Tag: Anal

My first time with a trans woman [MF]

So as the title says this is the story about my first sexual experience with a male to female transsexual, so if that isn’t your thing I’d recommend not reading this story. I’ll call her Megan. Also if I say anything that isn’t the correct term or you find offensive I apologise, I’m not 100% clued up on all of this, so just leave a comment or dm me if I say anything wrong. I’ll try and remember to refer to her penis as her clit, and her asshole as her pussy because that’s what she liked me to call them at the time.

I first met Megan on a dating app and instantly saw how gorgeous she was, she had shoulder length brown hair and piercing green eyes. Nice plump lips and a cute button nose. She was about 5’4 and very petite, her legs and bum were nice and toned from working out and her boobs were about 34C and looked very natural. Obviously I was very interested in her when I first seen her profile and had to message her. I honestly didn’t expect a reply as I thought she was way out of my league, but to my reply she messaged me back within 5 minutes. We chatted on the dating app before moving to WhatsApp. Read more »

[MF] Anal in a church with my best friend

This is part 2 of my story with Jen. Part one is here, the TLDR – I fucked my best friend in a movie theater. There’s a little back story so skip to the — if you want to get to the hot and heavy. 

Her comment about wanting me to finish in her mouth had me frantically googling what made cum taste good – I, of course, absolutely inhaled pineapple juice about twice everyday that week. 

If you’re just coming here – Jen was about 5″3, C cups, and had a volleyball player’s ass. I included a little more detail in the first story. 

Picking up where we left off –

I get a text from her as soon as she gets into the taxi. We did a little debrief about it and talked about some of the highlights. We were still a little shy around each other in person, but once we started texting – she opened up about how she felt like such a slut in there and how much getting fucked from the back turned her on. She regretted not spending enough time with my balls in her mouth.  Read more »

no such thing as a wrong hole [MF] [anal] [oral] [anon]

You weren’t too tipsy yet. You’d only agreed to go to the bar with your girlfriends because it meant getting you out of the house for a bit. No plans to get smashed, but oh, that was changing quickly.

The anonymous man has his hand to the small of your back and the feeling of his warm touch seeping through your pencil skirt already has your clit at attention. Little tingles ping-pong through you, your cunt slippery with arousal.

Gently, you take him by the wrist. You lower his palm until he has a good handful of your left ass cheek and without hesitation, he squeezes. He steps closer to you, chuckles in your ear. “Naughty girl, aren’t we?” he husks.

“Yes, sir,” you answer honestly.

“Good. I like that.”

The walk to his place isn’t far. Only a couple blocks and then you’re at the steps of a nice looking brick-built apartment. His hand reluctantly slips away as he gets out his keys.

You’re glad you didn’t wear panties. The slick rub of your thighs only gets you hotter. Read more »

Vivian Tied – M/f – BDSM and mild humiliation

She’s tied to the bed in his hotel room. Blindfolded. Gagged with her own panties. Nude. And she’s so vividly aware that she has no excuses tonight. She can’t blame the alcohol, though it had been another strong drink. She can’t lie to herself that it was an accident, that she had been overwhelmed by his presence.

She could try to lie to herself, like the day before, that she hadn’t gone to meet him for this reason. That she hadn’t worn the sexy dress with its matching bra and panties like he had instructed to please him. She had no excuse. She had made the choice to meet him. The stranger. She had showered and shaved and dressed to please him, all the while thinking, imagining, touching herself lightly.

It had been such an easy choice to make. Too easy. This wasn’t like her. She should feel bad. She wasn’t the sort of woman to cheat. She had spent the day checking, and double checking, her own conscience. Barely a blip. The regret she felt wasn’t at her actions, but that she had been forced to seek this out. Read more »

My step sister helped me out with a little problem Part 1[step-sister] [con?] [oral] [fictional] [18] [slow paced] [reluctant?]

“Oh my god,”, my step sister exclaimed as she walked in on me jerking off with her bra clenched in my hand. “Not again! I thought mom and dad were paying for therapy for this kind of stuff!”

My step sister has always been hot to me, especially her large breasts. The size most porn stars have, except hers were completely natural. Natural yet firm, I’d been caught spying before as well as using some of her personal items for my own pleasure. It turns out that maybe my step sister wasn’t too pleased with that and told our parents and I’ve been in therapy for a while now dealing with the so called “issue”. In fact it was helping until today, when, I was feeling a particular kind of way.

“I’m telling mom!”

“No, wait please don’t!”, I begged.

“Well, what am I supposed to do? Your my little brother and your jerking off into my bra!”, she retorted.

“I can explain, see I wa-”

“I don’t think that’s necessary, I can see pretty clearly what’s happening! Mom!”

“No please, be quiet!”, I half whispered and half yelled. Read more »

That time I had sex with a total stranger, which was also the first time with another man. [MM]

I hope this isn’t to long!

A few years ago when I was 19 years old I went on a holiday on my own to Croatia. I went to an Island called Vis and regulary went to a bathing place called Stiniva. I stayed in a little vacation home I rented.

