Double the Trouble

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My first experience with double penetration.
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"Honey, you know how you said you wanted to have a double penetration experience?" You bring this up nonchalantly, as if it were something we spoke about on the regular. Your hand moved to rest on top of mine across the table.

I looked up from my phone where I had been frantically texting a friend, my brow quirked up in surprise. I slowly set my phone down, my friend all but forgotten. "Yes, I recall this conversation we had in bed... several months ago..." My expression is bemused as to why you bring this up suddenly, in a diner no less. Usually we don't discuss sex at the dinner table, especially something so exotic.

A tiny grin lights up your face as you motion to someone behind you. A man gets up from a table nearby. I'd noticed he'd only been drinking coffee, but I'd figured he'd been waiting for someone, maybe a blind date? Apparently, he'd been waiting for us. I look him up and down, taking in his physique. He's a bit on the burly side, obviously very hairy (as evidenced by the veritable bush poking out of the top of his shirt), and had the cutest nose I'd ever seen on a man. He slid in to the boot beside you, his own lips turning in to a grin.

"You didn't tell me she'd be so pretty," he practically growled as he gave me a once over, his gaze hungry. My face flushed. I was modestly dressed: blue jeans and a shirt that wasn't cut ridiculously low, sneakers on my feet. Yet he was looking at me like I was the tastiest morsel he had ever laid eyes on. I was a bit uncomfortable under his gaze, but you gave my hand a reassuring squeeze.

"Lilly, this is Ernie. He works with me. He heard about your wanting to try DP and offered to be my second," you explain, giving me a salacious smile. You know that sharing is not something I've been entirely interested in, and you hadn't shown any predilection to wanting to share either, so this is all a surprise to me. My eyes narrow a bit, but there's another reassuring squeeze. "I wanted to surprise you." That grin grows a bit as you realize I'm uncomfortable.

"Well, I'm certainly surprised." I didn't intend for my tone to be sharp, but neither of you seemed to care.

The waitress came by and set a piece of pumpkin pie in front of me, topped with whipped cream. I took my hand away from yours and swiped up a dollop of cream on to my finger. I tucked it inside my mouth and I could hear Ernie groaning. My eyes were on you though. You liked your lips, enjoying my little show. My finger popped out of my mouth a moment later, cleaned of the cream. "So," I start, as I pick up my fork to cut off a slice of pie. "I assume you both want to do this tonight?" Nods from both of you. "Alright..." I'm starting to get warm, imagining both of you naked in front of me, and then what you're going to do to me! I could've squealed with delight. My trepidation was melting away as the horny part of my brain took over with a vengeance. I could feel my nipples pearling beneath my bra, pressing against the fabric. I catch your gaze dipping to my breasts as I nibble on my pie. My nipples only get harder under your gaze. Ernie is more earnest in watching my mouth as I suck pie from my fork. I make a show for him, dragging my tongue along my fork. He looks like he's starting to sweat, his mouth slightly open, panting. I finish my pie, slowly, enjoying the flavor of pumpkin and cream. When I'm done, I push the plate away and go back for my cup of coffee, sipping daintily. I know you're both turned on and I can smell the distinct musk of at least one of you. The waitress swings by to clear plates and drop off the check.

"You two want to get out of here?" I suggest over the rim of my coffee cup, a seductive little smile on my face. Ernie nods, clearly turned on.

You usher Ernie out of the booth and stand to help me up from my seat. We pay the bill and head out to our car.

Twenty minutes later, we're standing in the living room of our house. You reach over and push me to my knees. I look up at both of you, licking my lips. "So, who wants to be where?" I ask, reaching for the hem of my shirt to draw it over my head. You two let me strip off my shirt and I can hear belt buckles being undone, zippers drawn down, while I take my shirt off. When I can see again, two stiff cocks are pointing at me. Your long, thick, silk over steel, Ernie's shorter, thicker, wrinkly member. My hands reach for both of you, and you both shuffle forward in to my waiting hands. I stroke both of you at first, enjoying the steel of your cock, and feeling Ernie's getting even harder in my palm.

