What was your best Anal Experience?

Okay, writing that earlier post and a few PMs you sent got me very hot on the idea of ending my semi-retirement from ass fucking.

So I just chatted with an old buddy who said he'd happily scratch my itch later this afternoon. The last time I saw him, he fucked me in his fenced-in backyard. It's just a wee bit too cold for that today, so we'll have to get creative inside.

I will report back later...

Pirate_Guy said:

Okay, writing that earlier post and a few PMs you sent got me very hot on the idea of ending my semi-retirement from ass fucking.

So I just chatted with an old buddy who said he'd happily scratch my itch later this afternoon. The last time I saw him, he fucked me in his fenced-in backyard. It's just a wee bit too cold for that today, so we'll have to get creative inside.

I will report back later...

Click to expand...

Please do, and I hope this time is as hot as the last

Had 2... First was with a 5'3" tall, blonde M2F pre-op Transsexual w/ an 11 1/2", uncut cock.
Second was with an 18" Dick Rambone at the hands of an ex girlfriend. What can I say?... Small just doesn't do anything for me.

Pirate_Guy said:

Okay, writing that earlier post and a few PMs you sent got me very hot on the idea of ending my semi-retirement from ass fucking.

So I just chatted with an old buddy who said he'd happily scratch my itch later this afternoon. The last time I saw him, he fucked me in his fenced-in backyard. It's just a wee bit too cold for that today, so we'll have to get creative inside.

I will report back later...

Click to expand...

MMmmm.....looking forward to it...

Oh boy did I ever get my itch scratched today...

(Just to catch everybody up, I posted a quick recollection about the first time a guy did my ass -- see above in this thread -- and writing about it got me itchin' to get fucked again for the first time in a couple of years. So, I e-mailed a bi buddy and he said he'd be happy to help me out. Here's how it went this afternoon.)

I drove my Jeep through the latest "Storm of the Century" about 25 minutes to head over to his house. He has a nice home in the burbs, a great job and a mission in life to top masculine guys like me. I parked at the curb and trudged through the snow up to his door. I was a little nervous but also ready for a nice submissive afternoon. I have a very cool, but demanding job and a girlfriend who loves me to be in charge, so the idea of just giving up all of that every once in while has great appeal to me.

I hadn't seen him in a couple of years and he greeted me at the door with a big smile and tent pole jutting out inside his robe. I pulled the door shut behind me, reached under his robe and grabbed his cock. He proceeded to jump about a foot in the air because my hands were freezing from the walk up his drive. I said, "Shit, sorry...let me warm that up for you." Then I got down on my knees right in his foyer and took as much of his cock into my mouth as I could.

He doesn't have a long tent pole...maybe 6", but it's thick and has a slight upward curve and a perfect triangular head. Exactly the kind of cock that fits my ass. I reached up under his robe and cupped and squeezed his butt cheeks while I worked his cock as far as I could into my throat. I'm not big on the gagging thing but he really seemed to appreciate the effort. I looked up and he had his eyes closed and was just murmuring "Oh fuck...Oh fuck...Oh fuck...Oh fuck."

After a minute, he pulled me to my feet and led me through the house to his bedroom. He plopped down in a big chair in the corner and told to me to undress and that he wanted to watch me. He particularly enjoyed the fact that I wasn't wearing underwear and my hard cock popped out of my jeans when I slid them down. I stood naked in front of him and stroked it for a few seconds. He was kind enough to compliment me on my 48-year-old body. I'm lousy about working out, but I still look pretty good for an old dude.

BTW, he's a good-looking guy. Just hit 40. Married and divorced 10 years ago. No kids. Not tall, but handsome face and a compact sort of gymnast body. Dark skinned and also does the fake tanning thing (I do too). Hairy, but not a candidate for the primate cage at the zoo. Nice smile, smart and funny. I like him.

I walked over to him and told him my cock was a little cold too. He kissed my cock and licked it but immediately reached between my legs and started fingering my hole. That made me shudder a little because it felt fantastic and I suddenly remembered he was going to put his fat hard cock in there in a bit.

We moved over to his bed and both crawled under the covers together, both kind of shivering from being cold and excited. We made out...kissing and exploring each other's bodies. I slid all the way down under the covers and got his cock back in my mouth again. I tickled his balls with my fingertips and ran my nails lightly up and down his taint going back and forth between his balls and his ass. I know it feels good on me and I guessed (correctly) he'd like it too.

