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Describe your first time anal

First time Bottoming! :(

I met a guy online and met him at his dorm and I just planned to get to know him and maybe do oral but he fucked me and it hurt so bad lol it prob was not good for him either cuz we stopped and he apologized I think he felt like he was raping me lol and walked me to the car and kissed me goodnight. It couldn't have been too bad tho cuz he said I had the cutest ass and begged me to call him again which I did but yeah I don't think first time anal is good for anyone who just jumps into it with a college guy who doesn't take his time lol!
Kisses,
Brandon
xoxo
 
I went travelling in SE Asia when I was 22 years old and when I was in Vientienne, Laos, I had taken some diazepam and was just walking back to the hostel when a lady caught my attention and waved to me to come over. When I got closer I saw it was slim, attractive ladyboy. She asked me if I wanted to take her back to my hotel and I decided to just go for it, probably due to the valium. Before then I'd never really considered I would ever had sex with a ladyboy and had only been with girls.We ended up at a 'love' hotel, and started kissing on the bed.She was down to panties, when I reached inside them, she stopped me to say she was a ladyboy, I said I didn't care. After she grabbed my cock and tried to take me inside herself without a condom. Thankfully, I was sober enough to stop her and put one on. It was really tight, and she was really enjoying it and her small dick was really hard.

Afterwards we went for a walk and she asked for some money to buy yaba (meth). After she bought it, we went back to her makeshift apartment that they stayed with another ladyboy. The three of us smoked the tablet through a bong, first night I did speed as well, but it not do too much for me.Then we went back to the same hotel for more sex. I still think about that night all the time but have not been with any ladyboys or guys since.
 
it never hurt to be honest
my guy was a true pro
gave me a hot oil massage and occasionally slipped a pinkie here and there

took what felt like minutes to loosen me up but once it was fully in and I lost anxiety it was the greatest thing I ever felt

like i know sometimes you get caught up and dont lube but at the very least hawk a loogie
a good lover will know...
eh Ill just leave it at that
 
We are all ONE said:
it never hurt to be honest
my guy was a true pro
gave me a hot oil massage and occasionally slipped a pinkie here and there

took what felt like minutes to loosen me up but once it was fully in and I lost anxiety it was the greatest thing I ever felt

like i know sometimes you get caught up and dont lube but at the very least hawk a loogie
a good lover will know...
eh Ill just leave it at that
Click to expand...

Wow, waao. I am so proud that you've finally admitted to this.
 
First anal was really quite uncomfortable and felt like I wanted to use the bathroom if you catch my drift! I am willing to try again and have bought some butt plugs to help train my ass to relax for penetration. Looking forward to next session.
 
the last gf that wanted anal sex i wasn't able too fit it in also.. now its been like 5yrs since i kinda mess it especially the way the other ex took it like ass like a pro kind of felt like a vagina on steroids
 
My first time, I was 17 and with my first bf. I received and it was spontaneous, but he did work me up to it a bit. No lube but then my pussy gets REALLY wet so he just dipped it in there first. It was intense, hurt a little but overall not bad.

Since then, I have had some really good....and some really bad experiences. I have given anal occasionally (tongue and a finger only...it makes a man lose his mind when adding that to the oral repertoire).

As far as receiving anal, I have had a couple of men just do the ram-it-in-no-prep-at-all treatment, and that did not go over well, especially if I bled from it. I have also had anal so fucking good that I came...and squirted from it. I had to get worked up slow (nibbling on my neck will relax me a LOT). Once he works it in slow (no back-n-forth, just inching in while kissing/touching elsewhere), I will get to a point where I start moving on him, and it's ON then.

I am a confirmed submissive, so the top-bottom dynamic definitely plays into my enjoyment of anal. And to the question about vaginal vs anal preference...if he knows what he's doing I enjoy both equally!
 
As a guy, my lady and I have tried it a handful of times, she has even asked for it, but I'm not sure it's for us. We will try it again soon.
 
closetvirgofreak82 said:
My first time, I was 17 and with my first bf. I received and it was spontaneous, but he did work me up to it a bit. No lube but then my pussy gets REALLY wet so he just dipped it in there first. It was intense, hurt a little but overall not bad.

Since then, I have had some really good....and some really bad experiences. I have given anal occasionally (tongue and a finger only...it makes a man lose his mind when adding that to the oral repertoire).

As far as receiving anal, I have had a couple of men just do the ram-it-in-no-prep-at-all treatment, and that did not go over well, especially if I bled from it. I have also had anal so fucking good that I came...and squirted from it. I had to get worked up slow (nibbling on my neck will relax me a LOT). Once he works it in slow (no back-n-forth, just inching in while kissing/touching elsewhere), I will get to a point where I start moving on him, and it's ON then.

I am a confirmed submissive, so the top-bottom dynamic definitely plays into my enjoyment of anal. And to the question about vaginal vs anal preference...if he knows what he's doing I enjoy both equally!
Click to expand...

