Finding Stephanie Ch. 02

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

We got home realizing how late it was, we ordered Chinese food for pickup since I didn't feel like cooking given how long of a day it had been. I went and picked up the food, the guy working the counter gave me a big smile. When I got home, Paula and Sarah were with Kaitlyn. I was a bit shocked. Kaitlyn got up and handed me a glass of wine, I practically chugged it.

"If you were going to hammer it back like that, you could have had a shot." She laughed a bit before refilling my glass.

"Actually given where this conversation is going, I would love a shot." I replied.

Kaitlyn grabbed the bottle of orange flavoured vodka that we had constantly in the freezer and poured a small glass, "here you go babe."

I slammed it back, "Okay, I guess I'm ready for this."

Kaitlyn started out, "As I was telling you guys before, Stephen has gone through some changes after she confided some things to me, also while we are on that topic she would prefer to be called Steph or Stephanie now and use female pronouns..." she paused for a moment "so she and her, anything to add sweetie?" she looked over to me.

I shook my head back and forth, "no... that about sums it up."

Sarah spoke up first, "So are you transgender? Or..."

"That's something I'm going to have to discuss with a therapist when the government coverage for health benefits comes through because I applied for insurance assistance which also has simple health coverage attached to it... but I think so... it's something I've been dealing with since I was a kid but have had some really bad experiences that kept me from sharing it with anyone," I replied.

Sarah frowned and had a bit of anger on her face, "Kaitlyn told us about how your ex reacted, I'm sorry she was such a bitch and talked to you that way... Paul, you've been awfully quite, do you have anything to say to Stephanie."

"Will we still drink beers and watch games?" he asked me in a way that reminded of a kid asking his divorcing parents a question.

"Yeah, Paul we will," I giggled "I have to cut back a bit cause I'm only getting $1300 a month from the government and I'm going to start taking some IT certifications."

"That makes sense... Just in advance sorry if I screw up on your name at first but I'm going to my best Steph." He smiled at me.

Sarah spoke back up, "Really Paul? That's your only question?"

"I mean... yeah? That's really the only time we hang out and I like those hang outs." He replied in a confused voice.

"Well I do have a question, how did this come about?" Sarah spoke again.

"I think the stress of losing my job and seeing how bad the job market is, I fell back into a comfortable thing that I couldn't hide anymore and then Kaitlyn found out. She's been so supportive and amazing to me these last couple of days. Not that she hasn't always been with me... but she did a lot from cutting and dying my hair, doing my eyelashes and eyebrows, and doing my makeup today." I told the group.

Sarah smiled, "Well Kaitlyn sure is happy. You're pretty much her perfect partner with her being bi." she laughed.

Kaitlyn gave her a bit of a glare "I like Stephanie for who she is! Not for looking or identifying any specific way, does she have an amazing ass, yes but that's just a bonus."

That caused the entire group including myself to laugh even though I blushed a little.

Sarah replied still laughing, "Well you ain't wrong about that ass, you could bounce a quarter off of it!"

Paul spoke up, "I mean as the only guy here, it's going to get you a lot of attention Stephan...ie. Fuck me, I'm sorry. It's going to take me a bit." Paul frowned upset at his screw up.

"It's okay Paul. As long as you are trying!" I reassured him.

We all had some more drinks, watched a movie and ate the Chinese food. Sarah and Paul eventually went back up to the upstairs. Kaitlyn and I headed to our bedroom.

"Do you want to see me in the new lingerie?" I asked.

"You know I would love nothing more in the world but it's late and I have to work tomorrow." She replied through a yawn.

I frowned a little but she was completely right, it was very late and my alarm would be going off in 5 hours which meant she would have to be up in 6. We both passed out hard.

I awoke to my alarm going off and for the first time in awhile, I cursed at it for going off. I yawned, getting dressed in my new gym thong and pants then an older gym shirt. I made a quick breakfast of bacon and eggs. I went to sit down on the couch and I passed out. I awoke to Kaitlyn kissing me on the cheek to wake me up.

"I'm sorry breakfast is probably a little cold." I said waking back up.

"It's okay babe. I warmed it back up in the microwave. I guess Tim Hortons coffee it is today!" she replied.

"Yeah, I'm sorry I totally forgot about making coffee... I sat down on the couch to take a rest... and I just fell back asleep."

"It's perfectly fine. Don't worry about it babe. You don't have to nail everything, every day." she reassured me.

We ate breakfast in relative silence, us both nursing hang overs and lack of sleep. I dropped her off for work, went to the gym and was having one of the most uninspired workouts ever. I went home, laid down in bed and went back to sleep. I awoke a few hours later and realized I still had a decent amount of time before having to pick Kaitlyn up from work. So I made a dinner of slow roasted chicken, potatoes and vegetables. I timed it all to be done when I would have her home.

When she walked in our door, she immediately said "Holy fuck, that smells amazing!!!"

She got changed into her home clothes and then we ate dinner. The dinner seemed to bring us both back to life as our energy levels returned.

As we finished she spoke up, "Well do you want to go get your new lingerie on?!" she giggled a little.

