do that with me

TravelinBi - that is an AMAZING story.

Although I can't imagine loosing my cherry with just spit it sounds like you were lucky enough to have a man who knew what he was doing...

My First Time was a Double
 

I first had man sex at the glory holes. I used the glory holes for many years to get blown. I'd always make sure the guy blowing me had a hard on. I'd suck cock but it was always me that came. I got some ass fucking thru the holes from time to time but mostly just blow jobs. I experimented with protected anal a bit at the holes and even shared my booth a few times with a dudes that fucked me with a rubber. In time my appetites increased to the point where I finally let a cock cum in my mouth. After enjoying many loads in my mouth, I came the conclusion that anal would feel better raw and decided it was time to take it to the next level. I had a trip to Amsterdam coming up and I decided to take it raw for the first time on the trip.
The night before I left turned out to be a very warm night in San Francisco, which is quite rare. I decide to take advantage and go to the park and do some out door cruising. I cleaned my ass, put on a pair of shorts, and headed out.
I parked and headed up the hill to the main cruising area. Just before I got there I took the shorts off and tied them to my ankle. It was rare that it was this warm at night and the place was packed with cruisers. I got into the first of several concealed areas where the action takes place. I found a nude man with a raging hard on standing and another kneeling behind him riming his ass. He cock was hard and exposed so I bent over and sucked him. I do pretty good with my throat and tongue. He started pumping his penis deep in my throat. The pumping prevented the guy now facing me on his knees from riming so he moved over to my exposed butt hole. I'd been rimed only once before and it is fabulous. I continued to work on the cock in my mouth as I enjoyed the rim job and a crowd gathered to watch the action.
The guy in mouth reach back kinda cut off my rim job and fingered my hole to signal he want to fuck. I turned around and for the first time a penis entered my man cunt raw and bareback. After the rim job I was open and ready for a pounding. He went right to it with strong quick strokes. I watched the rim guy kneeling in front of me beat his meat as I took it up the ass in full force. One of the crowd watching us pushed his cock into my face and gladly sucked him for a bit but the action behind me was too thrilling to give him proper head. It took several minutes and a reentry before the cock in my ass came to a stop buried balls deep. He jerked around a few times inside me a pulled free. I was pretty sure he came but before I could check for sure I felt hands on my hips. It was rim guy. He tasted and tongue fucked me before he stood up and penetrated me with his thick cock. I was thrilled to continue the anal pleasure as he slapped against me pounding my hole. As he fucked me, and another penis was presented in front on me and a I took him into my mouth and sucked him. I was aware of many men around us including another guy getting ass fucked and at least one other blow job in progress with in a few yards of me. These two guys fucked at me from both ends and I loved it. My blow job guy reached in and took my cock in his hand and felt my hardness pulling his dick from my hungry mouth. He turned around and pushed back until my cock penetrated his ass. The force of the dude pounding inside me we transferred to the ass I was now fucking. I had never been sandwiched and I was loving it. I stroked the cock of the guy I was fucking keeping him hard as I fuck his hole. From behind me, a heard a whisper "you have a sloppy hole now" as the guy inside me came to a stop. When he pulled out, I slid a finger inside myself and pulled it up and tasted the cum. I wasn't the only one to taste it as my backdoor man cleaned his cum out of my ass. My dick was still inside the fellow in front of me but I wasn't able to pump. He began bouncing back into me with a very pleasing rhythm and I soon came inside him as my ass was being tongued.
That's the story of how my ass took its first and 2nd load. It would take many more on my trip to Amsterdam.

