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[MF] Merry Christmas - Part 1

Well, I promised to update you guys if things happened over the holidays with Ally and her mom Cynthia, and…well…they did. Not to the extent that some were hoping though, no threesomes, but still some exciting times, and some possible movement towards what someone before called a “Sportsman’s Double”

Like before, at the behest of those involved, the names have been changed. Out of respect for the readers, the rest has been told exactly as it occurred (or as best as I can remember).

So, Ally and I had intended to spend most of our time home together, her not even getting a hotel room because ”We’ll be too busy in yours” she said, but I arrived a day early to, well, try and fuck her mom again. What can I say, I’m a man. Ally still has no idea at this point that I had hooked up with her mom, but Cynthia was a lot less inhibited on that subject than I initially thought. In the weeks between Thanksgiving and Christmas we had been sexting, and she was trying to show me how much better she was at certain things than she thought Ally was, like deepthroating a dildo I had sent her (they really have everything on Amazon, and prime eligible too), and then even trying to stick it in her ass. I let her believe that Ally and I hadn’t done anything like that (I mean, how do you tell a mother that her daughter is a little anal whore?), and was egging her on to get it deeper and deeper, saying she’d need the practice.

I got in on the afternoon of the 22nd, a day before I told Ally I would be there, dropped my crap off at the hotel and headed out to Cynthia’s. Even though I was in a rental, i still parked down the street and walked up to her house. I got to her house and texted that I had a surprise for her, and she should go open the front door. At first she thought it was another delivery, but once she opened the door she quickly realized it was something even better, me. She was wearing white sheer nightie with a bathrobe hastily thrown on to answer the door, though once she realized it was me she stopped trying to pull it closed and pulled me inside with the biggest smile on her face.

“Awww, and I thought I was gonna be flashing the delivery boy again” she said coyly.

“I came here early for you” I told her, and without missing a beat she replied “That won’t be the only time you cum early for me” while reaching down to my hardening cock and giving it a squeeze.

I told her to prove it, and she lead me into the family room and pushed me back onto the couch, quickly getting on her knees and undoing my pants. She took one look at my free cock and went to town like her life depended on it. She was using her hands, her tongue, every trick she could think of to try and get me off as soon as possible for some reason, and it was working. I tried to last as long as I could, but I could only withstand a few minutes of her unbridled enthusiasm before I felt that familiar feeling starting to take over. I told Cynthia I was going to cum and she paused for a second to look up at me and wink before resuming what she was doing. When i started to cum I don’t think she realized it at first because she kept going, but once she noticed she stopped and kept just the tip in her mouth, letting the cum collect so that once I was done she could show me what she had managed to suck out before she swallowed her snack with pride.

Once her mouth wasn’t full she asked me “Well, did Ally ever get you to cum so quickly?”

Shocked at not only her getting me off in record time, but the question that followed, it took awhile for me to form an actual response other than just grunts.

“No, I don’t think Ally is part hoover” I blurted out after catching my breath, which was apparently the type of response she was looking for.

“So, should we move this upstairs, or do you need a minute?” she said, seemingly goading me on.

I didn’t respond, but just bent down and picked her up, putting her on my shoulders with her shaved cunt right in my face, and started warming her up on the way to her bedroom. When we got there she had a good grip on my hair, so throwing her down was out of the question, so I just managed to kneel down and place her on the edge of bed, and that’s when I noticed that the naughty girl had a butt-plug in (I should have probably noticed this earlier, but I was more concentrated on not running into the walls). I asked her what this was doing, and she said that she had bought that the day after I left before, and was using it to warm herself up every day, keeping it in longer and longer each day. I started to play with it before she stopped me and said to leave it in, for now. Not wasting another minute left it alone and dove back in and continued eating her out. She initially lasted about as long as I did on the couch, the only difference being that when she came, I didn’t let up, I just continued lapping away, even adding a finger or two. After she was well beyond warmed up, I got up and lined my now recovered cock at her and it went right in, all the way to the hilt, and held it there to let her adjust. Apparently I held it in all the way for too long, because she stopped squirming and looked up, asking “Well, you just gonna stand there, or are you going to fuck me like you do Ally?” If not for the spectacular blowjob on the couch earlier, just her saying that would have probably been enough to get me to cum, but all it did was make me harder than chinese algebra and give me a burst of energy.

