[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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Lending a Hand, Part 1 [MF] [Long]

Long-time reader, first-time poster. Hoping to make this a regular thing so long as people enjoy! Standard “good stuff starts here: _______” disclaimer applies.

(Upfront admission: this happened long enough ago that some aspects—a.k.a. dialogue—have gotten a little fuzzy. As such, I’ve taken a few liberties to make things read a bit more naturally. But rest assured, the recollections themselves are all true.)

I was in my senior year of university, and my course load was light. Being the go-getter that I am, I decided to get a job—specifically, one that would look good on my CV. After turning over a few rocks and talking to a few friends, I wound up getting a gig with the students’ union. Good work, cool people, and decent pay. What more could a 22-year-old want?

At first, I was sweet on one of the execs—a tall drink of “please sit on my face” named Tessa. Beyond being cute and easy to talk to, she was also the one I worked with the most. But after a couple of weeks, I found myself getting on really well with one of the other VP’s: a curvy redhead named Janice who was as bubbly as she was cool. Played in a band, told funny jokes, and rocked a delightfully tight and faded Velvet Underground t-shirt like it was going out of style.

Since I’d started at the end of May, most of the summer was spent planning the frosh week festivities: booking talent, organizing sponsors, signing up volunteers… that sorta thing. And all throughout, I continued doing my gosh darn best to endear myself to Tessa and Janice. I mean, why not, right? Worst case, I get two stellar references; best case… well, the jury was still out on that one.

September finally rolled around and frosh week went off without a hitch. By the time we got to the final day, everybody involved was buzzing from the combination of success, booze and drugs that had permeated the festivities. A B-level performer (reasonably popular amongst college students at the time) was our Friday night headliner, and man, I’ll tell ya: while some celebrities might be oversized knobheads, he was not. Genuinely great guy who was as nice off the stage as he was talented on it. I can say this with certainty because, after his performance was done and he and his band had helped us tear the stage down, he invited me, Tessa, Janice, and the rest of the team out to one of the bars to celebrate with him and the band. Awesome!

Fast-forward a couple of hours and there we are, drinking and chilling with some seriously cool dudes. Everybody’s having a great time. Out of nowhere, Tessa comes up and wraps her arms around me.

“Thank you so much,” she said. “I hope you know there’s no way we could’ve pulled this off without you.”

“Awww,” I said, returning her hug with one of my own. “It was an absolute pleasure. Working with you guys has been amazingly fun.”

You know how sometimes, even if you weren’t intending for anything to happen, things do? And oftentimes it’s the littlest thing that ends up being the difference between a best-night-ever kinda night an otherwise forgettable one? Tessa’s perfume was that thing. One moment we were hugging as friends. Then I breathed in. Instant erection. Now, I know it’s cliched to say on /r/gonewildstories at this point, but I am bigger than your average bear. By a fair bit, actually. And it didn’t take long for Tessa to figure that out, because by the time I was red in the face and stammering out an apology, she was waving it off as though it wasn’t a thing. We laughed, got another drink, and tried making small talk before deciding to head back to our table where everyone else was. Except right as we were about to turn the corner into the room they were in, Tessa grabbed my hand and pulled me toward the bathroom.

She was on a mission. By the time I had both of my feet inside the single-occupant room, she’d already locked the door, set both of our drinks down on the sink, and started undoing my pants.

“Holy shit,” I said, doing my best to sum up the situation.

“This is what being a good guy gets you,” she said as she sunk to her knees and traced by cock from root to tip with her tongue. Then she smiled at me—just long enough for her eyes to tell me that this was going to be one to remember—and took as much of me into her mouth as she could.

My head fell back and my fingers tangled themselves in her hair, and it took everything I had in me not to cum right then and there. She was that good. Up and down, swirling around the top, playing with my balls: she knew exactly what she was doing and when to do it.

“Jesus fucking Christ,” I groaned. She responded with a moan of her own.

I looked down to see the lower half of her face covered in saliva and pre-cum, her left hand cradling my balls, and her right hand tucked into the crotch of her jeans.

Game on.

I hauled her up off the floor and planted my lips on hers. Our first kiss was as sloppy as the blowjob had been, but easily twice as passionate. Our tongues slithered around one another and tied themselves into knots, and while they did, our hands did everything they could to keep me hard and her wet. After 20 or 30 seconds of the most intense kissing I’d experienced at that point in my life, she pulled back, looked me square in the eye and said, “Fuck me.”

The sink had just enough counter space for me to hoist her up and seat her on it. And as luck would have it, it was the absolute perfect height for fucking. So perfect that I didn’t even have to bend my knees as I eased myself into her for the first time.

“Oh fuck,” she said, grasping my head and pulling me into her neck as I went deeper. “Oh Jesus fuck. Go slow, go slow.”

I’m a big fan of purposeful thrusts. You feel more, they’re more sensual, and every amazing moment seems to last forever. So when Tessa begged me to go slow, I grabbed the back of her head, pulled her forehead into mine, and did just that. Innnnnnnnnnnnn and ooooooooooout. Innnnnnnnnnnn and ooooooooooout. After a couple of minutes of this, her pussy cream was all over my cock and all I could see were the whites of her eyes.