Wanted his load
 

Met a guy on a phone sex dating line that lived 5 miles from me.We met and hit it off personally and sexually for over 5 years.Started out naked in bed making out and sucking each other off but I wanted his cock inside me from day one.He was really hung 81/2 inches and he tried to penetrate me a couple of times but he was too big and I was too tight.
One day he brought over some poppers and weed and after we smoked a joint we started to make out and he rolled me on my stomach I took a hit from the bottle and he slid his cock deep inside me.Didn't take long for him to cum and I knew he did as soon as he bit my shoulder and started to moan.From then on most of our hookups ended with him filling my ass with cum

Dugout
 

My first time getting fucked bareback was when I was 13. I was just walking around outside when I went into one of the baseball dugouts. As soon as I was inside, the way out was blocked by 2 senior football players. There was no way for me to fight or escape and no one was around.
They said OK faggot (even though I wasn't out I was giving blowjobs to the younger brother of one of the players) we are gonna make you our bitch. They both dropped their pants and the big one closest to me ordered me to suck it which I did. He got harder and bigger than his brother when I sucked him. I thought OK a couple blowjobs wont be horrible and I could swear they made me do it. The big one had other ideas. He told me to drop my pants and turn around.
I had never been fucked before and had never even known about anal but when I turned around and he shoved me forward, he lined his cock up with my hole and rammed it in to his pubes. I stifled a yelp because the pain was intense especially with the only lube being my spit. He pumped me fast for like a minute and then he stopped with his cock deep inside. I could feel it pulsing and it felt strange inside my ass. At first I was miserable but when he stopped (I later learned that was when he came) I was loving it.
The other player who had been watching this action and stroking said it was his turn. The other guy pulled out and he pushed his way in. He was longer and fatter than the other dude and he was taking his time. I actually started to push back to get him in all the way. He really got into it and he lasted a few minutes before he stiffened and groaned.
When he pulled out they got dressed and left. I sat down on the bench with my pants still around my ankles. I was reeling from the intensity of the sensation plus sore and a little weak in the knees. My cock was leaking precum like crazy. I realized at that point that I would have to do that again and again and ......

first time
 

I stopped pnp years ago but do once in a while. I did some and was fantasizing about some local boys and started putting ads on cl and some other sites trying to meet up with some horny tops.
I had tried this many times and was finally surprised to get a response. Some local twinks sent me an email and a cam of them partying in a hotel room. All I could see where their hot bodies and hard ons with music playing in the background. They asked if i partied and wanted to bottom for them. They were all super hot and I told them I would be interested. i couldn't believe it when they sent the hotel and room number and their phone. I called to make sure it wasn't just a joke and they were all screaming and having a good old time and they told me to come to the room and take it from there. I got the courage to go and when i got to the room one opened the door and the other two were laying n the bed naked stroking major hard ons. i walked in and the first one gave me a big gagger and we hung out for a minute then I went and got in the shower. When I got out the music was blaring and he offered another gagger. As soon as I took it he climbed on top with his lubed cock and slid it in. They all started laughing and yelling that they were all going to give it to me in the ass and no condoms. They were all going wild and he finally blasted his load in me and another started pounding me while the others were shoving their dicks in my mouth.They took turns and blasted me full and that was just the beginning. I didn't leave the hotel room until the next day and got cummed in more times than I could tell. It was one of my best sex experiences of all time and i could write a book on all the things we did.I think they made a video and would love to get my hands on it. Like Nike said when the opportunity exist go for it.

Hi
Billy here the first time a boy/guy fucked me it felt real good especially when he poped my cherry an loads after loads of cum came out deep inn side of me an he planted hiseeds deep in me to where they would not ever come back out..
we did it raw an with out any lube except for spit which he spit in my ass (boi pussy) an shove every in of it all the way up in me ar1 time fucked me hard an deep
Billy
(email address deleted)

Nothing but spit as lube for your first time? Ouch!

I think we used a full jar of Vaseline and I still wanted more!

