Tag: Anal

How I Turned Myself Into A Perfect Sissy Part V [M23/F26/M36] [Anal] [Deep Throat]

*I really advice you to read the previous parts first. They are* [*over there*](https://www.reddit.com/r/dirty_boy96/comments/xuwfq0/how_i_turned_myself_into_a_perfect_sissy/?utm_source=share&utm_medium=web2x&context=3) *and* [*over there*](https://www.reddit.com/r/dirty_boy96/comments/102bdix/how_i_turned_myself_into_a_perfect_sissy_ii/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

Time flies by. Especially when you look back onto your own past from a future point. After my roommate and I had produced our first more than just decent porn video together, the thing really got viral and made us a lot of money, my feminiziation kept on going. I kept on training my voice, I improved my posture, my movement with every week and I was planning of getting myself a nice pair of tits. And maybe some new fuller lips.

But surgeries like that don’t come for free. Or for cheap, when you want to make sure that you get the best, most qualified surgeons that are available. So I needed to make more money. My roommate, well, from that point on more my girlfriend, and I kept on producing content. Content that on average did more than just well. Our audience was growing. Not exploding, but the numbers went upwards not downwards. Read more »

Attracting the Pack sample(18+) [gangbang, noncon, mindbreak, dubcon, anal, spitroast]

*This is just a sample – check out the full piece over on my Patreon!* [*https://www.patreon.com/posts/76855546?pr=true*](https://www.patreon.com/posts/76855546?pr=true)
*~~~*
… She addressed all of them as she spoke with more confidence than she actually possessed, “be gone beasts, this is your only warning!”
The creatures simply laughed. With gritted teeth, Cali backed up only to yelp and leap forward – she had stepped back into the fire! She put out her tail with a few frantic pats – keeping her distracted while the werewolves closed the distance. Then, they pounced. Despite her years of training, nothing could have prepared the warrior for such an unbalanced fight. They overwhelmed her in seconds. No matter how much she fought and struggled, there was little she could do without her weapons. She hated to admit it but she was helpless, outmatched and outnumbered. When she tried to throw wild punches, her hands were swatted away and her arms were wrenched behind her by the crazed wolf. The furious woman was pushed to her knees. She hung her head, already exhausted from her struggles but looked up again to witness what would happen next.
Sher-Rok grabbed her chin with his vaguely human hand. His sharp claws dug into her cheeks, drawing blood. He leaned in so Cali could smell his last kill on his breath. His teeth – white and sharp – were visible as he snarled out a warning, “as much as I love the hunt… You’d be more valuable to the pack intact… so this is your only warning – to behave.”
Cali’s eyes widened before turning dark. Before she could produce a cutting remark, the Alpha was handed a ghastly-looking collar by Ranulf. She fought in the grip of Knives but his firm hold kept her in place on her knees while Sher-Rok collared her. The thing was made of sturdy and heavy metal that weighed her head down slightly. The edges were rough and dug into her neck thanks to the tightness. A chain leash was attached at the front and wrapped around the werewolf’s hand. The humiliation set in thick, especially when the deep dark laughter of the creatures rumbled around her. She felt useless when her chest armour was ripped from her body. Pieces of her shirt also came away – caught in his deadly claws – leaving her still mostly covered but feeling very unprotected.
Cali sneered at the menacing smirks, commanding as much authority as she could before it was completely taken, “What are you bastards going to do to me?!”
Another raucous, tree-shaking laugh. With the firelight behind them, the head wolf looked even more frightening, especially when Cali finally noticed his large canine dick – fully erect – twitching right in front of her face. That was the only answer she needed – if it wasn’t obvious already. Just as she was about to get a cock shoved in her mouth, the young one – Ranulf – stopped his boss, “the bitch has teeth no doubt! Break her before she maims you!”
Bastard! That was her intention! Heeding his underling’s warning Sher-Rok made a change of plan. He used his grip on the leash to pull her muscular but comparatively smaller body forward. Knives quickly bound her hands behind her in thick, coarse rope before retreating. Cali tried to stand up but Sher-Rok rounded on her and pushed her face into the dirt. A strong arm around her hips and her behind was lifted into the air. She shrieked and struggled but it didn’t stop the back of her pants from being ripped open with a swift slice of deadly claws.
As the Alpha, Sher-Rok got the pleasure of claiming her first. He’d be the first but certainly not the last to pump his seed into her. Her rear was exposed but he didn’t want to go for that – not quite yet anyway. He positioned his large cock lower down and with a mighty thrust rammed himself inside Cali’s pussy. She yelped as he forced his way in – far too large for her unprepared and unaroused hole. He rammed into her without restraint. It felt as if her insides were being ripped open to make way for his unnaturally massive shaft. While she cried out in pain he howled in pleasure. The others were cheering him on as their leader used his grip on the woman’s hips to power up his thrusts. His ghastly claws tore at the remaining shreds of her tanned pants, leaving her lower half exposed to the ever-growing night’s chill… Read more »

