--March 2025--
A few weeks ago, I finally asked Ann to move in with me, and she said yes! She didn't have much, so it only took a couple trips with some help from some friends amongst the staff. Noah and Molly were always down to help, regardless of Ann and I giving them head in thanks.
At one of our many shared dinners in the following few days, Ann suddenly got quiet, looking almost embarrassed. "What's up, dear?" I asked, brow furrowing in concern.
"I've been thinking about something since I moved in. There's a fantasy I was hoping to play around with, I just hope you don't think it's weird," she said, staring at her food through her round glasses.
"As long as it's not scatological, I bet I'll be pretty open," I joked.
A smile crept across Ann's face. "Gross," she laughed. "And no, it's not. What would you say to me waiting for you in bed, positioned like one of those sex dolls for you to use when you get in from work? The idea of being used like an object seems fun."
My eyebrows shot up. "Sure, I'd give it a shot. As much as I love when you're active, knowing you're into it might make it awesome."
Ann beamed widely. "Oh good! I think it'll be super hot. We'll see if it's what I imagine and if you like it too. But I'm not going to tell you when it's going to happen; the spontaneity from you is part of the fantasy."
"I look forward to it," I grinned, and we turned back to our dinner. I was a bit disappointed when Ann didn't initiate the next day, but knew she was going to offer herself when she was ready.
The following day, I came in around 6 after a dinner meeting with my new CFO, Marie. She was a tall woman (around six feet tall) sporting brown hair with streaks of grey, though she was only around 40. It looked very charming on her, and she knew it. Her divorce had just been finalized, and she had sole custody of her kids. All her bridges had burned and she was looking for a change of pace, though she wasn't a naturist. She was still not quite comfortable with her own nudity around others, but she compromised with a short skirt and a nice shirt tied up to show her bare midriff. I was surprised by her openness to something so new, she won my respect immediately. Hopefully she'll ease up enough to remove her clothes, but I wasn't going to push.
As I walked by my bedroom, I noticed Ann laid out on the bed, motionless. I set my bag down quickly and stepped in to see her. She wore a silk sleep mask and struggled to not let her excitement show on her face. Her legs parted a shade more in encouragement. It didn't take much effort to get myself hard, her fantasy was starting to work for me. Per Ann's request, I had my way with her, though I didn't go roughly. Her inclination was right, and I really enjoyed it.
She confirmed afterwards that she also got off to it and promised to do it again. Also that I didn't need to be so gentle, that I could be as rough as I wanted. This played out several more times over the coming weeks, with Ann settling on a favoured position; crouched with her ass sticking out. She even took to covering most of herself with blankets to isolate her hips, thighs, and ass so it really looked like a sex doll. Thankfully she was still game for this even as my meetings grew later and later.
One night, I was out late at a dinner party Nick Offerman and Megan Mullally put together. I'd made a feeble excuse to leave earlier, but I couldn't help but stay engaged with the conversation. Amy Poehler and her new partner thoroughly kept my attention, along with Adam Scott and his wife. Adam is even more charming in person than his characters, and I see how he has incredible chemistry with whoever he's talking to. Amy was just as funny as her Parks & Rec days, and we all had a grand time. I also didn't mind getting to hug all of them goodbye at the end of the evening; Amy was soft and surprisingly handsy, and Adam gave some of the best hugs with his lean build.
I dragged myself in around a quarter to midnight, thoroughly exhausted. It was certainly a surprise to see pale hindquarters thrust out from underneath some blankets on my bed in the low ambient light of my bedroom. I'd assumed Ann would be asleep by now. Even in my sleepy state, I couldn't resist her magnificent haunches. I dove face first into her pussy, delighted at how wet it already was. She tasted earthier than usual, but I was hardly one to complain. Pussies taste different at different times, and it was still delicious.
I lapped greedily between her pussy and her ass, tonguing her tight hole as she so loved. After as much practice as we had, she still didn't utter a squeak, though I could sense from her clenching muscles how much she loved it. After 10 minutes of feasting on her holes, I had to stick my dick in her pussy. It was so warm and tight, I groaned loudly in pleasure. I pushed roughly into her, eliciting the smallest of grunts from her; both adorable and sexy. I smacked her ass, which brought out a small yelp, before running a thumb over her asshole. She wiggled slightly as I pounded her fiercely. God she felt good.
I'd just grabbed both her hips to leverage even more powerful thrusting as I prepared to cum, when the overhead lights turned up to their full brightness.
"Hey honey, sorry I'm so late," I heard Ann say from the doorway to our bedroom.
I certainly must have looked silly with my jaw on the floor, trying to connect that Ann was behind me and I must be balls deep in someone else. A shocked yelp escaped my lips as I fell backwards, my cock slipping out of whoever's pussy was in front of me. I fell squarely on my ass as Ann started laughing raucously. The blankets shifted as Anna Kendrick popped out from beneath the covers, laughing just as hard.
