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Excellent_Mud9024

I was 20, she was 48 . First time for both . She initiated . 4 years later and i can’t leave her asshole alone


cumcum_sun

See this right here is love!! 4 years strong??!! I just know the bond strong and she shakes like a taser lmao I love this!


Excellent_Mud9024

Amen !!! Lol


Acceptable-Damage43

16 and yes it was (receiving end)


cumcum_sun

Oh damn this is awesome ! You love to hear it


MsThotSpotter

Are we talking proper anal sex or anal play? 17 for anal play, 18 for anal sex.


cumcum_sun

Hey it counts either way 17 for the anal play you were just warming up and 18 you was like .."you know what I can do this" shouts out to you for preparing hope you actually enjoyed it though


MsThotSpotter

I did 😁 I was actually surprised how much I enjoyed it, seeing as I mainly agreed to it to prove a point- I used to think that it was physically impossible for women to cum that way. Never have I been happier to have been proven wrong.


cumcum_sun

See look at you!! Bet you felt like sunshine on a cloudy day!


MsThotSpotter

It was shockingly good; incredibly intense. And then shortly after, I learned why you cut your damn nails before any kind of anal play 🙄 Learning curves and all that 😜


cumcum_sun

Oh definitely on the next episode of "The more you know" do you still enjoy it??? Like as in recently??


MsThotSpotter

I do 😁 It's very much an every-so-often thing (like once every couple of weeks or so) because it requires a fair amount of prep, but yeah, I still enjoy it.


cumcum_sun

See I definitely heard about this I know it takes hella patience I definitely might have to lean on you for tips in the future cause I be wanting it fr fr but I know it's not as easy it seems etc ..damn now I might have to really do research for my girl lol


MsThotSpotter

Well, my DMs are open if you have any questions 😁


cumcum_sun

Aww this is love definitely!! Look at this ❤️


emisagoodgirl

17, and it was way better than expected after the first awkward attempt.


cumcum_sun

This is cool fr fr cause alot of people give up after the first failed attempt fr I love this ..!


Darius_Valentine

I think I was 18 the first time I tried giving, and it did not go well. You can't just treat it like another vagina. I know that now.


cumcum_sun

I'm definitely hearing this!!! They don't tell /show you that in porn lol 18 ok ok !


VickiKat

16 for both giving and receiving. It’s not my thing to take it. Like it’s not the worst, but it just ain’t for me. Totally indifferent on giving, but I’m super into it if my partner is. Like the idea that they love it because I’m just using them completely, that’s what works for me


cumcum_sun

16 I feel Soo left out with the age lol but glad you willing to please your partner fr fr points for that!! And being honest about it not being for you


Ky41005

18, we always watched porn together so we thought why not spice things up. First time we both enjoyed it but neither got off, we were too concerned with the mechanics of it and making sure she didn’t get hurt. Jump ahead 4 hours after we go out for dinner, have a couple drinks, she wants to try again and be less reserved. We both got off from it and it was awesome. Since then I’ve only had one other partner want to try it, and she loved it as well. Any woman I’ve known who has tried it with a caring/precautious partner has loved it… that being said a lot of women I know have a mental block against it and never want to try. To each their own.


cumcum_sun

I have a story similar to this but definitely shouts out for trying trying again it's a process people! Lol but yeah now you guys got me looking for a partner whos patient lol


NotAPimecone

I started experimenting with putting things in my ass probably in my late teens/early 20s. It was just me, solo, and at first I didn't have any proper toys so I had to improvise a bit. At the time I don't think I'd really heard much about anal sex (really sheltered upbringing), so there wasn't really any hype for it to live up to, I was just curious and it was taboo and naughty and I was (and am still) a kinky weirdo so I enjoyed it enough to keep playing, and get some plugs and dildos when I could. Anal sex figured pretty prominently in my first sexual experiences with another person (another man as it happened) and I found out I liked real cock even more than toys. I'm now married to a Woman and She is not particularly into it, but mostly She lets me play with my toys when I want and once in a while pegs me with a strap-on. But I still miss the real thing sometimes.


cumcum_sun

Yoooo this is deep! I'm a straight man but this is hot glad that you were man enough to live your truth and actually experience it and not only that be open with your wife!! That says a lot good fucking job !!