Dinner and dessert [anal] [spanking] [public] [“sir”] [M22] [F22]

It’s the third course of a formal university dinner on a Thursday evening when you lean across to whisper in my ear. You look gorgeous in that dress with the slit up your thigh to show off your gorgeous legs that look as good strutting down the ancient streets as they do in the air or pinned back behind your ears. I’m trying to compete in a well fitting suit with dress shirt sleeves that you like so much rolled up to the forearm. Your warm full lips pull into a smile as you whisper words into my ear that no one else can hear.

“I douched for you, sir.”

The words send a tingle down my spine that starts under my skull and finishes at my crotch, where I feel the material of my trousers become tight. Fuck. Your eyes flick towards your bag and I see a small container of lube that you brought with you. God you’re so perfect, and clearly have been planning this encounter. You smile is now self-satisfied and your eyes glisten with anticipation. You raise an eyebrow. My eyes meet yours and I convey in my gaze that I understand what you are suggesting. Here. Soon. Read more »

Learning anal [23f] (solo)(first time anal)(innocent)

Rosalind finally made it home and closed the door behind her holding a plastic shopping bag. Her girlfriend had recently managed to convince her to widen her horizons after being with each other for almost a year. Rosalind’s girlfriend was far kinkier than she was and had always wanted a chance to explore Rosalind’s second hole. Rosalind had been hesitant about this but she decided that she would try it as a valentines gift for her girlfriend.

She wanted to make sure she would be ready for her when the day came and following the advice of some online forums she went shopping for some new toys.

In the bag were her new goodies. She bought a few buttplugs ranging from a puny 1 inch diameter one to a far more impressive 3 inch plug. Also in the bag were some pink anal beads, the type with the ring at the end to grab onto, an enema kit and most importantly of all, a big bottle of lube. Read more »

I (25F)got invited to a 3some by my friend with her BF. Now she is mad at me😅 [MFM]

Edit: MFF

Couple of summers back, my friend from college invited me over for a threesome with her bf. They were exploring new things in their relationship and she trusted me as we were close friends. I knew her bf fancied me a bit 😋 and hence, I was hesitant at first so as to not ruin anything. But after her frequent requests, I complied and we had a long weekend planned at the guy’s farmhouse in Delhi.

At his place, we clicked instantly as we already knew each other. Nisha didn’t mind me flirting shamelessly with her guy, even encouraged Dheeraj to get close with me. Dheeraj was a handsome guy, 6ft tall and a bit muscular, checked all my criterias for a good fling😬

Both us girls teased Dheeraj a lot on the first day right from the time we reached the place. Changed to our tiny bikinis for a swim in the pool giving him a good show.
We had chosen our sexiest thongs to wear around the house. Even made out quite a bit infront of him to get him on the edge 😂 Read more »

How I became an escort! [F]

My husband and I got involved in the lifestyle in 1992. After a few months of giving blowjobs to his friends (and later on being fucked by them) we decided to check out a few of the lifestyle clubs and parties in New York. We attended a couple of events, and were generally unimpressed. Met some very nice, open-minded and uninhibited people, but 99% just weren’t what we were looking for.

