Anal Archives — Page 88 of 957 — NSFW story

[FM] Surprise first time anal sex

Back in my freshman year of college, I had quite the times with my girlfriends on the weekends. We loved getting drunk with each other and then using our fake IDs to get into the bars.

One evening, we all got drunk, hopped in the Uber, and headed downtown. Our usual MO was to just drink and dance together until we were all ready to go home. But this night though, we had a fun little game in mind. We wanted to see who could get the most guys to buy them a drink.

So, after flirting with a few guys, getting a drink and dancing some more, I ended up talking to this one tall strong man. He was at least a foot taller than me and more than twice my size. He definitely was attractive and I found our conversation quite fun.

Before I knew it, we were dancing together and all over each other. Before I could oppose, he was calling an Uber and pulling me towards the door. Outside the bar, he pushed me up against the wall and began kissing my neck. I could feel my pussy start to leak down my leg a little. He knew exactly how to kiss a girl right. Read more »

A trip to the farm part 5 [Group] [Anal]

A few days went by and my pussy was completely healed and I was feeling horny as fuck. Last night in the shower, I used the spray nozzle to shoot a hard stream on water at my clit as I rubbed my sensitive nipples. I orgasmed so hard that I almost fell in the tub. I feel like I’ve become completely obsessed with this new lifestyle that Lisa introduced me to. Other than my time alone in the shower, it’s been a few days since my encounter with Debbie in the barn. Today is the annual yearling auction on the farm. Lisa counts on the auction every year to pay expenses.
I went down to breakfast today and was surprised to see Debbie at the table with Lisa. “Good, you are up. Join us at the table”, said Lisa. “Today is very important for my farm and for your individual training”. Debbie and I looked at each other realizing for first time that we have both been training in sexual satisfaction. “That is correct girls, you both have been prepped for this day. Amy, when your mom and I turned 18, our aunt and uncle owned this farm and they trained us the same way you were. In the two bags are the clothes I want you to wear to the auction. The buyers come here from all over the district not only to buy horses, but to pay a premium price for favored services. ” I suddenly felt cheap and used but I also feel my pussy beginning to tingle at the thought. “Don’t worry, you will be paid a years tuition for your time and in top of that, you will enjoy it. I know your mom and I did the 3 years we worked the auction. ”
We took our bags and went to change clothes. My outfit was a tank top that barely covered my large tits, a g-string, and very tight shorts that outlined my pussy for display. My phone rang and it was mom. “Hello baby. I know you probably hate me but you will have the time of your life today. I promise. ” “Mom! I have a hard time believing all of this but I don’t hate you. We will have a lot to discuss when I come home, ” and we hung up.
Several trucks arrived with all of the buyers. At the appointed time, I made my way to the coral and started to mingle. I felt eyes and a couple of hands on me every where. There were more that one husband and wife couples smiling at me and making small talk. The auction went very well. After the last yearling was sold, Lisa announced that the after sale party was set to begin in the barn for tho that had paid for the special services. Several loaded their trailers and left the farm but several trailers remained. I went to the barn and met Debbie up front. There was a couple of beds set up to the sides. Lisa announced that folks can disrobe in the rooms to the side of they choose and then join the party at the beds. Only rules were that there will be no violence and if any harmful abuse happens, the party is over. I made my way to a bed where I sat on the side. Two couples came out naked first. The women were older but still pretty and the men were already hard. They quickly removed my clothes while the ladies played with my tits and the men rubbed my pussy and my ass. One of the ladies straddled my face and rubbed her hairy pussy on my mouth. She was already soaked as I began licking her. The other lady began licking my clit and fingering my wet pussy. After a few minutes, a man replaced her and shoved his hard cock into my pussy. The lady left my face and a cock was shoved into my mouth. I was getting fucked in both holes as I saw the two ladies in 69 position next to me eating each other’s pussy. After a few minutes the men swapped positions and I tasted my pussy of his cock as the other man fucked me hard. In a minute, the cock shot cum down my throat almost gagging me when he did. The other cock pulled out and was shoved in my mouth for a second load.
This went on with two other men until they both came all over me. I could hear Debbie getting pounded in the other bed. We both were cumming over and over. The next man came over and with a wicked smile told me he paid extra for something special. He flipped me on my stomach and I could feel my ass being rubbed with lube. I began to protest but another cock shoved into my mouth stopping me. One lubed, I felt his rough fingers penetrate my ass hole. He fucked my ass with his fingers for a few minutes and then positioned his hard cock. He shoved his cock into my tight ass as I screamed into the cock in my mouth. I felt someone begging to rub my pussy as my ass was being pounded. The cock erupted in my mouth as I was cumming from the sensation at my pussy. My ass began to relax and after several minutes I felt a load of hot cum deep in my bowels.
I lost count of the number of men and women who used me and I lost count of my number of orgasms. After they left, I fell asleep covered in cum and pussy juice.

