Memoirs Of A Pussy Free White Boy

Shelley was working the drive thru window of a fast food restaurant the night I got set up with her, if set up is actually the correct description of what transpired. I remembered Shelley from high school when I was a freshman and she was a senior so she was a couple years older than me. I think I told the guys with me I thought she was sexy, or something, and that sort of initiated the events that would transpire. I didn't really know the guys that well. We had met at a party, and they needed a ride to pick up something they were really vague about that I was pretty sure was *******. I didn't want to say “no” to them because we had been hanging out most of the evening for some strange reason that only parties can explain, and I wanted them to think I was cool. Or maybe it was because they were black and I didn't want them to think I was a racist. For whatever reason, it was the week of our senior graduation, and I felt we had earned the right to cut loose a little and forget about some minor rules.
Shelley looked good. I had been drinking and smoking a fair amount of weed, but I thought she looked even better than she did back when she was in high school, and I could tell I would have still felt that way even if I hadn't been stoned or *******. She had one of those long skinny bodies that made all breasts look large, but hers were a very generous size to begin with. Her hips looked large because of her tiny waist but they were actually quite small and only held up her pants without a belt because of the way they flared. She had one of those sexy chipped tooth things that white trash girls sometimes have going on with her front teeth, and her eyes always looked kind of dreamy and sleepy even when she wasn't tired or stoned. In fact, she mentioned to us that she hadn't gotten stoned in a long time which was one of the ice breakers that got us inviting her out with us when her shift ended which was conveniently going to be about the same time we were heading back her way. Normally she wore her hair down, and though it looked unkempt, it only added to her sexiness, but tonight it was up showing off this tattoo on her neck that made one of the black guys with me initiate a weird conversation with her. The tattoo was a spade with a Roman numeral inside of it. I wasn't sure of the number translation but it was higher than one through ten.
“I like your tat,” the black guy Dwayne riding shotgun with me told her. She tried to cover it up shyly with her hand which was not at all like her if my memory recalled correctly. She had actually been rather bold and confrontational and had earned herself a reputation as a party girl and then some.
“You shouldn't cover it up, babe. You should be proud of that,” my other new black friend Jeremy told her from the back seat.
“Thanks for our food, Shelley. You look really nice tonight,” I told her when she brought us our food.
“Do I know you?” she asked me. This made my black friends laugh at my awkwardness.
“We went to school together. You were a couple grades ahead of me though.”
“Isn't this sweet, a high school reunion?” Dwayne commented.
“Got any white boys in your life right now, Shelley?” Jeremy wanted to know.
“There aren't any guys in my life at all at this specific moment, fellas,” Shelley informed.
“Well that's just an unspeakable tragedy. Hear that, white boy? You might have a chance,” Dwayne said to me before returning his attentions back to Shelley. “Maybe we'll have to swing by here when your shift is over and make sure you get a ride home, Shelley. When's the last time you got stoned?”
“It's been a while for that too. But I have my own car so I don't need a ride home. Thanks anyway.”
“We can ******* you, make sure you get there safe." Dwayne said with a wink.
“Besides, you don't want to let your friend Billy here down do you?”
“It's Brian,” I reminded Jeremy.
“No, it's not,” Jeremy returned.
“I think he knows his own name,” Dwayne defended.
This made Shelley laugh. “You guys seem really close."
“We just met the white boy tonight, but there's nothing like a pretty white girl to bring the races closer together, right?”
Eventually they got her to agree to let us come by and at least see her off at the end of her shift though it seemed to be at my expense with them making me feel like a charity case and pretty much fixing she and I up like some arranged blind date we were both ****** to agree upon for reasons I can't really seem to explain. I guess my pride was actually a small price to pay for even a chance at a date with this hot babe who also had a reputation for being a bit easy.
Still, the thing about the tattoo was vivid in my mind and something I just had to know about. “What was that thing with that tattoo on her neck?”
“What thing?” Dwayne told me. “It was just a tattoo that I liked. Why does it have to mean anything? You believe a girl has a right to do what she wants with her own body, right?”
