[Fm] Closing in on 40, I impulsively decided to let go of my good girl ways…

It had been at least a year since my last relationship ended.

That must have been the only reason I didn’t shut him down from the start.

One long, depressing year of mourning, frustration, and a handful of bad dates. Working at the library didn’t exactly create a lot of opportunities to meet single men.

One year without sex. Even longer, really, considering the last few months with Peter had not been a time we were getting along.

That’s the only explanation. That, and maybe the fact that I’d had a few drinks.

It was a Thursday night. I was in a strange town sitting in a bar without a date. And I was being hit on by a guy who was barely half my age. I was about to turn 40. He couldn’t have been more than 23. Mathematically, he was young enough to be my son.

And, yet, I wasn’t doing a thing to discourage him.

It was the weekend of my intern’s wedding. Rachel had just finished her undergraduate degree the previous spring. She was in graduate school and working on her masters in library science. That’s how she’d come to work for me. We’d developed a pretty good relationship, despite our age difference. She told me that she thought of me as the “cool” aunt she’d never had–which surprised me. Nobody had ever considered me “cool” when I was her age. When she’d invited me to her wedding I felt flattered and obliged to attend, even though it was out of town and I had to drive down on my own. I’d come down that day to the quiet little beach town and the group of people who’d already arrived decided to get together in a bar near the hotel.

Robin was one of the groomsmen. He wasn’t the best looking of the bunch and not the most polished, but he was attractive–tall and lean with a fit body. He was a bit dorky in the way most young men are, even if they don’t realize it. But he was also apparently the most confident. Or maybe that was just because he’d drank the most. And because he happened to be the one sitting next to me at the bar as the crown thinned out and guests started heading back to the hotel.

Ninety percent of the time I would have just found the flirting cute, a bit silly, and would have politely sent him on his way. But it had been so long for me…and I was drinking…and out of town…at a wedding, which always seems to make a single person feel a little bit lonely.

I’ve always been a “good” girl. I was late to develop and a little plump growing up and in college. I was shy. I didn’t have many close friends. As a result, I turned to books. I went to a college that was predominantly female and got a degree that few men get. And then I went into a profession dominated by women. By the time I’d really come into my own–physically and mentally–I had already become the type of adult woman who prefers quiet evenings at home and long term relationships over playing the field. I always assumed one of those relationship would lead to marriage, but it hadn’t worked out that way for various reasons.

With long blond hair, a fit body, and curves for days, I knew I’d developed into the type of woman that could catch a man’s eye. But, I’ve always felt awkward in social situations and have never been particularly outgoing, so I never seem to hit it off with men.

But none of that seemed to matter to Robin. He’d started out conservatively. It was obvious that he was flirting, but he wasn’t being overt.

“I’ve always liked women older than me,” he said at one point. “They just seem more intelligent than women my age.” It sounded like a rehearsed line of bullshit, but I smiled politely.

But the more he drank, the more forward he became. And I’d catch him staring at my body.

I wasn’t dressed very provocatively–but it was less conservative than my usual style. I had on black heels and stockings with a black sundress covered in a very bright, floral pattern. It seemed appropriate for the beach. It had a full skirt that came past my knees and a V-neckline that couldn’t help but show off my chest.

That’s where I kept finding Robin’s eyes. On my tits. He’d start off looking me in the eyes when he was speaking, but eventually they’d drift down in the most obvious fashion.

Maybe it was the alcohol. Maybe it was being out of down. Or maybe I was just happy to have someone pay so much attention to me after such a long layoff. But I made a conscious decision to play along. To flirt back just a little. To see how he responded. It seemed it would be good for a laugh.

“You know, you’re very beautiful, Chellee,” he said. “How old are you?”

“A lady never answers that question,” I said. “Aren’t you old enough to know better?”

“How old do you think I am?” he asked.

I guessed correctly that he was 23.

“Almost 24, though. In a couple of months. Won’t you tell me how old you are?” He flashed a crooked smile. I wondered if that was something that had worked for him with girls his own age.

“How old do you think I am?” I asked.

