The Redo
This was an important hookup for me! This guy, Drew, and I had met up once before and I fucking blew it, literally. I blew my load less than 30 seconds after insertion! I was mortified.
I'd like to say it was a one time thing, no biggie, but this was a recurring problem for me. There have been some instances where I've managed to last long enough for my bottom to get off but for the most part, I shoot pretty quick. It's even worse if I'm the one bottoming; once something hits my prostate, it's over.
Maybe Drew was desperate or maybe I was more charming than I gave myself credit for, but somehow I had convinced him to give it another go with me. I really didn't want to mees it up this time. We got along really well in our chats; we were into the same kinks and fetishes. He was cute as hell and had a high tight ass; plus, he only lived a few minutes away from me. I wanted this to be a regular thing.
I parked my car in front of his house a little after 11; I did a final check in the rear view mirror. I don't know if I looked my best, but I certainly didn't look ugly. I slid my glasses off my face; my green eyes were one of my favorite features. I didn't want my glasses obstructing them. I ran my hand through my mess of curly brown hair. I generally let it run wild; even when I styled it, it always ended up crazy again.
I texted him I was there, and waited for a reply. It wasn't long before a message popped up on my screen, "Come around back, the gate's open; we can hang out in my hot tub."
I felt my mouth go dry. My anxiety was quickly building; I could hear my heart pounding in my ears and feel sweat forming on my palms. I made myself take a deep breathe in, 1-2-3-4, and out, 1-2-3-4. Better, not great but better.
I switched off my car and headed his way.
His backyard was beautifully done; tall palm trees, a nice deck, lots of seating, and lush plants, but the center piece was a large hot tub. Drew was already in it, leaning back and relaxing with the jets on, and the lights in the tub were set a nice soft red. It was quite the scene to walk in on.
I slowly approached him and cleared my throat, "Hey."
He lifted his head and peered at me, "Oh hey! Welcome! Come on in! I thought we could hang out and chat, maybe have a few drinks first."
I hadn't planned for this; I felt myself grab the back of my neck and massage it as I spoke, "Well, that sounds great, but I didn't bring my suit." Even as those words left my lips, I knew how naive and corny they sounded.
He let out a small chuckle, "Neither did I. No suits allowed here." He stood up, water dripping off of him with every move, slowly revealing his naked body. He was so sexy. Definitely more of a twink build; small, lean but he was toned as hell. I instantly felt my dick get hard.
"Fuck!" I grabbed my crotch and started repositioning things; my hard on was pressing right up against the zipper.
"Glad to see I have such an effect on you." Drew giggled, turned around and reached over the edge of the hot tub, showing off his unbelievably well toned bubble butt and puckered little hole. My dick lurched in anticipation, the friction was killing me, "I took the liberty of getting you one." He passed me an unopened bottle of something I assumed was alcoholic.
I twisted off the top and took a deep swig; I definitely needed some liquid courage, "Thanks! Let me just slip out of these then." I placed the bottle in a cup holder on the hot tub and began unbuttoning my shirt.
"Wait! Wait! I want to appreciate the full show. Last time it happened so quick I couldn't appreciate anything." That felt like a jab; I almost instantly felt my skin go red from embarrassment.
"Yeah....sorry....about that." I had taken the shirt off completely now and slid off my shoes. I like to think I had a pretty decent body; I certainly worked out enough for it.
Drew didn't say anything more on the subject; he just sat back down into the water and watched me undress, intently.
I can't think of a situation where I had been on display like this before. It was turning me on more than I would have ever thought; this practical stranger is sitting there watching me in one of my most vulnerable moments. What could he be thinking? What would he think when I pulled off my pants and my fully erect cock flopped out? I tried to avoid situations where it could be under close inspection. It was an area of insecurity for me; I don't know why. I've been told many times I had a nice cock; I've been told it was a good length and great thickness. But I still felt insecure about it.
I undid my jeans, and as I slipped my fingers around the top, I thought, "well here goes nothing." I pulled them down in as swift a motion as I could and stood there naked, fully hard and on display for his judgement. I couldn't tell what he was thinking by his expression; he simply let out a little moan and motioned to the seat opposite him. I was very turned on by this point, and I couldn't tell if his lack of reaction to my nudity was making me more or less aroused.
