Pleasure Island – A Jennifer Stokes story – ch.16 [f/f/f/m][20s-30s][kissing][mild groping]

16.

The party was in full swing by the time the girls arrived, just as the sun was beginning to set.

Tiny white lights were strung between the trees, sparked like tiny stars in the sky, and tiki torches lined the pathways, lighting them with their fiery glow.

Grabbing a drink from the nearest server, they strolled amongst the other guests.

There were quite a number of people gathered around, and Jennifer had some concerns about someone recognizing her. She said as much to her friend.

Tess stopped her and said, “Jenn, we’re on an island in the middle of nowhere. Come on, relax. Let’s grab another drink and see if we can’t find someone to fuck. That’s why we came, right?”

Nodding her agreement, Jennifer said, “You’re right, let’s go.”

A few minutes later, Tess spotted a cute asian couple she had seen earlier that day near the pool, and steered Jennifer toward them.

They quickly struck up a conversation after the introductions were made. As it turned out, the couple were married and heading up the newly acquired South Korean branch.

The cougar next door.

It is funny how life is. I’m not a young man any more. So,
my out look on cougars are much different than they use to be. I guess you can
say I lost my virginity to a cougar when I was 18.
I know you are reading that and thinking to yourself how do
you guess you lost your virginity? Lol well, I say it like that as I had a girl
friend I was dating at the time that we did just about everything but vaginal
sex. We did oral like it was going out of style. And the first time I fucked
her was anal. She didn’t want to get nocked up and I didn’t have a condom at
the time and we were both so worked up. She said I could fuck her ass. Well,
being young and not truly prepared it was well ok. I did fuck her but if was
gross as we were not ready the right way and well it was our first time. So, it
was just ok.
Then I met a lady at the store where I worked and one thing
led to the other and I got to fuck my first pussy. I was 18 and she was 49. I
was hooked on cougars for a long time after that.
Then I started getting older and found myself going from the
cougars to hitting on girl younger than I am.
So, here I am, this older guy. I guess you can call me a
DILF and thank God dad bodes are in now lol.
So, I have been on a run of younger girls. They are fun, and
the tight bodies are damn hot. But I do find that they are really not that good
in bed. But the eye candy is great.
One night I was having a party at my house. I let all the neighbors
know and invited a few. You know being nice and not wanting them to call the
cops to turn down the music etc.
Let’s talk about my neighbor, she is in her early 70’s. Very
nice. Her husband passed away about 3 or 4 years ago.  I got to know them well, and they were a very
nice couple to live next to. From what I can tell by talking to them. She was a
bit of a player back in the days. I did see some old pics of her and she did
look hot back then.
 Now not saying she didn’t
hold up at her age but you know. I have been dating girls much younger than me
for a few years now and I’m well, a little jaded.
I have a very nice hot tub in my back yard and it is nice
and privet. Except one little spot that if you are in her sewing room looking
out the window you can see my tub. In all the years I have lived there I know
she has seen me naked in it a few times. But nothing was ever said.
So, I’m having my party and my neighbor is over hanging out
with everyone one. I thought it was odd as I never see her drink and she had a
glass of wine in her hand the whole night.
The girl I was kind of seeing pissed me off and I told her
to go home.
It was a very cool party and everyone was having a great
time. The hot tub was busy and the drinks were flowing. I did notice my
neighbor chatting with a few people and it looked like she was having a really
nice time also. I’m not sure I have ever seen her smile so much after her husband
passed. But she was having a great time and I made sure to talk to her too and
let her know how happy I was she was there having a good time.
After that talk it was different. I think she thought I was
flirting with her. Now I’m lit from the party and I’m one big flirt most of the
time. But I really was not going there with her. But her smile made me happy
and I just let it be.
It was the end of the night and I was cleaning up a little so
it would not be to bad the next day. As I’m picking up I see her and she is
helping.
You really do not have to help.
Oh, but I want to. It is the least I can do to thank you for
the invite. I can not remember the last party I have been to. Let a lone one
that was this fun. I really did have a great time. Thank you so much.
Please it was no problem. I’m so glad you had a good time.
As we were cleaning up. She looks at the hot tub and with a
small pouty face. I didn’t get to go in the hot tub. She had this cute smile on
her face and said, I saw some people having a lot of fun in there.
I laugh and say sorry for that. Yes the hot tub has made for
some fun times.
Well, I’m bummed I didn’t go in. you will have to have ne
over for a hot tub night.
I was buzzed and I guess I was not getting the hunts. Lol
So, I tell her. Well, I’m getting in to unwind after I
finish this. If you would like to join me.
She gets a big smile and tells me. I would really like that.
I will run home and get my towel and robe and be back.
Again so not on the same page as her. I pick a few things up
and I go in and grab a towel and change into my shorts. I put my robe on and
walk out.
She has made it back and is in the tub already. She is
pushing the buttons trying to get it going and that is when I notice she is
naked in my hot tub.
She sees me looking at her naked body.
I hope it is ok me being naked. I know you prefer it when
you are alone. Her hint she has seen me naked in the hot tub. I didn’t want you
to feel you needed to cover up for me if this is how you unwind and relax.
Here let me turn this on for you. I hit the buttons and I
ask her. If she would like a night cap.
I would like that.
She had been drinking wine tonight so I thought I would
stick to that for her. I want inside and got a new bottle of wine and 2
glasses. I am getting ready to walk out and it hits me I still have shorts on.
I think to myself, she is naked and I don’t want her to feel
out of place so I slip my shirts off and walk out in my robe.
I poor us both wine and clime in.  
As I’m getting in I see myself chubbing up and when I get in
she looks right at it.
I can not help it I feel myself getting harder and harder
knowing she looked.
We hang out and small talk.
She is talking about how good this hot tub feels and I look
over and she has her head back and eyes closed and her tits are floating. Her
nipples are rock hard and my cock is twitching looking at her tits.
I wish I could say she had the finest body I have ever seen
but. Let’s be real. She is no young girl any more and she is full woman and she
is in all the right places for her age.
As I’m just chatting with her, I see her start to float
herself. Her feet are sticking out of the water and her hairy bush is poking out
also. I should be looking away but I can’t.
I’m looking her body up and down taking in this older lady
next door to me.
She is smooth from head to toe except her bush sticking out
over the water. Her tits swaying in the water as it bubbles around her.
I get to her face and that is when I see her looking at me
looking her up and down.
She smiles and I turn red.
She drinks her glass down and stands up and walks to me. She
reaches for the wine over me and makes her tits brush my arm.
I think the touch of her and me we both moan a soft moan to
the touch.
She puts the bottle back and instead of moving back and
setting down she stays standing in front of me.  
She is swaying as she talks to me and I cannot help but to
look at her tits as she does.
She can not stop smiling as I keep looking at her. I rub my
hand over my hard cock a few times under the water. Every time I catch myself
and stop. But I’m fucking horny and drunk and fuck I’m turned on.
I can’t stand it I need to touch myself. Just as I wrap my
hand around my cock. The timer ends and there I am. Looking at her tits with my
hand around my cock and she can see everything now.
I do not know what to do. I’m embarrassed and stuck for
words.
She slowly steps up to me and puts the wine glass down. She
peels my hand off my cock and replaces it with her hand. No words are said. She
slowly starts to stroke me.
It felt amazing. The girls I have been with the last few
years are all young and just want to fuck. Great I know but this woman made me
feel so good.
She was so soft. It was like her hand was made for my cock.
She was in no hurry and just looked in my eyes the whole time as she played
with me. I have never had a hand job like this. Her hand felt like she lubed it
up. It was so soft and silky smooth. She would stroke from my base to my head
then she would wrap her hand around the head of my cock and do this slow twisting
motion. Then she would slide her hand all the way down my shaft. She would run
her finger nails over my balls and taint. Then grip me tight and stroke me a
few times only to start it all over again.
Every time I would get close she would run her nails over my
balls and taint to calm me down and then back at it.
I’m not sure how long this all was but I’m in heaven. That
is when she shifted her grip and I felt my hips jerk up into her hand.
She knew she had me and she bent to my ear and I can feel
her warm breath in my ear as she stroked me.
She whispered in my ear. “Cum for me”
That is all I needed. I started to fuck her hand as she
stroked me and I was moaning like it was my first time.
I could not last any longer and I started cumming like no tomorrow.
 