Cool! Very good response
 
I actually didn't mind it (girl) what I found confusing is that my butt hole was more loose than my vagina! I tried anal the first time when i was having sex for the first. IDK what made my anus looser than my vagina but it didnt really hurt it was more pleasurable kind of pain. we didnt use lube
 
I was 17, it was with a FWB who had a bit of an anal fetish. I was in doggy position and it was suprisingly easy, he used heaps of lube and was very gentle. It hurt initially but he was very mindful and took it slow until I was used to it. It was a good introduction to anal, I still love it. It makes me sad when I hear of girls not enjoying it because their partner was rough or didn't use lube. It can be a very enjoyable experience you just need a lover who is patient, gentle and knows to use lube!!
 
Only given anal and first time I was 18 and my gf was on the pill so we were past the condom stage but I still specifically put one on for anal because I was just young and scared of #2 on my cock. Lol. It was enjoyable I guess but I still preferred PiV with every girl I've ever been with.
 
If you had asked me this question a year ago, I would have said "no way some guys gonna stick his dick in my ass", but all that change when I met my soul mate, yeah I know kinda corny, but it's true.

I was married for 15 years to a guy who never looked at me while having sex, if we even had sex. But I met a guy, an older guy 15 years older than me, and he loved me and showed me the ropes, I love him dearly, never felt this way before, He is kind and gentle, and never pressured me to do anything I didn't want to do.

He did things to me I didn't know were possible. He loved anal sex and I loved giving it to him, because ... well ... I love him and want to make him as happy as he makes me. He would play with my ass while I was sucking him off. I have to admit it felt good. I loved when he would suck and lick my asshole, I was scared Id might have an accident. But it felt so good.

Now one would think the first time you'd have anal sex it would be on a bed, oh no, not me. We did it in the shower. After we showered, we stood there rinsing off under the water, kissing, I was stroking his cock, he was massaging my ass, fingering it. I had this look on my face and he asked me about it, and I simply told him, I wanted him to bend me over and fuck me in the ass, and he asked if I was sure and I said yes. and so I leaned up against the shower wall, and he took his time and slowly and gently inserted it, I was amazed at how easy it slid it. There was a little discomfort at first, but once he started to pump it in and out, it just felt so good, never experienced anything like that.

Now prior to this, I did my research online, read articles, talked to a few people. kinda preparing myself. Now I can't get enough of it. We probably do it once a week (anal). He has a strong sexual appetite for an older guy, we have sex almost everyday, sometimes several times a day. He makes me happy, and so I want to make him happy.
 
I absolutely love anal sex, hence the name....I'm a 36 yr old female and just tried it for the first time a year ago with my guy and I regret waiting so long. When we first started messing around a year ago he would just finger my ass and lick my asshole and it felt amazing. We have a very "experimental" sex life to say the least. I brought up anal first and he was all for it but I don't think he took me seriously at first! Then one night we were messing around and I told him I wanted my ass fucked and of course this made his dick instantly hard. We used a good bit of lube and he was very gentle when he first stuck his dick in my ass, no pain at all and he has a very big dick too, length and width! I came so hard, twice actually, had to play with my clit. Anal orgasims are way more intense and longer than vaginal. I liked it so much that I had him "clean up" and I sucked his dick to get him hard again so he could fuck my ass again. I don't know how he does it but he can manage to keep his dick hard for over an hour some times so he can fuck my ass real good. From then on I prefer he fucks my ass more than my pussy! Sometimes he has to beg for my pussy, it's like a treat to him. And when I masterbate I fuck my ass with my vibrator and send him the vids. I will never tell him but when I fuck my ass with my vibrator it feels better than when he fucks my ass. My vib has a clit stimulator on it so it works magic!!! Shit, I'm horny now, think ima go get my vib and fuck my ass
 
AnalWhore said:
I absolutely love anal sex, hence the name....I'm a 36 yr old female and just tried it for the first time a year ago with my guy and I regret waiting so long. When we first started messing around a year ago he would just finger my ass and lick my asshole and it felt amazing. We have a very "experimental" sex life to say the least. I brought up anal first and he was all for it but I don't think he took me seriously at first! Then one night we were messing around and I told him I wanted my ass fucked and of course this made his dick instantly hard. We used a good bit of lube and he was very gentle when he first stuck his dick in my ass, no pain at all and he has a very big dick too, length and width! I came so hard, twice actually, had to play with my clit. Anal orgasims are way more intense and longer than vaginal. I liked it so much that I had him "clean up" and I sucked his dick to get him hard again so he could fuck my ass again. I don't know how he does it but he can manage to keep his dick hard for over an hour some times so he can fuck my ass real good. From then on I prefer he fucks my ass more than my pussy! Sometimes he has to beg for my pussy, it's like a treat to him. And when I masterbate I fuck my ass with my vibrator and send him the vids. I will never tell him but when I fuck my ass with my vibrator it feels better than when he fucks my ass. My vib has a clit stimulator on it so it works magic!!! Shit, I'm horny now, think ima go get my vib and fuck my ass
Click to expand...

That was pretty hot!
 
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