The next morning, I woke up before Kaycee. This time she was still in bed with me and we were actually cuddled up under the covers. As I came to, I realized my crotch was up against her ass and my hand had snaked around to grasp one of her tits.
I didn't budge an inch at first, just laid there with my face sort of buried in her hair at the back of her neck. As I got my bearings I started getting turned on; if things were different this would be a great position to get some morning action going. Sadly, they weren't, so I contented myself to a sneaky feel of Kaycee's breast and got up, grabbing clothes and leaving the room.
I was the first up (probably because I drank the least) and made coffee and messed around on my phone in silence. This was Sunday and my plan was to leave to go home after I felt up to the drive. Eventually JD and some of the others got up as well and we hung out in the living room and talked for awhile. I was a little sad, to be honest, knowing the weekend was coming to an end. Not only did it mean saying goodbye to my friends and going back to work, as amazing as fooling around those two times with Kaycee had been, I knew I would always regret not having ACTUALLY fucked her.
JD told me I should stay one more night, he and his new wife were staying to hang out and enjoy the house, that way they wouldn't need to rush off immediately to their honeymoon. Two of the other couples were leaving, but our buddy Mike and his wife would still be around, so its not like I would be imposing. I told him I'd think about it.
Kaycee came downstairs awhile later and I could tell she was a little weirded out. Like the day before. I acted normal, like my cock hadn't been partly inside her a few hours ago. I bumped into her in the kitchen and we made the normal polite morning small talk. When she asked how I slept I messed with her a little, saying I had been having such wonderful dreams since being in the house.
Her eyes went a little wide and I could tell it freaked her out a little, but I was trying to reinforce her thinking I was unaware of her nighttime activities. We talked a little more about whatever and she mentioned she was going to be staying again that night.
The tumblers clicked in my brain and I knew I had to stay and try for another crack at Kaycee. I emailed my boss and got approved for the day off, then just enjoyed the rest of the day. The other two couples left, but the rest of the group hung out by the pool and grilled out, really making the most of the long weekend.
I never really mentioned anything to Kaycee about staying in the room with her again, and she didn't bring it up to me. Logically, it would make sense that if we were doing sharing a room because there weren't enough beds, once some beds opened up one of us would move. However, the bedroom we were sharing was upstairs and so were the two bedrooms the two couples who left had been in. Once we went upstairs for the night, it's not like JD or anyone was gonna come up to check on us, so if we didn't say anything they would probably never know.
I left it like that until late that night when everyone was heading to bed. This time I didn't do any drunk play acting (I had had a couple beers but I was fine), I just went right up and laid down in the bed. I was trying to see if Kaycee would object, which she didn't.
She did whatever her nightly routine was, we talked for a little about oddball things, totally ignoring the elephant in the room, until we finally turned off the light and settled down to sleep. However, I didn't settle down. The thrill of the last night was on me and my mind was racing. I laid there for at least an hour just waiting for some action to begin. Looking over, Kaycee seemed to be sleeping peacefully.
I had no way of telling what time she had usually been waking me up, so I didn't know if this was normal. Maybe she usually took a little power nap to build up her stamina to suck dick, who knew? I waited awhile longer, weighing options in my mind, then decided to try to get things started myself.
Lifting up the comforter, I inched myself over to Kaycee's sleeping form and got behind her, just like we were that morning, with my cock up against her ass. Reaching over her ever so gently, I grasped her breast and leaned in. I lay like that for a little while, enjoying the proximity and the smell of her hair and my cock started to respond. She still seemed out, so I slowly began grinding up against her a little and gently rubbing her tits.
She startled a little, and I closed my eyes, faking being asleep. I felt her turn to look at me, then heard her say in a low sexy whisper "Oh, you dirty monkey, you like fooling around with me, don't you?"
Yes! She was going for it!
We were still spooning and I was grinding my cock up against her ass through her pajama pants while feigning sleep. "Come here, you little deviant," she whispered, reaching back to inspect my already hard cock. Deftly she pulled it out and cupped it up against her firm ass cheeks, letting it ride back and forth in the groove in between.
I risked a look as she let go of my cock for a second and saw her moving her hands below the blanket. When she slid her ass back over to my naked cock I felt a nice slippery fabric and I was now pointed down between her legs and pressing right up against her pussy. Not only had she removed her pants, she had adjusted the angle to get my cock exactly how she wanted it.
It wasn't exactly how I wanted it, to be sure, but I was playing the long game. We started dry-humping just like that, my hard cock pushing and sliding on her pussy through her panties, which was becoming hotter by the second.
I was a little worried about being a little more aggressive "in my sleep" but she totally bought it. My hand was still loosely cupping her fit through her shirt and she reached up and grasped my hand with hers, practically begging me to play with her tits in my sleep. I obliged her by massaging them gently, then as her nipples became hard playing with their tips. Kaycee surprised me again when she pulled my hand down and slid it inside of her shirt, where I immediately began fondling her naked tits directly.
This was getting super hot and I wanted to start kissing and sucking on her neck, but I didn't want to ruin the illusion and scare her away. We were both starting to breathe pretty deeply and I could feel Kaycee's pussy growing nice and moist through the fabric of the panties. She had her hand between her legs now and was doing double duty, lightly guiding my cock where she wanted it while using her other fingers to rub her clit. Throughout the course of this, our positions had changed a little as well, I was behind her with my dick between her legs but positioned a little lower, while she was on her side with one leg pulled way out to create access for my cock.
I could tell she wanted to go further, like the night before, but I think subconsciously she was smart enough to know she wouldn't have the same leverage in this position to totally control the depth of my cock. That was one hundred percent what I was counting on though, so I wasn't going to let her flip over on top of me.
