Jolene and Powder Puff Boy

This story is 100% fantasy based and one of the main characters is named after a song.

This story contains details of a sexual encounter between a man and a transwoman, so if that's not your thing, you probably won't enjoy this story, There's quite a bit of playful verbal abuse which includes some trigger words, so if you're sensitive to that, be forewarned.

However, if you ARE into this type of smut, I hope you will thoroughly enjoy...

Jolene and Powder Puff Boy

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Me and Alice often hang out with our neighbor from across the street, Jolene, a transwoman in her early thirties originally from Beebeetown, IA. Jolene moved into the neighborhood about a year after we did. The three of us share a lot of common interests and we often chill on her front porch or ours, smoking, drinking and talking shit.

Jolene was almost six feet tall with a light olive complexion, long, dark hair, a long torso, long, muscular legs and I'm sure everything else was long too. There was just enough muscle on her slender body to make me think, "She looks like a sculpture," every time I got to see her wearing slightly less clothing. She had a sexy, androgynous voice and a slightly exaggerative runway walk, like a model. Most of the time, she dressed casual but sometimes she would get dolled up and either look worked well for her.

I was admittedly a little smitten with Jolene. She was a fun person plus I thought she was sexy as hell. I tried to pitch the idea of a threesome but Alice didn't find her attractive. So the topic has lied dormant in our house since then but obviously, I still see Jolene all the time. I'm never flirtatious with her but in all honesty, she probably catches me looking at her a certain way from time to time.

When she's out there washing her car, it's hard not to look. When she comes home in her gym clothes, she definitely knows I'm looking at her. The first day of Spring, she came out of the house wearing a dress and a gust of wind blew into it from the bottom almost instantly. She caught it before I could see anything private, but seeing her toned thighs, right up to the waistband of her panties was enough for me. We locked eyes and smiled bashfully. We went our separate ways but I knew she knew what was up.

One Friday night, Alice went out of town with her homegirls and I had the house all to myself for the whole weekend. Regardless of whatever story she gave me about what she was doing, I knew she and her slutty, coke addict friends were probably going to be plowing through all kinds of cock while she was away. And that was fine with me. In fact, she fucked around on me often and lied to me about it and for some sick reason, it was the biggest fucking turn on for me.

I would often finger my ass just envisioning big brutish men passing my wife around the room like a joint, busting nuts inside her and so forth. And at the same time, I would often take sexual excursions with other women and always have some unbelievable bullshit story, almost as if I wanted to get caught (I did). She would act like she was blindly accepting my bullshit and while I was away she would fuck the pizza delivery guy or pick up some guy at a bar or something like that. It was a game we were both playing willingly.

Me and Alice were at a weird point in our relationship. This was in the months leading up to when we had the talk about non-monogamy. At this point, we were playing this cheating game instead. I didn't give a hot fuck how many guys she fucked while she was as away. The more the merrier! She could do what she wanted. Besides I had a lot of really important plans for the weekend that included excessive alcohol consumption, LSD and masturbating.

Alice was dressed super sexy when she left the house. Like, almost like a hooker sexy. I was wearing jeans and a t-shirt like always, but underneath it, I was wearing my own sexy little outfit as well and my ass was all prepped for a night of having a wide assortment of phallic objects in and out of it.

Alice was out the door no more than five minutes before I heard a knock. I opened the door and it was Jolene! She was standing there with a mischievous smile on her face wearing a sweatshirt, sweatpants and slippers with her hair in a bun and no makeup. No big deal, right? She probably wanted to borrow sugar or something.

"Hi!" She said.

"Hi!" I said.

"Can I come in?" She said as she walked right into the house.

"Sure," I said as I closed the door behind her, very curious as to what was going on. She had never been in the house before. We usually hang out on her front porch or ours. She stood there staring at me for just a couple seconds, glanced down at my crotch and then back up at my eyes, with that big smile. And then she just walked right up and started kissing me.

I didn't fight her off at all. I did quite the opposite. I grabbed onto her firm little bubble butt and pulled her in close so our hard dicks would grind against each other through our pants as we kissed. And as we kissed, she quickly removed her sweatpants, and pulled out her long, half-flaccid dick. She smiled as she rubbed her bare cock against the lump in my pants with her left hand and gripped the back of my head with her right.