“I don’t know. Thirty-three?”

I couldn’t honestly tell if he was trying to flatter me or he really thought I was that young. Maybe it was a little of both.

“Really? Is that what you really think?” I asked.

“Maybe 35. Max. Like a very young 35, though.”

I couldn’t help feeling good about that. I knew I looked a little younger than my age. And I was certainly in better shape than most of my peers. But I still liked the compliment.

“You’re really beautiful,” he said again. “And I like talking to you. You’re smart. And cool. You’re Rachel’s aunt, right? She said you were her ‘cool’ aunt.”

“I’m not actually her aunt,” I said. “She just says that. I’m her boss.”

“Oh,” he said. “Well I’m not really close with Rachel. I mean, I’m her friend, but I’m really more of the groom’s friend. So you work at the library?”

“Yes,” I responded.

“So you’re like the cool, sexy librarian?” he asked.

I laughed at that.

“Is that a line, Robin? It sound like a line. Are you hitting on me?” I said with a smile.

“No,” he said. “No. Well, I mean, maybe a little. But no. I was telling the truth. You’re really beautiful!”

“What do you find so beautiful about me?” I asked. I scooted just a little bit closer to him. The bar was really starting to empty out. Most of the people we knew had left. Robin had told his buddies he’d catch up to them later. But all that was waiting for me was a lonely hotel room.

“Everything,” he said. “I really like your beautiful blue eyes, though.”

“Those aren’t my eyes,” I said. Robin’s glance had once again drifted downward.

There was a look of embarrassment for a second about being caught ogling my tits. I could almost see the wheels turning in his head as he decided how to recover. And then, as if a switch flipped, he apparently decided to push his chips to the center of the table and go all in.

“Well, I like your tits, too. You’ve got great tits.”

I blushed a little bit. I couldn’t believe he was being so direct. I decided that maybe he’d had too much to drink and it was time to end the conversation.

“I’m not sure that’s the best way for you to talk to a lady,” I said. “I think we should call it a night. I’ll assume you just drank too much and didn’t mean to say that.”

I stood up off the stool and put money on the bar for my drink.

He jumped up and stood next to me.

“Hey, Chellee. Don’t be offended!” he said.

Then he looked down again and didn’t even attempt to hide it.

“But, damn, really. You have great tits. I meant it.”

“Good night, Robin,” I said.

He put a hand on my waist and gently pulled my closer to him. It wasn’t intentional, but I brushed my thigh against his crotch. He was rock hard. I could feel it. And it excited me just a bit. He put his lips near my ear.

“Come on,” he said. “When is the last time you’ve been fucked hard and long by a guy ten years younger than you?”

The answer to his question was “never.” I’d never been fucked by a guy much younger than me. And he was a lot more than 10 years younger, though he didn’t know it.

It had been SO long since I’d been fucked hard by anyone. Or fucked in any way. And I hadn’t fucked a boy his age since my college boyfriend–when I was even younger than Robin.

He pushed his crotch into my thigh. This time he was making a conscious effort for me to feel his hard prick.

“I’m hard from just looking at you,” he said. “I PROMISE we will have a good time.”

He was getting me wet. Against my better judgment, I could feel myself contemplating the possibility. He did have a sexy body. He took my hand and ran it over his prick, letting me feel him through his khakis. It was definitely a thick piece of meat. Boldly, he leaned in and kissed me. And I could just feel myself letting go to him.

“Let’s go back to my room for one more drink,” he whispered.

My mind was racing.

“What the hell am I doing?” I thought silently. “Why the hell not?” was my second thought. I was out of town. I’d likely never see him again. I knew nobody at the wedding except for Rachel. And what had being a “good girl” gotten me my entire life? I wasn’t miserable, but my life hadn’t exactly lived up to my best dreams. “I’m almost 40,” I thought. “Why not have fun? Just this once?” It would be harmless. An adventure. And a self-esteem boost.

“OK,” I said. “I’ll have one more drink with you. But not in your room.”

Robin nodded and started to sit back on his stool.

