The Family Photo (Homoerotic)

The Family Photo (Homoerotic)

The party was wild! My Mom, Cassandra (Cass), and her Boyfriend, Zoey, were throwing a huge sex party for all of their friends to celebrate Zoey’s promotion at her job. Both of them were pretty big in various, but normally separate, kink communities. As such the end result was RIDICULOUS! 

Mom and her boyfriend had rented out an entire hotel and every single room was full, most of them at capacity. At first, they’d been worried that the two groups wouldn’t mix. Mom was a swinger, and was into the BDSM scene as well. But Zoey’s group consisted entirely of kinky people whose gender was ambiguous in some way, or at least had been at some point. Some of them were men now, others were women now, and many, including Zoey, had found a balance and a willing partner to share it with. 

Zoey was pretty well hung. But she also wore an even more massive bra size than my Mother did. I think that people from both groups didn’t know if they’d be into it at first. But, when you take a community that has a lot of bi-people in it to begin with, and introduce them to skillful kinksters whose gender they often couldn't even guess, it turned out to be a hell of a time! 

With the whole hotel to ourselves, there was sex in and around the pool. Specialized rooms with specialized equipment in every conference room, and more than one couple loudly thrusting into one another in the stairwells. 

As for me, when Zoey and Mom first got together, he was anxious to win me over, and since I was 18 (now 19), it didn’t take them long to figure out that convincing my Mom to let me come to a party or two would do the trick. At first, I tried really, REALLY hard to avoid my Mom at these things. First and foremost, because she WAS my kink. I’d had incest fantasies since I’d started having fantasies. But it took less than two kink events before my Mom found out and confronted me. She tried to calm me down, and assuage my fears at first. 

But when I was struggling to believe that she wasn’t secretly pissed at me, Mom got this mischievous grin, and said, “Hmm… now, whatever can I do to convince you.” Immediately followed by a shout through the house of, “Hey babe! Could you come here please?” Then, once Zoey showed up and I was sure I was in double trouble, Mom just looked from him, to me, and said, “I think I feel like making out… aggressively.” Then, leading Zoey to the couch with a hand on his crotch, she pushed him down, mounted him, and began to do exactly that!

They moaned, and kissed, and Mom rubbed Zoey through his pants, and he started rubbing her right back through her top. After a few seconds of me standing there in stunned silence with a serious hard-on growing in my shorts, Mom paused for moment. She was panting, and smiling lustily as she looked over at me and said, “Normally, you have to leave the room for this… but since we’re all learning to open up with one another… You can stay if you want to.” Then she shot me a wink. Leaned back, and pulled her shirt up over her head to reveal that she was braless underneath! And just like that, her and Zoey went back to getting hot and heavy right in front of me. 

They didn’t do it or anything. But it was more than enough to give me masturbation fuel for a year! Fast forward several months, and I found myself at a party with all kinds of horny, crazy, and gorgeous people. 

I had to admit, I was one of the people who was a little weirded out by not knowing what was under the hood at first. I’d always thought I was as straight as they came. But, Zoey had challenged me on that. The first time I went to a party with Zoey’s kink group, he checked in on me to make sure that I was okay in that environment. When I told him that I wasn’t sure, he said to me, “Let me ask you a question; honest answers only, okay?” I agreed, and he then asked me, if I caught him and my Mom giving double blowjobs to a guy, and after the guy came, one or both of them asked if I wanted that guy's spot, would I say yes. And, I’ll be damned, the answer wasn’t no. I really had to think about it, which was kind of the point. 

Zoey took the questioning further, saying, if I did that, and a week later, Mom asked if she could have Zoey and me in her mouth at the same time, would I refuse? And then, before I could answer, He said, “There are a lot of ways that you and I could share your Mom if she was willing. But she’s pretty kinky. So maybe. And what if there were two more guys and 1 more girl there? Would you say no then, or be open to new stuff?” 

