Better with Age Ch. 01

Story Info
Chance meeting with older woman on subway changes his view.
3.9k words
4.53
118.4k
31

Part 1 of the 3 part series

Updated 09/27/2022
Created 08/01/2009
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
goes4grey
goes4grey
24 Followers

When my buddy Jim called to invite me to the Mets/Yankees game at Shea I jumped at the chance. I pretty much had been wallowing in depression since my recent divorce and getting out to a game was just what the doctor ordered.

I hooked up with him Saturday in Times Square and we hit a good watering hole before hopping the 7 train out to Queens. The subway car was already pretty packed when we got on at 42nd Street but when it pulled into the next stop another 50 people crammed in and everyone was sandwiched up against each other. The woman that was next to me when we first got on was now pretty much up my ass. She was grey haired and tall, about 6 inches taller than my own 5'-8". She had a nice face, not pretty, not ugly, just nice. If I had to guess she was about 50, some 15 years older than my own 35. But what really got my attention were her huge breasts because they were now pressed up against my arm and back.

She apologized for mugging me with a smile. As the train rocked along towards Queens her big tits bounced and rubbed up against me and I distinctly felt her nipples harden against the bare skin of my arm. Whenever I looked back at her she just smiled.

Jim, the social butterfly that he is, struck up a conversation with her. He is a huge Yankee fan and he started giving her a good natured ribbing about the Mets, which she was a fan of judging by the T-shirt she wore. She told us her name was Jean and that she was a lawyer and worked in Manhattan. She was originally from Ohio, but came to New York for college and never left. I told her I was originally from Maine and came to New York the same way, via college. I'm a project manager for a small woodworking firm in the Bronx and told her I've done a bunch of projects for various law firms. I hadn't heard of her firm however, they sounded like a small time outfit.

The whole time we talked her tits were plastered up against my back, it was hot as hell in the subway car and our shirts were starting to soak thru with sweat and I could feel her nipples get even harder as they rubbed up and down my arm. Thankfully she couldn't see the hardon that was growing in my shorts.

Finally the train reached Shea and we disembarked and like cattle moved towards the entrance. When we got out in open air I noticed that Jean was still by my side. She said she was meeting a friend at Gate 4 and asked if we could show her where to go. Jim gave her directions. I don't know what came over me but all of a sudden I was handing her my business card and telling her if she needed any woodwork for her office to give me a call I would hook her up. She thanked me, smiled and then disappeared in the crowd.

The game went into extra innings and the Mets ended up winning with a walk off homer. Jim was all pissed off and we were both pretty lit from drinking beer in the hot sun all day. We took the train back into the city, but didn't see Jean this time. We ended up grabbing some chow at a pub in the village and Jim called this chick he had been banging recently to come meet us. He asked her to bring a friend for me but she showed up alone. While we drank she was all over him, hands in his pants and practically fucking him in the booth. I eventually got tired of being the third wheel and called a cab and went back to my apartment in New Jersey feeling lonely and horny. I crawled into bed and jacked myself off, the whole time thinking of the old broad on the subway train rubbing her tits all over me. I drifted off to sleep and her image slipped from my mind not to appear again until 2 weeks later.

It was a Friday afternoon, the end of a long day at the end of a long week. I was out at a jobsite measuring up some rooms for cabinets when my cell rang. "Hello" I answered somewhat irritably.

"Hi is this Mike Dupree?" a woman asked.

"Yes this is Mike, whose calling?"

"Jean Merryweather" Jean, Jean who the fuck is Jean my mind is searching

"You don't remember me do you; we met on the subway going to the Mets game a few weeks ago"

"Oh that Jean, I'm sorry I didn't know your last name it kind of threw me"

"That's OK, I guess I am calling out of the blue. You said you would "hook me up" with some woodwork for my office, I was calling to take you up on your offer."

"Sure, sure, I guess I did make that offer. Why not, where are you located? I'm in the city now and can swing by"

"I'm on 7th Ave between 28th & 29th, number 356 fifteenth floor."

"Alright, I can be there in about an hour, is that OK?"

"That would be perfect, see you then"

I hung up and returned to my work. My thoughts strayed to those big tits rubbing up against me on the subway and I wondered if Ms Merryweather really wanted some woodwork, or was she looking for some wood. Either way, I was looking forward to seeing her again.

An hour later I was sitting in the reception area waiting for Jean to come greet me. The receptionist, a chubby but pretty girl named Gretchen, apologized for the 5th time. "I'm sorry Mr. Dupree, Ms Merryweather is still on a conference call, it won't be much longer I promise" I was starting to get agitated as I had been there for 15 minutes already, it was late Friday afternoon and I wanted to get home and start drinking my blues away.

