Anal Archives — Page 24 of 957 — NSFW story

My (M30’s) boss (F30’s) said she’d fuck whoever fixed this thing at work so I took her up on that

“Hey, boss, you have a minute?”

“One sec, but come on in.”

I slipped in to the office, quietly closing the door behind me. Jenny glared at the screen, typed out something with a definite air of finality, and clicked send before spinning around with an exasperated look.

“That useless director was ‘reminding’ me, again, to finish that process eval. I ‘reminded’ him, *again*, that we finished the process eval three months ago and sent it to him for review. Ugh. Anyway, what’s up?”

I’d been thinking about this moment for a while, but it was different having her face *there*, not just imagined.

“Well, Jens, if you check our team folder, you’ll find something new.”

She raised an eyebrow, waiting for more, but I just grinned and spread my hands. She snorted and spinned back to her computer. “Alright, Mikey, we’ll play it your way. Let’s go see what this special-*whAT?*”

It was everything I hoped for. The little half-screech, the slack-jawed expression, the scooch forward to stare closer as if she couldn’t believe her eyes.

“Oh my god, Mike, you *did it?!?”*

I kept grinning, and gave a flamboyant bow from my seat. Read more »

My first time with a trans woman [MT]

Awhile ago, while swiping through tinder, I matched with a trans girl. I didn’t notice at first because I wasn’t reading profiles and she was very attractive. Let’s say her name was Katie. After we matched, I went back to her profile where she mentions she’s trans. I hadn’t previously considered meeting up with a trans girl, as I figured it wouldn’t be my thing, or I couldn’t get past the obvious hurdles. However, Katie was a looker. Five foot six or so, slim, gorgeous blonde hair, big soulful eyes, pale skin. She had several photos of her wearing cute dresses on her profile.

While I’m mulling over whether to shoot my shot, she sends me a message saying that my facial hair is cute. I’m about 6’1″, athletic swimmer type build, and naturally tan, but I’m horrible at talking to women so her messaging me first was greatly appreciated. Read more »

My Hot Wife and Daughters Hotter Friend Sequel Part 3

Candace POV.

I said goodbye to my parents and grabbed my phone. I had a text from Jess, “Sorry girl, I am running behind, I wont be there until around 2”

I looked at the time and it was 12:30. I had an hour and half to kill. I responded back to Jess, “no problem, see you then”.

I scrolled up to the dirty things she sent me last night and I felt my pussy starting to get wet. I dropped my gym shorts and laid down in my bed. I flipped through our chat and I stopped at the last picture of two cocks in her mouth and my free and started making circles around my clit. I closed my eyes thinking about the last time those lips ate me out. I focused on the picture again and wondered what that big cock would feel like inside me. Read more »

[MFM] Anal cheating

My ex boyfriend (40M) was never a fan of anal sex.
He was older than me (19F) and went through phases in life where his religion became absolutely paramount.
He was a good man and provided for me, but I began missing anal sex incredibly.
I’d always enjoyed being fucked up my ass and have my most intense long lasting orgasms from being fucked up my rear hole.
So with my then boyfriend refusing to take me anally, it was totally frustrating for me.

We attended a dancing competition last summer, where my boyfriend was a judge.
As he was busy, I got chatting to two guys I go to college with. After some small talk, I told them how horny I was for cock and especially anal sex.
Five minutes later in the woodland close to the field where the competition was being held, I was sucking on one of the guys cocks, while the other guy was tonguing my pussy and asshole from behind.
We all knew we didn’t have much time, so there was no getting to know you sex. And my asshole over the next twenty minutes or so took a beautifully hard and deep pounding.
Both men fucked my mouth, pussy and ass. And at one point I sat on the older of the guys cocks as the other guy fucked my asshole. It had been nearly a year without anal sex, and trust me I became utterly wild for the two men. They had me climaxing like crazy and I just couldn’t get enough of them fucking my rear hole.
By the time they’d both cum up my bum (my insistence) I’d probably orgasmed half a dozen times. Read more »

Falling For A Sissy [M32/F24] [Romance] [Sissy] [Deep Throat] [Anal]

Like most other people on our planet I have to go grocery shopping from time to time. It just has do be done. Not that I love doing it, but well, one thing that I like even less is starving. Or running out of snacks while hanging out in front of my TV.

To prevent such accidents from happening I headed into the grocery store not far away from the place I was living in. About two times a week, sometimes even three. Because stupid me tends to forget buying non essential stuff like canned tomatoes when planing to cook some pasta with tomato sauce.

