The first time me and my girlfriend had sex was the same day we met. She walked me up the beach holding my hand. Her cock flopped all the way, slapping up and down her bikini bottoms, we got stares all the way up the walkaway by other girls and dudes, some winked and did finger guns toward us. Mr Woofer followed us happily all the way.

When we reached the hotel's reception we got some looks from the receptionist, but she was bussy talking to a business suit woman and couldn't really say them anything, not that she really cared anyway. The business woman looked back at them and saw Cassandra's cock out and opened her eyes further but then turned and kept talking to the receptionist about something or other, that wasn't even the most remotely weird thing she'd seen in this city, after all you don't make an exclusive adult oriented resort with strong prohibition of minors without a reason. This was a free sex resort.

Cassandra walked me toward the elevator and pushed the button, then Mr Woofers came and the receptionist said that we should leave him in the hotel's kennel, no pets allowed on the rooms. So we left my dog with the carer, who looked up and down at Cassandra and me and winked at me when he though she wasn't looking.

"People think you got quite a catch," she said to me when we got back.

"Oh... I think it too," I said to her. She grabbed me stronger on a side hug, "Oh, I'm gonna FUCK you," she said laughing. My tiny cock got even harder, I could probably cut diamonds with it. We got to the elevator and she pushed the number six, "I got room nine," She winked at me. "Nice," I responded.

I turned around, she was wearing flip flops and still my eyes were around her lips, I looked up at her and jumped to her lips. Her hands went to my back and she pulled me up, my lips were on fire, her's were water, I couldn't keep out of the lock that had formed among them. I drank from her lips, from her tongue, my hands found her butt and I grabbed it with both of them. It was soft and squishy. The elevator pinged and the door opened, an elderly lady got in carrying a leash from where two twentysomething girls where tied and looked at us. She smiled and stood at a side. We relented on our kissing and stood hastily to the other side. Cassandra's cock was all over the place, no longer contained by the least by the fabric of the bikini. "Mistress Jessica," Cassandra said to the woman, "Cassandra," She responded with a nod and a smile, "got yourself a good one?" she asked. "We'll see, have some hopes so far," I started blushing to the side and shifted a little. Mistress Jessica laughed and nodded again, "Have fun you too" she said when our floor finally arrived.

We got to room 69.

As soon as the door closed she took off the top of the bikini, her huge tits flopped down heavily, my head went immediately toward them and I frothed them all over my face, my mouth going directly toward her hard nipples and slowly licking them all around. I couldn't get over the idea that I was dreaming. I stood back a few paces and just looked at her in all her glory.

"take off your pants," she said. I blushed, my tiny cock had always been my worst fear, how people react to it means everything and I read too much on my own value as a man from it, again, now from years of being the boyfriend of a girl whose cock is an order of magnitude bigger than mine I can say I read too much into it, but back then it was everything, so I took some time to do it, she never hurried me tho, letting me took my time. After mustering will for a a while I looked back at her and saw her smiling at me, her glorious cock hanging erect, her round tits glistening with the sweaty remains of my licking. I took my bathing suit and threw it at a side. My tiny cock had receeded with the fear and anxiety, but it was growing to it's little power back again.

She dropped to her knees right there and put it all in her mouth without saying a word. I was shocked, but my little soldier responded to attention immediatelly and I was back at full erection in seconds. I have to say too, that to some regret I also came almost one minute into it. I had been getting aroused for the last hour or so, so don't judge me. It was so much cum. Ropes after ropes of it, I couldn't believe it, I had never came so hard before. It started in her mouth, but soon she took it out and ropes of cum covered her whole face and hair. She kept playing with my balls and liking my tiny friend over and over while i came. My legs fainted and i had to grab the side of a table to avoid falling down.

"Holy shit pretty boy," she said, her face like a bukake actress, "you were pent up or what?" I nodded. "It's been a while." She laughed again, getting up and scooping cum from her face into her mouth, smearing the rest all over her tits. I couldn't believe how erotic she was, even after cumming like a hose I just wanted to keep going. She took my face and gave me a wet kiss, I could feel the goops of cum still sloshing around and she started to share my own cum with me while we exchanged saliva. I could feel the sticky substance in her huge tits too, and her pocking cock pushing mine to a side.