One guy came up to us at the first party we attended, and we chatted for awhile. His interest was obvious, but my husband politely declined, which is more usual in the lifestyle than you might imagine. He just wasn’t my type.

We saw the same guy at some other clubs/parties, and he always stopped to chat and say he was still very much interested. Always pleasant, never pushy, but definitely tenacious! We started to refer to him as “my biggest fan”, and knew he would approach us at any get-together. He wasn’t desperate – he was a decent looking guy, and we always saw him getting action at these events. Again, just not a match for us. Read more »

Learning The Hard Way (NC, extreme object insertion, forced orgasm)

*Every character in this story is 18+*

Disclaimer: This story is graciously sponsored by Wilson Sporting Goods. **Wilson: Feel it in your guts!**

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“OK, class, now we all know Wilson makes durable products at competitive prices…” Mr. Wessman was holding a standard size Wilson volleyball for the class to see.

One girl in the fourth row did not dare look up from her desk. She couldn’t stomach the sight of it right now; her bowels spasmed painfully just from hearing the quality (yet affordable) brand name.

“Considering it has a diameter of 22 centimeters, can we use Hooke’s law to determine how many volleyballs we can fit in this long modeling balloon? Number 11, you of all people should pay attention to this lesson.”

*The laughter… how can they still find this shit funny after 4 days?* Read more »

Some people do “dry January.” I’m doing all-anal January. Seriously. So far it’s going great. [FM]

At the very end of December, I had to get a little procedure done. Everything’s fine, just precautionary – but while my cervix heals up, I can’t have sex until the end of January. Which is a real bummer. But I asked my doc if anal was still okay, and she said sure! (Obviously I can still give blowjobs too.)

So all this month, my pussy is off-limits, but my ass is going to get a workout.

Now, I’ve always been happy to do anal if my guy requested it. But except for special occasions, most guys want my pussy instead – which, like, they should, right? The guy I’ve been sleeping with for a few months knows he can fuck my ass whenever he wants, but we don’t do it very often. But when I told him that we’d need to stick to anal for the month, he got pretty intrigued.

[Side note: he’s in his 50s and married. If you want to know more about our situation, it’s in my post history.] Read more »

Became someone’s own little whore! [FM]

Like many girls on this sub, I grew up religious. Modest. Covered elbow to ankle. Not allowed to touch a man. Repression breeds perverted sluts. No two ways about it.

By 18 I’d only slept with my high school boyfriend. Nothing special. I pretty much only interacted with people in my cultural and private school communities.

Yet I was obsessed with beautiful, frilly lingerie. Spent my paychecks on Agent Provocateur. Changed with the windows wide open since 16 to give my neighbours a little treat. Bought latex Vivienne Westwood heels.

At 18 I was a size 2, 5 foot 7, runners body with disproportionate F cup tits that were so perky a pencil wouldn’t even stay under them. Narrow, boyish hips. Tanned, big brown eyes, huge lashes. Unique beauty. I always wore skanky look at me outfits, and still do, even though now, at 25, my tits are a little softer, cheeks a little more prominent. I’m a 4 and H loves me more than ever. Read more »

[MF] That time I met an adorable, super chatty, kinda lonely Asian ROTC tomboy, ate her out for the first time, fucked her pussy and ass till she cried, and made her my sex slave for the rest of the summer.

At the tender age of nineteen, Annie had a throat like a goddamned blackhole and she knew how to use it. All the discreet blowjobs performed in the woods at church camp had not exactly transformed her into a dick sucking, but what she lacked in skill, she made up for in raw enthusiasm and the sheer, undisguised delight she took in swallowing my cock.

Combine that with an extreme tolerance for discomfort—nay, a desire for it, so long as it was in service of serving me—and some long summer afternoons would disappear between her lips, as I told her to take my messing shaft in her mouth and to keep sucking until I told her to stop. She could entertain herself for hours like that, teasing me into hardness, gagging on me and allowing me to force her face down until her cute little upturned nose was buried in my pubic hair and the tears dribbled down her flushed cheeks, until I finally rewarded her with a grunt and a thick load of cum, and the cycle would begin anew. Read more »