First Time Receiving Anal

[towhead5]

What was your first time receiving anal like? Was it planned? Who’s idea was it to do it?

 

[beginner63]

It was great. I had been sucking a guy who was an experienced top. I told him I was ready to try bottoming. I had been using a dildo for years so was used to being entered but a real cock is so much better

 

[deleted5199391]

I'll take some details off.
Was a guy with I had already some sexual encounters. Sucked him, mostly.
Once I asked him if he wanted to fuck my ass.
Didn't work. He was too big, I wasn't relaxed or wet enough. He couldn't penetrate me.
I kept sucking him, while making my fingers wet from my saliva and his precum, and then playing with my anus.
Then I felt relaxed. He made me lay on my back, and did try to push his cock into me.
He still couldn't enter, so he did raise my left leg, and suddenly his cock slid into my ass.
He fucked me like this slowly, then pulled my right leg and put both of them on his shoulders.
I was basically folded in two, his big cock going in and out. It hurted but I asked him to put it all in. It took a while but he did.
I kept kissing him and tried to move my ass but I was nailed on the bed, had no control of that.
After some time he came into my ass. Since his cock was clean i asked him to sit on my chest, so I could suck him while I wanked my dick. I came, end of story.

 

[erpap]

Attempt first time was with a guy who was rather large. Every time we would fool around he would come to bed with a condom and lube. Never having had done anal at this point I was nervous with him being very large. One night I was on my side and he pulled me into him and his cock rammed my hole dead center! I saw stars, I gripped the side of the bed and he tried to pull me close to him but could I gripped the side of the bed so hard. And he was a much bigger and stronger guy than I am. First time I actually had anal the was a bit of pain but nothing that didn’t subside with in a few moments. Now I just want to be fucked 24/7 LOL

 

[SwitchyNZ]

Was a teeanger, with one of the few guys I'd regularly do stuff with. We'd been building up, watching loads of porn, fingering etc. Decided we wanted to try it. Stole his brother's lube. He wasn't that big, so it wasn't painful. But I didn't get much out of it (he did!). But slowly built up to enjoying it

 

[DiomedesXVI]

It was planned on my end, but not the tops haha. So I’m almost always the top. It’s pretty much expected due to my cock size. But when I really trust someone and am into them, I don’t mind bottoming on occasion.

My first time as a bottom was very good. I actually think my extensive experience as a top really helped me prepare for my first time as a bottom. The top was a good friend of mine and he was well-endowed too. So I had a good idea what to expect taking a big one, because I just thought back on all my times of being a top and what difficulties my bottoms faced when taking my big one.

So, with that in mind, I prepped myself with all the usual cleaning and what not, then also ample stretching and relaxing my hole. And when I did ask my friend, in the spur of the moment while we were getting intimate, if he would top me, it was relatively smooth taking him.

Bottoming is honestly all about prep, and not psyching yourself out. If you continually ruminate on “oh it’s going to hurt”, then you won’t be able to relax and yeah it will hurt because you aren’t letting it not hurt. The more relaxed you are, the easier it is to adjust to fitting a dick in your hole.

 

[flatiron]

I found it really hard to get relaxed. Getting my brain to tell my hole to loosen itself up, and getting my hole to respond, wasn't easy. First time was a bit strange!

 

[latinluva]

Not planned, was painful....definitely needed to go home and learn how to take a big cock (bought three different sized dildos). Cleansing, lube and size adaption exercises. Learned how to manipulate my prostate (Helped with positions and dick curves). Just never know what you're gonna get. I just made sure that every time I went to the adult arcade/gloryhole, I was prepared and slightly opened for him, making it easier for him to enter me. Always had small packets of lube and different sizes of condoms for a snug fit. There was always a small line of guys waiting there turn if I went at the right time. Lunch time was great or Friday and Saturday nights around 10 o'clock. Never went home unsatisfied.

 

[diver6]

Was a teeanger, with one of the few guys I'd regularly do stuff with. We'd been building up, watching loads of porn, fingering etc. Decided we wanted to try it. Stole his brother's lube. He wasn't that big, so it wasn't painful. But I didn't get much out of it (he did!). But slowly built up to enjoying it

I was the same, just having fun experimenting with my buddy in our early teens do our cocks weren’t all that thick yet which made taking them easier. We didn’t have lube though just spit and lots of precum.

