Tag: Anal

How I paid for college giving handjobs [F18][Massage]

The door buzzed and none of the girls seemed very interested. A few moments later, the owner’s head appeared in the doorway of the girl’s room.

“Candy, you’re up! Room two.”

“Time to lose your cherry,” Maddie commented as Candace rose to see her first customer.

She walked down the hallway until she reached the tiny room with a number two on the door. She knocked softly and waited.

“Come in!” a boisterous man’s voice responded.

Candace pushed the door and did her best not to react to the very overweight man in his mid-fifties standing completely naked by the side of the padded, wooden massage table. He had a full thick head of salt and pepper hair which seemed to extended from his head all over his bloated, paunchy body.

*Santa Claus?* Candace joked to herself.

“I’m Candy,” she blurted, and extended her hand to shake.

The man made a confused face, not expecting the attractive teenager to make such a formal introduction.

“I’m Rick,” he responded, smiling as he gobbled her up with his eyes. Read more »

College Sexcapades: Part 3, Pegged by college feminist [MF]

College Sexcapades: Part 3, Pegged by college feminist

This is taken from another account I had that I lost the password for

After my fling with Jay we were really close. My other roommate Ross found out I had sex with Jay and she thought it was funny I banged both of them. I hooked up with them throughout the year but never officially dated either, just more of a fwb when I or they hit a dry spell.

One day Jay introduced me to her friend Taylor. Taylor was my height at 5 foot 10 and was a sexy petite redhead. She had tattoos up and down her legs, full arm sleeves and also an under rest tattoo.

The first night I hung around her she gave me her whole life story and how she was a strong feminist. I was raised very conservative but her allure drew me in. I asked Jay about her and she said she was single but was a bit crazy and but a fun time. I could agree. Read more »

Incel gets taught a lesson by trans woman [forced][anal]

I wrote this for a friend, post interaction appreciated 😊

“Get undressed!” I snapped out of it and quickly undressed and stood naked in my basement. The tall, slender woman in dark clothes guffawed and flicked my man-boobs. “Wow, they’re almost bigger than mine!” She laughed and shoved me onto the bed and proceeded to tie me up. 

“Wait, what are you doing?” I yelled. She started climbing on top of me to straddle my face. 

“I told you, your mother hired me to educate you. You’re a sad desperate man with a hatred for beautiful women. And now I’m really going to give you something to hate.” She unzipped her pants and pulled out a cock that wasn’t hard yet and still huge. “First step to treating a woman right was being chivalrous and you already failed. Second step is giving her pleasure. Don’t fuck it up.” She forced my mouth open and then stuffed my mouth with her limp cock. I struggled against the intrusion, but she began thrusting back and forth. She growled down at me in a sarcastic sing-song voice, “You’re fucking it up, bitch boy.” I grimaced and began moving my mouth with her thrusts and tried moving my tongue a bit. Her massive length began to stiffen and I looked up at her for approval. If I did well enough maybe she’d stop.  Read more »

She Begged Me to Help “Find Her Prostate” Because Her Husband Wouldn’t [F/M] [Anal] [Creampie]

I’m a massage therapist for wealthy people in a upscale part of Southern California. As a young straight guy, I can say my job definitely has its highs and lows. The highs are when I get to give oil massages to gorgeous, tan trophy wives.

The lows are when I have to give oil massages to their old, wrinkly husbands. (I’ll spare you my mental images of them.) Highs or lows, I’m a professional and I do a good job every time because that’s why they pay me the big bucks and the work is predictable.

At least … most of the time. Last week I had a *very* unexpected session with one of the trophy wives. We’ll call her Jamie.

Jamie is in her early thirties, and she is easily one of my most beautiful clients. Massage therapists see a lot of bodies, and I know who takes care of theirs. Let’s just say that Jamie’s gym routine has her in peak condition. She has curves in all the right places without any cosmetic surgery and she’s very toned with stunning muscle definition. Read more »

She Begged Me to Help “Find Her Prostate” Because Her Husband Wouldn’t [F/M] [Anal] [Creampie]

I’m a massage therapist for wealthy people in a upscale part of Southern California. As a young straight guy, I can say my job definitely has its highs and lows. The highs are when I get to give oil massages to [gorgeous](https://unsplash.com/collections/1PomjLcNrS8/elegant/1f5cd11e5da1fec31c4636f1550f8c38), [tan](https://unsplash.com/photos/mDgL7-vDDhI) [trophy wives](https://unsplash.com/photos/9lS3O4ODEQE).

The lows are when I have to give oil massages to their old, wrinkly husbands. (I’ll spare you my mental images of them.) Highs or lows, I’m a professional and I do a good job every time because that’s why they pay me the big bucks and the work is predictable.

At least … most of the time. Last week I had a *very* unexpected session with one of the trophy wives. We’ll call her Jamie.

Jamie is in her early thirties, and she is easily one of my most beautiful clients. Massage therapists see a lot of bodies, and I know who takes care of theirs. Let’s just say that Jamie’s gym routine has her in peak condition. She has [curves in all the right places](https://unsplash.com/photos/5UM5hzPjEW0) without any cosmetic surgery and she’s very toned with stunning muscle definition. Read more »

Shopping is a Pleasure [MFF] (Part 3)

[Part 1 Here](https://www.reddit.com/r/gonewildstories/comments/p51xp5/shopping_is_a_pleasure_mff_part_1/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 2 Here](https://www.reddit.com/r/gonewildstories/comments/p64xmp/shopping_is_a_pleasure_mff_part_2/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

When we got the room, Sarah made a beeline for the chair and sat down. Maddison let out an “oooh” as she admired our bedroom. I locked Sarah’s ankles to the chair and handed over her vibrator I had taken out.

