Chapter 10
by 
OathkeeperPath
Which option?
Girlfriend
In that moment, everything seemed to slow as I came to my decision, it's the only one that makes sense. "You sure know how to propose to a gu- I mean girl," I remarked with a touch of humor, breaking the tension.
I saw her relax slightly, allowing her own nervousness to show. "Sarah," I began, speaking with confidence I'd not felt in days. "I choose option three, I'm not even going to pretend that I didn't have the hots for you, from day one, and I would be a hypocrite if I said your 'surprise' changed how I felt. Especially if I still want you, or anyone else, to find me attractive after all this, I'm starting in only two days and I doubt anyone could tell I'm a man anymore."
That earned a chuckle from Sarah, and a warm hug. After a moment, we separated, though her hand remained resting on my cheek. Her touch was soft and gentle, comforting. Whispering in my ear "If you're absolutely certain, I'll be happy to make you mine" she finished with a husky voice as she led me into a long passionate kiss.
I was leaning into the counter by this point for stability between my heels and her passion I was losing my sense of balance, she finally sensed that I was about to fall over.
She put her arm under mine and leading me to her room, switching between giggling and kissing me on the cheek along the way.
When we got into her room her lips seemed to attach themselves to my neck, stopping only to take off my top, teasing a small gasp out of me, feeling my cock straining against its confines and still hidden behind my long floral skirt.
My skin was sensitive even to the air now, weather it was from one of the products used or missing hair I don't know nor did I care, my nipples were like diamonds trying to cut through the bra.
I heard her murmuring into my ear about how gorgeous I looked and what a good job I had done, that voice of hers ending it with seductive talk and kisses trailing my stomach was overkill.
Sarah turned me so my back was pressed to her, "This will have to go," she teased as her hands gently coming around to squeeze my breasts before her fingers went back and unhooked the bra they were bound to. The sensation of it dragged a groan from me, I never knew how freeing it was to simply take my bra off. 'My bra. Christ this is still weird.' "oooohhhaaa" she got a really good moan out me, giving me a hickey while playing softly with my nipple from behind, body pressed to me. 'Fuck it, being with her defiantly feels like its worth the cost of admission right now.'
"You like that sweetie? Imagine how they'll feel when we get you some real ones to play with."
I go to turn over so we can resume making out and to be less passive, and ask what that means specifically, "Wh-" but she stays my body by running her nails along my spine.
"Easy, Honey. We'll get there," Sarah consoled.
After a few playful rakes and an ass slap, she turned me to face her, tenderly kissing my lips, while slowly lifting my hands until they were on her shoulders. Pulling back, she gave me a wink before her hands slipped down to my waist. Her hands were deft as they went to work taking my skirt off.
I could feel my breathing becoming heavier as it slipped from my hips, then stepping out of them at her direction, exposing me to Sarah's gaze and touch. "There's my girl. Such a pretty sight," she remarked. "You're so close to perfect already pet."
I could only blush from her words and the way her eyes explored me, as if they weren't missing a detail. Seeing the desire in her eyes and knowing I was putting it there filled me with a sense of power I'd never felt before, but the knowledge of what I agreed to claimed that feeling.
She was intoxicating and I was hooked.
Her hands came to a rest at the top of my panties, running the length of my waist under the elastic, and began to slowly lower them this was until I was completely bare. She kept her eyes on mine as the silky fabric was worked off me.
I could tell, with our eyes looked, she loved the effect her actions were having on me.
The last of my coverings discarded, I was exposed, now standing in a sensually **** pose in the spot-light of Sarah's bedroom. There was something uniquely pleasurable about being nude and my partner fully clothed, being made to focus on the hungry gaze of another instead of their body.
She carefully grabbed my hand and led me to her bed to lay me down again and then climbed atop to hover above me.
Gently lowering herself on top of me, the feeling of being pinned spread goosebumps across my body.
Sarah's free hand, the other pinning my wrists currently, drifted down between us and through my now shaved pubes and the small amount of pre-cum there, before gliding to her cage and the insane amount it was leaking, "Careful," Sarah teased, "You aren't supposed to get me wet like this, unless you can follow though." I heard her chuckle in my ear while her hand moved again to my cock, her teasing touches drawing more juices out and my cock to throbbing hardness, as I blush and try to wiggle away. "And what is going on here, oh naughty girl!"
I was looking away biting my lip. "Sarahyyyy" I whined half embarrassed and trying to wiggle free, completely forgetting I was the stronger one out of us if I would put real **** into it. "Don't tease meeee, pleaseee." I could almost hear her smirk as she licked my ear drawing a moan.
"I haven't even started to tease you, I need you wet, I would be a bad partner if I ended foreplay before your soaking." she replied as she nuzzled my neck. Her fingers strummed over the edge of her chastity, feeling the sticky fluid oozing out before cupping my bulge with her hand covered in her juice and giving it a gentle squeeze. "I need you like this, like how seeing you all femmed up and submissive has gotten me." she commented, with affection and kisses.