"Suck my dick," she demanded in a low, breathy voice. "You know you want to suck my dick."

She was right. I did want to suck it. I wanted it so bad, I had seen mysteries do it in my dreams! Obediently and eagerly, I dropped to my knees fast enough to cause bruising and urgently stuffed her whole big-ass dick in my mouth and down my throat right there in my doorway, while caressing her smooth, sexy ass. She was almost startled at how quickly and eagerly I rose to the occasion. I wanted to suck her to completion right then and there. But she stopped me.

"Come on," she said, kissing me. "Let's go to the bedroom."

We went back to the room. I pushed her up against the wall to the right of the doorway and started making out with her. My hands were rubbing on her sexy, slender, sculpted little muscle-butt at first but they quickly traveled up her back, beneath her hoodie. She lifted her arms up, I lifted the hoodie off of her and tossed it into the corner (directly into the dirty clothes, by force of habit).

She pushed me onto the bed. She looked gorgeous naked. Her broad, muscular shoulders popped out from beneath shiny locks of wavy black hair. Her flat yet toned chest and stomach and that long, snake-like cock were making me quiver all over. I couldn't wait to take her inside me. She came over to the bed and started unzipping my pants.

"Here we go," I thought to myself, feeling the tight, sexy clothing I was wearing beneath my street clothes pressing against my flesh, exciting me even more. "Wait till she gets a load of this!"

She pulled my pants down just enough to get my dick out and started stroking it, commenting on how big it was.

"Holy shit," she said, sounding deeply impressed. "I knew you'd have a big dick but fuuuuck!"

She started sucking my dick. Her style was to hold the base of it with her hand, wrap her mouth around it tight and suck it really hard on the downstroke, releasing it with a loud pop on each upstroke, while staring me down. Each pop was louder and excited me just a little more than the last. She got herself all worked up and started yanking at my jeans to get them off of me. Once they were passed my thighs, I saw a look of sudden discovery on her face.

"Well, well," she said, yanking the pants off me as if she were opening a Christmas gift. "What do we have here?"

She pulled off my jeans to find that I was wearing blue stockings with little pink ribbons on the front of the thighs. She stopped with her jaw slacked open.

"Oh my God, did you get dressed up for me, baby?" She asked. I laid there in my stockings and t-shirt with my legs spread apart and my ten inch dick slumped to the side over my leg.

"Uhhhhhhhhhh... uh, YEAH!" I patronized. I had no idea she was coming over, I was dressed up for ME >:)

She smiled and giggled as she climbed into the bed on her knees, mounting me. "What do got on under that t-shirt, baby?" She asked while rubbing our dicks together.

I raised my arms so she could take my shirt off, revealing the tight, girly pink half-tank top I had on beneath. She was giddy with excitement.

"Oh my gosh," she said with her hands covering her mouth temporarily. "Look how sexy you are, dressed like a little slut! I never pictured you like this, Dick! I never realized you were a bottom!"

I really wasn't a bottom though. Not strictly anyway. She really did seem to think I was dressed up specifically for her. And now that she was on top of me and flattering me and shit, I just decided to roll with it.

"Maybe I'm not," I said coyly as I rolled onto my stomach, submissively. "Maybe I'm a bottom... for you." The stockings I was wearing really made my ass cheeks pop out and it made Jolene's mouth water!

"Oh my fucking God," she said. "Your ass is so FUCKING sexy in those stockings baby!" She smacked my ass a couple times before grabbing onto it with both hands and plunging her tongue inside me. Pleasantly startled, I let out a high pitched yelp as she fucked my ass with her tongue, smacking her face against my ass cheeks. "Ahh-ahh-ahh-ahh-ahh," she thrusted away at me, using her tongue like a big cock, "your fucking ass tastes so good, baby," she continued tongue fucking me, "you're making me so fucking horny!"

I could see immediately that she was the talkative type, which is something I enjoy. I love when a bitch knows how to talk shit! And this one called me just about every name in the book as she made my ass her own!

She finally pulled her tongue out of my ass and stuck her cock inside me, fucking me doggystyle at first. As soon as she was inside me, the shit-talking commenced.

