Never Have I Ever

Going out to lunch with an ex has historically been a very surreal experience. Do you shake hands or hug? God forbid you both do the opposite of the other and conduct a weird desynchronized dance of handshake half hug. Callie and I ended on good enough of terms, so we hug and sit across from each other, some slight awkwardness due to her half leaning in for a kiss I wasn't quite prepared for.

Callie looks pretty much exactly the same, and I look as different as humanly possible. Not sure who that really says more about. She's an unchanging stubborn person, and I evolved. Or did I sell out and she stayed classy. Who's to really say?

There is a new piercing on her left ear, and there is now only a single earring in my ear, instead of the four I used to have along with multiple others. Her hair is still dyed in three colors, though never the same three colors, while I let my natural color grow out and got it cut. It's short still, but I'm a brunette for the first time in years.

The biggest difference in my appearance is that I'm six months pregnant, and I have the perfect rounded belly. Quite proud of it actually. A beautiful half sphere.

We talk politely till our drinks arrive, then she's just staring at my stomach. She's confused on how I'm pregnant. Me, the girl who only a few years ago was a butch lesbian untouched by man. That's the part she's trying to figure out. How did I flip?

"You can ask," I eventually say, her snapping away from my dome and finding my face for the first time in about three full minutes.

"What happened to you? Two years ago you had never seen a dick," Cassie said, the best I could muster at the moment was a shrug, "What started it?"

"Actually, it started like this. I went out with an ex, and she had already had the baby and was pregnant with the second. She was like me, the pierced, dyed hair, fat lesbian."

"You were never fat..." Cassie started to say before I jumped back in.

"I weighed more than I do now, and I'm pregnant so don't even try. I asked her what happened, and she said the most fucked up shit I had heard up till that point. She got fucked straight."

"That's not a thing," Cassie said, me laughing at her more than with her.

"She said I should just fuck a guy, and see how I liked it, if at all. I said I could fuck four guys and I still wouldn't like it. She then bet me if I liked it, well then she gets the satisfaction of being right. If I didn't, I got to fuck her again. So I go into this one hundred percent sure I fuck a few guys, then I get my prize, too easy."

"What was the first guy like?" Cassie asked, I can tell she was a little intrigued. Even lesbians get into this, always trying to find crafty ways to get their more curious straight girlfriends. I once had turned flipping straight chicks into an art form.

"You're thinking like a normal person. You're thinking date one, fuck one, date two, fuck two. I wanted this over as fast as possible..."

"You didn't?" Cassie asked, her trying to hide a gag. Why this is puke worthy I don't know, but then again I was once the opposite side of a similar conversation.

"Don't get ahead of me. I put out an ad on craigslist. In so many words it said 'Lesbian looking to fuck four guys to win a bet.' I was expecting this to take awhile, I had twenty takers within the hour. I was expecting the picture to scare more guys off."

Lesbian me had sixteen piercings: four per ear; two lips; two nose; eyebrow; navel; left nipple; tongue with just as many tattoos on my neck, stomach, arms, legs, and lower back with dyed blue and black hair. I wasn't really that fat, more like ten pounds heavier than a healthy pudge but I was definitely not fit.

Twenty guys were on board with that in less than an hour.

"I pick the four, and I had a debate on where we do it. Hotel seems too sketchy, so I ultimately chose my own apartment. It added another level of comfort for me, but I knew the risks, I wasn't ignorant of that."

"You got four guys off craigslist," Cassie explained, like that only was a larger deal. Which it kind of was.

"Didn't say it was smart. Anyway they all show up and they basically draw straws on the order. My plan was simple. They get naked, I fucked them one after the other, and then we're done. I wanted to be defiant and control this, so I wanted to be on top. I'm fucking them, not the other way around. I take my pants and panties off and lube up, and I have no idea how much is right for a dick. Not my field of expertise at this point.

"I straddle number one and I miss like ten times. No idea how hard that could be. I finally get him in, and I slide straight down, way to hard for a first time. I'd been taking dildos and objects for years, how much different could this be? I didn't consider myself a virgin until a man was in me and it hurt. Not terribly, but the fact he was about nine inches didn't help, and I took all of him."

"Did you stop?" Callie asked, concerned that this turned against my expectations so fast.