At the time, I admitted that I wasn’t sure, but Zoey just wanted me to think about it. Sure enough, fast forward to today, and while I wanted to sneak away from my Mom so she wouldn’t catch me in the act of asking someone to do some Mommy Play with me, it turned out that I had no such reservations when I ran into Zoey. 

Zoey and I were talking, when this total MILF came up to us and started flirting with both of us. I was eager to get to know her better, when out of nowhere Zoey turns to me and says, “You know, my girlfriend, whom you also like. She loves getting her ass eaten out. Like, it’s a huge turn on for her.” Then he turned to the woman who was chatting us up and asked, “Would it be okay if my young friend practiced on you?” 

I knew, for a fact, that such a cheeseball line couldn’t possibly work. I KNEW it. And yet… 5 minutes later, I was naked in the Sauna, laying on my back, eating this woman’s ass out in preparation for a fantasy I wanted to have later on, of impressing my gorgeous Mom with my newfound rimming skills. 

Zoey really knew what he was doing, and between the two of us, our mystery MILF came three times before she said, “Oh! Wait! That’s my Sister! I’ve gotta go!”. She got up off of my face, and ran off without so much as a thank you. But before my eyes had even adjusted to the light, another woman stood over me and said, “Is this seat taken?” 

Next thing I knew I went from rimming, to muff diving, and I was eating out some random beauty. No sooner had I started than Zoey loudly warned me, “Incoming champ!” I had no idea why, but since they’d started dating, Zoey had started calling me champ and my Mom had started calling me slugger. It was weird at first, but it’s amazing how fast a new thing can become totally normal. 

Anyway. Zoey gave me the warning, and next thing I knew a large, soft pair of tits was dragging along the top of my thighs as Zoey bent a woman over, and positioned her so that her face would be wonderfully close to my cock. And that worked for me, because my cock was feeling pretty neglected. The woman whose ass I’d eaten had been making out with Zoey while he rubbed her clit. And the new woman, whose face I hadn’t even seen yet, had sat on my face with her body facing away from my dick. I got the impression she was putting on a show for someone… who I also hadn’t seen. 

But these parties were like that, and sure enough, no sooner did I hear Zoey start driving his cock into the new woman than her moans were muffled by my cock in her mouth. She started to give me the kind of professional level, mind blowing blowjob that I’d learned in the last year was common in kink circles and pretty much nowhere else!

I was about 15 minutes into the total professional paradise that was this woman’s mouth, when I heard the guy that Zoey had hired to do some  professional photography for the party guests ask if it was okay if he got a photo of our little foursome. 

Zoey laughed, and said they were okay with it. The woman on top of me said she’d love a photo, and… her voice was strangely familiar. But then, there was a slurp followed by the pop of lips pulling themselves greedily up off my cock, and a voice that I DEFINITELY recognized laughed and said, “Sure, why not. Family portrait!” 

She laughed some more, and the confused photographer repeated her words back at her as a question. “Family portrait?” Then, the most familiar and recognizable voice of my life explained. I could “see” her in my mind as she gestured to herself and said, “Mom”, then, “Boyfriend”, and to my increased surprise she gestured back and said, “My Sister, so… Aunt”. Then she wrapped her lips around the head of my cock and gave it one more loving suck before finishing out with, “And this fine young man, is my Son. He didn’t believe me when I said I was okay with his Mommy fetish, so I thought I’d suck his cock dry and settle the matter.” 

At her words, my cock hardened even more. I bucked so hard that my dick slipped from her hand and slapped my Mother in the face, no doubt splattering cum across her cheek as it did. But again, her reaction was just to laugh. Then she got her grip on my cock again, placed a sweet little kiss on the head of it that sent shudders of pleasure throughout my entire body, and said, “Hold your horses slugger, Mommy’s not going to leave you hanging. I just need a second.” 

Almost a minute passed as, presumably, the photographer got over his shock, and took some pictures. But once he was done, Mom spoke up again. 

