First Time Fucking a Tranny

Crystal looked at Jan who looked at me. We all smiled and laughed a bit.

I said, “Sounds good to me if ok with Jan”

Jan smiled and said “But, how? How does that work?”

“I think you should be on all fours to let Crystal fuck you doggystyle while I fuck Crystal doggy behind you” I mused.

“Ok, but then I don’t get to watch! If I laid on my back could it still work?” Jan asked.

I looked at Crystal and we both shrugged and said “I think so... worth a try, right!”

With that, Crystal moved on top of Jan, put her legs up a little high toward her head and sunk her cock into Jan’s pussy. Jan let out a moan as her pussy got filled.

“Wait, I think I need lube and a condom! And doesn’t Crystal need a a condom?” I asked.

“Too late for that honey!” Crystal said. “Check my bag right there. You’l find lube and condoms.”

I went to the bag and found the lube and condoms. I looked back to see Crystal fucking Jan lovingly in missionary position. It was interesting to watch my wife be fucked but also see a girl’s face doing it. They were almost kissing and it was turning me on.

I rolled the condom on. I noticed they were magnums which was perfect size for me. I guess she likes bigger dicks. Anyway, I put some lube on my cock and got behind Crystal. I hesitated to touch her ass for some reason but I knew I had to get past that so I just went right for it. I put a glob of lube on her asshole and started putting it into her asshole with my fingers. She moaned a light moan and said “Stick that cock in me! I’m ready!”

I gave her exactly what she wanted. I popped my cock into her asshole and quickly started moving back and forth. She wasn’t as tight as Jan but it was still a great feeling. We had a few awkward moments as we tried to find a rhythm but we got it down pretty quick.

I was surprised at how well Crystal took my cock. I know she’s done this many times but it was still amazing that she had the stamina to take my 7 inches in her ass while still fucking the hell out of Jan. Both girls were moaning and grunting and I decided to start fucking harder. I reached up and grabbed a handful of Crystal’s hair and pulled it back hard while pushing my cock as far as it could go. She nearly screamed but I could tell she loved it.

After another minute or so of pretty hard fucking, I leaned over Crystal’s back to see Jan’s face more clearly. She was starting to sweat and was obviously loving it. Her eyes were closed and she was breathing hard. I could tell an orgasm was building but it would be a few more minutes and I knew I wasn’t going to let it happen because I knew she is usually ‘done’ after her orgasm.

So I started leaning in over Crystal and watching Jan while I fucked slower but harder. I was trying to get fully engulfed with each stroke which was forcing Crystal to fuck Jan deeper every time also. Jan opened her eyes and smiled at me through her grunting. She mouthed “I love you’ to me while she was being hard fucked by her BFF. I almost came instantly but there was no way I was going to let that happen yet either.

I backed away and slowly pulled my cock from Crystal’s ass. I was taking off the condom when Crystal asked if I was done. I told her I wasn’t done but I was ready for a new position. She was still fucking Jan slowly while she whispered into her ear. I watched as the two of them started kissing. It actually looked pretty passionate. I watched for a moment and then took my bare cock and placed it close to their mouths. They knew what I wanted and broke their kiss to start licking my cock. I shoved it into Crystal’s mouth while Jan licked my balls. I did this for a minute or so before backing away again to keep from cumming.

As soon as I did, Crystal peeled herself from Jan and laid next to her. Everybody was breathing hard and sweating and needed drinks. So we used this as another opportunity for a break. We started talking about more things to try. Crystal said she was enjoying Jan more than she thought she would and loved me fucking her ass. Jan said she was “down for everything except anal” and I said I was down for anything also. I asked Crystal if she brought any toys. Sure enough, there was a 7 inch vibrator/dildo in her bag. Now I had some more fun ideas.