 

[bi2]

What was your first time receiving anal like? Was it planned? Who’s idea was it to do it?

Ive posted this before in another thread. Here it is:

The first time it happened, I was totally shocked and speechless.

It happened with an older and larger neighbour that gave me massages ongoing. He had oiled me up and in particular my arse, really good and proper while I was laying on my stomach.

I have had several massages with him beforehand and trusted and enjoyed everything we did previously. So going down this path felt a natural progression of our relationship.

When he asked me to flip over, on this particular occasion he strongly lifted me up and turned my arse towards him with my legs hanging over his shoulders. I smiled and quietly asked him, "What are you doing?", he smiled back and kept quiet then proceeded to enter his dick slowly and carefully into my hole, telling me to relax and breathe.

After he entered and slowly thrusted away, I felt so hot, desired and sexy, I couldnt stop groaning, while he was grunting away with each thrust.

I have said it before on here, I was lucky that my experience was with a very kind man.

 

[midwesthubbi72]

First time received and was from an older woman. She pegged me. She had a tit for tat anal rule. Spent a year with her. Learned to love it. First time I was bread by a man was two years later with a gay friend. We spent to whole weekend fuck each other. Nothing like the real thing. Wifey peggs me at least once a week.

 

[CaptainGrey]

The first time I receive anal wasn't ethically great, but it was still good. It was with a guy I had met on Grindr and talked to for several days, but I didn't tell him he was going to be the first person to fuck me. Which made me nervous all along because I didn't know if I was going to be able to take him. He had a very nice uncut dick with a similar length to mine but wasn't as thick. We finally met in his car hidden in his indoor parking lot. Neither of us could host but since we really wanted to finally see each other we didn't wait for a better opportunity. We first spent a lot of time making out and sucking each other's dicks, I could feel that we were really into each other. Finally, we completely undressed and went to the backseat. He had a hard time getting it inside me at first and it really hurt me a lot, but once he was able to slip inside easily… God how I loved having him in me ! The transition from pain to pleasure reacted in me like a drug, I was in a trance the whole time ! We were constantly changing positions and he fucked me so long that the whole car was covered in steam and us in sweat. We dated for 4 months after that and I also ended up being the first to fuck him in the ass.

 

[pnwboy]

I'll never forget my first time because it was so emotional and amazing. The man who opened me up was much older and had a very thick cock so it took several months before I could take him fully inside me. We started out just kissing and cuddling when we realized there was this unplanned, natural attraction between us. I was a virgin and he had never been with another guy before so we kinda learned together.

I loved knowing I could rub my butt on him and make him hard and knew that he wanted to be inside me. Thankfully he was always patient and loving so never forced anything out of fear of hurting me. So there was a lot of anticipation built up after weeks of stretching and learning to relax and just being able to fit the tip in. When I was finally ready to go all the way I prepared myself and let him know. He was a little apprehensive but I assured him that I wanted us to experience it together.

So we went to bed and made out for awhile until he was hard as a rock and dripping with precum. Not gonna lie, I was pretty nervous. He made sure I was well lubed and pressed his huge cock up against my hole. The head popped inside me and he paused to make sure I wanted to keep going. So he slowly pushed deeper and it felt like I was going to tear in two even though he was only halfway in. lol I relaxed and soon that pain became something that felt better than anything I had experienced before. It felt like I was molded perfectly around him as he slowly started moving in and out. He told me he loved me and said he was all the way in and I felt his hairy balls hit my butt. I felt so proud and so close to him.

It only lasted maybe a couple minutes and he asked if I was ready. He thrusted hard 2-3 times and I felt this hot pressure deep inside me and I instantly shot my load. It was so intense I thought I was going to black out. lol He enjoyed it so much he had tears in his eyes and got all emotional. It was an unforgettable moment for sure that changed our relationship. We didn't get out of bed and made love several more times before falling asleep together.

