Drunk ex gets her first anal creampie [MF]

Better to read the Hawaii story first if anybody is reading this one without knowing the story so far.

Tiffany had money. She was a seasoned nurse anesthetist. I have no idea what that means, but she made enough to live in a really nice area in San Francisco, drive a jaguar, an wear (ironically) Tiffany jewelry. She liked to spoil me. And to clarify, I never asked a dime out of her. So, a group of nurses and doctors plan a dinner party at this really upscale place called lazy bear. All fancy rich people. Yachts and Rolex’s. Way out of my league being from crime infested New Orleans. So I have to dress the part. All I have is dress blues which I’m not fucking wearing. Tiffany takes me to this tailor and gets me fitted. Shoes. Ties. Sunglasses. All that other shit that you wear with a suit. A Tag Heuer. I see all this being rung up and I had to step in.

“Baby, you can’t spend 4500 on me. I can’t in good conscience allow you to spend that much money on me. The flights are more than enough I can rent a…” then she cuts me off by grabbing me by my belt looking through me with those beautiful diamond eyes. “You will wear the suit. You will wear the watch. You will look sexy in them. You will stand by my side through the night. And you will look sexy. You‘ll pay me back after dinner tonight. It’s NOT a fucking option.” So I’m trying on the suits at her house and I gotta say, I look fucking good.

Fancy dinner time. I’m waiting downstairs when she comes down in her dress. It’s a shame all I wanted to do was tear it off of her. Animal instincts aside, she looked beautiful and that’s not giving her nearly enough credit. A dark ash grey with a high cut exposing about 90% of her leg. Medium cleavage and collar bones showing. Black stockings. A soft red lipstick. Very little makeup, she didn’t need it. Her long wavy hair down her exposed back. Flawless. We show up to lazy bear, really upscale joint, and it seemed like everyone was looking at her. Men and women both. Her body alone was a magnet for attention. Her smile and laughter was contagious. She commanded it.

I’m meeting all these millionaires, surgeons, lawyers, and other stuck up cocksuckers when Tiffany tells them I’m on my way out of the Marine Corps. I feel a little judgement from them, but she was happy and radiating joy and that’s all I cared about. I stick by her side all night and when they look at me, I plant a kiss wherever I can land one. Were at our table with a few other couples and she grabs both my hands staring me in my eyes “you can take your aggression out on me at home” then blows me a kiss with a cute little wink. After dinner, she’s buzzing pretty good. I’m driving us to her house when she puts her hand on my leg and says “I’m in love with you. I have been since Hawaii. I know you feel it, and… I love you.”

I said it back and she releases her dress biting her lip. Those big, beautiful, perky DDs sitting high in the center of her chest. She throws her dress to the side so I can see her lace thong.

Me – baby your windows aren’t that dark. Somebody’s gonna see you.
Tiffany – this isn’t for somebody. It’s for you. I’m for you. But, I can stop if…
Me – I didn’t say stop.

Tiffany slides her panties to the side and reveals that little slice of perfection that I love so much. She starts masturbating talking me through what she wants to do to me when we get to her house. I’m about to rip through these really expensive slacks when she asks “what if I come over there and suck your cock while I play with myself?” All I could say was “your car your rules.” I can hear her shifting on the leather seats getting in position. She unzips me and like a spring I shoot up through the opening almost into her mouth. I’m tall, she has plenty of space to work between me and the steering wheel. Then I feel the warmth of her mouth gulping down my cock. Her tongue dragging on the right side of me, playing with that huge vein I have protruding from my erect cock. Excellent technique, but she’s gonna get us killed because I can’t focus on driving.

About a minute goes by of her teasing the tip by doing that lollipop thing that’s a love/hate relationship because it feels awesome, but I want the rest of me down her throat. Somehow, she removed her panties during her dessert and had them wrapped around the base of my cock. I never wanted to catch a red light so bad in my life. I could hear her making blowjob noises. You know the ones I’m talking about. Sweet music. Her pierced tits are pressed against the center console of her car like they’re on display. That firm ass inch’s from the window, dress barely covering it.

I pull into her garage and we sprint out. Her panties hanging from my dick like a trophy. Watching her walk in front of me, I couldn’t resist. I attacked her right in the doorway. Were at the bottom of her stairs stripping and groping one another. Once I’m naked and all she has on is jewelry, titanic style, I turn her around and kneel her on the stairs. Tiffany reaches around her ass with one hand and spreads her pussy. I walked right inside of her pressing her panties against our bodies. I just left them hanging in me. She was already soaked from the short drive home. That tight little butthole sitting above my dick needed attention. I swiped my finger up her pussy to get it wet then press down. Her gasp of air followed by one of her notorious giggles was all I needed to hear. She wanted it. Tiffany’s tiny asshole swallowed my finger, resisting the whole way in. She took it and loved the pressure of being filled. I could feel myself fucking her.

