Anal Archives — Page 257 of 957 — NSFW story

My Catholic ex-wife and I reconnect over the summer Part 3 [MF], [Anal], [Rough Anal], [Angry Sex]

Writing a series of short stories about all the gonewild weekends my ex-wife and I shared from May until Nov 2021.

**[Angry Anal on the new Spanking Bench]**

This story starts immediately after [the spanking session](https://www.reddit.com/r/BDSMerotica/comments/rexu53/my_catholic_exwife_and_i_reconnect_over_the/) but not required to read.

It was late afternoon and my freshly showered ex-wife was lounging around on the couch in my bathrobe naked. I made us an early dinner as we watched a movie while giving her thoroughly spanked ass the rest it needed. She was fidgeting, giving me “the look”, overall in a playful mood after the oxytocin rush was settled in from earlier. Constantly poking me in an annoying and poke-the-bear kind of way. I sensed she was horny but the uncharacteristic bratty behavior was not normal.

When that wasn’t getting the reaction out of me that she wanted, she started in with the lip and backtalk. I figured she was acting the part of her “brat” roleplay. I gave her a masochistic order that I knew would bait her into lashing out. Boy did she ever. Read more »

I [M] ripped my wife’s pussy – Tell me what I should do to her now her pussy is out of commission

So if you have read my posts from the last couple of days ( check me profile if not ) you will know I’ve been fucking my wife super dirty for a few days now.

Yesterday I fucked her pussy with 4 fingers inside her too. Her pussy is actually tiny so it really ruined her so now her pussy is out of action.

She is still super horny and wants to get filthy when I get home from work.

She does like anal but I’m not sure if she will be up for it today or not.

She likes it rough, being slapped, squeezed, pulled. She likes getting her throat fucked and wants to be covered in my cock.

She loves eating ass and likes getting spit on too.

I want you horny girls and guys to come up with ideas of what I should do to her tonight.

Don’t hold back. She is such a slut these days and she loves cum!

I will definitely do pretty much anything you come up with and will post tomorrow to let you know how it went down

The first time I enjoyed anal was with a bisexual man [MF]

By popular demand, you filthy animals. Here goes nothing…

I’ve mentioned briefly in stories that I’ve partaken in this particular act but I’ve held off on writing about it. Why? Anal is vulnerable and riddled with certain aspects that are inherently unsexy and kind of hard to write about accurately.

*Trust me, don’t skip those parts when trying this out. Preparation and aftercare are important.*

The first time I had anal was with the guy I lost my virginity to. I’ve never written about him. There’s not much to write unless someone on here has a fetish for missionary and unrealistic expectations of vaginal penetration.

The dude never went down on me once, hated experimenting, and told me using toys to get off while we were together was “cheating.” He’d get weirdly offended if I got myself off with or without him too.

*Men, please don’t be like this. Clit orgasms are a dream. I can orgasm through penetration and I still beg for this.*

So yeah, the first time I tried anal was not enjoyable. He made me feel selfish for asking for lube (so we did not) and he came inside me without us discussing it. Read more »

Amnesia Was The Best Thing To Happen To My GF [?/?/?/?] Part 52-1

[Home](https://www.reddit.com/user/Teososta/comments/q3su15/amnesia_was_the_best_thing_to_happen_to_my_gf/)

=== ***Chris*** ===

The girls seem to be getting along well. Bella and Alexa have been going to the gym with Roxxy and Alana, and I’m glad that they’re all bonding together. I just want them to be happy, that’s all I want.

Victor has invited me over for lunch, which I gladly accepted. He’s been a good friend and we have a lot in common with one another.

So I walked into the restaurant, a Mediterranean place near the hospital, to see Corey and Victor sitting on a booth table facing me.

“Yo, Chris!” Victor called out as he waved me over, but I’ve already seen them.

I sat across from them, their smiling faces. I’ve met Corey a couple of times before, he was in the party with Alana last year when she got her BSN and at my birthday party. Corey looks a bit younger than us, despite being a year older than I am, while Victor always looked about the same, though he’s cut his hair now.

“What’s up guys,” I asked as soon as my butt hits the seats. The waitress soon followed and I ordered a gyro and water. Read more »

My usual days. [gender fluid] [straight, exh]

I don’t really know what to tell you.

So you want to join the club, huh? What are you looking for? Easy money? Higher return on your assets, because that is quite reasonable, I think. You have been unfortunate enough to experience men-duds and it’s time to stop blaming yourself and take up the opportunity to be an independent woman who is successfully in charge of her destiny.

I promise you to make you into a very high paid actress with absolute minimum exposure. You will be able to maintain anonymity and you will never have to show your face on camera. You will be able to work the hours you want and have total control over your time and exposure.

Of course there is some minimum of time required for you to put it and we would have to evaluate your suitability within The Empire.