On the third day I was there I went to the beach in Stiniva once again and I decided to go for a longer swim past all the boats, so I could swim without being surrounded by others. When I passed the still lying boats I went underwater to see if I could watch fish, and as I was doing that I looked in front of me and I saw a man swimming over me with green swimming shorts on. But this man, he had his giant penis hanging out of it.

I couldn’t believe what I was seeing because he had a very VERY big penis. It must have been about 9-10” long, and it was very thick as well, in the middle it had a fat vein too?. Read more »

My wife finally let me in her asshole last night and it was absolutely amazing… [mf]

My wife has a big and gorgeous ass and I’ve always been obsessed with it. She knows I want anal more than anything but has never allowed me in there. I eat her asshole all the time and she recently started using small “beginner” plugs during foreplay and sex.

Last night she was on her period but we were messing around and I was eating and tongue fucking her asshole deep. Knowing she was on her period I said “do you wanna 69 or can I maybe tease your asshole a little with my cock?”

She was like… “go ahead and tease, but if I tell you to stop, stop…”

I agreed and got out the lube. Her asshole was already very wet from all the tongue fucking but I put a lot of lube on my cock because I didn’t want it to hurt.

I’ve “teased” her before but never really gotten more than like half my head in. However this time we were in spooning position with her ass pushed up towards me and my god was this different. I have a pretty big cock so in no way would I call this full anal, however I got at least a few inches in there and just kept popping my cock in and out of her. It was making the sexiest fucking sounds and FELT INCREDIBLE!! I’ve never felt the inside of an asshole before and I am HOOKED!! Read more »

(F) 41. Fun time. (oral) (anal)

Had a 3some with my fb and his friend, his friend slipped me his number before I left, so the next day I txt him. We met for a drink later in the day, we went back to his place and had sex.
3 days later he messaged me and asked how much fun id like. He told me he has 2 friends at his and he would love to let them watch us fuck. I told him no. If I’m coming over I want all 3. I arrived about 30 mins later, I had a long jacket on and nothing else. I said to my fb friend, one at a time or all at once, we all went into the bedroom and I dropped my coat, they were all over me hands fingers mouths all over me I started sucking, wanking as one started to eat my pussy, as he ate me I felt his finger go up my ass, I moaned with pleasure, as I did he stopped eating and put his cock against my ass hole as said is he allowed to fuck my ass, I took the cock out my mouth and said to fuck me now. He pushed inside. I felt his friends balls jerk and then his cum hit my throat I savored his cock, the other laid on the bed and I told the guy fucking me to stop a second I straddled him taking his cock in my pussy and then looked at the guy who had been fucking my ass and told him to carry on. Both fucked me I cum so many times, then the guy in my ass cum which made me cum again and I carried on riding untill I fell him jerk and cum in my pussy. We all went in the living room where the guy who come in my mouth lifted me on the table lifting my legs up and fucked both my holes, eventually he cum in my ass, I gave another a blow job as he fingered me and my fb friend held my head with both hands and fucked my mouth. I gave each a kiss and went home

Midsummer story [Maledom]

It’s a Midsummer night. Pale sunlight beams through a cloudless sky. The air is still warm on this nightless night. People are drinking and dancing by the diminishing bonfire. The nature in Northern Finland blooms; willow trees are waving in the wind, building the mystical atmosphere, and the scorching heat of the day has replaced by a calm, fresh air. There’s definitely some magic in the air.

Saana is sitting and watching others, wearing a mysterious smile on her face. The wind makes her white, long summer dress caress her skin softly. She’s still breathing heavily for joining the dancing just a little bit earlier.

Saana is actually kind of anxious to go to bed. There was this ancient saying, that if girl gathers seven different sex toys under her pillow, a partner of her dreams appears. This was a first Midsummer when she surrendered to the superstitious traditions; she carefully picked seven of her favorite toys under her pillow. Even though Saana didn’t believe in the old saying, she still feels her panties getting wet by thinking about her toys. Hell, if that man doesn’t appear, I’m going to play with them myself, she thinks. She wishes everyone a good night and goes straight to her bed. Read more »

The Dog Walkers [FM] [older woman] [outdoor] [anal]

this is my first go at this, let me know if you liked it!

Serena always enjoyed her walks with her sleek Hungarian Wizla, Gideon. She and her husband had spent hours walking him when he was a puppy but now it was mainly her domain. She caught a glimpse of herself reflected in a shop window as she made her way to the local park near their well-appointed house and allowed herself to feel pleased at what she saw. In her late 40s, flame haired and still as sleek and lithe as her walking companion, she was pleased with the effect of pairing fitted leggings and workout top with wellington boots, despite it being a warm spring.

She entered her usual park and let Gideon off the leash; he sprang away from her and found a regular friend of his, a greyhound that was often exercised there by its owner. Serena was pleased to see it too as its owner was a favourite of hers; a young man of around 25 who’s name she’d never quite got. He was dark and handsome, with a slim muscular build and soft eyes. He was quiet and seemed shy around her, not doubt feeling the same sexual tension she enjoyed. Serena was old enough and wise enough to know sexual chemistry when she felt it and it seemed the poor guy didn’t really know where to put his eyes when they met. Read more »