Miss Information: Advice for a 25-year-old virgin

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Dear Miss Information,

I've been seeing my friend-with-benefits for over three years. In that time, I've been on one date with someone else, and my FWB hasn't dated anyone at all. This is not by contract — we've both agreed we're welcome to see other people.

I'm starting to crush on my FWB big time, and I know that he's crushing on me too. The problem is the age difference. He's twenty-six and I'm forty. He's also very good looking and personable. No matter how he feels about me now, I know it's a matter of time before he finds someone else, and I don't want to interfere with his happiness when that happens. But I also don't want it to break my heart. I've been thinking that maybe I should start dating in order to prepare myself for this eventuality and keep from focusing on my FWB as "The One." But I think that despite our stated agreement to keep the relationship open, my FWB will probably be hurt by my doing so.

Should I just stay with him, and stock up on cheap wine and Häagen-Dazs to prepare for the inevitable? Or should I protect myself by dating others, possibly leading to an earlier demise for the relationship? — Confused Cougar

Dear Confused Cougar,

Forty is not that ancient and twenty-six is not that infantile. Just as there are lovelorn women who prefer Anchor Steam and olives to Franzia and rum raisin, there are youngish men who are capable of mature, committed partnerships. It's not about sex or fetishes or biding your time until something better comes along. It's also not a hunt for a sugar mommy to lavish you with economy-sized boxes of cereal and tube socks. These are regular guys who fall for someone a little older. That's not a tenth of what it'll take to get you on Jerry Springer. It will, however, give birth to zillions of newspaper trend pieces, a Jennifer Aniston flick, a Courteney Cox series, and a throwaway reality show.

While we wait for "The Manther" to get the green light from ABC and Columbia, let me ask you: how many of these concerns are valid and how many come from this bullshit soufflé of internalized media messages, low self-esteem, and personal prejudices that you've whipped up for yourself? Just because someone tells you to feel like an oddity doesn't mean you have to. Think about it:

Fact #1: Whether it's intentional or not, you've been exclusive for three years.

Fact #2: You're feeling something for him and you think he's feeling something similar.

Fact #3: "Good looking and personable" people look for the same in others.

So why are you the charity case? Why not him, who came of age when Ricky Martin, Britney Spears, and Sugar Ray were topping the charts instead of Prince, Madonna, and Stevie Wonder? You've got the experience, street cred, and the good looks to attract the young'uns, not to mention what I'm assuming is a much healthier bank account. Will he be doing as well at your age? Who knows.

If you like him, put it out there. If he's not into it, you can go back to the previous arrangement or find someone new and get rid of this dark cloud. You don't have to send him a dozen orchids or prepare a big speech. Make a joke about "renegotiating your contract" or ask a rhetorical question ("Why do you think after all this time we haven't 'gone there' as boyfriend and girlfriend?") to get the conversation going. And a little liquid courage couldn't hurt.

Dear Miss Information,

I'm a twenty-five-year-old straight male and regrettably still a virgin. I just never really seemed to hit my stride with girls in college, and next thing I knew I was out in the working world with no idea how to meet anyone. I've started to get it together recently though, and I met an amazing girl. We've really hit it off and it seems extremely likely that clothes will be coming off in the near future.

My question is this: when the time comes, should I tell her I'm a virgin or stick with the fake-it-till-you-make-it plan? On the one hand, it would be kind of a nice pressure release to tell the truth, but on the other, I keep picturing her thinking, "He's still a virgin!? I wonder what's wrong with him?" For my part, after many hours of reading advice columns and articles, I've culled together a plan that I believe to be a fairly solid stab at what sex should be like: a steady build up of rubbing/kissing/licking various body parts leading into some (I can only imagine glorious) oral action. I'm not sure exactly when to transition to actual intercourse, but when we get there I'll just try to keep an even thrusting tempo and hold out as long as I can. I think I can pull it off.

