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Chapter 13
by OathkeeperPath
who is it?
Alex
"Ready for our date?" It was Alex, he loops his arm through mine and I let him lead me.
"Thanks, I'm not sure I was ready for these heels." I try to play it off, but the smirk on his face confirms my suspicion, he was the one logging into the plug app. My original resolve to see this through, to put if there could be an 'us' to rest, had long sense been replaced by an overwhelming need to cum. I had never been so horny in my life, so I decided to tease Alex back a little bit. Leaning into his ear I whispered in his ear the same way I liked from my ex girlfriends, "Or it could be this absolutely massive plug stuff in me, you wouldn't happen to know any thing about it would you?"
Its a good thing I'm clinging so close to him, as I get even less sure on my feet as he activates the vibrators in the cock ring and butt-plug. I feel a flush rise up on my face as he whispers. "I wouldn't know anything about that, Our dinner waits for us princess, I wonder if you can keep yourself from making a scene. " I go to retort, face flushed but I'd gathered myself enough to reply, at least until the vibrations changed rhythm. "Don't worry it'll be fun. You should enjoy yourself! " He smirks and continues to lead.
My cock is straining in it's bonds, I don't remember if it's ever been this horny before but the way she had me bound I'm half soft, pre-cum being pumped back into me, 'my hole is being lubricated by my own pre-cum'.
I can hear my breath coming out as gasps as I look to the sidewalk as I struggle to keep my thoughts straight.
I just let Alex lead me, he seems to content to let the conversation go idle as he watches me struggle, leaning into him.
He calms down with the pleasure **** when we make it to his car. "How are you feeling, want to pull the emergency cord?"
With breath ragged, trying to gain control of myself again at the brief respite, "GOD, No, just...just give me a minute."
"That's my girl," What he says next I don't know, as his cars natural vibration sends a shock through me as it stimulates the plug greater than what Alex had been doing, the only reason I didn't cum right then was the position my cock was in and the ring wasn't stimulating me.
I was leaking so much I could actually feel it in my hole this time.
The vibrations drove me crazy the whole way there, I was able to process something other than riding the edge. I have hold of the car with a **** grip when I hear my door pop open.
Alex keeps me close to his body and his hand goes to my hip as we enter and get seated at a nice table for two. This is really a much better place than I expected, he really went all out. 'He really wants us to have the best chance. How much did this cost him so far, let alone what this place will do to his bank accounts? I need to order something small and cheap, what is small and cheap at a place that has 40$ salads?!'
Alex reaches across and grabs the one from me, noticing I can't concentrate on what to pick. I can see in his eyes he thinks its from the after effects of the plug. I don't dissuade him that notion, I don't want to hurt his pride, at least not off the track. 'I'll ask later. I promised I'd follow his lead anyway.'
He puts in an order for wine, salad, soup, and steak before turning back to me as the waiter walks away.
My mind has left my worry about money and I'm back in my head about everything that I've been through these last few hours.
For the first time since leaving, my mind has caught up.
I'm in public, passing as a beautiful women, sex toys in and on me, and on a date with my male best friend.
I can't seem to find it in my self to be as terrified or embarrassed as I should be, Its oddly feeling me with joy?
"Hey I know that look, whats going on in that head of yours?"
"I..I should hate everything about this, but I don't?"
Alex's eyes are on me, as the plug in my ass makes me want to squirm.
I take a few breaths as I look across to him.
"That was the thing about you that always confused me about you. Your not dumb but this confuses you. How can you not know what you want even after all this? With how you act all the time."
"I..ITs... I don't. Shut up." I finish with a scowl and cross my arms in consternation.
"Like that right there, I'm sure you think your really giving me the stink eye, but that pout is really cute on your made up face and really crossing your arms with a rack like that just gives me ideas for later."
"WHAT?! How dare you, that was top tier bastard face, never seen a man glare at you?!" Hiss instead of yell not wanting to out us.
"Really?" he says in that infuriating way of his as he cocks an eyebrow. "You still think of yourself that way, even while dressed like this?"
"Yes, I'm still a man, I'm just, Its OK because its like a..." I trail off realizing I don't have an answer, I had convinced my self this was OK, by why? I whisper "Who am I if I can't even call myself a man?" as my face goes pale.
