Milana Vayntrub, My New Girlfriend

Milana Vayntrub is a respected actress and civil rights activist who I have nothing but respect for. She stands for amazing things and seems like a genuinely amazing person. As you may or may not know, she was attacked by hordes of internet bullies who would pm her, tag her in posts, spam AT&T and all around harass her to highlight her acceptingly large bust. I disagree with the actions taken by these bullies and would like to set the record straight. IT IS NOT OKAY TO HARASS FOR ANY REASON. With that said, I respect her and wish her the best, and as a horny teenager I also have fantasies that have a thing or two to do with her. I use this platform as a creative outlet to express those feelings and hopefully entertain others. I of course am not affiliated with her in any way, and this story is completely fictitious. With that said, enjoy. :)

***

"I think I love you."

"I think I do too."

It's a perfect day. Autumn is upon us and it's cold in Boston. The leaves are brown, amber and every shade of fire. The trees are hanging on to their last bits of life as the coming winter strips away the leaves that feed them. Ducks are swimming in the ponds, squirrels are making last minute acorn runs, and birds are migrating south. I'm walking through the Boston Commons with my girlfriend, Milana Vayntrub.

I moved to Boston about a year after our first encounter with each other, and Milana showed up at my doorstep asking to be part of my life. I'm only 20 years old, at least until tomorrow, and I have a famous girlfriend.

Milana and I are a decent number of years apart, about 13. This gets us a few strange looks from people, especially strangers. We hardly see an age gap though, as we both are in the prime of our lives. I'm walking through the park with her, her hand in mine, her head resting against my arm. Milana is wearing a beanie that covers up her naturally beautiful locks of hair. It's a shame that no one gets to see it. She had a drink at dinner tonight, and she's a little tipsy because of it. She stands at 5'3", so she's a bit shorter than my six foot one figure.

We're walking back to my apartment, where Milana says she has a surprise laid out for me. I sure hope she didn't get me anything. I don't particularly like gifts, it just feels selfish to accept them. But Milana seems really excited about it.

"My baby turns twenty one tomorrow!" Milana squealed.

"Yup. I made it to the big leagues finally. Twenty one years old."

"We have to celebrate tonight. It's absolutely imperative." She says with a determined voice before she goes back to her happy, silly mood."

"We just went to a fancy dinner, I think that's celebration enough. Let's just watch some movies at home."

Milana stops and puts some real effort into blowing a raspberry at me.

"Lame! Watching movies the night before your big 21, how disgraceful. We have to go wild!"

I laugh at her insistence. She is so pretty when she's determined.

We make it back to my apartment. It isn't much, but it's home. I walk into the entry room and take off my jacket, hanging it on the coat rack, right next to my Boston Bruins hat.

Milana wraps her hands around my waist and does a tap dance with her fingers on my stomach. This is her signal to say she wants attention. She does it at social events, in public, when I'm watching the Bruins game with the boys.

"Yes baby?" I say as I turn around. I'm expecting to see her pouting and asking me to carry her to bed like she often does.

"I told you we need to celebrate. And I intend on celebrating right." Milana says as she stands there with no pants on. Her hoodie is covering the top half of her body, and her black lingerie is just poking out of the bottom.

"Oh. Oh, OHHHH." I'm just now putting things together.

"Yeah stupid, I meant sex. I meant me treating you tonight."

"Yeah I uh, I could go for some celebrating tonight."

I ran to the bathroom and took the fastest shower I possibly could. Milana didn't join me so I guess that isn't what she had in mind. I trimmed my beard to be as smooth as possible. She says it tickles her sometimes and I really don't want that.

I walked into the living room, only to be hit in the face with a pillow as I did so.

"No looking! I'm going to blindfold you so you can't see."

I close my eyes as I'm told, and Milana ties a blindfold onto me. I'm not too sure what she has in mind, but this seems very interesting.

She leads me into the living room, and guides me to a chair she has set up. I sit down in the chair and await further instructions. Milana, I could feel, draped herself across my lap. She leaned down and touched her lips to mine, wrapping me up in one of her magical kisses. I raised my hands to wrap around her, but she turned them away. We sat there for a moment wrapped in a kiss that made me feel like the luckiest man alive.

"Okay good." Milana said as she stood up, ending our kiss. "Now that I can feel you're hard, I can start the game!"

