When is the best moment to surprise him with anal?

[Anonymous]

I have been having sex with this hooot guy for like 10 days now. Every single day. The chemistry between us is crazy and we just can't stop dominating each other. I've had a crush on him since I was 10 and he was 11. I am 18 now, he is 19. I saw him for the first time in 8 years and we have been inseparable ever since. It's important to mention that only the PHYSICAL attraction is there, there are no emotions, at least not from my side. I will dump him soon, but I wanna seize the day and have the greatest sex while it lasts. It is already hot AF. He is very skilled, he can make me orgasm threw intercourse, but he also likes eating my pussy out. A LOT. He is very "thirsty" all the time, wich I love, there is a lot of making out, dirty dancing in clubs, PDA, ass grabbing and tit grabbing wich I love. I also enjoy giving him oral, wich I rarely do to other guys. I love his popsicle. The thing is, since it will not last forever (although he doesn't know that yet 😝), I want him to remember me as the best sex he ever had, so I wanna try anal with him. I've already had anal before and I love it. He has never had anal before. How to initiate it in the hottest way possible and make it the best sexual experience he will ever have? All ideas are welcome!!!

[Shaft50]

Haha, so you're going to punish him for something he did when he hardly knew he was interested in girls, because you never forgive. I wonder what you may have done in your childhood years that others could hold against you and get revenge for... so, to punish him, you want to give him the best sex he's ever had, make him feel wonderful physically and then dump him when you think he's fallen in love with you? What if anal doesn't bring you closer? What if anal is his red light, something he finds detestable and would never do with anyone? I suppose, he'd break up with you at that point and your years of plotting revenge would have been wasted...

[Asker]

I haven't spent years of plotting revenge. He moved when he was 11, I haven't seen him since then. It did take me years to get over my heartbreak, but I wasn't planning on revenge ever until I saw him in person 10 days ago, that brought back all the feels. Besides, why do you think he would mind? At least he got to have hot sex...

[Shaft50]

Chances are, he is just having fun at the moment... no feels in it for him... so, it's win/win for him...

[Asker]

At least it will be a win/win for him, but it is definitely a WIN/WIN for me! Yass! But I doubt it, he seems really into me. He is blushing around me. His parents are really nice to me and respect me, I even went shopping with his sister (it was her idea), and his grandma (who is my neighbour in the town where I live) is nicer than ever. I am currently staying at his appartment in the city. And one more thing: I will be moving to USA permanently in about a month and he doesn't know it. So imma still catch some fun and dump him before I leave.

[Shaft50]

Riiight... it sounds like you won't have much to look forward to once you exact your revenge on this poor guy...

[Asker]

What? 😂 Are you kiddin' me? Imma have so much to look up to in the future! He is just an episode role!

[Shaft50]

Thanks for mhg :-)

[Asker]

I didn't give you MHO. Someone must've hacked it.

[Shaft50]

Hahaha... I'm taking it anyway! :-)

[Anonymous]

When you're reaching a sort of climax during regular sex, just look at him and tell him to fuck your ass. Do it in a "thirsty" manner. Show how much you want it. Dirty talk a lot.

P. S.: do you really wanna dump this guy? Not even keep him as a fuckbuddy?

[Asker]

Yeah. I wanna dump him! I can have almost any guy I want, I don't ever want a relationship with anybody and I wanna dump him to hurt him because when we were kids I invited him on a date and he stood me up. It took years to recover!

[Opinion Owner]

The guy was 11yo, nothing more than an idiot. Do you even know if he's the same kinda guy as back then?

[Asker]

He was always this cocky little kid and he still is. Even at 11 his flirting game was STRONG! One time he grabbed my hand and I said: "Be nice to girls" and he said: "I am not your boyfriend to be nice to you. Unless you want me to be..." And I thought to myself: "Hell yeah!!!" He is SUCH a big flirt, but not in a cute, charming kind of way, but in an incredible sexy, passionate and intense charismatic way. He used to break windows at night in our elementary school, he was always the bad boy. His mother was one of the hottest girls in our little town back in the day and his father was a farmer who used to do black-marketeering in the 90s during the War (this is all in Serbia, Euroe) and that's how he got some money. He has a older sister who is a genius and the most successful student on a good University... And him... Arghhh. If sexiness was money, he would be a millionaire. He goes to a shitty collage... Bad student. Bad boy, AMAZING in bed! It'll be a pleasure breaking his heart!

[Opinion Owner]

Hmmmm. Mind to ellaborate a bit more on the whole "big flirt" thing? It might be useful...

[Asker]

First, I am talking about how he behaved when he was 11. We met in May on tennis classes and we would see each other at least 4 times a week. We were in the same group. He was, unlike guys his age, not shy around a girl (me), he always wanted to stand next to me, to touch me to "show me some tennis move", he would just basically be all over me, we would talk during the whole one hour class. He would compliment me on how I dress, he would stare all the time, he would point to the Puma on my yoga pants and be like: "Puma, that's wild, like you!" We would play against each other and he would always let me win... And know he is whispering dirty things in my ear the whole time, like, stuff he wants to do to me, he is touching me, he is very public about expressing how attracted he is to me, wich I like. I like that he is not shy and is very open. I hope that, now that I've explained you even how his family looks like, you have a clearer picture.

