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{ Tag Archives } first-time

I’m new to oral, what should I do?

Q: I’m a 20-year-old woman who has abstained from most sexual activity up to now by choice, largely because of reservations about the guys I’ve dated. I don’t regret that at all, but now I’m pretty inexperienced and seeing an older more experienced person. I imagine I feel as weird asking basic sexual questions as [...]

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Do uncut and cut penises feel different?

Q: What’s the difference between sex with a guy who’s cut vs. uncut? My current boyfriend is foreign and will be moving here within two weeks. It’ll be his first time overall — so naturally he’s terrified — and my first time with an uncut guy. Is it going to make a difference in how [...]

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How can I have sex without pain?

Q: I’m writing because I’m a 20 year old sexually frustrated female. I’ve had a total of three committed relationships, including the one I’m in right now. And I’m a virgin.
My problem: I can’t seem to have sex. There are both physical and psychological factors. Trying to have sex really hurts. Insertion is extremely [...]

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Should I do my friend’s sister?

Q: Hey, I’m a 17 year old junior in high school, and I’ve been friends with my neighbor since I can remember. His sister, 14, has always gotten along with me also. She asked me if we wanted to go “hang out” in her room. But then luckily some friends I play football with drove [...]

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Why can’t his penis get inside me?

Q: I am 19 and had sex with my boyfriend for the first time last night. I am on the pill and I didn’t have a problem becoming “wet” but I don’t think he ever was able to penetrate me. I am a virgin and am wondering if I am too tight. I tried to [...]

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Is a blowjob before the 1st time a good idea?

Q: I’ve heard it is possible to avoid the 1-minute wonder effect (that virgin males are infamous for) by getting a blow job before trying the big event. Is is possible to get another erection so early? I’m worried I will not have it in me for the actual deed.
A: First times can be a [...]

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How can we make our first-time having sex better?

Q: Hey SFSI, I’ve found your site very helpful already but I have some questions that are more specific about my the first time with my girlfriend. First of all we are both virgins and have decided that we want to lose our virginities to each other so here goes.
Question 1. I hear that when [...]

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What kind of condom should I use and will it make me last longer?

Q: My girlfriend and I have decided to have sex and she is going to be on the pill but do I still need to wear a condom? It’ll be the 1st time for both of us. She says a condom will help me last longer. What kind of condom should I use? Should we [...]

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