First, she ran her tongue slowly up the length of my cock, and swirled it once around the head at the top. “Oh my goodness baby, this thing is huge!” She said, before starting at the base of my cock and licking her way gently to the top again. “How could you hide this from Mommy for so long!?” It felt like she had this plan to keep teasing me and saying more, but the next time she delicately wrapped her lips around the head of my cock, her whole body lurched forward, and all she said ended up was“Mrphm!”

After that she was bobbing her head, licking my cock, and moaning around a mouth full of it; only stopping to moan out a quick, “Yes!”, or “More!”I could feel Zoey fucking her! Both from her tits stroking along my legs, and from her lips occasionally being forced down down the length of me with a surprised moan.

I honestly have no idea how I didn’t cum. It was my ultimate fantasy, with my ultimate fantasy woman, in a place where I was surrounded by sex noises and other fantasies. I shouldn’t have lasted 10 seconds. But maybe because it was too much, I somehow held on. I felt like I was moments from being pushed over the edge the entire time. An endless wash of pre-orgasmic bliss. But by the time I heard Zoey cum in my Mom, and felt Mom’s moan filled, screaming approval as she came along with him; but with her lips clamped halfway down the length of my cock; I still hadn’t popped yet. 

Somehow. 

A couple of minutes later, I heard my Mother’s voice again. She’d taken her mouth off of me shortly after the sex had stopped, and was now telling my Aunt to move. I heard my Aunt call my Mom a greedy slut, which was answered with a playful shove and both women laughing. But sure enough, My Aunt moved away, and my eyes once again struggled with the light of not being buried in an ass or a pussy for the first time in god knows how long. 

Mom, like the sweetheart that she was, stood over me and waited patiently for my vision to clear, and for me to catch my breath. Which, thankfully, also gave my dick some time to calm down so I might last through more than just the sight of her naked. When she was sure that we were locked in eye contact, she smiled down at me sweetly and, with a mix of tenderness and playfulness in her voice she asked, “Mind if I sit down?” 

Holy Shit! 

My Mom was asking me to eat her pussy!!!

I said yes. Then remembered the whole fucking, “do you mind” thing meant that the question was backwards, so I shouted no. Then, feeling like I fucked it up again, I clarified that, I didn’t mind, and I wanted her to “sit down”. 

Mom just smiled through it all. Understanding. Patient. And most importantly, naked. I’d seen her topless only twice now that I could remember, and it was just as amazing the third time. I was pretty sure I would never get used to, or tired of, the site of those amazing tits. 

But soon enough I was getting a closeup of her pussy, and nothing else. Nonetheless, I was determined to show her that I could be good at this. I gave Mom my all, throwing everything of what I knew into trying to make her cum so she would want to do this again. 

It didn’t take long to figure out that Zoey had cum inside her, but I wasn’t about to let that distract me. What DID distract me, was a few minutes in when someone grabbed my neglected, but still at full-mast cock, and gave it a few testing strokes. Then I heard Zoey say, “Whaddya say Champ? I’d love to show you what I can do with this mouth and, if you like it, maybe the three of us could take this act home with us after the event.” 

I tried to answer, but Mom’s hand came down and ruffled my hair before she teasingly said, “Don’t talk with your mouth full baby.” I took it as a legit lesson in how to play with them. I thought about it for a second, and gave the general area of my crotch a thumbs up. I was rewarded for my communication skills a moment later with the feeling a new mouth bobbing up and down on my cock. 

Zoey was good, but, somehow, Mom was better. That didn’t seem right, since Zoey had a dick and Mom didn’t; but it was true nonetheless. 

Still, Zoey’s attentions were a hell of a distraction, and it turned out that making Mom cum was way harder while someone was playing with my balls, stroking me, licking me, and generally sucking me towards orgasm. In fact, I was no longer sure that I would be able to do it all, when Zoey choked, pulled his mouth off of me, and remarked to my Mother; “Fuck but he’s big Cass! Your Son is making me gag on this giant fucking cock of his!”

