Giving in to Femininity

Story Info
Shane/Sarah takes the last step towards femininity.
4.3k words
4.7
28.7k
41
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

I giggled as the blindfold was put in place and I felt my wife behind me. I was kneeled down on the floor right opposite the edge of our marital bed. She was giggling too. The tension in the air was not only palpable, but immediately evident.

When you're blindfolded, they say your other senses are kicked into high gear. And so it was with me, I could smell the excitement in the air and also something very musky. I could hear footsteps that I was pretty certain was not my wife's. And I heard something move on the bed. Was someone else there? What had I gotten myself into?

To answer part of that, we should probably rewind a few months. My wife and myself were always pretty kinky from the start, but off late we've been exploring some things that normal people might consider taboo.

We've been getting into feminization play a lot lately. For the uninitiated, feminization play is when you take a regular man and give him feminine experiences. It started with panties, and maybe bras, some shaving, some make up. Pretty harmless right? It then escalated rather quickly to buttplugs, dildos and rim jobs.

The craziest thing we did was use a double ended dildo to fuck our brains out. That was two weekends ago. Tonight was our anniversary, and we had planned a special night. The best lingerie for us both, some wine and a bed full of rose petals. That at least was my surprise to her. She had other things in mind for tonight.

I'll never forget our first trip to the lingerie store to buy matching panties for the two of us. Since then it's been a slippery slope to femininity, which had no end in sight. And that worried me.

"Where do you see this ending?" I asked my wife Christina in bed one night, maybe a month ago. Christina and I started dating a year before we got married, in a whirlwind romance. We both thought we knew each other well enough and agreed to go on this adventure together, but had no idea where this would lead.

"Well, I don't know babe. You tell me. We've been running the gamut in terms of feminization play. We both agreed that we didn't want to resort to cuckolding in the traditional sense or humiliation. Where do you see yourself being satisfied with this fetish?" She asked me as she stopped scrolling on her phone to look at me with her blue eyes and blond hair. She was only five foot six inches tall, but she was drop dead gorgeous with her ample breasts and a sexy butt that I fell in love with instantly.

"I. I don't know. I mean I really like what we're doing and I want to keep doing it but I guess it bothers me that I don't know where this is going" I said.

I on the other hand, was five foot eight inches tall, a scrawny star trek nerd with jet black hair and pale white skin. It had been, at least in my mind, a miracle that Christina fell in love with me, given she could have any man she wanted, but she claimed I was just her type.

"Well, Sarah, it doesn't need to end somewhere or anywhere. It's okay that you don't know where it's going because sometimes you won't! That's life! All I can say is I really love exploring your new found femininity with you. Plus that ass of yours is irresistible in a lace thong and you know it!" She said using the feminine version of my name Shane. For a lot of our play sessions, I had been going by Sarah.

"You're right. It shouldn't matter. But out of curiosity, what do you think is the height of femininity? When do you feel like you're at your most feminine?" I asked her.

"Okay." She said taking a deep breath. "This is going to sound super misogynistic and kinda toxic but" she began, "I feel the most feminine when I'm submitting to a man. Like when he has me bent over, exposed, and at his mercy, that's when I feel truly feminine. I know, it sounds horrible but I can't help it" she said blushing.

That sounded more erotic to me than sexist or misogynistic and I could feel my boner grow in my pink bikini briefs.

"Wow. Um. Tell me more?" I said trying to egg her on.

"It's hard to describe the feeling but it's almost like giving up all pretense of trying to be in control, it's when I'm at my most submissive, and it really feels primal in a way, like this is how women are supposed to be, supposed to submit to men. Any feelings I ever had of any masculinity or feminism or even sense of self worth are wiped away the minute I beg him to fuck me and use my holes just for his pleasure." She said giggling as she turned pink.

My boner couldn't hide itself anymore and started to stick out.

"Oh. Looks like someone is getting excited?" Christina said referring to my boner and raising her eyebrows.

I took a deep breath and said softly "I want that."

"What?" She asked as if she didn't hear me.

"I want that. I want that to be my endgame. I want to experience that level of femininity. " I said as she smiled.

" Well my slutty little girlfriend, I can definitely arrange that. I can help you work towards that. But you have to trust me. Completely. Do you trust me?" She asked.