It was off to the races at that point, the room filling with the sounds of us slamming together followed by her crying out in joy, and repeated until she reached down and started playing with her clit. Not long after that she arched her back, rubbing furiously and proceeded to cum all over me, covering me with her juices. Needless to say, it caught me off guard a bit, so I just stood there in amazement while she calmed down and caught her breath. Once she did she looked up at me with amazement, saying she hadn’t done that for a long time, and was apologetic at not warning me about what was coming. I told her not to worry, as I had a funny feeling it wouldn’t be the last time it happened that day, and turned her over and pulled her up on her knees, that beautiful ass up in the air, and that butt plug still securely in place, looking up at me. I gave her ass a sharp smack, grabbing her hips and plunged my cock back in her, resuming the same insane pace as before. This time though, when I felt a pressure starting to build in her, I pulled out and let her cum all over her sheets, then went right back at it, not giving her a second to rest. After a while of this I again noticed her plug, and started to play with it, trying to pull it out and twisting it around inside her. Each time I touched it it caused her to lean forward and squirt again, and again, and again. After thoroughly soaking her sheets, I noticed that familiar feeling and told her I was about to cum again. I asked her where she wanted this load, and she just told me to keep fucking her, so I did. It didn’t take long for me to cum, each burst accompanied by me bottoming out in her, which was enough to send her over the edge again. After what felt like forever I pulled out and collapsed on the bed next to her, taking a moment to just stop and this beautiful woman next to me, hoping that this moment would last…but it didn’t. Instead, she rolled over, looking right at me, and asked if I was ready for the final act.

It took me a moment or two to snap out of my trance to realize just what she was asking, but I eventually caught on when she rolled onto me and turned around, putting her plugged butt in my face. Once my brain fully realized what happening (to be fair, blood was needed elsewhere at the moment), I reached up and slowly pulled the plug from her ass and proceeded to warm up this hole like I had the other, this time she was focused on getting me ready for round 3 with her lips. Not long after though she moved around and grabbed some lube from the dresser, and said that “While I enjoy your effort down there, you’re hard enough now, so just use this”, so I did. After applying more than enough to her ass and using a finger to get enough in so it wouldn’t hurt, she grabbed the bottle from me and proceeded to apply some to my cock. She didn’t get far doing that though, since I told her “Hey, if you didn’t get it wet enough before, nothing will work”, which was all she needed to climb forward and line my cock up. She lowered herself slowly at first, taking her time, and pausing for a bit with my cock applying a bit of pressure to her anus before she finally pushed herself down enough to get the tip in, leading to both of us groaning in pleasure before she continued down. She descended slowly until I was about half way in and paused for a bit, grinding back and forth while asking me “So, did Ally ever let you do this to her?”. Still not sure how exactly to tell her how her sweet little daughter is the definition of an Anal Whore, I lied and told her “We tried once, after Prom, but she said it hurt too much” (which was technically true, but after we had been going at it for an hour we tried again and she loved it so much the people in the hotel room next to us complained to management). This excited Cynthia more than anything, and she proceeded to start going up and down slowly, each time getting a bit lower on the down stroke. Before long she picked up the pace and was starting to scream again, and then loudly came and collapsed backwards onto my chest, which caused me to start chuckling at her, and she joined in once she caught her breath.

I asked her if she had had enough, or if she wanted to continue. “You tell me” was all she said as she climbed on top of me, smothering me with her breasts while one hand reached back and guided me back into her ass. She leaned up and let it sink in practically all the way before she paused and started to get to work fucking me for once. I just layed there watching her bounce up and down on my cock, her breasts bouncing with her, and reached up to play with them, alternating between squeezing them hard and just squeezing her nipples. After a few minutes of playing with her breasts she sped up and leaned up, moaning that she was gonna cum again. She stopped bouncing and sat all the way down on my cock, grinding back and forth, trying to see how deep she could get it in her ass. When she came this time she just sat there spasming, my cock deeply buried in her ass, and when she stopped she fell forward collapsing on me again. At this point I could tell she was getting a bit tired, and so was I, so I asked her if she had enough in her for one more. She let out a quiet yes under her breath, which was more than enough for me to roll her over and pull her to the side of the bed. I placed her legs over my shoulders and pulled her back onto my cock, seeing how far I could get it up her ass this time. I wasn’t playing around this time, wasn’t holding anything back, I got a good grip on her hips and started roughly fucking her tight ass. She loved the roughness of this and looked up at me, holding my gaze as long as she could before cumming again. I refused to let up, not giving her a second to relax. It wasn’t long before she was going to cum again and this time so was I. I told her I was getting close again and she looked up at me and told me to cum in her again. I kept going until I started cuming for the last time that night, filling her ass up with whatever was left of my cum. Each time I pumped more cum in her ass I couldn’t help but watch her face, and I was a bit shocked to see that she was making the same blissful face Ally would make when I came in her, which if I wasn’t already cuming that would have pushed me over the edge again. I stopped thrusting just looked down at her, making that face, and then she looked up at me and pulled me down for a passionate kiss. This was, well, a bit more romantic than I had anticipated, but very much welcome given what we had just done.