He was moaning a lot but then said clearly, "Lick my ass." So I did...but not right away. I worked down slowly, sucking his balls and then just using the tip of my tongue down his taint (which was shaved, thankfully) to his anus. I spread his ass cheeks and just barely flicked his asshole with my tongue for a long time.

He was, as you might imagine, going crazy. I caught him offguard when I stuck my tongue into his asshole as far as I could and gave it several big swirls. His ass was nice and wet with my saliva and I happily ate away at it for a while. I started to slip the tip of my finger in along with my tongue and it slid right in. He was going wild from the ass play and I started to think it might be fun to fuck him too.

I guess he read my mind because he pulled away from me and said, "I need to fuck that ass of yours now." I sucked his cock quickly one more time before emerging from under the covers up to face him. I looked him in the eyes, swallowed hard, and took the submissive plunge: "I'll do whatever you want me to. Treat me like your little fuck toy this afternoon. Just please fuck my ass."

He smiled and rolled me over on my back and grabbed a few pillows and shoved them under my ass. He reached over and grabbed a condom and lube from his bedside drawer. He poured a bunch of lube over my cock and into his hand and proceeded to grease up my cock and rub it down between my ass cheeks. Every time his fingers went across my asshole I breathed harder. Without warning he slid a finger all the way into me. Ohhhh...felt fucking great. Then a second finger. He found my prostate and started probing it. Fuck, fuck, fuck! Here it comes, I thought.

But instead of continuing to finger fuck me, he climbed up and straddled my chest and put his cock inches from my lips. I tried to reach up to guide it into my mouth but he grabbed my wrists and pinned them back behind my head. I barely opened my mouth and he pushed his cock in hard and started thoroughly face-fucking me. Spit was flying everywhere I was gagging and trying to suck all at once. He rubbed his wet cock all over my face and "slapped" my cheek with it a few times. "You like this don't you, cocksucker?" I quietly said, "Yes.

He reached around behind him and gave my cock a few quick pumps and then slid a finger back into my ass. I really wanted his dick instead and told him so. He got down between my legs and put two fingers in me and pulled upwards hard enough to almost lift me off the pillows. My hole was well stretched. He grabbed the condom and rolled it on and put another gob of lube on the tip of his cock and said, "What do you want me to do?"

"Fuck me please."

He put the tip of his cock up against my ass and began to slowly work it around my hole and tease me. He totally owned me at that point and he knew it.

"What do you want?" He's looking down into my eyes with my ankles up over his shoulders and his cock poised right at the point of going into me.

"I want you to fuck me with that big thick cock...please." I was close to begging.

He reached down again and put his thumb all the way inside of me and wiggled it. "Are you sure?"

"Yes...fuck me right now."

And he did. He slid his cock into me in pretty much one motion and held it there, completely inside me, for probably 30 seconds. It felt like a a beer can in there but that feeling of being completely full is indescribable.

Then he started to fuck me slowly, rotating his hips around and grinding his pelvis against my ass cheeks. He lowered his chest down to mine and kissed me...deep...while his cock pushed even farther up into me.

Then he pulled out and sat up and sort of adjusted the pillows under my ass, raising me higher, and positioned his cock at my hole again and whispered, "You're going to be my little bitch now." I just said "Yes, please, yes."

He started fucking me in earnest. Fucking me for himself, not for my pleasure. And it felt amazing. I looked down and watched his dick go in and out of me and saw that my cock was dribbling precum all over my stomach. I wasn't very hard but I felt like I could cum at any second because he was smashing against my prostate with every stroke.

"Tell me how much you love this," he said.

"I love it...don't stop," I said.

"Tell me you'll come here and be my personal cocksucker whenever I want."

"I will...any time...just call."

"This is my ass now isn't it?"

"Fuck yes, it's all yours...you own it."

"Next time I might tie you up and fuck you all night...do you want that?"

"God yes!"

"I might even invite a couple more buddies over and let them fuck you too..."

