First time raw, planned or unplanned?

[Bibttmmiami]

The first time I took it raw was with a guy I had hooked up with a bunch of times before, mostly for oral, but we did anal with a condom before. 

Anyway he came over my place and we exchanged oral a couple of times making each other really hard, and he ate my ass which drives me crazy. After he ate my ass he got up between my legs and said he wanted to tease my ass with his cock a little bit. 

Now having hooked up with this guy quite a few times before I had no reason to think he'd try anything, but after "teasing" my tight ass for a few seconds he pushed forward and rammed his cock balls deep in my ass. I remember my eyes popping open when I realized what he had done and that his raw cock was in me, then I just moaned and told him to fuck me. The rest of the night we fucked bareback, and I even took him ass to mouth a couple of times and rode him too. 

The only thing that disappointed me was that he didn't buy breed me when he came, he gave me a facial instead. But I did suck his cock clean and I ate all the cum from my face as well. 

 

That was was my first time taking it raw, it wasn't planned, but it was hot. How about yours, planned or unplanned?

[Guest Lempriere]

Have you taken his load since then?  Very hot.  Would love to hear more.

[xxww]

My first time raw was planned definitely. If I was going to fuck for the first time I wanted to feel the real thing, fuck a condom. And boy was the first time heaven, the guy I met had a big dick and he knew how to use it. I was really tight and he had to work me open. When he finally slid all the way in, it was like no other feeling. The feeling of his mushroom head and thick shaft entering my hole raw, I knew no condom was the right choice. Then when he shot his load inside me it was amazing, that point on I knew I was a bareback bottom. 

Edited August 9, 2017 by xxww

[drscorpio]

My first time was raw because it was the early 80s, and raw was what everyone did. I guess that made it planned.

My first time raw after being a dedicated condom user for years was unplanned (well, I think he planned it). We were supposedly just doing oral. It started with me sucking his big, uncut cock. Then he pulled me into 69. Then he worked his way around to rimming me. This was my first time getting a really good rim job, so I didn't realize what he was up to. I was lying back with my legs spread up in the air while he went to town on my hole with his tongue. He quickly moved up on top of me and slid his bare cock into me. Even though he was big (a little over 8" by 6"), he had loosened me up enough that it slid with no pain at all. After a few wonderful strokes, I freaked out about the lack of a condom. He was a little frustrated, but he pulled out and put one on. The next time, we got together at his house, and he got me really poppered up. I begged for it bare, and he gave me my first load in 7 years. He bred me regularly until I moved away. 

[beanna]

my first time raw was when the guy took a condom out and I said you can get to fuck with that, its like taking a bath with your wellingtons on.

he only reqd.a few seconds to throw it away as I had wanked and sucked him brick hard

[joch]

My first time raw was my first time having sex and it was with an older guy who I used to babysit his grand daughter for. After the parents had picked up their child. He stripped me and had me lay down on his bed. He sucked my cock hard as he stroked his. Then he had me on all fours and lubed up my ass. When he put his dick at the entrance to my ass. the lube felt cool and I liked that feeling. then he pushed his prick in and it felt even better. When he started fucking me I found I enjoyed it immensely as he stroked my cock as he fucked. He came in my ass. When he finished I lay on my back and he sucked me off Swallowing my load. We got together quite regularly after that. Always bareback. As all my MM sex sessions have been.

[Gayasian]

My first time raw is with my current partner. He always have known I like it bare, then one day he decided to just fuck me raw. And from that day onward we always fuck raw, so I would say it's planned.

[Anonversecuck]

First time I ever had dick in my ass it was bare. I wouldn't have it any other way.

[FJLinNYC]

The other way around, the first time condom was planned. The sweet thing was after, he carefully took off the condom, etc., collapsed on top of me as we kissed, and his cock immediately sunk right back into my hole bare. We just kind of giggled, after all that fuss over the "condom"

[mblad99]

First time raw was unplanned.   Met a married guy on Craigslist with a condom in my pocket.   While he was sucking me, I lubed his ass with my finger.   After I was hard, he asked if I wanted to fuck him.  I said sure, he turned around, never asked for a condom.   I figured he was safe, so why not.   Just slid it in him, and came in his ass.   Fucked a lot of married guys since with no condom, they really seem to like it bare.