Finally a door opened down the corridor and Jean Merryweather was walking towards me. She looked much different than I remembered her. She was wearing a white pleated long sleeve blouse buttoned all the way up to her neck her chest pushed out tight against it, a burgundy hip hugging skirt that came down to mid calf with buttons up the front. Her grey hair was tied up in a bun and she was wearing glasses. Librarian was the first thing to come to my mind.

"Mr. Dupree, sorry for the wait, my client can go on and on sometimes. Let's take a look at my office shall we? Gretchen I should be about a half hour, you have a nice weekend if I don't see you before you leave." I followed her down the hall, her wide hips swaying back and forth in front of me. She stood in the doorway to her office and I had to turn sideways to go in and her breasts rubbed my shoulders as I passed. She closed the door and I'm not sure but I think she locked it, I was kind of thrown off by the tit rub.

Her office was about 15 ft x 10 ft with a large cherry desk by a big window that looked out at 7th Avenue. There was a couch on one fabric covered wall and a credenza on the opposite wall and a small conference table in the corner by the couch. The floors were wood and there was an area rug in the center under the desk. "Very nice" I offered.

"Thank you, but it is getting rather dull, I think I need a change. Perhaps you can help me with that"

"Well some wall paneling on the front wall would certainly give you a new look, let me sketch something out for you"

I put my work bag down on the conference table and pulled out my tape measure and a pad and pencil. I measured the length and height of the wall and started to sketch it out on the pad. Jean came up behind me to look at what I was drawing. She stood close enough that once again her big breasts were rubbing up my arm. This woman likes to have her tits rubbed I was thinking. I finished the sketch and explained it to her while she stayed pressed against me. "I think this is perfect, just what I need to spruce the place up. Let's do it" I couldn't help but think that she wasn't referring to the paneling when she said that.

"Can I get you something to drink Mr. Dupree?"

"Sure, I'd love a beer but I'll take a soda if that's all you got"

She gave me a disapproving look over her glasses as she went over to the credenza and opened up a refrigerated drawer. "Ginger Ale is the strongest I have, will that do?"

"Fine with me, thank you"

She crossed the room with 2 cans of soda and sat down on the end of the couch. "Make yourself comfortable Mr. Dupree" she said as she patted the cushion next to her. I came over and took the can she offered up and sat on the opposite end of the couch, not sure of what was going on to sit closer. She smiled at me, just the way she had that day on the subway. I chanced a look at her chest and saw that her nipples had hardened since I last looked when I came in. She caught me looking and again gave me the smile. I figured what the hell, I'm going for this, what do I have to lose.

"So have you had sex in your office before?"

A stunned look on her face, "NO, MR. DUPREE, I HAVE NOT HAD SEX IN MY OFFICE BEFORE!" she reprimanded me. I guess I fucked this up, I thought. Then her look softened the smile came back and she said "does solo sex count?"

"No Jean, it does not count" I said as I slid over towards her on the couch. "But there is always a first time for everything" and then our lips met as my right hand went right to a big breast and squeezed it. She moaned and then her tongue was out and invading my mouth. She was frenching me like a long lost lover and I was kneading her tits thru her shirt. I wanted to see them in the flesh so I started to unbutton her blouse starting at her neck. After I undid the last button I pushed the shirt off her shoulders to expose her heavenly globes encased in a classy white lace bra. I pulled my tongue out of her mouth so I could gaze upon her breasts. They looked enormous to me and her cleavage was long and deep.

I bent to stick my tongue between her tits and lick the tops of them. She held my head in her hands and guided me around her tits till my mouth was at a nipple beneath the fabric. I licked and sucked at it making her bra all wet with my saliva. While I sucked at her hard nipple her hands went to her back and the bra fell away leaving me staring at her naked chest. Her tits were big and exhibited little sag, not bad for an old bird I thought. Her nipples were the diameter of nickels and stood out proudly from small pink areola. I grabbed them in both hands and started licking back and forth from nipple to nipple. Joan moaned her approval and I felt her hand on my thigh moving steadily towards my stiffening prick. I bit down lightly on a nipple while I twisted the other between my fingers. I got a squeeze of my cock in return, she obviously liked what I was doing to her mammaries.