“You mean like get a tattoo?”
“I mean like anything, motherfucker!” Dwayne actually sounded angry.
“Yeah, of course.” I answered. I was clearly intimidated which made Jeremy laugh and Dwayne eventually join him. I joined them in the laughter as well once it was clear Dwayne was joking.
“He's just fucking with you,” Jeremy said.
“I know,” I said even though I wasn't one hundred percent sure. “And believe me, I think a girl should be able to do whatever she wants with her own body.”
“I'll bet you do,” Dwayne said. “Are you a virgin?”
“What? No! Of course not, I just graduated high school.”
“It's nothing to be ashamed of, Billy."
“It's Brian, and I'm not.”
“I think Billy's a virgin, Dwayne.”
“I'm not.”
“You should tell Shelley you're a virgin. Girls like her eat that stuff up.”
“She'll probably let you play with them juicy titties. Or kiss that hot pussy.”
“You ever kiss a hot pussy before?”
“Before you go lying, Shelley will know.”
“So have you, or haven't you?”
“She'll know if you're lying about being a virgin too.”
“Tell us the truth, Billy. Tell us the truth and we'll get Shelley to let you play with her boobies, maybe even suck them."
“Maybe we can get her to let you suck that hot pussy."
“Would you like that, Billy? Would you like to suck that hot pussy?”
I had given up trying to tell them my name was Brian and not Billy. “How would you guys go about doing that?”
“The truth first, Billy."
“Fine, maybe I am sort of still a virgin.”
“I knew it.”
“It's alright, Billy. There's a world of opportunity for virgin white boys who don't turn too gay with a girl like Shelley.”
“Trust me, I'm not gay at all.”
“How do you know? Have you ever tried getting it on with another guy, being a bitch boy to some strong masculine man?”
“Fuck no!” I said. “And I don't ever plan to.”
“How do you know? What if you end up in jail sometime and don't have a choice? Would you be one guy's sex slave and do whatever he wanted if he agreed to look out for you, or would you try and fight it and end up getting jumped by the entire prison population on a daily basis?”
“That's totally different. Neither scenario would make me gay if I didn't have a choice.”
“Don't be so sure. Lots of straight white boys go to prison and come out gayer than fuck. Some are beyond gay. Some start dressing like girls...”
“Or keep dressing that way even after they get out if they learned or was taught it in prison.”
“Yeah or keep dressing that way. This one white boy that my uncle turned out in prison has tits and everything, and he keeps coming around giving my uncle all the money he makes working the streets just so my uncle will fuck him up the ass or let him suck his big black dick. It's like he never left prison. He even left his wife and ******* to be my uncle's ho. I think my uncle might have fucked his old lady too now that I think about it.”
“What do you think of that, white boy?”
“I think that's pretty messed up. What does this have to do with Shelley?”
“That's a good question.”
“That is a good question.”
I never did get a good answer to that good question as the conversation got back to my interest in and attraction to Shelley. The guys both insisted they were going to get me those juicy titties and that hot pussy to suck before the night was over no matter what it took. I never once thought to ask them why the conversation never once was about me fucking her. I guess I just took their descriptions as nuanced metaphor.
***
Shelley wasn't exactly happy to see us when we returned to the fast food joint to meet with her when her shift got over. I wouldn't describe her as exactly unhappy either, but I sensed a lot of anxiety like someone who is trying to quit ******* and is then gifted with their favorite choice, and they aren't quite strong enough to get past that dilemma. It wasn't a ******* thing though. In fact I sensed the weed as a soothing factor the moment we sparked up the joint and gave her a couple hits. That seemed to clear her thinking so that between the four of us we could concentrate on more pressing matters like whose place to hang out at so we could smoke more weed while the guys had some more fun concerning my sexual experience and attraction to Shelley simultaneously.
We eventually decided on Shelley's place because even though she had a kid, her mom watched it while she worked and Shelley didn't think it would be a problem calling her and telling her she would pick the baby up in the morning.
