Tag: Anal

My [F]irst anal after four years of trying.

[F20+] my daddy has been trying to get in my ass for years but his girth makes it almost impossible even if he warms me up good.

Last weekend he had enough and said that the time has come. He was going to fuck my ass, period!

I got ready in the shower while he was on the way. When i came in he had bought a pink anal dildo to warm me up with. I askes if he atleast bought lube.

Daddy pulls out a fucking bucket of CRISCO?! I burst out in laughter but he was dead serious.

But, we have a free use agreement so i do what im told.

He began with kissing me and felt my body up before licking and fingering me until i came so that i would loosen up a bit.

He then put on some latex gloves, opened that damn can of crisco before he starts to work a single finger in my ass, yes im that tight.

He worked up to two fingers before he started to pry in that pink dildo. It barely fit and all i was thinking was how in hell he was going to fit his dick in there. Read more »

I fucked my friend’s boyfriend (M36/F34) (Anal)

Beth and I had been friends for at least five years and she had been dating Chase for around six months. While at lunch with Beth and Chase, I mentioned that I really needed a good deep tissue massage. Beth immediately volunteered Chase. She said he has been working as a massage therapist for a few years and has great reviews. I viewed his website and reviews and he seemed legit. Chase even said he would come to my place so we scheduled the deep tissue massage for the next Wednesday at 7pm.
That Wednesday Chase arrived promptly. He was dressed in black slacks and a white button up shirt. He had green eyes, sandy blonde hair, was about 6’1, and medium build. He had me undress and lay on the side of my bed with a light blanket over me. He lit candles and played a nice relaxing Playlist.
The massage was going amazing. He oiled my body and worked out tons of knots in my upper back. Then he made his way to my lower body. By this point I was so relaxed I was almost half awake. His hands felt strong as he massaged my legs. He began to massage my upper thighs and I could feel the lightest touch of his finger graze the lip of my pussy. I didn’t think it was intentional and felt immediately ashamed at how aroused I felt. It had been 8 months since I had any type of sexual touch and I couldn’t stop the inside of my pussy from getting wet. He repeated this for awhile, moving from one side to the other. He began to massage my ass and it was only then that I realized the blanket was no longer covering me. He gently stretched my cheeks apart and began to massage the back of my vulva. I knew I should tell him to stop but it felt amazing. He stopped rubbing my ass and I could feel him straddle me and lean into my ear, “You are extremely tense. Just trust me, we are going to release some of it ok?”
“Ok” I whispered
“Do you want me to go light with what’s next or stick with the deep tissue?” He asked in a deep whisper..
He slowly and gently began to rub my vulva with his hand and his middle finger found my clit.
“Oohh” I moaned quietly.
“Gentle or deep?” He asked again as his my wetness began to drip out of me and onto his hand and fingers.
“Deeeep” I groaned.
With that he spread my legs and entered my pussy with two fingers. He filled me until he was knuckle deep and roughly pressed into my walls. I couldn’t stop myself from grinding into him.
He fucked me hard with his fingers and I could feel myself ready to cum when he slid his thumb into my ass. He slowly slid it in and out and as his fingers pressed into the walls of my soaking wet pussy and his thumb went as far into my ass as it could I came.
“Ohhh. Ohhh. Fuck. Ohhh fuuuckk” I moaned as my body shoke from the orgasm. He pulled his fingers out of me and turned me over. He sat in the middle of the bed with his cock out. He guided me onto his lap and I began riding him, both us sitting up. I leaned back and slid my pussy up and down his cock. I watched him watching his cock move in and out of me. He played with my tits and nipples as I kept all of his cock buried in my pussy and grinded him.
He slid his finger back in my ass and pulled me into him.
“You like when I play with your ass?” He asked as he grabbed a fist full of hair and yanked my head back.
“Ohhh yes. Don’t stop” I moaned.
“Ride my dick with your ass.”
I pulled his cock out of my pussy and slowly let him enter my ass. As the head of his cock made way I could feel him stretch me. It hurt but I didn’t stop. We stayed slow until he began to glide more easily in and out of my ass.
“God damn” he groaned as I increased my pace.
Then he grabbed my hips and I wrapped my arms around him as he began pounding my ass. He held my body in place as he rammed himself in and out of me.
I dug my nails into his back and was in between moaning and screaming when I started to cum again.
“Ohhh yes pound my ass. Oh God don’t stop Chase. Fuuuuuck. I’m cumming. Chase I’m cumming. Ohhhh. Ohhhh.” He slammed himself into me one last time and held himself in me as he loaded my asshole full of his thick hot cum. I climbed off of him and we began to get dressed. “We need to keep that tension under control. I’ll see you next week.”

