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My best friend's younger sister wants me to pop her cherry and give her a crash course in lovemaking...but she has a boyfriend

Tagged as: Dating, Family, Friends, Sex, Virginity<< Previous question   Next question >>
Question - (6 December 2012) 8 Answers - (Newest, 9 December 2012)
A male United States age 22-25, anonymous writes:

There's a girl who wants me to take her virginity and teach her about sex with a guy. She's a friend, but not a girlfriend, and I'm unsure about how to handle it.

I'm 23 and hope to graduate next May with a degree in marketing. I'm unattached after a long term relationship broke up eight months ago. My best buddy will graduate next week, and plans to get married next summer after his fiance' graduates. We have been best friends since High School, about 7 or 8 years. His little sister is almost 20 and has been tagging along with her brother and me for a few years. The three of us all go to the same university, and all still live at home although I have almost a private apartment (no real kitchen) in the walk-out basement of my folks' home. I pay rent and they let me use it like my own place, even overnight guests, but no live-in girlfriends.

Little sister is super smart and in her second year of Chemistry on a full scholarship. She wants to go to med school but do research instead of becoming a doctor. She has many characteristics of a stereotype nerd girl. She's interesting, pleasant to be around, and has a clever but cynical sense of humor. But she's very quiet, not outgoing, and not very confident in herself. She's probably better than average looks - a little taller than most women, slim but not skinny, small boobs, nice smile. But she dresses rather drab and always seems to look a little sloppy in appearance. She has dated a few guys off and on but nothing serious until this summer. Over the years I even went out with her about half a dozen times, and made out with her a couple times. This past summer she met a guy and by September they were pretty serious and exclusive with each other. He's a Lieutenant in the Navy and had to leave on an assignment in October. He can't use a cellphone and gets email about once every week or so but they have been doing the LDR thing for the last two months. I found out they have talked and written about some serious long-term plans, like going to school together after he finishes his Navy hitch, what they expect in marriage, when they want kids, etc.

So last weekend my buddy, his sister, and his fiance' were at my place, hanging out and watching some movies. After a while my buddy and his fiance' went to my bedroom to have sex. I'm OK with that, they've done it quite a few times since he lives at home and she's in a co-op house run by a church and doesn't have a lot of privacy, but this was the first time little sister was along. She and I could hear her brother and his G/F getting it on and started talking about it. She said she had been awake most of the night listening to her brother take his fiance's virginity, then screw their brains out, the weekend they got engaged at her parents' lake house. Apparently doing what had to be done was not pleasant, and little sister heard the sounds of pain and sobbing the first time her brother's fiance' had sex. Little sister said she definitely did not want to go through that with a guy she really cared for and asked if the first time always hurt the girl like that. I said I'd never had sex with a virgin, but I heard it varies a lot from girl to girl, and how experienced her partner is, and how well he gets her ready.

Then she had about a hundred questions about sex and how to make it good for a guy. She hasn't done much beyond making out and some fondling. She lied to her B/F and told him she had fucked a boy once, and slept with another guy a few times. Her B/F said that was good since girls get curious and almost never stay with the guy who takes their virginity, and he didn't want to spend a month teaching a girl how to be good in bed like he had done once. We ended up dry humping each other just before her brother and his G/F finished. I creamed my jeans and she seemed kind of pleased when I told her what happened, but I don't think she got off even though she ground against my hip and thigh for quite a while.

Tonight I got an email from her saying that she wants to do something very special for her B/F when he returns next month, to make their relationship "very long term or even permanent" (her words), and would I help her learn how to really impress him. She said that her parents will be out of town this weekend and she could spend as much time with me as needed. As if that wasn't a clear invitation, she said she would tell me more later but she had to go pick up the birth control prescription she takes for cramping and female problems before the pharmacy closed. I said I'd have to check the schedule at my part time job tomorrow and let her know when I would be available.

It's pretty obvious she wants me to pop her cherry and give her a crash course in lovemaking. I'm not worried that we're not in love since sex is basically a natural thing for two people to enjoy by mutual consent, even if it is better when you have feelings for your partner. I've done it with around 25 women, starting at 16 with the same neighborhood girl who got my brother's cherry a few years earlier, and ranging from one-timers whose name I wasn't even sure of, to the two-year LTR that broke up last spring. But I never had sex with a girl when another guy was in the picture and I never did it with a virgin. As far as I know all my partners were rather experienced.