"Fucking little bitch," she growled as she slid her whole cock up my ass. It seemed like she was trying to ease her way in at first, but my ass didn't need that shit. It needed COCK right away! And it opened up wide to suck her in, right away.

"Holy fuck," she continued. "Your asshole works just like your throat, doesn't it you little hobag?!"

"My asshole is your vacuum, baby," I groaned desperately. "I need your cock so bad. I've needed it for SO LONG!"

I started backing into her, so she would know I could take it harder. She grabbed onto my hips and started slamming into me and I started moaning like a little bitch. The sound of her pelvis smacking against my wobbling ass cheeks made me that much hornier.

"Turn over, bitch," she said after a few minutes of slamming away at me. "I wanna fuck your face."

I turned over and she quickly climbed onto my head, shoved her cock in my mouth and started fucking me in the face. Much to her surprise, I opened up my throat and took her whole cock upon the first plunge!

"Holy shit," she said in a surly tone that she would speak in for the rest of the sex. "Your throat is amazing, baby. It's just like a pussy! Look at you, you little slut!"

She gained momentum until she was slamming her pelvis into my face and therefore her cock down my throat over and over again. And I took it like a champ because I loved every second of it!

She pulled her cock out of my throat, scooted forward and had a seat on my face so that her asshole was on my mouth and her balls were smothering my nose.

"Suck my asshole bitch!" She ordered. "You love it when I prevent you from breathing with my balls, don't you? So all you can smell is my balls and all you can taste is my asshole, you dirty motherfucker!"

Her hole tasted like strawberry flavored farts and her balls smelled like she had spent a lot of time jogging that day. Very pungent. Very aromatic. Very delicious. Just as I started to really run out of breath, she scooted back and said "Now suck my balls."

I sucked her whole nutsack into my mouth with an obnoxiously loud slurping sound and a kept sucking and sucking as I held her stare, like a breast feeding baby. Her ball-sack had the same funky, vinegary taste as the smell they gave off. For maximum flavor, I stuck my tongue all the way out as I loudly sucked and slurped away at her funky, jogger, gym balls so that the tip of my tongue was inside her asshole while her entire scrotum was in my mouth with her big cock bouncing off my forehead.

She responded by grinding her lower half into my face even harder and moaning loudly, "Who knew you had the mouth skills of a dirty, dick sucking, asshole tongue fucking whore?! I love it! This is like riding some sexy amusement park ride!"

She scooted forward and barked, "Tongue fuck my asshole again, you little slut!"

I did as I was told with a big smile. She started getting really excited. She grabbed onto my face and started bouncing as my tongue went in and out of her asshole like a cock. She was about 175 lbs, a healthy weight but quite heavy for someone bouncing on my face. I didn't mind though. The discomfort made it more exciting.

"You suck it so good, you little whore," she growled. "I wonder if you're better at sucking asshole or sucking cock. What do you think?"

I tried to answer her, although her ass completely muffled my words.

"Well, only one of way to find out!" She said right before she scooted back and shoved her cock down my throat again. She squeezed onto my hair as she fucked my face, each thrust deeper than the previous one, faster and faster. And as she became more excited, she got louder and more talkative.

"Oh fuck yeah baby," she said, completely in her element. "I love how I can fuck your throat just like an asshole! It's so good, baby!"

Then she abruptly pulled her cock out of my throat, scooted back down, held my legs up and started fucking me in the missionary position. It was so hot watching her fuck me, making my hard cock bounce up and down with each thrust. She leaned forward to plant a big, sloppy kiss on my lips.

"Mmmmm," she purred. "Your mouth tastes so much better now that it tastes like my asshole and my balls!" She kissed me again, "You love the taste of my balls and my asshole, don't you, you naughty boy?"

"Yes baby," I replied in that breathy, feminine voice one uses when they're answering questions while getting fucked up the ass! "I love the taste of your balls and your asshole. You're fucking delicious! And I hope my upper lips smells like this forever!"

"Oh FUCK yeah," she growled, fucking me harder now. Once again, she grabbed onto my legs, but this time she held them back so my asshole was pointed up and my cock was pointed at my face. Now, she was standing on the bed, pile-driving me with my knees touching the pillow my head was on, all while ridiculing and insulting me!

