Me and Alexa’s first successful anal sex experience. [MF]

Refer to [our first encounter](https://reddit.app.link/osIZ6AHvvO) to get an idea of our history.

Alexa and me had been at it for a few months now. She was down for anything as long as it felt good and was risqué. She had a few toys. Vibrators, plugs, anal beads, and some desensitizing lube for such an event. Every time we had sex, her ass was involved. We had been working up to full on anal sex. We got it in a few times but to no avail. The length wasn’t a problem, it was girth. The anal beads were her favorites, especially when she was on her knees. She would pull them out while I was fucking her from behind, curling her toes when one stretch her asshole and pop out. We ended up getting bigger ones to help her get used to something thicker.

Our first time trying was after a drunken night out. We’re at her place, a nice loft in the city and she puts on some music. Not romantic, candle lit, love making bullshit. We’re into the same kind of music. We’re bumping Urfaust. Ambient, melodic, black metal. Alexa gets aggressive when she drinks, mostly with herself. She gets what she wants and you’re along for the ride. We go up to her bed overlooking the apartment. She strips down to her bra and panties and unbuckles my belt. Alexa jumps up and wraps her legs around my waist kissing me. “Tonight’s the night. We’re gonna get me nice and loose, then we’re finally gonna get this (grabbing my dick) in my ass. First, we finish this bottle I’ve been saving. It’s on the counter. Get it.”

I’m walking up the stairs to her bed and she’s naked laying back on her elbows, legs crossed like a playboy model. “Can you help me with this?” She has her thumb through the loop at the end of the anal beads giving it a little tug tug. She stuffed six blue golf ball sized beads up her ass in the 30 seconds it took me to walk down and up the stairs. She’s looking up at me and says “off. Now.” Then gestures for me to come see. I strip down and kneel over her. I pop the top off the makers mark and she snatches it out my hands and knocks back a few sips. “Drink up. We have to get me anal drunk.” I take a few sips and she starts dragging her nails up and down my cock gently. “It looks menacing from this angle. I’m having second thoughts… I need to drink more. I’ll finish this little bit, but you have to go down on me.”

I grab her behind the knees and spread her legs open. Her pussy didn’t budge. It stays sealed together and I reach down prying it open. Once it opens, it looks like a hot pink flower. I get to work prodding the hole with my tongue teasing her. I can hear the bubbles from the bottle as she knocks back the last bit. “God, I’m gonna be fucked up now.” I took my time playing with her. Her tattooed body moves and bends as I drag my tongue against her clit. I was licking to the music. Her big fake tits sitting perfectly centered expanding with her breathing. It had to have been 10 minutes of pussy eating. I lost myself and she obviously wasn’t gonna stop me. The steel ring attached to a line of beads is around my finger and I’m pulling on them. I can feel the resistance from the first one breaking the seal of her tight asshole. I don’t pull it out, just enough to gape her hole. Normally she moans, but she’s fucking hammered and let’s out this sexy laugh while squeezing her tits. Alexa grabs the back of my head forcing it down into her then wraps her legs around my shoulders. “If you want to do me in the ass, you should probably lick that too.”

She rolls onto her side so it looks like a pink sideways exclamation mark. I pull on the string of beads hard enough so a little bit of the bead showing. My tongue presses against her rim dragging around in circles. “Pull harder. I wanna feel them stretch my ass open. Oh fuck it, pull them all out!” I watched all six open her asshole only to have it immediately seal up after each one popped out. Each time she made a sexy little groan when one exited. The lube must’ve worked because she seemed pretty desensitized.

I press my index and middle finger on the hole, slowly entering her ass. Despite the beads and all the toying we’ve done for the last few months, there was barely a noticeable difference. Once I’m knuckle deep, I starting fingering her asshole pretty roughly and she was into it. She was up on her elbow with her long black hair running down her side watching me, biting her lip and smirking like she was in heaven. I was pounding her ass and twisting to stretch her in every angle. She was loving it, giving me encouraging remarks the whole time. “You can’t wait to put it in. I can see it in your eyes. Oooo my god… that feels so good. I’m so ready for that cock. I want it. Come up here, fuck me.”

I get on top of her and she starts jerking me off and biting my neck. “It feels so big. Look at that thing. Look at these veins.” Alexa wrapped her legs around my waist and sweeps me on my back crawling on top of me. She puts her hair in a pony tail and drapes it over her shoulder. I can see how drunk she is. Her skin is reddish and she’s radiating body heat. “Pussy or ass? Hmmm, I do want regular sex, but I think we’ve built up too much to not do my ass. And we both know once we get it in I won’t wanna stop, so ass it is!”

We get into position. My legs are over the edge of her bed, and she’s facing away from me standing up. She has a mirror at the end of her bed so we can see each other. I open her cheeks and she puts the lube nozzle in her ass and squirts a little inside, then rubs the outside. I can see the determination on her face. I’m throbbing like a heartbeat now. She lowers down on me guiding it in. She was fighting for a few seconds trying to force it in. I grab her ass and spread her cheeks so she can focus on penetrating. The tip of my cock is all shiny from the lube. She inserts her finger to open her ass then uses it like a guide for the tip. I feel an immense pressure. It’s in. Half and inch broke through. Alexa’s eyes close as another half inch disappeared inside of her. Then another. And another. And another until half of my cock is being strangled by her tiny asshole. “It’s in! We did it baby! You’re in my ass! Can you feel this?” She clinches my dick inside of her. “I can obviously feel it.”

