Bored & feeling the need to touch on a good memory. This happened back when I was 25 and she was just a few months older. We took a trip up and down the state during a long weekend to see our favorite bands on opposite sides of the state. We were happily in our relationship for a couple years at this point, with a libido that matched our ages and obsessive nature we had towards each other. This meant many hours in the car, ranging from alien talks, to work, to dirty talk with some light playing/teasing while I drove.
We got into our hotel at a decent time and had a night to spare before the second concert. After we checked in we went full-on 15 year old, making out and getting gropey. When checking into hotels, we would always ask for two beds (making us look like good-Christians) while in reality we really just wanted to have a sex-bed and a sleep-bed.
After a days worth of teasing in the car and chafing my cock against her dress, I was over it. However, she was ready to eat and wanted to keep the tease going as long as she could.
Break for Description-Time:
Myself (Feel free to look at my post history if you absolutely need more):
5’7 with a 145 pounds hanging off my frame. Good smile and people like my hazel eyes. Generic white-guy haircut, but none of that Macaroni Penguin bullshit. My unit is built like a decently average bud, and that’s cool with me. As a musician, I have good control of my hands.
Herself: Bre
5’6 with about 165 that rounds her out a bit. From the head down, Shoulder-length hair box-dyed the generic dark brown. Enough eyebrow where she’s not full Cara Delevange, but doesn’t need to fill them in. Her eye’s had the color of the Nasa Hubble Satellite pictures, with the strange blue nebulas. Smaller lips that work with her pale complexion and freckles that lightly darken her base tone, with a quirky Haley Williams gap between her two front teeth that she could rock with some confidence.
36DDD tits that were magnificent, as long as we weren’t bra shopping which was always a nightmare. Surprisingly enough, her tits were incredibly sensitive for being as large as they were, and always wanted to be played with. They had a natural hang that assured they weren’t bolt-ons, could turn heads with a turtleneck on, and made my head get fuzzy when she exposed them. Her areolas were appropriate for the size, but almost invisible if not for her mammary glands, which built all around her nipple, even having one on her left side nipple. She had a bit of a tummy, but nothing that hung out over a top., and had a piercing scar that was always fun to play with. Bre was surprisingly flexible for having thick thighs, and a pussy that gave way to just a hint of labia. Her scent was always a perfect hit of pheromones, which made my life so much easier going down south. In the years we dated, I can’t recall a single day of her having any BO, god bless it.
Back to the story:
Bre & I go out to dinner much to my dismay, which happened to be our favorite Mexican restaurant 6 hours away from home. All the problems from our lives were pushed to the side for that weekend, and we enjoyed each others company, while turning 1 margarita into 5 real quick with my wallet crying at the $200+ dinner bill. We round out our trip there, and head back to our hotel with a 12 pack ready to be entertained by shitty hotel infomercials. The 12 pack get’s halfed quick, and at this point we’re both pretty trashed, but feeling good.
She’s calling to an end to her drinking, because she has a line between “Let’s Party” and “Cry in the bathtub for 2 hours over a hamster that died when I was 7” that we chose to walk a little more than we should. She’s laying on the bed getting handsy with herself while the AirFryer guy is bragging about how good DinoNuggets taste. I’m kinda confused but anytime she could let her guard down and feel sexy about herself I would jump on the opportunity however I could.
I get her yoga pants off, and start with a light leg massage while she’s rubbing her tits. Having thicker thighs gave me so much to work with and has fucked up my image on the feminine body ever since. Light massaging turns into little kisses all across her legs. I jump from her shin to her thigh, then up to the crevice between her legs and her mound, with her gasping at the steps towards her womb. After getting teased for half a day, I wasn’t ready to rush any sort of satisfaction. Kisses turn to tracing her curves with my tongue, disregarding her pelvic area and moving straight to her belly. As I’m playing around up north, she’s not shy to let her frustrations be shown in her moaning. She wants me to suck on her tits, but I would only grace her areola for a second before refocusing somewhere less erogenous. This goes on until I have her skin tingling everywhere, in which a kiss to her elbow could make her moan and leak out of her pussy.
I take my sights and tongue down to her mound, which is the only place on her body that wasn’t moist due to my tongue. I give her mound a full massage carefully watching so my hands so my hands wouldn’t dare touch her inner lips until I was ready. Bre is shifting around enough trying to manipulate my hand into reaching into home plate, while borderline screaming that we skip foreplay and that I just fuck her please. Jumping a small step, I trace my tongue along her slit, which has already made a puddle in the bed at this point. after a quick trace from her gooch to a hint of the clit, I dive my tongue deep inside her, giving her pussy enough of a tunnel to unleash a river of moisture into my beard. Within seconds I have her screaming, making my neighbors stoked I’m sure, and finally let her reach her first orgasm. She was never too difficult to make orgasm, which did make my life much easier than it needed to be.
After getting calmed down from her orgasm, she decides she’s had enough and pins me down, spins around and slams her pussy down on my cock as fast as she could in reverse cowgirl. She goes full jackrabbit on my cock, with audible smacks and the sound of water slapping together from all of her juices soaked on my cock. Quickly she goes from pornstar straight back riding, to leaning forward, to hands touching the bed, to palms touching the mattress, in almost a lazy doggy-style without me having to do any work. I get the hint that she could use a break, and shift my lazy ass around to fuck her properly doggy style. To this point, the only thing that’s been utilized by me were my hands and tongue, so my hips were ready to rock. I fucked her deep, fucked her hard shifted so my hips were level with hers, getting the deepest penetration possible and her face buried into the pillow just crying (with tears of happiness because I thought I fucked up for a minute and did a quick check-in, which lead to this).
