I was a little younger - 52 - for my first time. He was an Asian guy I met at a porn cinema. As we played naked in the booth, he indicated he wanted to fuck me. I thought, "Here goes". He was a nice size for my first - not too thick. I let him know it was my first time, so he was quite gentle. He prepared my hole well, making sure I was well lubricated. The initial entry was a little painful, but he gently pressed himself inside. Once he was in it was wonderful.

So preparation - the right partner helps, someone not too big, and understanding. Plenty of lube, some hole fingering helps loosen it. To prepare yourself you might get hold of a butt plug or dildo.

Good luck. Let us know how you get on.

I was very young when I first took cock up my bum, he was a lot older than me and had been sucking my cock and fingering my bum hole for some time and my little cock had been around his hole as well, and then one day I was sitting on his lap, both of us naked, and he started putting saliva on his cock and gently pushed it a bit harder and harder again, asking several times if I was OK and ready for it, and then it happened, feeling his cock in me that first time was just the most amazing and very best sensation, I will remember that day for ever.

I was 55 when I first tried receiving anal. I had a few experiences with men and more with women and wanted to try to see what it was like. Met a guy when traveling on business and we ended up in my hotel room. It turned out that he was more then interested in showing me the way. He spent a lot of time playing with my ass after giving it a good wash, multiple fingers, a little tongue and plenty of lube. He had me begging for his cock. He took his time and entered me slowly and there was a feeling of being filled up but no pain. The experience was fabulous and I now crave it more then topping. I've had a few painful experiences but nothing to turn me off of the pleasure of having a hard cock plowing my ass.

Not too, many responses to this which surprises me. I thought many more men would like to chime in but thanks for your comments and help. I figured, lots of lube and the right person and preparation are the keys to a good fuck. Still waiting to meet the right guy.

My first time anal experience was when I was about 12...13... in scouts. We didn't know what lube was...other than spit. Ha! If we knew then what we know now.... anyway, my buddy and I were in the tent, giving each other rubdowns and he was straddling my ass. He had an older brother that taught him a thing or two and before long, his hard cock was at my hole, trying to pry it open and slide in. With a little bit of effort, it slid in just a bit and because we were both excited, it didn't take him long to spurt some solid ropes of hot cum into my ass. Fast forward a number of years, in my 40's and once again I decided to explore some m2m bonding. This is when I really learned about the fun of anal, the nerve endings there, and the real meaning of pleasure. I wish I had done this sooner, but with the help of anal-eze, and some patience on his part, I really enjoyed the session. We were both married, so rubbers were used, and a lot of lube. It felt hot to push in, painful a bit at first, but the pressure on the prostate was outstanding. He rubbed against the tate, and not only did he cum, but I did as well. We continued to meet and explore each other, from vanilla to kink.It didn't stop there, but since this is about anal, we will leave it at that. Its too bad that more men don't get over the stigma of "anal" and really enjoy the pleasure that that hole has...again, so many nerve endings...and so much excitement. Enjoy!!

I've had a number of first timers and fucked them. They tend to be very tight, and I recommend they try to lower themselves onto my well-lubed cock whilst I lie back. One they're opened up like that, I can fuck them in a variety of positions - my record with one married guy was 6.

I'm an anal virgin, never topped or bottomed. More of a top type guy I think however, the thought of being taken is of some interest to me. I'll probably never experience it, ..I have an extremely tight ass and would only surrender myself to a man with a slender penis, and they tend to be in short supply. (no pun).

I was first fucked when I was 19, and the guy was a bit impatient and I didn't know how to relax so it was a bit painful, but since then I've learned a lot (practice and theory, mostly practice).

If you have a dildo of similar size to your partner, then you can practice a little bit. It doesn't have to be pleasure, but just no pain is kinda enough to make sure you can accommodate penis of that size.

I was 53 and really wanted fucked. The guy was gentle and slid right in. Been hooked ever since. I offer my hole every chance I get.

In my late 40's - used toys but wanted areal one. First time was a bit unpleasant - the guy was thick, and I was still pretty tight. Second time was a couple years later, and I was more prepared and the guy did a fantastic job -rimmed me, opened me up gently, and thoroughly pleased my asshole.

Was from my step dad, it started with each of us just jacking off into a towel. Then it was mutual jack off again shooting into a towel. Then we progressed into sucking each other, which I really loved when he came into my mouth, he pulled off my cock as I came and caught it with a towel. Then it finally came the night when he had me fuck him, which I liked, then he wanted to fuck me, well I was afraid as his cock was bigger around but shorter then mine. He had used Vaseline for lube for me, and he would also use it for when he fucked me. He was very gentle and when he pushed the head into me it stung a bit.He stopped and just held it there until the pain was gone, then he pushed more in, held it for a bit, pushed more in and finally he was all the way in, think his cock was just shy of six inches. He then pulled almost all the way out then slowly pushed all the way in, it felt so good and II told him so.He said then he was going to start fucking faster, wow did that ever feel good, then when he came I felt the heat from his cum, it was so very pleasant and felt so good I ejaculated too. After this it was routine, I sucked him, he would suck me a little but did not want me to cum in his mouth. Then he would fuck me, and then I would fuck him. This lasted for about 3 years or so, then II enlisted in the service, I really missed suck his cock.