"No I rode on, fifteen minutes and the pain basically went away, but I was embarrassed. Here I was thinking I was going to ride four guys no problem, and one penetration in I lose my breath. He went in and I felt I was no longer in control. I rode a little, only to realize two things. I'm not good at riding a dick for obvious reasons, and I'm really out of shape. Five minutes in and I'm already sweating, I'm panting, but he's good to go.

"I stop riding, and I look down at him, expecting to see him bored, but he just asked if I wanted him to take over. I wanted to say no, but I also wanted to get this thing moving, so I say yes. He flipped me over pretty quick, picks up my legs at the ankles and goes to work. I feel like a helpless turtle, he's in complete control. He's not fast or going hard, but consistent and with a rhythm. It hurts a little, but that goes away again."

"Then he cums and you fuck the next guy," Callie asked, surprised I didn't put up a fight on being flipped.

"Not exactly. So this first guy, is like a fucking pro. He's got the endurance of race horse, and a big dick which really didn't help the virgin part. He's fucking me for nearly ten full minutes before I realize if these guys are all like this, this is going to be an all day affair. I need to speed this thing along."

"How do you speed this along?" Cassie asked, her imagination answering her own question a moment later. I think it did, her expressions are amazing.

"I call number two over, and I jerk him off. Even this is not easy. My arm hurts keeping it elevated and I overthink everything. Should I do palm facing up or down? Fast or slow? This guy isn't nearly as lasting as the first, he's ready to cum in about five minutes. Then I look at my shirt, and I like my shirt. I didn't want my tits to be a spectacle, so why have them out? I do know that jizz is nearly impossibly to get out of everything. So the shirt goes off, bra is off, tits are free."

"You weren't already naked?"

"Why would I be? I only planned to ride them, for me, not for them. Now I'm naked, and guy number one leans forward and raises my legs higher and he's really deep, deeper than anything ever got, and it's new. It's different, and my tits are flopping now. Didn't realize before, but once they were out, they were out. Now I'm embarrassed again, my armor is gone, so I cover my tits with my arm. Number two says I don't need to be shy, my tits are amazing apparently and he really wants to play with them."

"Did you let him? Of course you did."

"He grabs a handful of boob, I jerk him off until he spills all over my tits. Guy number one is nearing completion and I learn it's a sprint to finish kind of thing. He starts pumping really fast and hard, and I squell. I grip the sheets and as I do I look at number one and it dawns on me no one is wearing a condom."

"Why the fuck are none of you using protection!? Were you on birth control!?" Callie half exclaimed, we're still in a restaurant after all.

"I was a lesbian, why would I be? Before he cums I manage to moan out, 'don't cum inside' and he heard just in time to pull out and jerk himself off all over my belly, snatch, and bush. He's breathing deep, and number three comes rolling into play. I barely even say anything before I give him a half nod and he rams into me. First guy was nice, this guy is fucking me."

"Did you tell him to stop?" Callie asked, not liking his presumption.

"I said slow down, and he did, but he really wanted to flip me over and fuck me doggy."

"Fuck that guy."

"I don't let him, then I start jerking off number four. Number four makes a request as well. He wants a blow job."

"Fuck him harder."

"I was about to say that, before I imagine me going to my ex and saying mission accomplished. She liked to move the goal post in arguments, and I just imagined her voiding the deal because I didn't blow someone. How do you know if you never tried it? I wanted to give her no loophole, no way she could sneak out of fucking me. So I let him put his dick in my mouth."

"Gross."

"Not great, even girls who like sucking dick don't like the taste. His dick is average, so getting all of it in my mouth is actually pretty easy, and I could tell he loved the tongue ring. I'm on my back so his balls are pretty much on my forehead the entire time, so not awesome. Then I realize, this isn't the only thing and I don't want her to have a loophole for. I roll over and number three goes doggy on me, and minute later I came."

"You came?" Callie asked, her expression a mixture of intrigue and sheer terror.

"Not hard, but the fact I did at all scared the shit out of me. Holy fuck, she might be right. But the fact she might have been made me more motivated to prove that was only a fluke. I moaned really loud too. Number four is getting ready to cum, so I'm at crossroads. Where do I take it? Do I make him pull away, do I let him blow in my mouth. Before I can decide he grabs my hair, pulls out and paints my face."