"Yes" I had answered that night before she brought out her dildo and made me cum in my panties.

"Do you trust me Sarah?" She asked me now, as my thoughts wandered back to the present where I was still blindfolded, wearing a red lingerie set complete with red lace bra, red lace panties, garters and thigh highs.

"Yes" I said once again.

She nibbled on my ear as she could feel my anticipation rise as well. "Babe you know how you've been saying you wanted a real man to make you feel like a woman?"

"Uh hmm" I managed to say as I could feel a chill down my spine. It couldn't be, could it? She wouldn't bring a whole other person in to our bedroom without initiating a conversation with me?

She removed my blindfold as I was now face to face with a well built man sitting on our bed, wearing nothing but boxer shorts. He seemed tall, and had light brown skin and black hair.

"Well, I may have a small little surprise for you. This is my ex boyfriend Kevin from college. I told him about your needs and your tight little pussy and he was more than happy to help. "

"Nice to meet you Sarah." Kevin said in a low growl. I could make out the outline of penis from his boxers.

"So. Do you like your present? Do you want to try it on? You know you want to. Your panties are getting wet aren't they?" Christina said as she whispered in my ear.

It was true. I was a little shocked at the scenario but I was incredibly turned on. I was leaking pre cum in my panties.

"Hi Kevin" I said in my sluttiest voice possible as I blushed.

"Aww she's feeling a little shy. Well don't worry Kev, she's really eager for some good cock and well, yours is one of the best. " She said winking at him.

She lowered her voice to a whisper and said in my ear. "Beg him. Beg to suck his cock. He'll love that and it'll reinforce your sluttiness. " She said with a tone of lust in her voice that I had heard only once or twice.

My head was swimming with lust, longing, confusion and fear. I was very vulnerable, dressed in lingerie, on my knees in front of a strange man (who used to date my wife!). Yet I was more hornier than I had ever been, and I was filled with this desire to be slutty, this craving to submit to this man. This, in short, was everything I wanted but didn't know I needed. I had a choice, or it seemed like I did, of asking to suck his cock or not doing so.

In reality, I didn't have a choice. My body and it's desires didn't leave me a choice, this was the natural endpoint of my exploration in femininity. And I was going to go for it.

"Please Kevin. Please can I suck your cock? Please can I submit to your big thick cock and slobber on it like the little slutty little girl I am? " I said as my hands, trembling slightly, moved over to the waistband of his boxers.

"Of course Sarah. Let me help you with that." He said as he removed his boxers to reveal his semi erect penis. It was quite big, and girthy. Definitely bigger than my own by quite a bit, and smelt musty and funky but not in a bad way. He smelt like a man, a real man and it only served to make me want it more.

I had obviously never done this. Christina teased me a bit in the past, by telling me she would take me to a glory hole but this was the first real penis not made of silicone or attached to a harness that I was going to take.

I kissed the tip gently before opening my mouth and taking the head, trying to make eye contact with Kevin. Kevin looked down at me with his big brown eyes while I tried to swirl my tongue around his bulbous head hoping to elicit a reaction or even a sign of encouragement from him.

Instead, I got both from Christina who was by my side on her knees too, whispering words of naughty encouragement in my ear.

"That's it babe. Just like that. You want to get it nice and wet for him so he can fuck you good later tonight don't you? That's right. He's going to take your virginity and make you feel like a real woman, just like you wanted. " She said licking her own lips in desire. Was she as turned on as I was?

While I continued to suck Kevin's dick, taking him deeper and deeper in my mouth, my brain started wandering to the practicality of it all. I was slobbering on my wife's ex boyfriends penis. While she had never been one to compare, or even brag about her sex life before me, I always got hints that she had a slightly salacious past than she had let on. And let's be honest, in a contest of size, Kevin had me beat easily. He was definitely at least double my size, maybe even thrice of you considered girth. With a beast like Kevin before me, was Christina really happy with our sex life before our feminization play? Was she always craving something bigger?

As if sensing my trepidation, Christina whispered back "Shush babe. Don't overthink. Just go with the flow. We all know you want this. You want to submit to his cock. And it's a tasty one isn't it? Wait till you feel him inside you. " She said as I started to take him deeper in my throat, trying really hard to take all of his shaft before choking.

