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» Scarleteen Boards: 2000 - 2014 (Archive) » SCARLETEEN CENTRAL » Sex Basics and Sexual Health » Fingering advice & awkward boyfriend

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Author Topic: Fingering advice & awkward boyfriend
Member # 109303

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Hi ya erm, I've been with my boyfriend just under five months and I think about a month and a half/two months ago we started doing stuff together. We took it pretty slow as both of us are virgins and have body confidence issues. It started with dry humping and kinda just went on from there, but he was the first to have anything like, done to him? It started with a hand-job and now we've done everything but sex, and we've come pretty close - we even always have a condom on standby. The main two that we do are blowjobs and fingering, as a) he doesn't really like handjobs all too much and b) he can do them himself. I'm getting pretty used to giving BJs now, however as I'm quite new to all this there are still lots of questions circulating in my mind (apologies for the oncoming essay..)

1. Once or twice I've noticed a horrible tangy/metallic tasting thin liquid on his dick before anything has even started. Obviously we're both 'in the mood' and do simple stuff (rubbing, kissing, etc..) to get eachother more into it - could it be anything to do with that?! He's a pretty clean guy so I'm legit praying that I'm not tasting remnants of urine.

2. I know you're meant to like, deep throat and stuff, just cause it's part of it, but I've not got a great gag reflex. Usually I'm fine but the last time I was pretty bad and once I finished my eyes were watering so bad that my eyeliner had ran down my face and I was nearly throwing up - I tried to last long enough to finish but I had to stop, I didn't wanna be sick! Please tell me it will improve (my gag reflex)?!

3. He's not a very 'wild' guy and this is literally the only way I can get him, as previously mentioned he doesn't like handjobs and unlike me having 'sensitive' areas or just general likes (neck, behind ear/earlobe, licking, biting, the usual stuff - or so I'm told), he's got nothing. It's so frustrating because he can get me so easily and I want to be able to get him back without nearly being sick every time!

4. He doesn't like to cum. He's precum once or twice and he likes to get close, but it's never happened. I try telling him that it's healthy and he needs to from time to time, but I know for a fact that since we started doing stuff and I think a while before that even, he hasn't masturbated. Is it bad that I want him to cum? And is there any way at all I can get him more comfortable with the idea of it? Like he always stops me when he's right on the edge and I soooo badly want to keep going but I don't want to upset or annoy him.

Okay, now that whole ordeal is over with, onto the other part. I only let him go down on me for the first time verrrrrrry recently as I don't shave very often due to a) inexperience/knowledge of even HOW to properly, b) slight ingrown hair issue and c) just general confidence issues. But he's a nice guy, he's not some egotistic nymphomaniac and he doesn't mind a bit of hair (unless it's oral, he won't do that unless I've freshly shaved). I feel bad because he really doesn't know what he's doing, I can't help him because I just won't masturbate, I hate the idea of it (similar to him I guess) and because although he's not my first boyfriend, he's my first SEXUAL partner - so I'm clueless too. I'm a complete closet geek so sometimes I'll build up my confidence and search the deepest realms of the internet for videos and columns on "how to ........." just so I can give him some advice. He kinda gets better each time with experience but tbh all he does is rub, no insertion. This is gonna sound SO stupid... but he doesn't even know which is the right hole. The other day (same day as the nearly vomiting issue, so not a great day!) he'd pretty much got me wrapped around his pinky and I told him to extreeeeemely gently try to insert one finger. He did, and it stung. Like hell. Like REALLY BAD. I told him to keep going, and asked if it felt right (to which he said yes), and after a while it started to feel a little better - although I was still in pain. Because of the pain my mood was fading fast, so he did his best to get my mood back up again, but when he went to put his finger back in it hurt 100000000000x more than it did the first time! I'm so annoyed, it's not like I have a problem with getting 'in the mood' like I go crazy and I don't even need him near me for it to happen (yay hormones *not*), so why did it hurt so much?! Is he in the wrong hole or is my body just a death trap?! I can't even deal with one finger inside, let alone two! We're the only virgins left out of a large friendship group and I spoke to my closest friends about it and neither of them felt pain so whaaaaaaaat is goooooooiiiiiiing onnnnnnnnn?!?!?!? Help please [Frown] [Confused]

(sorry for the length... I got an A* in English. I can talk/write for h o u r s)

Posts: 2 | From: england | Registered: Jan 2014  |  IP: Logged | Report this post to a Moderator
Sam W
Scarleteen Volunteer
Member # 108189

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1) Using a condom will help with this, and it will be safer as well

2)You are not meant to do anything when it comes to oral sex (or any kind of sex). If it's uncomfortable for you to push his penis past a certain point, then don't do it.

On the other subjects (what gets him going, how comfortable fingering is), the only way for you or him to know what feels good is experimentation, exploration, and communication. You are both new to this, so there is going to be a learning curve, and accepting that may help make you feel less awkward. But neither of you is psychic, so talking about what feels good/not good is really important. So, when he's going down on you? You can help him by saying "try moving your tongue up a little" or "that motion feels good." It might also be fun for you two to try exploring his body (if you haven't already) to see if he has any undiscovered hot spots.

