First successful night of anal [MF]

Brittany has been in this phase where she likes to fool around in public. We’ve made time before a movie, she placed my hand up her dress at dinner, some changing room fun, a few quickies while she’s on her lunch break, went down on her at her work party. We almost got caught each time and something about it gave her this insatiable craving to keep pushing it further and further. As the set up, it was my first week of school (Jan 14-18) and she wanted to be cute and drop me off for my first day. I didn’t want to be late so we were about 45 minutes early. She was wearing a simple, yet very sexy blue and white maxi dress. I love her in a maxi dress. jumping 10 minutes, her entire right leg is uncovered and she’s putting out this “notice I’m not wearing panties” vibe. My windows are tinted including my windshield. Brittany, without saying a word, climbs over my console, seats herself against the passenger side door, and pats the seat next to her “come see.”

For anyone reading this who hasn’t read any previous stories about Brittany, she 5’8”, platinum blond hair, almost silver. She weighs about 120 (+/-). 34C, very light colored nipples, curvy round muscular ass and legs, bright green eyes, gorgeous smile, moderately tan with some tan lines. She (usually) has a beautifully waxed, perfect little innie mound between her legs that’s almost bright pink when spread open. Which you have to manually do since it’s sealed shut regardless of how far apart her legs are. So neat and smooth with a cute little skin colored asshole. Sexy toned back and slightly visible abs. My favorite thing about her though, she smells so good, I can’t explain it. Makes my mouth water. I could go on…

I jumped in the back and Brittany asked if I was nervous for my first day. I wasn’t. She said “well it fits my narrative, so you’re nervous and I’m helping!” as she undoes my belt. My erection is firmly in her grip as she lowers her pretty lips down to the tip. She’s smiling and looking me in the eyes while she lollipops the head. A few deep sucks gets her nice a turned on. After getting my cock shiny and wet, she climbs up and lowers herself down giggling the whole way. She bites her lip looking out the windows to see how many people are walking by while she begins sliding up and down my shaft. My windows are illegal as fuck, no one can see in unless you press your face on the glass and focus. I like her little nervous giggles though so I don’t share that info. So, we get to it, fucking in the backseat like we’re teenagers. Had a nice little quickie, probably 5-7 minutes. She pulled her dress off her shoulder and hovered her tits over my face making good use of her hips. Her giggling ass is smiling at me like she knows she’s doing something bad and enjoys the thrill.

When the time came, she did the quick cleanup and took it all in her mouth and down her throat. Several mouth filling gulps and her silver head pops up with this glimmer in her eyes. I know now what it was, but she was radiating joy. She was adorable despite just swallowing her boyfriends cum in a parking lot. So post cumshot, I go to class which is only 50 minutes so she met a girlfriend at a nearby coffee shop to hang out. Apparently they got hit on by, I assume, frat boys. Shocker. Anyway, we’re back home hanging out watching TV and she’s asking me about class. She still has that look in her eye and I mentioned it. Brittany gets up from the bar where she was doing some work and walks over to me. She mounts my lap looking down at me, whips her hair over her shoulder while wrapping her arms around my neck. “I know something you don’t know” as she kisses my forehead then my lips.

After she puts the baby to bed, Brittany walks me into our bedroom to share a secret. She’s wearing her robe, a nice silky jade green and some knee high socks. Makes her look like royalty. I have no idea when or where she took her panties off. When she hops on the bed and crawls up to the pillows, I noticed a red jewel. Red is important because it’s the large plug and Brittany has never been able to handle it. She reached back and spread her ass with one hand looking back at me biting her lip. “Guess what I’ve been wearing since dinner…” I’m hard now. She gives it a tug and tells me to come take it out. Brittany’s on her stomach, ass exposed, and I get a firm grip on the stud pulling outward. Her asshole begins to open as more and more of the plug forces her apart. She shouted into the sheets “oh shit… goddamnit, so much bigger…” At the thickest part, I noticed that it was about the same girth as me. It hit me like a train. This is what she “knew” and I didn’t.

I was fucking stoked. The plug comes out, I forgot how heavy it is. It has to be two pounds. “Grab the good lube and be generous with it” as she takes her robe off. My clothes hit the floor and she says “since you’ve been so patient and so good to me, I’ve been preparing. Annnnd… today was a big day for you. I wanted to give you a back to school present. From me… for you.” After we had a cute moment, Brittany whips her hair exposing her neck positioning herself on her knees and elbows. I asked if she wanted some foreplay or anything at all. She said “I had it in for over 3 hours and I’m still crazy horny from earlier today. I’m ready to go.” Hey message received. I apply a healthy coat making sure the outside and inside is ready to go along with myself. Just to tease, I spread it around and fingered her ass starting with one finger, then two going as deep as I could, then I worked my index finger into the mix making it a trio. She jumped but didn’t wince in any kind of pain. I kept asking and she said she was good. Moment of truth.