“Not here,” I said. “How about over there?” I pointed in the direction of a round booth in a dark corner of the bar. It would definitely be private and a bit more intimate.

Robin agreed and we went to the booth. He took a seat on one side. I entered in the other direction and moved all the way to the middle. I patted the bench next to me.

“Scoot over,” I said. “Get next to me.”

He moved closer, leaving a space between us. I responded by sliding closer to him until our thighs were touching. I could see the look of surprise on his face. He obviously wasn’t sure what to expect. I imagined that in his mind he’d never thought something might really happen.

I put a hand on his thigh and ran it up to his crotch. His hard cock was going down the right leg of his pants–the leg pressed firmly against my left one. I started to caress it softly through his khakis.

“Ohhhh…” he said. It was something between an exhale and a surprised moan of pleasure.

I slid my hand up and down, firmly pressing his cock into his own thigh. I could feel the heat through his pants.

“Mmmmm…” he moaned again. The slick, forward personality was all but gone. He’d regressed into a surprised boy.

A waitress came over to take our order. With my hand still on his cock–safely hidden beneath the table in the dark–I calmly ordered myself another glass of wine. While I was still conversing with the waitress I moved my hand around until I found his zipper. And then I gave it a slow tug downward. I felt so naughty! I had NEVER done anything comparable in my life!

“And for you, sir?” the girl asked.

“What? Huh?” Robin said as he glanced up. He was very obviously flustered. “I…um…I want….”

My hand was in his trousers and fishing around for his cock as he talked. I found it and gripped it tightly.

Robin stumbled through his drink order while I slowly, rhythmically tugged on his piece.

“Oh. OH. That feels so good…” Robin said when the waitress left.

“Shhhh! You’ll give us away. You don’t want it to end do you?” I asked.

“NO!!”

“Then be cool.”

He slumped back in the booth and tried his best to look nonchalant. I kept rubbing him off. I couldn’t believe my own behavior, but it was making me hot!

Robin’s breathing was getting heavy. He moved his hips, trying to force me to go faster, but I wanted it to last. I glanced across the room and saw the waitress picking up two drinks that looked like our order. As she turned to come back to us, I pulled Robin’s cock out through his zipper. I couldn’t help but to glance down. The table would hide anyone else’s view but mine. It really was a nice, thick tool.

Robin appeared to be in a state of shock. I squeezed my hand tight around the head and started tugging faster. As people walked by, I was aware they might be able to see my arm moving. But they couldn’t be sure of what was happening.

When the waitress got close I stopped pumping him. With my thumb, I rubbed the tip of his dick. I could feel little, sticky droplets of cum, and I smeared them around. Robin looked like he was in a stupor.

“Are you going to pay the lady?” I asked him.

“Oh…uh…yeah,” he said.

He fumbled for his wallet. I was still tickling his cock at the cum hole with the tip of my thumb. He pulled out a 20–way more than our drinks would cost even including a decent tip–and told her to just keep it. Obviously, he wanted her to get lost.

I picked up my drink with my free hand and took a sip. As soon as her back was turned, I went back to jacking him off forcefully.

“Drink your drink,” I said.

Robin picked it up and gulped the whole glass down–some sort of whiskey concoction.

Two girls walked by and one of them did a double-take. I was certain she knew what was happening. Or at least suspected it. And I didn’t care. For the first time in my life, I WANTED to be bad. I winked at her. Then leaned close to Robin.

“Do you like the way I’m touching you?”

He just nodded. Emphatically.

I looked around, and then casually opened the very top button on my sundress. My black bra was now exposed. I watched Robin’s eyes fall on to the deep chasm between my tits.

“You like them?” I asked Robin.

“Yesss…” he said.

I ran my hand up and down his shaft a few times. I grasped the head and started pulling as fast as I could. I squeezed it firmly and he groaned in response. At this point, anyone looking what have realized exactly what was happening.

“You like the way I’m tugging your cock, baby?” I whispered. It was phrase I’d never uttered in my life. Never thought I would say.

“Yes…” he said again. “Please don’t stop,” he almost whimpered.

