Best friend...should I?

[amandamanda]

So, my best friend (a boy) since like 2nd grade has always pretty much had a crush on me but i never really felt the same way (just not my type i guess or maybe we've just known each other for too long). But recently he had a pretty big personal tragedy (mom passed away) and hes been reeeeealy depressed and i feel awful for him. So, i was thinking maybe if i hooked up with him it would help make him feel a little better even for just that moment. I wasn't thinking like sex or anything but enough to have an orgasm for him i guess.

Id tell him its a one time thing and im sure hed really enjoy it but is it really bad to do cuz he might get feelings or whatever? my gut says its worth it but i dunno.

Update: I didn't mention originally but he kind of already knows i'm thinking of doing this cuz i asked him if it would make him feel a little better, so hes already kind of excited about it if that changes ur opinions

Update 2: It happened! Woohoo! lol

[Troy35216]

"i'm still not attracted to you and I'm not gonna have sex with you but I'll get you off one time cuz i feel sorry for you". how exactly is that going to cheer him up? your gut says it's worth it but my gut says it is a bad idea. if he is your best friend and he's depressed then he needs you to be his best friend be there for him not be his one time orgasm producer.

[amandamanda]

Well i guess cuz he's never had that from a girl before and i know how happy it would make him in the moment you know?

i wouldn't say it like that anyway lol the way u put it it sounds mean!

[Stryker125]

Bad idea. If he likes you as much as you say, then any kind of hook up will definitely mean more to him than it does to you. No matter what you tell him. You're his best friend, and he's hurting. He needs you as a best friend. Not to get him off. He's got two hands if he wants to get off. You just need to be there for him and let him know he can count on you.

[amandamanda]

Hmm these are good points. I guess tho it might be too late cuz i already asked him if thats something that might make him feel better even if it was a one time thing and he was like "UH, YAH!" So now its like if i got his hopes up and change my mind now its even worse

[amandamanda]

Also its not like im just getting him off like its a chore or something- i planned on making it really special, making it last a long time, and making sure it was something hed never forget

[SammieRose]

You are going to kill him if you do that. How will you feel if your crush starting going out with you and when you feel better he says: "Well, now that you are better, we should be friends again, i really do not like you that much."

Guess, you either cut his dick or get into a deeper depression. DO NOT DO IT!

[amandamanda]

Hi SammieRose- what do u mean 'you either cut his dick?'

I guess i'd be pretty upset if i started going out with someone and they dumped me cuz i'm feeling better, but i think guys are different - its more like what if you really wanted something for a long time and then you got it? For guys getting laid (or close to it in this case) is like the ultimate.

[Anonimi]

a couple of guys just told you its a bad idea, i will do the same, if that would happen to me, the friendship i had would be ruined after that

[SammieRose]

Hi SammieRose- what do u mean 'you either cut his dick?'

I guess i'd be pretty upset if i started going out with someone and they dumped me cuz i'm feeling better, but i think guys are different - its more like what if you really wanted something for a long time and then you got it? For guys getting laid (or close to it in this case) is like the ultimate.

Typo, i meant to say he not you

[amandamanda]

a couple of guys just told you its a bad idea, i will do the same, if that would happen to me, the friendship i had would be ruined after that

Well my (female) friends always tell me that theres no such thing as a boy/girl who are 'best friends' usually one wants the other or whatever. i dont know if thats true but i DO know he likes me like that and has for a long time.

I dunno i guess i already decided its gonna happen (and i asked him about it already) but maybe just want to know if theres a way to not make it weird after? I guess just talking about it here made me more sure of it lol

[Iron Man]

Nothing like a nice handy to help with depression, its a cure all.


But seriously, that won't help him. For a while, he will feel on top of the world, but reality will set in, and he will fall right back into that depression. If you really want to help him, be there for him, maybe even go on a date or something (if you are inclined to give him relief, and he is all for it, there has to be feelings on your side as well).