What is The Empire? The Empire is the the ‘sex umbrella’ that all my erotic creations fall under – so they are all distinct but satisfy all the organic cravings of a biological male, as that is our prey. Yes, prey. We will use every advantage that biology has given us and that is our femininity and vaginas. I will use my femininity and my big dick, and you will use your femininity and your vagina. Read more »

I[F] spent the night with my husband’s high-school bully[M], again, and I couldn’t walk straight afterwards

Like I said before, I gave my husband the same “all nighter” excuse again, while clocking out at a normal time and going over to his bully’s place in the city. I made my last post a day early, losing track of the day in a lust-filled anticipation. I was curious as to what mood it’d be this time, if it’d be the passionate one like in the hotel, or the degrading one of the first all-nighter, and I’d get my answer Friday after lunch. When I returned from lunch I found a box on my desk, with a note, “I expect you to be wearing this when you come over later, I’ll be checking 😉”. What was in the box was a decently sized metallic butt plug, which I reluctantly put in on my way out to his place (there were a few bumps in the road in which I was close to cumming right there in the car) Read more »

Losing my anal virginity to an older woman.

Well, a little back ground. I grow up living in the same
house all my life. Our next-door neighbor was a lady that was a nurse. I think
she lost her husband in a car crash and was widower. I think she dated but we
never really saw anyone stay around. I can so see why. We all called her battle-axe.
You could tell she was always in charge and liked it that way. My mom was never
great at medical stuff so whenever there was a problem. She always nocked on
her door for help.
I would say that was the only time we would ever see a smile
on her face. She loved when people would need her help for something. That was
her weak spot.
We I’m 30 now and my mom and dad were going on a trip and
wanted me to stay at there house to keep an eye on things as they will be gone
a month.
I was at my mom and dads and a couple of weeks in I was not
feeling good and it hit me. I had not used the bathroom is like a week. I look
around my moms house to find something to help with it and we had nothing. I
didn’t really want to go to the store but I had no chose.
I dressed and walked out and Mrs. M was just getting out of
her car as I was getting ready to get in my car. She knew I was there to look
after the house and so she tells me. I’m just next door if you need anything.
Thank you, Mrs. M.
I get in my car and my stomach is not feeling good. I know
Mrs. M would know what to do as she was a nurse all of those years. I see her and I say, Mrs. M you may be able to
help me. I walk up to her and get close as I’m a little embarrassed. Do you
have any stool softeners?
She smiles and tells me, Oh yes Hun. Come in I will fix you
right up.
I have always felt safe with her as she has taken care of me
a lot in the past.
She comes out with the pills. She then asked me, how long has
it been?
Oh, I think maybe a week.
Oh Hun, that is a long time. This may not work. And if it,
does it will be for ever to run its course.
What should I do?
She walks away and comes back with a enema bag with a tube
on it and holds it up to me. She can see my look of “what the hell am I going
to do with that” look.
I knew what it was but never in my life used one.
She then said, I bet you have never used one of these.
No Ma’am.
She then tells me to fallow her. She takes me to her room.
She goes in her closet and comes back out with a silk robe.
She hands it to me and tells me. She will get the bag ready
that I need to undress and put this on.
She walks out of the room and I do as told. When she comes
back. I’m standing there in just the robe. She goes and gets a pad to lay on
the bed and tells me to lay on my side with my legs as she puts them. She walks
back in the bathroom and is looking for something. A few minutes later she
comes out.
I can’t find the Vaseline, She opens a drawer next to the
bed and pulls out some lube. This kind of shocked me. 1 I have known her most
of my life and never thought of her in a sexual way at all. So, seeing she does
was a little bit of a shock. 2 she was
always the battel-axe, who would want her? 3 at 72 does she have toys or a
lover?
So, she lifts the hose and shows me and end. I’m going to
lube this up really good and slowly slide this in. I knew that was what was
going to happen at some point. But I tried not thinking about it.
I see her put lube all over it and strokes it with her
fingers making sure it was lubed all around. She then rolls the robe up and
makes my ass hang out. She tells me to spread my cheeks and I think for the
first time. I’m embarrassed. I can’t look at her as I do this. Then I feel the wetness
on my star and I jump a little.
It’s ok Hun, I will make sure you are nice and lubed and go really
slow.
I can tell it is wet but at the same time it is nice and
warm. I look back and it is her finger on my star and she is lubing me up. Then
I feel the end on me and she does just like she said. She went very slow. After
it was in me, she rubs my butt a little and tells me she is going to start now.
That is when I felt her open it up and I started to feel
full. I told her and she helped me get use to it and she loaded me up. As she
is filling me up I see the lube bottle and it is warming lube and now I know
why it is so warm down there.
I moan as it is not the most comfortable thing to feel. I’m
trying not to think of anything as I need to hold it. At some point her hand
slides in my robe and she is rubbing my chest and tummy helping me relax.
Then I moan and my eyes jet open. At some point I got hard
and her arm just brushed over the head of my cock. She rubs my chest and works down to my tummy
again. Sure enough. Her arm rubbed over my head again and my body shivered and
jerked.
She slides her hand out of my robe and tells me it is time
to get rid of this.
I go in the bathroom and do what I needed to do.
After I clean up really good and come back out and I’m
standing there in just the robe still. The odd part is I’m still kind of hard.
Not standing on end but not laying down. So, it is kind of sticking out. I see
her looking right at it. And I look down and see why she is looking and I turn
red.
She then tells me; we should make sure you are empty.
She tells me to get on the bed on your knees. I do as told.
She walks up behind me again and rolls the robe up and lays
it on my back. Then I feel lube running down my check and over my balls. I feel
her finger rubbing the lube all around and the feeling is…. Ok I will say it.
It felt so good. She is letting her fingers run all over. My ass, taint, my
little star. Then I felt a little pressure on my star and then in me. My body
is on its own now. I should be stopping her but my god please don’t stop I
think to myself.
It was not long and I can now feel her slowly sliding in and
out of me and I’m full-on rock hard now.
As she slides in and out of me more. I feel my hips rocking
with her. My moans are telling her everything she needs to know.
I can feel her going deeper and pushing something. What ever
it is I swear it feels like she it inside my cock.
I feel her speed up and working me a little harder. Fuck I
need to cum I think to myself.
I feel me pushing back to her finger as she fucks me with
it.
I moan out, “oh fuck “ “oh fuck I think I’m going to cum”. I
feel her push all the way in me and grind. I’m so close and I grab my cock. She
takes my hand off me and she tells me. Let me do that. She starts stroking my
balls as she works her magic in my ass.
My body is twitching and I’m just a moaning mess.
Then it hits me. I start to cum. She works her finger in me
harder and then she wraps her hand around my cock and starts to milk me dry.
I can’t take any more and I fall and roll to my back. I open
my eyes and she has a big smile on her face and she is licking her fingers from
milking me.
I dress and leave. Thinking, there is no way in hell I’m not
going back to see her.