We curled up together in the bed, trying to fall asleep before we remembered that we had soaked the sheets, so we managed to get in the guest room before collapsing on the bed and falling asleep in each other’s arms. When I woke up the following morning I realized I had slept in and gently nudged Cynthia awake. We realized that we didn’t have long before I was supposed to “officially” arrive and meet with Ally, so I jumped in the shower while she tidied up (We had wanted to shower together, but both agreed that it was probably a bad idea since we both knew what would happen if we did…). When I got out I was pleasantly surprised to see she had whipped up some eggs and toast. We ate up, devouring the food since we had apparently forgotten dinner last night (worth it), and she helped me find my clothes. After I found everything and got dressed, she walked me to the door, but before she opened it she stopped me said

“Look, last night was, well, one for the record books, for me atleast”

“Believe me, me too” I replied and placed a hand on her cheek. She looked up at me and pulled me into a deep, passionate kiss. I pushed her back into the door, and honestly thought we might try and get a quickie in before I left, but then my phone went off. It was Ally, apparently her flight was early, and she was just waiting for her bag at luggage and would be on her way to the hotel. I was originally going to pick her up, but I told her that I was running a few last minute errands, last minute gifts, and that she should take a cab. Cynthia heard this and when I hung up she kissed me one more time before rushing me out the door. I walked back to my rental trying to hide a semi in my pants, thankfully it went away by the time I got to the car. I managed to make it back to my room and change into some clean clothes before I collapsed on the bed, taking some time to think back on the past 24 hours, and how what was supposed to be a fun, no strings attached romp with the milf of my dreams had turned into something more…

And that’s it for now. Sorry this took a bit longer to get out, I haven’t had as much time as I thought I would, some shit came up at work that’s quickly eaten away at my leisure time. I’ll try and get the second part of this out ASAP, but it could be a week or two, sorry…

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59 MINUTES

I'd been wearing the magic piercing for exactly 57 minutes. It was time to take it out... and yet here I sat, watching my sisters boyfriend pump his cock and get it ready for me to suck with only one thought in my head.

To suck that big dick like the slut I was.

My research had shown that it was entirely safe to wear the magic piercing for under an hour... but exceed that time and you would be permanently transformed by its power - staying female even if you took it out.

The piercing bent reality. Whilst I wore it I was no longer Kevin... I was Kendal. As far as everyone was concerned there had always been two girls in the family. My well behaved older sister Molly, and me... the black sheep of the family.

My manicured fingers itched as I raised them to my plump pink lips. My tight pussy was wet and my nipples were hard as I watched Chad approach with his rock hard cock grasped between his manly hands.

"I know you want this Kendal. You've been teasing me like a naughty slut since we first met. You know you're hotter than your sister, I wanna pound you so bad. I want you to suck my dick."

I giggled and smiled. It felt good to be a slutty irresistible cocktease. My sister Molly was dating a guy far too hot for her. It wasn't my fault I was more attractive than her. It wasn't my fault I was BETTER.

My eyes flickered to the clock on the wall. I was nearly out of time. I had to remove the piercing now or I'd be stuck this way forever. All I had to do was unhook it quickly and I'd turn back into Kevin.

I giggled at the thought of a confused looking Chad standing with his dick out in front of his girlfriends nerdy brother and wondering how he had gotten there. I could always put the piercing back in later and have another hour as Kendal. There was nothing to stop me using repeated sessions to get what I wanted.

But what did I want? I glanced down at my new body. My new sexy body.

Tanned sexy bronzed legs, pedicured toes, smooth skin and a tight shaved pussy. My body smelt of perfume, my hair was long and sexy and my face sculpted and improved by makeup. Best of all on my chest were my boy-killers. Two firm rounded breasts squeezed into sexy white lingerie. Right now Chad's gaze was locked onto my tits. My boobs owned him. It felt so fucking good to be a bitch.

But 58 minutes had now passed. I was almost out of time. Permanently.

59 minutes. It was now or never. My hand went to my navel. I just had to unhook the pin and pull the piercing free. I didn't have to be trapped as Kendal.

I tried to think about the life I was throwing away, but all I could think about was how my ass was so round and slappable. How good it would feel to get bent over and pumped. I was so pretty and fuckable right now, who could say no? My tight pussy was just aching to get stretched out and I wanted to have unprotected dirty sex with hot boys as much as I could. I wanted to try anal too. Having it be Molly's boyfriend was just the icing on the cake.

I looked so feminine and it felt so nice to be girly. Cute earrings shone in my ears and my belly button twinkled with the magic piercing. I looked so slutty, what red blooded male could resist me?

Chad was close now. I could see the precum glistening on the tip of his cock. He was desperate for me. My mouth salivated at the scent of cum, I wanted it.

But time was running out.

I left the piercing where it was and reached out to grab Chad's cock. My white manicured nails looked so hot wrapped round his dick. I began guiding it to my mouth. My lips were ready to suck. My body was eager.

Once I was a boy again I'd probably be relieved. I'd have my friends and my life back. Kendal would just be a dirty dream. Perhaps I'd wear the piercing again... but I wouldn't be trapped this way. I didn't need to let her win.

Fuck that. Bad girls ALWAYS win.

BEEP BEEP. BEEP BEEP.

"What's that alarm?" asked Chad as my phone hit an hour and the alarm went off.

"Don't worry about that it doesn't matter anymore," I grinned. The piercing in my belly suddenly felt more permanent. I realised this was now my new body forever. I was Kendal now and there was no going back. I was so fucking happy to be stuck this way I couldn't even describe it. Being a slut felt great.

"All that matters is that you fuck me before my sister gets home."

I slid my pink lips around Chad's cock and began to suck...

Mmmmh, this wasn't going to take 59 minutes, not if I had anything to do with it.

THE END