[M]y girl[f]riend and my jerk off bud. Part 7: Plot twist, the end.

The next day, Brandon had to be at work at 10am. I woke up when he slammed the door behind him as he left. Kirsten was out cold and didn’t stir at all when I rolled her off of me so I could get out of bed. Brandon had retired to his room with the remainder of the tequila immediately after the big event, leaving me and Kirsten to sleep in the massive wet spot. She and I didn’t talk much immediately afterwards, but did a lot of cuddling and canoodling until we fell asleep in each other’s arms.

I took a shower, and cleaned the apartment until Kirsten came limping out of the bedroom around 1pm. Her vagina was, in her words, “fucking wrecked” and she sent me to the store to buy some cranberry juice. All she wanted to do was cuddle on the couch in a T shirt and panties, watching movies and smoking weed. She was extremely affectionate all afternoon, and whined whenever I reminded her I needed to leave for work eventually. She gave me head, said she’d let me fuck her in the ass if I called in. So, yeah I called into work that day. Read more »

The Office Boss [22F/38M] [Noncon] [Age Gap] [Humiliation]

*All characters are over the age of 18*

*This is The Book of Florence Volume II: The Office Boss. If you liked this, please consider checking out the full series on GumRoad or Amazon Kindle.*

I had started a new position as Secretary to the CEO of a prestigious financial company and was excited to receive my welcome email. But the instructions said I needed to wear the uniform they sent me. I held up the sheer white blouse and tight pencil skirt, confused.

My grades from high school hadn’t been great and I had barely passed college – despite letting Mr. Miller take my regular and anal virginity, I had still just managed to scrape by. My parents always said I made up for what I lacked in academics with buckets of enthusiasm and I guess they were right. In the job interview, I felt sure I had mucked up every question but my eagerness to do a good job must have come through. That, and the look the CEO gave me was the same as Mr. Miller. I briefly wondered if I should worry about that but quickly put it aside; this was a fresh start and I didn’t want to get on anyone’s bad side by making assumptions. Read more »

I allowed a friend’s boyfriend to fuck my ass [23F] [25M] [F/M] [Anal] [Creampie]

I had a friend who was likewise somewhat slutty. Talking about sex, what we were into, recent fucks, things we didn’t like in bed, etc. was a big part of our friendship. She had been in an open, long-term relationship with a man. They had mutually agreed that it was acceptable to fuck others, and it appeared that their agreement was working out well for them.

I was chatting with her boyfriend when he said that she never allowed him to fuck her ass. I made the (mainly kidding) offer to him that if he ever genuinely wanted to take some girl’s ass, he should hmu and I’d do it because I knew their relationship was open.