Her having a B/F bothers me a little but not much. He already thinks she's experienced and he's cool with that. I asked my buddy about her B/F and he thinks the B/F is a decent guy and pretty serious about little sister. A couple times over the years he commented that his sister could be pretty hot if she wanted to, and getting laid would probably improve her confidence so I don't think he'd mind if I did her. It's the virginity thing that sort of bothers me.

In spite of what her B/F said, I heard that girls get rather attached to the guy who takes their virginity. Is this true or is it because they are already attached when they decide to spread their legs? I respect my buddy's little sister and consider her a good friend but I don't have real feelings for her. I don't want to cause a breakup between her and her B/F.

How much practice should a girl have with things like fingering and oral sex, and a man's body, before she tries the real thing? I had quite a few handjobs and oral sex (both ways) with a few different girls before I actually had intercourse. I think working up to it like that made me a better partner for the girls I had later. Can little sister be good after just a weekend, or even a couple weeks?

What should I do to make it memorable for her? Can it be romantic without getting attached?

What's the best way to manage the actual first fuck? There are hundreds of web sites about this but they all assume you're in a relationship with your partner. I want to be gentle and minimize her pain but I know it'll probably hurt her and she may cry. Did any girl actually change her mind after he started putting it in? Suppose she doesn't really respond to the foreplay. Should we do it anyway, or call it off? Some pages say a virgin girl should get on top, but most experienced girls prefer the first time with a new partner to be missionary and I imagine a virgin would be too nervous to even think about any other position. How soon after the first time can we do it again?

Should I plan the first time to be just a few hours together, or should it be longer? My first time was an all day and all evening encounter and then I was back the next day for more, but I sort of had a crush on the girl. Is it better not to have that much time together since this is more of a casual hookup?

Well, I have been thinking through this all evening and just writing it all out has helped but I want to hear other people's thoughts.

View related questions: a break, best friend, boobs, broke up, confidence, crush, dry sex, engaged, fiance, fingering, foreplay, hand-job, has a boyfriend, lives at home, navy, oral sex, she has a boyfriend, university

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A male reader, anonymous, writes (9 December 2012):

listen, there is casual sex and then there is "love". Most of you are getting the two confused. The lil sister is obviuosly interested in trying casual sex despite what she says about her long term relationship with her boyfriend.She is only 20 years old and just beginning to experience healthy sexual desires. Go experiment with her. It is only casual sex we are talking about here

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A male reader, Serpico United States +, writes (7 December 2012):

Best friends sister/family/gfs/past gfs are all off limits IMO. Way too many women out there that to ruin a friendship over one.

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A male reader, anonymous, writes (7 December 2012):

This girl seriously needs help if she thinks it would be better to cheat and get experience with another guy before sleeping with her BF.

She seems to regard the losing virginity experience as some kind of burden that she can cheat and relieve her BF of. I'm guessing she has the typical female mistaken idea that because experience makes a man sexy to them, then surely experience would make a woman more sexy to a man. It's usually wrong but it is still a common belief among young women today. Not every guy has a fetish for 72 virgins, but most guys still consider it an honor to be a girl's first and prefer her to have less experience and not more. No guy wants his GF to cheat on him to get rid of her virginity, thats for sure.

Don't sleep with her. Explain to her how she is horribly misunderstanding men by wanting to do this. If she is still hellbent on getting her hymen out of the way before sleeping with her BF then offer to buy her a dildo.

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A female reader, Candid Cally United States +, writes (6 December 2012):

I do not think that you should do anything with your best friend's little sister. If you do, you will complicate things beyond what you can imagine.

She can find the information she seeks online.

If she wants to make sure her first time doesn't hurt, she should buy a small dildo and use it herself. If you want to have some part in this...buy the dildo and give it to her...do NOT have sex with her and do not engage in further intimate acts together.

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A female reader, EbonyBlossom United Kingdom +, writes (6 December 2012):

EbonyBlossom agony aunt1. Are you 100% sure you dont have feelings for her? If so then definitely dont go there.

2. Are you definitely sure she doesnt have feelings for you? I think you need to clarify this with her before doing anything.