Megan’s Slutty Adventures: A Birthday Spitroast [hotwife] [bj] [anal] [gagging] [anal play]

It was Megan’s 29th birthday and she was feeling a little dejected. It was her last year before she turned 30 and she’d be determined that she’d celebrate this year with a bang. She’d had a nice dinner with her friends, fun birthday sex with her husband, mark, that morning and than homemade breakfast, a host of thoughtful and fun presents from family and friends….but there was just something missing. There wasn’t anything exciting, rash or even…dangerous about it. She had wanted to live it up.

As Megan and Mark walked back home from dinner, Mark surprised her. He stopped at the intersection that would lead them home, grabbed her hand and said:

“We’re not going home quite yet” and proceeded to turn her down another street, that led away from their apartment.

At first Megan protested, feeling tired and grumpy after the unsatisfying birthday, but something about Mark’s demeanor caught her off guard, intriguing her enough to follow without complaint.

They approached the entrance of a ritzy, boutique hotel and walked through the door. Mark walked up to the concierge, said a few quick words and was handed a key. Read more »

I [NB] traded firsts with my hookup [NB] after a long pandemic-related dry spell

After almost two years without a hookup, I was pretty damn excited when I clicked with someone I met on a dating app and we quickly started making plans to meet up. Like me, Lex was nonbinary and bi, and ready to get down to business. They shared that they’d had partners before but never anyone with a penis and really wanted to bottom for the first time, which I was more than happy to help out with. I mentioned that while I’d had a fair number of hookups, I’d never had anyone actually finish in my mouth and as long as I was justifying a certain amount of acceptable risk for COVID (though we’re both fully vaxed) I might as well take the plunge and get my first taste of someone else’s cum. Needless to say, we were both pretty eager to meet and check off a couple of “firsts”.

Becoming A Sissy Sex Slave (Flash Erotica)

I couldn’t believe it was happening. There I was, dressed up in stockings and lingerie like a cheap whore with my cock locked up in steal chastity. I was fucking myself with a vibrating rubber dick while desperately sniffing and kissing Morgan’s stinky nylon feet. I couldn’t believe the girly sounds coming from my mouth as I experienced my first sissy-gasm, dripping my excitement all over the hardwood floor.

“Say it!” Morgan said, shoving to toes right up against my nose, “Say it out loud!”

As tears of both remorse and desire ran down my made-up face I cried out, “I wanna be your sissy whore!”

With a wicked grin Morgan replied, “Then it is time to take it to the next level.”

That was when I heard the footsteps of her boyfriend walking up slowly behind me. His hands caressed my ass and I knew what was about to happen next. I was about to lose my anal cherry to a man and become the sissy sex slave I always wanted to be.