A few weeks later, he texted me to see if I was free and if he could come over. I nodded in agreement, and approximately 30 minutes later we were both in my kitchen. After a brief period of small talk, he asked me if I was serious when I said earlier that I would let him fuck me. Read more »

[M]ake me [f]eel 20 again. Student vs college professor kinky anal![pics], [gifs]

Gather round fam, I got a story that will rock your boat. The following account is 100% legit, (got grainy pics/gifs to share don’t worry) and it is one of those wild, “get outa here” stories that alphas brag about (classic betta here, but miracles DO HAPPEN).

A few things about me. I am 40+, athletic, charming, easy to the eyes, talker, super brainiac college professor (phd and all). My ratemyprofessors page has the chilly meter to the max, and the comments, ooohh the comments, if I ever feel down that’s my go to place. I am a typical “clean professor type” by day, and sexual deviant by night (a look at my browser history can turn nuns to college girls during spring break).

In the past I have had lots of experiences that I could write about, and I also had a story up here (A for awesome) but I had to take it down, for … reasons! I hope this story doesn’t get me in trouble but it is too good not to share. Read more »

[FM] How I’m being trained to love anal (it’s working)

I love a good tongue or tease with a finger but I’ve never truly been into anal all the way. He has taken a big interest recently especially since I’ve relaxed into a tongue more than ever. With a previous partner, like most guys do, he rushed into it and made it painful/unenjoyable. With my current, he’s very open with communication and listening to what I want.

One of my favorite things is laying on my stomach with a vibrator on my clit, with my legs spread, while he uses his tongue on my ass. I cum super hard from it but I definitely need the clit stimulation. The other day he was doing this for 15-20 minutes non stop, enjoying every minute and it was actually quite intimate. We both discussed after and decided we want to continue exploring so I can overcome the bad experience I had prior.
3-5 times a day now he randomly rips my pants down, pushes me up against a wall/counter/bed, aggressively spreads me open and orders me to spread my legs, and then goes to town with his tongue all over my ass. I’ve never felt more vulnerable and every time I feel his tongue graze me and enter me, it flips a switch inside of me. The kicker is that he enthusiastically teases and plays with me until I’m begging for more, and the moment he realizes I want it, he stands me up, pulls my pants up and pretends like nothing happened. It’s the biggest tease and it’s slowly training me to want my ass played with more and more. Read more »

A rough night in NYC [MF] [BDSM] [CNC]

This happened three years ago. I was seeing Emily. We were both 23 and pretty kinky. We had played a lot and she confessed one day to wanting to try CNC play. We negotiated a scene where I would “break” into her apartment and then force her against her will.

We put a pin on a cold Saturday in December. She didn’t know the exact time. She just knew I’d show up at some point during the day. I walked to her UWS apartment around 4 pm, just as the sun was starting to go down. I used her key to enter her apartment building and rode the elevator up to her floor, excited to use her and with a bag of toys in my hand.

I quietly opened her door and let myself in. I didn’t see her anywhere in her apartment and then crept into her bedroom, where she was napping of all things.

I took a minute to admire Emily’s body. She was 6’1, a few inches taller than me and so thin. Her breasts were very small and hidden by the t shirt she was wearing. Her legs were wrapped in a pair of yoga pants that cling to every curve. I sat on the bed and she woke up, and the looked at me, realizing what was happening. Read more »

Nicky and his sister [pegging] [chastity] [ffm]

In a world where all males are required to be locked in chastity at all times, Nicky’s mother torments him inside of his tiny cage, while his sister and her girlfriend help him, blow off some steam.

Nicky looked desperately around his room. Searching for any flaw with his room, his bed was made, shelves were cleaned, floor swept. Everything seemed to be in perfect order. He breathed a sigh of relief when he thought that Nicky looked desperately around his room. Searching for any flaw with his room, his bed was made, shelves were cleaned, floor swept. Everything seemed to be in perfect order. He breathed a sigh of relief when he thought that today might be the day that his mother finally let him out of his cock cage again. It had been such a long time since that shiny key had been anywhere near his cramped cock and sore balls. He sat on the edge of the bed, naked his caged cock on full display waiting for his mother’s inspection. Read more »