“Oh! And Maddie can use the new one you got!” Sarah said in excitement. I showed her that it was already on the dresser, opened and batteries in.

I turned back to Maddison, standing there at the end of the bed, topless but still in her little skirt and striped socks. I don’t know if it was the wine talking or me but the next thing I said was “Take off your panties and give them to me.” I saw a tremble ripple through her whole body.

“Yes, sir,” she said. She brought her knees together, reached underneath her skirt, and slid a pair of black lace panties down her thighs to the top of her striped socks where they fell the rest of the way. She gingerly stepped out of them and stood, handing them to me obediently. They were completely soaked through. I put them in the pocket of my shorts and walked around to the side of bed that Sarah’s chair was on. I undid the button of my shorts, dropping them to the floor and kicking them aside. Read more »

Rimming His Stallion Doughnut [M/M, stallion anthros, rimming, anal, light dom/sub, erotica] (AmethystMare)

Rimming a stallion’s tight hole is a pleasure best shared between studs…

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As always, I am open for commissions starting at 30 GBP per 1,000 words – please e-mail arianmabe[at]gmail.com for more information or see my profile!

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“Unff… Oh, yes, Terry… Terr… Just like that… Oh, fuck, that feels so good!”

The black stallion laid with his legs kicked up while his boyfriend went to town on his pony doughnut, the thick round of his tail hole under his tail. With his legs hitched up as far towards his head as he could, Reece was in the perfect position to feel every centimetre of Terry’s tongue sweeping inside him, the chestnut stallion with the white, white blaze slurping away as if he didn’t have a care in the world. Maybe, for him, that was true.

Terry didn’t care for much, only pleasure, the stallion a little slow in mind but quick on pleasure, his cock throbbing to attention while he pleased his partner. He lapped up deeply with the thick, fleshy expanse of his tongue into Reece’s tail hole, the skin of his pucker a lighter shade of his coat, showing the grey of his skin. Nickering throatily, the black stallion squirmed, panting heavily through flared nostrils, striving to grab what breaths he could. Read more »

[M]y first experience with another [M]an who also happened to be twice my age

First of all thank you for the great respond to my first post, which you can find [here](https://www.reddit.com/r/gonewildstories/comments/oeomo0/i_24_m_gave_in_to_my_bi_side_and_gave_my_friend/?utm_medium=android_app&utm_source=share)

I got a couple of requests for me to write the story of my first experience with another man so here goes. Again it might be a bit of a long read so skip to “good stuff start here” if that’s what you are here for.

Back when I was younger and a lot less experienced sexually I never thought I would crave another man’s cock in any way. I had plenty of crushes on girls in my school and a couple of girlfriends throughout my early teens. I started jerking of like any normal young hormonal teenage boy and watched normal straight or lesbian porn. Eventually I started to feel slightly different however. I think it started with the fact that lesbian porn was no longer quite as thrilling as it had been. I started watching more porn with big dicks, threesomes with two guys and eventually gangbangs. I started watching only girls doing anal because it felt dirty and forbidden at the time (this was a couple of years ago before anal was so standardized as it is today). Read more »

My Dad’s Cleaning Lady and I Made a Huge Mess (Part 2) [M/F] [Milf] [Free Use] [Oral] [Anal]

It was 9:56 on Wednesday. I’d been checking my phone obsessively for the past hour. It was only four minutes until Brenda was scheduled to get to the house. And I’m not going to lie, I had already changed my boxers once because I was already leaking precum.

It had been a week since I had fucked her in the bathroom. Seven full days since we’d first discussed our new arrangement. 168 hours since she had let me do whatever I wanted with her tight pussy. And now I was a just few minutes away from exploring her body again.

9:58. I had jerked off in the shower probably a dozen times since last Wednesday. Technically it was a dozen times between Wednesday and Sunday. I had been saving my cum for her since Monday, and my balls felt completely full.

There were moments when I questioned whether my dedication would pay off. What if she had reconsidered our free use agreement since last week? What if I was full of cum and she showed up only to say that we should go back to the way things were. But then I would remember how she looked at me in the mirror and the worries would melt away. Read more »

[MF] a change of plans leads to some fantastic anal

This weekend the rain in my area cancelled my plans to go hiking, so I spent Saturday morning lounging around in my sweats and getting proper stoned while scrolling Reddit and Tinder.

About two weeks ago I matched with Emily. She’s 32, about 5’6”, slim, maybe 100 lbs, B cup tits and a fantastic ass, and is mixed black and Vietnamese. I’m white, 6’, 185 lbs, 6.5” cut. We’ve been trading pics and chatting quite a bit but haven’t been able to meet due to our work schedules.

I let her know about my change of plans and she just so happened to be free for the day. I rolled a couple of blunts as she made her way over. I met her at the door, me in a t-shirt and some grey sweats, no underwear. She was in a pale blue sundress under her raincoat with her hair in 2 braids. We kissed against the closed door, her hand found it’s way to my cock and she started rubbing me through my sweats. I started to lift the hem of her dress and she batted my hand away, and said that she brought a surprise for me but I had to wait for it. Read more »