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A female reader, Honeypie United States + , writes (6 December 2012):

Honeypie agony auntNO offense...

Honey, You are no prize winning stud, OK?

IF you have sex with her, she will without a DOUBT develop feeling and an attachments to you. She might also regret the sex deeply once she figures out that this doesn't mean anything emotionally for you.

You shouldn't EVEN be considering this. If you were a sex-therapist or sexual surrogate then MAYBE this wouldn't be such a bad idea - but you are neither so it REALLY is a bad idea.

First of all, she has been LYING to her BF, making him think she HAS experience sexually. And now that she think she might have to put her "body" where her mouth is, so to speak - she is afraid he will find out she is a virgin and not want to be with her.

She OUGHT to have sex for the first time with a guy SHE is emotionally & physically attracted and connected to. Unless that is you, this should be a no-no.

If the BF doesn't want to take the time and effort to be her first, then she needs to cut her loses with that one.

THERE IS no rule out that the girls don't stay with the first guy they have sex with. Many don't because they mature and outgrow their first sexual partner, usually because they have sex in their teens. And there is no rule that a girl SHOULD stay with the first guy she has sex with, it's rather preposterous - unless of course her faith/religion dictate it and I see no mentioning of religion here or marriage.

Instead of thinking this is GREAT you get to break in a new girl.... TEACH her what being in a relationship is about (if you actually HAVE a clue). About having a moral compass, about being faithful, trustworthy, honest and open.

And then we have the Best Friend issue... You don't think if you did this it would screw up your friendship? Seriously? You think you could do this BEHIND his back and BEHIND her BF's back and no one would be the wiser? /facepalm.

Honey, grow up, stop thinking you dick is a magic wand and get yourself a moral compass.

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A female reader, k_c100 United Kingdom + , writes (6 December 2012):

k_c100 agony auntI dont really know where to start!

1. "Her having a B/F bothers me a little but not much. He already thinks she's experienced and he's cool with that. I asked my buddy about her B/F and he thinks the B/F is a decent guy and pretty serious about little sister."

Yes he thinks she is experienced, but he doesnt think she is a cheat!! She will 100% lose her boyfriend over this, this is straight up cheating, so if he ever found out she would be dumped immediately for lying and cheating. He would far prefer it if she told him the truth about her virginity so they could make it special together, the last thing he would want is for her to sleep with a cheap guy like you who sleeps with anything that moves.

So if you want her to lose her boyfriend then go ahead. In fact if he found out she was dry humping another guy while he is away I think he would dump her anyway, so she has already been unfaithful so there is not much point in her trying to pretend anymore that she wants a long term relationship with him.

All she is going to give this guy that is 'special' is an STI she catches from you and a nasty shock when he finds out she fools around with her brother's friend.

I was going to answer your other questions, but there is honestly no point. She cheated on him when she dry humped you, she has no idea about being in a faithful long term relationship and realistically whatever she does with you next isnt going to matter, she has ruined their relationship already.

You do have an opportunity however to be a mature adult and try and teach her some morals, like cheating is bad, being faithful is important, how you shouldnt fool around with others behind your partner's backs...how sex should be special and not given away cheaply...you know that kind of stuff.

Something tells me though that the kind of guy that 'creams his jeans' just from a bit of dry humping wont do that though, you sound like you have less morals then she does and doesnt really have any idea about sex and relationships. There is not much hope for any of you really!

But let me tell you this one final thing - when a woman has sex with a man it releases hormones after sex that create an emotional attachment to that man. And these hormones are a WHOLE lot stronger when the girl loses her virginity. Hence why they say losing your virginity should be special, espcially for the girl. So will she become attached to you after? Without doubt, yes.

She should lose her virginity to a man that loves her and wants to be with her a very long time. Definitely not you.

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A female reader, anonymous, writes (6 December 2012):

My thoughts are that a true friend would never go behind his best friends back and steal his little sisters virginity. And while I have respect for the men and women who serve their country. I have none for the guys who sneak about behind their backs while they are away...'serving' their partners!

You can't possibly think this is a good idea on ANY level. It's a dreadful idea. I would stick to the fantasy if I were you and leave this girl alone. IF this post is genuine, this girl has trouble written all over her!

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