“You want to cum?”

“YES!” he said.

I gave him such firm tugs that I thought he might cum out of the seat. Robin groaned and grunted. And then he exploded. I felt some of his hot cum running down my hand.

I didn’t stop until he was finished and gasping for air. I pulled my hand up to the table and looked at his jizz. I reached for my cocktail napkin. Then something else came to mind. Looking Robin dead in the eye and licked his seed off my fingers. Then wiped my lips with the napkin.

“Who the hell am I tonight?” I thought silently.

“Well, I hope you enjoyed the drink. I’m glad I stayed,” I said getting up.

“Wait. No. Wait,” Robin stammered. “Let me pay you back. Let me do something for you.”

My intention had been to just walk out. I didn’t want things to go any farther. But I could feel that my little black panties were soaked. Instead of settling my craving for sex, jacking Robin off in the back of the bar had just made me hungry for more. I wanted a release. I wanted to just rush back to the hotel and take a hot bath and get myself off. But I knew I could have more fun.

“Don’t be a prude,” I told myself.

“Why don’t you walk me back to the hotel?” I heard myself say out loud. “We’ll see what happens.”

We slipped out a side door from the bar into a tiny alley between buildings. The boardwalk was out front. Beyond that was the beach. Robin was still dazed, but it looked like he was slowly regaining some of his swagger. We’d only walked a few steps when he firmly pushed me against the brick wall.

Robin went straight for my tits. He buried his face in them. And then he rubbed one roughly when he kissed me. He was sort of clumsy. A bit inexperienced. But I still liked it.

I glanced around. There was a large dumpster 50 feet up the alley before the boardwalk. I knew it was hiding us from the view of anyone passing by. But if anyone else left the bar by the side door they’d stumble right on us.

It didn’t seem that Robin had any concern about location. He pushed the skirt of my dress between my lefts and started rubbing my pussy.

“I want to taste you!” he said.

“Right here?”

“After what you did inside?” he said. “Yes. Right here.”

He grabbed the hem of my skirt and lifted it all the way up. There wasn’t much finesse to his style, like I’d become used to with older men. His hand went right to the crotch of my panties and pushed it aside. He didn’t bother with the clit. He just slammed two fingers up into me.

I whimpered a little bit with delight. He wasn’t delicate in any way. He just started pounding me with those two fingers. The sound of his palm slamming into my flesh filled the alley. I tried to stifle my cries, but every once in a while one would slip and echo off the brick walls. I was ready to cum when he suddenly stopped.

Robin dropped to his knees in the dirty alley. He put his torso beneath my skirt. I felt him pulling my panties down to mid-thigh. And then I felt his tongue.

He may have been an awkward kisser, but the boy knew exactly what he was doing when it came to eating pussy. I felt myself go weak in the knees. He clenched my ass cheeks firmly with each hand, pulling me closer to him. He was like a rattle snake, flicking his tongue rapidly over my clit. He brought a hand back around and started fingering me again. I put my hands on my own tits. I could feel my hard nipples. I tossed my head back and closed my eyes. I moaned loudly. And then I just let out a cry. And then another. I didn’t care if someone heard us. With his rough tongue sliding up and down my clit I had my first orgasm with another person in over a year. It was massive. My entire body quivered and trembled. There was a pleasant shock waves starting at my clit and shooting in every direction through my body.

He pulled his head back out from the skirt and smiled up from the street. I lifted the skirt to pull my panties up when the side door to the bar swung open and a few people stumbled out. The glanced at us, and it had to be obvious they had just missed something.

“Let’s get out of here!” I said and grabbed Robin’s hand without thinking.

Without looking back we fled the alley and turned in the direction of the hotel.

Moment later we were in the hotel elevator. I hadn’t even thought about what was going to happen next. I was still feeling great. And maybe a little embarrassed about how close we’d come to being caught. I hit a button on the elevator.

“That’s my floor, too,” he said.

We got off on the same floor.

“Your room or mine?” he said.

It had definitely never been my intention to let things go that far. But without even thinking about things or about whether we should call it a night, I just answered him.