As for the painful manual sex, I think these articles will be a good starting point:
From OW! to WOW! Demystifying Painful Intercourse

Lubricant (Not Diamonds) Is A Girl's Best Friend

Be a Blabbermouth! The Whats, Whys and Hows of Talking About Sex With a Partner

[ 01-09-2014, 10:17 PM: Message edited by: Sam W ]

Posts: 1292 | Registered: Aug 2013  |  IP: Logged | Report this post to a Moderator
Member # 109303

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Is a condom really needed for blowjobs? He doesn't cum at all, and he's never been with anyone but me. He barely even pre-cums. And even just lightly moving his penis further into my mouth can make my eyes water, he's not exactly a huge guy - I'm pretty happy with his size (although he's not). And thank you for the articles, I'll read them now [Smile] I think this is the first site I've found that's actually useful, instead of just having to endure muted porn and then clearing my internet history.
Posts: 2 | From: england | Registered: Jan 2014  |  IP: Logged | Report this post to a Moderator
Robin Lee
Volunteer Assistant Director
Member # 90293

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As Sam said, if anything about oral sex is physically uncomfortable for you, or if you just aren't into it, you don't have to do that thing. There's no one way to engage in oral sex, so talking with your boyfriend, sharing what you both like and find comfortable, and coming up with ways to do things that work for both of you is the soundest way to go about this.

From a safer sex perspective, yes, condoms are necessary for oral sex. Transmission of some STIs is through skin-to-skin contact, so the presence or absence of semen or pre-ejaculate doesn't make much of a difference.

Have both of you gone for STI testing? It's sound for anyone, no matter whether they've had previous partners or not, to get tested for STIs as part of their regular sexual healthcare.

Here's some information about safer sex: Safe, Sound & Sexy: A Safer Sex How-To

Have you been able to talk with your boyfriend about any of this yet?


Posts: 6066 | From: Washington DC suburbs | Registered: Dec 2011  |  IP: Logged | Report this post to a Moderator
Member # 109305

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remember that you are awakening feelings in him that he didn't
Know he had until now and those feelings are so intense that it scares him a bit.Now regarding line one of your post , when the male is sexually aroused, semen from his prostate and Cowper fluid from the Cowper gland line his urinary tract in preparation for ejaculation . Some of this clear sticky fluid may come out the tip of his penis. But it is here that we run into the condom issue. From the point of view of those chatting with you here, your boyfriend may have had another sexual partner and is not telling you. He may have incurred a bacterial or viral infection in his penis that is causing that discharge, an infection that can live in your throat. A condom is a barrier to that . It"s highly unlikely to be urine as that flow is blocked by an erection.
To say that he doesn't" like to cum seems odd since that is the most ecstatic moment. I suspect he feels very self-conscious about possibly offending you or grossing you out in some way and that kind of anxiety he may need to trust you more. The key of course is to communicate with him. Communication is the biggest problem solver. If you"re shy about playing twenty questions , try also to observe him, does he get tense ? Is he locking up his breathing when you do certain things,? Is he running to the bathroom or getting the shakes ?

P.S porn is not an accurate source for much and it tells you little of what is going on in the mind

Posts: 1 | From: Colorado | Registered: Jan 2014  |  IP: Logged | Report this post to a Moderator
Scarleteen Volunteer
Member # 79774

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Sometimesinthedark, we do very much appreciate it when our users help each other out, but we do ask that it's factually correct. Saying that orgasm is "the most ecstatic moment" isn't true for all people all the time. There are people who prefer other parts of sex, times when all kinds of people choose not orgasm, and people who never orgasm and feel happy and fulfilled. There are a whole range of reasons for all those situations. Angelwithashotgun also doesn't say anything that particularly indicates her boyfriend is anxious.

Angelwithashotgun, from what you say, I think the first thing that might really help you and your boyfriend out is to get clearer on some of the basics. It's very hard to be able to figure out what feels good and what doesn't, and to guide a partner around that, if we're not very familiar with our own bodies. If you haven't both had a good education about each of your genital anatomies, I'd recommend starting with these two companion articles: and
Then, even people with a great education can learn loads of really useful and amazing stuff from this:

It sounds like your boyfriend is being fairly clear with you about what he doesn't like. It's really important that you stop when he asks you to and that you don't try to persuade him to do something he's said he's not into. Those things are part of the basics of consent, which is essential for a healthy, trusting, respectful relationship.

He really does not "have" to orgasm sometimes. You're right that orgasming is healthy, but Not orgasming is also completely healthy. If he is happy about his choice not to orgasm, it's totally ok. If he is not happy about that choice, then it's something he needs to figure out for himself, and anyone putting any pressure on him or trying to change his mind won't help him with that and would also not be respecting his right to make that choice about his body.

Why do you want him to orgasm?

When you - or anyone else - is using the mouth in oral sex, "deep throat" is not automatically a part of that! More people do Not "deep throat" than do. That's likely something where porn may have misled you. You do not have to deal with or figure out a way round your gag reflex if you don't want to! As you're still fairly new to all this, I'd suggest leaving the "deep throat" stuff for now and experimenting with all of the different things you can do with your mouth, tongue and lips Without triggering your gag reflex. Also, for someone receiving oral sex, one part of the fun can also be seeing the giver enjoying themself too.

As you're probably figuring out, porn is a rubbish source of information about everything bodies, sex, what people do sexually and what people like sexually - other than what a small, fairly same-y group of people thinks looks good on camera [Smile]

The kyriarchy usually assumes that I am the kind of woman of whom it would approve. I have a peculiar kind of fun showing it just how much I am not.

Posts: 1786 | From: Europe | Registered: Sep 2011  |  IP: Logged | Report this post to a Moderator

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