My Best Friend's Girl

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

He pulls me tight against his rock-hard, chiseled body. I bite my lip, doing all I can not to melt in his arms. Is this real? It's every fantasy I've ever had. A dream came true. We lean into each other. Our lips draw close. I close my eyes and we kiss. My whole entire world is shattered.

I don't know how long we stayed like this, lost in each other's arms, but it all felt so good. I never imagined in a million years that Derek would want me like this. I want to be his. I want him to take me.

Eventually, we break apart, and he leads me off the dance floor. We run into Nina and Julianne. They mention that Kevin and Jerome had already left. It's been hours since we came here. We all agree to walk back to the dorms.

As we walk back, Nina and Julianne drift off ahead, laughing and giggling to themselves as Derek wraps his arm around my waist. I lean my head against his shoulder.

I look up into his eyes. "Why did you want to dress me up like a girl?"

"Because I know deep down, it's what you want. I saw your secret stash. I saw the look in your eyes when you first saw your reflection. It felt natural and good. Besides, I think you look cute." My face burns deep red, flushing in heat. He pulls me close. "But to be honest, I've had a crush on you ever since I first saw you dress up during Halloween, our freshman year. I can't get you off my mind. I want you just like this. Allen... Or should I say, Alisha, I want to give this a try. I want you to be my girlfriend and I want you all to myself."

I thought I was blushing before... I've all but melted. I bite down on my lip so hard that I can't believe it's not bleeding. He wants me to be his girlfriend... So many thoughts are running through my mind. My best friend wants me to be his. Would he want me to be a girl and dress full-time? What about our families? What would they think? What would everyone think in our hometown and here at school? "Please say something."

I swallow down the lump in my throat. I can't deny that this is something I've dreamed about and now I can have it. I'll I have to do is say yes. I can't say I'm not scared. So many things could go wrong. What if he changes his mind? What if... Life is too short for what-ifs. This feels so right. "Yes. I want to be yours."

He stops and pulls me into his arms, kissing me.

"Damn, that's so fucking hot!" We pull apart to see Nina and Julianne staring at us. Nina winks at me. Derek laughs. We make our way back up to our dorm room as Nina and Julianne follow us in.

"So, ready to lose your virginity as I promised?" Nina asks.

"I... uh..." I honestly don't know. If you asked me yesterday if I wanted to lose my virginity to Nina and Julianne, I wouldn't hesitate, but after all, that's happened between Derek and me, it's complicated.

"Derek's been wanting to fuck you for so long and we want to watch," Nina says as my eyeballs nearly pop out of my head. What did she say? I have to pick my jaw up off the ground before I can answer.

"We don't have to if you don't want to," Derek says.

"No, I want to!" I spit out before I think it through.

They all gasp and Nina lets out a little giggle. "I knew you were a little butt slut."

"I... I don't know. I just, this is all so confusing." I flush red as I drag my hand down my arm.

"Just do it. What do you have to lose?" Nina asks.

"You never know, you might like it," Julianne says.

"If it is too much, we can stop at any time," Derek says.

I take a deep breath. This is all so crazy. And yet, I'm so fucking hot right now. I should just do it. It's Derek. I know he won't hurt me. But what if people find out? This is a lot to think about.

"We'll make sure this stays between us," Nina says.

"Why do you two care?" I ask.

"Because we like the two of you and we think it's so fucking hot. Just let us watch. We won't tell anyone," she says. I can't say I don't think the idea of them watching us isn't arousing. I've never been so turned on in my entire life.

Fuck it. I'm just going to do it. "Okay, let's do it. Just be gentle."

Derek smiles and steps close to me. His hand touches my face, and he leans down and kisses me. A flock of birds takes flight in my stomach. His hand runs down my arm and runs up my back. His tongue slips into my mouth. I feel his hand slip down my dress before he hikes the bottom up. I've decided to let him do whatever he wants with me. I'm just going to go along with it. I trust him.

I lift my arms above my head as he pulls my dress off. He tosses it aside as his hands grab my ass. "Fuck me. I've had my eyes on this ass for so long."

I bite down on my lip. "Really?"

He nods. "I've wanted you so bad. I want to make you mine and after tonight you will be."

My heart leaps in my chest. Strangely, I want to be his. "Make me all yours."

His lips attack mine as his hands conquer my body. He lifts me up and slams me down on the bed. I look up at him as he rips his own clothes off. I get front-row seats to his rock-hard abs.

"Fuck me, this is so fucking hot," Nina says. I look over to see her and Julianne stripping as they rub up on each other. I can't stare for long as Derek tugs down his pants and boxers, letting loose a monster of a cock. My eyes go wide. "You know, if she's never done anal before, she should probably take an enema and I've got some toys you can use to loosen her up."