“You know what you need, Shelley? You need yourself a white boy who doesn't mind staying home and babysitting for you so you can go out and party a little like you used to.” Dwayne suggested.
He was followed by Jeremy who took it even a step further. “I'll bet Billy boy wouldn't mind doing a little babysitting for a little extra special appreciation on the return home.”
“Is that true, Billy? Are you looking to babysit for some appreciative white girl, Billy?”
She smiled at me in a really seductive way and let the back of her hand move forward and rub against my groin which instantly filled with ******* and became erect. When she smiled at me like she could feel it and knew, I completely lost most of my senses.
“I er... Guess I could er... Fill in for your mom from time to time."
“What a sweet offer. Whatever would you want in return?”
I knew I was being baited. I just wasn't sure for what exactly or how to deal with it. “Er... Nothing,”
“Nothing?! Goddamn, white boy! Can I take his credits?”
“Well... I mean if there are actually credits...”
“Too late, white boy,” Jeremy cut in, “You had your chance.” Then he sat down on one side of Shelley while Dwayne sat on the other.
“Jeremy and I will share his credits,” Dwayne said putting his arm around her.
“If Billy were to rub my feet, you guys would be really building up some credits. They are so sore and tired and I have been on them all day.” She was pretending to talk to them but she was glaring at me and kind of wiggling the toes of the foot that was hanging off her leg she had crossed over her knee.
“Are you deaf, white boy? Get down there and get that shoe off and rub that foot." Dwayne snapped at me in that scary way of his and between that, and the way Shelley just kept staring, I was put under some kind of spell. I found myself down on my knees removing Shelley's shoe, and while I did this Jeremy began to make out with her while Dwayne placed her hand on his crotch. She used the hand to rub Dwayne's cock through his pants. Dwayne unzipped his pants and pulled it out and put Shelley's hand on it. It was the biggest, blackest cock I had ever seen, not that I had seen that many or even any up to that point save maybe for a few sneak peeks in the gym showers in school. Shelley's hand couldn't fit around it, it was so thick, but she stroked it up and down anyway while making out with Jeremy.
“Damn, white boy, stop drooling over my cock and pay attention to the lady's feet.”
Shelley stopped making out with Jeremy a second to laugh, and I vehemently denied any sort of drooling but felt my face burning red with shame as I concentrated on her foot rub. Meanwhile, Jeremy had unzipped his pants to pull out another black cock just as intimidating as Dwayne's. He put his hand behind Shelley’s head and pushed her head right down onto his lap and her mouth opened right up and took his cock right inside. She swallowed it no problem, and then she began bobbing her head and sliding that cock in and out of her mouth, just bobbing her head up and down on it, up and down while continuing to stroke Dwayne. Fed up with just her hand, Dwayne grabbed a fistful of her hair and pulled her over to his cock which she sucked and slobbered with the same skill and enthusiasm she had just shown Jeremy. At some point she decided to take turns on them and began moving back and forth from one cock to the other all on her own, slurping, slobbering and drooling all over them and always using a free hand on the one she had just left rubbing it all over with her drool.
At some point I felt her foot pressing on my hard on reminding me not to forget about her foot massage or maybe even checking for my erection. I had grown hard as a rock watching her service these two black beasts with her mouth and hand. Somehow she unfastened my pants, unzipped my zipper and pulled my pants right down, underwear and all, enough for my little pink hard cock to pop out, and she did it all with the toes of one foot. I started touching myself and she kicked my hand away and gave me a dirty look.
Jeremy laughed. “I think our girl wants you to get your priorities straight.”
I went back to massaging her foot. After a few minutes, Dwayne unfastened her jeans and worked them down her ass and legs with her underwear while she sucked Jeremy's cock. As they reached her knees, he repositioned her by her hips so she was sitting between both he and Jeremy with a hand on each cock and her clothing bunched up around her ankles.
“Get those pants of this slut's legs, white boy,” Dwayne ordered.
