Tag: Anal

My [M] memories of Squishy [F] – A twitter friend who liked aggressive sex, became a sexting partner and engaged me in multiple IRL trysts. PART 9

[Part 1 (The first nude pics)](https://www.reddit.com/r/gonewildstories/comments/gzy5hc/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 2 (The attraction becomes mutual)](https://www.reddit.com/r/gonewildstories/comments/h01pvo/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 3 (The dirty sexting) ](https://www.reddit.com/r/gonewildstories/comments/h02yz4/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 4 (More dirty sexting; we decide to meet)](https://www.reddit.com/r/gonewildstories/comments/h03cgv/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 5 (Our first meeting: Mouths, tits and perspiration) ](https://www.reddit.com/user/Mrquick83/comments/h03ml7/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 6 (She gets rough. I hold her down and take her)](https://www.reddit.com/r/gonewildstories/comments/h0jbeo/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 7 (Risky sex outdoors)](https://www.reddit.com/r/gonewildstories/comments/h78ifd/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 8 (Angry coercive anal sex) ](https://www.reddit.com/r/gonewildstories/comments/h7zwy1/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

[Part 9 (Sexy surprise in a local store)](https://www.reddit.com/r/gonewildstories/comments/hdj2or/my_m_memories_of_squishy_f_a_twitter_friend_who/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

So, for anyone who just feels like reading an explicit retelling of the time I ass-fucked a cute blonde girl outside of a home furnishings store, scroll down to the paragraph marked with this: ????.
For all the rest of you who want to hear another sexy story about Squishy and I in its full context, well, here it comes.

Alright! So as you know, [Squishy ](https://imgur.com/a/Tfz3qta) and I often met on Saturdays, and the fact that I had a side-hustle buying and selling stuff on eBay provided great cover for the fact that I was away on Saturdays a lot. I didn’t know my wife was banging another man at the time but I sure wish I did, since it would have saved me a ton of unnecessary guilt, but whatever. Read more »

The Sex Tape Part 2

[Part 1 Here](https://www.reddit.com/r/eroticliterature/comments/hcv4j8/the_sex_tape/)

Kiara’s robe dropped, revealing her perfect figure. Her tits were still just as perky nude, her areolas puffy and begging to be sucked. A cute landing strip guided the eye towards her pussy, engorged and lubricated. Liam removed his pants, his cock straining against his boxers. In turn, I removed my own lingerie, revealing my own tits and shaved pussy.

“Wait a second,” said Chris. “There’s four of us. How’s a threesome gonna work?”

“I could manage a foursome,” said Kiara, her voice suddenly deep and husky. “Swap?” she asked me.

“Sure,” I said, and before I knew it she was on her knees in front of my boyfriend, pawing at his cock. Chris looked to me for approval. “Go ahead,” I said.

Liam unveiled his cock before. It was bigger than Chris’s, by a fair amount. Uncircumcised, and hairier than I’m used to, it must have been seven inches at least. The sight of it made me crazy, and I didn’t stop myself kissing the head and swirling my tongue around the shaft as I sucked it. Read more »

My [M19] first time doing [anal] [MF]

Okay so I’m pretty average, 5’6″ curly brown hair and average length dick. I was 18 at the time and the girl I was with, let’s call her C, was 19. C was a bit shorter than me, really nice body with a small belly and really curvy with nice 34DD breasts. C was was from Pakistan and had a nice dark skin tone with long pink hair.

Enough of appearance. C wasn’t exactly a girlfriend, we went on a handful of dates and fucked a lot, that’s basically it (university). It should be worth pointing out that I lost my virginity to C and it was because of this she asked offered me her anal virginity. We’d already introduced butt stuff, she liked her ass ate and loved a finger during sex so we had no qualms. Read more »

[MMF] Game night between best friends develops into a threesome (long, pt. 1)

Hi there!

I’ve been lurking and enjoying this subreddit for quite a while now and there’s one story I always wanted to share in order to give something back. With this quarantine, I finally found the time to sit down and write it all out (like many others have). The story is how about a year ago, one of our usual nights of hanging out and playing videogames with my girlfriend and best friend turned into something much more. It was an unexpected and incredibly fun night which ended up being a bit of a transformative experience for us as a couple, leading to a more adventurous sex life.

This post is going to be super long and have a slow buildup, as I want to detail the story as much as possible, both for your enjoyment and my own archival purposes. It’s also my first ever time writing something like this, so apologies in advance if it doesn’t turn out great!

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**First, some brief descriptions…** Read more »

Niece takes control part 6

I woke up, just before Lara. This was a morning that Stephanie and I would not be able to have a hot morning fuck, since Lara was going away for the weekend, and had taken this Friday off. The idea of creeping over to Stephanie’s room and waking her up for a quickie crossed my mind, I knew that she’d be more than eager to milk out my morning load. Before I could put that idea in motion, I felt Lara stirring. I again feigned sleep, as I had done the other day, hoping I could see her nude again. She did not disappoint, after looking closely at my face, I sensed her drawing back, and watched as she stripped naked, my cock responding accordingly. She headed into the bathroom, and I could hear the shower start up. I waited until I heard the shower stall door open and close, then I scurried over, eased open the door, then slipped inside. There was enough room for me to observe, without being directly in her sight. Read more »

[FM] That time I [18F] gave a 6’7” football star [21M] my anal virginity

I don’t always make the healthiest decisions. Looking back at this one, I wish I could have freeze framed the moment of entry and done a voiceover a la *The Emperor’s New Groove*. “I bet you’re wondering how I ended up here, in a dirty frat house, with a cock slowly pushing its way into my ass for the first time.”

