Pranked by Girlfriend

--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.

I took a glance at the clock; 12:01 AM. I realized it just turned from March 31st to April 1st.

"April Fool's," Ann smirked at me.

I looked between them slack-jawed, made funnier, no doubt, but the hard-on I still sported. "I don't believe we've met, Ms. Kendrick. How did you get here? How do you two know each other?"

"I have a life outside of you," Ann jabbed, poking me with a foot. "I was an assistant on Woman of the Hour, that's how we met."

"And Ann bribed Sean at the gate with a blowjob to sneak me in," Anna Kendrick said with a huge grin on her face.

"Huh, guess I don't know everything going on here like I thought," I said to myself, still dumbstruck.

"Guess you were right, our legs and asses do look pretty similar," Anna said to Ann. "And he does know how to give a good fucking. Haven't been used like that in ages."

Ann smiled and ruffled my hair. "I think we've teased him enough. How about we give him an honest fuck?"

Anna popped up joyfully, her deceptively large tits bouncing joyfully. "How about it, big boy? Give it to me to my face?"

A smile spread across my face as I stood up. "It would be my pleasure." Ann shoved me forward till I fell onto the bed. She and Anna flipped me over so they could get at my cock. Ann dove straight for my balls, her glasses brushing against my thigh. Anna opened her small mouth and sucked in the head of my dick. She never went down far, but her tongue work was incredible as her small hand flew up and down my shaft.

My beloved girlfriend let my balls go with a wet pop and pressed her lips against my shaft as Anna made room for her. They proceeded to make out sloppily with my dickhead between their lips, tongues flying all around it as they strained to get into each other's mouth while pleasuring me. Both pairs of dazzling blue eyes gazed up at me as their lips met around my shaft, the head resting on their soft cheeks. I nearly came then and there and had to push them away to resist.

After letting me breath for a moment, and the two of them making out, Ann moved to straddle me. "You've already had a go at Anna tonight," she said as she impaled herself on my cock with a loud moan. I considered saying I didn't know it was her at the time, but who am I to argue with that logic? Ann leaned forward so I could suck on one of her nipples while she gyrated against my cock. I felt Anna's face nuzzle against my balls and her tongue start licking my shaft and Ann's pussy. Ann gasped in pleasure, managing to spit out, "Get your pussy over here!"

Anna Kendrick gave one more aggressive lick before moving around to where Ann and my faces met. She settled her perky ass over my face, pushing her asshole into my lips while thrusting her pussy up towards Ann's face. We both dug into our respective holes with gusto. I'd tasted how good Anna was, so I knew what a treat Ann was in for, and I was more than happy to munch on Anna's delicious asshole. We both elicited a scream from Anna when we shoved our tongues deep into her holes at the same time.

"Ann, please, let him fuck my ass!" Anna Kendrick cried. I thrust into Ann's pussy as she gazed up at Anna, plunging two fingers in and out of her pussy and rubbing her clit simultaneously. "Please!" Anna cried again.

"OK, and I'll even let him cum in there," Ann acquiesced. "You just need to follow through and clean it after it's been in your ass."

"Of course, anything, just put it in there, please!" Anna squealed. I threw her off my face, causing her to squeak. Ann hopped off my cock and helped Anna atop, facing away from me.

Ann reached for some oil, but Anna insisted, "I can't wait. Stick it in now!" In I went, my cock wet from Ann's pussy, but nothing else. Anna screamed in ecstasy as she fell against my torso, her unoccupied pussy up in the air. "Oh god, yes! Thank you!" she screamed. I grabbed both her breasts as I thrust into her eager ass. Anna turned her head to lick my face aggressively. I licked her right back, her smooth soft skin incredible under my tongue. Ann dove into her pussy again, licking Anna's clit while shoving three fingers into her pussy. Anna started screaming and bucking wildly, pushing me over the edge. I came hard into her ass as tears streamed down her face, sobbing gasps of ecstasy washing over her.

Anna slid off and shoved my softening cock into her mouth, grabbing a few drops of cum and inhaling the scents of her ass. Ann dove between Anna's cheeks and sucked out the cum from her asshole.

We all laid on the bed in a haze, revelling in our post-orgasmic glow in the early hours of April Fool's Day. I'd really have to come up with something good to get Ann back next year.