made my way up the elevator to his room. The excitement of doing something so naughty fueled my desire.

Taking a deep breath, I knock on his door. He opened the door and his eyes looked over my body.

“Hi,” he said as I stepped in the door. “You look amazing.”

“Thanks,” I could feel myself blush.

“I wasn’t sure if I was having a prank played on me this morning,” he stepped closer to me and carressed my cheek. “I feel like I won the lottery. You are so damn sexy.”

He leaned down and we started kissing passionately. His hands roamed my body. As he grabbed my ass and pulled me closer, I could feel his erection pressing into me.

Pulling away from him, I gave him a naughty look as I took my dress off. It didn’t take long before he was on me. We made our way to the bed where I sat down and he was on his knees in front of me kissing my neck and then going down to worship my breasts.

I laid back on the bed as he spread my legs apart. “Your pussy always shaved like this?”

“I get a wax regularly,” I said panting. I gasped as he started to eat me out.

His tongue explored my pussy as I laid open to him. I couldn’t stifle my moans.

Lifting my ass a little, his tongue went down to explore my tight asshole which I loved.

“I love my asshole being played with.”

After a few minutes he looked up at me, “Your ass and pussy tastes so good.” He then put two fingers in my pussy while his thumb rubbed my clit. “So fucking wet.”

By this time I was a bit lost in all the sensation and was close to coming. When he took his two fingers out of me and put one wet finger in my ass as he went to suck on my clit, I completely lost it and came hard.

He came up to me when my body settled down and we started making out. My pussy juices were all over his face and I enjoyed tasting myself on him. I had wrapped my legs around him wanting this stranger closer to me but he was way too dressed.

We paused our make out session and we stared at each other with satisfied grins.

“I want you naked,” I said and my nameless lover stood up and started to undress.

As he got undressed, I played with my pussy. He watched me while I watched him. His body turned me on. It wasn’t conventionally attractive but I liked the hair on his chest and body. He was only a bit pudgey but looked strong underneath. To me he looked very manly.

“I still think I’m going to wake up from a dream,” he said as he took his pants off.

His cock did not dissapoint. It was bigger than average in length and girth but not something that would be too much to handle.

“I’m real and you really turn me on,” I spread my legs wide so he could watch me touching myself.

“Are you going to cum for me again? Play with that sweet pussy. You looked so innocent this morning. I thought you were some shy college girl with a nice rack. But you’re an insatiable slut.”

Faster I moved my hand on my pussy. I stuck three fingers in me and moved them so that he could hear how wet my pussy was for him before moving to rub my clit.

“I want to be your slut. My pussy is so wet for you,” I was seeing stars as my orgasm over took me.

The stranger walked over and grabbed the back of my head and I didn’t need any more encouragement to take care of his cock.

I licked up and down his shaft. down to his balls and up again. My tongue lapped up the precum at the tip of his cock. I loved the taste of his cock and from his reaction he loved how I was servicing him.

I mused if he gets his cock sucked regularly or if he only gets it on birthdays and anniversaries.

“I want to come in that pussy,” he said as he forced me off his cock.

Pushing me flat on the bed, he positoned himself between my legs. He pleasured me spectacularly earlier so I didn’t mind that he was fucking me with only his pleasure in mind. Him using me turned me on as he thrusted fast into me.

“Use my teenage pussy. I want all your cum. Fill me up,” I said not so quietly. When he came, he wasn’t quiet either. He had a lot of pent up cum that spilled into me.

I kissed his neck and carassed his back as he was finishing. He didn’t pull out right away sharing a passionate kiss before he did. Feeling his cum in me, dripping out of me kept me in a state of arousal.

Usually I would have the guy wear a condom especially since I’d been away at college. Even Tom wasn’t allowed to fuck me without one but I was so caught up in the fantasy it didn’t occur to me to bring one. No regrets though.

We laid in each others arms and started to actually talk. He asked what I was studying in school. I asked what he did for work. Then he told me about his family. He had three children. His youngest was ten years older than me. He already had three grandkids. His wife and he had been married for thirty six years.

“It’s been eight years since I got my dick sucked. Eleven years since my wife let me eat her pussy and six years since we had sex,” he kissed my forhead, “I thought I was never going to have sex again.”

“Oh that’s awful,” I gave him a kiss, “I’m glad I could help you out.”

“You’re fucking amazing. Lately I’ve been thinking about having an affair. Going on websites but I don’t know if I would have actually gone through with it.”

My hand found it’s way to his cock again hoping to stir him up again. His cock was brought back to life and was rock hard for me again.

Straddling my new lover, I lowered myself onto his cock. Slowly, I went up and down his shaft. His hands were on my breasts, pinching my nipples. He leaned up to take one in his mouth.

“I still don’t know your name,” my voice was breathy.