"Yes, yes I do!" I replied, walking into our bedroom, getting changed into the light blue and white French lingerie, I walked back in the living room and her jaw just about hit the floor.

"Holy shit, do I ever have a hot fucking girlfriend!! Who can also cook restaurant level meals, takes care of me, makes sure all the chores are done, I better be careful so some hot Chad doesn't come and steal you away from me!" she giggled.

"I don't know if a Chad would like this as much as you do" I said pointing down to my hard cock pressing against the front of the thong.

"I don't think he would care given the rest of you babe!" She smiled with a bit of a grin "Go get your makeup and the rest of my things, I'm going to do you up and then we are going to take some pictures of you."

I followed her instructions she quickly did my makeup, then grabbed her DSLR camera, instructing me on how to pose, she must have taken 50 pictures. "I will go through these, pick out the best ones and edit them a little just to make them look even better!" She told me "you should grab your iPhone and take a new selfie for all of your online profiles. Maybe other than Facebook unless you want to come out to your family."

"Definitely not yet... I need to speak to a therapist about everything first... the agent who checked all my info for the income support said it would be a week or two until I got the card for health coverage." I replied then grabbed my phone and snapped a few pictures until I was happy with one that would be appropriate for a profile picture. "I can't wait for cell phone cameras to get even better! I think soon they will be better than most low end digital cameras."

"It's crazy how far they've come since the release of the first iPhone, now to yours, in such a short amount of time." She added. "Babe, you know what you should do?"

"What's that?" I asked.

"You should go get the lube and your new butt plug! I think it would complete the look and be so hot!" she smiled widely.

"You're right as always!" I ran off to the bedroom finding the lube and butt plug from my nightstand, coming back to the living room finding her now in just her panties, sitting down on the couch beside her handing them both to her.

"Get on all fours, over the arm of the couch." She ordered.

I did as she said, she pulled my thong from between my checks, placing the strand of material on top my cheek, I heard her squirt out some lube then I felt her apply the cool liquid to my butt hole, sliding in one finger, when she noticed how easily it went in, she gave me a smack on the ass. "You've been a bad girl even before you met me!" she giggled and spanked me 4 more times, as she added in another finger at the same time. I moaned louder with each spank. "You're going to have to be careful not to moan so loudly like a slut or Paul might hear you and want to come down here and fuck you." She laughed again, as she landed 5 more spanks. She pulled her fingers out and replaced them with the butt plug, putting my thong back between my cheeks covering the plug.

"Okay! That's it for now." She said. As I sat down she pulled out a remote that I hadn't seen before, she pressed a button on it and the plug began to vibrate gently. I didn't know it was a vibrating plug when she bought it but she clearly knew what she was doing. She put some porn on the TV, it was a video of guys with monster cocks. I reached down to rub my cock and she swatted my hand away. "No touching yourself! If you want to cum, you will have to learn how to do it from just anal stimulation! If you can't keep your hands off of it, I might just have to lock it away."

I had no idea what she meant by lock it away but I didn't want to find out, so I sat on my hands. She rubbed her pussy from outside her panties as we watched the video, she increased the intensity of the vibrations from the plug in me. I was barely paying attention to the video but every time I opened up my eyes, I would see a huge cock usually with text over it, like you know you want it, you are a slut for cock and other words of encouragement that seemed to be directed towards me taking cock.

I lost track of time, I could feel cum leaking out of my cock and then I felt the intensity of the vibrations get even stronger. I opened my eyes to see Kaitlyn still rubbing herself, not even watching the screen, she was just watching me struggle and moan, I could tell from the look in her eyes she was enjoying it intensely. She smiled when our eyes locked.

"Eyes on the screen babe." She got up and walked to the bedroom, I watched her come back with something in her hands, she stepped behind me and put something small and leather around my neck. I reached up to feel it noticing that there were letters on top of the leather choker, I traced out the letters with my finger, S L U T, I looked up at her and she had a big grin on her face. "This doesn't come off except to shower. Got it?" I nodded. She took my head and gently faced it towards the TV screen. She held my head in place while videos of large cocks being serviced by small girls, trans girls and femboys played while words came up over them. I noticed the words were repeating. As this went on I noticed my moans were getting very loud but they were interrupted by the sound of the sliding door opening.

I watched Paul walk through, stroking his hard cock, that was showing clear as day poking up creating a tent in his sweat pants. I had never given Paul that good of a look previously just looking at his face and not taking the rest of him in. He was a pretty average looking guy, a well trimmed beard, short brown hair, just over 6 feet, average build with a bit of a beer gut starting to develop. I looked over to Kaitlyn, she smiled devilishly, held up the remote again pressing the button increasing the intensity of the plug inside me even more. That level broke me, my entire body began to shake, I began not just moaning but whimpering too.

Kaitlyn took my hand and led me to the bedroom, Paul walking behind me, his eyes I'm sure we're focused on my ass, she sat me down on the bed, I was still moaning and making whimpering noises.