 

[DPHusband]

We were young, 4-5 years apart. In a group home. He treated me like shit on the outside. We were in the Rec Room watching TV on the same couch sharing a blanket. His foot “Slipped” and rested on my crotch. I looked at him and he was still watching TV. I slid my foot forward and rested it on a huge Hard on. I slid my foot up and down and he didn’t flinch at all. I am so horny at this point.

i reached under the blanket and found his thigh, I slid my hand hand back and forth a bit and brushed his nuts though his shorts, he never flinched. I slid my hand down and felt his big hairy balls and his hard shaft. I pulled his balls and cock through the leg of his shorts, he was so hard and his heavy balls flopped out. He turned his head and had this shitty smirk.

i stroked his thick hard cock and played with his his huge saggy nuts. He was pre cumming like crazy. I got up and turned the lights off. I came back and he had taken his shorts off and laid back against the armrest. His hard cock and big saggy nuts were laying on the cushion. I took his throbbing head in my mouth, tasting his dripping pre cum in My mouth. He tried to push me down on it. I held back.i tried to suck it like i had seen in porn movies but he had so much more.

I laid a blanket down and tried to have him lay down, he had a full bush and I buried my face into it. I told hi to lay on his back and he said no.i tried to take his monster into my throat and only got half way. He told me to lay down, i, of course did. He started to slide his huge fucking cock into my ass crack. He fucked my wet hole without penetrating me until he blew his thick load.

His head slipped inside my willing hole a couple times, I was so loose he could have pounded me, but he dropped his hot load in between my willing crack. I had to shower to clean him off, but i jerked my cock so hard.

he made me a size queen.

 

[DPHusband]

He walked down the hallway naked, his soft cock bouncing between his thighs, his low hangers trapped between his thighs. I stepped out of my room eager. He went into the shower and I followed him. I told him to bend over, he said no. I pushed him over and saw is tight hole in front of me. I brushed my tongue against him and he moaned so loud. He sat on my face and stoked his cock while i tasted his sweet tight hole.

he came all over my stomach and begged me not to tell

 

[Uncle_Bob69]

Back in the day, 1990’s, Undeveloped section of Willamette Park, Corvallis, Or.
After a couple of months, exploring and participating in numerous BJ sessions, I decided to just go for it,
From the North boat ramp parking lot, about a ten minute ride from my apartment, it’s about a 5-10 minute bike ride to the cut-off and a myriad of trails that led to the nudi gay beach section. Depending on how crowed the trails were, determined what to wear and when to start stripping. Usually, I’d start riding in wearing cut-offs, then strip down to flimsy, revealing short shorts by the time I got to the beach and walked my bike the rest of the way.
The “beach” was just a half/mile gravel bar backed by brushy areas full of lil trails and private “sex nests’ flattened out in the tall grassy areas.
On the day in question, I decided to wear a woman’s thong, underneath my cutoffs I had “found” in my apartment complex laundry room. This was the first time I paraded around wearing panties in front of peopleI didn’t know. My hardon was sticking out of the front of the panties , showing just the Missile tip cock head. I dropped my bike off near a nice semi-secluded spot with a view of the river and started cruising.
Awhile later, after I had made a couple of rounds, as I came back to my spot, I noticed someone eyeing me from the river. Just then, I noticed a local yocal, always willing to suck my cock,and swallow my load, waiting by my bike. I warned him, I hadn’t jacked off yet, so be careful.. So we laid down on the towels, positioned ourselves and as he rested his head on my inner thigh, he pulled the front of my panties down and I slowly pumped his mouth as he played with my asshole.
Awile later, the guy from the river walks up and my cocksucker stops sucking with my cock plopping out of his mouth and introduces me to his buddy. We chatted back and forth as they commented on my cock and ass and panties, and then he started fingering my ass deeper as I fucked his mouth.
Soon enough, I exploded, gushing, making his cheeks puff out, but he didn’t waste a drop.. Then he kissed my cock and we thanked each other, as he looked up to his friend Steve, saying “have fun buddy.”.
Steve asked if he could join me, and as I nodded yes, he laid down and began fondling my butt cheeks, mentioning how much he was checking me out, numerous times before. By now I was quite puffy hard again, and he asked if I wanted to 69. I thought he meant , sucking , until he said, “sit on my face”. So I squatted on his face and bent forward, as I began sucking his cock with him playing with my ass. I thought he was gonna suck me until he asked me to schooch back, as he spread my cheeks wide open and moaned.
Steve began tongue fucking my asshole . It was the very first time I had ever felt anything so wonderful! I moaned in ecstasy as I attempted to deep throat him..
After a few minutes, he whispered what a nice tight ass I had and wondered if I had ever been fucked. I was already feeling like a shaky Gumby with so much adrenaline and stuff rushing through my brain , I grunted, unh unh, no..
Steve groaned , “ you wanna fuck?” and I nodded yes.
So we got our stuff together and walked back into the brush awhile to a very secluded area of the trails. I was so horney, I got down in doggy position with my head on the towel and spread my cheeks apart, whispering how much I wanted to get fucked., Steve knelt down and ate my ass out for awhile and then asked me if I was ready. I moaned, “Fuck my ass”
He whispered he’d go slow and for me to breathe and relax as I could feel him lubing up my asshole. It burned so much at first, even though he just had his cock head inside me. As he squeezed my butt cheeks playfully, he moaned, when ever you’re ready, just slowly push back.
I slowly rumped back and forth in his cockhead until I felt it go inside deeper and felt his shaft inside. It burned a little but I was insatiable, seeing stars, etc.. When he passed my second sphincter into my rectum, we both sighed and moaned. I had never felt anything like this before. I started babbling, Now I knew why the women I fucked up the ass loved it so much. Steve laughed and began fucking me .
After awhile, he mentioned he was getting ready to cum and wanted me to lay on my back. As I felt my asshole, I couldn’t believe how gaping open I was. I began babbling again how I’d played with dildos before but this was the best! Steve wanted to make sure if it was alright if he came inside my ass, and I nodded yes, making him moan as he took ahold of my ankles , spreading me open and moving my ankles almost level with my ears..and then he really started fucking me with nice , long and deep strokes until I felt his cock swell and I clamped my kegal muscles making him shout as I grunted and whined, feeling him Shoot his cum up inside of me, four or five spasms..
I can’t remember how long we laid there, but it was getting on to evening. He offered to drive me home , which was so helpful, since I still had Gumby legs ..
After that, I was hooked, I had crossed my Rubicon. I saw him once again a few weeks later, this time we had an audience..then I never saw him again, but a few weeks later, at my apartment complex pool, I noticed this guy eyeballing me with a big grin on his face. I was walking by with a laundry basket on the way to do my laundry. A few minutes later, he came in and introduced himself and leaned close, whispering, he watched me get fucked at the river other day;
I blushed and giggled. I gave him my apt. #. The rest of the semester, he sodomized my ass multiple times, once a week