"Suck me," you command, but I have other ideas. With a coy smile, I lean toward Ernie instead. He sucked in a breath, anticipating what my mouth is going to feel like closed around his shaft. I blow on the head of his penis, it twitches in my hand and I hear Ernie let out a grunt akin to a moan. That spurred me on and I opened my mouth to accept his fat head into my moist chasm. This time he actually moaned and heat speared down my spine, straight to my groin. I squirmed a bit as I sucked him down in to my mouth, almost hitting the back of my throat, but not quite. My fist and mouth moved up and down his length while my other hand continued to toy with you. I was a bit distracted with Ernie, but I can feel you getting even harder as you watch your little slut suck another man's cock.

"I'm gonna cum if you don't stop," Ernie grunted a few minutes later. I could feel everything tightening, he was clearly about to blow his load in my mouth! I pulled back, giving him a sad look, grasping his cock tightly at the base to preventing him from cumming.

"Naughty boy, you don't get to cum yet." I shook my head and looked up to you with a smirk. "You want me to suck you now?" You give a nod, short and curt. I can tell you're a bit upset with me for giving Ernie a blowjob first, but I can't exactly tell you that I as sorry for it - because I wasn't. I enjoyed this newfound game, making you jealous of other men as I lavished sexual attention on them. It was making me hot to know that you were mad, because I knew that I was going to get punished for it.

With my usual eagerness, I moved to your cock and sucked the head in to my mouth. I can't quite fit all of you in me, I've never been able to, but to soothe the sting of my prior actions, I try to take you back farther than I normally do. I gag a bit, my stomach protesting profusely, but I pull back as I hear you let out a deep moan. Oh, you liked that did you? I repeated the action a few times before you pushed my head away. Apparently, it was too much for you too! Who would've thought?

I leaned back on my knees, looking up at both of you. "Now what?" I asked, begging for instruction.

"You should get naked," Ernie said, eager as a high school boy about to feel his first tit. I smirked as I watched you shoot him a hot glare. You were already planning retribution on him. I wondered what your work dynamic was like as I slowly rose to do as I was bid. I unclasped my bra, letting it slide down my arms, revealing my large globes. My nipples were still hard from all of the tension in my body and I could see Ernie salivating for a taste of them. I pushed my jeans down next, revealing that I hadn't worn panties today. Soft brown curls greeted both of your gazes, cut short and neat. "Oh god," escapes Ernie's lips. His cock is twitching, anticipating what he's about to do.

You quickly strip and move over to the couch, leaning back in to it. Your cock juts up proudly, eagerly. I already want to go and sit in your lap, ride you hard, when you beckon me over. "Ernie, you might want to get undressed too," you say as I pad across the carpet. I swing a leg up and straddle you, eagerly positioning your cock at my entrance. Your hands light on my hips, squeezing lightly, but you tell me to pause for now. With a frown, I just stroke your cock a bit while I listen to Ernie get undressed. He's clumsy about it, nearly tripping out of his boxers. I look back to find the man in all his naked glory. He could've been a bear in another life with how fuzzy he was. A thick coating of brown hair covered him from head to toe it seemed, hiding his soft white skin, but accentuating his beer belly. I shook my head and turned back to face you, giving a roll of my eyes at your choice for this. You just wink at me, as if knowing I'm going to like it regardless.

Ernie comes to stand behind me. "I get the ass?" he gasped, even more excited now as he realized that I was going to be riding your cock with my pussy. You nod to him and motion for the bottle of lube we keep tucked away in a drawer.

"Get the lube, she's going to need it. It's a tight fit, even for me." You rub your thumbs over my hips, smiling at my bashful flush.

Ernie stumbles over to the side table, drawing open the door to find the bottle of lube tucked away there. He squeezes a very generous amount on to his hand and lubes his penis.

"Put your fingers in her hole, feel how tight she is," you instruct, grinning as I start to quiver. Another man putting his hands in me sounded erotic, but scary. He didn't know me as well as you did. What if he hurt me on accident? You continued to soothe me with your circling thumbs though and I looked up at you.