“Uh uh,” I said. “Look at me.”

Once she refocused her gaze, the biggest smile I’d ever seen immediately spread across her face.

“This is so fucking good,” she said. “I can’t believe how fucking good this feels.”

Innnnnnnnnnnnn and oooooooooout.

“I know,” I replied. “You have the most amazing pussy.”

“Oh my God. You’re so deep. I can't—oh God.”

“No, no. Look at me. Look me in the eye.”

“You are so fucking hot. This is so fucking hot. I can’t believe we’re doing this.”

“We are. You and me, fucking in a bathroom. My big cock sliding in and out of your tight, wet pussy. We’re fucking doing it, Tess. And it feels amazing.”

“Yeeesssss,” she moaned.

Despite being lost in the moment, I had the sense to realize that we’d been in there long enough for a decent line to have likely formed on the other side of the door. So I started thrusting faster.

“Oh fuck,” she moaned. “Yes, yes, yes. Fuck me. Fuck me harder.”

In and out in and out in and out in and out in and out.

“Oh fuck, oh fuck,” she squealed. “You’re going to make me cum.”

“Yes, baby. Yes,” I said. “I’m close, too.”

“Don’t you dare pull out.”

I didn’t. A few more strokes and she was squirming all over my rod, biting my shoulder and letting out the hottest, most adorable staccato squeals. That’s what put me over the edge. After a couple more strokes, I thrust into her as hard and deep as I could, bear hugged her with all my might, and came. Oh man, did I ever cum. I don’t recall how long my orgasm lasted, but I do remember that after we regained our senses, kissed a little and laughed a bit more, a stready stream of cum waterfalled out of Tessa’s red pussy as I pulled out.

“Well that was fun,” I said, pulling my pants up.

“Fun? That was fucking amazing!” she responded.

We spent a minute or two tidying ourselves and cleaning our puddle of fluids off the floor (what? We’re Canadian). When we were done, we agreed that she’d leave first, and that I’d follow a few seconds later, mile-high-club-style. Another quick kiss and she was out the door.

I looked myself in the mirror and smiled like an idiot before opening the door and stepping out. Luckily, there wasn’t a single person waiting to use the loo. Bonus.

Beer in hand, I rounded the corner and made my way toward our companions. Apparently we’d been in the bathroom longer than I thought, because despite having arrived with 15 or so people, there only appeared to be five or six left: our celebrity matchmaker/musician friend, a couple of his bandmates, Tessa, and Janice.

I took a seat opposite the girls and smiled at them before turning to the guest of honour. As much as I wanted to cozy up to Tessa and convince her to make round two a reality, I knew well enough to play it cool. For now. So instead, I fawned over Mr. Rockster. Now normally, I’d be hella excited to shoot the shit with the guy. I owned most of his albums and considered myself a genuine fan. But the more we talked, the more I felt eyes boring into me from the other side of the table. So the next time I took a sip of my pint, I casually looked across to see what was up.

Tessa, still wearing her biggest-ever smile, was chatting up the bass player. But Janice… was staring right at me.

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CAUGHT IN LINGERIE!!! P1

It was just another day, my girlfriend was at work and I had the day off. I dressed in my favorite lingerie, put on a wig, makeup, and locked my cock in a chastity cage. I started watching bimbofication porn while riding my dildo, fantasizing about becoming a bimbo. I lost myself in the porn and fantasy, completely unaware of my gf entering the room quietly.

She just stood there smiling as she watched me, moaning as I called myself a dumb little bimbo and a dirty fuckdoll. Just as I was about to climax she started laughing loudly, tearing me back to my senses as I desperately tried to think of an excuse.

GF:Oh my god babe, I had no idea you were such a naughty girl. Let me get a look at you.

She had her phone in her hand, taking photos of me, flushed and sweaty from riding. I tried to stand, tried to run, even though I knew there was no place to run to. She pinned me against the chair, dildo fully in me

Me: I-I-I…….. didn’t know you would be here.

GF: I forgot my purse. Is that a chastity cage? Oooh you are such a dirty little slut aren’t you.

She saw the key and grabbed it before I could stop her. She held it in front of me, smiling.

GF: maybe I should hold onto this for awhile babe. We wouldn’t want you touching yourself now would we?

I stared at her in a mixture of shock and arousal.

GF: I think I’m going to enjoy this, let’s see what you’ve been watching slut.

She turned to the computer and saw every video I’ve watched, commenting and laughing.

GF:Sissy training, bimbofication, bondage? Ohhhhh babe, you are such a dirty slut, aren’t you? I had no idea that this is what you get off to. Well, I guess some changes are needed.

Me: Changes? What do you mean?

GF: Now that I know just how much of a sissy you are, I think that I’ll keep you locked in chastity for awhile. Now come on sissy, time for you to learn your new role in our relationship.