Her penis was so big that I could feel it pocking at my ass from the front, "I'm going to fuck you now," she said to my ear. I shivered. "Yes, okay," I just agreed. She went to the room and came back with a large bottle of lube, it was almost as big as her cock. A measuring unit i'd be using from now on to her amusement. She grabbed me and turned me around, like if I weighted nothing, and pushed my legs appart kicking them with her feet. Squirted a large amount of lube on her hand and started to smear it around my asshole. She kept adding more and more, slowly inserting a finger at first, but then she placed the nooze of the lube bottle up there and squirted a hard pump, I reacted surprised feeling the cold liquid go far up my ass in a second, she kept nudging more and more lube while using more and more fingers to strecth my hole. Finally she gave me as kiss on an asscheek and said, "you're as reddy as yallbe."

She stood up and put her hand on my back, slowly caressing me, "are you ready pretty boy?" She asked, I was about to say yes when she pushed it in.

The world stopped for a second.

I could feel the head of her cock just resting there, filling me up like nothing had ever done. For some reason I started to cry, not pain, no, it was a feeling of completion, of oneness. I felt like i had found something i had been missing my whole life.

I always knew I needed a big cock to be happy.

I just didn't knew it didn't had to be mine.

And then she started to push it further. It was painful, but not unbearable, she kept pushing and pushing, when my mind said that she couldn't be so big she kept going. And then i felt her balls hitting my cock. She bend over and kissed my neck, "easy pretty boy," she said at my ear, "now the fun starts." I could feel her massive tits on my back and the heat of her body. She pulled out almost completely and pushed back in, the whole process repeated, again, and again. Slowly. Filling me completely. And then her rythm started to accelerate. My mind went away. I was on pure bliss. I could feel my tiny cock trembling each time her balls slapped mine, she pulled my hair up and turned my head so we could kiss. It was awkward, awkward as fuck you could say. She let me go and picked up even more faster pace. Pumping and pumping. I dissapeared, I only existed for her to obtain pleasure. And then, after long enough I lost track, she pushed full up my ass, her whole cock pulsating and getting even bigger, she started to cum, over and over again. If i had cum incredibly before hers was like floodgates opening, so much warm goo filled my ass for almost a minute. She kept her cock up my ass while she layed on my back, her breasts pushing and transmitting heat, her lips kissing my face.

When she finally removed herself from me i could feel the slushing cum dripping out my gaped hole. She turned me around and kissed me again, her wet cock on my leg, now chubby but not erect anymore. She pulled me up the table and i couldn't stand properly, my legs failing me now with my asshole destroyed. She laughed and pulled me up, walking with me toward the bathroom's shower.

That was the moment i knew i'd do anything for her, my girlfriend cock is bigger than mine, and I love her.

I had never been so exhausted as I was that evening, getting your ass drilled by a giant cock for the first time takes a toll on you. I passed away on her bed, snuggling my head among her generous tits. I could hear her heart beating, and the warm heat of her skin.

When I woke up back my ass hurt, I carefully untangled from her arms and went to the bathroom. When went back to the room I stared at her. She was snoring lightly, her arms open to both sides, her tits falling to each side and leaving her chest skin tensed. And her cock. Oh good gods her cock.

I sat on the bed trying not to disturb her and got my face right next to it. It pulsed slightly with her heartbeat, the balls moving on their own accord, big and heavy. The rugged skin of the sack changing everytime one of the balls changed their location. I could see one or two stray hairs that had escaped trimming.

I was now kneeling with my chest full on the mattress, my hand slowly reaching and starting to caress her. My own penis was as hard as it has ever been. But I really didn't care for it too much at the moment. That is something that I've come to realize with the passing years with her, my cock isn't as important as hers, and giving pleasure to her gives me more pleasure than I ever got using mine. That doesn't mean that she doesn't give it it's fair attention, but as I said, I just enjoy more using hers.

In any case, this was the first time I spent appreciating her cock. I wanted to see it growing, so I started to caress it, slowly. Her reaction was instinctive, a spur of movement, and then slowly blood started to flow into it, and it grew under my hands. Her head pocking half way out of the hood, pink and wriggly, a drop of precum glistening in the tip. I used it as lube and started to play with the head exclusively, it kept growing out of the hood.

She kept slowly snoring all the way. I just felt so happy that I wanted to kiss her, so I did. I kissed her balls, I kissed the base, I kissed every inch of the shaft, and then I kissed the head of her cock. More precum had flowed out of it and it tasted salty and good. I liked it. Then I liked it again. Then I liked all around and over down, back to her balls. I got one of her balls in my mouth and then kept licking back up. Her cock was now a sloppy mess.