Her moaning and breathing started to get quick and frantic. I knew what was about to happen. Drunk Tiffany is an orgasm machine. She arches her back until her stomach is touching the stairs. Her hips are twitching counting it down. And suddenly, the quivering and contractions begin. “Oh god! I’m cumming!” She shakes uncontrollably every time I thrust inside of her. Her asshole is contracting so hard I thought she was about to break my finger. Fuck it, I got 9 more. I was about to pull it out during, but she explicitly said “finger my fucking ass baby, deeper!” I began alternating strokes in and out of her holes trying to keep her orgasm going as long as I could. She just kept cumming. I had never seen anything like it before. She ended up collapsing and I had no choice but to stop penetrating her. She’s laughing hysterically trying to catch her breath when she rolls on her side holding her head up and says, “I think I passed out.” There was a little puddle where she was kneeling and those panties hanging off me were pretty soaked.

I had to carry her to the bedroom room because her knees were still trembling. To help her recovery from near death, I close her legs, spread her ass open and give Tiffany her first rimjob. She’s up on her elbows looking back with her eyes locked on me. I prod her asshole a little trying to ease inside of her. She rolls over sitting up and says, “we’re gonna try it.” She reaches in her nightstand and pulls out some lube and her vibrator. I put my face back in her ass and keep licking. ”(exhaling) why does this feel so fucking good?” I press my finger on her little hole and she arches up to expose the rest of her, offering herself to be fucked and fingered.

I crawl up and press my throbbing erection between her ass cheeks. Her legs between mine, she starts wiggling her hips massaging her asshole on the bottom of my cock. “I don’t think I’m ready for that yet baby.” looking at me in the mirror biting her lip. I knew it wasn’t time yet. I wanted to keep teasing her. Those panties were on the floor when I had an idea. Hopefully this makes sense; I put her wrists through the leg holes and twisted my wrist so my knuckles were facing me, then grabbed her thong and rotated my arm back locking her hands together above her ass. I highly recommend it. It’s sexier than handcuffs and feels a lot more personal. Plus you’re in complete control.

Her fingers are facing the ceiling when I slide my dick on her hands. She starts to tickle the bottom as I slide through her fingers. “Oooh baby I like this.” Her feet are restless anticipating me entering her again. I squirt a single drop of lube on her asshole and smear it with the tip of my cock. She lifts her hips giving me permission. Her nervous breathing was kind of a turn on. I begin to push the head of my cock in her ass to tease, when I rock back and slide straight into her pussy. Her little giggles are the best. “I got nervous for a second.” I’m pumping her with long steady strokes toying her asshole with her vibrator and she is fucking loving it. Pushing just a little but not breaking her tight seal. Her hands are still locked in place helplessly when I see her fists tighten. I’m driving into her hard but slow and in control. Our skin colliding sounds like a slow clap.

Her asshole is winking at me from the vibrations. She wants more. A few more drops of lube help me work a finger inside. I’m penetrating both her tight holes when I decide to try two fingers. Still fucking her pussy, I circle her rim with my index and middle finger prodding her over and over again going a little deeper with each push. Then it happens. Both fingertips are in.

Tiffany – Are there two fingers in my ass?
Me – Maybe. (Pushing in deeper)
Tiffany – oh, god damn. There’s a lot going on down there. Be gentle baby, this is new to me.
Me – I’m not gonna hurt you. I promise.
Tiffany – I wanna do it.
Me – I’m way bigger than two fingers baby.
Tiffany – no no, I wanna use my fingers.

I pull out of her ass and loosen my grip on her wrists when she reaches down and starts to tickle herself. I give her a few more drops of lube and in that split second, she buries a finger up her own ass. Fucking hot. No hesitation or caution. “It’s tight in here.” looking at me in the mirror. “It’s different, but Jesus it’s intense.” After she’s completely used to the new sensation, I start giving it to her a lot harder. She’s working her asshole and I’m still pounding behind her, when she presses downward putting pressure on my cock, through herself. All she says is “wow. That is just… wow” in amazement. She now has her middle and ring finger in, and it looks sexier because she still has all her rings on. I feel like I’m fucking royalty.

“This is gonna be new.” Her body starts quivering again. I’m curious as well because she’s really taking a liking to playing with her ass. Every muscle starts to flex and her pussy tightens around me. She kept her fingers inside still penetrating herself. I could feel the motions with my cock. This was uncharted territory. I could see a vein in her neck when she starts to orgasm. It hits like haymaker. Her legs go limp as she buries her face in the mattress. Her breathing sounded like she was going into shock. I slow the pace down giving it to her hard but in in sync with her contractions. Her free hand is making a tight fist while the other ceased all motion. Her asshole was contracting so hard it was moving her hand. Absolutely amazing. That was the secret to long orgasms. Anal play. Her fingers slide out naturally from being pushed when I see the tiniest little gape. Like a straw. Then it closed up. Progress.

