So, I made a post a while ago about a guy I'm friends with. We aren't seeing each other, but the idea of FWB has been thrown around once or twice. This is extremely embarrassing and maybe not even the kind of post that's welcome on this forum, but I really had no one else to ask.

He's asked numerous times to...ahem...finger me, for lack of better explanation. I'm not 100% on board with it just yet, but it's a possibility. My fear is, how the **** are we going to pull that off without me looking like a giant white whale? Are there any good positions anyone can reccommend for the bigger girls? Ideally, I'd like to be wearing a skirt and not have to take too much off, but I don't know if that's like...proper sexiquite? lmao.

I ask because the first time we talked about it we were sitting on the couch, and that doesn't really leave much room to do anything, and getting in the bed seems to awkward at this point in the friendship. I'm nervous that if we're sitting, he'll reach down there and feel my STOMACH first (you know, that lovely, hangy bit of stomach right above the mons pubis?), and I'll be totally mortified. And if I'm laying, what if my thighs are too thick? Will it be awkward if I have to open my legs?

I cannot believe I just posted this, but I'm actually kind of excited about this because I've never done any of it before. I don't think I'll want to have SEX for a while, but this I'm more open to.

If you're nervous, try it w/o the lights & with a couple of candles burning. The "romantic glow" hids numerous flaws.

Also--he probably won't care

Of course, if you're not comfortable for other reasons, then I say LISTEN TO YOUR GUT!! Don't have sex with ANYONE you're not ready to have sex with....for any reason!

This is kind of cute.

Lying down really has to be best, simply because it allows you to enjoy the experience more.

I would say try not to worry about your thighs, relax them, try to share the pleasure without feeling stressed.

If you are ready to share this with him you will set aside your qualms and immerse yourself in the moment.

I know he probably won't care, but the thing is I'm 22, I want some sort of experience. I don't really want to have sex right now, but I really do want to do SOME kind of exploring. And he's a really nice guy and I know he'd take it slow and stop if I said to.

Plus he's skinny as a freaking rail LOL so that's probably another reason I'm a little more nervous. I'm getting a little more confident as time goes on though, my stomach is definitely flattening out which is nice.

This might not be what you want to hear and this is purely my opinion, but coming from an old(er) lady who's been there done that, that sounds degrading. I know it sounds exciting for you right now, and I'm no prude by any stretch of the imagination lol, but getting "fingered" isn't the most intimate sexual act out there.

If it were me and thats all that happened, and I'm not even referring to actual intercourse (i.e. no kissing, no making out etc). I would feel dirty afterwards.

Again, just my personal thoughts. Just make sure you think through whatever you decide.

Good luck.

Fingering isn't that great for a lot of women. Make sure he doesn't start off with too many fingers - you're small so one will probably be more than enough. A lot of dudes watch porn and think it's totally OK to jam two or three in there from the get-go.

He knows what you look like clothed so I'm sure he's imagined and somewhat accurately visualized you naked. Don't be self conscious about it and just have fun - but be prepared for him to want something in return. Are you ready for all this?

I know your not going "that far" yet, but just remember something I told my daughter. Think A LOT before you decide. Its a gift that you can't get back, ever, once it's given. And it truely is a gift, when you have that special person to give it to. I know it probably sounds corny and old fashioned but your first time really is a once in a lifetime thing. Take care.

Have you done self exploration? I think that would be your first step. Obviously people feel differently about casual encounters. Some are fine with it. Others are not. I think it can bring a strong emotional attachment though or at least that is my experience. I had a good friend in college who wanted to be friends with benefits. In the end, I decided against it. We had a great time together and quasi dated for over a year. Nothing sexual happened between us and it didn't need to.

I also had my first sexual experience when I weighed 350 lbs. if a guy cares about you, then your weight really doesn't matter.