Fucked n Bred in park by 2 strangers
 

As a teen in late 70's, I was a tall thin runner. At 16, I was 5-11 but only 110 lbs. I'd heard about a cruisy park where "those guys" would hang out. Running gave me the freedom and the excuse to explore the trails so early one summer day I set out on a long training run wearing short 1980's style nylon tricot running shorts, shades, and shoes. As I reached the back part of the park, I saw 2 guys off the trail naked n stroking. I approached quietly and watched. One was older with grey hair who looked about 60. The other had brown hair and looked to be around 30. I pulled out my 6" cock to stroke as I watched them take turns on each other. When they noticed me about 20 yards away, they waived me closer. As I joined them the older guy dropped to his knees and started sucking me as he pulled down my shorts while the other guy got behind me and helped me step out. We all stood naked and stroking ourselves then each other. Younger guy dropped to his knees to blow me some when older guy moved in behind me and started dry humping my ass with his medium sized cock. He embraced me from behind and started nuzzling my neck and working my nipples. I moaned in satisfaction so he kept going. I pulled out of younger mans mouth to avoid coming and bent forward to suck his 8" cock. Older man took this as a sign to drop down and start rimming my smooth twink hole. Before long I was grinding my ass against his face and he soon worked a finger into me. More groaning on my part was taken as a sign to go for it so he stood and worked his cock head into my virgin hole. Lubed only with sweat and saliva, he worked himself all of the way in as I continued to suck away on the younger guy. It didn't take long for me to start cumming from all of the sensations. As I did, my ass clamped down on the old mans cock which sent him over the edge. I could feel him shooting in side me as I sucked hard on the big cock in my mouth. After the old man had finished emptying his load into me he pulled out and told the young guy to take his turn. They spun me around and younger guy worked his big cock into my ass as old man went ass to mouth on me. As I sucked my juices off The old man, the younger guy slammed into me and held my hips tight against his groin. He held tight as he blasted his load into me.

When we all caught our breath, we disengaged and started to talk. They were amazed at my being only 16 and being down to fuck. They filled me in on the cruising "rules" for that park as I learned that they both played there often and had hooked up with each other before but weren't a couple. The younger guy was ready to go again first so he bent me over a tree strump and planted as second load in me then the old man slid in for his encore. I finished my run with four loads of cum in me and soon found myself back in the woods on another run.

Damn hot story fulcrum!

Was that the first time you had ever been fucked or just the first time someone came inside you?

It was my first time getting bred but a friend and i had messed around when we were younger. I learned I like the feel of his little dicklet in my ass tho we were too young to cum. This was my first time getting fucked by men .... But not my last. :)

Although I have not done bareback for many years for safety reasons, I am very glad that when we started messing around in the pre-AIDS days I got to experience it.

I am sure it is more psychological than physical but there was something about knowing that your cum was inside your buddy or his cum inside me.

The first time that I took a load up my ass was nowhere near the first time that I was fucked but I know the feeling of that need well. Once you have done it the need to be bred raw will always be there.

First time raw
 

I posted my story about the first time that I took it raw, but I wanted to say something about the way it made me feel.
I had been getting fucked for probably five years and had completely stopped having sex with girls. As great as all sex was, with girls or guys, I found that I loved the feeling of a guy's cock in my ass so much that it had become something that was the focus of my sexual desires. At the same time, it was starting to become not enough and I craved more. It was so fantastic, but using condoms was starting to feel like I didn't ACTUALLY have his cock in me while he wore a rubber.
I had been going steady with a great guy,(still my partner now five years latter) for several months when I asked him about going bareback. We got tested and, after the results came back, he came over for the night and our first, for both of us, REAL sex!
I'm not going to talk about what we did in this reply. I want to talk about how it made me feel. It's always felt fantastic and, to tell the truth, I couldn't really physically feel the difference without the condom, at least until he came.
The difference was mostly psychological. Until he was all the way in my conscience thought was focused on getting him past my ring and all the way in. Once there and able to think again, (he is somewhat bigger than average) it really hit me as to what we were doing! I had an ACTUAL real live cock up my insides, no condom between us, my wet inside tissue actually being exposed to his pre-come and the knowledge that I was going to have his thick, white strings of cum actually up inside me was such an intimate, Hot and kinky feeling that I came the first time as soon as he started thrusting.
When he was getting ready to cum I told him to stick it in me as deep as he could get when he started to shoot! I needed to feel like his seed was as close to the core of my being as possible! When he started pumping his load up my boy cunt I was in a sexual frenzy to the point of craziness. I remember babbling something about breeding me and knocking me up! After he came he stayed in me and grabbed my cock and jacked me until I came again. I came so hard that my vision dimmed, I got this roar in my ears and almost passed out!
This was what I had been wanting and needing! I felt so complete, like I wasn't a wanna be anymore and really gay. I felt so good and like a real Faggot at last who gets fucked for real! I also felt something like pride. I felt like running out of the house and down the street yelling about what I had just done. It wasn't an exhibitionist type thing, more like it was too good and exciting to not share and I wanted to tell someone! We haven't used condoms since.
I could be completely fucked out and not even horny and I would stile love a naked cock in my ass or mouth!