"Gross, ew, ew.."Cassie exclaiming, covering her face and shaking her head, "Why?"

"Number one asks me if I'm sure I'm a lesbian, and I said 'so far I still want to fuck a cunt over you bitches'."

"Nice."

"Number four pulls out and sprays all over my back. Four for four. I'm asked if I won the bet, and I say yes, but she's a weasel. I ask them if there are any other firsts I can do? Never have I ever kind of thing. Number one says first swallow, number two says first creampie, three says first anal, four can't think of anything right off the bat but he'll figure it out.

"Number one is already hard again and he said swallow so he positions for a blowjob. Doggy made me orgasm a little, so I'd like to stay there for a minute and number two positions to drill me from behind. That's when this bet officially turned into a gangbang."

"Holy fuck."

"Number two, the guy who I jerked off, slides into my pussy. Number one, the work horse with the big dick, he drops his dick in my mouth, it tastes like pussy and salt, from when he came earlier.

"They get into a system, I'm rocking back and forth between them, really hard and my tits are flapping in sync with the thrusts. I give him permission to go at it, and number two grabs my hips and uses that to really ram me. It's loud to, I can feel his nuts swing over and hit my pelvis, and for the first real time I'm making some noise. I let out a small little squeak every push, but it's muffled from the dick that's in my throat. Number four I could fit, number one I can't even get to the base, barely even half the shaft.

"Number two starts pounding harder, the movement of me jarring forward causing number one's dick to hit my throat and gag me a little. Something occurs to me right then. Swallowing and anal are self explanatory. As number two is sprinting to a finish, I ask 'what's a creampie?' and he pushes in the deepest and floods my insides."

"You let him cum inside?" Cassie asked, shocked and appalled.

"Miscommunication, but something weird happened because of that. Coming on me was warm and sticky. Inside of me it was like lava. It's not even one spurt, he pulled back a little and I feel his dick swell and pour more in. It was the single most pleasurable thing I had ever felt at that point. I cum again, and hard. It felt so amazing I didn't even complain that I needed to get Plan B tomorrow. I rolled to my back, destroyed by that orgasm, number one keeps his dick in my mouth and I'm working him with one hand

"Something flipped right then. I looked up at number one, and I see something I had never before. I didn't like men so I had never noticed. Number four and three are pretty average, two was a bit of a chubby guy, but kind of cute. Number one was hot. Tall, muscular, after that fuck even I wanted to lick his abs. His dick is huge, and I think I may just love it being on my tongue

"Number four had decided on his first, so he slides under me and I straddle and ride again. Number one's dick is still fighting my face. Number three had said anal, and when he began lining up I figured out what number four's first was."

"At the same time? You got double stuffed," Callie said, then thought about it more, "Triple stuffed?"

"In retrospect, walk before you run, but I did. Number four gets oiled up, and fingers my ass with the lube before he lines up and pushes. The pussy was pretty much instantly in, they slid fast and easy. This took a little pressure, but he got in and I was a virgin all over again. I moan, trying not to yelp. He pulls out and pushes in and I yelp trying not to scream. Him and number three join forces and I full out yell."

"Did they stop, please tell me they stopped." Callie begged, not able to process what I must have looked like.

"Number one turned my face and wide open mouth and muzzled me with his cock. I feel both dicks beneath me, the third in my mouth keeping me pacified. I try to shout but his dick drops into my throat, and I mean my throat. Another first, and I feel my orgasm rising again. Harder than before, and my insides are exploding on these guys poles, and they're just getting starting. I spit his dick out to shout, and nothing I say suggests I don't like it, but he still shuts me up again. Hard to argue with me shouting 'oh my god, oh my god' in absolute joy.

"One thing I learned, when someone has already cum, they last longer the second go, and fuck do these guys. They drill me in every hole for... I don't even know how long. I cum four more times before even one of them does. It's number four who goes first, thrusting up hard one last time and filling me up. He pulled out and away and I feel it oozing out of me. A moment later I feel number two getting ready, I look down and he shoves it in and we're back to three."

"You liked this? This is borderlining rape," Callie said, always one to over exaggerate.