“Mine,” I said.

Before the door to the room even closed I was at the buttons on his shirt. I wanted to fuck more than at any time in my life. I got impatient and just tried to pull the shirt over his head. Buttons popped and flew across the room.

He unbuttoned my dress down to the waist. I shrugged out of it and stood there in black heels, stockings, panties, and bra–I’ve always been one of those strangely OCD women who almost always matches my underwear. Robin looked stunned. He gazed at my tits. And my flat stomach. And my muscular legs.

I got his pants undone and they hit the floor. His boxers followed.

His cock was already getting hard again, but I decided to help him out. He leaned against the wall in the foyer of the room while I dropped to my knees. I took his thick cock between my full lips. I could taste the cum from earlier all over the head.

I bobbed up and down as Robin ran his fingers through my long, blond hair. He got stiff quickly, but I didn’t want to stop right away.

“I want to fuck,” he said.

“Mmm hmm…” I said, with a mouthful of cock. I slipped my lips off and licked around he head. I tickled the cum hole with the tip of my tongue.

“Can you back up what you said in the bar?” I asked.

“What’s that?” he asked. “I kind of forgot. I was a little drunker then…”

“You asked me when was the last time I was fucked long and hard? Can you do that?”

“Yes!” he said.

I stood up and took my bra off. I thought his jaw would hit the floor as he gazed at my big tits.

“Do you fuck like a boy, or can you fuck me like a man?” I asked, before thinking silently “who am I tonight?” again.

“I’ll fuck you like a MAN,” he said with conviction.

He grabbed my arm and roughly pulled me to the bed. Then he pushed me down playfully. Lying on the bed I hooked two thumbs in my panties and pulled them off. I spread me legs so that I was on my back, with nothing covering me up except the stockings, the heels, and the small path of hair above my pussy.

Again, Robin wasn’t one for foreplay. He jumped on the bed and started kissing my roughly. He kneaded my titties with his hands. And then he got on top and drove that nice, thick cock up inside me.

He was so thick I felt like I was being split open. It had been SO long since I’d had sex. And my ex had just had the standard, average, seven inch white guy cock. Robin’s was FAT.

He didn’t fuck as well as he ate pussy, but it was better than he kissed. There was no change of pace. He just fucked hard and fast–like he needed to cum inside me. And I liked it.

I dug my nails into Robin’s back.

“Oh, fuck me. Fuck me…” I heard myself moaning aloud.

“You like that? You like that?” he kept saying.

His body was dripping with sweat. His breath came in hot little gasps. And still he never broke pace. His fat cock rubbed my clit with every stroke and I felt myself losing control. I called out his name. I gasped. And I came hard. I couldn’t stop myself from digging my nails into his back.

He just went harder. He was like a fucking animal plowing into me. His face was locked in a distorted grimace. His moans were almost like growls.

Just the sound of the two of us fucking and his machine like rhythm brought me to the brink again. I felt my pussy clench as I came for the second time since we’d started fucking.

And still he kept going. Robin grabbed both my legs. He through my heels over his shoulder. The point of my black heels were pointed skyward. Suddenly it was like he had another gear. He slammed into my like a speeding truck into a brick wall. With each thrust he growled loudly. I cried out every time. He slowed down just a bit to deliver hard, deep strokes. I started rubbing my own clit, desperate to cum one more time with him.

It was close to a simultaneous orgasm. I could feel his hot load spraying inside me as the waves of pleasure washed over me. Robin kept right on fucking until he squeezed every drop into me.

He rolled off and the two of tried to catch our breath while we stared at the ceiling.

“Did I fuck you like a man?” he finally asked.

“That depends,” I said. “You got one more in you tonight?”

He looked down at his own cock. I followed his gaze. He was already getting hard again. I’d forgotten that particular advantage of being with a young man!

“What do you think?” he asked.

And then he rolled over and started fucking me one more time….

Source: reddit.com/r/gonewildstories/comments/90qlk5/fm_closing_in_on_40_i_impulsively_decided_to_let