[analluv27]

My first time raw was unplanned, I hooked up with a cute chubby Latin guy while making out in the booth of the adult video store he had me try poppers and got so into it he wanted to fuck. Up until then I always did it covered but he didn't have any and I wanted him in me so bad I told him to fuck me. He ate my ass before plowing my ass deep and came in me. I was hooked since

[BlindRawFucker1]

The first time topping bare was unplanned.

A guy asked if I wanted to do it without a condom.  And, I did!  It was great!

 

The first time bottoming, it was planned.  I wanted to know if it felt just as good having a bare dick in my ass as it did having a warm ass wrapped around mine.  It did!

 

The rest is history.

[Btmcumslut416]

My first time wasn't planned at all. I was young with a much older top. He told me to relax and try to enjoy it while he worked his cock into me for the first time. Condoms didn't even come up as a topic of conversation. I did as he said and let him use my body however he wanted. Feeling his cock throbbing as he shot his cum into me was the best feeling of my life and got me hooked on it

[evilqueerpig]

My 1st time was in the Summer of 1977, before HIV/AIDS was even known, so of course it was planned as raw, as both top and bottom.  Even during the dark days, I decided it was better to keep the pleasure of skin to skin fucking and deal with the consequences of conversion, which is exactly what I've done.

[endowed]

My first time raw was right after I had come out.  It was not planned.  I was still a virgin (with gay sex).  I had been going to Club St John in San Jose, CA.  I had only been going to clubs for only a few weeks.  One Saturday night, a guy approached me and offered me a drink.  I don't drink, so he bought me a 7 up.  He then invited me to his house and told me that he still lives with his parents and that we would have to sneak into the house and be very quiet.

We got to his house and his older sister was still up and in the living room, so we couldn't go in the house.  Instead we went into his garage.  We got on the floor and started making out.  I got on top of him in missionary position.  He spread his legs and my dick was on his asshole.  He got a small tube of lube from his pants pocket and put some on his hole.  I thought that he was going to get a condom from his pocket too, but he just laid down again on his back and spread his legs open.

I got scared at first because I was afraid of AIDS.  I was thinking that I should do this without a condom, but I was so horny and just knew I had to stick my dick in there.  So, I got on top again and stuck the head of my dick in his hole.  He stopped me at that point.  He had never had a big dick in him before.  

The feeling his hole was giving me caused me to go in further.  I went halfway in and stopped while he gritted his teeth.  I could feel the cum boiling in my testicles and every nerve in my body was tingling.  I remained still for a while so that I didn't cum too soon.  I told him I'm going all the way in.  Before he could say anything, I went all the way in and held it there.  That felt so good that I groaned out loud.  He quickly put his hand over my mouth so that his sister would not hear us.  

I told him how good his ass felt on my dick and that I was going to start fucking him.  He said go ahead and start fucking but just be quiet.  I started with long, deep, and slow strokes in order to keep the cum from shooting out.  I could feel the cum building up right at the head of my dick, so I slowed down even more.  This only intensified it and I knew that I was going to cum real soon.  So I gave up trying to stop it.  So I just said Fuck it.  I started fucking him really hard.  I felt like I was all the way up in his stomach.  I decided to cum in him.  So it felt like a bolt of lightning hit me and I went all the way in and held it there and came inside his intestines.  He had to cover my mouth again.  I was going through convulsions.  I stayed inside him for forever, it seems, and just laid on top of him.  He had cum too but I did not notice until a few minutes later when I felt the slickness between his stomach and mine.

After about 20 minutes I finally pulled out of him and immediately I got scared again because I had fucked him, a stranger, with no condom.  I had just torn up his asshole and his ass juices probably went inside the hole of my dick, plus I was laying in the cum that he had shot on his stomach.  For a whole week after that, I was terrified of what I had done.  But I was also thinking that no matter what happens to me, that ass was good and I felt it was worth it.