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Mr_Saturn512's avatar

(NSFW) How can I get myself to orgasm with a condom while having sex?

Asked by Mr_Saturn512 (558points) September 24th, 2016

Totally TMI here.

I grew up a good chunk of my life masturbating by proning – meaning rubbing myself against a surface. I wasn’t was aware that the “normal” way was to do it by hand until the end of high school, when I started to understand jerking off jokes.

I proned for a long-ass time until my senior year of college, when I finally had a girlfriend that I became sexually active with. It seemed to be a gift and a curse, because while I was always able to satisfy my girlfriend and last in bed, it’s VERY hard for me to get off inside of her with a condom. Without a condom is totally fine. But with a condom – it takes me forever and it’s such a pain (not literally in the physical sense – it’s just tedious).

Eventually I weaned off proning and got to do it by hand.

I still have problems getting off inside my girlfriend with a condom though – I’ve just been so used to rough friction. I really want to work towards fixing that. Another issue I’ve been ashamed to admit is that – I fucking masturbate so much. I really do. I’ve been keeping track this year on an Excel spreadsheet and so far it’s an average of 2 times per day. I’m the kind of masturbator who does it even during work when I’m alone at my desk, and my job is really boring and dull so I end up turning to masturbation to pass the time.

I believe I have to wean myself off masturbating so much, and not only that but I should only masturbate with a condom on just to get used to the feeling.

Right? I mean – if there are other creative ways to get used to a condom, I’m all ears.

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22 Answers

funkdaddy's avatar

Skipping over a good portion of info here and just getting to the main question, have you tried different kinds of condoms?

There’s dozens of kinds, just a couple of examples
– different sizes
– varying amounts and types of lubricant
– different textures
– different shapes, including some with extra large heads to create more friction on you
– thick and thin material
– non-latex options

Something there will help, take a look and try the ones that sound appealing. Some brands sell variety packs to try out different things, but I’d guess you can pick a few that might help you out personally, get small packages, and go from there. Amazon has thousands.

Good luck.

filmfann's avatar

Satisfy your girlfriend, then have her remove the condom and blow you.

MrGrimm888's avatar

If it makes you feel any better I can’t even keep it up in a condom. They suck. I don’t stay in relationships with women that make me use them. I’m a pull and pray guy. No kids yet. I think…~

As far as masterbation goes. Don’t do it at work geez. Read a book or something.

JLeslie's avatar

^^Pregnancy is the least of the worry. Pulling out is pretty effective actually, but it doesn’t protect you from HIV, HSV, or HPV, or many other diseases. Some curable, some not.

@Mr_Saturn512 Try using your mind more. Really focus on how things feel. Even imagine you are feeling more than you are. Close your eyes, focus. Most men are very visual, so maybe paying attention to visual things will work better, but I’m not a man, so for me, closing my eyes and really only feeling what is going on is what works best for me.

Men too often like a whole bunch of distraction instead of just being in the physical moment. They get used to porn, or lights on, or blow jobs, or whatever else. They too often can’t just have simple sex. They get out of practice, or never had it to begin with. I think you can get into practice if you work on it. If you can’t climax with a confirm in the end, so what. Don’t get too crazy about it. It’s not like your trying to make a baby and you need it to work.

MrGrimm888's avatar

^So sorry. I wasn’t supporting unprotected sex. Just saying my part.

The safest sex is careful partner selection.

Lightlyseared's avatar

More practice.

ragingloli's avatar

Use ribbed condoms and turn them inside out?

ARE_you_kidding_me's avatar

Make sure you are not buying the ones that are intended to desensitize you.

jca's avatar

I am not a guy so I probably don’t have a clue but my guess would be to masterbate less so you are ” ready to go” when you are with your girlfriend.

Cruiser's avatar

If you are keeping track of your masturbation on an Excel spreadsheet then IMO you are obsessed with sex maybe even addicted to sex and this may be unhealthy for an intimate relationship with another. Ditch the spreadsheet and the pillows, couches whatever you are humping and focus on your relationship with your girlfriend and there are more sensitive condoms out there that you could possibly try to help you out in that regard.

CWOTUS's avatar

I don’t know why the most sensible response here has to come from a woman, but there it is. @jca has the answer to your perceived / stated problem. Just as your earlier habit led you to desire a certain level of friction to achieve orgasm, now your current habit is doing the same thing. Your frequent masturbation (I won’t say “too-frequent”, because that’s a judgment for you to make on your own) is desensitizing you to the much lighter touch of a woman’s body transmitted through the condom.