I would have looked her in the eyes if I could.

"Game?" I inquired.

"I came up with a game we can play. I touch your penis with different parts of my body and you have to guess which part."

"Hmmmmm. How do we decide who wins?"

"You're getting your dick touched, this should already be a win in your book."

"Great point, let's start it up then!"

Milana slowly pulled my shorts down over my cock, springing it up into action. The air is cold and makes me shiver a little bit. I sit in anticipation for what feels like an eternity. Finally something grazes the head of my shaft. It doesn't feel warm, it's very soft however.

"Hair." I say in confidence.

"Okay that was an easy one to start with. The rest will be harder from here on out."

"I'm going to be harder from here on out." I say under my breath as I wait for round two.

Something plump and warm presses against my penis and presses it into my stomach. It can easily be any part of her torso, so it was a shot in the dark when I said,

"Your butt."

"Oh you'd know my butt anywhere. It's your favorite part."

"It's definitely a fan favorite, what else you got for me?"

I sit in anticipation again when I feel something hard stroke down my head. It's cold and makes me shiver just a bit.

"Nipple." I guessed.

"You're really good at this. I'm going to throw you a curveball this round, okay?"

"I'm ready whenever babe." I say with a grin on my face.

I'm sitting with my hands behind my back when I feel her handcuff me to the chair. I go along with it, expecting whatever she has next to be the best thing yet.

I feel what is definitely a pinky finger wrap all the way around my cock. Followed suit by four other fingers. The hand slowly moves up and down, giving me a handjob.

"Your whole hand babe, at least make it challenging for me."

"Oh I made it challenging all right." Milana said as she wrapped her two hands around my shoulders. "Happy birthday baby." She said as she leaned in and kissed my neck.

Ok, so my girlfriend is behind me, kissing my neck, and I'm getting a handjob from someone who obviously isn't her.

"Ummmmm. Who is this?"

"That's the point, you're supposed to figure it out babe." Milana says as she moves on to rubbing her hands across my chest, her breasts resting on top of my head.

The hand has released my dick and spread my legs apart, slowly taking on more and more of my shaft with their mouth.

"Ok well can you give me some clues or something?" I say very confusedly.

"Well it's a favor I called in for your birthday, but this is a woman that you have most definitely heard of before. I asked her not to talk until you figure it out."

I sit in silence for a while, Milana massaging my face with her massive boobs, the mystery person using their mouth and hands to edge me on. My favorite actress growing up was Anna Kendrick, I used to watch movies like pitch perfect on repeat.

"More clues please." I said into Milana's boobs that curessed my face.

"You have to earn one first babe. Why don't you use your mouth to pleasure my boob."

Milana held her boob up to my awaiting mouth. I slowly kissed my way around until I found the nipple. I started by kissing her nipple before I gave it a little nibble. Milana moaned in pleasure. I gave her nipple a little suck and worked my way around the rest of her boob, giving it little sucks here and there.

"Okay you earned a clue. She actually is a tall ginger."

So Anna Kendrick is out of the question, I'm sad but intrigued by who it may be.

The mystery person lets my dick free for a second. Milana straddles me again and slowly slides down until the tip of my dick sits right at the entrance of her vagina.

"Take a guess before I treat you to some of this booty."

"Oh God baby I don't know. I don't know too many tall gingers." I say as I try to buck my hips to get the tip to slide in. Milana moved up with me, robbing me of the pleasure I sought.

"Think of the ones you do know, and don't try to cheat."

"Okay, wild shot in the dark here. Anna Kendrick." (Maybe our definitions of tall are severely differing, and maybe she dyed her hair?)

Milana works her way down slowly. I can feel every bump, nook, crannie, wall and everything in between as she works me inside of her.

"Oh fuuuuck." The two of us say in unison.

The mystery hands reappeared and rubbed my shoulders.

"No babe, not Anna Kendrick" Milana purrs out as she sits for a second.

Damn, that would have been really nice, and really hot.

"Think on a smaller scale. She isn't a celeb."

Well fuck, there are a million and two people who come to mind that aren't celebrities.

I can feel the trimmed cuticles of the mystery person digging as they massaged my biceps, the person's hair draping itself across my neck as she kisses the back of my neck. Milana stops her mounted riding.