Nina gets up and grabs her bag before digging out a rubber bulb, some lube, and some dildos ranging in size. My eyes go wide at the size of the last one. She giggles. "Relax, you're not ready for that one."

She pulls me into the bathroom and makes me bend over against the toilet. She fills the bulb up with water, lubes the tip, and before I can protest, it's up my ass, filling my bowels with water. I can barely hold it in as I quickly lift the toilet seat and sit down, pissing out my butthole. That gets a laugh from Nina.

She does that to me a couple more times until the toilet bowl is clear. Then she wipes my butt clean and drags me back into the dorm room. I'm pushed back over the bed. She has me get up on all fours. I look back at her with a little bit of fear in my eyes and a lot of anxiety. "Why don't you try sucking Derek's dick to take your mind off what we're about to do to you? You're way too tense."

Derek smiles and climbs up on the bed and kneels in front of me. He pulls me into a kiss. Suddenly, I feel something round and thin press up against my butthole. I squeal out as it pushes inside of me. Nina laughs. "Relax, that was the smallest one. Hardly the size of my finger."

Derek pulls back from kissing me. "Do you want to try sucking my dick?"

I look into his eyes and swallow the lump in my throat. I'm not going to lie. I wouldn't mind giving it a try. Does this mean I'm gay? I don't know. I don't care. Although, I also find Nina and Julianne hot. I bite my lip hard as Nina pushes the dildo farther into my ass. I look up at Derek once more and nod. Fuck it. I'm already about to get fucked. He runs his hands through my hair and brings his dick to my lips. I can smell his musky, manly scent. The tip presses up against them and slowly I part open my mouth, taking his spongy head between my lips.

I take his dick into my mouth and slowly start to suck on it like a popsicle stick. A moan escapes my mouth as Nina slowly fucks my ass with that dildo. Derek works his dick farther into my mouth.

I can barely take it halfway in before I gag. He pulls back, allowing me to breathe. I drag my tongue up the bottom of his shaft and twirl it around the tip, getting a moan from his lips. "Yeah, that feels good."

It's hard to concentrate as Nina fucks my ass with the dildo. She suddenly pulls out. I try to look back, but Derek has his hand on the back of my head and slowly rocks his hips, plunging his dick in and out of my mouth. My eyes go wide as I feel something a little bigger than the last dildo push inside me. I feel two sets of hands on me as they caress my ass and legs.

"She's got such smooth skin," I hear Julianne say.

"Right? It's baby soft. And her ass is so plump. It's perfect. I could watch her take a dildo all day. I can't wait to see Derek's dick inside her," Nina says.

I don't have time to think about it as Derek fucks my mouth. He pushes it even farther than before, and I choke and gag on it. Tears run down my face. I look up at him, but his eyes are closed as he loses himself in the moment. He pulls out to the tip and I sharply inhale before he slams his dick back in. This time it pops all the way down my throat as my nose meets his pubes. I struggle to breathe. I can feel Nina replacing the dildo with a bigger one. I'm overwhelmed with feelings. At first, the dildos hurt as it stretches me out. She doesn't stop as she fills my ass with the thing. Fuck me. I can feel every inch sliding inside me. She leaves it there before she slowly plunges it in and out of my asshole. It's slowly feeling good.

Derek finally let go, and I fall off his dick in a coughing fit. Nina pulls the dildo out from my ass and gives it a spank. I can feel my ass gaping as the chill air feels cold against my open asshole. "She's ready for you."

This is all a little humiliating, but I'm so turned on. Nina and Julianne step away as Nina pulls out a strap-on and gets Julianne on my bed. Derek pulls me into his lap as he grabs the lube and lathers it over his dick. I grab onto his shoulders as I feel his dick rub down the crack of my ass.

Our eyes lock onto each other. I feel the tip of his cock against my spread-open asshole and I bite my lip. His free hand grabs my hip and I slowly sit down on his shaft as it enters me with ease. My eyes roll into the back of my head as he fills my ass up. I hear the girls moaning, but my eyes never leave Derek's. I lower myself all the way down on his dick. It's a bit uncomfortable at first, but once it hits that sweet spot inside me, it really feels good.

Slowly, I move my hips up and down his cock. The good feelings intensify as the pleasure comes in waves. His hands cup my face before they slide to the back of my neck and bring my lips to his. We make out as our tongues dance between our mouths while his shaft stuffs my ass. My own little cock is hard as a diamond. One of his hands slips down and grabs my ass, giving it a nice spanking. He pulls away and looks into my eyes. "Alisha, you're all mine now."