This reminds me of this:

Reverend Boteright: You know, Rory, being a young lady comes with many gifts. Your virtue, for example, is a gift, a precious gift, possibly the most precious gift you possess.
Rory: Uh huh...
Reverend Boteright: You want to give this gift very carefully. It is a gift you can only give to one man. Once you give it, it's gone, you cant re-gift it. If you give it away too soon, to the wrong man, then when the right one does come along, you have no gift to give... you'll have to buy him a sweater. Do you understand what I'm saying?
Rory: No.
Reverend Boteright: Think long and hard about when and to whom you want to give the ultimate gift you have to give away.
Rory: Oh.
Reverend Boteright: Yes.
Rory: Oh dear...
Reverend Boteright: Oh dear indeed.
Rory: Um, well, listen, reverend, I really appreciate you taking the time out of what I assume is a busy day to come here and talk to me about... all of this, but I'm afraid the ultimate gift ship has sailed.
Reverend Boteright: What?
Rory: A while ago... it's probably in Fiji by now.

http://www.imdb.com/title/tt0588226/

-----------------------

I know its from gilmore girls, lol, but its true. Once you go down that path, once you "give that gift", there is never any going back. EVER. Make sure you are ready to go. And that you're "all packed up" if you know what I mean. A lot of times one thing, ie: fingering, leads to another... I'd want you to be prepared for.. another.

Good luck.

Be aware that something as "small" as that often leads to full blown sox. Once you're in that vulnerable position, the neck kissing begins, it goes lower, and you're there before you know it.

Also, as Krampus said, he will expect something in return and we all know what that something is... do you want to do that just with a "friend"?

I'm 28 and definitely not "old" but I'm with Mammasita on this. Really think it through. I understand you want to start experiencing things but it should be with someone you really care for and really cares for you. If you think back on your first time or even first experiences, don't regret them!

Honestly, I've never been a "friends with benefits" person. I can't enjoy any experience with them unless there are really deep down emotions tied to it. I cannot separate sex and emotion.

Are you not open to a relationship with him or is he not interested in dating you? If it's the latter, my question would be why is he OK with sex but not a relationship? This may not be the case but it's something you should know the answer to and be comfortable with.

I agree with pretty much everything krampus said.

And honestly, guys always seem to think they're awesome at this kind of stuff.. However, most of the times, they just really suck LOL Try to not build too much expectations about the first encounter.

I'm kind of torn, because If I get into a serious relationship, be it with him or someone completely different, I don't want to know absolutely nothing. And I mean NOTHING. I thought it wouldn't be such a bad idea to try things out with a guy I feel safe around, and that if I just didn't have sex (and trust me, I won't if I don't want to, and I don't want to right now), it wouldn't be that big a deal. And honestly, I guess the reason I'm okay with it is because I literally get no pleasure out of penetration of any kind, so it doesn't seem like something so special. I would probably be okay learning to give a blowjob too, because I have no freaking clue how to go about that, even after watching tons of porn.

As for what you asked, MuffnTop, I'm not sure. I'm not really looking for a relationship right now, and as far as I know, he isn't either. We're just friends, and our friends have been trying to set us up. But now I'm wondering, why sex and not a relationship? Maybe because I've said I'm not looking for one?

You seem to be asking several things there.

1) FWB -- if you are sure this is the type relationship you want with this person, that's up to you. But don't go there if you really aren't sure just because HE wants to. Some people can separate sex from emotional bonding, but some cannot. Talk about what that MEANS to each of you. Because what one person calls FWB may not the same definition as a another.

I had a FWB and we had the agreement of safe sex always and though we were not exclusive, I did expect to be told of any OTHER FWB or lovers in the picture so I could make fully informed decisions.

2) Wear whatever for clothes. That can be lifted up or come off or whatever. That's minor.

I'd be more concerned about health hygiene. Digital sex still requires hygiene -- so make sure fingernails are trimmed and filed, and gloves handy.

Even if this "only" digital sex or only a ONE TIME thing -- do the sex talk. How many partners before you? Any concurrent FWBs/lovers floating around? Health history? STDs? Attitudes about birth control? Accidental pregnancy? Who pays for what? When was your last screen and can I see a copy? Everything like that.