Haven’t Had Any Complaints

My dick is nothing extraordinary. It’s slightly above average length, quite girthy, but besides that, it just looks nice. It’s smooth, proportionate, has some nice veins popping out, with a big, meaty head resting on top of a thick shaft. I’m not a bad looking guy, myself. I’m tall, handsome, have a nice smile, and a sexy voice. I get almost as many compliments on my eyes as I do my dick. Girls like me anyway, so when they find out I’m packing, they almost lose their minds.

I first noticed a change when I was going through puberty, at about 12 years old. I woke up one morning and walked past the mirror naked, caught a glimpse, and had to stop for a second. What had previously been nothing more than, let’s say, a button down there, had now taken on the shape of a duffel bag (that’s the first thing I thought of, anyway) and was hanging down over my balls. This was back in the ’90s, so internet was fairly new. I hadn’t seen a lot of porno, and the stuff I did see was just naked girls, so I didn’t have much to compare it to. In any case, I was pleased with the development. Read more »

The Masturbation Do-Over [MF]

The last time I saw Lynn, she was masturbating to a photo. A photo of me.

We were in college and worked together on the student newspaper. I often went to the office late at night when no one was around to get some work done.

On this particular night, the door was slightly ajar, so I quietly peeked in just in case someone was robbing us. Nothing like that. In a chair in front of a computer was Lynn. Leaning back in nothing but a long white t-shirt, masturbating to a photo of me on the screen. It was just a candid photo. Not risqué or anything. I had never seen a woman masturbate, let alone to me so this was incredibly sexy for so many reasons. To say I was aroused would be an understatement, especially judging by the now massive bulge in my pants.

Now you’d think a college guy standing there all nice and hard would have made my presence known and this story would turn out like the hottest letter to Penthouse Forum.

Nope. Didn’t happen. And it was all my fault.

I came.

Yep. Right there. Read more »

What sex toys I have in my secret locker [F]

So. I am 33 years old, married, work as a flight attendant, and I have a very active sex life and of course I have a secret drawer at home with sex toys. Every man and couple has such a box, right? My box and is in the dressing room at the very bottom. So here’s what I have inside.

Anal and vaginal lubricant. A pack of condoms just in case. Although I don’t use condoms, and I should check to see if this pack has already expired lol.

Four different sized anal plugs. One of the them is my wedding one. Yes I had an anal plug during the wedding because I knew for sure that on the night everything had to be ready. One black silicone plug is a huge one. I use it if I know the sex is going to be hard and I need to stretch me well.

Three different sized dildos. The smaller one I use sometimes for the double penetration effect. One of the toys is a very accurate anatomical replica of a penis. When I saw it I was amazed at how skillfully it was made. By the way, I taught one of my friends how to give a blowjob on it. Will tell this story later. Read more »

[MF] I wanted to get a good night’s sleep, but instead we finally figured out how to love anal

My wife Rachel and I have been together for nearly 15 years, and our sex life has never stopped being adventurous. But even though we both thought it was hot, for whatever reason, anal never worked.

It certainly wasn’t for lack of trying. We read up on it, used toys, did lots of lubing and preparation, started off with hot baths and massages with scented oils, everything. It wasn’t the dynamic that didn’t work; we both were into the taboo nature and it played into our power exchange relationship. Dirty talk aside though, when it came to the act itself she couldn’t enjoy it. For Rachel it hurt, burned, and stung unpleasantly no matter what angle we tried or how much prep we did. Shortly after college, we mostly gave up.

Fast forward 10 years. We’ve gotten married, are now both over thirty, and not to put too fine a point on it, are both workaholics. So when we fall into bed on weeknights it’s usually for exhausted sleep. But not tonight.