"I won't reward you for not guessing sweet pea, you gotta earn it!"

I groaned in agony. I didn't even know where to start with this one.

"The librarian girl with the glasses and the oversized sweaters you're always trying to get me to have a threesome with."

Milana resumed her rise and descent, the mystery person started rubbing the back of my head. Oh my God I don't know which one feels better.

"You idiot, I just said Would you want to have a threesome with her, not we should have a threesome with her. You know she has a dirty side though. No one can be that innocent and adorable."

"So did I get it?" I inquired through anticipation filled groans

"No silly, but I will say that you're close. I'd say you're getting Warmer to these Baked Goods."

"Oh! Claire from that Bakery I really like!"

The hands stop, and she hugs my torso.

"You finally got it! Oh My God I thought I was gonna have to be mute all night"

Holy hot damn I scored big tonight! Claire is the temp worker at this bakery I really like. Not only is she tall, slender, adorable and innocent with rosy cheeks and the most amazing constellations of freckles. She's also a solid 9 on a bad day and she knows how to bake a muffin just right. Always so light and fluffy. It's truly amazing.

Milana reaches her hand behind her, cradling my balls as she massages them with her thumb.

"Congratulations babe! You've won! As a reward you get a little kiss."

I can tell it was Milana. Because the weight on my lap shifted, and she bounced as she kissed me. Milana straddling my lap, massaging my jewels and commandeering my own mouth like an experienced sailor with a familiar sailboat. It was too much for me. I couldn't hold myself back anymore.

I arched back in my chair and lifted Milana a few inches off the ground as I came, blowing her insides with my release. As we settled back down on the ground Milana jumped off to give us both a second. Claire was there at the ready, sitting herself on her knees in front of me. She traced her way around my inner thigh with her index finger, stirring a rising moan out of me.

"Claire I think we should keep the blindfold on him, what do you think?" Milana asked from a few feet away

"Oh totally, yeah! That sounds like way more fun than letting him see. How does that sound cowboy, wanna be blind folded?"

"Umm, No!" I blurted out. "What man in his right mind wouldn't want to see his smoking hot girlfriend and her hot friend when he's banging them?"

"Hmm. interesting point you bring up Jaden. Tell you what, make us both cum first, then it can come off." Claire giggled.

"Can I at least use my hands?"

"Yes please!" They both blurted out.

"Okay deal!"

Claire took my sack in her mouth and did her best to pull it off my body using only her lungs. Milana, I could feel, unclasped my handcuffs and gently guided my hands up and around her neck. I caressed her neck and her chin as I let Claire work to reinvigorate my cock.

I wasn't ready to go yet, so I laid Claire down on the floor, and traced my way around her body. I was looking for anything to get her excited, reacting to the way she shuddered and twitched as I ran my finger around. Her temple, no response. Her lip, she let it drag, holding on for a second. Her neck I caressed for a second as she reached up and used my hand to choke herself for a second. I traced her collar bone and she shuddered. I took that as a sign to use her upper torso against her. My right hand grabbing her ribs and gently rolling her torso around. I could feel her stretch out as if she was trying to escape or adjust my hand placement. Claire was showing her weakness, her breasts. She was dying to have them played with. I could either give her what she wanted or make her wait for it. I bent down and kissed her stomach right above the belly button and slowly made my way upwards. Planting peck after peck I made my way up to her breasts, then backed away and continued my adventure across her body. Claire grabbed hold of my left peck and was giving it light squeezes when I got anywhere tantalizing. Her stomach revealed little to no weak spots, and as I made my way down I took care to not spoil her too soon. Claire oozed anticipation as I circled the perimeter of her thigh and traced my way down.

"Are you going to commit to something in this lifetime?" Claire gasped, she's barely holding on at this point.

I guess I've led her on too much at this point, so I grab hold of her left breast, ease two fingers into her pink folds down below, and pounce on her right boob with my awaiting mouth.

Claire shrieked, and then she moaned.

"Not all at once you bastard." Shudder "That's not fair."

"I'm not looking for fair. I'm looking for effective." I mumble through the breast I have in my mouth.

Claire squirms and shakes as I suck her breast. I can feel her rock hard nipple on the back of my tongue. She showered recently, it tastes like lavender. Her pussy is gripping my two fingers hard. Maybe two to start was a little unfair, but it's too late now.

