I sat up and stuck a couple fingers in Judy’s pussy and they slid in super easy. I even got three in with no trouble. As I was sliding two fingers in and out, I tried to gently insert my thumb inside Judy’s asshole. At first it didn’t feel like it would go in, but then it all of a sudden slid in. Either Judy didn’t notice, or she didn’t care, so I pulled out all of my fingers and got behind her and placed the tip of my cock inside her pussy. My dick was instantly covered in slimy pussy juice, so then I put the tip of it against her asshole.
Holding it in place with my left hand, I slowly entered Judy’s ass for the first time. Like my thumb a moment before, there was some initial resistance and then I slid right in. Judy stopped licking Delia all of a sudden and looked back at me with a puzzled expression. I looked her right in the eye and pushed my cock all the way in and held her ass against me by holding on to her hips. She took a sharp intake of breath and rolled her eyes in a ‘whatever’ expression but didn’t push me away.
I started to slowly fuck Judy’s ass and then picked up a little speed. Judy rocked back a little bit and that gave me encouragement. I had fucked other girlfriends in the ass before and now remembered just how much more smooth an ass is compared to a tight pussy. In order to get more sensation, I had to really start fucking her ass pretty hard. As I got going hard and fast, Judy stopped licking Delia and pulled her head up. Delia sat up to see what was going on, and then crawled over closer to get a better look. She started massaging Judy’s ass cheeks and playing with her tits through her dress.
Judy reached back between her legs and started rubbing her clit and pussy and Delia just sat back and watched for a moment. I pulled her close to me and kissing her mouth ravenously for a little while, and then Delia got back down next to Judy and started pushing her hips back to meet my thrusts. Even though I had already cum twice this evening, the combination of feeling my cock sliding in and out of Judy’s ass and seeing Delia’s perfect body holding onto Judy quickly became too much. I gave one last long hard thrust and then came inside her ass as I slowed down my assault.
I pulled out and Judy staggered to her feet, turned to me, and said with a bit of a laugh "Happy?" I said "You bet!" and walked over to the bathroom to clean off my dick. I grabbed a handful more of tissues and walked back to where the ladies were getting straightened up. Judy grabbed some tissue and quickly wiped off some cum that was leaking down her thigh before it could hit the floor. 

Delia said "when are you two going out again?" with a big smile on her face. Judy said "It might be awhile - not sure if I can do that again anytime soon!" The girls hugged and Judy paid Delia her sitting money. I walked over and gave Delia a hug as well before she left for the night. I went upstairs and was asleep before hitting the bed.
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