[Troy35216]

I guess i'd be pretty upset if i started going out with someone and they dumped me cuz i'm feeling better, but i think guys are different - its more like what if you really wanted something for a long time and then you got it? For guys getting laid (or close to it in this case) is like the ultimate.
i'm a guy and it's not different but idk why your even pretending to want advice since you already made up your mind and your gonna do what you wanna do. you told him you were gonna do it like half an hour after you asked for advice. i feel sorry for this guy for what your gonna be putting him thru especially on top of all the other shit he's got going on with his mom dying and everything.

[SammieRose]

Update: I didn't mention originally but he kind of already knows i'm thinking of doing this cuz i asked him if it would make him feel a little better, so hes already kind of excited about it if that changes ur opinions

Of course he is, in his mind, he's thinking he will make you love him, you will never leave him. How could you? right?

But the reality is that there is a really low chance you will fall for him, if you have not done yet. And even if he later guilt you into staying with him, it will be an unhappy relationship for the both of you.

He is emotionally unstable right now, do not give him false hope!

[Anonimi]

well if you have too..... weird it will become, i think, i would love an update after

[amandamanda]

Nothing like a nice handy to help with depression, its a cure all.


But seriously, that won't help him. For a while, he will feel on top of the world, but reality will set in, and he will fall right back into that depression. If you really want to help him, be there for him, maybe even go on a date or something (if you are inclined to give him relief, and he is all for it, there has to be feelings on your side as well).

Haha who said it would be just a handy?

I think a date is a great idea. I wouldn't say there's NO feelings on my side, just i guess i don't look at him that way. But there is something that is making me wanna do this and even if its a longshot for it turning into more i KNOW he'll enjoy the moment

Of course he is, in his mind, he's thinking he will make you love him, you will never leave him. How could you? right?


I think he's thinking in his mind 'this is gonna feel awesome!' if i know him well

well if you have too..... weird it will become, i think, i would love an update after

Haha I'll let ya know

Next time combine all your posts instead of double posting. -Jordan

[Gandalf]

So, my best friend (a boy) since like 2nd grade has always pretty much had a crush on me but i never really felt the same way (just not my type i guess or maybe we've just known each other for too long). But recently he had a pretty big personal tragedy (mom passed away) and hes been reeeeealy depressed and i feel awful for him. So, i was thinking maybe if i hooked up with him it would help make him feel a little better even for just that moment. I wasn't thinking like sex or anything but enough to have an orgasm for him i guess.

Id tell him its a one time thing and im sure hed really enjoy it but is it really bad to do cuz he might get feelings or whatever? my gut says its worth it but i dunno.

Update: I didn't mention originally but he kind of already knows i'm thinking of doing this cuz i asked him if it would make him feel a little better, so hes already kind of excited about it if that changes ur opinions

I urge you not to do this, he's unhappy and that's a natural reaction to a family members death, he needs to focus on that rather than possibly becoming confused/conflicted or filled with any regret at such a sensitive time.

[Sleepwalking]

This seems like a horrible thing to do.
Sexual favors won't make him feel better about his mother dying. You should be there for him, but doing this seems wrong.
I think he could get emotionally attached to you, regardless of your initial intentions.

[unnamed94]

its a terrible idea imo. he has feelings for you and you think thats a way to cheer him up? he probably sees that as a great opportunity (who wouldnt like for that to happen with his crush) but im sure thats gonna make him feel bad after. what he wants is for you to like him to be his gf or whatever not just a one time thing like that to cheer him up because hes depresed. i would feel like shit if it was me. if you went on a date with him im sure that will be way better for him, just dont make it all like im gonna satisfy you and nothing more.

theres no way it wont be weird with him later btw

[AvMan]

I don't know... Is it really worth it?