"Well I guess we have some things to clue you in on Stephanie," Kaitlyn started, "You see before you and I got together, I used to give Paul blow jobs cause Sarah has a very low sex drive and Paul, well Paul would be happy to cum daily and he doesn't care for masturbating. She was aware of our arrangement and was fine with it. I haven't done that since you and I have been together. I never cheated on you because I love you and I didn't love Tim. To be honest, he was kinda just nice to have around but more in a friendly way."

I listened to her speak, I tried to soak in all the words but the vibrations were causing me to not be able to focus on her words, I was just happy to hear she didn't cheat on me, so I just nodded through the moans.

She turned to Paul, "She can suck your dick, any time, but only I get to fuck her, understand?" Then she turned to me, "I told you to keep your moaning down or Paul would hear you... or maybe you wanted him to hear you cause you're a slut like that. Either way it doesn't matter, your mouth is his now, okay?"

We both nodded without saying a word, his eyes were focused on me and the mess I was in front of him. He took off his sweats, his cock springing to life now being freed from it's cotton prison. It was slightly longer and thicker than mine but unlike mine it had no curve to it, it just stuck straight forward.

I was mesmerized by his cock, I couldn't take my eyes off of it. I felt Kaitlyn guide me on to all fours, my face facing the end of the bed, the rest of my body to the middle. She gave me temporary relief pulling out the plug. I missed how full it made me feel but I was happy not to be in constant state of pleasure from the vibrations. It didn't take her long to replace the plug with the dildo that she had now put into the harness that was tied around her legs and hips. I hadn't even seen her put it on but it could have happened while I was in lala land on the couch. She didn't have any trouble getting the full length of the dildo inside of me, I figured she must have been using the smaller of the two we bought.

She started to fuck me, slowly at first. As she got going, Paul walked up and put his cock right in front of my lips. I opened up and first took his head in my mouth, twirling my tongue around the top. All 3 of our moans began to fill the room. Paul pushed his hips forward shoving more of his cock into my mouth and starting down my throat. I gagged a bit and he pulled back.

"That is something you're going to have to practice babe. You should be able to deep throat his cock no problem." Kaitlyn told me through her moans as she picked up the pace fucking me from behind. I could feel her strong hips colliding with my ass, making very district smacking noises. It was sounds I was used to hearing when I was behind a girl but now I was the one being fucked increasingly hard.

Paul kept pushing in and taking out his cock out of my mouth, pushing a little bit more down into my throat with each thrust. I gasped for air every time I got a chance. I was starting to adjust to having a cock down my throat, I focused on breathing out of my nose and trying to relax. Paul eventually got most of his cock down my throat, I could feel his pubes touching my nose.

Kaitlyn squeeled with joy watching me almost able to take all of his cock. She started fucking me hard at what I assumed was her full speed. It was like Paul and her were timing their rhythms. When she was on a back stroke, he was thrusting forward. They kept up this for a long time but at the same time I had lost all sense of time and had no clue how long it had been going on for.

Paul let out a loud grunt, I could feel his cock tighten up and then he released a huge load into my throat. I tried to swallow it all but there was so much of it that a decent amount of it came out of lips and on to my chin and the sides of my mouth.

Seeing all of it from her position must have really tuned on Kaitlyn which caused her to thrust hard into me, her hips on my ass, and she had an orgasm, her entire body shaking. This created a chain reaction and I was finally able to cum. I could feel my entire body shake and my cock finally emptying it's load. I collapsed on the bed no longer able to hold myself up. Kristin also fell on top of me, I could feel her big boobs on my back.

Paul wiped his semi hard cock on my cheeks, slapped it against my face and then demanded I clean him up after I didn't get the message from smacking of my face with it. I did my best to clean his entire cock with my tongue, sucking back the rest of his load that coated his cock. Kaitlyn cooed in my ear, "Good girl." Paul left without saying another word. Kaitlyn laid on top of me for awhile before regaining enough energy to pull out of and off of me and laid down on her pillow.

She reached down to the harness pulling out the dildo, handing it to me with a bottle of toy cleaner, "Please go clean this up babe. You should also hand wash your panties, there is a bottle of gentle soap in the bathroom. They won't do well in the washer."

I went to the bathroom and cleaned the dildo and my panties. By the time I came back to the bedroom, Kaitlyn was already asleep. I got into bed beside her nuzzling my ass against her crotch. She let out a little happy noise and then wrapped her arm around me, pulling me in tight. I was asleep the second my head hit the pillow.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
ArtickArtick4 months ago

Mmmmm... Beautifully hot Stephanie. <3

Share this Story

Similar Stories

Becoming My Sister Pt. 01 A boy's obsession with his sister changes his life forever.in Transgender & Crossdressers
Eric or Erica? Pt. 01 Eric is saved from near death but his rescuers are different.in Transgender & Crossdressers
Pleasing Mr. Wilson A summer job at the cottage leads to unexpected duties.in Transgender & Crossdressers
Keeping a Secret After a discovery, should he keep their secret or not?in Transgender & Crossdressers
Adele finally becomes a Sissy Caught dressed as Adele.in Transgender & Crossdressers
More Stories