She’s standing there with about four inches up her ass when she starts to slowly ride me. I hand her the vibrator and she puts it right on her pussy. She just repeats “oh my god” over and over again. It felt amazing. If she barely shifted her body, I felt the difference. Her ass was strangling my dick. I started rubbing her back and ass with my fingertips to help shift her attention. We make eye contact in the mirror and she says “I’m gonna sit all the way down. I have to scratch this off my list.” You’ll hear no objections from me. And from the very tip of my cock, her asshole swallows every inch. I disappeared bit by bit until I was supporting her weight. She puts her hands on her knees and just sat there looking at me in the mirror with this grin of satisfaction. “Well, it’s in. I can feel everything too. I don’t even know how to explain this sensation. It’s like kinda painful, but fuck, it feels so much better than the toys. Like natural instead of plastic. Let me get used to it while I’m all the way down.”

I sat up and started kissing her neck and shoulders, cupping her tits and rubbing her pussy. She throws her legs over mind so I’m completely supporting her up. It felt even tighter with her legs open. I was inside of her for about 5 minutes. Alexa’s hands start to play with my balls and her clit, getting herself off. I have a finger in her pussy and we just sat there playing with her. She leans against me and starts to shift her hips. I wanted to bend her over and pound her ass so bad. I let her do her thing for a while when she tells me to lay back. She puts one leg on the bed frame and starts to ride me. That was a damn good view. Her ass was stretched to capacity. Like a tire around a rim. She’s looking at me in the mirror again and starts talking extremely dirty. Like I’ve never heard from her before. “I can’t wait until you shoot a load deep in my ass. I love how much cum you shoot. You like watching me fuck you. You like watching my tight asshole stretch over that cock don’t you? You can have it whenever you want it.” She’s going to town now. Alexa is totally fucking drunk. She’s dropping down hard. Once I knew that, it was my turn to be in control.

I grabbed her hips and flipped her on her stomach. My dick gets some fresh air and I apply some more lube. She puts her legs together and spreads her ass open for me. I climb on top and straddle her. The tip of my cock makes entry again and she immediately says “this position is gonna make me cum. I can already feel it.” I have her ponytail wrapped around my wrist and my other hand gripping her hip. She moans into the blankets “just fuck me! I can take it!” I’m not as drunk as she is, but I’m borderline hammered. So, I indulged and began to fuck her into submission. Alexa grunts every time my balls slap her pussy from bottoming out in her ass. The music drowns out the noise of us slapping together, but not loud enough to cover her yelling. “Holy shit! I think I’m gonna cum! Im think I’m gonna cum! (Panic breathing ensues) Fuckfuckfuckfuckfuckfuck…” her eyes close and her mouth opens. She screamed out “JESUS! IM CUMMING! IM CUMMING!” I’m drilling her pretty hard and her whole body goes limp. She’s barely breathing, but her asshole is clinching like a heartbeat over and over again. Then the spasms kick in. She starts to tremble her hips and legs like an aftershock orgasm. She has a handful of blanket and bites the pillow in front of her. There was some other shouting that was untranslatable in there too. As I said in my last story involving Alexa, her orgasms are long. This went on for probably 20/25 seconds.

Once it was over she said into the pillow “I think I died.” I pull my cock out of her ass and lay next to her. “I still want you to cum. I’m drunk as fuck so nows your chance to give it to me as hard as you want. I’m gonna be sore tomorrow, but I can endure hardcore anal now” So, I had to give her what she wants. It’s only fair. She gets on her back and I get on top of her. I put her legs back so her ass is facing up at me. It had a little tiny gape. Like half the size of a dime. The vibrator clicks on and she starts to rub up and down her pussy while playing with her nipples. I press the head of my dick against her asshole and make entry again. “This feels the best so far. I like this position.” Her tattooed legs are over my shoulders and I begin to fuck her ass again. I’m taking my time now trying to make it feel good for both of us. Long deep strokes. She seemed to like it when I bottomed out. Alexa’s eyes are closed and she looks like she’s enjoying this moment. The vibrator is doing its job stimulating her clit while the other hand fingers herself.

“This feels really good. I think slow and deep is the way to go.” We fuck for about 5 minutes when I feel that looming sensation coming on. “I’m close. You want it in your ass?” She just shakes her head without stopping. She clinched making it even tighter. Smart girl. A few pumps later and the pulsing begins. Her eyes open and she smirks at me. “Mmhmmm” is all she says. I was so turned on the first explosion of cum took my breath away. My whole body flexed and each pump results in more and more cum, filling her asshole. “I can feel you pulsing inside of me. Holy shit. I actually feel the cum hitting.” I just sat there inside of her when she turns the vibrator off. “There’s a gallon of semen in my ass.” When I pull out, it immediately follows and starts dripping out. She rolls on her side and cocks her leg up so it goes down her thigh. She’s watching herself leak cum out of her ass in the mirror. “Look at it, there’s so much. How do you do that?“

She gets up and goes to the bathroom. As she’s walking away, it dripped down both her legs all the way to her ankles. She opens the door and tells me to come rinse off with her. We’re in the shower when she says “tonight, I think I’m gonna sleep with the big plug in. I wanna do it again when we wake up.” She did put the plug in, but had no memory of saying she wanted another round. She was sore, but not nearly as bad as I thought she would be. “It’s uncomfortable, but tolerable for sure. It’s more annoying than anything.” Was how she summed it up.

I think it was easy for her to take it because she was so accepting to anal. She loved fingers, toys, and rimjobs but because she was so petite, it was a gamble with sex. It took us about a month of constant toying and a few attempts to actually lead up to this night. The first time she got it in, she cried. I felt bad, but she was cool about it. We laughed it off. But it took desensitizing lube, about 5 minutes of her with my dick in her ass to get used to it, and lots and lots of toys during sex.

Source: reddit.com/r/gonewildstories/comments/8yg60v/me_and_alexas_first_successful_anal_sex