At Zoey’s words, Mom’s thighs clamped down on my head, and she started riding my face like it was sex toy. I reached up and grabbed her ass, using all of my strength to force her into place so I could keep the pressure steady on her clit while she came! It took everything I had. She was riding me like an absolute wild woman, but I was rewarded with an extremely loud and vulgar orgasm as Mom bucked, trembled, cursed, moaned, and whimpered her way through the experience. 

I knew she was done when she started begging me to stop and tried to pull away. Only then did I release my death grip on that amazing ass of hers. 

It was kind of crazy. I’d never eaten ass before that day, and yet, letting go of my Mom’s, I had the strongest urge to get my tongue in hers, and make her moan from that end as well. 

I was too high on having made my Mom cum to follow through on my own pending orgasm, and after a minute to catch her breath, Mom shooed her boyfriend away from my cock the same as she had shooed her Sister away from my face earlier. 

Once Zoey had moved, Mom slid her soaking wet pussy down the length of my body, and sat on my stomach muscles. Having her pressed into my naked skin there, I’d never been so happy to be made a mess of! I wanted to flex my stomach muscles, or grab her and slide her around. Anything to get more of her on me, or to be the cause of another one of her moans! 

Mom was looking very pleased as she panted, and tried to catch her breath while sitting naked on my stomach, and I was very pleased by getting to watch her while she was looking that way! Eventually she reached out a hand, and stroked my cheek. “Oh sweetie”, she purred. “That was SO good! You have been… SUCH a good boy today!” The odd compliment made me blush for some reason. I certainly wasn’t expecting it at age 19. But I expected what came next even less as Mom followed it up with, “Ask me.”

Her hand stroking my cheek felt so good. It was a different kind of pleasure. A different kind of bliss. But still really good! I felt like I’d missed part of what was said, and I think I gave her a confused look. But my confused expression was rewarded, when, with a wickedly suggestive grin, Mom leaned towards me and in a low, seductive tone she said, “Say, Mommy, what does my being a good boy mean.” 

And I gulped. She was just, WOW. It was like having the goddess of sex and desire poke her head out of the clouds and whisper something so naughty that no one had ever thought of it before! It took me several seconds to find my voice and be able to speak again, but when I did, you can bet your fucking ass that I repeated her word for word!

“Mommy, what does my being a good boy mean?” I asked. 

“Oh sweetie,” she replied, with barely restrained lust. 

Then she lifted her hips, and grabbed my cock with a cool, delicate hand, and said, “It means Mommy is going to reward you.”  And when the head of my cock met the warm, wet lips of my Mother’s pussy, I threw my head back, arched my whole body, and moaned so loud it was practically a scream. 

In the following moments, my body was wracked with pleasure. Every muscle in me tensed, and spasmed. Every nerve screamed with delight, and, inch by inch, I felt my cock disappearing into heavenly pleasure, as my own’ Mother’s pussy swallowed me up and gripped me from all sides. My hips spasmed a few times, and twice my Mother warned me through pleasured cries of her own, “Gently!” 

Eventually, she finally managed to get her pussy all the way down the length of me, and both of us just gripped one another, and gasped, and moaned, and panted with pleasure so intense it bordered on agony. When, after several minutes of adjusting to one another, we were finally left breathing heavily and coated in a sheen of sweat, we both had a kind of, coming to moment. As if we’d been in a coma or something. 

The people around us were standing slack jawed, and my Aunt was sitting on one of the nearby benches masturbating. A few people I didn’t recognize had joined us at some point, and one of them randomly commented, “Holy shit that was intense!”. They were immediately corrected by a different stranger who countered, “It was fucking HOT is what it was!” 

I don’t know if they knew what they were watching or not before that moment, but when Mom said, “Okay Son, ready for Mommy to start moving?” Several people moaned out loud, and my Aunt lost her shit. She started screaming and cumming loudly, and, while before I might have been desperate to stare at her and memorize that moment for later use, in this moment, it was impossible to take my eyes off of my gorgeous Mother. She was naked, breathing heavily, and sitting on my cock. It was the hottest thing I had ever seen up to that point!