While I continued to work on her tits I felt her tugging at my belt and trying to get my zipper down. Since I was bent over her, it was difficult for her to get this task accomplished so I figured I would help the old girl out. I reluctantly released her tits from my grasp, stood up and moved in front of her. Her hands reached out and one caressed my hardon thru my pants while the other deftly undid my button and pulled down my zipper. Once my pants were undone she pushed them down to my ankles and my cock slapped back against my belly. "Oh My" she said as she got her first look at my 8 inches. "The girls must love this Mr. Dupree" she said as she closed her hand around it and began to stroke me.

She then pushed my cock up towards my belly and began licking the shaft from top to bottom. At this point I was fully hard and pulsing and her tongue felt light and playful as it licked me all over. She let my cock down and ran her tongue all over the head. She then opened her mouth and slid me inside. She got about half my cock in her mouth when it hit her throat. Looking up into my eyes she pushed forward and the rest of my hardon disappeared into her mouth. It was my turn to mutter "Oh My".

Like most guys I love having my cock sucked, in my mind there is no such thing as a lousy blowjob (although my ex wife could come close the infrequent times she took me in her mouth). Clearly Ms. Jean Merryweather knew her way around a cock and I was getting some of the best head I've had in years, maybe ever. She wasn't just sucking me, she was making oral love to my cock.

She would deep throat me for a few seconds then back off and suck and lick my helmet. A few times she would slide her mouth along my length like a harmonica, then lick her way back to my head and engulf me once again. I'm usually very vocal during sex and I had to keep reminding myself that I was in an office and there were people outside the door, maybe even on the other side of the wall.

I came close to cumming twice and Jean sensing my state would go down on my balls and give them the same treatment she gave my cock. She kissed, licked and sucked on them, individually and together before returning to my shaft to continue her masterful sucking. The last time she did my nutsack she slid her hands behind me and started scratching her nails up and down my ass cheeks. She pulled my cheeks apart and started rubbing her finger around my anus. I took all my power not to shoot my load then.

Releasing my nuts with a plop she licked back up to the head of my cock. Again she looked me in the eye as she pulled me all the way into her mouth and simultaneously slipped her finger into my ass up to the knuckle. That was the end for me, my cock erupted in her throat and she gagged slightly then pulled off till just my head was in her mouth. She sucked hard on it as my cum flooded her mouth, me gritting my teeth and grunting the whole while. The last of my seed oozed out into Jean's cum filled mouth. She pulled my cock out and licked it up and down with a cum coated tongue then sucked it back into her mouth. She did this over and over again and my cock glistened in the light. Eventually I had to stop her, I was close to losing my footing my legs were so wobbly.

I pulled Jean to her feet and took her into my arms and kissed her hard. I could taste my sperm in her mouth. My hands moved down to cup her ass and I pulled her against my still hard dick. I wanted to return the oral favor she had just given me. I moved my hands around to the front of her skirt and started fumbling with the buttons, she giggled and said "They are fake buttons silly" and she moved my hand over to the side of her skirt where the zipper was concealed under a pleat. I pulled it down and she stepped out of it.

She had apparently bought her panties along with the bra as they matched, classy and lacey. I guess I was expecting granny panties so this was a pleasant discovery. I pushed my hand up against her mound, the material was soaking wet. She must have got off on sucking my cock almost as much as I did. I pulled the band aside and ran my fingers along her moist slit. "I've got to eat you" I said and pulled her over towards the conference table. I swept the sketches and everything off the table while she removed her panties and shoes.

She was now completely naked and I took in the sight of her hungrily. She was almost Amazon like with her height, wide hips and big tits. I pushed her back on the table while I kissed her open mouthed. I kissed my way down to her breasts and spent a few minutes slobbering all over them, I couldn't help myself. Reluctantly I left her great tits and kissed my way south. I pushed her back on the table and she scooted herself up so she was completely on top of it. I sat down in one of the chairs and she opened her legs wide. Apparently everything on this older woman was large as I was staring at the biggest cunt I have ever laid eyes on. She had big meaty lips topped off by a clit that looked like my pinky finger, maybe even bigger. Moisture gathered at the bottom by her entrance.

I bent forward and started kissing her thighs all over, moving closer to her cunt but not touching it yet. I blew gently on it up and down. "Please" she begged "eat me, please". How could I say no? I stuck my tongue out and ran it up her slit from the bottom to the top. I ran it over her clit and she shuddered. I licked back down then took her meaty lips between my own and sucked them into my mouth. I took her big lips in my fingers and pulled her cunt open wide. I stabbed my tongue hard into her wet hole and started a slow tongue fuck. Her hands were on my head and she moaned softly obviously still aware of where she was. I started to fuck her faster with my tongue and she was pulling on my head trying to drive it deeper up her hole. I managed to get my head free and I licked my way back up her pussy till I was at her clit. It stood out like a little cock from her folds and I quickly sucked it into my mouth. She whimpered and her hands left my head and she took her big tits in them and started pulling on her nipples. I took her clit out of my mouth and started lashing it with my tongue. Hard and fast my tongue hit her big clit from all angles.