Tonight, my wife is so horny that she can’t sleep. [I should have known](https://www.reddit.com/r/gonewildstories/comments/v8o575/mf_the_many_different_ways_to_make_a_mess_on_her/). It’s that time of the month and two days in the cramps stop and the horniness begins. Read more »

Flirting with the Devil – [M/32] [F/27] [BDSM] [Anal] [CnC][D/s] [Forced] [Spanking/Pain/Torture/Rough]

*****To be on the safe and overly cautious side, if you have triggers of any kind, please do not read my content.*****

​

I have finally had it. Everything is unsatisfying. I have been the good girl my whole life and after spending the last five years at the bank working my way up, being polite, wearing my nice pencil skirts and blouses, I have officially had it. I had nearly straight A’s in college and barely knew what the definition of a frat party was. Then I got my job at the bank and being little Miss Perfect just continued. Everything about me and my life is typical, predictable, mundane, boring, and more than vanilla.
Get a tattoo? Nope, Cassandra would never do that.

Show up to work hungover after a Thursday night happy hour that lasted too long. Never.
Have sex on the first date. Not Cassandra.

I don’t know what happened, but I can’t live like this anymore. My life isn’t fulfilling, not even something I look forward to anymore. Granted, I can’t just quit my job at the bank, but outside of those 40 hours a week, I have to find something else to do with my time. Something exciting. Find a passion about something. Anything but continuing on the road I am on. Read more »

Slut Wife on Business trip Part 01

Oh, I shouldn’t be doing this….but here I was, naked, kneeling in a hotel room with a guy I had just met an hour ago, staring at his 9-inch dick, rock hard and ready for sucking.

I was supposed to be a happily married wife, traveling for her job, and letting my fingers and my vibrator get me off when I was all alone in a hotel room. But the rising tide of forbidden lust spreading through my body as I got ready to smash my wedding vows, just made me hotter.

He had sat next to me at the hotel bar, and we chatted for a while. I had told him that I was a married woman, and at the time he seemed to accept that fact. He had offered to walk me to my hotel room door. Once in the elevator, he pressed the button for the 8th floor and pushed the button for the 10th floor when he asked what floor was I on. Halfway up, he hit the STOP button. He spun me around to face him. Read more »

Outdoor Birthday Banger [MF]

So this happened to me 9 years ago. I had been seeing this woman who had been in college across the state (we’d visit each other back and forth). My birthday is at the beginning of June, usually a month after finals are over and everybody heads home.

Well I bet her that she’d break first and would initiate sex before I did when she came back. She took me on it, asking what I wanted in return. I told her if I won, we try anal, to which she agreed. Her counter was if she won, I had to make time every day for a week to eat her pussy with no return gratification. I was cool with it. Rules were simple, no penetration of any kind, no orgasms, we weren’t allowed to masturbate, but we could tease each other.

She tried her hardest, nibbles on my ear, taking me for a walk down a new trail in town and giving me a lap dance on a bench with a scenic view. She purchased a set of butt plugs, deciding to practice in case I won, but also used it to tease me into breaking. She wouldn’t properly masturbate, only enough to get the plugs in. She’d leave one in during dates, run of to the bathroom to take a picture, and then send it to me. Read more »

[M][fiction/fantasy]My girlfriend is turning me into a sissy cuckhold.

My girlfriend and I have been together for about 5 years. About a year ago, the sex got pretty vanilla. It seemed neither of us were really into it. She suggested we spice things up a little, and recently she’s began incorporating toys and lingerie.

It started with my going down on her using a dildo or vibrator. Then she started using some anal plugs (on herself). This helped the sex life, but she kept wanting more. There was some voyeur stuff, she posted some risqué photos online. But about a month ago it took quite a turn.

She bought a chastity cage for me. She said she just wanted to tease me a little, and would take it off after foreplay. So she locked me up, then made me go down on her. Use her dildo on her, and I brought her to right before orgasm, and, as promised, she unlocked me and we fucked. It was fun, but her attitude when I was locked and pleasing her had me a little worried. Read more »