I removed her remaining shoe and sock and then pulled her pants and panties down and off her legs. She slid closer to me as she let both Jeremy and Dwayne spread a thigh wide. She had a beautiful shaved pussy that was so wet it was dripping down into her ass crack. Above her pussy was another tattoo like the one on her neck. This was a spade with a crown on it and a letter “Q" inside.
“Nice, isn't it?”
“It's beautiful,” I said. I meant her pussy, not the tattoo.
“Maybe if you ask real nice, she'll let you give it a kiss like we talked about.”
“May I?” I asked.
“You can ask better than that.”
“Please..?”
“Better.”
“Please let me kiss your beautiful pussy.”
“Are you going to do a good job?”
I nodded my head affirmatively like a hungry dog being served a bowl when the bowl was still too high up over his head. She beckoned with her finger and I dove in. It was the first time I ever ate a pussy so she had to guide me, and she did. She told me how to run my tongue up the sides of her swollen puffy lips and around and back down again. She taught me about the clitoris and how to touch it with the tip of my tongue. I made her squirm doing that. That tattoo was right before my eyes and I looked at it a lot. Once I looked up and saw her sucking Dwayne's cock just as his balls contracted and he exploded into her mouth. It was leaking out the corners of her sealed lips as she pulled me to her by my shirt collar and planted a deep passionate French kiss on me pushing most of Dwayne's semen into my mouth. She wouldn't stop kissing me until I was ****** to swallow his load. The guys went wild over this with hoots and hollers.
“Okay, you nasty fucking white boy, out of the way,” Jeremy said, pushing me back and out of it. He climbed on top of her and his monstrous cock sank right into her soaking wet pussy. She moaned and contorted and clawed at his back, and Jeremy sighed and began pumping balls deep in and out of her. I watched mesmerized as Dwayne guided us down into a sitting position onto the sofa across from them. He placed my hand on his cock and had me stroke him while we watched the show. I thought of resisting, but something seemed sinful about causing any possible commotion that might interrupt the show in anyway. I started to touch myself with my other hand, but Dwayne warned me not to.
“You don't want to upset her do you?” I didn't know why playing with myself would upset Shelley, but I trusted him so left myself alone and only stroked him. Jeremy fucked her for almost a half hour while I stroked Dwayne. He finally stiffened and came inside her with a loud groan. He pulled his dripping sticky cock out of her gaping hole with a loud pop. After she calmed down from her orgasm, she saw me still stroking Dwayne which I had forgotten I was doing. I was embarrassed, but felt okay when she smiled at me.
“Why don't you crawl on over there and clean up that mess for me, white boy?” Dwayne said pointing out Shelley's gaping, swollen, stretched out, cum dripping fuck hole. “I hate sticking my cock in something that sloppy.”
I let go of his cock and crawled over to her. She smiled down at me expectantly as Jeremy’s load ran out of her gaping hole and down into her ass crack inches from my face.
“Don't just stare at it, white boy. Dig in like you did last time, only this time, emphasize the sucking over the licking and lapping to get that spooge out of there.”
“You can do some licking and lapping too,” Shelley amended with a smile remembering the job I did last time which made me feel a little better about what should ordinarily have been quite a humiliating situation. I dug in and did the things she wanted along with the sucking that Dwayne expected and after a lengthy duration of sloppy noise making, Dwayne tapped my shoulder and wanted to know how it was coming.
“I think she's clean.”
“I think she's clean, Sir,” he corrected and I repeated, making everyone laugh including myself. His cock sunk into her pussy the way Jeremy's had, and he fucked her just as well until she was screaming out in orgasmic pleasure. He pulled out with the similar popping sound and gave me a slap on the back and told me to dig back in. I did, and Shelley only had to guide me half as much as she did before. This cycle repeated itself several more times before the sun came up until I didn't need any guidance at all and could make her cum almost like they could except with my mouth. At that point, I tried to fuck Shelley my own self but she wouldn’t let me. She said she was too sore from fucking the guys to let even my little peanut inside her. She did let me jerk myself off on her stomach though which I did even though she made me promise to lick it off afterwards which I also did. It was the first time I ever had sex of any kind with a girl past feeling a little boob over a bra
 
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