Brittany manages the tip to let me cum from time to time, so it wasn’t bad popping the head in. With so much lube, it broke through and I was sliding in slowly making sure she wasn’t just enduring it for me. That’s the last thing I want. So far so good. She moaned with each inch that found its way in her ass. Before I knew it, my hips were pressed against her and I was deep down to the base. No pain, no hesitation, just sheer overwhelming anal sensation. Brittany smiles nervously saying “so, it’s a lot more intense than the plug. Significantly more, but better.” I reached down to help add to her stimulation, and what I felt was unexpected. She was literally dripping wet. I can tell the different between our lube and her natural lube. She was so fucking turned on it turned me on. I’m still completely inside and she comments “It’s throbbing. Like a pulse.” I’ve heard that before. Good to know I’m consistent. I asked if she was good and she said very sarcastically “nothing more comfortable than a red bull can in your ass.” I began to fuck her slowly and passionately. As passionately as anal can be at least. She was taking it, and most importantly, she liked it. I could hear her moaning under her breath “mmmmm, fuck that’s it… that’s it baby, just like that. Give it to me slow.”

The first minute was pretty unexpected. I didn’t think she would react so positively. She said some things I’ve never heard her say before. “You wanted to fuck my ass for so long… I love the things you do to me. I love that cock. It’s making my pussy drip down my legs…” She rarely talks that dirty. She pulled her vibrator out from under the pillow which I guess she placed there in preparation, and began to rub her clit. We’re maybe three minutes in and she was killing it. Her ass was enduring and she was really into it. Then she said “harder… do it harder.” I turned it up a bit. She let out these animalistic guttural moans between talking dirty. The vibrator was on the high setting and I could see her ass and thighs twitching and flexing.

This is a first for us so I’m in uncharted waters. All we can hear is that sticky lube smearing sound. Then her back flexed. I could see every muscle clear as day. Brittany had a handful of the sheets and the surge gripped me as it flooded her body. She was on the brink of a first time anal induced orgasm. The veins in her neck surfaced as she got red. Brittany buried her face in the pillows and screamed. Her asshole was clenching so hard it kinda hurt, and I liked it. If you’ve read any of our other stories, she doesn’t take long at all. She can cum shortly after penetration. It’s not me, it’s all her. I consider it a gift. Anyway, I can hear her screaming into the pillow as her body convulses then I felt a splash on my legs. She finally after all this time squirted and there was nothing she could do about it. It was one quick release and then she couldn’t manage her fine motor skills as she dropped the vibrator. I held her up and kept my pace. She kept cumming. Again, all her. This is how she is and it’s fantastic. She’s quivering and going limp so I ease up and let her process what just happened.

I pressed against her, still inside and we rolled onto our side so we were spooning. I could see the veins in her neck and forehead beating rapidly and her heart was thumping away like a hummingbird. Fast deep breaths and trembling to match. I barely moved and her whole body twitched in aftershock. I kissed her on the neck and started dragging my fingertips all over her skin. I asked if she was ok as goosebumps scattered across her skin. She licked her lips and shook her head yes. “I’m gonna pull it out ok.” She didn’t say anything, just sat there catching her breath. I thought I broke her. She was limp like a rag doll. “My whole body feels tingly like when your foot falls asleep.” I asked if she was hurting and she said no. Not even a little bit. I peeked at the sheets and saw a wet spot about the size of a dinner plate. That made me smile. For whatever reason she gets a little embarrassed about squirting, but she said “your entire dick was in my ass, I don’t think a little squirting is anything to be alarmed about now.”

Once her outer body experience was over, we got back to it. I wanted to see her reactions so I laid back and she got on top of me with her ass pressed against my dick. It felt different with her on top for obvious reasons. Her eyes closed as she lowered herself down onto me exhaling a subtle little moan. She went all the way down and for a second she just looked at me smiling as if she knew she conquered me. I could feel her clinching like a hybrid kind of handjob. That amplified how turned on I was that she was toying with me. She asked “is it everything you hoped for?” It was better. I asked her the same and she looked up at the ceiling leaning back and shook her head yes. Her pussy was still leaking leaving a wet spot on my pelvis. A nice thick sticky fluid dripping on me. Brittany began to flick her hips clenching at the peak of her thrust to strangle my cock.

I was enamored watching her use me to get off. I think once that initial orgasm reset her train of thought, she tried to find her sweet spot. Exactly how she likes anal and I was along for the ride. She was already stretched out so she was making use of the situation but I felt a difference in tempo. My hands were rubbing her hips and legs when I made my way to her clit. As soon as I touched she grabbed my hand and sucked my ring and middle fingers. She placed them in an upward position so she could ride my fingers and cock. When I broke her tight seal she clenched her ass and a quiver surged through her. She was overwhelmed with this new sensation. She was beginning to feel that tingling sensation again and she knew I knew. My free hand started circling her clit while she made use of my fingers and cock still filling both her holes. Her breathing picked up and she got hot. Like putting off excess heat. I could hear the lube in her asshole sliding up and down my shaft. The whole image was perfect. I told her I wanted her to cum for me. She shook her head in compliance and picked up the pace. Shorter but faster strokes. Her moaning and breathing became quick and choppy. Brittany’s looking down at me with this determined look and she whispered something under her breath. I couldn’t really make it out but it contained squirt and mouth. I filled in the gaps.