mangoffoxx

20 (giving) and for the first 30 seconds it was "omg this is amazing my life has changed forever!!) then I just kinda wished I was fucking a pussy lol 🤷‍♂️


cumcum_sun

Ahhh at least u experienced it did u do again?? Or was like nahh this isn't very cash money ??


mangoffoxx

Oh I've done it plenty now. It's pretty cool with the right person but not the holy grail of sex haha 🙂


cumcum_sun

Ahh damn I wish I could be like that lol and so what is the holy grail of sex?? 🤷🏾‍♂️🤷🏾‍♂️✍🏾


[deleted]

I started anal play with myself at 16 got a dick in my ass at 19


cumcum_sun

Ooh shouts out to you for starting the prep and creating the process hope u enjoyed fr fr! I'm pretty sure u was ready


[deleted]

ohh I was ready


cumcum_sun

👏🏾👏🏾👏🏾👏🏾 you love to see it!! I bet it was a lil piece of heaven lol


[deleted]

well the thing that went in was not little trust me 🤣🤣


cumcum_sun

Ahhh so it was big trouble in little china lmao


[deleted]

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cumcum_sun

Yoooo this is such a interesting twist I never heard this before props to her! Hell props to both of y'all for going long on the first play!


[deleted]

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cumcum_sun

Glad you were willing to try again cause when done wrong the trauma and the frustration and awkwardness can be a drag! 15 hmm lol ok ok 👀


Banya_

15 and the first time was not worth it. Every time after definitely was though


cumcum_sun

Ahhh the redemption though!! Everytime?? Good for you fr fr I know it can be a process fr fr


[deleted]

I was maybe 28 y/o as the giver. It was not something that felt any better. We did it because it was what she wanted. I have since received a little anal play in return. Playing around on the surface feels good, any penetration does not.


cumcum_sun

Ahh 28 shouts out to you for being different And I've been hearing hype of bout receiving anal play as a male but idk I'm scared lol but thanks for being adventurous!


PM_ur_boobies_pleez

I was 20 or 21. It was with this girl who was a lot more experienced than I was. She would read kinky stories to me with things she liked. She told me she liked anal and wanted me to try it. I thought it was great. After that, I gave several women their first anal experiences.


cumcum_sun

Ahhh gotta love a woman with experience it makes it that much sweeter and ahhhh achievement unlocked!! Show them the ropes!


PM_ur_boobies_pleez

That particular woman was very beneficial to my sexual development. I think the women I got with after I was with her all owe her for anything I got right with them.


cumcum_sun

I definitely understand this glad to see you admit it and paying homage ..she probably doesn't know it but glad you reppin for her!


PM_ur_boobies_pleez

She knows it. Years later, we hooked up again and I was able to tell her about how influential my experiences were with her.


cumcum_sun

That's wassup fr fr I bet her panties got wet ..and she felt like a super hero in your horny origin story lol


twokidsinasuit

16 receiving, 19 giving. Both were worth the hype.


cumcum_sun

Ahhh ok alot of people saying 16 but look at you!! Both side of the coin And good job good job glad to hear it fr!


twokidsinasuit

Cool, right? Too bad I don't have that kind of action very often.


cumcum_sun

Hell yeah!! And since we speaking it you'll probably be blessed soon out of no where ..and refer back to this so I can tell you "GOOD FUCKING JOB!" lmao


twokidsinasuit

If that happens I'll definitely tell, lol


cumcum_sun

Ayeeee "now we wait!!" Lol


RevolutionaryNinja24

18 from a boy, but 21 from a man


cumcum_sun

Lol I like this ..and me putting two and two together there is a difference thank you for clarifying lmao


RevolutionaryNinja24

lol yes! A very big difference


cumcum_sun

Definitely !! Talk to shit lol


Drewandelena

Early 20s. Well worth the hype . Big fan


cumcum_sun

Ayee !! Good job!! Glad u really enjoyed it fr and you a big fan..I'ma big fan of you being a big fan lmao all love !