It’s a tale as old as time. High school girl goes to state college football game with her friends during her senior year of high school. Girl “accidentally” bumps into hot football player after the game at the nearby taco place that “just happens” to be where the team always goes after a win. Hot football player asks for girl’s number and then proceeds to booty call her every other weekend for months. Girl comes running every time. Read more »

Tim discovers his step sister’s secret.

It had been a shitty day at school. Eighteen year old Tim Masterson had just gotten home when he heard girlish giggling coming from the other side of the hedge row that screened off the pool area. He stopped to listen, picking up several female voices, although he couldn’t hear what was being said, just the laughter. His curiosity picqued, he quick-stepped down the row and around the corner to the back door of the pool house.

As he entered, he noticed that the French doors that led to the pool were all open. He hurried across the room, which consisted of a seating area around a fireplace, a kitchenette/bar area, and the door to a connected bathroom. Sidling up to the open front doors, he peaked around and immediately got an eyeful.

“Ho-ly-fuck!” he whispered to himself.

Not thirty feet away, his step-sister and two other girls were lounging on pool chairs, all chattering animatedly over each other, all blonde, all topless. Tim’s eyes feasted on three sets of firm, young, naked tits. In addition to Chloe, his 19 year old step-sister, he recognized Madison and Taylor, also 19, two of her fellow cheerleaders at the local college. They were all oiled up and gleaming in the bright sun, their hair in ponytails and sunglasses shading their eyes. Read more »

Chastity Slave’s Story at the half way mark. [MF] or [NBNB]

My partner and I both identify as non-binary, but she is anatomically female and I am anatomically male for detail’s purpose, hence the tags. My partner is also a gray asexual which is somewhat relevant. For her, sex is like a two way back rub, it feels physically good to both parties and she enjoys it, but she could go months without having any sort of sex and it wouldn’t bother her. Since I am such a desperate slut, this is wonderful because to her, a back rub, a foot massage, eating her out, cooking her a delicious meal, or fucking her silly are all in the same realm of physical pleasure. It’s so hot knowing that she gets the same or more pleasure from activities that deny me sexual access.

So to start, my Goddess and I are somewhat new to long term kink play. This is our first session longer than three days and that was a lot less involved than this one. So this story begins back on Sunday. My Goddess works full time but I am currently a student on break so I’ve been home all day while she’s away. I’ve been less productive than I want to be, in part because I usually masturbate multiple times a day. Last Sunday I told her I was planning on being more productive this week and that I wasn’t going to cum until the next weekend. Boy was that a mistake, I have been even less productive this week ?. Read more »

Long Distance Changes Things [Part 2] [MF] [oral] [anal]

[Part 1](https://www.reddit.com/r/eroticliterature/comments/h8ijce/long_distance_changes_things_part_1_mf_peeping/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

You walk back out into the living room, and start flipping through the channels, trying to find something to watch. A few minutes later, you here the bathroom door open and footsteps in the hall. Tanya rounds the corner, wearing nothing but her towel. She makes her way over to the couch and sits down next to you. “So what do you wanna do tonight?” Tanya asks, with what appears to be genuine interest. “*You*” you think, as you struggle to maintain eye contact. “I don’t know, maybe go to Mackey’s?” “Hmmm I don’t know, we just went there last weekend” replies Tanya. “Maybe we could do something new.” “*Did she just wink at me? Did she just lower her towel some?”* you debate with yourself. Next thing you know, Tanya has spun and laid sideways across the couch, head propped on the armrest and legs crossed over your lap. You look over at her, and notice that half of one of her nipples is showing above her towel. “Um, T, your nipple is kind of, um, slipping out a little” you say, hoping that she can’t hear the arousal in your voice. “Oh sorry, let me fix that” she says, right before pulling her towel down. As both of her breasts spill over the towel, your try (fairly unsuccessfully) not to gawk. You almost instantly have a full erection, and she notices. She starts to rub her feet on your crotch, and you place your hands on her thighs to try and stop her. “T, I don’t think we should be-” is all you get out before she cuts you off. “Your hands are cold. Maybe I could help warm them up.” And with that, she uncrosses and spreads her legs, giving you a full view of her pussy. You freeze up again, and can’t look away. Her lips are a perfect shade of pink, and look so warm and inviting. You feel yourself involuntarily lean forward a bit, but catch yourself. Read more »

Yes Daddy! Final (Age Play, MF, Anal)

(comments always welcomed)

Part Five

He pulled his cock from my sopping wet pussy and I felt him slide two fingers inside me. His fingers reignited my passion, a little flame inside my belly that was beginning to burn again.

He slid his wet fingers out of my pussy and drew them upward to where my little pink pucker was. He spread the wetness around and began to massage my little hole.

He repeated this until the area was wet with my pussy juices, then he began to insert one of his fingers into my ass.

I had never done anal before and my ass was a total virgin. I almost went out of character. “No Daddy, please”, I said. “Not that”.

He continued to work his big finger deeper into my ass.

“Oh I’m going to have you Baby Girl”, he said. “You should try to relax”.

“But Daddy, you are so big, and I am so small”, I said, true concern in my voice.

By now his finger was knuckle deep in my ass and he began to slide it back out again.

“That’s what is going to make it so good”, he said. Read more »