Because if digital sex should lead to other things in heat of the moment even if you don't think it will or even later down the road it leads to a longer thing than one time... I think it's better to know where we stand on things NOW than end up in a bind later because we didn't stop to have the talk!

When I was single I also had a small secret savings acct to pay for EVERYTHING myself. I expected to split the costs halfsies for whatever was needed but I wasn't about to be left in a bind just because HE was broke and couldn't buy condoms or something!

I'd suggest self exploration too. That IS sexual experience. A lot of what we teach our lovers comes from knowing what we do/do not like! Your partner will tell you what works or doesn't for them. Just ask.

This digital sex request at this stage of the relationship when you are only friends and you haven't even had a real date seems premature to me, if not bordering on fresh. Does he ask all his women friends this? Just like that? "Hey can I finger you?" Jeez. Some friend!

Why the digital sex? Why not a date? Just kissing and hugging? Have the sex hygiene talk and perhaps kissing and over the clothes petting stuff. Not jump into digital sex too fast. Because honestly? Having the sex talk alone is sometimes enough litmus test to see how respectful/honest/clean this person is.

I'm not knocking FWB -- I just find it weird to want to START there, and start with digital sex. It's like he's asking that because he knows you'd turn down full sex? Wassup with that? Sheesh.

In my experience, we were friends. Then some dates. Then the talk, and we were lovers. It was FWB because I didn't want to stop dating others and be exclusive. I wanted an open relationship at the time. He was ok with that.

I enjoyed his company, but I still wanted to look around. He was free to date also, but the agreement was safe sex, and I don't need to know who else you are dating unless it's looking like moving to lover level too. Then just tell me so I can make a choice if I'm still in or not. That was fair enough for both of us.

But the point is... we DID talk it out and figure out where we stood relationship wise, health wise, etc.
So? You don't want an "exclusive, closed relationship" right now.

That doesn't mean an "open relationship" format doesn't need to be discussed, negotiated, agreed to first before jumping into bed for digital sex!

Even a "one time thing" requires some discussion and negotiation so it is respectful, safe and pleasant for all.

Like I said... there's being respectful about it (whatever type IT is) and then getting kinda fresh.

A.

This is a matter of my opinion because I am experienced with this...

From the sounds of it you're not comfortable enough with yourself and to be honest in order to have FWB you need to be pretty sure with yourself in order for it to work because if you're not it becomes too messy and complicated. The point of FWB is not having feelings or thoughts towards the other person or them having feelings towards you. It's just sex. If you can't make it just sex, than I don't suggest doing it. But one way to work towards that is one Liquor always helps if your really sure this is something you want to do. Also wear a skirt or wear a baggy shirt so your not completely naked. Lights out completely is always good to. Do it in the bed, do it everywhere. It only becomes awkward when you develop feelings and ruin the whole FWB thing.

I once had a deal with a guy who was my friend to be FWB it was great, we set out rules for it...another thing you need rules. Everything needs rules. so talk to him about it. Don't just ASSUME you both are on the same page with everything because you probably aren't.

1) don't get attached
2) don't tell me about your other relationships
3) DON'T GET ATTACHED! Feelings are a NO NO!

Well he broke the rule and got attached in the end he got hurt. The second feelings start coming involded and only ONE of you has them. It has to stop. because trust me if you start to develop feelings and he doesn't feel the same for you...in the end it's your self esteem that may get ruined because after ever encounter you have with a guy who you feel for and who feels nothing for you, make you feel like ****. Not him.

I don't know I think you really need the mentality it for it, because it can be a real eye opener if you're not prepared. They say sex can be pretty vulverable and put you in a vulverable place. You need think whether it's really the best thing for you "experienced, or not".

Good luck, always do whats best for YOU in the end. If one minute you decided with him you wanted to do it, and the next don't. Then don't. If he gets mad well so what, he's just a guy and theres plenty more out there!