Crossed Wires Pt. 02

Story Info
Sandy brings me home and we enjoy my new outfit.
1.6k words
4.52
41.1k
26

Part 2 of the 2 part series

Updated 06/08/2023
Created 12/07/2016
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
bigrusker
bigrusker
133 Followers

This is party two of my Crossed Wires story. I recommend reading part 1 first.

*****

The drive home from the sim session was surprisingly quiet. Sandy kept glancing over at me in the passenger seat, forming a little grin when she caught me running my hands up and down my side and cupping the breasts of my bustier. Oh right, I was still wearing the lingerie under my clothes that she'd laid out for me after the sim session. Important details and all.

To be honest, it felt good. My mind was wandering all over my body but I just couldn't get it to leave the sensation of wearing a thong alone. The way it cupped my balls and rubbed against my hole was completely new to me, and had me in a constant state of arousal.

"So how did you plan all this?" I asked her.

"What? The sim session? Or the bit afterwards?"

"The sim session... I mean, I never would have signed myself up for that myself."

She giggled. "Sometimes you just know! I've been getting an odd vibe from you recently - you seemed to be staring at women a lot more than usual. At first I was jealous but then, I realized that I was really curious what it felt like to be a guy, and I thought you might be going through the same thing subconsciously."

"So just like that, you decided that I wanted to be a girl?" I asked incredulously.

"Well I can't say I was terribly certain. I figured that you'd either be okay to try it or that you'd freak out and we would have to drop out of the sim." She replied as she changed lanes on the highway. "But then when I overheard you giving the extra instruction to the clerk I knew that we were going to have a good time."

I laughed a little uneasily. I still couldn't believe that I had accidentally ordered the clerk to make me like dicks. "Yea that worked out pretty well for you..." I replied, staring out the window.

The conversation died and I watched the city scenery slide past outside. The sim shop was in the next city over and the drive back would be another ten minutes yet.

Sandy cleared her throat. "So uh, how do you feel?"

I looked down, feeling awkward to talk about my lingerie. "It's uh... Good... I think..." I said as my hand wandered down over my crotch.

Sandy gave a mysterious smile and we kept driving.

================================================================

We pulled into the garage and the door slid shut behind us as we got out of the car. I walked around the hood and met Sandy in front of the car where she pulled me into a tight hug. After a moment she stood up straight and started kissing me.

The kiss was the most passionate kiss we'd had in a long while. It started slow, with long moments as I felt her supple and full lips. Then each motion became shorter and faster, building up as we began to explore each other's mouths. I started to reach out to cup Sandy's breasts, but instead she beat me to it and started cupping mine. It felt a little strange for her to feel me like that, though I couldn't feel much through the cup of the bustier.

Just then Sandy spun me around and pushed my face down onto the hood of the car with her hands, while she used her right foot to pull my right foot apart from my left. In an instant I was bent over the car with my feet spread, and the sensation of the thong against my hole extremely apparent.

I felt her hand reach down below me and pop the button of my jeans and pull down the zipper. Having completed that she proceeded to pull down my jeans, taking off my shoes in the process. I was left standing there in my stockings presenting my butt to her. I was so overcome with arousal that I forgot to stand up or fight her.

Having completed her will she pulled me up and in the process removed my shirt. She looked me up and down. "Fuck this is hot" she stated matter-of-factly. The tent in my underwear confirmed that I agreed.

Grabbing me by the hand she led me inside and sat down on the couch, pushing me down and onto my knees in front of her. I was so turned on I simply went along with it. My mouth was watering, I had no desire to stop. She then lifted the front of her skirt and made a somewhat unladylike gesture. I knew what to do.

I crawled forward and turned up the footlong skirt she was wearing. I was greeted with the sight of a damp spot forming on the same thong that I was currently wearing. I blushed and looked up.

"Oh did I forget to tell you we're wearing matching underwear sweetie?" She asked with a sly grin.

I just nodded and proceeded to pull hers down her legs, revealing her very wet sex. I started forward with her head, then remembered what she had done in the sim. I stopped myself and instead started playing with her clit in the same circular motion she had used on me, while my left hand started to migrate down towards her sex.