 

[Lukeyjukey]

Id been fooling round wi guys for maybe 4/5 months and done everything else but didnt really have any desire to bttm. I had used my own fingers a few times but didnt get anythin from it.

i was in ireland wi friends and i was stayin a few days more than them. Told them it was for a job interview (none of them know my bi side) but really jus a chance to explore. Went on grindr and talked to a few guys. Met up wi 1 and went to his apartment. Sucked and i fucked him.

spoke to some more guys over the next few days and kept in touch wi the first guy. He invited me back to his on my last day before flying home. I was lying on my front n he was eatin my ass n started to put a finger in. I was horny af and told him fingers did nothing for me and if he wanted he should try his dick instead. He was askin if i was sure n i said do it before i have the chance 2 change my mind. I went soft as he went in but seconds later was hard as diamonds. We got pretty rough n i discovered i liked it a lot. He shot inside me (in condom) and i shot all over his bedroom.

some of the hottest sex i ever had. Pretty uncomfortable flight home thou

 

[Appreciate]

It was a borderline spiritual experience experience. We both wanted to do it and had built up to it. Now I want it all the time.

 

[Scott8361]

My first time anal happened the first time I ever tried having sex with men. I was in my late 30s and responded to an ad from a gay couple looking for a straight guy.

It turned out the did everything to me! Body massage, licking, sucking, rimming, fingering my hole!

At the end one of them blew me to a final climax, and then his partner rolled me over and had me stand over the edge of the bed so my torso was face down on the matress. I heard him open a condom package, slip it on, and slid it deep inside.He had a nice thick 7 inches.

He pounded me HARD! I was pinned between the bed and him, taking the full force of his body slamming against me. It was hot but brutal! I was happy when he finally climaxed! His cock didn't hurt inside, just the body punishment received outside!

I haven't fucked a lot since, but have had some better, more sensual experiences than that first time!

 

[HorseHung40's]

I have only given it