"I love fucking big tough faggots like you! Trying to act like you're straight? You think people think you're straight? Nobody thinks you're straight, sissy boy! You should just admit you like cock! Everyone wants to fuck you in the ass, you should just let them! You want to, don't you, you little butt-slut! You want everyone to fuck you in the ass, don't you? TELL ME!" She screamed as she fucked me.

"YAAAZZZ" I responded aloud.

"Say it goddammit!!!" She shouted, slamming my ass harder.

"Oh fuck I WANT EVERYONE TO FUCK MY ASSHOLE!" I screamed.

"You like how I fuck your ass you little cream puff???"

"YAZZ BABYYYYY!!!" I shouted as I continued to let her pound my asshole. She pulls her cock out and sticks it in my mouth again, holding my head as she fucks my throat.

"You like the taste, don't you?" She hissed.

"Uh-huh, uh-huh," I obediently answered as I sucked.

"You sick little bitch," she said right before she pulled her cock out of my throat SSLLOOWWWWLY this time and sat her ass back down on my face. Instinctively and eagerly, my tongue re-entered her asshole. She grabbed ahold of her big and jerked it hard and fast as she yelled "Eat my ass bitch! EAT my ass bitch! EAT MY FUCKING ASS YOU BITCH!!!"

I savored every sweet second. The taste of her asshole was almost as sweet as the feeling of being her little bitch for the night. Watching her get off that hard and knowing I was the one to make her feel so good was beautiful and reaffirming. I wore her insults like I would wear her cum - proudly and with honor! I was so glad my ass and my throat made such satisfactory receptacles for her. And even though I had initially dressed up to jerk off to myself in the mirror, I was glad someone else thought I looked sexy in my little getup; sexy enough to fuck like a piece of meat!

"You look good taking a cock up the ass, you little powder puff!" She continued to verbally abuse me, to my sheer delight as she lifted my legs up and re-assumed the pile driver position.

"Ooh, I'm gonna call you Powder Puff Boy! How do you like that? How do you think your wife will like that, POWDER PUFF BOY!!!"

She shoved her cock back inside my ass and fucked me hard and fast. By now, we were both breaking a sweat, panting and moaning louder and louder and louder as we both built towards climax. I had many masturbation fantasies and dreams about Jolene (same thing I guess) up to this point, but never in my wildest ones did I think she would be so loud, so aggressive or so domineering. I always pictured myself as the top. But it was so hot that she turned the tables, I probably liked this outcome better!

As she fucked my ass, I started shooting loads of cum out of my cock. I grabbed ahold of my cock and aimed it towards my mouth, screaming with pleasure.

"Oh fuck yeah baby, cum for me!" She squeaked as she fucked me faster. "Cum for me Powder Puff Boy! I'm gonna fucking fill your sissy ass UP!"

"Fuck yeah, I want you to cum in my asshole!" I squealed as she slammed into me one last time, shooting three thick, hot loads all the way up my ass right before she pulled it out and jerked it right in my mouth along with my own. We pressed the heads of our dicks together as we both diligently jerked every last drop of cum out of ourselves, into my mouth, screaming "YEEAAAAAAAAAAAAAAAAAAHHHHHH" the entire time. As she started to run out of cum, she stood to her feet, with one foot on either side of my head, jerking the last droplets of cum onto me, panting and jolting. She stood there looking down at me with her dick twitching for a second.

"Don't swallow it yet," she said.

She got back down on top of me and we started making out so she could share in the thick, flavorful delight that was our intermingled semen and asshole juices- the taste of US. Then she collapsed to my side, laying in Alice's spot on the bed. We both laid there catching our breath for a minute or two.

"Mmm, I like misbehaving with you, Powder Puff Boy!"

"Me too," I panted. "That was amazing."

"It was," said Jolene. "I had no idea you were such a dirty girl!" She laughed.

"Guilty as charged!" I said in a faggy voice. We both laughed a little before I continued, "In all honesty, I think about fucking you all the time, but I never really pictured it like this!"

"What do you mean?" She asked.

"Well, I always pictured myself as the top."

"Oh yeah," she giggled. "I did too. When I was walking over here, I totally expected to be walking back bow-legged!"

"Don't get me wrong though," I said. "I totally loved bottoming for you just now. Especially the part where you sat on my face and made me suck your asshole. I'll be jerking off to that thought for a long time!"