I was full on spent I came so hard. We got out of the tub
and she hugged me and kissed me on the cheek and said good night as she walked
away holding her robe and still naked.

I Finally Fucked My Step Sister Part 2 [MF][Fiction]

[Part 1](https://www.reddit.com/r/Erotica/comments/z8jkft/i_finally_fucked_my_stepsister_mf_fiction/)

Bridget slowly pulls herself off of my throbbing cock as my warm cum drips out of her tight pussy back onto my cock. Without hesitation, she moves her head towards my cock and cleans my cum off it with her tongue. I squirm with pleasure as she teases my sensitive cock with her warm tongue. She didn’t stop there though, she pushed my head down and straddled my face. I could see my cum still dripping out of her pussy. Before I can react, she buries my face between her legs. She’s way kinkier than I could’ve imagined. I let out some soft moans as I tasted myself along with her juices dripping all over my face and down my neck. I could tell she was still sensitive by the way her legs were shaking while she rode my face.

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The Watcher (MF)

I watch. It’s what I do. But never like this.

I’ve watched you leaving the building across the street from my own, sometimes with him, sometimes alone. You caught my eye, yes, but not my imagination. Not then.

But later – some weeks, maybe a month later – early one evening, as I stood at my window watching the light change as the workers scurried home, just a glimpse of something. So brief that I thought perhaps it was my imagination. Had you really left your blinds open as you dressed? It was so fleeting I couldn’t be sure. But in my mind there was skin, shape, suggestion. I was still standing there, intrigued, when the front door of your building opened and out you stepped, on his arm, the two of you chattering and laughing.