What a great experience! Getting fucked seems to just get more wonderful every time you do it but there is something really special the first time. It felt soooo good but it was more than that. I felt such relief from finally getting what I needed and such exhilaration and pride at finally being a Queer for real and not just a wannabe. I was on top and riding him too and even after we both came and I was full of his load I wouldn't get off him. I sat there with him inside me until he got so soft it wouldn't stay in me. I wouldn't do it with anyone else for a couple of years because I didn't want to have to use condoms. I can't actually feel a guy's cum spurting inside me but now I know why when I used to have sex with girls that they always hated to have to use condoms.

I know how you feel about it running out of you. It kind of keeps the thought of having his cum inside you right at the front of your awareness. However, I usually put a butt plug in when hew pulls out. The plug keeps my mind on it and I love knowing it's in me for hours. If he does me again later, it's a real turn on to feel it back in my cummy hole! The best yet is when there is more than one guy and you feel the next one slide in you while you are full of cum. I have only been gang banged once, but I just love a good sloppy and wet fuck.

Wow! I wish that I had started at 12. I probably would have never done it with a girl.

When I go bareback with a guy I let him know right from the start that I want every drop as deep in my ass as he can shoot it. If I'm not going to get his load he might as well be wearing a condom.

I have only had one opportunity to take it bareback in many years. I met a couple who were both tops that were on PreP and recently tested for STIs. They fucked me on the bed, on the floor, in their sling. After the first one came, the other one slipped in and it was amazing. I agree with all the posts about the psychological sense of connection as a guy shoots inside, maybe even more important than the physical sensation. Man, I wish I could play safely like that all the time. Maybe one day....

Fucking hot as fuck.

Not sure if you were referring to Riki's posts or mine (maybe all of them), but yeah it was fucking hot to have a man deposit his hot jizz inside me while his lover watches, and then have the lover use it as lube to fuck me some more. And the second guy said he was extra turned on by feeling his lover's jizz (usually he just tastes or sees it). That was pretty obvious by the degree of pounding. Nothing like sweaty mansex.

When we were young we always did it bareback - I remember one buddy telling it "it is safer than with a girl you can't get pregnant" and there was something so exciting and "dirty" about knowing he shot inside you.

Then the news came of AIDS and how it was transmitted. I remember thinking "well no more bareback for awhile" but I was sure it would not be long before they had a cure and a vaccine. I never would have guessed it would still be around in 2017.

Same here, "can't get pregnant", so free to go all the way! For the guys I was with the only time he wore a condom was to keep it 'suckably clean':p, and the occasional practice shot for the gf (hey, sounds like a reasonable excuse! lol afterall, some teens were pretty awkward putting the things on) and some wanting to feel the difference on/off/specialty (like ribbed etc). All sorts of experimentation!:D

We never worried about "suckably clean" because on the times it went to anal we knew it was going to finish with anal!