On my birthday I came home and found my college roommate naked in my bed (we’ve been sucking each other since we both came out to each other.

He said “Happy 21st birthday! Let’s fuck! I topped him first then I gave him my virgin bottom. Best birthday ever!!!

I was around 40 my first time. I had been playing with toys and other objects for some time so I thought this should be a breeze. Well, it's different when you aren't the one dictating the penetration.

Even though he was gentle and took his time, it was a little painful to start with. Eventually, I relaxed and he was able to fully enter me...he was around 7". Once he was in and I was relaxed he pumped slow and easy until he filled his condom.

It was the start of me needing to be fucked. Since then, I have had many men and now like it on the rougher side...pound my ass!

I did have a semi regular guy a few years ago who was very much a making love kind of guy. Sex with him was wonderful and included a lot of caressing and cuddling. I liked that a lot but still I'm a slut at heart.

I, too, was sitting on a guy's lap and he started working the head of his cock into my ass. We had lubed already from the fingers and toys that preceded. He just let the head rest in there and I got used to it; then he pushed in a couple more inches and the feeling was wonderful. Soon he was balls deep and moving slowly in and out. I was jerking mine and came before he did. He stayed inside while he went soft afterwards, and the full feeling remained. I'll always remember him and his cock.

My first anal I was 17 and I met up with a guy from craigslist he was much old and stocky, we met up in the woods and we took turns sucking each others dick and ball sack, when he was sucking my dick I suddenly felt a finger press up against my hole and then 2 fingers ✌️ and he pushed them inside while he was sucking my cock and slowly started to move his finger in and out of my ass after a few minutes it was feel amazing and I was ready for him so I stood him up, I got down and sucked his cock for a minute to stiffen it back up.nice and hard, he started to slowly face fuck me started feeling his ball sack hit my chin it was so fuckin hot, after a minute of that he turned me around and pushed me.up against a tree I felt his finger rubbing my hole as he spit a few time and then he started to put his cock in my ass, once he was in it hurt a.little but only for a second and start to go.in and out and within like 2 minutes he was fucking me at a good pace I felt so much pleasure it was amazing I couldn't get enough just before he was about to blow his load i leaned forward off his cock and quick turned around got my mouth to his cock just in time as his hot sperm started to fill up.my mouth 👅 of course I was kinda new and young so I spit it out but it was an amazing first time experience!! If I could ever have the opportunity to hook up with that man again I would have him dump the load in my ass instead

I was around 13 or 14 I think had a sleepover and one thing led to another and we ended up naked with me doggy style on the floor.

My first time anal I was 34 years old he and I were dating and decided to meet at a hotel and he is about 6.5 uncut and thick he was very gentle and after the initial sting on the entry was over I found I was a natural bottom. I love the feel of a cock in my ass and since we are now married I love bareback. I had several experiences as a kid attempted anal but never really made it all the way in.