[lorddia]

I got a question for u ,imagine that after you got him laid one day out of the blue he asks you to do it again ! what will you do then ,would you tell him that you can't because you don't feel the same way(sexually ) about him?or would you do it for him .case if you do it again then you r ruening your friendship ,and if you don't you gotta tell him why you did it the first
time and that will upset him, and believe me I am a guy , the idea that the only thing that we care about is getting laid is just not true !we care !and if a friend of mine had done that to me i d never talk to her again then!

[amandamanda]

Soooo...it happened!!

It was pretty crazy, i gotta say. Boy was he happy, and BOY was he drained afterward. Im not going to get into details as im sure it's against the rules here but happy to tell over PM if anyone wants. Not sure what it means for us after this but i guess i can say i'm open to doing that again cuz it was pretty exciting and it was kinda fun making someone i care about soooooo happy. Thanks everyone for the advice and i guess im just not sure what it meansss!!

[unnamed94]

well my advise was for you not to do it but well, now that its done and you seem open to do it again just be careful. if you dont seem him as more than a friend then he might develop stronger feelings for you if you keep doing it with him and that wouldn't end well.

[Swa19]

My view is definitely not the same as everyone here. If hes going through a hard time regardless, i think that if just for 15, 30, 45 mins or so of just getting away from your problems helps. It helps me just to escape for a while to realize how much being happy is really worth! I'm not saying what happened to him is something to take lightly. I have NO idea how he feels. But you need to work on getting better to get better. And maybe, JUST maybe will a little taste of happiness will urge him to try to become happy again.

But you have to make sure he knows WHY this is happening. I understand this already happened once but if you haven't you NEED to talk to him and say that you are doing it to try to give him something to be happy about during a hard time. and if you enjoy it too, tell him. It will make him feel worth more. but make sure you have a thorough conversation on why it happened and dont lie to him for his sake. I have been in "similar" situations and if you need any more advice about how to go about this then feel free to PM me :)

[amandamanda]

My view is definitely not the same as everyone here. If hes going through a hard time regardless, i think that if just for 15, 30, 45 mins or so of just getting away from your problems helps. It helps me just to escape for a while to realize how much being happy is really worth! I'm not saying what happened to him is something to take lightly. I have NO idea how he feels. But you need to work on getting better to get better. And maybe, JUST maybe will a little taste of happiness will urge him to try to become happy again.

But you have to make sure he knows WHY this is happening. I understand this already happened once but if you haven't you NEED to talk to him and say that you are doing it to try to give him something to be happy about during a hard time. and if you enjoy it too, tell him. It will make him feel worth more. but make sure you have a thorough conversation on why it happened and dont lie to him for his sake. I have been in "similar" situations and if you need any more advice about how to go about this then feel free to PM me :)

So funny cuz i pretty much had that exact conversation with him yesterday! That with all he's going thru, the LEAST i can do is give him something to be happy about and yah its definitely something im enjoying giving him too because like no joke ive never seen a guy enjoy it like he does (not like ive been with lots of guys but still....) And were gonna do it again this week when my parents go out of town so we'll have even more time to build it up!

Also I can't send PMs yet so maybe either PM me or tell me here what ur situation was and how u dealt with it?

[Shortie]

I can see why you would want to do it Amanda and I think it's pretty special of you. So long as you love him (as best friends) and you're both matured enough to handle it and it won't ruin a friendship, those are the things id consider, then I don't see a problem.

[amandamanda]

I can see why you would want to do it Amanda and I think it's pretty special of you. So long as you love him (as best friends) and you're both matured enough to handle it and it won't ruin a friendship, those are the things id consider, then I don't see a problem.

Thanks Sophie! i figured another girl would understand! haha

yah I care about him a LOT and definitely love him as a best friend and he's always been there for me. Gosh to think of how many times hes been so patient and listened to me blab on and on about guys or whatever.

And when i see him so sad (hes usually a happy person) i just think of what might make him happy. i never had someone close to me pass away but i see that its reaaly hard to take his mind off of it. But i can already tell from when i did it for him a few days ago that once that special buzz starts, it's impossible for him to think of anything BUT how good he feels. I can like literally see the sadness and frustration melt away from his face.