"Christ babe its not th-" He stops as I flinch at being called babe. "Man, its not that bad, you're having fun, no one is getting hurt. Whats the big deal?"
"Whats THE big deal?! I can't look like this, I'm not allowed to!" I near shout as I get a wild look in my and go to stand up and run.
I stop the movement when Alex puts his hand on mine. "Allowed? It's ok breath, talk to me, what do you mean. Wait is this about how you old man used to go on about being 'Manly'?, I mean I doubt our families will be thrilled but they'll learn to chill, If we tell them, If this date goes well."
"Yes its about that! Its like Suzy all over again, you're trying to trick me, with lies of getting to be beautiful and it'll ruin my life, like she near did."
"What? wow I know your dad was a piece of work but he really did a number on you. Wait is that why that Suzy girl ran away from you crying at the after prom party our senior year?"
"Yeah, she recognized me after all those years, she's from the next town over, was invited by friends or family, I don't know. But she was all excited to see me again, talking about how we used to play, wanted to see if I was up for it again 'now we could drive ourselves.' can you believe her?" I finish with a look of consternation.
"Holy shit dude, wtf, long lost friend finds you and you flip on her?"
"Friend? We haven't been friends in years, my dad moved us a town over to keep me way from her. She wanted me ruin my life!"
"By being beautiful? Something I'd like to point out you were before hand and seem to be enjoying immensely now with it enhanced, without any negative effects."
"Yeah..." The answer feels lame even to me.
"Your dad is a piece of shit and that explains a lot. Its OK, you're allowed to run your own life, you can be cute, you can be pretty, you can even be beautiful."
"I-" my weak protest is cute off as every nerve in my body has whip lash as he activates the plug and ring.
"I'm sure there is a correct way to fix what your father has clearly broken, but I'm not schooled in it, so I'm going to do what I do with all the problems I encounter with something important to me, I'll fix it my self with the tools I have. Now you are going to sit there, and have this date with me and any time I see your mind going down the wrong path, I'll 'shock' you back to reality, back to me. Got It. Princess?"
"Gahaahhh yeesss" Like that my mind is blank of all my problems and back to the pleasure of the night.
Alex's concerned look turns to a wicked one, smile on his lips.
His fingers tap a rhythm on the table that, the same one as my butt plug. "Your ass must be so full tonight, and your cock too, you look so sexy right now, a vacant look while riding the edge of pleasure, eyes squinting and mouth is slightly opening, like your about to moan or cum but you stop your self out of anxiety of getting caught. "
My cheeks get hot as I can only imagine the smile on my face right now.
My mind starts to focus on how pretty I feel. He keeps the conversation going as he starts to tease me and holding my hand, as we talk about other things, or more accurately he talks about other things, I try to, but keep trailing off, distracted with how I'm being played with while dressed like a bombshell.
Our food comes and goes, with Alex letting up the pressure when he thinks my mind is out of the wrong path and going full throttle when he sees it wonder the wrong way again.
It was after dessert that I felt it start to get a bit more intense. The plug starts to slowly expand and thrust in my ass, and the cock ring starts to alternate shocking and vibrating. "Gaaaaaah nuuuh I though we uuug uh were at the limit." I barely make out through my moans.
"Not quite darling, we got plenty we can do to you, but I want to see if you would let yourself get milked into yourself while you wait for him to bring the check."
I feel my cheeks start to burn red, I squirm in my seat, I can't control the whine I let out, "aahaha plleasse, iii wanna cum buuut not." I can't even finish the sentence as I have to clamp down on all my muscles to try not to cum.
I must look a mess as I white knuckle the silverware as Alex pays the bill.
When the waiter has left Alex leans across the table and puts his hands over mine. I'm barely holding it together, as his fingers stroke the top of my hands, he leans closer to whisper "You're such a slut for being out in public with that vibrating plug up your ass and vibrating ring on your cock, and that's OK, you can be my beautiful slut and it will be OK. Now, Look in to my eyes and hold my hands for stability as I make you cum. Let go of your resistance, cum for me."
As if on command my body's muscles relax for a second and then tense up in a completely different way up and I let out a mewing whimper of a moan "mmuuuuhhh" and feel my cock pump cum shot after cum shot, through the tube stuffed in it, all the way back to my plug and I feel myself cum in my own ass.
I'm sure a vacant look remained in my face for several minutes afterward before I was able to participate in conversation again.