I normally go grocery shopping on Tuesday and Fridays, always after work. I take a huge bag with me and on my way home I get some food supplies. But when I am on vacation, or when I have days off, I do my shopping in the late morning hours. Because there are by far less people are in the store and it makes grocery shopping a much more relaxing experience. Read more »

Nikki {53m/23f} {bdsm/bondage/anal}

I’d seen Nikki on various dating sites now and again. Her profiles would come and go. I always messaged her. Was always a short, polite conversation that invariably ended up with her saying, “Thanks. But I don’t think I’m interested. I think you’re probably a little too old for me.”

She probably had a point. She was a twenty-year-old university student, and I was thirty plus years her senior.

One day I saw another new profile of hers again. I said hello again and we started chatting. She was feeling down about something, I can’t remember what, but I talked her into letting me take her for coffee at Starbucks

She was a short raven haired BBW. Somehow a combination of super cute and super sexy. Never all of one, or the other, but a good combination of both. A charming smile despite her supposed sadness and she exuded an excited energy. Big, beautiful, bright, blue eyes. She had great tits and a nice round ass. A bit of a brat, but she was a delight to look at. Read more »

The Wrong Threesome [MFM]

When my wife, Anne, and I first became a couple, we talked a big game about how kinky we wanted to be. But the truth was, we were both pretty nervous and shy. We’d had a few exciting encounters, but it was really challenging to get out of our comfort zones. And it was frustrating.

Anne had a roommate that can safely be described as insane. She was older than we were and smoked an amazing amount of pot. She was also very open about sex. Almost obnoxiously so. She would leave her sex toys out in the main room, or leave porn playing on the TV even after she’d left. Anne was quietly determined to fuck her before graduation.

We had a party at the house one weekend. A ridiculous rager where we bought a keg, then sold drinks to anyone wanted to drop by until we made enough to buy another keg. The house was trashed, it was amazing. We partied, fell asleep, woke up and partied some more. Ultimately we ended up in Anne’s bedroom. The two of us, Jim, a friend Anne had known since elementary school, and the roommate. Both Jim and Anne were flirting with the roommate. But badly, neither was good at it. Sort of randomly, the roommate got up and wandered out. Read more »

Get an ejaculating dildo they said. it will be fun, they said…[MF] pegging

I’ve recently broken open my previously tight butthole with the help of a bunch of cool toys.

I’ve been pegged for years, but i always had to open my ass slowly. Now, I can just pop in relatively large toys. My butthole stretching yogic practice has paid off!

On a recent trip to “Does your mother know” in the Castro, we bought an ejeculating dragon dildo. It’s awesome. We used it on her pussy a few times(epic), but our goal was for her to peg me with it and fill my ass with her hot cum.

We got high, I washed out my ass, but apparently forced some water up past the second sphincter (user error) and I tried to put the dragon dick up my ass without the bulb or the syringe on the end of the tube.

It’s a good thing we were in the bathroom. The minute the dragon dick head got to my asshole, a thin trickle of slightly shitty water dribbled through the ejaculating dildo tube and onto the floor.

Of course, we just about died laughing.

There should be simpsons style warning “may cause anal leakage” Read more »

Example Bespoke Erotica #2 [F27, M27]

Another example of bespoke erotica I was asked to write. This time the themes were:
After-party, friends with benefits, [squirt], [rough sex], [anal].

[F27, M27]

We both knew how this was going to go as soon as we knew we were both going to the same party. That’s one of the things I love about having a friend with benefits – there’s a mutual understanding of when and where things like this can happen. That, and the fact that we both know exactly what each other enjoys. For example, I know that you wore those yoga pants to this party just for me.

It’s 1am by the time we get back to my AirBnB. Initially things are fairly civilised – we open a bottle of wine and spend a few minutes chatting in the kitchen. You’re sitting on the kitchen counter, and I’m standing opposite you, admiring the view. Gradually, I move closer and closer, until we give in, and shatter the illusion that we are just friends. I kiss you, gently at first, then harder and harder. You pull off your jumper, then pull me in closer, our tongues intertwined. I lift you off of the kitchen counter, and carry you through to the bedroom – I can feel your nipples pressing into me through your t-shirt. Read more »

[F] I went to university with an anal plug and everyone noticed

It was during my chemistry degree and my best friend at the time (who was just as much of a nymphomaniac as I was) often challenged me and one day she told me to come to every class with an anal plug
Obviously I’m a big slut so I did it and the day went like this:
• the first two hours I was moving all the time in different positions and that gave me a lot of pleasure nobody was paying attention everybody was asleep.
• from 10am to noon we had changed rooms and I continued the same one, it was really the kiff I was pushing little moans and nobody was really noticing
Everything got complicated when we went to eat at the canteen, we sat down and finished eating and when I got up I screamed because the anal plug was magnetized to the chair and so when I got up it came out of my asshole and stayed attached to the chair for everyone to see. As you can imagine everyone looked in my direction after I screamed and literally the whole canteen noticed the plug on the chair. It was a real shame but a bit of a turn on and I got my revenge on my best friend, you want to know how?