[Asker]

by the way, he used to live on a farm in a village near my small town. We went to the same elementary school together in our town (population: 3000). He went to High School and is in Collage in a much bigger city right now (population: 200 000), it is about 50 miles away, but I haven't seen him in 8 years. He comes back rarely. I guess it is because he was made fun of the fact that he is a village boy, although, he isn't poor (not that it matters). His parents bought an apartement in the city where he lives with his sister.

[Opinion Owner]

Nice. Thanks for the insight

[Anonymous]

You should give him a choice. The last two guys I've slept with, in fact, weren't all that into anal. Maybe text him something like "You've been treating my pussy so good. Wanna try the ass?" since you said you wanted him to think about it a while.

[LaurenGrace]

Girl just tell him you want him to fuck your ass. every person I've ever done anal with I've just told them during sex how i want it

[SarahsSummer]

You seem really mean? If the sex is so great, why do you want to hurt him, break his heart?

[Asker]

Read what I wrote to Shaft50 and to some Anonymouses

[SarahsSummer]

I'm sorry but you need therapy. To hold a grudge from a minor event as kids speaks to your mental instability and your desire through sex to hurt him back screams you may be a sociopath. Do you realize what you are doing is wrong, evil and unnecessary?

[Anonymous]

so why are u dumping him if he looks hot and the sex is amazing?

[Asker]

Because the whole thing of the two of us having sex is there because I want to dump him when he falls in love with me, and then he realize that all of the amazing sex we had is something he will never have with me again (nor with other people, cause they don't do it as well as I do it 😈) and something I will have with lots of other guys. I mean, I am hot, I can get almost any guy I want! The reason I am doing all of this is because I invited him on a date when we were kids and he stood me up even though he lied he would come. It took years to get over it and recover.

[1988fido]

U said ( kids ) Don't u think he might be trying to make it up to u? Or he truly changed? Or maybe he don't remember. , kids have no clue what relationship means also men mature late so don't punish him :/ find out if this is just sex for him. If it is then he deserve the punish I hate guys who sleep with women just for pure sex without any plans of future or feelings.

[Asker]

@1988fido just read my latest reply to Shaft50, I don't wanna repeat myself

[Imcmullan]

Lol
... i thought you wanted to give it to him. Not receive it... for its better to give than receive... lol... i love pegging a guy. 😍😍

[BuchitaBuchys]

Does he seem emotionally into you?

[Asker]

Probably... It doesn't matter.

[Asker]

Because the whole thing of the two of us having sex is there because I want to dump him when he falls in love with me, and then he realize that all of the amazing sex we had is something he will never have with me again (nor with other people, cause they don't do it as well as I do it 😈) and something I will have with lots of other guys. I mean, I am hot, I can get almost any guy I want! The reason I am doing all of this is because I invited him on a date when we were kids and he stood me up even though he lied he would come. It took years to get over it and recover.

[BuchitaBuchys]

Y'all were kids for fucks sake. I don't think you're over it and this is really cruel. I would advise against it.

[Asker]

I guess I should say I respect your opinion, but I disagree. And, yes! I am not over it! I never forgive! If you want to answer my question, you are more than welcome!

[BuchitaBuchys]

I'm not going to help you hurt him. I'm sorry :(

[TazWax]

While he is fucking you just say I want you in my ass.

[TiffyPuff]

When he penetrates your pussy, tell him "wrong hole." Then give him the 😈 smile

[Callieeee]

Just tell him to do it. After he's fucked you normal just moan and tell him to fuck your ass. I'm sure he won't object lol😄

[JoeCensored]

Try doggy style, then halfway through stop him, pull his dick out, and put it against your ass and start to push back.

[aftermath]

Lol leave a butt plug in the drawer where he keeps the toys or condoms or whatever so he knows you can take it in the ass. Should work no?

[Intraluminal]

When you get to wherever you're going to do it, take your clothes off and have one of those diamond studded plugs in your ass, winking up at him. Look back at him, and ask, "Well, aren't you going to take it out?"

[thewho1975]

Dya know if he actually wants to do it though?

[Asker]

Well I haven't asked him, but he really loves sex, why wouldn't he want it? It's every guys dream. I don't wanna ask him in advance and ruin the moment, I wanna ask him to do it "NOW", spontaneously...

[thewho1975]

Well i think you should casually hint to him first and see his response, because if he did say no in the heat of battle that would be a bit awkward

[ModernDayCrusader]

When you are fucking doggy style, tell him to stick it in your asshole instead, that should work

[Asker]

But I wanna say it first, so that he'll have time to think about it and be horny.

[ModernDayCrusader]

ok when you guys are doing foreplay bring it up

[Waffles731]

You are going for surprise buttsex,
its supposed to be a surprise
i.ytimg.com/vi/XnYuY6ySuJI/maxresdefault.jpg

[Yumix]

start fingering your ass while he takes you doggy, that shows him that you like your ass to be played with. usually, if he's into anal, he should start playing with it too or ask you about it... if he doesn't just ask him if he wants to fuck your ass

[Jj2016]

Mid fuck ask in to bend you over (he does bends you over) speed you checks and whisper sweetly but straight to the point I want your cock in my arse steering his cock towards your bum hole swollowing sliding it in... something like that?

[Anonymous]

I let my boyfriend put it there whenever he wants. It does take some cleaning effort though, but anytime if good!

[Anonymous]

Wait for bent over with a butt plug in your ass and on your ass write; "step one insert butt plug, step 2 remove butt plug, step three fuck ass"
I saw this in a porn video and thought it would be hot.

[Anonymous]

not all guys like anal
it can be messy :p