I started to slowly push in and out with my left hand while continuing the circular motion with my right. In no time Sandy was convulsing with pleasure and squeezing me with her legs in orgasm.

I sat back on my knees and looked up at her expectantly. Usually at this point I would crawl on top of her and take her, but I was enjoying being a girl right now-

My eyes shot open as I realized what thought had just crossed my mind. I was enjoying being a girl...

"What are you staring at?" Sandy barked, catching my wide-eyed gaze.

"Oh uh, nothing Sandy.. I just.. I'm.." I tried to explain myself, but couldn't figure out what to say.

"You're enjoying yourself?"

"Yes!" I replied, nodding vigorously.

"Hmmm..." She said, and immediately stood up and starting walking down the hall toward our bedrooms. "Stay right there!"

I did as I was told and remained on the floor kneeling in front of the couch. I stared into space mulling my situation while idly exploring my lingerie-covered body.

A few minutes later Sandy emerged from our room and the sight left me breathless. She stood before me in black lace lingerie and my breath caught. It wasn't her heels, the black stockings, or black corset, it was the red strap-on hanging down between her legs that really got me.

I stared at it, it stared back at me.

My mouth watered.

Sandy walked up in front of me and motioned for me to turn around and bend over the couch.

Unfortunately for her, I was already on a sex-driven autopilot.

I reached out for the plastic member, wrapped my hand around it, and immediately started giving a blowjob. I didn't care that Sandy couldn't feel it. Every time I pushed it farther into my mouth I could feel my whole body quiver with excitement. It wasn't long before all 7 inches were wet and I felt pre-cum dripping from my panties.

I pulled back and sat back on my feet.

"How was it?" Sandy asked.

"Mmm... The real thing tastes better." I replied. Then I proceeded to turn around and present myself to her, bending myself over the couch in the process. I felt Sandy come up behind me and push the thong aside to reveal my virgin hole. Adjusting her position slightly, I felt her squeeze a drop of lube from an unseen bottle onto me. Then there was pressure.

I felt myself constricting in surprise. The feeling was very strange. I took a few deep breaths and forced myself to relax. Sandy slid in a little further, and a little further yet. She paused then for a minute, and started to pull back out.

Then she pushed in.

Then she pushed in again.

The next thing I knew Sandy was pounding my asshole, having pushed my face down into the cushions of the couch. I was moaning wildly as every thrust hit my prostate and sent an electric pulse shooting through my dick and up through the rest of my body. I could feel my own member start to pulse as the orgasm came closer. The sensation was completely new to me - I'd never cum before without direct stimulation.

I made a move to reach down and stroke myself, but Sandy caught it with her right hand, while her left reached down and did the job for me. Two seconds of pounding and rubbing later I shot my load all over the front of the couch.

We both sat there panting for a minute before Sandy began to pull out of me. There was a slight pop as the tip came out, then I fell down onto the floor. Sandy laid down next to me and we stared up at the ceiling together.

"So I take it you liked being a guy then?" I asked Sandy.

She nodded in reply. "I did miss having my boobs though..." she replied sleepily.

"So do I" I replied, realizing that I missed the sensation from the sim.

We laid there, Sandy's strap-on resting against my leg. It wasn't long before my eyes started to feel heavy with exhaustion and I fell asleep thinking back to our experience in the sim: the memory of cum in my mouth and new ideas forming...

bigrusker
bigrusker
133 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
ZZchromosomeZZchromosomeabout 5 years ago

Clearly this needs a Ch. 3.

AnonymousAnonymousover 6 years ago
Hot idea

Very hot concept, and nicely written. Looking forward to the next chapters.

300bowler300300bowler300over 6 years ago
SEXY

JUST WISH THIS WAS ME AND MY LADY, TALK ABOUT A DREAM COMING TRUE...! BETTY jo xoxo

Share this Story

READ MORE OF THIS SERIES

Crossed Wires Previous Part

Similar Stories

My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
Pretty in Pink Ch. 01 I catch my bf wearing lingerie...and decide to roll with it!in Transgender & Crossdressers
My New Job A college kid undergoes a transformation at his new job.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
Her Presents She had a number of surprises for him.in Fetish
More Stories