But yeah there were a number of times using condoms as a teaching experience - making sure we knew how they felt and putting them or right "for the girl friends" - only problem was he moved on to the girl friends and left me wanting more! :mad:

I was 16/17, we had been sucking each other intermittently a couple years, this one time he just got his driver's license & got his dad's station-wagon, picked me up and parked in a wooded area and did our usual back & forth oral exchange in the bed of the wagon, but then he wanted my dick in his ass (something that I never encountered, seemed weird but ok) some Vaseline he had handy and he really seemed to love it. OK, your turn!, well he really liked it so I figured what the heck, I'l try it... Owie! nope don't like it. It's ok, takes a little while first time, you'll love it (kept going) you are really tight, relax (yeah how?!) (I'm not getting into it, stings) Clearly remember his throbbing as he shot., not hurting as much., kind of a little rush but I never let him again and it was years before I let someone else try., but was happy to fuck him as much as he wanted. He kept trying to convince me you have to do it a few times before it gets fantastic! (no thank you) Next time, I learned it's important for them not to go in fast first!, but seemed by the time my butt was getting used to the dick and really liking it, they were finishing. I see guys on xtube etc going 30min or hours and wonder what that would be like to get fucked like that. (I know what its like to suck like that! luv muti-cumers! :-)!

Wow - you were really lucky - he wanted you to fuck him! My first time my friend brought Vaseline - but it was me he wanted to bend over - not him!


That is the piece of advice everyone gives - but no one can tell you how the hell do you relax when you have a cock going in something that up to a few moments before was only used as an exit? Relax? Yeah right...

<blockquote>how the hell do you relax when you have a cock going in</blockquote>No one ever told you? Yikes. It's simple.

You relax the rest of your body, take a deep breath or two, and at the same time in your anal region, you slightly "bear down" or "push out" like you are slightly trying to crap. This makes your hole more open.

If my description makes no sense, practice at home on a dildo until it does. BTW, it is also why you (as a bottom) need to clean out before getting fucked. Because most people never want any actual crap to come out, as the bottom pushes his hole open to the cock.

If you have a hairy hole, it helps to shave or buzz-trim the area immediately around it. For me as a hairy bottom: my "hole hairs" being dragged/pulled in contact with the top's dick is quite uncomfortable; especially if he's in a condom. Conversely, a smooth hole is comfortable for us both. A smooth hole plus barebacking (and PrEP of course) is bliss.

Old gay proverb - "If you don't like anal sex, it's because you've never had good anal sex." I think that applies equally for the top & bottom roles.

Being relaxed in general makes a big difference., and sometimes a distraction can work wonders. I remember being very surprised how easily someone (who was fairly hung) slid into my butt when I was busy enjoying myself sucking another.

I was being rhetorical -

I was thinking about as a yoiuth when I first got fucked and my buddy kept telling me to relax -

Distractions like women who "think about their knitting," no. But the distraction you had would loosen me up too.

Sounds like a lot of guys had to be talked into doing something that they weren't eager to try. Relaxing only goes so far. I had the urge to be penetrated early on, and I got a lot of pleasure with the prostate stimulation. So I was well practiced with implements before I got fucked by my first man. I had a little apprehension and it was surely a novel feeling, but I was so satisfied watching and feeling that man on top of me pleasuring himself and me at the same time.

It was in 1982. I remember going to an adult bookstore. I met a guy there, and he took me home with him. We watched porn, and sucked each other for a long time. Then he lubed his cock, and slid it into my ass. I was shocked that it went in easy. I guess my ass was horny. He started slow, then got to a pounding speed. I was on all fours, stroking my cock. His cock was literally milking my prostate, and I was leaking big globs of thick, white cum. He was fucking me pretty hard, then all of a sudden, he tensed up and I could feel the big wad of seed flowing through his long, thick cock as it entered me. I could feel the warm wetness, and about then, I blew my own mega-load. I think I have a better understanding of a female orgasm now. He pulled out slowly, and the warm load ran out of my stretched, used ass. I felt like such a slut, and it felt good! I put my booty gym shorts on (remember it was the 80s), and I went home. I had a huge wet spot in my shorts when I walked through my apartment complex, and cum was running down my leg. I felt like such a whore! lol.

Damn buttpiratesc!

