My [F]irst time trying anal. [FM]

Links to previous stories:

– [My first experience with Tinder. [FM]](https://www.reddit.com/r/gonewildstories/comments/cy7h6f/my_first_experience_with_tinder_fm/)

– [My First time deepthroating. [F/M]](https://www.reddit.com/r/gonewildstories/comments/cyccgy/my_first_time_deepthroating_fm/)

– [My First time getting creampied. [F/M]](https://www.reddit.com/r/gonewildstories/comments/cz2odi/my_first_time_deepthroating_fm/)

—

So the party life continued. Drunk Friday and Saturday nights, hangover Sundays, and back to classes on Monday. I won’t lie it started to wear me out a little bit, and I needed a break from going out for a weekend to just recuperate. I spent all of Friday night in bed watching TV shows and movies. On Saturday evening I got a bit horny and thought that Masturbating would help, and it did, but not too much. It had been a week since I had a dick inside of me, and I needed one now.

I opened up my good old friend, Tinder. I messaged one of the guys I had met before who lived in the same dormitory complex as me, and asked if he was busy. He replied that he wasn’t, and I told him to come over and that I was horny. He said he will be over 30 minutes and to leave the door open.

I got excited, and got my dildo out. I got a little horny and started to wonder what anal was like. I had guys finger my ass before, but I was always too chicken to get fucked. Luckily I had a small dildo and a buttplug, so I quickly lubed myself up and practiced. First I slipped a finger in there, but it was weird putting a finger in my own ass, so I changed to the buttplug. I slipped it in with no problem at all and with no pain, so I moved to the dildo. It was only small, maybe 4 inches, so it was perfect to make that next step up. I slowly entered it. There was a little stinging as it stretched me, but after that it was fine. I slowly pushed it further and further until it was most of the way in. The feeling was so weird. It hurt a little bit, but it wasn’t the kind of pain that made me want to stop. It was kind of like poking a bruise. It hurts, but you keep poking it anyway? Idk, maybe that is just me and I’m just weird lol. Anyway, I progress to moving it in and out of me slowly, and I eventually get the hang of the way it feels. It actually really scary because on it’s way out it feels like I’m going to poop, but I don’t. It’s like a phantom poop.

I continued for a few more minutes, but my fuck for the night was close to arriving. I dried my ass and put down my dildo and got in to bed. I heard him come through the front door, and I shouted that I was here. He came in and said hi. As he came in to view of the bed, I scooched over to the side to allow him room, and lifted back the blankets a little to get him to come in. He lay down next to me and went to wrap his hand around my stomach, but noticed that I was naked. He started to kiss me and caress my tits. He notices the dildo on the floor.

“Want me to use it on you?, he said.

“Sure”, I said as I smiled and nodded.

He leant over and picked it up, and used his other hand to find my pussy. He noticed how I was already wet and made some remark how I was gagging for it – which to be fair wasn’t entirely inaccurate.

He took the dildo and rubbed my pussy with it, teasing me and making me moan. He slips the whole dildo in to me at once without warning and I let out a loud moan. He slowly works it in and out of me, gradually picking up the pace. I grab his hard cock through his shorts and tell him to take them off. He obliges. I have to use lube with him because he is circumcised, which is really rare in the UK. I lube him up and begin working his shaft.

After a few minutes my back starts to ache as I am in an awkward position. I tell him to stop so that I can sit up. I’m at the perfect height for a blowjob, so I take his dick and swallow it whole. He puts the dildo down on the bed and tell me to use it on myself, which I happily do. After a few minutes he tells me he is close and to stop as he doesn’t want to blow his load yet. He pushes me on to my back and puts his head between my legs, and begins flicking my clit with his tongue while he fingers me. I love when guys do this. I love just being able to sit back and relax and take it all rather than doing any of the work. I know it’s lazy, but oh well, everyone loves it :P.

He flips me over on to my stomach and tells me to bend over. He circles his hard cock around the entrace to my pussy and pushes in. I really love the first moment when someone enters me, it’s amazing. He pushes in to me until his dick is completely inside of me, and begins to fuck me. Doggy is one of my favourite positions recently, I think it because it makes me more exposed and gives them a better view of me.