As his best friend its so awesome to see him get to that place where hes smiling (even laughing!) with me again, even if it's just for the few hours that it's happening. so i truly do get a lot out of it too and i told him he shouldn't look at this as a favor, but something i WANT to do so that he'll get to be happy for a little bit. and now he knows its happening again this weekend so he has something to look forward to and get excited about. So u can see how at least up until now, i'm really happy i made this decision! :)

[Shortie]

Thanks Sophie! i figured another girl would understand! haha

yah I care about him a LOT and definitely love him as a best friend and he's always been there for me. Gosh to think of how many times hes been so patient and listened to me blab on and on about guys or whatever.

And when i see him so sad (hes usually a happy person) i just think of what might make him happy. i never had someone close to me pass away but i see that its reaaly hard to take his mind off of it. But i can already tell from when i did it for him a few days ago that once that special buzz starts, it's impossible for him to think of anything BUT how good he feels. I can like literally see the sadness and frustration melt away from his face.

As his best friend its so awesome to see him get to that place where hes smiling (even laughing!) with me again, even if it's just for the few hours that it's happening. so i truly do get a lot out of it too and i told him he shouldn't look at this as a favor, but something i WANT to do so that he'll get to be happy for a little bit. and now he knows its happening again this weekend so he has something to look forward to and get excited about. So u can see how at least up until now, i'm really happy i made this decision! :)

Haha I understand exactly what you are doing and why you want to, I think it's very nice of you. Obviously you're happy, he is happy, there is no harm.

[Swa19]

Just don't let it go too far. I know it can be weird if things are going down and he starts saying he cares for you and you being in a position of not wanting to let him down but not wanting to lie. He will forgive you if you tell him the truth, but for his sake don't get his hopes up falsely just to spare an awkward situation

[PinkFloyd]

So, my best friend (a boy) since like 2nd grade has always pretty much had a crush on me but i never really felt the same way (just not my type i guess or maybe we've just known each other for too long). But recently he had a pretty big personal tragedy (mom passed away) and hes been reeeeealy depressed and i feel awful for him. So, i was thinking maybe if i hooked up with him it would help make him feel a little better even for just that moment. I wasn't thinking like sex or anything but enough to have an orgasm for him i guess.

Id tell him its a one time thing and im sure hed really enjoy it but is it really bad to do cuz he might get feelings or whatever? my gut says its worth it but i dunno.

Update: I didn't mention originally but he kind of already knows i'm thinking of doing this cuz i asked him if it would make him feel a little better, so hes already kind of excited about it if that changes ur opinions

Well If you're not interested in a real relationship with him, you could be friends with benefits. This allows you to do whatever is the one time thing (probably a hj) more than once. Of course after a while, you will probably end up in a relationship with him one way or another. I mean this guy is probably dying for what you have planned. Like most guys, he's gonna want more. That could be anything up to sex. If you are sure that you want this to be only a one time thing, then I'd suggest not doing it. You will break his heart. Of course, you already offered to do it so from my point of vies, you are already locked in. I mean I guess you should make sure that it's a one time thing only.

[CharlieHorse]

Honestly, I know you're trying to be thoughtful, but that sort of affection sounds sort of artificial.
You shouldn't do that just to cheer him up, you should do that only if you love him and want to be serious with him.
Otherwise it makes you sound manipulative in a strange sorta way. You'll probably lead him on, and if you aren't into him like he is into you, it night hurt him. I know you have good intentions, but I don't think that doing that will help him that much...

[amandamanda]

Personally I see nothing wrong with it as long as you're on the same page and understand BOTH OF YOU that you're just friends fooling around for the fun of it

Aww thanks. So far its going good!

[Redrocket]

I think it's a bad idea he might start to
really get attached to you. When the one
Time thing is done it will break his heart
and he will suffer a heartbreak I know
because I been there!