Before I could respond, she was claiming my mouth again. Sarah was enjoying having control, at least until I bit her lip in a small act of rebellion. She must've liked the challenge, because moments later, I found myself the recipient of some very warm, passionate tongue as she adjusted her weight to have more body control.
I moaned into her mouth as her hand found my left nipple again and stroked the sensitive nub. As my passion began to rise, I felt her rhythm falter.
Our lips pulled apart and I began to feel cold, worried. Suddenly, Sarah was no longer holding me down. She was kneeling at the side of the bed. Why wasn't she touching me? "Sarah?" I asked hesitantly.
My vision fully focused. I saw her kneeling beside the bed, chest heaving. I could see her face was strained. "Sarah, are you okay?" I asked, rising from my position on the bed to reach her.
She halted me with a wave. "Can... Can you be patient a minute? I know what I promised..." she heaved, "but I need a moment." I watched, concerned, as she straightened and stood, walking a few steps away from the bed, I could almost hear her speak to herself, "...its ok...wants...needs...won't... show her, she'll.... Game face girl..." before spinning to face me.
"Sarah, talk to me. What's the matter?" I begged, a little hurt and confused. Was I doing something wrong?
As I met her eyes, I could see a spark re-ignite within them.
"Sorry I was, uh, somewhere else for a second."
"Are you ok? Are we ok?" I ask nervous.
Instead of an answer, she asked, "Are you afraid, Sadie?" eyes intense.
I pulled back a little, feeling self-conscious. "N-no," I stammered, "Why?"
The fire in her eyes flared as she stepped toward the bed. "Do you still want me to make you mine?" she asked, a growing confidence apparent in her voice.
That was it... she was back.
I shivered, I was putting myself in a relationship with someone far kinkier than me, clearly with unresolved issues, and willingly put themselves through long chastity. With a moment with out her touch to center myself I was able to ask myself honestly.
'Do I want this still, with everything I know and the things I clearly don't?' I remembered a conversation I had with another streamer doing an AMA, It was what made me pull the trigger to become one myself.
He said, 'Every path you walk will have problems the only thing we can influence in life is which problems, do I want the stress of streaming if it means I can live my dream?'
I had already decided that I did for that, come what may. 'Is dating my dream girl that much different than my dream job?'
I felt a shudder pass through me. 'If she would do that to herself what would she do to me for her pleasure or my streaming success?'
'Would it matter, would I care overly much? She has done so much for me already, would letting her have her fun with me really be a deal breaker, am I so selfish that I'd be willing to sacrifice my dream girlfriend and possibly my dream job, just because I wouldn't let her lead?'
A conclusion was forming in my head, the same one from earlier, but that was when this was all abstract, living in that moment with all it entailed was harder to square the circle on, but it still lead to the same conclusion.
"Answer me, Sadie, please" she prompted, pulling me from my thoughts, her foot striking the bed between my knees. Not in anger but to punctuate the order and hide her vulnerability.
The sound resonated deeply in my body regardless.
"I-i want it," I said. Giving her the only answer that made any sense.
Her hand clasped around my ankle, tugging me closer. Her other hand gripped around my cock, giving it a long, firm stroke. The sensation made my vision cloudy. "Then give yourself to me, Sadie," she commanded, her lips against my calf.
There it was again, that feeling of connection, of empowerment and relinquishing power. If this is what she was craving I would give it to her. "Yes, mistress," I replied obediently, a tingle running down my spine. Her answering smile was priceless.
"If you do really good pet, I'll teach you how to really make money. But for now your all mine to toy with." I felt a shiver run down my spine and a question on my lips before her kissing my leg washed it away, it felt like I was on fire where she had touched.
"ooohh"
With each moan I let out she would respond,"Good girl," before kissing and licking me higher and higher to make me gasp and moan again, "Pet, you are mine. Let my words write it on your body, mind, and soul. I won't ever give you up now, If you disobey, you will be punished. Be a good girl and be rewarded."
My mind was only on one thing, her getting closer to my cock with her mouth, I said "Yes!" over and over until she was in between my legs, over my cock, licking a line right down the center and swirling her tongue around my head her skills or teasing tongue getting a yelp out of me. "Thank me pet, this treat is a reward for submitting and becoming mine, it won't happen often." She demanded and I answered.
"Thank you, Mis-ughohhgod", as she suddenly took me in to the hilt, her nose buried. Before coming back to my tip.
I thought she would want me to get her off, but now I don't know what she wants but God can she suck cock.
I won't complain but my fingers now are at home in her hair pressing her forward silently begging for more of her heaven like mouth.
Her technique is driving me wild. I would swear it felt better than anyone else ever touching my cock.
But her head wouldn't move and I didn't want to go from silent begging to forceful demand.
"Now Sadie since this is our first time, there are a few things you need to know before I get to try drive you crazy with lust. No cumming until I say so, if you do I'll just make you eat it, then work back to the edge to try again." and with that I was seeing stars and throwing my head back, arching my body.