That did it. Between having my ass pounded and the incredibly hot talk, I just started shooting cum all over both of us. I'd only done this once before when being fucked so it kind of surprised me. He felt it and reached down and stroked me hard until I finished. Suddenly, my entire body was overstimulated and I tried to pull away from his cock. But he wasn't done. He grabbed my legs and held and kept fucking me hard even though I was sort of writhing around from having way too much pleasure at one time.

He finally started going over the edge and pulled out, ripped the condom off and slid up next to me, furiously jerking his dick over my face and chest. The first spurt hit me in the chin and neck, but plenty of it got into my open mouth. A little hot salty treat on a cold afternoon. I can still kind of taste it hours later.

We pretty much collapsed together for a few minutes and talked about how fucking great it had been. He asked me if I wanted a shower but I turned it down, partly because I sort of liked the idea of having the dried cum all over my chest and neck the rest of the day.

We got dressed and he was walking me to the door. I asked him if he was serious about wanting to tie me up or have other guys come over and use me. He said, "Hell yes. Your ass is mine now. So's your mouth."

With that, I hopped back in my cold car and headed home to write this story and think about having three or four or five guys do whatever they want with me the next time I need to scratch the itch.

Wow Pirate_Guy,

You are my new hero

Thank you sir...sitting is not easy today but it was worth it.

Mmmmm.......Fuck, that was totally hot dude.

That was a hot story ....

Hot story. That is what I want.

I can't compete, but I have two separate occasions...

One involved the handle of an old Kirby vacuum cleaner. When I lived home and was just out of high school, I had this anal fixation that was just crazy. It started with a few thin items, and eventually worked up to a few things of thicker volume...but not the crazy ass-ripping things I've seen some people get into, fists, etc....just something that satisfied a craving....

Anyway, we had this old Kirby vacuum, and my mother asked me to run the vacuum for her, she had some other stuff that needed to be done, and her and my father had to leave for an appointment, so I said no problem. I started vacuuming the living room, and worked my way into the bedrooms, and as I'm using this thing, I notice that the handle is almost cock shaped, bent, kind of thick in the middle, and has a hooked end shaped a little like a cock head...I figures WTF, let's give it a shot! So after I finished with my chore, I pulled it into my bedroom, and grabbed my lube. Got my ass a little lubed up and started working on the handle. I put it up to the entrance to my ass and slowly worked into it...It was rolling on the wheels, so I pulled it to the other side of my bed, and lodged it up against my dresser, the distance between my bed and the dresser were perfect, and I started working the handle up my ass again. Once in, I noticed that the end of the handle, was hooked in such a way that it hit my prostate PERFECTLY, so as I rode this thing, I could feel a mounting orgasm building, and next thing I knew I was shooting a huge wad on my bed without even touching my cock! AND it was an intense cum!!! Well, that handle got ridden every time I had a craving and it never failed to satisfy me! (but never quite as intense as the first shot with it, maybe the element of surprise had something to do with it)

The second experience was with a friend that I used to suck off a lot. Not the guy I've mentioned before that I had the summer of three ways with him and a girl that lived in our neighborhood that summer, another guy that I occasionally got together with for a little suck fest. He had a much bigger cock than my friend, a little longer (maybe about 7+ inches) and a bit thicker. I figured I could take him, and after some persuading, I finally talked him into fucking me. I started off by sucking him until he was good and hard, while lubing my ass. Wen I had him at full length and girth, I started slathering KY on his cock, and got him nice and lubed. I bent over and told him to take his time putting it in my ass, so I could get used to how big it was. He was a little cautious, but soon sliding it in and out and I was loving it! After a little I said "let me roll over onto my back" so I rolled, and he re-entered me. The angle put a nice friction on my prostate and as he started stroking my cock, I could feel my orgasm about ready to burst, him seeing me about ready to cum, started getting to the point of no return himself, and was trying his best to hold off until I was ready, he let go as my cock let go, and I milked the cum out of his cock deep into my ass and my spurt hit him in the face. He collapsed on me and we ended up being very sticky. I could feel his cock getting a little soft so I started squeezing my ass together, and he got hard again! (oh to be 18-19 again!!!) with this, he started sliding in and out again and kept fucking me until we were just too exhausted to continue. We took a break, rinsed off, and finished the afternoon with a 69...

Those were two "sessions" that I'll never forget!!!

Pitching and catching

I’ve had two really excellent anal experiences; one ‘pitching’ and one ‘catching.’