[funyun4282]

Is it a relationship that is strictly focused on him? Do you get any pleasure out of it?

[dvd333]

I wouldnt lead him on if i were you... hes going to want to return the favor and you probably wont want to. Id personally feel bad since its kind of equivalent to pity sex... guys want more than an orgasm. We arent hypersexual emotionless beings. Consider dating him or opening up emotionally to him. I feel like your walking on egg shells right now only because so much can go wrong. Email me what exactly you did. Certain things are more intimate than others and i dont want this poor guy to get hurt...

[amandamanda]

Is it a relationship that is strictly focused on him? Do you get any pleasure out of it?

I get pleasure out of giving him pleasure, if that makes sense. I like it when he's happy.

[funyun4282]

Is it strictly a one sided sexual thing? Do you let him reciprocate? Or is it a strict you focus on him relationship?

[funyun4282]

Im just curious because he may end up wanting more out of the friendship like being able to do things to you. How will you handle that?

[digzchickz]

i really dont see nothing wrong with it as long as he knows the nature of the relationship, i mean i dont necessarily think that you need to be in a relationship to do sexual stuff. i mean i wouldnt mind a friends with benefits thing if i didnt have a gf. i mean when it gets down to, sex just plain feels good and 2 people can have a mutual interest in the physical feeling.

BTW did you have the kitty face on when you did it? That would have been awesome.

[amandamanda]

i really dont see nothing wrong with it as long as he knows the nature of the relationship, i mean i dont necessarily think that you need to be in a relationship to do sexual stuff. i mean i wouldnt mind a friends with benefits thing if i didnt have a gf. i mean when it gets down to, sex just plain feels good and 2 people can have a mutual interest in the physical feeling.

BTW did you have the kitty face on when you did it? That would have been awesome.

Aww thanks. FWB is so far what it is and going well (its been 3 times weve fooled around now). Lol you think a guy would want to hook up with a girl with kitty makeup / costume on?? Do tell!

Is it strictly a one sided sexual thing? Do you let him reciprocate? Or is it a strict you focus on him relationship?

Im just curious because he may end up wanting more out of the friendship like being able to do things to you. How will you handle that?

I think hes always wanted more so no change there. and lets see where it takes us...i tend to get attracted to guys that arent great for me so maybe this is a good start!

[dvd333]

Aww thanks. FWB is so far what it is and going well (its been 3 times weve fooled around now). Lol you think a guy would want to hook up with a girl with kitty makeup / costume on?? Do tell!
A guy definitely would in my opinion. Haha




I think hes always wanted more so no change there. and lets see where it takes us...i tend to get attracted to guys that arent great for me so maybe this is a good start!

So far so good! Be happy that hes a great guy.

[amandamanda]

So far so good! Be happy that hes a great guy.

Yep! And he's getting 'rewarded' for being SUCH a good guy =)

[dvd333]

Yep! And he's getting 'rewarded' for being SUCH a good guy =)

Thats a good way to put it. Haha. Im glad you both are happy. Just be sensitive of each other's feelings

[dvd333]

As for the whole kittie thing,habe fun with it. Im sure no guy would mind. Haha

[funyun4282]

You say you get attracted to guys who arent great for you? So is this guy not good for you? or just the opposite?

[amandamanda]

Thats a good way to put it. Haha. Im glad you both are happy. Just be sensitive of each other's feelings

Yah, i mean the whole idea of doing this was that i saw what his feelings were etc. and about being sensitive, might not be what you meant but boy do i have to be sensitive to his 'feelings' to make sure it goes on for a long time ;) haha

As for the whole kittie thing,habe fun with it. Im sure no guy would mind. Haha

haha maybe i'll try it! mraw!

[amandamanda]

You say you get attracted to guys who arent great for you? So is this guy not good for you? or just the opposite?