“Shit. It’s James.”

“Nice to meet you, James,” I said as I rode him faster. “how old are you?”

“Sixty,” he moved his hips up to meet mine.

“James, fuck my teen pussy. I love being fucked by an older man like you.”

James flipped us around and forced me to flip over so he could fuck me from behind. His powerful arms held me up so I was up and my back was up against him. His right hand held me at my throat while another explored my breasts.

“You’re my little slut. I’m going to use you all week. Your going to take all my cum, baby.” Faster and faster he rammed into me.

The hand at my breasts moved lower to play with my clit. Once again I came hard on his dick and James spilled into me.

Afterwards we took a shower and fell asleep in each other’s arms.

For that whole week I basically lived at James’ hotel room. I packed a bag and James gave me a second key to come and go as I please for class and work. At night I would be waiting naked for him when he was done with his obligations and networking.

On Thursday that week I didn’t have class so in the afternoon James met me at the hotel room to get a quick fuck in.

Ashley asked me why I wasn’t around to hang out as much and I told her I took her advice about getting under someone.

“What? That’s fucking great,” she said excited for me, “who is he.”

“No one you know. He’s older,” I said trying to be vague.

“Like twenty five?”

“Not exactly.”

“Oh like thirty? Ooh older men are hot. I was with a twenty eight year old once,” my friend bragged.

“Yeah something like that.”

All week we explored our bodies. James said he felt like a teenager again. He was able to come a few times a night. Usually he loved coming inside me but a few times he came on my ass, tits and face.

It was like he was trying to get all he ever wanted to do but his wife would never let him do with me.

One night he had me splayed on the bed fingering me. He slapped my pussy making me whimper.

“I’m going to make this pussy take my fist, slut,” he said as he stuck three fingers in me. “This pussy is so wet I don’t need lube.”

The thought of his fist inside me excited and terrified me a bit. I never had been fisted and his hands were big.

He was becoming an expert of my pussy in that week. James knew where all the right places were to turn me on. He took his time working his hand on my pussy.

All the while I was moaning incoherently being consumed with pleasure.

“Holy fuck. Sandy, you are a squirter,” James sounded proud as my body convulsed and my pussy leaked. “I have four fingers in. You’re doing great. This tight teen cunt is being stretched out.”

“Please,” I said not knowing what I exactly was asking for.

He used his other hand not inside me to play with my clit. Keeping me in a constant state of coming and almost coming.

My biggest orgasm yet finally happened

“Oh good girl. My fist is in you, baby, I feel your pussy reacting to me. So fucking sexy.”

I was lost in the fullness and sensations of it all. The only thing I could do was let James do what he wanted with my young pussy.

Eventually he removed his hand from inside me. He moved to straddle my chest and stroke his cock.

“You are such a dirty whore. You deserve to be covered in my cum.” Faster and faster he stroke his cock until he came all over my face as I laid there exhausted and spent.

A few minutes later he carried me into the shower. The shower was rather big and had a seat in it. James sat me down and washed me.

The dichotomy of him using me so harshly earlier and then being so tender caused raw emotions in me to fester. I started crying and had no idea why.

“Are you ok?” James voice was full of worry, “I went too far didn’t I?”

I shook my head, “Sorry I don’t know why I’m crying. I’m going to miss you when you have to go home.”

He kissed me sweetly, “I’m going to miss you too.”

The next night as he was pounding my pussy I looked back at him and begged him to stick his dick in my ass. Pulling out of my pussy, his cock was wet enough to go right into my ass. However he did start out slow.

“James, don’t hold back. Fuck my ass,” I pleaded.

The man didn’t need any further encouragement as he started fucking my ass without abandon.

“You’re ass is so tight. Feels so fucking good.”

“Fuck. I love it. Use my teen ass.”

As he pounded into me, I moaned out my pleasure. He came so much when he spilled into me. James held me tight for a bit before we took a shower.

The day finally came when he had to leave and I felt rather sad about it. I know he did too. We hugged and kissed with a lot of need. I gave him one last blow job before he left.

We exchanged numbers and emails. We would still communicate. Sometimes I would send him naughty pictures and a couple times I sent him videos of me masturbating. One time I sent him a video of me being fucked by another older guy.

He eventually got a girlfriend that was in her forties. I was happy he didn’t have to give up his sex life. One time he did have to be in my area for business and we met up and fucked. Another time his wife was visiting his sister on a weekend and he flew me out to see him. I even met his new mistress but that’s another story.

Our communications wouldn’t always be sexual and would be general updates on each other’s lives. Then eventually our commumications became less and less. Not sure when it died down but both our lives moved on and got too busy to check in on each other. James will always be a great memory though.

Source: reddit.com/r/eroticliterature/comments/uic6hd/the_barista_and_the_business_manmf_extreme_age