About 20 second went by and I’ll never forget these words for as long as I live. She very explicitly said “I want you to fill my ass with more than your cock. I need to feel you pulsing. I want to flood your body when you fill my ass.” After that statement I didn’t have much left in the tank. Then, she lost herself in orgasmic ecstasy. She twitched and convulsed so hard I had to grab her arm so she didn’t fall off the bed. My palm was filled with what came gushing out of her. She dripped down my sides and wrist. Her eyes were closed tight and her asshole was clenching in rapid waves. This is about 5 seconds in. She fell foreword bracing herself up on the headboard. I took over and tried to give as much as I could from the awkward angle I was in. My hands gripped her ass spreading it open. As soon as my fingers came out, more juice flooded out. Brittany has a few wet right handed prints all over her left side. I kept pumping her ass and she kept cumming.

Her contractions were slowing down but still as powerful as the first. Those perfect tits were a foot away from me but the real perk was watching her facial expressions. I could see how good this felt for her. She’s come such a long way since we’ve been together. I watched her body flexing in both mirrors. Seeing me inside of her was something else. A few months ago she was shy about me going down on her, now she’s sending nudes from work, wearing buttplugs out to dinner and movies, fucking in public, and taking it in the ass.

She collapsed on top of me. I could feel her breathing against my neck and her sweat coating her flawless body. She reached back and pulled me out of her. I watched in the mirror. Her cute little asshole was barely gaped open, like dime sized. I started scratching her scalp with my dry hand and she asked “were you close because I don’t know how much more I can handle. I know I’m gonna be sore tomorrow so take advantage now.” I said we can go vaginal and she said “no. Finish me like this. I’ve been thinking about this all day and I want you to do it inside of me.” So I put her on her side with her leg cocked up and she said to make it count. I could feel her body trembling still. So, the tip of my dick is pushing against her backdoor and I popped in. She jumped and said “ooo that’s different” while laughing. This is my favorite position personally and now she can take it either way. I knew it wouldn’t be long, but man I’d be lying if I said there wasn’t at least 25 other positions I wanted to try.

I’m going slow and she’s watching me watch myself penetrate her. She has this satisfied smirk like she’s getting what she wants. Almost cocky but I like that. She played with herself while I had my fun. A little time goes by and I asked if she wanted it deep or shallow. She grabbed my balls and said “as far as you can.” Good god damn answer. She was gently dragging her nails on my balls and reached back with her other hand placing her fingers on both sides of my cock in a V shape. I think she was checking to see how her hole felt to be forced open so far. She seemed impressed with herself. There were a few wows and oh man when she realized just how much she was taking.

Shortly after I could feel the euphoria of an eventual orgasm. That semi lightheaded tingling sensation was a little more powerful due to the nature of this scenario. The ball tickling was definitely helping speed it up. I told her I was close. She lifted her leg higher for added grip. My hands were on both sides of her head and we were looking directly into one another’s eyes. She bit her lip and shook her head yes. Brittany whispered “deep. Please do it deep.” As I’ve stated numerous times, I have very large cumshots. This was no exception although I couldn’t see any. I rammed the entirety of my cock up her ass and she groaned as I began to pump her full of cum. I could see the veins in my arms and hips were filled to capacity. I’m not much for making noise, but this was different. I groaned against her chest and she kissed the top of my head as cum filled her ass.

She had her eyebrow raised with her lips slightly apart and her tongue between her teeth. She squeezed a little tighter on my balls and at the base of my cock while letting out a little satisfactory moan. I shot and shot until I felt them subsiding, so I pulled out and let the last few ropes decorate her asscheeck and hip. Without moving her neck, she glanced down at it and back up at me with that eyebrow still raised. “I can feel it inside of me. Theres a warm spot pretty far up.” I knelt over her leg with her other one over my knee and her ass began to leak what I just flooded in her. So, trying to keep this crazy sexy atmosphere alive, I grabbed the medium plug and used the dripping cum as lube stuffing it in her ass so she didn’t drip. Brittany was still smirking and said “oh yeah? Don’t want me to waste any?”

We ended up making out like teenagers for a little bit when she said “were fucking filthy. Please go turn the shower on.” That air hitting my dwindling erection was cold. We got in the shower and had a nice sensual moment. I grabbed her ass and felt the plug was still in. “Well I didn’t want it all over my legs.” She pulled it out and I handed her one of the shower heads. As soon as the plug came out so did a river of jizz. A normal amount from the looks of it. I wanted to help her so I pried her open with my index fingers while she shot water up her open ass. And that was pretty much it. I ended up going down on her while we were in, but that was more for her since she made my whole month with this. I’m defiantly setting some money aside for a ring. Even though she lets me do all kinds of crazy sexual things to her, it’s the smaller cute things in between that I really like. The smirks, the giggling, her piercing stare watching me empty a load on her… stuff like that. She doesn’t miss an opportunity to make a moment better.

Source: reddit.com/r/gonewildstories/comments/am8q26/first_successful_night_of_anal_mf