Next time I looked her way I could only stare, in her free hand was a remote vibrator.
Was that for me or her?
I don't know how long I could last without cumming as is, with a toy added?
'wouldn't she just let me fuck her so we can both cum?'
My hips bucked trying to hold on while I whimpered for release, the sensations were too much to bare, Her head bobbing and sucking and licking,"ooohhauplea, oh goooooood." My words reminded me of porn, of the actress getting ate out.
I wish I could say that the sounds coming out of me were on purpose, to feed fantasy, but they weren't.
It only made Sarah smirk and chuckle, mouth on my dick still, she managed to use her arms to lift my legs and ass, before setting me back down.
She had snuck the vibrator below my ass, never stopping giving me mind blowing, only slowing down to stop me from cumming.
The toy was soon slowly driving me out of my mind, Sarah was backing off every time I got close and I was fighting every bit I could not too, I truly believed she would follow through on her promise to make me eat it, I didn't want to but I knew I would let her in this state.
"You're doing so good darling, but no cumming yet, we wouldn't want you to ruin the fun right?" I whimpered and she kept edging me for what felt like hours or years.
Until she pulled herself off my cock and giggled.
Looking down I saw, her right hand buried under her skirt and pulling another vibrator out of her. "Now its time for the real fun, I'm going to bounce on you like a sex toy and you have to not cum before I have a sissygasm, now if you do, you have to eat all my cum and only your own if you don't even get close."
I was almost crying with tears by this point as she set her self on my lap, impaling herself on me, and began riding me at an angle that made me lose myself faster.
She started teasing me about being a her new favorite fuck toy, it surprised me how good it felt to be dominated this much.
Trying to coach me to hold my self back longer, she told me "Breath pet, relax, enjoy, uughh, but not too much, If you're good and I get off first, oohh, you can cum in my ass and I'll lick my cum off you, hhuuuggh, but if not well, your lucky I keep my self as clean as I do, you'll be eating your load out of me as I collect mine to feed to yoooou." Her moans cutting in as she was starting to really enjoy her self.
I almost sobbed as I fought to not cum as I experienced the most pleasure I ever had.
She was getting close, I could tell from how her ass would clench around me. She was so close.
"NOOO oh goooood, I'm-" She cut my cry off with a kiss as I came in her.
She continued to ride me, making my body shiver in post nut sensitivity, a second I felt her whole body tighten and release with a moan right by my ears and a wet spot forming between us.
That's when the toy under me stopped and my cock felt cold air on it.
She leaned down and started to lick up her cum.
I breathed a sigh of relied, it must have been close enough for her if she was eating it.
I closed my eyes to bask in the after glow, before long she came up for a kiss, I didn't mind a post 'blowjob' kiss and I returned the kiss, only for her to **** her tongue in my mouth and the hold me as I tried to remove my head in realization. "MMMMMHH" She held me there and made me swallow her load while kissing me, I tried to yell no into her but she held and I knew **** my way out but it would break something between us and that scared me more than the taste revolted me.
Pulling herself away from me she whispered, "Shhhussh, Such a good sissy, such a good pet, trying so hard, but you failed your task. Now lie still."
My mouth agape in shock, I didn't move. 'What did I get myself into.'
I felt her cleaning me with a towel and was thankful for that, she probably knew how messed up my mind was and wanted to let me gather my self while she cleaned us both up.
"Thanks babe. I-"
"We are still in the bedroom pet, what do you call me?"
"Thank you Mistress." I respond as I move rise my torso with my elbows
"Better, and nope, back down pet, I'm not done."
I do as she says and rest for a moment when I feel something cold against my cock, she's grabbed my balls too. 'If shes ready for more I can certainly try.'
*Click* "You can look up pet, do you like the color?" To my horror I'm now in a chastity cage. A bright anodized pink one.
"I...uhh, Sar-Misstress, why?"
"Oh honey, me wanting it should be enough," She started climbing into the bed with me as she explained it as a 'matter of fact', "but if you need more, its to help you with your streaming and acting the right kind of fem, You'll be horny, shy, submissive, and embarrassed. The audience will eat it up."
I laid there in shock and let her lead me into cuddling, I had never been the small spoon before, It felt nice.
I was able to ignore processing anything, until it happened, there was a mirror on her dresser and I saw me, a cute girl all sexed up, there was even bit of her cum that was on my chin, and to my great shame my tongue darted out to lick it up before I could think about what it was doing.
It all came crashing down on me, everything I had lost, everything I had further sacrificed for a chance at getting my dream back, and what I just surrendered for a girlfriend.
It felt like I had gained the world only to lose not just my soul, but my body and mind too.
I turned from the mirror and buried my head into her, I held onto her for dear life as I cried.
To her credit she held me, soothingly stroked my hair, while whispering love into my ears, punctuating each affirmation with a kiss on my head.
I cried my self empty in her arms.