My mouth found the head again, and I tried to suck it all in my mouth, it was harder than I expected, my theeth where in the way, and it filled most of my mouth just the head alone! I took it out and liked it again, back down the shaft and up, slowly strocking her. I got the head again in my mouth and started to lick it all around, turning my tounge while i strocked the rest of it.

I felt her hand in my head scratching it.

"Good boy," she said getting her hands on the back of her head and looking down at me. I looked up from her legs without taking my mouth of it and kept sucking and licking, while I strocked her methodically, not rushing it but just going up and down. Letting my flowing saliva and her precum work their magic. She moaned sexily at me.

I don't know how long I was down there, my mandibles hurt from the uncommon practice, and my stomach was complaining from the weird bent possition i had kept for so long, but at a moment her hands fell next to her, she grabbed at the bedsheet and started to piston up, surprising me. I almost chocked at the force but I don't think she even realized she was doing it, because right there she started to moan more gruntly, becoming almost screams. And cum started to explode in my mouth, I chocked again at the sudden substance going the wrong direction, but then started to drink as much as I could, i kept strocking and sucking, but then she complained, "stop! Stop! I can't." She said.

I took my head out of hers and stray ropes of cum covered my face, I still had a good mouthfull of it that I had dried out in the last seconds and decided to repay her the present she had given me earlier, so I stood up and kissed her, giving her a good taste of her own produce. She kissed me pationally for a long time, gulping with me the rests of her cum.

"You are a keeper," she said to me after our kiss. She didn't knew how much I already loved her.

This is really excellent. Thank you for posting, and please keep it going!

The next morning came later, my face was stuck to the skin of her neck by the dried cum. I moved my hand to rub my eyes and in the way there it bumped one of her massive tits. So I let it there and started to caress her nipple. I also started to kiss her neck.

"Good morning pretty boy," she said to me with fun in her voice.

"Good morning beautiful," I answered kissing her in the lips. She returned the kiss. We stood there kissing with my hands teasing her tits for a long while. I looked down at her crotch and her boner was there, poking to the gods.

My ass was still somewhat sore of last night abuse, but my mind disregarded it and I took another bottle of lube that was next to the bed. She smiled at me showing her teeth and asking me, "Are you sure?"

I nodded, pouring a generous amount of lube on her. I stroked her morning wood a few times to get it all distributed and straddled up. Cowboy position. I took her cock and guided it right to the opening of my ass. And slowly, very slowly, got it all inside. My balls and cock resting hard on her toned belly.

"Ride me boy," she demanded. I obliged.

First very slowly, but soon with pneumatic rhythm that she seemed to enjoy, and my ass demanded. It was so delicious, like fitting something on a hole that has the perfect shape for it. I rode her cock as if it was all a dream and if I stopped it would end. She let me do all the job, letting me control the pleasure she received from my ass. I know she wanted to start pistoning more than once, I could see her muscles twitching, but she controlled herself, letting me get my pleasure as well.

"Oh god, Oh God!" she started saying, I could feel her trembling. My body was lost in the pleasure, my own cock trembling of unattended excitation, my eyes went back on my head and I started to push faster, my cock started to spew cum seconds before hers exploded inside of me. She was incredible.

I fell over her with her cock still in my ass. I kissed her and hugged her.

"You are the best thing that has ever happened to me," I said to her, kissing her neck, and then the silliest thing I could say came to my mind, "do you wanna go out on a date?"

She started laughing, her cock popping out of my ass and her cum dripping out, she hugged me and laughed again and again.

"Is that a no?" I said half dejected, I didn't want our relation to end here in just some casual sex, even though more than half the time I had knew her I had been impaled by her cock.

"Don't be silly Jon, of course I'll date you!" she said hugging me stronger. "Any boy that can take my cock more than once and come back deserves a chance." She kissed my head.

There was a knock on the door, Cassandra called them to come in. A voluptuous woman in a latex maid costume entered the room.

"My lady has ordered me to clean your room as punishment Miss Cassandra." She said kneeling.

Cassandra's cock was still covered on cum and the maid was looking directly at my cream pied asshole.

"Very well slut," she said, "prepare us a bath and then clean this sheets, also get some clothes for my boy and me, we're going on a date."

The maid nodded and went away.

"Wow." I said looking at her. "You're a mistress?"

"Don't worry boy, that's just my job. But I'll fuck you for fun."

I hugged her again and we stood like that until the maid returned telling us the bath was ready.

This is really excellent. Thank you for posting, and please keep it going!