I bite down hard on my lip as my face burns hot. I truly am his. I can't deny it anymore. Not after spending the entire day dressed like a girl pretending to be his girlfriend. Not with his fat cock all the way up my ass. But what about my family? What will they think? What about everyone back at home? What about his family? And yet, right here and now, none of that matters. I nod. "Yes, I'm all yours."

His smile burns brighter than the sun. Suddenly he rolls us onto my back and he takes my legs and pushes them up beside my head, folding me in half. I melt into the bed as he starts to really fuck me hard. He attacks my lips as he pounds me into the mattress. My moans sing out as his dick sinks in and out of my ass. Both of the beds creek and I look over to see Nina fucking Julianne with a strap-on. She has her on all fours as they both watch us.

Derek pulls my gaze away and kisses me as he plows into me. I reach down and pull at my little stiff cock as his lips take over mine. I'm so close. I'm burning up inside from the friction of his dick inside me.

He pulls back and really hammers me. "Fuck, I'm going to cum, baby."

"Me too," I pant.

"Let's cum together," he breathes and continues to fuck me. His thrusts become wild before he slams into me. I feel him blow his load inside me. It's hot, and it feels good. I erupt between us. We're both grunting and groaning, covered in sweat and cum. He collapses on top of me and I hold on to him.

Then he pulls out and holds me in his arms. "You're all mine now."

I can't deny that.

Thanks for reading my story. Check out my profile for more hot gay sissy stories. Leave your feedback in the comment section below and if you could give it an honest review, I'd greatly appreciate it.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
12 Comments
4Leather4Leather3 months ago

A bet that brought the true sissy to life. Love the story line. Please next chapter

ColonelinguistColonelinguist4 months ago

Well unlike a lot of other commenters, I prefer stories that are short, sweet and to the point. Sure, you could write another chapter or two that address some of the many issues that are already weighing heavily in Allen/Alisha’s thoughts, and it could Obviously become a whole other story.

In the meantime I, like most of your readers now feel sexually sated by imagining what it would feel like to be turned in a fair princess for a whole day, knowing all the time that I no one could hurt me because my handsome black bf is right there to protect me.

I loved the ‘happy ending’ nature of this story.

m1km1n30m1km1n305 months ago

If only everyone had a Derek to have their back, all the while knowing and loving every bit of their “weirdness.” What a lovely story.

The only reason this isn’t a five star to me is Nina and Julianna’s involvement. My surprise that Derek would agree that they could watch him take his girl borders on shock. First, what a crass (not sexy) thing for them to demand knowing what a big deal this was. Second, with Derek’s long and protective history with Allen, it’s beyond me why he would be willing to share his first moments with Alisha with anyone, much less two women they’ve known for only a few weeks. Third, the girls’ flippant and mocking attitude towards Allen at various points in the day was so disrespectful to his experience that I really and truly wish Derek had told them to tone it down or get out—Allen has never been able to stand up for himself so it would have been Derek to check the situation. (In the shower, outing Alisha as Allen to Kevin at the beach without permission, during the enema, prepping him with the dildo, stripping down and fucking while Derek and Alisha had their first time together, etc., so many truly inappropriate moments from these two.)

If you ever write another chapter, please consider reducing the presence of others, and focusing on Allen and Derek learning to be lovers and dealing with all of Allen’s very relevant fears about the reaction of family, friends and strangers alike, and if being a girl full time is what he wants, etc.

I would love to read more about them. Being one’s authentic self is a bumpy and enlightening road. It would be great to see Derek and Alisha walk it together.

Annie_80Annie_807 months ago

Great story! I’d love to see you continue their story.

AnonymousAnonymous7 months ago

Lovely i still remember dressing in my sisters clothes for my friend after school and being his gf. Tasting his cock sucking it and having him cum in my mouth. At school we would sneak off and suck each other off any chance we got and started snowballing with our cum. He asked to fuck me and i said yes and went to my house and i again dressed as a girl and we used a mixture of vasaline and oil as lubricant and i felt wonderful as his cock entered my ass. First time didnt last long and he soon spurted inside me within a few minutes. Soon i got him hard again and got on top and rode on his cock as he played with mine and as he spurted in me again i began spurting onto him. I got off and licked my semen off him and snowballed with him and that was the first of lots of sex we had from then on. SissyErica UK

Show More
Share this Story

Similar Stories

The Man That Converted Me A young man is snowed in & turned out on a mountain getaway.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
Homecoming Queen A high schooler helps a friend who doesn't have a date.in Transgender & Crossdressers
Full Scholarship Naive college kid tries to make ends meet, gets in deep.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
More Stories