Mom looked down at me and asked, “Ready to cum now slugger?” 

As someone who had lasted for like an hour up to that point, I was pretty sure I could make this last. I let my confidence show in my face and I told Mom, “I don’t think I’m going to cum just yet”. But my smugness went away, and my confidence melted as Mom’s reaction to my boast was a smile that seemed to say, “Oh you poor sweet boy.” 

Mom lifted her hips a bit, and I felt every fraction of a millimeter of that move, as the most incredible pussy I’d ever felt gently dragged itself along the part of my body that had the most nerves whose specialty was pleasure. I dragged in a hissing breath, squirmed, pounded my fist, and, finally, let out a gasping breath when she got to the top of her climb and finally stopped. 

I looked up at Mom again, and found her starting softly at me, with those intense, beautiful eyes of hers. “All the way down?” She asked, her tone sounding innocent. Then she got a sinful little grin and answered her own question, “All the way down.” And, just like the rise, her descent was tortuously slow. She dragged cries and moans from both of us. My only consolation was the sight of her shaking head while moaning and whimpering, as she teased herself right along with me. 

When she bottomed out again, I was once again in that INCREDIBLE place where I was all the way inside of her. It was just so.. WHOLE. So filling! It wasn’t just pleasure, it felt good on so many levels! Just when I thought that this slow, excruciatingly pleasure filled torture was what the rest of my life was going to look like, Mom did the most incredible thing. She started bouncing! It might have seemed mundane to an onlooker, but it barely seemed possible after how intense just a slow rise and fall had been. 

Mom started slow enough, but even that took it from feeling surreal and amazing, to feeling like something that was going to make me cum, and fast. She was so wet, and as she slid up and down the length of me, the way it felt shifted completely. I found myself already building towards an orgasm that was nowhere in sight seconds before. And just when I thought it couldn’t get any more intense, Mom’s voice, in between moans, rang out with, “Well don’t just lay there sweetie. I know how long you’ve wanted to do this.” Then she took my hands, and placed them on her tits, and I bucked up into her so hard and unexpectedly that she let out a high pitched yelp before following it up with a heartfelt moan. 

After that, there was no holding back. I had my Mother’s tits, in my hands!!!! Her riding me began to build my orgasm with every happy little bounce, and moments before I could warn her that I was going to cum soon, she leaned down a bit, and whisper fucked my ears with the words, “Give it to me”, spoken mostly as a moan of pleasure. 

It didn’t matter that I was on the bottom then, I NEEDED to be fucking her. I grabbed Mom’s hips, and pulled her hard down into me even as I laid my feet flat, arched my back, and began to fuck her back so hard and fast that I thought she might break her teeth if she didn’t clench them and do a better job of holding the fuck on! I came with a roar, and Mom was screaming right along with me as I pumped blast after blast of hot cum up into her pussy. 

We laid there breathless, exhausted, giggling, and pleased beyond what should have been possible for, I don’t know, fucking forever! It was a LONG time. Eventually Zoey and my Aunt helped us up. It turned out that my Uncle had joined us at some point as well. 

As for the rest of the event… we all but ignored it. Mom, Zoey, and I all locked ourselves in our hotel room and fucked one another senseless for the whole rest of the weekend, only pausing to invite in my Aunt or Uncle, or occasionally a random stranger (stranger to me, Mom or Zoey always recognized them). By the end of it, my shyness about whether or not I was with a guy, a girl, or someone who identified as in between was gone! And when we all went home at the end of it, it didn’t take long for Mom to put her new favorite, “family photo” in a frame by her bed. 

Some weeks later, I remarked to her that it was a huge distraction. When she asked what I meant, I told her, “Well… coming in here and seeing a picture of you smiling at the camera, naked, while you are getting fucked and slapping my cock against your cheek, believe it not, gets me really fucking horny! Like, immediately!” But Mom just sauntered over to me, through her arms up around my neck, and sweetly intoned, “Now Son… that’s exactly why Mommy keeps it there.”

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