"Aww little slut. It's okay, we all choke sometimes, the trick is to relax your throat muscles and breathe normally. You got this. Do you mind if I kiss him a little to keep him going? I'll come back to encourage you in a bit." She said as I mumbled my approval through a mouth full of cock. If I was sucking on her ex boyfriends cock, I thought it was fair that she could kiss him, plus she did ask permission, even if the boundaries of our marriage were being broken down in front of us, at least we both consented to it.

"Hi Kev. I may have missed you and your cock just a little bit." She said as I heard a smooch noise. I looked up to find Christina on Kevin's thigh, sitting almost childlike, kissing him. She had on lingerie very similar to mine, except in black.

"Mm. I kinda missed you too, though I gotta say your little girlfriend here is a pro. You taught her your tricks didn't you?" He said in between smooches.

I meanwhile had become "Cock drunk" if that was a real word. I had become obsessed with Kevin's cock, as I felt all inhibitions disappear behind my lust and desire. The situation itself, which minutes ago felt awkward (I mean I was in lingerie sucking off my wife's hung ex while she was on his lap making out with him?), had begun to dissolve in my mind as I only thought of one thing. Cock.

I had begun to slobber almost mindlessly, leaving a trail of pre cum mixed with my own saliva as I started to go as deep as I could. One hand strokes his engorged shaft while the other went inside my panties as I stroked my own. The difference in girth between us was night and day, my wrist could barely wrap around his shaft completely, while I was capable of stroking myself off with just my fingers, like it was a clit.

I had brought him to his edge as he said "Stop Sarah. I can't. I need a breather before I cum. Im not done yet though. " he said as he lifted Christina off his lap easily, and sidled back getting comfortable in the bed, leaving me on my knees, pre cum leaking through my panties, my face a mess with his pre cum and my slobber.

Christina walked towards me and helped me up.

"Let's get you ready for him shall we? Tonight is going to be all about you. At least the first round. I may want a ride too, if it's okay with you. But I'm getting way too ahead of myself. Let's get you ready for him!" She said as she took my hand and pulled me close into a embrace and started to kiss me.

She immediately spanked me hard and said "Kev, you're going to love spanking her! Her ass is what I wish I had!" She said as she grabbed a fistful of my ass playing with it as I moaned.

"Is that so? Maybe we should see which of you girls is a better fuck tonight? " Kevin said with a wink as he stroked his cock to us.

"You're on! But let's get Sarah her ready first" she said as she pushed my torso down and made me bend over yanking off my panties, exposing my ass to Kevin.

"Whoa. You were right. That is an exquisite ass. Don't stop on my account. Let's get you both naked, why don't we?" He said with a menacing smile on his face as Christina started to apply lube to my butthole or pussy. I moaned as Christina fingered me.

"Down girl, just easing your hole up for his monster. Let's take your bra off too, then you can undress me" she said as she unclasped my bra, leaving me in garters and thighs. My penis or clit was standing at complete attention, betraying any sense of denial I had about how the situation disgusted me. Because the plain truth was I loved every second of it so far.

Christina stood in front of me with her back to me bent over similar to how I was a minute ago. I peeled off her panties to reveal her glistening pussy. This was turning her on as much as it was turning me on. I took off her bra, leaving her in the same nude state I was in.

It should be weird, me and my wife, both naked and exposed in front of her ex boyfriend. But it didn't feel that way at all. It felt like two cock drunk sluts who would do anything for good dick. And maybe that's what we really were.

Christina took my hand and whispered in my ear "You'll want to beg for his dick again. Beg him to fuck you, beg him to use your pussy, beg him to take away any masculinity you may have had left. Go on. " She said as she led me to the bed and guided me to get on all fours while she stood behind with Kevin, positioned near my rear.

"Please Kevin. Please fuck me. Please take my virginity and ruin my tight slutty little hole" I said in my most desperate voice.

"Of course" he said as I felt him come closer to my exposed hole. Christina lay right next to me on her fours too.

I felt his dick circle my hole before entering my sphincter, nearly stretching it to its limit.

"Fuck" I said as I rolled my eyes in pleasure as well as pain. The dildos I had played with had not been this big.

Christina was back to whispering in my ear with her verbal teases.

"Shhh. It's okay. It hurts now but it's going to feel sooo good later. Just let him stretch you out. That's it." She said as I felt Kevin's hands around my hips leveraging them for grip as he started to thrust.