I asked her how she wanted to be fucked, to which she responded with “As long as it’s hard and fast, you can fold me like a fucking pretzel for all I care”. She wanted long and hard, and I took my chance to slam into her perfectly cush ass as hard as I could. The best part of her being a bit heavier than I was, is that no matter how hard I tried, since her hips had more meat than mine, it was absolutely impossible to bruise my hips, which was incredible.
I pull completely out and slide my cock deep into her womb, which was all-welcoming. The whole time I am fucking her from behind I had the cutest little sheriffs badge that somehow got lubed up staring at me. She wanted hard, I was going to see if I could end up in the dark.
To this point we had never talked about this, she never showed any interest, I never cared to go somewhere without her having an inclination, but us both being boozed up got us in the exotic mood…apparently.
I rub my thumb across her asshole, easily lubing it up from her juices off my cock alone. At this point we we’re fucking where I had to keep pulling out and mop up her cum from off my cock due to the complete absence of friction inside her pussy. I make little circles around her hole, and watch as it starts to relax to my touch and swallow up the pad of my thumb. Bre is making noises that were full animalistic, and trying to spare her my thumb nail scratching her insides, I switch to my middle finger circling her entrance, which it sucks in like a vacuum to a cotton ball. Her hips buck, I stop all pumping and bite the living hell out of my cheek to keep this image from making me cum, and she goes into full body convulsions. At this moment I was incredibly happy I was still kinda drunk, because no sober mind would have let me not blow my load at that image.
Realizing I need a break , I swap my middle finger, which touched depths she’s never felt before my tongue to make it a little more easy of a transition. Her ass is in the air with her face buried into a pillow, I’m knelt behind with her ass spread for my feast, and my thumb just below my beard lightly pressed and ready to massage her clit. I’m patting my head and rubbing my tummy with trying to keep a constant focus on her clit with my thumb and my lips and tongue touching her most sensitive area. She’s gone from screaming into her pillow to a submissive weep, and a constant state of goosebumps flaked around her body. When coming up to breathe I’m telling her she’s so sexy and accepting of my tongue inside her ass, while watching her pussy leak down her legs. I’ve gotten her comfortable in the most vulnerable position I can imagine someone being in, and I feel like I won the Olympics. We could have stopped there, without me cumming and it still would have been some of the best sex of my life.
I roll her over, and in the heat of the situation (disregarding the germs) we start to make out, much like the 15 year old version when we first checked into the hotel just hours before. Much of our sex life consisted of us making out with me sliding my cock in while completely laying on her in missionary, with just gentle rocking, almost as a second-thought to the making out. It was almost more of a way to get the jabbing stick out of the way when we were trying to be lovey together.
We’re making out, my cock slides into to it’s home, sweet nothings are whispered into our ears, and the pace picks up a little. I shift up to my knees, so her clit can get some hand attention, her hips are doing most of the work while I use my hands on her body. At some point I pull out, and she shifts her hips up. I go to kiss her, and my head reaches an unusual resistance. I continue to rock gently as we kiss, and as our lips break, I look down and see just what it’s rocking at. I look back up, and with a fire in her eyes, a twitch of her eyebrow, and a subtle bite of her lip I took my shot.
I don’t know how it worked. We hadn’t properly lubed, 1 finger was in there for 15 seconds minutes prior, and we had never played with her ass before, but it worked. For the sake of ego, we will blame it on my cock not being a goddamn redbull can.
My head slipped through the first muscle, and quickly past the second muscle in her ass. I had the power of a thousand cock rings squeezing on my foreskin line, if I had foreskin. Bre’s eyes roll and her whole torso convulses from my entrance. I asked if she’s okay, she gives me a smile and slowly I bury my cock into the depths of her ass. After a solid 3 minutes I reach the hilt, with me face to face with her telling her that my balls are flush against her entrance. We have an oddly sensual makeout session while buried in the taboo zone, and she’s starting to plead for my cum. I slowly start to work a pace with her vice around my cock, asking where she wanted me to cum. She asked that I “break in her ass with my cock” and within 15 seconds, I unleashed a days worth of edging deep into her ass, with her flinching at every pulse.
As the endorphins wear down, and the minds become more sober, she asks that I pull out much akin to ripping off a bandaid and to get it done quick. I pull out, and much to our dismay, that night our sex bed also became our sleeping bed as we wrapped up together and laid in the puddle of our juices together. On paper it sounds disgusting, but in reality I don’t remember it until morning when we had dried cum all over us.
What wasn’t super fun was her waking up with a sore ass, with some waddling and her cussing me out every time she had cum out her ass. It never became a regular activity, and it really wasn’t our thing overall, but it was one hellofa night.
That’s all. Thanks for reading if you did. If you didn’t that’s cool too.
Source: reddit.com/r/gonewildstories/comments/9xtf1o/surprise_first_anal_mf
Very sexy story! Me and my wife have had successful anal like twice and it’s good but pussy to me is better lol