Once I was settled, I took another long swig from my bottle, "Soooo...how was your day?" Was that the best I could do? Wow, I'm pathetic.
He laughed and shook his head, "much better now that you're here." He leaned forward and scooted toward me; he grabbed my chin with his thumb and forefinger and pulled me in for a kiss.
I forgot how great a kisser he was. They started off soft and quick, just gentle pecks really; then slowly things started to heat up. Our tongues were dancing with each other and our hands were almost frantically exploring each other's body. He never directly touched my cock though; his arm or the back of his hand would brush up against the shaft. It was maddening. Meanwhile my hands kept gravitating to his ass and squeezing; those cheeks were firm as fuck!
He then did something truly astounding; he pulled away from me, panting the whole time he spoke," Damn, so much for hanging out first." He turned himself around and leaned forward again, so his ass was in the air and his puckered hole was on display, "Fuck me! Now!"
I gulp and stood up, "Yes sir." Due to our height differences his hole and my cock lined up almost perfectly in this position.
He spit on his hand and rubbed it on his hole; I did the same to my shaft. I grabbed the root of my dick and started to press against him, and just when I was beginning to push through, he turned his head, looked me dead in the eyes, and said, "Oh...and don't cum."
Great! Like I needed more pressure on me not to cum.
I pushed the rest of the way in as he gasped, "Fuck you took that like a champ."
"Well, I mean, I've had bigger, but don't worry ... you fill me up ... adequately." I felt my dick lurch as he said that. Fuck, why did that turn me on so much?
I cleared my throat and began to slowly pump into him, shifting directions, trying to find the perfect angle to set him over the edge, but it was like fucking a wall, I was getting very little response. It was driving me crazy and making me hot as hell! I picked up my pace, my cock sliding in him as deep as I could, with as much force as I could and as fast as my hips could go.
"Mmmm....there ya go baby!" He arched his back and started to thrust back at me with each stroke. Finally, a response.
"You like that? Huh? Fuck yeah." I was moving at a frantic pace now, giving it everything I had; I could feel the beads of sweat starting to slide down my face.
"Oh yeah, baby. That feels really ... good." That did not sound sincere at all, and the worst part was it pushed me over the edge. I could feel myself getting dangerously close. Fuck, I couldn't cum! Not yet! It had barely been a full minute of fucking. Shit! Not yet.
It took everything I had in me to not shoot; I was clenching every muscle I could. I had to finally stop and pull out, "fuck! I'm getting way too close!"
He let out a frustrated "ugh!" Then said, "Already? Jesus! Just like last time. You know none of this is really working for me. I'll be right back."
He climbed out of the hot tub and quickly shuffled into his bedroom, leaving a trail of water behind him. Although I didn't appreciate his comment before leaving, this break was actually a bit of a god send. I could take a minute to recuperate and regain my composure. Deep breath in, 1-2-3-4, deep breath out, 1-2-3-4; ok, not helping. My heart wouldn't stop racing and my dick was harder than ever.
Drew popped back out a few moments later with his hands behind his back, "I think you're going to like this surprise." He pulled out a bottle of lube in one hand, "we're gonna need this for sure." And in the other hand, he pulled out a huge dildo, at least 2, maybe 3 times my length and girth.
Fuck.
"You want me to fuck you with the dildo?"
"I want you and the dildo to DP me." He motioned for me to get out of the hot tub then lubed up the toy and his hole, "This is gonna feel so good."
I took the toy and the lube from him; it felt massive in my hand. And seeing it next to my cock made me feel so emasculated and ashamed, yet it also turned me the fuck on. What was wrong with me? I was never able to cum hands free before but I felt like I could have in that moment.
He leaned himself against the edge of the hot tub, arching his back, lining his ass up to my extremely eager cock, "Now baby, slide that big ok' thing in me first. It's gonna take me a minute to get used to something like that, and then you slip your....your dick in after that, ok?"
That couldn't have been coincidence; he was making fun of my size, right? And why did it make me want to fuck him that much more? "Sure thing." This was wild. I don't think I've ever been in a situation even remotely close to this one. I did as I was instructed, and although there was more resistance than with my cock, Drew still took the dildo with ease. I played with it a little, and watched him squirm and moan from this dick shaped silicone mound. Even when I was giving him everything I had, he didn't made sounds like that.