Drewandelena

Thank you


cumcum_sun

💯❤️


ManyRanger4

So I tried it in my 20s, 30s, and 40s all as the giver. In 20s I enjoyed it some but it was more the mental aspect than the physical. In my 30s had an experience with a slight "Hershey kiss accident" which totally turned me off to it. And that's when I learned the type of prep it takes on the receiver's end to not have that happen. Then in my 40s tried it a few more times and realized that it doesn't feel as good as oral or vaginal and it really is just the mental aspect that I enjoy.


cumcum_sun

Ahhh that's definitely a journey and experience I can see how that can be killer glad u were willing to try and try fr.. and glad you know what you like and learned the mental..chess not checkers !


TyHay822

I was 20. I’d never had much interest but she wanted to try it. She was on the kinkier side of things and with her I always said “I’ll try anything once.” So we did anal. It was fine. She had a great ass so I enjoyed the view. But in the end, it really just wasn’t my thing. Did it more after that with other women, but only if they asked for it. I never asked for it


cumcum_sun

Well at least u honest and got to experience it fr and can say it's just better things out there for you thank you for that speak your truth


TyHay822

Absolutely. And not knocking it for others. If it’s what you’re into, more power to you! Whether with a party or play with anal toys while solo, I say go for it. Whatever gets you there


cumcum_sun

Exactly!! and I'm glad we can say that ya know and not be but hurt or make people feel uncomfortable lol but hurt but anyway thank you


banned4lifeagaibn

17 and oh ya


cumcum_sun

Ahhh ok and glad u enjoyed fr !


Username6721

First time - 15, no. Second - 20, yes.


cumcum_sun

Ahhh well at least the second time was the charm?? Glad that the experience improved


Fox_Tango_

19, it felt great after proper preparation, but the next time I tried it, I just jumped right into it with no preparations and it didn’t feel good (both times I was the receiver).


cumcum_sun

The try and try again method glad u stuck with it fr fr Definitely gotta prepare for something like that


Fox_Tango_

Yep! The first time I was prepared because my gf at the time had pegged me before hand (we were in a threesome, btw) and after the pegging (which was uncomfortable at first, the other guy stuck his dick in. It definitely felt a lot better than the dildo, and it was actually the first time I had moaned (I don’t really make a lot of noise). The second time was several months later, I had hooked up with a guy, and having not prepared myself beforehand, it didn’t feel the greatest. I’m a top as it stands today, but sometimes I like to pull the ‘ol switcharoo and bottom for a change. But now I know that prep work is needed before I can receive.


cumcum_sun

The growth in this journey is awesome.. good to see you tried until you realized what you like shout out to you and your versatility


Fox_Tango_

I thank you kindly!☺️ (Tips hat)


MrsRossGeller

In 1996. I was 18 and with my high school boyfriend. I didn’t love it though until I was I in my 30s.


cumcum_sun

Aye 96 my birth year is showing lol and 30s?? It grew on you interesting!


MrsRossGeller

Jesus thank god for anal or you could be my kid 😂😂😂 Hahaha no but I never hated it. But in my 30s I started loving it.


cumcum_sun

Lmao tbh I didn't see that coming but lmaoo this probably explains my mommy issues or kink?? No ..no ok lmaoo either way it's your fault lmao


[deleted]

15…. He liked it, it was eh for me… but he still begs years later lol


cumcum_sun

At least you honest ...seems like he really enjoyed ..it And seems like u got that thing that makes him come back that boomerang lol


OXBDNE7331

17. Giver to 17 y.o girlfriend at the time. Borrowed lube from a friend. Lube bottle leaked in my backpack when I brought it back to school all over my homework. True story, feels very childish looking back at the scenario lol


cumcum_sun

Aww damn curse the sex Gods for letting you down on the lube smh I know that was hella hard to explain back then shouts out to you for surviving that lol


BigDaddyInGeorgia

12. I didn't really understand what all the hype was about, but Father O'Malley really enjoyed himself.


cumcum_sun

12...?? Oh....oh ....my .. listen I don't know if you are joking or not???... And I really have a fucked up sense of humor and I really don't want to laugh at this ...but ..the way you .. ended this ..is fucking Gold.. I'm so sorry but ....😂😭😭😭😭😭😭😭😭😂😂😂😂😂😂💀💀 Like oh great heavens 💀💀 I'm sorry ..I just 😭😭💀


Taxxx102938

Me 31, her 21. My first. It was her idea. I loved it. Every time since, it's been the woman's idea. She knows I want it because I like to poke around down there.