And that became my place. To watch for you. You became my fantasy, my muse, my obsession even. Rewards were few, but every now and then my patience earned me what I yearned for. I have seen you in every state of undress. I have seen you take him in your mouth. I have seen him choke you, spank you, even hit you. I have seen you masturbate; sometimes with toys – a glass dildo seems to pleasure you most – sometimes with your fingers.

Review – 129 min couple challenge

We have tried our own 120 min challenge. We couldn’t last for 120 min and we even didn’t have sex, but it was really really great time.

We were sitting naked in the living room and drinking coffee. Before the start we removed all clocks and mobile phones so we can’t tell the time.

We started the challenge slowly and carefully, after all we have 120 min. During kissing I lay on the back behind him and started kissing him at the back. He stayed that way and only leaned to my legs to kiss them and massage them all the way.

Sensual tension was building really fast that way. After a while he comes above me so I lay on my back. He was kissing my butt cheeks, legs and stomach while I was touching and kissing his legs and stomach that was above my head.

We were horny as hell and there was only 15-20 minutes passed. Then he slid back so his mouth was above mine and we started kissing passionately. I gently started touching his cock and balls while we were still kissing.

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Office Fantasy Adventures Part 1

My workmate’s name is Tim. He’s a cute little ginger with a mop of strawberry-blonde hair. He’s a few inches shorter than me, but otherwise, we have the same build. I like him a lot but I’m not sure if he likes me back.

We work in Accounts Payable and there’s a lot of paperwork involved. It’s a nightmare trying to get everything squared away before the end of the month. One day he asked if he could take a walk with me. We were in the middle of a big project and he wanted to get out somewhere quiet”, he said. I said yes and off we went.

It was a beautiful day and we walked along the river for about twenty minutes. The sun was shining and the birds were chirping. It was a perfect day.

We got to a bench overlooking the water when Tim stopped.

He put his hand on my back and said, Do you want to kiss me?’ I said yes and we ended up under the trees kissing. It was wonderful. He tasted like honey and I could feel his hands all over me.

I felt like an escort when I accepted money to fuck an older guy in a hotel [26F]

This is way more recent! Due to the pandemic I had to stop working at the bar where I previously worked as a waitress and from the moment I could, I found myself another waitressing job. This was at a more fancier place which functioned throughout the day more as a high end bar and then at dinnertime as a restaurant.

Throughout the afternoon a man in his mid-forties had been working on his laptop at one of the tables. He had been buying drinks and snacks the entire time, gave good tips and kept to himself so he was a nice customer to have around. He spoke English with a British accent and he turned out to be in the country on business for a few days.

We chatted a few times and we had a nice match. Suddenly he asked if I wanted to have dinner with him that day, his treat. He said he thought I was a nice girl, we had a good vibe and would prefer it over eating alone. I didn’t have to do the evening shift, so I figured, sure why not! He gave me the name of a restaurant some of his coworkers had recommended and what time I was expected there.

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Focused CEO Part 1 [Rough][Misogyny][possessive][hand job]

Disclaimer: this will be a long read and I plan on continuing this story in further parts. The first part won’t be rough or have misogyny but will be introduced in upcoming parts. Misogyny will only be explored as a kink and not as a belief/way of life. Part 1 only has a handjob, no penetration.

I finally got my first job, and at the company I wanted most, Bellezza InfraTech, a fairly early-stage start-up company that creates virtual, and real-life infrastructure products that connect and interact with the client company’s development environment, and helps make milestoning, and communication between different parts of the company easy, and more presentable, providing an AI produced User Interface to make it easier for non-tech teams to understand the status of development, for the development team to test features, and to present to stakeholders without needing the development team to invest resources into the front end until they wish to.

The company has made its first product and in the past has only hired experienced developers to make its initial product, but now I, a fresher, have been hired as they have moved on to their scaling phase, making the product work with different development environments as it currently only works with some industry-leading development environments.

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I Finally Fucked My Stepsister [MF] [Fiction]

Here is my first go at writing a sex story so any tips, suggestions, etc. appreciated :)

My parents have been divorced for a while now. When it happened, it felt like my world shattered, but little did I know, I would be getting some good benefits of my own. Time went on and my dad had a few new girlfriends who came and went, but he found one who was right for him and lucky for me, she had a very very attractive daughter. Bridget is her name and she is what every man dreams of. Tight, fit body, beautiful perky DD breasts, and a perfect ass. She is one year older than me. Our lust for each other didn’t start for another few years though.

Fast forward to when we are 21 and 22, much older and much more mature than when we first met. We got very close as step siblings over the past few years especially since I didn’t have a sister growing up. We were able to connect very well and even though I was constantly undressing her with my eyes, I kept those thoughts to myself. Whenever we’d play fight, I’d always try to graze her perky tits or tight ass without raising suspicion. We were very open with each other, we’d talk about relationship issues, our sex lives, and just mundane things like school. I had just gone through a breakup and was beside myself about it. Bridget was there for me in more ways than one though…

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