She was starting to shake as her orgasm was almost upon her. I took her clit back into my mouth and lightly bit down on it. Her thighs clamped down on my head as her climax rocked her body. I knew she wanted to scream but she managed to cum somewhat quietly just as I had. I continued to suck her clit as she bucked beneath me, squeezing my head between her meaty thighs. Thankfully she began to relax a bit and I pulled my head out before she crushed me.

I stood up, my cock was raging hard and I had to fuck this wild older woman and fuck her hard. I moved forward and aimed my fuck stick at her opening and pushed my way in. She arched her back and cried out softly as my dick entered her completely. I started to slowly slide in and out of her big cunt. She was surprisingly tight and the friction felt good as I varied the angle of my thrusts. The table was wobbling as I picked up speed. I pulled my cock out of her pussy and she groaned, not liking it. "We might as well christen your desk too" I pulled her up and kissed her quickly before leading her over behind her desk.

I spread her legs wide then pushed her face down on the desk and entered her roughly. Her clit was at the right height of the desk edge and it banged against it with each thrust. I reached around and took her mammoth tits in my hands and held on tight as I pounded my cock mercilessly into her cunt. She began to cum again as I gave her a sound fucking. She was pushing back against me trying to get more cock into her as she shook from the force of her climax. I clenched my ass, slammed in all the way one more time and began filling her cunt with jizz. I was shaking from the force of my orgasm and each spurt of my cock sent sensations all over my body. My cum spent, I leaned forward and rested my weight on her back, still fondling her globes. I hadn't fucked like this in a long time and knew I could get addicted to this older woman very easily.

My cock softened and I finally pulled it out, cum ran down her thighs. I scooped it up with my fingers and brought them to her mouth where she greedily sucked them clean. It was then I realized we had been fucking in front of the window with the blinds wide open and anyone from across the avenue could have seen us, I mentioned this to her and she laughed and said "well then they got one hell of a show. I can't remember the last time I was fucked so soundly, thank you Mr. Dupree".

We eventually got ourselves cleaned up somewhat and got our clothes back on. Jean led me to her door, pulled me to her for one last lusty kiss, and then showed me out to the reception area. Gretchen was already gone; I guess we were longer than a half hour. There were still sounds of life from areas of the office so Jean made a show of thanking me for coming in and that she looked forward to seeing my proposal and some samples. I told her I would be more than happy to supply her with some wood any time, gave her a wink and walked out the door. Going down the elevator I realized my view point on older women had just been changed, they certainly do get better with age.

goes4grey
goes4grey
24 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
dispatcher59dispatcher59over 5 years ago
Great story

Jean is very attractive, tall and well built. Fifty is not so old-of course, at almost 60, that's a given, but there's still a lot of life left in a gal that age. Good for him for taking advantage of it.

The part about them being seen from across the street made me laugh. I went to high school on 16th St. One day during finals I had a test on the 4th floor of the building that faced out on the street. The other guys who were taking that test were already in the room, all clustered around one window, looking across the street. There was a couple in one of the apartments there, screwing right in their window. That was pretty hot.

BTW, cab to Jersey from Manhattan?? 1-How did he get a medallion cab to go to Jersey?? 2-Has he not heard of the PATH train?? OR NJ Transit?? A lot cheaper than a cab!!

spaceinvaderspaceinvaderalmost 6 years ago
Hot

Love the description of how big and loose her cunt is. On and older amazonian BBW that's perfect.

kalodinkalodinalmost 6 years ago
Guess I’m jaded.

This is so fucking predictable and derivative.

AnonymousAnonymousover 14 years ago
Well Done

A 50 something year old woman with huge breasts - it doesn't get any better.

AnonymousAnonymousover 14 years ago
What a lovely lawyer!

I simply can't wait until I get the pleasure of reading chapture 2.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Party with the Neighbor MILFs A teen joins his four mature women neighbors.in Mature
My Best Friend's Hot Mom Young stud bangs MILF in all 3 holes during hot summer day. in Mature
Neighborhood Milf Life long dream fulfilled when he has her.in Mature
Donna Fucks Son's Friend Bareback Donna teaches son's best friend a lesson in satisfying women.in Mature
Tommy's Neighbourhood Ch. 01 His friend's Mum breaks him in.in First Time
More Stories