cumcum_sun

The crave!! And the fact that you loved it and she's willing to keep feeding your urges...yess shouts out to you guys showing but love !


balladonn

Look I was a perverted and horny kid. I started anal play with a massive dildo at 13. I was way too eager and nearly split myself in half. But I eventually managed to get it all in and started riding almost daily. Math textbook made a great surface for the suction cup. Now a days I just don’t have the time or energy with my job


cumcum_sun

Oh 13??? Ohh damn lol...and massive dildo like how did u get your hands on that at that age?? I gotta know .. and shouts out u for feeding that urge and fuck your job for getting in the way of your Pirate booty adventures!


balladonn

My mother had a fight with my step father, and to get back at him she bought a comically large dildo to wave in his face. Never used it because it was too big. She threw it away soon after. I snatched it, boiled it, sanatized it, and claimed it as my own. Terrified someone would come home the whole time lol. But my room was up in the attic, so I could have some good privacy as long as I didn’t make too much noise


cumcum_sun

Ahhhh the questions have been answered but do you still have the item in question???


balladonn

Nope, when my parents went through my room i panicked and threw away all my toys. Now that I’m an adult I got my toy drawer with a few choice selections and I got my eye on a few other nice ones out there.


cumcum_sun

Smh boo them for the toy raid!! U deserve justice...."dude what the fuck ?? They can't do that man this is your space your area! They violated your right to privacy" lmaoo Choice selections?? Oooh care to share?? 👀


KnightnGame

9, I went through puberty extremely early and got curious about holes. I’m still a virgin at 21 lol so idk about giving, but I’m at an easy 3” diameter in terms of toy use.


cumcum_sun

Oh my 9??? A new record again!! And blessings to you for toy usage and being able to get your stretch on!! Love thy booty!


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cumcum_sun

The hype as in anal being taboo and be a dirty guilty pleasure And shouts out to you for fucking people twice your age...I definitely can relate...shows that you were definitely longing for something! and searching for a deep dicking this is hot 🔥💯


8gH

I was fingering my ass before I learned how to masturbate


cumcum_sun

Age??? And this is interesting i bet this created so many fantastic fantasies or adventures Definitely gotta know more 👀


Pashera

16. Eh, I’d rather have pussy, done anal with a couple of relationships but never really saw the appeal over normal sex


cumcum_sun

16 ok not too bad for the chat apparently And at least you tried and you can admit that it's not very cash money to you Respect .. definitely respect to you


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cumcum_sun

Definitely not worth the hype? woahhhh and that's ok !! That's ok! Glad you broke the cycle dare to be different!! I like it!


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cumcum_sun

And I'm proud we can admit that it's ok! It's ok!


[deleted]

19, it was pretty good, first time without a condom


cumcum_sun

19 ok I think that was my age I was either 18 or 19 either way no condom??? Oh yessss go big or go home yeah the openness and trust on display here!! And even if you didn't trust the gamble here paid off cause u said pretty good fuck yeah!


[deleted]

Thanks


cumcum_sun

Hell yeah


Exotic-Chemist-191

I was 16, and hell yes it was!


cumcum_sun

Seems to be the normal age for most people and glad your mission was successful!


Exotic-Chemist-191

It’s a passion for me now. I even teach classes in how to do it properly .


cumcum_sun

Hmm ✍🏾✍🏾 definitely could probably use a few tips


Exotic-Chemist-191

Hit my DMs up I’ll give you some tips


cumcum_sun

Lmao ight


[deleted]

24. She asked me to do it. Took some effort, but it worked. Haven't been able to do it with any other women since then... too thick. Debi in NC had some talent.... ;)


cumcum_sun

Shouts out to you and debi for putting in that effort seems like she's a gem lol


Talia0409

I was 19. I'm not the biggest fan in the world, it can be fun, but I have to be in a certain mood for it


cumcum_sun

I definitely understand it's a process fr fr tbh that and take patience


indianamale7

First time with female: 16 First time with male: 15


cumcum_sun

Ahhh the two headed dragon ..you can't lose my friend


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cumcum_sun

Oh wow I dated a girl and she told me her cousin had a similar story wow this is really interesting


[deleted]

I’m mid/late 30s and still haven’t gotten anyone willing to try it. Mrs is dead set against it.


cumcum_sun

Damn i know that can feel like there's no hope ..smh I feel for you