"I want in on the action babe. Don't leave me out!" Milana says from somewhere behind me.

I can feel Milana kiss gently around my neck.

"Move your head babe, her tits are mine." I hear her say with some degree of ferocity.

I leave Milana to take care of Claire's upper treasures, leaving me to her lower ones. The feeling never gets old, going down on a new woman for the first time. I've done it three times now, and I can vividly remember all of them. I smell saline sweat, which is a relief because I vividly remember the first girl, Jessica, smelling of fish. I was young and innocent and didn't know any better. Plus she had just gotten done cheerleading at the football game. High school was a magical time.

I took my time getting to know Claire. She has a rather pronounced clitoris which made it easy targeting. The first lick made her buck, and the second made her twist left, while the third made her twist right. I kept at it for a second, Claire barely responding anymore as Milana and I worked her up and down. The fiestyness was gone and I wanted to stir it up again. I removed my fingers slowly, and slid them down half an inch.

"What are you doing?" I heard Claire ask as I circled around her butthole with my fingers.

"I'll go slow, don't worry."

"You better! I've never done it before and I don't want it to hurt!"

I kept true to my word as I slowly slid in my finger, only up to the first knuckle. Claire didn't react negatively so I did it again. I pulled it out and slid up to the first knuckle, and then just a little bit more. My mouth resumed its task of pleasuring her more as I slid in and out, long strokes in, short licks around her labia and everything in between. My finger worked itself in more and more, ever so slowly until I could put my whole finger in and twist it in and out. Needless to say Claire melted, and she came not long after.

"One down and one to go!" I claimed triumphantly as I rose from the ground.

I stumbled around until I found the chair I was sat in before.

"Babe, where are you?" I said as I waved my hands around.

My hands smacked against something and I stopped, reversing my hands to try and find what it was. Milana grabbed my hand and pulled me to her.

"Come with me!" she exclaimed gleefully as she grabbed hold of my rock hard dick and pulled me around like a dog on a leash. Milana took me and the chair to the corner of the living room where I could hear her push it into the corner. She leaned on me for support as she stood on the chair.

"Let me lead your face babe." She giggled as I let go of the wall and followed her instructions. She grabbed my face and pulled me closer to her.

I stumbled forward a little until my nose hit something and I stopped. It was soft and warm and it smelt like coconut body wash. Smiling to myself, I parted the two cheeks with my nose and trekked forward through her ass until I hit the end. I could be satisfied with this alone, personally. Her ass cheeks were so soft and all encompassing and squishy and perfect! And conveniently located at head height.

"Baby. I want you to make me scream. Like, seriously make me scream. Okay?" Milana giggled with excitement.

I didn't respond as I reached up and parted her cheeks and buried myself as far inside as I could. My tongue was stretched as far as it could stretch and pushed as far into her as was humanly possible. Like a dog on a leash I tried to get farther into that ass than was possible due to things like physics and shit. Milana was fighting the urge to pull away and rest. She was groaning and I could feel her starting to clench up inside. I pulled my right hand in and without warning shoved two fingers in her tight asshole.

"OOOOHHHHHH FUUUUUUCKKK" She screamed as she absolutely drenched my face in cum. I didn't stop, and kept punishing her delicate resources. She was quaking with euphoria as her knees started to give way a little. I finally pulled back and let her rest as she crumpled into my arms.

My blindfold came off and I took in my surroundings. Claire laid on the floor still, she had a huge smile on her face and she was surrounded by the aftermath of her rough... Everything. The corner where we had been standing had claw marks down the wall, and the chair was drenched. I looked down to find Milana smiling up at me. Her rosy cheeks were the same color of the sunset and her smile beamed radiant light just as bright.

"You asshole." She said with a smile on her face.

"You said make you scream." I smile as I rock her back and forth in my arms.

"Well you made me scream and I applaud that, maybe I'll reward it too."

I held her in my arms as she wrapped her legs around my waist. I slowly led my tip into her and took a second to let her adjust to it.

"Ok. go." She whispered into my ear.

"Alexa, play "Put your head on my shoulder" By Paul Anka." I snap before I move her up and down slowly. We sway around my apartment as she gently rises and falls and Paul Anka serenades us.