It was with a construction/handyman guy who was building our home's second floor. He was around his mid 50's or so he looked. Lol. My mom sent him lunch upstairs because she didn't like for him to come downstairs all sweaty and dirty. Plus most of the weekdays she entertained her bridge friends. I used to bring the lunch upstairs to him. And we started talking. One time I saw him naked from behind changing his clothes but it was until I saw him peeing that broke the ice. He asked me if I never saw an adult penis before and I said no. I remember I was so exited that I felt my heart in my throat. I told him I didn't knew it had hairs and he laughed. He asked me if I wanted to touch it and I said no. The next day he barely talked to me and I asked him why? He said his testicles ached because of me.
I asked...how or why?
He said because he got very exited the day before and he couldn't release himself.
I didn't know what the hell he was talking about but he asked me that if I wanted to see it again.
I said. Ok
So he took it out and got close to me. I was sitting on a brick and that thing was right in front of my face, so close I could smell it. He was very exited and said: "just touch it once ok?"
So I did.
That was a Friday...
Things escalated from there very fast.
The next Monday I was so exited and rushing my mom to finish his meal. Lol. So I could bring it up to him.
That Monday he made me suck his cock along with his testicles. He kept telling me that if I said something to anybody, the police would take him to jail and there they would kill him. So he made me swear I wouldn't tell anybody. Plus. As a bonus, omg lol. I was so innocent... He would show me how the babies were made. So. Of course I never said a word to nobody just because I wanted to know something that neither of my friends knew!!!
So I was kind of greedy lol.
That day he was very busy but told me that the next day he would teach me how babies were made.
So the next day, he asked me to bring some butter from the fridge. I ran down and up stairs in a second.!!!
He told me that I had to pull my shorts down. I asked why? And he said... Well... You want to know about the babies or not???
So I pulled my shorts down and he bended me over and started to put butter in my asshole. I started to feel his finger going in little by little then out then in again. He asked me if it hurts and I said no. So he started to slide a second finger. I remember my little penis was very hard and my heart at my throat again.
He said ok I think you are ready.
I asked innocently... That is how?
He laughed again and said noooo.
Then he proceed to take his penis out for me to suck it. So I did.
After a minute he got more butter and started to finger me again. This time it was way easier. As I felt more fingers inside.
He placed me on all fours and kept opening my asshole.
Next time I knew I started feeling something more soft but firm sliding in.
When I noticed both of his hands holding me by my hips I realized he was pushing his penis inside my asshole.
It was an enormous sensation of fullness.
I felt his pubic hairs touching my buttocks. Then he pushed me forward then back again.
After a couple of minutes he filled my rectum with his sperm.
He pulled out and made me lick his penis clean.
I again asked innocently... Now what?
He laughed again and said... That's it!
That's haw adults make babies.
But aren't the girls who can have babies? I asked.
He said... yes but this is how it's done.
Of course the girls have another hole where your penis and balls are located and that's where you are going to put your penis one day ok? But this is how it's done.
Did you like it?
I said yes.
So he kept doing that to me until months later that he finished hour second floor.
I never said a word to nobody.

I was a very late starter. I was 65 when this guy - about 60 - fucked me. I'd had my first gay experience a few months earlier where I was sucked and rimmed (first and last time - a shame because I loved being rimmed. I then chatted to this guy on Caffmos who offered to fuck me. I agreed and went to his house in Hastings East Sussex. Unfortunately, he didn't prepare me properly and it was extremely painful. I was wary the second time -about a year later - but he prepared me properly and, instead of entering me doggy as the other guy did, he put my legs over his shoulders and fucked me missionary. What a difference! What a fantastic experience! He came inside me. If you look at my photos - there are 3 of my cum-filled pussy. Absolute Heaven!

My best friend and I became aware and learned how to get our mutual rocks off. After a couple times stroking each one, we went into sucking, 69, and within two weeks we were fucking three times a week. We had sleepovers, which we used for fucking each other raw. I always preferred to be topped first, as I am anally-multiorgasmic in a way that I will keep cumming as long as my mate strikes my prostate good so, out of a regular fucking from my pal, I would have cumm three or four times, but did not get wasted and kept hard and horny. I was usually last to fuck my friend, and that penis cumm indeed wasted me and had to rest. But alas, we were so young that in a couple hours we would be at it again.

It is an old stream this one. Very likely, you have gotten your deed done already. If not... be patient, do not rush.

I have seen all too much that is a sort of pride "to take a cock", as if it was a sort of pageant or health demonstration. Please do not sacrifice yourself for making things too fast.

Let your partner know that you are ready, and relax to accommodate to his girth. You have a magnificent cock, but trying something like that in a virgin pooper is highly inefficient, from the pleasure point of view. Make him push and wait; a little pain is okay, but it must not really hurt; you dont want to get bruised there, as you will not be able to repeat soon. A considerate lover must look for his pal's enjoyment, as well as his own. And let him know you are having a good time thanks to him.

MY PERSONAL point of view, is that I enjoy the most when my friend's butthole spasms around my cock, and I help his sperm to shoot harder with my knob contribution over his prostate. This triggers my own orgasm in a delicious communion of pleasure, health and fun.

Mid twenties for me, surprisingly it didn't hurt, I must of had a good teacher/top, plus me being a little tipsy helped, now I prefer 100% sober, plenty lube, big, raw cock

I have had not so great experiences being topped.
My best experience was with a FWB.
He kind of did what your guy did.
Played with my butthole with fingers, start eating my ass, apply some lube then finally slowly enter me. Every time it was amazing.

My first time was with an older guy. He only used his fingers and didn't use any lube so it hurt a little bit. Now when he was doing this I was fucking his wife. That is the extent of my experience

Anal was a big step from stroking and sucking on man cock. My mentor was very helpful about enjoying anal pleasures. Lube (cherry flavor), the one, two, three, four finger fuck to loosen up the rim. It was a process and it felt so good. When he pushed his cock inside of me, I came and begged him to keep fucking me. The paradise felt like forever, but it only half an hour before he pulled out, spun me around and painted my face, my tongue, my open mouth with his cream. He made sure my cock was happy, which is why I make sure the young cocks I mentor are taken care of.

Everyone has their own style and desires. Respect them, cultivate them.