"How? I never said no, they listened when I said slow down, no one is an unwilling participant. To answer your question, I loved it. Number three finished in my asshole and pulled away, finally leaving me to finally give riding a man a real shot. They flip me over so number one balls aren't in his face. Number two finishes and now it's just me and number one. Number one and his amazing huge dick and his incredible endurance. I looked at my nightstand and it was a little after four when I looked, and it was four twenty when I looked back. This guy could go.

"My jaw starts giving up and I stop. 'Are you close, I don't know how much more I can do?' He suggests he fucks me until he's close and then we finish. I agree and he flips me to doggy and goes in, and I don't know how his dick keeps getting bigger. He hits my G every time, so every thrust is like a mini orgasm. I feel it build, and build, and I cry out as I cum again, my legs quivering trying to stay on my knees

"He announces he's getting close finally, and I involuntarily say the most unlesbian thing I've still ever said. 'Please don't stop fucking' He keeps slamming me and I'm begging for more. He doesn't listen, he pulls out and sits on the end of the bed. I look over at him and try to lean to suck but this doesn't work so I do something else very unlesbian. I get off the bed, get on my knees and swallow his cock."

"That pig made you do what?"

"He didn't make me do anything. I get between his legs and down him to my tonsils. He pulls my hair, uses it to pull himself into me, I gag a little and spit it out, drool slithering down my chin."

"I don't think I want to hear the rest of this." Callie nervously said, covering her face again.

"'Be sure to swallow every drop' he says to me as I continue, him still using my hair as reins. I just ask for a warning. I'm working his shaft, I'm flicking my tongue on his tip before I slurp him back in and suddenly I feel him swell and cum without warning. My gag reflex is immediate, I spit it all out on the floor, the rest of him spraying my hair and face.

"'You failed that first' number one says to me. The other guys laugh, and even I do a little. I smile and say 'Who's ready for me to try again?'"

"You did it again?" Callie said, looking between her fingers.

"Number two got hard again first, and I'm glad it was him because he cums the easiest. He maintains that rate and within five minutes he cums into my mouth and I manage to hold it in but when I try to swallow, I just can't. I tried to force it but it nearly made me puke.

"Number four was up and I let him fuck me before he gets close because he'd take to too long. He wanted this fast so he fucks me hard and I'm screaming the entire time.

"He pulls out just as fast and pushes it straight into my throat and lets it go. I pretty much had no chance to not swallow and I manage to guzzle all of him down. I look up at him as I keep sucking and milking him, and he's squirming and pretty much made of putty. The first time I felt powerful since this started. This guy was powerless, I could make him do anything. That's when I realized how women could suck a dick. It's like a override switch."

"Okay, you got fucked and you really liked it. End of story right?"

"Well we rest up and go at it again..."

"Jesus fuck..."

"Sorry but it was overwhelming, but after that I tell my ex and she's smug as fuck. I move the goalpost myself for a change, because I look at her, and I still want to fuck her. I still liked women, and I also liked dick, but not necessarily men. Sex is emotional to me.

I tell another one of my friends that I might want to get dicked every now and then, so she invites me to a threesome with her boyfriend, seeing how I'd be more focused on her. It'll be easier for her if I'm not interested in her man."

"Even I might be willing to let a guy watch," Callie said, slightly relieved to past the first story.

"I fucked her as her man watches for a little, she starts sucking him while taking my fingers, but I can't not look at him. I'm so distracted by him. He noticed me wanting it so positioned himself directly between us, and we take turns. Her mouth, my mouth, before she straddles him and starts riding. I play with her, but I'm still distracted. His dick is going in and out, she's so much better at riding so I'm a little envious of her form, and all I want is to be on top. He's perceptive, and pulls me over to his face where he puts his lips right on my pussy.

"First time a man has eaten my pussy, and it's not the same. Tongue is bigger for one. My friend cums and she rolls off of him, tired and exhausted. He pushed me forward and I land in doggy, and he enters me in one fluid motion, he's wearing a condom so it doesn't feel nearly as good but I still love it. Apparently he had broken the ground rules by doing this, because my friend told him he wouldn't get to fuck me. Maybe play a little but not fuck. Here he was making me cum and I completely forget she's there.