Catching: The first time I let a guy fuck me was really good. He’d seduced me (I was ready and willing) over the period of several hours. We had drinks, we talked and laughed, eventually we got in bed so he could give me a nude massage. Of course within minutes I was sucking him. We sucked each other in every position, and at one point he was laying on top of me. I was totally relaxed, 100% immersed in the raw passion of the moment. I spread my legs and he got the hint. His cock probed my ass, gently pressing and slowly entering my virgin ass. I wrapped my legs around him, and met his gentle thrusts by rocking my hips forward to meet him. It didn’t hurt, instead it was a nice feeling of being filled and probed. As he reached full penetration we moved and rocked and humped together. I kissed him as we fucked. I loved giving myself fully to a man for the first time. He really knew what he was doing. He kept changing pace, sometimes teasing by nearly pulling out, just probing my sphincter and prostrate. Sometimes he would drive deep and slow, sometimes faster while he grabbed my ass hard. I was rock hard, and could feel the pre-cum dribbling down my shaft. I knew I was going to cum hard and soon.
I tried to match his movements, but he was fully in control. I blew in his ear as he fucked me, and I hugged him hard, pulling him close. He was getting sweaty and breathing hard. Blowing in his ear seemed to really get him off, and soon he tensed, drove hard and deep into me and began to cum. He was up on his knees, arching his back and spasmed into my ass while he groaned loudly. This drove me over the top, and I began to cum. I spurted hot gobs of cum all over my stomach and chest. At the same time I could feel his warm cum filling me. After 8 or 10 hard thrusts he started to calm down. He layed down on me, catching his breath while I kissed his cheek and nibbled his ear lobe. My cum was smeared between both of us, joining us together like sticky glue. The smell of cum was thick in the room.
After he had calmed he got up and cleaned himself, and brought a cloth to clean the cum spots on the sheets. Loads of cum had run out of my ass. We kissed some more, slowly, deeply and sensually. We feel asleep in each other’s arms, fully spent and satisfied.

That was about my 10th experience of sex with a man, and it was a breakthrough for me. I’d finally done everything two men can do together, (letting him fuck me, and kissing him) and I loved it. From that day forward I knew I was 100% Bisexual. I could be fully sexual with either men or women, and enjoy it without restraints.

Six months later I was traveling in Sydney. When I arrived I didn’t know it was a very gay town, but I figured that out pretty quickly. While I was there I enjoyed sex with men and women equally.

Pitching: Once I was waiting for a bus in Sydney when a cute guy started up a conversation. He was obviously trying to pick me up, and had sex on his mind. I had no place important to go, and figured I might as well get a blow job while I could, so we went back to his place. He was older and smaller than me, maybe 30 years old to my 26. He wasn’t more than 5 foot 6, thin and fit…my favorite man date type.
He had porn mags on the coffee table, which I thumbed through while we chatted and had some wine. We discussed which pictures and models were hottest. We finished our wine and went into his bedroom, where I dropped my pants and sat on the edge of the bed. He kneeled in front of me, took my hard cock in his hands and asked ‘Where did you get this monster?’ He started to lick and suck. I placed a hand on his head, laid back and enjoyed his expert, experienced technique. As we both got more into it, we undressed and got in bed together. I wasn’t participating or reciprocating, I was just enjoying the blow job. He was obviously enjoying what he was doing, and I was too. I was on my back, he was between my legs. After a while I decided I wanted to fuck him, so we moved around, he was face down, I was on top. I entered him and loved his small tight ass as I worked slowly deeper into him. He moaned like he was enjoying it as we went at it hard and sweaty. I was pumping him hard and deep, kissing his neck and ears as I fucked him. I wanted more, so I rolled him over so we could fuck face to face. We kissed as we fucked, and I ran my hands down to his tight ass. For some reason I’d never done that before…fucking a guy face to face. His ass was so tight it was a surprise and a major turn on for me. It was really small and tight. I grabbed it hard, squeezing his buns together as my hard cock drove into him. So tight! I was blown away, and came right away.
After I caught my breath I played with his cock, and gave it a quick kiss. I thought about sticking around, sucking him and maybe letting him fuck me. But I was feeling satisfied and selfish, so I just got dressed and left.

Best man to man fuck ever. And again I confirmed that gay sex was at least as good as straight sex.

