Sexual Relationships
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Tips to impress my friends with benefits?

I broke up with my boyfriend of four years a few months ago. To deal with my sexual frustration I asked a friend of mine to set me up with one of his guy friends. We hit it off and we quickly agreed to become friends with benefits. He’s a great dude, we have great chemistry, and he’s pretty good in bed. I’m having a pretty good time with him, but I’m kind of struggling when it comes to having sex with him. I haven’t had sex with a new partner in years, and so having sex with a new person has been kind of difficult for me literally. His penis isn’t as long as my exes, but it’s a lot girthier and sometimes it makes penetration a bit painful, and it’s kind of impossible for me to go very far down when giving oral. We do lots of foreplay and I try incorporating my hands when going down on him, but he’s never once finished. He always outlasts me and leaves me sore. He’s never complained, but I want him leave feeling satisfied.
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Superb Opinion

  • It can get a little tough after breaking up with your boyfriend and it takes time to get comfortable with another guy. So don't rush it, take your time, adjust to your friend with benefits. When it comes to satisfying your friend with benefits, you don't need to take it all in when you are giving oral, you just need to keep bobbing your head in a consistent manner and use your hands from time to time, lick his balls if you comfortable with it. The next thing you can do, is be honest with him, he seems like a nice guy so tell him the truth and ask him about his kinks and preferences. Like what kind of stuff does he like during sex and what does he want you to do for him to be satisfied. You exchange kinks and then you both could try out new stuff with each other and have a better experience. And the matter of penetration being painful, I would recommend using different lubrication, like oil or those lubrication's sold specifically for sex, then you could try massages to lessen the sore pain, you can find those on the internet and tell him to be a little slower and gentler. If it is still paining then I recommend going to a doctor because it could be caused due to internal scarring or bleeding which needs medical attention.

Most Helpful Guy

  • It's not necessary to get the whole thing in your mouth. Take in as much as you can without gaging. Most of the pleasure comes from the first couple of inches of the dick, so focus on that with your tongue and lips especially the frenulum. Increase his pleasure by bobbing your head and stroking the shaft with your hand (s). Holding the shaft skin tight against the base with one hand while stroking with the other can add to the pleasure. Also give some attention to the balls by caressing and licking them. He could be shy about cumming in your mouth so be sure to encourage him a few times not to hold back and that it's what you really want. If you want to swallow tell him ahead of time so he can totally relax and let you take complete control.

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What Girls & Guys Said

1 5

  • From age 17 to age 19 I was with the same partner. Moving on to the second partner was actually more frightening than being with the first. Everything appeared the same, yet it was all so different. I knew what to do, I had been well educated, but the new partner looked totally different down there. I'm seeing a single pink slit, instead of something wine colored and with big lips. Okay, everything must still work the same, so proceed as normal. It worked.

  • Sounds like you satisfy him. Get some numbing spray for your throat so you can take it all in and just accept the vaginal pain

    • My throat isn’t the problem. He’s literally too wide for my mouth. When I’m going down on him I can't get my mouth past the head of his penis cause his shaft is too wide and it touches my teeth.

    • Try to wrap your lips inwards, too protect his dick from your teeth

  • If he's quite girthy and your feeling sore after sex are you getting plenty lubricated down there?
    Remember there is nothing wrong with using a little extra lube to help things feel smoother. Also there are lubes that give you both a little extra stimulation like hot, cold or tingly sensations this might help him get over the edge!

    Also don't be afraid to try new positions some will help you take his girth easier and you both will feel different sensations in different positions!
    My ex wifes talents consisted of 69 or missionary relying on me to put the effort in which was tedious. Now my girlfriend she puts just as much effort in as me and some positions (long list) we use give us way more stimulation!

  • What makes you think he isn't satisfied?

    • He hasn’t cum once.

    • Some guys have a hard time coming from a blowjob, doesn't mean that it doesn't feel great. It does!

    • We have penetrative sex as well. He just never cums.

    • Show All

  • A lot of the problem is probably that he's circumcised; that kills sensitivity and increases the chance that the woman will dry out during sex with all the extra friction.

    As for ways to impress him: use suction and lots of licking in your blow jobs, and be sure to really get into your sex with him (show enthusiasm, grind your hips into him, etc.).

  • Those things never work out no tips

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