Just stop masturbating so much. If you can stop completely, then so much the better. I’m sure that’s easier said than done when so much of your current focus is on your penis and how good it feels to climax – everyone knows that; no surprise there. But there are also ways that you and your girlfriend can make this a part of your sex play, too. (And once you give her the full control over your orgasm frequency, mode and method she may not give it up again without negotiation. Those negotiations could be enjoyable, too.) If you give up your masturbation habit – and especially if you give up that control to your girlfriend – you may, in fact, become far more sensitized than you are now. Again, it’s your own judgment about which state is preferable. Just realize that nothing is perfect, and accept whatever enjoyment you can find.

Espiritus_Corvus's avatar

I think you should abstain from any tactile stimulation to your penis for awhile—long enough for it to become re-sensitized again. And when the time is right, I think you should allow your girlfriend to do the honors.

kritiper's avatar

Find a more sexually enticing, alluring girlfriend. Usually guys get theirs first and fastest, with the poor women getting theirs last or not at all. I would be thankful for the delay so my girlfriend could be more happily satisfied.

janbb's avatar

@kritiper Are you seriously blaming his girlfriend for this problem or is that just a joke? Surely she’s more “enticing and alluring” than a pillow? But I agree with the second part of your answer that lasting can certainly be of benefit to the woman.

I would go with the masturbate less camp and also have her finish you with her hand or mouth if you don’t come with the condom on.

JLeslie's avatar

A long delay is not always a good thing for the woman. It can get boring and tiresome. Depends how long, and depends on the woman.

ibstubro's avatar

First, buy some good silicone lubricant and use it to hand jack yourself – Swiss Navy is good – or buy a pussy simulator. You need to learn to pleasure yourself instead of simply getting pleasure from cumming.

Second, when I was your age if I could have held my jacking to twice a day, I would have been thrilled. Consider it a hobby. Dermabrasion wise? I’m probably on my 9th…er…member.
NOT COOL at work. If you have to, and your not in the bosses office, use the stall in the restroom.

Does the successful sex – sex with your girlfriend – satisfy you? Quiet your sexual craving?

kritiper's avatar

@JLeslie No, I am not kidding. Are you assuming that a pillow is as sexually stimulating as a woman? Or a sheep? Or a tub of lard? I’ve seen women that would make me wilt in a split second.

JLeslie's avatar

@kritiper Did you mean to address me?

kritiper's avatar

@JLeslie Sorry, I meant to click on @janbb

JLeslie's avatar

No problem.

DarknessWithin's avatar

Although I’m a woman and have not yet had your fortune of finding a partner I have the knowledge to asses that perhaps the issue is not the condom.

It could be that the excessive masturbation is causing overstimulation, reducing your drive.
Not to mention it’s defeating the purpose of your having a partner.

Leaving yourself deprived in between performances with your girlfriend might help but you’ve made clear that you focus pretty heavily on how long it takes you to achieve orgasm and I believe the wrong focus and/or discomfort can be straining on performance. Try a tantric like approach and focus on the process and on your girlfriend instead of on achieving orgasm.

But you must also ask yourself, are you comfortable with this girl and does she satisfy your need for pleasure? It could be as simple as that she’s not the right partner.
Is she your first and if not have you had this struggle with other partners? It could also be that female partners are not your sexual preference. Forgive me but all possibilities must be explored.

The masturbation definitely needs to stop in any case. Your habit of it does come across as possibly somewhat unhealthy.
Especially refrain from it at work. There are ways to occupy yourself during a lacking shift that if necessary can distract you from arousing thoughts. Whenever I leave the house I carry a book and my handheld video games so that I’m always prepared for the possibility that I’ll need something to do. Other suggestions are to install games or stream media such as Youtube on your phone.
If arousal does happen to occur while you’re at work at least excuse yourself to the restroom since you made it sound as though you don’t use an appropriate amount of discretion.

If you find it impossible to stop and even experience withdrawal symptoms if you attempt to that’s how you know that you have an addiction problem and should seek professional help.

MrGrimm888's avatar

^Aside from doing it at work, masterbation is kind of a must for males. It builds up,and has to get out. If you don’t masterbate you’ll have ‘wet dreams.’ We men are like cows, that must be milked. Unfortunately, it’s hard not to get it out.

It was mentioned before in this post, women probably wouldn’t want to be our only source of release. The horniest girlfriend I ever had still didn’t want sex as much as me. I had to masterbate so she wouldn’t think I just wanted her for sex. It was impossible for me to be close to her without wanting her. A natural thing for me, but sometimes she just wanted to spend time together. I loved her,so let tried to take some of the pressure off her by taking care of myself sometimes. I would usually refrain for a day or so if I knew we’d be together for the weekend, but that was the best I could do.

Women clearly don’t understand the curse of being a man,when it comes to testosterone, and sperm.

It’s all we ever think about (sex.) Getting the sperm out,on a regular basis, is the only way we can appear sane.

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