"Fuck baby! That feels so good. Ok. Now you." I lubed up my dick and discarded the bottle; I lined myself up with his ass. I didn't want to, but I couldn't help but compare myself to the dildo. It seemed huge to me, and drew just took it without much of any thought. There was a lot more push back on my cock this time; Drew was already very stuffed, I would have never thought he could take more, but he did it. "Yes baby! Fuck yes! Stretch me open! God, yes! Now I can feel every last centimeter of u, every ridge, fuck that feels so good."
Even I had to admit it felt good. The cold ridges of the dildo were rubbing the underside of my cock and the warm smoothness of Drew's hole was rubbing the top. God all fucking mighty! This was one of the strangest and best feelings I had known.
It took only a few quick pumps before my stomach dropped and that oh so familiar feeling starting rising back up. I was getting very close to orgasm. Shit.
"Oh god yes baby! Yes! This feels so fucking gooooood! Fuuuuck! Fuuuuuuck! Keep going! Oh god yes! And please! Pleeeease don't cum!"
Shit shit shit!
I clenched my fists and tensed every muscle I could; I heard myself let out a guttural moan. The more I tried to fight it, the closer and closer I could feel myself getting. I was right on the edge of cumming. I couldn't hold off much longer. Fuck fuck fuck!
"Fuck baby! Yes! Fuck me! Keep going! Fuck, you're so hard baby! God! This feels amazing! Please don't cum, baby! Not yet! Please baby!"
I started to involuntarily bite my lip and pound my fists on his firm ass cheeks; I had to find a way to hold back! Not like this! Not this fast!
"Yes baby! Hit me again! Spank me harder baby! Yes!"
I obliged. I tried to focus all of my attention in smacking his ass, but with each and every smack, he tightened his hole, bringing me even closer to the edge. I couldn't stop it. I finally shouted, "FUUUUUCK!!" And I unloaded. The first spurt almost hurt; it felt like I had a mountain of cum blast through my shaft! The second and third spurt had much less cum and the waves of pleasure were much more acute. The rest of the spurts that followed were barely anything. I nearly doubled over from the orgasm, "Fuck! Fuck! I'm so-"
"Don't cum yet baby! Don't cum! You have no idea how good this feels! Keep going! I don't want this to ever stop! Fuck!"
Had he not noticed I had already emptied my balls?
"Don't stop baby! Keep pumping!" He started pushing back on my cock, "and please don't cum yet."
Ok, he definitely hadn't realized I came. I decided it was best to play along! I was still hard enough, so I kept pumping, in and out, varying my speeds, as much as I could, but despite my wishes, my cock was growing soft.
"I. Am. Loving this!" Sweat had started pooling all over Drew's body; his hair was a matted, wet mess, "Baby! Grab my dick baby! I want to cum together!"
I reached over and wrapped my hand around his shaft, but just as I did, my cock slipped right out, and I could see my own cum leaking out with it. Shit! Shit shit! Now he's definitely gonna know!
"Keep going baby! I'm getting close! Jerk me off while you fuck me!" I did as I was told. I jerked him off, but fucking him was not gonna happen.
"Ummm..."
"Don't stop baby please! I'm so close now!" His dick was becoming more and more rigid. I decided the best I could do was fuck him with his dildo. I moved it in and out to simulate my typical pace, "Oh fuck! Yes baby! Oh god! Oh God! I'm cumming! I'm cumming!"
His entire body went solid and his skin gained a deep red flush right as his jizz leaked all over my fingers. It took a good ten seconds before his orgasm was through. I was completely flaccid by this point, but the sight of him cumming on me, with that giant dildo in his ass, was one of the hottest things I had ever witnessed, "Fuck! You are so sexy!"
"Thanks baby!" He reached behind himself and slowly pulled his dildo out, "now I need to go clean all your spunk out of me. Are you good to go another round or two after you cum typically?"
Did he know that whole time? I suppose I wasn't very subtle, "Ummmm...sometimes. I'm gonna need a little time."
"Ok. Well, relax in the hot tub. I'll clean myself up a bit and then maybe we do a round two."He slid open his door but before he fully closed it, he said, "Hopefully you last a little longer next time."
I guess he did know. That's embarrassing.
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