Tag: Anal

18[F] tried anal for first time. he slowly inserted his finger to prep me for his dick, and that made me cum almost instantaneously.

*This happened a few months ago but posting here for the first time*

The feeling was so intense that when he finally got his whole middle finger in, i came in less than a minute. It was an orgasm like none I’d ever felt. Like maybe he was somehow massaging my vagina or g spot from my anal canal.

Next he began trying to enter with his penis. He wasn’t that big but it sure felt like it was too big. We had to use so much lube. Slowly he kept inching in and pulling back out to lather himself with more lube, and massaging some into my butthole as well. I gasped and grunted every time. What an amazing and simultaneously terrifying sensation.

I kept asking if he was all the way in because I felt so stretched, but he kept replying no. I was on all fours doggystyle and watching the action from between my legs. My pussy felt extremely sensitive and i could feel that i was gaping a bit. I was extremely wet and could feel juices flowing down my pussy and ending at my clit. I could see my own strand of grool slowly developing. Read more »

Failed anal sex [F]

Hey everyone
Wanted to tell you guys about my first and only anal sex experience which failed lol. I was always scared of anal sex. But when you’re in love with someone you have your sexual connection at peak with him/her . My bf (zee) asked me if we can have anal sex . I refused to let him do that because I heard that its quite painful.

After asking repeatedly he was successful in convincing me to take his rod in my asshole. Well you guys can say that I agreed to do that out of love and I was not fully ready for the action and funny thing was that I completely forgot about it when we got the opportunity to have fun alone in the room.

So the day we were alone in the room cuddling ,kissing and sucking each other he asked me to remove my tights so he can bang me from behind. I took a pause and he reminded me that I agreed to have anal sex . I was thinking more about my asshole if its clean than the anal pain . Read more »

Like Mother, Like Daughter – Start Her Up – Part 6 – Tying Up Loose Ends [MFF][Deepthroat][Anal]

It didn’t take much convincing to move the girls and their mothers out of their hovel and into our guesthouse. Going from three cramped rooms and a crappy toilet to a six-room house with two bathrooms was an easy sell. I gave Anna strict orders to feed Carina properly and start stretching her asshole. I had a strong urge to assfuck Cassandra’s mom as soon as I could. Anna promised to do her best to have her ready for me within the next two weeks. Anna had her breast augmentation planned for the end of the week so she would have a lot of time to train Carina while she was recovering.

The next couple of days I introduced the girl’s and their mothers to Helen who took them under her wing to introduce them to the company. I explained to Helen how they were critical to secure the next investment round, but being the typical CFO she made sure they all pulled their weight. I told Helen that I needed a couple of weeks to finish up at the university and she agreed as long as I could put in time in the evenings and weekends. Read more »

Powder Brush [F] 19

It began with a zoom call. I was on zoom with two of my best friends, including my friend with benefits whom you may remember from previous stories. We decided to play truth or dare. After a while of avoiding dares and only picking truth we started to loosen up. My friend with benefits dared me to pose for a picture with a powder brush to my ear (be patient as this brush is relevant later).

Shortly there after I gave him a dare to shove something up his ass. He grabbed some astroglide and some vibrating anal beads. Because our other friend was also on the call he only showed his face. As he stuck the the vibrator up his asshole we could see his facial expression change as it went deeper. My other friend and I began laughing, though as I watched him I got wet thinking about his arousal.

I asked him if it was on, he said no, but quickly turned it on, and we could immediately see his face change again. He was clearly getting horny. He then says to us that he’ll be back shortly and turns off his camera and microphone. It’s not secret, however, that he left to cum. Read more »

Have I got a Problem? [MF][MF] [MFM][Oral, anal]

Have I got a problem?

I’m 24 years old, 5’11” tall, 34C breast, 24″ waist and I can lie and say a 34″ butt, which is really more like 36″ or even a bit larger. I have blonde hair and blue eyes, and this is about how I got over a couple of problems.

My first problem was Sean. He is a year older than me, a shade taller, seriously fit, a cross-country runner, black hair with dark eyes. He’s a great guy, a long dick and knows how to use it. I love it, in my mouth, in my pussy or up my ass, I just love it. His attitude is positive, his aroma is just unbelievably sexy and I don’t know why that’s important, but just the smell of him attracted me, right from the start. I was dating, and fucking, Sean for about nine months when I met my second problem, Dylan.

Dylan is also a year older than me, a shade taller, seriously fit, an exercise physiologist, black hair with blue eyes. He’s a great guy, a long dick and knows how to use it. I love it, in my mouth, in my pussy or up my ass, I just love it. His attitude is positive, his aroma is just unbelievably sexy and I don’t know why that’s important, but just the smell of him attracted me, right from the start. Read more »

[MF] In her mouth and then her ass

I had never chatted with a girl as inexperienced as this one. She was almost 22 and had only had one serious boyfriend in the past. It had been almost a year since she had hooked up with anyone. She couldn’t even express how horny she was. She was dying to suck a dick and taste some cum. One of her favourite things to do. She had read some of my other stories and showed an interest in trying anal. She had some plugs and used them every once in a while. She told me how it felt really good but how she wanted to know what it was like to have her ass fucked.

Being a fan of anal this was so exciting for me. We exchanged tons of dirty messages with each other. We shared links to some of our favourite videos and things we wanted to try. This would go on for an excruciating 2 weeks before we finally scheduled a meet up. She was a bit anxious about doing anal the first time we meet. I told her not to worry. If it happens, it happens, and if not we have all the time in the world to try again. Read more »

Good girl turned into freeuse slut – 2

I don’t know what had gotten into me – for days, I was suddenly always horny. I’d have a wet dreams and I would wake up wet and horny – and immediately proceed to obtain my first orgasm of the day. Still sleepy and half-dazed at this sudden animal-like need, I’d lie on my back in bed, furiously rubbing my clit so that I could have the orgasm quickly and go back to sleep.

Fast forward to late morning during work, I’d suddenly be aroused by my own cleavage and I’d unconsciously start playing with my nipples – tugging at them below my shirt, pinching and twisting them. In barely any time at all, the familiar tingling sensation between my legs would be back – my pussy aching to be pleasured. But I wouldn’t just yet. Instead, I’d run off to find a new way to take slutty pictures. And in the process of standing in front of the mirror, taking nudes for hundreds of strangers to see, I’d somehow grow hornier. There’s something about strangers seeing your naked body and knowing that some of them will jerk off to me – oh, what a turn on! Read more »

BUYING MY STEP-SISTER, Pt.6

(Ashlynn lets me go where few have gone before. Someone else enters the picture?)

6

It was tough not to thrust my hips some more and dump my goo in Ashlynn Luker, one of the damn-sexiest pieces of ass I’d ever had, and the fact I was paying for that ass made it somehow even MORE erotic, step-sister be damned!

Ashlynn was not dumb. She knew the deal, knew what was expected, and was OK with it. Ashlyn Luker had long ago decided that it was part of being bought, but even more so she felt safe to do this. As long as Johnathan Roberts (me!) went slow, she felt like it would go OK.

“Ok sweet, I’m going to go slow here,” I said. I slid the ‘mighty mushroom’ down, between those cheeks, and feeling it nudge against that anal ring, I applied just a bit of pressure.

“Oh-Oooooh..” Ashlynn said. Her ass was straight up, but she was bent over, and looking back at me. She nodded encouragingly

With my left hand, I held her left ass cheek, and pulled out just a bit, while the right hand was palm down at the bottom of her spine. Steady but slow, I pushed, and felt her anal ring give. Read more »