Transgender
2010-11-09

I have already told you about my first time being Joanna in “my best friend and me”. This is the story of the trip Justin and I took up north.
I have a little cottage up north that Justin and I have gone to many times. We planned to make the trip again on a weekend but this time was different. I had recently let Justin in on my secret; I love to dress in lingerie and get fucked. We planned to go up on Friday night after he got out of work. We would be making the two hour drive at about 11:00 pm.
I loaded my duffel bag with lingerie, stockings, heels, wigs, and a couple of large dildos I had recently purchased. Then it was time to get ready for the trip so I took a long, relaxing shower and shaved my body clean. I slid into my favorite black silk thong and matching bra and slipped into a pair of black stockings. I slowly slid my low cut black dress over my head and started on the make-up. I put on some dark eye shadow and bright red lipstick. For the finishing touches I threw on a black bob wig and some four inch black heels and stood back to admire my transformation. Then my doorbell rang. It was time to go.
I opened the door and handed Justin my duffel bag.

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“Wow! You look great Joanna!” he stammered as I locked my door to leave. I grabbed him by the belt and led him back to the car.
“What’s in the bag?” he asked as soon as we were in the car.
“Just some stuff to make the weekend more fun,” I said seductively.

We had been driving for about an hour and a half when I pointed out, “This road is deserted. ” I placed my hand on his thigh. “I bet there isn’t another car out here for miles. ” I slid my hand closer to his clearly growing erection. “Nobody is here to see us. ” I started to massage his cock through his pants. I found the zipper and brought his cock out. He groaned as I started to stroke it up and down.
“Your cock looks like it tastes so good,” I said. I lowered my head into his lap. I slowly licked the growing head of his beautiful cock.

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“Mmmmmm. It does taste good,” I said.
I slowly slid his cock into my mouth and started to suck. I slid up and down on his huge cock and started to play with his balls. He moaned with pleasure as I started to bob faster. I could feel his cock hitting the back of my throat but I wanted more. I moved faster and faster and I could feel his cock expanding in my mouth.
“Oh Joanna, I’m cumming!” Justin yelled as he spurted hot sticky streams of his delicious cum into my waiting mouth.
“Wow, that was fantastic,” Justin said as we pulled into the driveway of my cottage.
“It’s not over yet,” I said as I once again led him by the belt into the cottage with my duffel bag of goodies in my other hand.

We got inside and I gave him my bag to open. He pulled out a 18 inch dildo and smiled.
“What are you going to do with that?” I asked.
He grabbed me by the waist and flipped me over on the couch. He pulled my dress up over my ass and pulled my thing aside.

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He spit on the end of the dildo and shoved it into my ass. I gasped with the pleasure of being filled like that and he began to work the dildo in and out of my ass. He moved to be more accessible to me and I started taking his pants off as he pounded me with the dildo. Once his cock was free I began to devour it again relishing in the feeling of being filled at both ends.
Finally I could take no more. I had to have his cock in my ass. He pulled the dildo out and replaced it with his cock. He fucked my furiously from behind and I leaned back into him as he would thrust. He was grunting louder and louder and then he reached forward and grabbed my also hard cock and began to stroke me in time with his thrusts.
“Oh fuck! Harder!” I yelled. “Please fuck me harder!”
I could feel my balls tighten and I shot several streams of hot cum onto the floor. Just the I could feel Justin’s cock expanding in my ass.
“Oh fuck! I’m cumming!” he yelled and I could feel the warm liquid fill my ass.
We collapsed on the couch panting. Justin looked over at me and said, “This is going to be a fun weekend.