"That was, that was a lot." *gasp* it feels like I stopped breathing for a second, and I may have, my mind felt like everything was pleasure for a sec.
"There she is my pretty girl all nice and glowing, lets get you back to my place to cuddle and let you enjoy the afterglow."
We slowly make our way to his car, I'm even more unsteady than before, he helps me ground myself and I'm surprised that as I lean into him my normal post nut regret is nowhere to be found.
Right as I start to get comfortable in our nice conversation and the afterglow I realize that I will be teased by his car again just on the ride home, I can't find it in myself to care, with my own cum sloshing in my plugged ass I step into the car.
The toys start teasing me again as soon as the car is turned on, and despite just cumming and being in the afterglow, I start to feel turned on again.
Alex notices and starts slipping in double entendres and teasing jokes in our conversation.
"Your such a good date tonight, you look so good and your so happy." He smiles and rubs my leg. My mind is starting to focus on how much I'm enjoying myself, I can't find that anger or fear inside me that was dominating my mind earlier.
"Honestly really enjoying it, not having my mind over thinking everything. I'm starting to feel like I can just go with the flow when I'm with you."
He's leading me up the steps to his apartment each step doing amazing things to my plug. He has a look on his face like he mulling something over in his head.
As we step into his place he finally responds, "So we're in agreement that for 'us' to work. Then we are going to use the rest of the night to wash any bad self hating thoughts away."
All I'm able to do is nod my head 'yes' as the toys activate again, taking my breath away. He takes my hand, closes the door and presses me against it, kissing my neck and rubbing my fake tits, causing the suctions cups tease my nipples.
Leaving me with a vacant look for a second time as my body responds to his manipulations better than anything I or any girlfriend has ever been able to do.
My ass and cock were already so sensitive from the first orgasm and the aphrodisiac still in me, that with out my will fighting it every step, I start to cum again as the toys make my ass tighten up and the ring causes my cock to pump in a my ass again.
All I can think is a comment I saw under my first porno while wearing panties, 'pretty sluts milk cock' I *giggle* guess that's true even if its only mine.
My mind starts to come down again, from the orgasmic high.
He pulls away and offers his hand expecting me to take it and follow him, but I'm unsure of how stable I'll be after so much pleasure so I cling to him as he leads me to his bed room.
My mind idly notes 'he's a better man than me he's already got me off multiple times and I've not done anything for him, I feel like such a selfish lover' the thought runs through my head before my mind turns back to how sexy he looks when he's taking control of me.
As we reach the door he pushes the remote again and it feels like the plug in my ass has expanded.
It feels like its right at the edge of too big, like my ass might rip, I hope I'm just sensitive right now from my recent orgasms as I can't really vocalize anything with the state I'm in, as despite cumming he hasn't turned anything down.
His mouth going to my ear to whisper, "your mine and no one else can touch you or get you off but me." He whispers the words like a spell and I moan my agreement and I know in that moment, in this state that it's the truth, I'm his and I'll stay that way.
"I'm yours." I whisper back, kissing him before he pushes me back onto the bed.
"Good, but just to be sure I'm going to keep pushing you over the edge, we will wash any lingering fears or doubts away as you cum and cum, like my Beautiful Princess should."
—------------—
End of current arc for this story. The characters will return if voted for when we do story polls. Current main story is Voodoo Doll ****.
Chapters are posted early on my Patreon, currently two chapters ahead over there, Link in Bio. It also has the most recent updates for the game I'm working on.
Newly added is Feminization support it you want to become a Femboy, Sissy, or any other flavor of fem.
I also stream under the name Gemini_Kiss and make NSFW captions on reddit (username gothdreams) and the patreon discord .
How does he follow through on that promise?
- No further chapters
- Add a new chapter
Street Racing Princess
Are you man enough to dress like a chick?
Alex and you have been friends and rivals for years on the street racing scene in your home town, this continued from high school to post community College. You've both always had fun making bets on the races, but here lately Alex has been winning, alot, and the bets have taken a turn.
- Tags
- sissy, bra, bras, stocking, stockings, Race, Panties, Romance, Feminization, Racing, Bet, Femboy, Gurl, crossdress, crossdresser
Updated on Jan 19, 2024
by OathkeeperPath
Created on Nov 29, 2023
by OathkeeperPath
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