“You know how I said I didn’t want to do anal?”, I asked him.

“Yeah what about it?”

“We can do it now if you want.”

He immediately perked up with excitement.

“Really?!”

“Yeah, just go slow at first, I’ve never done it before.”

He takes his cock out of my pussy and grabs the lube, squirting copious amounts on my ass. He slips a finger in there for good measure just to make sure I’m all lubed up. He places his cock on to my asshole.

“I’m ready”, I said, “but go in slow”.

He slowly pushed in to me with just his head. It felt so much different than my dildo, likely because of the size difference. He was probably about twice as thick as my dildo. He kept pushing in slowly, and eventually I got to painful part. I let out a few ooh’s and ahh’s, all the while he is being polite as fuck and asking me if I wanted to stop. I tell him to keep going. This is just the pain I felt when I practised, so it will subside eventually. After a good 30 seconds of slowly pushing in to me he has his cock the whole way in. It feels so much deeper than my pussy for some reason, though maybe that’s just due to inexperience with this new feeling.

He begins to pull out slowly again.

“Okay I think I’m okay now”, I said, “lets try it”.

He didn’t need a second invitation. He pushed in to me, quicker this time, and starts to thrust in and out of me slowly. With each thrust in to me the pain lessens. He starts to grunt as he fucks me, and picks up the pace. He pushes me down flat on to my belly, and keep fucking me while pulling apart my cheeks for a better view. He begins to fuck me harder and harder, his animalistic instincts taking over now, as politeness goes out of the window, and he begins to use me however he likes. It feels amazing, it’s such a different feeling to getting fucked in the pussy. I start to rub my pussy while he does this. God it feels amazing doing this at the same time. It’s like all the pleasure of masturbating, but the additional pleasure of getting fucked.

He begins to grunt, “I’m close, I’m close. Where do you want me to cum?”

“I want you to cum in my ass”, I whimpered, mostly out of embarrassment. I’m still really bad at dirty talk even to this day.

He begins to fuck me really hard and then slows down to a crawl. He begins to let out some moans, and I feel his cum filling me up. He pulls his dick out of me and I feel some of the cum leak out with it, dripping down to my pussy. At the same time I’m starting to get really close to orgasming. I tell him to get the dildo and continue.

“Pussy or ass”, he asks.

“Either!”, I thundered.

I begin picking up the pace, and he slips the dildo in my pussy and starts fucking me hard with it. It didn’t take long for me to start seizing up. The contractions forced some more cum out of me and down my pussy, which only made me orgasm harder. This was by far my favourite sexual moment. It had been a while since I orgasmed from sex, I mostly can only get myself off. It was such a powerful orgasm that almost my entire body seized up, and my legs spasmed. Maybe I was becoming a cumslut? (shoutout to /r/cumsluts btw, I get myself off to that sub so often nowadays).

“I’m guessing you enjoyed it?”

“Absolutely”, I said panting as if I had just run a marathon.

I just had to lie there for a few seconds. I went up to get in the shower.

“Where do you think you’re going?”, he said.

“Uhh, to the shower?”

“No no, get back here, you can’t shower yet, I have to enjoy this some more.”

I sheepishly crawl back in to bed, and he joins me. I rest my head on his chest and swing one of my legs over his legs. His cock was right by my pussy, and it occasionally brushed against it. Unfortunately we couldn’t fuck again though, I heard about all the UTI horror stories from people who went straight from ass to pussy. I don’t even think I would’ve had the energy to go again. I would’ve just been lying there like an inanimate object haha. I was so exhausted. He just caressed me the whole night until I fell asleep, playing with my air, stroking my back. I’d never done “after-sex care” with anyone but a boyfriend before, but its definitely something I wanted to do more after exhausting sessions like this.

I eventually feel asleep in a pool of his cum. I woke up early in the morning and he was gone. He had messaged me on Tinder and said he was going out with friends, and that we should do it again some time. And yeah, there is no way I wasn’t going to do that again.

The end :) Until next time!

Source: reddit.com/r/gonewildstories/comments/czlk4q/my_first_time_trying_anal_fm