Great first time - to have taken it that easy - I am impressed!

I have since had the opportunity to have guys fuck me in a cruising area in the woods on the way to work, and they came in my ass. I love a hard, deep, fuck! As soon as I get horned up, my ass dilates for the pole that will be pounding me. Usually, the guy can pretty much shove it in hard as long as he has good lube. I don't get fucked very often, as I am with my wife all the time, so I want a good ass fucking when the chance occurs.

first time anal
 

was hanging with some older friends,i was 14, slim fem looking. my best friend was 16, gave me my first bj.
One day we skipped school went over to his hose,just the 2 of us. He asked me to dress in his sisters clothes,which to please him i did.

So we ended up watching some pron his dad had,sitting on the couch with his arm around me,feeling his hand on my nipples drove me crazy,then he started kissing mel, unbuttoning the blouse until he could suck my nipples and rn his hand up my legs. I was so ready for hi by that time so when he pushed me on my back,spread my legs and held them up i was exstatic.he lifted my hips and helf the head of his cock against my hole,pushed it in slow until the head was all the way in and then just slammed deep into me. Kept fucking me for a long time,kissing me and twisting my nipples while i begged for more. ll of a sudden i felt him shudder,then i was filled with his hot massive load. We kept this up for a long time,gradually fully dressing me and going ot on dates,even doubled with a friend and his gf once. I've been hooked on anal since,and still dress sometimes.

I remember playing with an older neighbor boy. I was about 8 years old. He was at least 14. I would go to his house to play, and we would be alone when his mom went shopping. He taught me about jerking off. He had an awesome cock, and he would lay on the sofa naked and jerk off until he blew his youthful wad on his own chest. I would stroke him, and he would stroke me. I wish I wasn't afraid of sucking at that age!!! I would go home, and I would jerk off in the bathroom. Every time I was close to cumming, I would stop because I didn't understand the feeling. Finally, I went all the way, and DAMN! I blew a big load! I have been blowing massive loads ever since. Every time I fuck my wife or a guy, I leave a massive load in their holes. I am very bi and very versatile these days. If I only knew back then what I know now. Shit, college life could have been much more fun!

I always make sure my ass is very clean. I usually do 2 or 3 enemas before sex. Having a clean hole relieves me of the worry of a messy accident. Also, being clean makes you very smooth inside, and you don't feel debris tearing you up.

I always lube up with a lot of vaseline or food grade coconut oil. Vaseline is thicker and takes less. Coconut oil is thinner, but clean up is easy, as it absorbs into your skin.

Entry is done by pressing the cock against my hole, and releasing. Press, release, press release. Take your time and it will eventually go in without effort. Subsequent fuck sessions get easier. Soon, your ass is trained to relax and the cock slides in the first try.

I know that!

I was so scared in college of anyone finding out I was into guys. Back then gays were "queers" or worse and AIDS had no treatments and I was still trying to convince myself that I was going to "outgrow" the fooling around I had done with buddies and I would be happy to settle down with a girl - but I knew better.

All those hot guys in the dorm - I wonder how many of them would have been just as into it as I was - or perhaps more - but I was too busy making sure no one caught me looking in the showers.

I have thought often about the bi guys who were experimenting in college, and how they would have been hot to play with. I could never be gay because I love tits, ass, and pussy, but playing with cocks and asses is equally as exciting for me. During my single years I had my own apartment, and I could have entertained as many fuck buddies as I could possibly want. Now, I have to meet up clandestinely at hotels, in gyms, forest hiking trails, public locations, and rest areas.

I have often wished I had been braver and (slightly) more open back in college. So many hot and horny guys there I am sure I was not the only one wanting to play - but the fear of being stigmatized was so strong back then.

No doubt, a little knowledge back then could have changed my sex life for the better. Unfettered cock sucking and fucking would have made my college years much more bearable. Back then I was experimenting more. I would have topped and bottomed repeatedly while sucking and being sucked. I would have gotten over my concerns about swallowing, and I would have been sexually liberated.