Tiffany is trembling again. Like I broke her. She’s laughing trying to roll herself over. I back out of her and like last time, a little wet spot on her blanket. I grab her ankles and pull her to the edge of the bed flipping her on her back. It’s the perfect height for me. Her face is flush. She’s taking long euphoric breaths while sitting up on her elbows looking at me. She puts her index finger up saying me give me a minute.

“Ok. I’m ready again.” She is fucking soaked. The inside of her thighs and hips are wet. She’s a leaker. Her legs are wrapped around my waist when I put my cock back in. It feels like she has a fever. Her pussy is so warm it’s almost like a heating pad. Feels unbelievable though. Those perky tits jiggle as I penetrate her and she says “you have to take it easy this time. I can’t handle another one like that.” I have a firm grip on her waist while she cups her tits with her head back looking up at the lights. “Just like that baby. Long strokes. You feel so good inside of me. My pussy is so wet. No one has ever made me feel the way that you make me feel. I can’t wait until you’re out and we can fuck everyday.”

One leg is up on my shoulder and the other still around me opens her up. Not very far, but enough to see her clit and lips. They’re glistening from how wet she is. Her pussy makes that wet sound when I thrust in and out of her. She begins rubbing her clit and playing with her nipples looking me in the eyes the entire time. I could pop at any moment. So I told her, “let me cum in your ass.” She bites her lip and shakes her head yes moaning. That clit hand relocated down a little further. She’s keeping her asshole hot for when I have to fill it. I can feel her knuckles against my balls. She starts with more dirty talk in that super sexy voice of hers.

“I want it. I want your cum baby. You’re gonna give it to me deep in my ass. You’re gonna have to push so hard in my tight ass. I want it to drip out of me. (Grabs her phone) I wanna record it.”

I’m trying to cum as fast as I can now. Completely opposite of the last decade of my life. Watching her touch herself, knowing she had only tried anal play about 45 minutes ago and wanted me to shoot a load up her ass had me throbbing. Her pussy is dripping down lubing her fingers and asshole. Perfect. “I’m about to cum baby” I say frantically. “Put it in my ass!” I threw her legs back facing her ass and pussy up. Her little butthole was nice a wet and so was my cock. I press the head against the rim. She starts rubbing her clit while recording. The head slowly slides in. It was so difficult especially since I’m against the cum clock which is about to happen any second now. I used my index finger to guide it in. Once the tip broke through she moaned the hottest “oh my god, you’re cumming in my ass.” And just like that I started exploding. “Holy shit, I can feel it shooting inside of me. It’s so warm.” I was pushing further and further inside of her until there was no more of me left. “Baby it feels so god damn good.” Her asshole was so tight I didn’t even know if any cum actually came out. Like a kinked hose.

Tiffany is still rubbing her clit when she says “I’m gonna cum with you in my ass” and starts masturbating like it was for a gold medal still recording. She’s strangling my cock which is harder than its ever been in my life. I grabbed the phone so she could use both hands. I reach down and spread her pussy open while releasing a leg. I felt the difference inside of her. Her hips start rocking a little and her breathing gets faster. I couldn’t hold her legs back anymore. Her whole body is convulsing. She couldn’t keep rubbing so I took over. Her asshole was contracting again and I’m not gonna lie, it kinda hurt. There wasn’t a lot of space to begin with. I’m putting a lot of pressure on her clit when she screams out “I’m cumming” about 10 times in a row. It kept going. Her orgasms are about 15 seconds on a normal day. This was almost a minute later. Her abs were flexed so hard she looked like a bodybuilder, but her legs were jello. In the moment I didn’t even notice she squirted on me. One little squirt right on my stomach, and my dick is still in her ass for all of this.

Tiffany’s laying on her back with her heart racing and says “I think I passed out again.” My legs were pretty weak from the half gallon I shot up her ass two minutes ago. I pick her legs up and slowly start sliding my semi hard dick out of her and she says “ohhhh there’s a lot of cum up my butt. I can feel it.” It starts dripping out onto her blanket when she rolls over on her stomach. I took a peek. Porn aside, watching cum drop out of a woman’s ass is fucking hot. “Go turn the water on. I have to be quick when I get up.” I’m in the shower when she comes speed stepping in with her hand covering her butt. She plugged her asshole with a finger so she wouldn’t drip cum on her nice wood floors. I just laughed at her.

We showered and cleaned the sin off of us then slept through the night. Next morning she said her ass was a little sore but she was up for another attempt which we worked on throughout our relationship. More of me and Tiffany to come soon.

Source: reddit.com/r/gonewildstories/comments/8r4z6l/drunk_ex_gets_her_first_anal_creampie_mf