Daaaaaaaaaaaaaaamn! I had to quit reading this story before the wife catches me jackin'. GOD, I'm horny.

It was back 25 years ago ... back when going bareback was a fairly safe thing to do. It was a 3 hour afternoon get together at a local hotel room with a doctor I'd struck up a friendship with that turned into a friends with benefit relationship. Anyway, after we had both enjoyed giving/receiving and oral sex with each other, including some awesome cum swallowing, we relaxed and recovered for a while before he got some lube and told me to raise my legs up. He lubed his cock and my anal entrance, and then easily slid his once again rock hard pulsating penis inside of me.

The position was identical to this:

[Material prohibited per our forum guidelines.]

It was by far one of the most awesome experiences I ever had, and to watch his face and feel his cock pounding inside of me before finally erupting in a massive cum spewing orgasm was all the more rewarding!!!

So hot...so need that

I have two that I can't clearly decide which was the best.

1. My very first time having anal. I was 16, my cousin had just turned 16 as well. We'd been playing for years, licking and sucking each other's cocks, rubbing them together, etc, but on this particular night we were staying at my grandparents' place, out in their motorhome, alone. We did frot for awhile and then he asked if I'd ever had anal. Of course I hadn't, we were both still virgins, duh. I told him I was willing to try if he could find some lube. Long story short, he found some vaseline in the bathroom, and lubed us both up, then pressed into me.

At first it was painful and uncomfortable, but as I got used to it something remarkable happened--it began to feel *incredible*, and I was dripping precum. Eventually he came inside me, and I fingered my ass and jacked off to completion. It was simply an extraordinary experience.

2. I had been dating this amazingly sexy older woman (she was 43 and I was 27, but she looked maybe 32-33), who was open to just about anything. We had the most mind blowing sex I've ever had, for about a year. About 6 months into it, I told her about the experience above, and she was entranced. She told me she'd always wondered what it would be like to fuck someone with a cock, and in time we agreed to get a strap on.

So she bought this strap on that was about as girthy as the tube from a roll of toilet paper, and I came over, not knowing this. We started making out, and after awhile she started grinding her hips against mine, which was when I felt it--she was already wearing it. So we went to the bedroom, and she worked her fingers into me, lubing me like crazy for a good 20 minutes or so, stroking my prostate and such. So anyway, apparently this strapon was special--it was also a vibrator, but more than that it had, inside the underwear bit, a little wiggly jelly thing that massaged her from her clit down into her labial folds. Nice.

Anyway, she finally got ready, and I could hear her behind me, panting with excitement as she turned on the vibe. She put her cock against my asshole and began to push. I pushed back a little as she slowly passed the entryway. I felt the first 3 or 4 inches slip in, and then it happened.

She burst into orgasm, digging her nails into my ass (she drew blood, I later realized!), and collapsed, gasping on my back for about a minute. I asked her if she was OK, and she replied, her voice trembling, "fucking great." And then she got up and started pumping my ass again. For the next two hours she pumped me, succumbing to orgasm after orgasm. She made me cum twice without even touching my cock, and when she decided she couldn't deal with another orgasm she fingered my prostate for awhile and jacked me off one more time, swallowing the final load.

Just mind blowing. I think the reason I can't decide which was more intense was simply that the first time holds a special place

BentSecrets said:

I have two that I can't clearly decide which was the best.

1. My very first time having anal. I was 16, my cousin had just turned 16 as well. We'd been playing for years, licking and sucking each other's cocks, rubbing them together, etc, but on this particular night we were staying at my grandparents' place, out in their motorhome, alone. We did frot for awhile and then he asked if I'd ever had anal. Of course I hadn't, we were both still virgins, duh. I told him I was willing to try if he could find some lube. Long story short, he found some vaseline in the bathroom, and lubed us both up, then pressed into me.

At first it was painful and uncomfortable, but as I got used to it something remarkable happened--it began to feel *incredible*, and I was dripping precum. Eventually he came inside me, and I fingered my ass and jacked off to completion. It was simply an extraordinary experience.

2. I had been dating this amazingly sexy older woman (she was 43 and I was 27, but she looked maybe 32-33), who was open to just about anything. We had the most mind blowing sex I've ever had, for about a year. About 6 months into it, I told her about the experience above, and she was entranced. She told me she'd always wondered what it would be like to fuck someone with a cock, and in time we agreed to get a strap on.