I could feel Ernie's fat forefinger pressing against my puckered hole. The lube was cold and sent a chill up my spine. But he forced his finger inside me. I let out a groan as he began to slide it in and out. Drool started to form in my mouth, as it always did when we played with my ass. He added a second finger, making a scissor motion to stretch me adequately enough to fit his cock. By the time he was done, I was a quivering mess, drool dripping down my chin, my arms and legs shakily holding me up.

"Good girl," you cooed and brushed my hair back from my face. You took your cock and probed my entrance. "You ready, Ernie? I think she wants you to fuck her ass."

He's eager and pushes his head against my hole. I try to relax as much as possible, feeling the mushroom passing through my sphincter, in to my hot rectum. I groan out as he continued to push in. Just as I think I can't take anymore, I feel your cock pressing in to my pussy. That groan becomes a yelp, followed by a high pitched keen. My back arches as I'm filled to the brim with cock. I'm gasping in a mixture of pleasure and pressure-induced pain as you pull back out, slowly, trying to get me to adjust.

"That's right, baby," you hiss, gripping my hips tightly as you begin to thrust in and out, in and out. We've done something similar to this before, with a plug and your cock, but it's something else entirely to have a throbbing, real cock in my asshole. "Ernie," you grunt, looking up to your friend. "Go ahead and move."

"I don't know if I can without blowing my load," he says with a shaky voice. His hands rest on my ass, gripping tightly.

"I need you to," I beg on a breathless moan. I didn't want him to cum too soon, but if he didn't move, I wouldn't get the whole experience.

"Alright," he grunted and began to shift his hips, slowly at first. You slowed your pace, trying to match his so that I would be full in my pussy one moment, full in the ass the next. You all keep this dynamic going for a few minutes and I'm gasping before I urge you both to go faster.

"You heard the lady." I'm not sure which one of you said it, but you both start thrusting faster.

"Harder!" I cry out after a few more minutes. You're both grunting with the exertion of fucking me and the pleasure of it. Your motions are choppy, I can tell your both going to cum soon. Is this more of a turn n for you two than for me? It's a question to contemplate later as your hand glides down my hip to brush my clit. I sob out a moan, in the agony of pleasure, as my world explodes in a million pieces. Wetness gushes from my pussy as my inner walls clench at both of you. I'm writhing in pleasure, my arms giving out as I collapse down on to your chest. You continue to rub my clit in quick, concentric circles, dragging my orgasm on and on as I shake against you. I can almost taste your smile as you watch me cum harder than I ever had before.

Ernie doesn't last much longer after that and lets out a sharp grunt as I feel his hot seed spilling in to my rectum, painting the walls of it white. He shakes a bit with the force of his orgasm and I feel him pull out as his dick begins to soften.

You're still pounding away, ensuring I get everything I want out of this - an intense orgasm and cum in both holes. Several seconds later, you're letting out a moan of your own and I can feel you tense up, your hips stuttering as you cum inside me as well. You leave your cock inside me for a minute as we both lie there, panting heavily.

Ernie, it seems, has sat down on the coffee table and is trying to wipe cum from his cock with my shirt. I don't seem to care though, too engrossed in my post coitus cuddles.

"So, you want to set this up as a regular thing?" Ernie asked, tossing my shirt away.

A chuckle escapes you, reverberating in your chest. "We'll let her decide after she recovers. Thanks man, I owe you a drink."

Ernie shook his head, returning the laugh. "Hardly. I think I owe you one after that!" He stood up and began to dress, keeping his gaze on us.

Your cock is still hard inside of me and thrusts a bit as you move around below me. I gasp and moan at the intrusion in my tender pussy and you realize you need to pull out or there'd be hell to pay later. You shift me off of you on to the couch where I lay spread eagle, panting still. Cum dribbles from both of my holes, staining the leather.

You get up, pulling on your jeans to walk Ernie to the door. "Look, I'll let you know if she wants to do this again, but thanks for coming through." You two bro-hug and Ernie leaves. Once the door is closed, you turn back to me, watching me. "Did you like that, Lilly?"

I nod earnestly. "Yes." My voice is breathless, needy. "I need to cum again."

"Anything for you baby," you purr as you drop your pants.

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chytownchytownalmost 5 years ago
Thanks***

For the read.

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