"You eat ass better than anyone out there, Powder Puff Boy!" She said. "You must be really into it!"

"I'm actually an addict," I said. "I'm an ass-sucking asshole addict with no days clean!"

"Mmmm, yesss," she said, seemingly starting to get worked up again. "I love that you'll suck my cock right after I pull it out of you! Do you like the taste of your own ass?"

"I love it," I admitted. "But I would rather taste yours!"

"Mmmmm, again," she giggled excitedly.

"Oh yes, again and again baby," I replied.

With a flattered look on her face, she turned and rolled her beautifully sculpted body onto me in the 69 position so that her cock, balls and asshole mere centimeters from my face, once again.

We feasted upon each other's assholes, cocks and balls like half-vampire/half-pigs for the next 30 minutes. Neither of us could get enough of the other's taste and stink. It was glorious!

"Is it too late for me to fuck you?" I asked as I held her slimy, wet asshole open right up in my face.

"Of course, Powder Puff Boy!" She responded. "I thought you'd never ask!"

Quickly, she dragged herself down into the reverse cowgirl position, grabbed onto my cock and stuffed it up her ass. As much as I had lubed her up with my tongue and as relaxed as her anus was, she still needed me to ease it in, nice n' slow like. It was hot watching my thick, dark-brown cock slowly enter her firm yet round off-white ass from this angle. Within a few minutes I was in and she was riding me fluently.

"Oh fuck," she yelped helplessly. "Your fucking cock is so thick! I can feel it fucking stretching my asshole! Stretch me Powder Puff Boy!!!" As she bounced and bounced and bounced.

It was amazing. It was hot. It felt great. And yet, as much as I enjoyed watching my big cock stretch her asshole from this angle, I felt like I was missing out because I couldn't see her pretty face. Nor could I see her gorgeous cock.

"Turn around," I said. "I want to see your face, baby."

She bounced and bounced until she bounced right off of my cock, immediately turned over and started sucking it. This time, she sucked it really fast, which is my favorite way to get my dick sucked. She stopped to lick it from bottom to top. And then she sniffed it.

"Mmm," she said. "It smells so good," she licked it again. "Tastes good too. I love the taste of my own asshole!" She continued sucking for a minute and then hopped back on, this time in the cowgirl position, facing me. Now I could watch her cock bounce up and down, which is just what I wanted.

She bounced harder and faster than I've ever seen someone bounce on my cock before! From the intense slapping of her cock against her stomach and mine, I figured it must have hurt to some extent, but Jolene was clearly enjoying herself. She was grunting angrily between orgasmic squeaks and squeals but she was clearly enjoying herself very, very much! So much so that her cock started shooting loads of cum right at me.

First she splattered my chest. Then she almost shot my eye out with it. Finally, she just sat down on me, so that my cock was all the way inside her and jerked the remainder of cum out of her cock into her hand. When she did that, I came inside her - 10 inches inside her. As we both came, I rubbed her cum all over my chest and stomach and licked it off my hands. There was SO much of it!

"Oh my God," she groaned, still sitting on my throbbing cock. "My ass is so full of your cum right now."

"I wanna taste it," I said. "Sit on my face again."

Slowly, she got up off of my cock and dragged herself forward, leaving a trail of ass-cum leading from my crotch, up my stomach. Holding her ass cheeks open, she sat on my face and emptied my cum from her ass into my mouth. When she was finished, she hopped off of me and off of the bed. She crouched down beside the bed, giggling giddily, and made out with me again so we could swap ass-cum.

"Well," she said conclusively. "I think I better get outta here, Powder Puff Boy, otherwise I might never leave. We wouldn't want your wife finding me asleep in bed with you, now would we?"

I would have laughed out loud if I wasn't so tired.

"My wife is with her friends, sniffing coke and rimming groups of rich, Persian fashion moguls. I really doubt she even gives a fuck!" I said, frankly.

"Wanna know something, Powder Puff Boy?" Asked Jolene.

"Huh?"

"I know." She admitted.

"You know what?" I asked.

"I know she's out fucking other guys and I know she doesn't give a fuck that we just had sex in your bed!" She answered.

"What? How???" I asked, dumbfoundedly.

"She dared me to come over here and fuck you!"

The end...?