So she bought this strap on that was about as girthy as the tube from a roll of toilet paper, and I came over, not knowing this. We started making out, and after awhile she started grinding her hips against mine, which was when I felt it--she was already wearing it. So we went to the bedroom, and she worked her fingers into me, lubing me like crazy for a good 20 minutes or so, stroking my prostate and such. So anyway, apparently this strapon was special--it was also a vibrator, but more than that it had, inside the underwear bit, a little wiggly jelly thing that massaged her from her clit down into her labial folds. Nice.

Anyway, she finally got ready, and I could hear her behind me, panting with excitement as she turned on the vibe. She put her cock against my asshole and began to push. I pushed back a little as she slowly passed the entryway. I felt the first 3 or 4 inches slip in, and then it happened.

She burst into orgasm, digging her nails into my ass (she drew blood, I later realized!), and collapsed, gasping on my back for about a minute. I asked her if she was OK, and she replied, her voice trembling, "fucking great." And then she got up and started pumping my ass again. For the next two hours she pumped me, succumbing to orgasm after orgasm. She made me cum twice without even touching my cock, and when she decided she couldn't deal with another orgasm she fingered my prostate for awhile and jacked me off one more time, swallowing the final load.

Just mind blowing. I think the reason I can't decide which was more intense was simply that the first time holds a special place

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AMAZING! Do you still have any anal fun?

I love the times it just feels right straight away. Inside you just right, catching your rhythm straight away. Those are the best times. Had one time when I hadn't had cock for a few months and after he had worked my arse with his tongue and lubbed me up I was ready. I slid down on it and rode it for all I was worth making sure that my arse was ready and then I just let him change the positions at will as he took control. Fucking lush it was too.

hi

I was around 16 or so i think.Iwas stoned with a some large drags of grass.I actually invited him to do sodomy on me voluntary submission.That was the first and the best ever.no lube and no power to resist.pain for 2-3 days.Now we are regulars.






















online youtube to mp3 converter, limewire

(extrapolated from a previous thread)

Not really a guy who enjoys much anal but the most profound was when I had an older/younger thing going for a while a few years ago.
I was 21 at the time and the gf was away for work. Was webcamming with a couple not far from me (through a swinger/singles site) and after giving me a bit of a show asked me if I wanted to come join. Gave me their address, was there in half an hour.

The guy opens the door naked, big (bigger than mine) throbbing cock pointing at me. He cheerfully leads me to the bedroom where his gf was where he left her. I only had two pieces of clothing on and they were off pretty quickly. Started out by going down on him, then she went down on me while he continued to fuck her. It was only then i asked how old they were, she was 29, he was 42.

They put a rubber on me and I started fucking her and then he came up behind me and I felt him put some lube around my ass. He asked if I had ever had cock inside me and I was a little nervous and said "not in quite a while". He put the head up against my ass and started to push in. I don't really know how after years of not having anything up there, but it wasn't as difficult as I thought it would be. He went in slow and steady and I didn't feel any pain and started fucking me. He was pretty much just fucking her through me and I was lost in ecstasy, my cock sliding in and out of a wet pussy and a rather thick cock pushing on my prostate. I kinda was lost in a sex haze after this but she recalls me exploding brilliantly inside her not long after he came.

best anal experience definitely involved a hunk of a man and my vibrator. He fucked my pussy while my vibrator was shoved up my ass...incredible! He could feel the vibrations the entire time, and i could barely move

An old girlfriend and would break out the baby oil and just have at it some nights. One night we laid all of our sex toys out and had some real fun. At one point, I had my cock in her pussy, a vibrator in her ass and a butt plug in my ass. It was beyond hot.I actually managed to stay hard for two rounds. The cock rings helped.

My best anal experinece is my very first anal experience when I lubed up my curved vibrator and inserted it deep in my ass. The sensations were unbeievable. When I turned it on high and got on my knees to ride it I came so hard. I feel my juices running out of my pussy now just thinking about it!!!

just realized i posted on the GLBT of which i don't fall into any of those categories oops

naughty_shygirl said:

just realized i posted on the GLBT of which i don't fall into any of those categories oops

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no worries! still hot.