This is the opposite. He's probably good for me so originally i didnt get attracted to him

[dvd333]

Yah, i mean the whole idea of doing this was that i saw what his feelings were etc. and about being sensitive, might not be what you meant but boy do i have to be sensitive to his 'feelings' to make sure it goes on for a long time ;) haha



haha maybe i'll try it! mraw!

Hahaha. You should try a lot of things. Just have fun with it!

[funyun4282]

oh, maybe the fooling around will get you attracted? You must have a physical attraction at this point.

[amandamanda]

oh, maybe the fooling around will get you attracted? You must have a physical attraction at this point.

Maybe so =)

Hahaha. You should try a lot of things. Just have fun with it!

Yah i can get pretty creative with it i think! I already have a rly silly idea ;)

[dvd333]

Maybe so =)



Yah i can get pretty creative with it i think! I already have a rly silly idea ;)

Email it to me. Dont be afrajd to try new stuff either. Haha

[amandamanda]

Email it to me. Dont be afrajd to try new stuff either. Haha

Oh heck i'll post it: kitty costume, thong with a tail built in, paint with pink body paint the letters "ME" on my left butt cheek and "W" on my right butt cheek =)

Anyone get the joke? :P

[funyun4282]

haha! that will get him going for sure.

[dvd333]

Oh heck i'll post it: kitty costume, thong with a tail built in, paint with pink body paint the letters "ME" on my left butt cheek and "W" on my right butt cheek =)

Anyone get the joke? :P

Hahaha!

[amandamanda]

Hahaha!

haha! that will get him going for sure.

Seee? I can be creative when i wanna!

[dvd333]

Seee? I can be creative when i wanna!

Well keep it going and he'll have a good time!

[digzchickz]

Aww thanks. FWB is so far what it is and going well (its been 3 times weve fooled around now). Lol you think a guy would want to hook up with a girl with kitty makeup / costume on?? Do tell

heck yeah actually that sounds pretty dang hot. haha and yeah the costume idea sounds pretty sweet... just take it easy on him cuz hes still pretty new at this, get him too excited and he'll be done before he starts. :)

[Amber Bi]

I totally get the joke...
I bet he'll love it.
you sound like a great friend that only wants to help him out.
Hope it all goes well for you guys.
AND i love love love ur ideas !! hahaha

[Wanderer_]

What did u do? Go all the way?

[Stronk Serb]

*looks at the upper posts*
What in the name of...

Back on topic, sounds that you are doing great. Keep it like that.

[sambeans]

As long as it hurts no one I say go for it.

[Wanderer_]

I think it's very compassionate

[Synyster Shadows]

sounds like things are going great. Keep it that way.
that kitty costume is soo damn cute. I'd love it if I fooled around with a girl in that costume :3

[amandamanda]

sounds like things are going great. Keep it that way.
that kitty costume is soo damn cute. I'd love it if I fooled around with a girl in that costume :3

I think it's very compassionate

Aw thanks guys...yeah he's doing a lot better and has a gf now, which I'm really happy for!

The kitty costume WAS fun haha

[Synyster Shadows]

Aw thanks guys...yeah he's doing a lot better and has a gf now, which I'm really happy for!

The kitty costume WAS fun haha

Good to hear. That's great.
I'm sure it was. you look cute in it. ;)

[LunarScorpio]

Glad it went well, but do be careful about things like this.

[amandamanda]

Good to hear. That's great.
I'm sure it was. you look cute in it. ;)

Aw, thanx! It got totally ruined tho :P

[Wanderer_]

Aw, thanx! It got totally ruined tho :P

ruined how :D ?

[amandamanda]

ruined how :D ?

haha no comment :lol:

[Wanderer_]

haha no comment :lol:

Pleeeeease PM me about that !
<3

[chezhans]

I should send this story to my female best friend...she has splitting parents but she doesn't like me that much despite it seriously being a "love in progress" affair on this end ahaha :)