"Fuck. Yes. Yes. That feels good. " I started to moan as he started to build a rhythm.

"Fuck this girl is tight. You were right Christina. Such. A. Tight. Fuck" he said punctuating with grunts and thrusts.

"I know right?" said Christina as she sidled up to him and kissed him, a sight I could clearly see in the bedroom mirror in front of us.

I meanwhile was close to tears. The pleasure was lighting my brain up in ways I couldn't imagine. He was hitting some spot inside me that I had never been able to reach leaving me to be a blubbering moaning mess.

"Fuck. Yes. Fuck. Just. Fuck" I managed to say before devolving into moans and whimpers.

Christina meanwhile continued to whisper teases into my ears.

"See how he's breeding you? With every thrust he's making you more and more of a cock hungry whore. But you love that. You were meant to be this. A little slut who would bend over for the best cock. Doesn't he feel so fucking good? He used to hit me in places I didn't know I had, I can only imagine what he's doing to your pussy. And your little clitty has been trembling this whole time, like it's on the edge. Should we help it along?" She asked me.

"No. Please. Just. Let. Him fuck me." I managed to say as I could feel him get me close to the edge with no help or stimulation of my clitty.

With a couple more thrusts I managed to scream "Fuck. I'm coming. I'm coming. I'm coming." I said as I felt the heat in my clitty and it started squirting on its own leaving ropes of cum on my thigh highs.

"Fuck. That's hot. I think I'm going to " Kevin began as I felt him thrust one last time before I could feel him grunt and his shaft vibrate in my hole filling it with warm cum.

Kevin pulled out, making me moan once again as my hole, now utterly destroyed and leaking with his cum, exited me, leaving me still on all fours unable to move out of a mixture of shock and exhaustion.

"Fuck. That was fucking hot." Christina said as she used some of her fingers to lick some of the excess cum off my thigh highs.

"Yes. Fuck. I'm sorry Chrissy, but your slut has tired me out. I need a nap. " Kevin said as he laid back on the bed with his arms spread out as I tried to get up, I found my legs had turned to jelly.

"I think a nap is in order. Poor Sarah can't find it in her to walk. It's okay we can resume in a bit. " Christina said as she sidled up to his left side, signalling me to lay on his right side as we cuddled up to him.

I must have passed out as I don't remember what happened next.

It must have been a few hours of us all napping together because the next thing I do remember is Christina waking me up.

"Sarah. Wake up. It's my turn now. Want to help wake Kevin up?" She asked me in a hushed tone as she tapped me awake.

I nodded. "Okay, now follow my lead!" She said as she took my hand and made me get up on the bed. Kevin was still asleep, nude and sleeping on his back. His behemoth dick was semi erect.

"I used to do this to him from time to time to wake him up. He's going to love this. Just follow my lead" she said as she started to suck his cock, licking just the tip before taking more into her mouth.

Before I could process the weirdness of my current wife sucking off her ex boyfriend in front of me, she stopped and handed me his cock, snapping me back to reality where that same cock just fucked my brains out. I started to suck it as well, trying to get Kevin to wake up.

From then on it turned into a competition to see who could get him to wake up as we took turns sucking and licking his gorgeous shaft.

Kevin finally stirred awake.

"Oh my. Don't stop ladies." He said with a smile as Christina and me intensified our efforts to suck him off together, licking each side of the shaft and sharing the head in a sloppy kiss, intermingling our tongues and his head while stroking him till he couldn't take it anymore.

"Fuck. That's enough ladies. Now whose turn is it?" Kevin said looking at us. Before I could respond Christina piped up. "Me me me. Please. Can I have a turn?" She said as she immediately got on all fours exposing her wet pussy to him.

"If that's okay with you?" Kevin asked looking in my direction. I nodded.

Maybe in another world or in other circumstances I would have not allowed it, maybe I would have felt jealous even. But tonight the only jealousy I was feeling was of Christina and not Kevin. Jealous of her that she gets to experience the best (and so far only) dick I've ever had.

He made his way to her and entered her feminine folds. Now, the tables had turned. It was my turn to watch him fuck her. I could only look at her face in envy, she started moaning and then screaming in pleasure. I had never seen her like this before. She was turning into a cock drunk submissive slut right before my eyes.

12