I would of course prefer not to have to follow a strict plan and just have her tell me what to do, but then I would have to admit that I have exactly zero first-hand knowledge of what turns a woman on. I'd welcome any advice you might be able to proffer. — Inexperienced, But Eager To Please

Dear Inexperienced,

Virginity is not a sexually transmitted disease, nor is it a secret wife or a girlfriend. There are benefits to disclosure, both for the person you're sleeping with and for yourself, but it's not a moral obligation. If I'm reading your letter correctly, this virginity is an unfortunate product of circumstances, not some deeply held personal creed or prerequisite to finding a spouse. In either of those instances, there's more of an impetus to be up-front. However, it's totally acceptable to play your V-card closer to your chest if having a new experience and popping your cherry are the primary goals. In short, do what makes you comfortable. You may opt not to tell her, then have it come up mid-coitus. You may tell her right afterwards or a month later during a TV commercial.

Which leads me to another point I want to impress upon you, Inexperienced: sex is unpredictable. It's great that you're studying up. The internet, books, and magazines can be a great way to learn, and so is talking to people you trust. But I don't know about all this, "I'm going to do this, then that, then this, then more of that..." Are you engaging in a natural, organic act or blocking out stage directions for a Broadway show? I think your second instinct, i.e. can it with the fancy plans and follow her lead, is going to work out much better for you. And while everything you mentioned sounds lovely, keep in mind she's also going to want to pleasure you as well. Half the fun is the power dynamic and knowing you can get the other person off.

As far as the transition to intercourse, I wish I could tell you that balloons will fall from the ceiling, a disco ball will appear, and a guy in a sequined tuxedo will yell, "And awaaaaaaaaaaaaaaaaay we go!" The reality is more like: "You ready?" "Yeah," followed by the donning of a condom. If that feels too direct, something like, "I'm really turned on," or, "I can't wait to be inside you," usually gets the message across, as does, "Should I put this on?" while holding up a condom.

Readers, any additional advice for Inexperienced? What didn't you know then that you're happy you know now?

Comments ( 27 )

To Inexperienced, well, when the foreplay has got her moaning like she's going crazy, probably not a bad time to ask her if she'd like "something more" ;)

Jay commented on Sep 21 09 at 2:59 am

I'd say tell her that you're new to the PIV bit. That will take a lot of the pressure off. I didn't disclose my virgin-with-some-fucking-around status until after some serious making out and heavy petting which worked well. He didn't know that I'd given all of two blow jobs before, but he didn't expect me to have the first idea what to do when it came to sex.

Anna commented on Sep 21 09 at 4:27 am

If you've read up on all the parts that make the other person feel good, then you're better off than most of the kids who lost it in high school. Don't worry about planning, just concentrate on what seems to be making the other person feel good, or not. Even if you weren't a virgin, some stumbling is to be expected the first time with a new person, 'cause everyone's different. I'd lean toward the don't tell her in advance camp (but don't lie if she asks), and be prepared to brush off any awkwardness as we're-new-to-each-other stuff. You're the one with first-hand experience, though, so do what feels right.

JCF commented on Sep 21 09 at 8:54 am

Whatever you do, don't wear a condom. You won't feel anything if you do. And besides, pregnancy and STD risks are vastly overstated. Trust me on this.

Mike commented on Sep 21 09 at 11:40 am

d say tell her that you’re new to the PIV bit. That will take a lot of the pressure off. I didn’t disclose my virgin-with-some-fucking-around status until after some serious making out and heavy petting which worked well. He didn’t know that I’d given all of two blow jobs before, but he didn’t expect me to have the first idea what to do when it came to sex.

sam commented on Sep 21 09 at 1:11 pm

Oy vey. Don't listen to Mike, Inexperienced: pregnancy may not be a big deal for a chap, but it's not a choice you can force on someone you're hardly been dating that long... and one cannot overstate the STD risk. Even mild stuff like herpes is with you for life - and believe me, GSK, Merck et al aren't putting big money in HIV drug research 'cos it's some minor thing no-one catches. And gonorrhea and syphilis are on the up again. Check the stats at NIH.

MG commented on Sep 21 09 at 6:24 pm

Inexperienced is in a wonderful position which most women would possibly kill for. If he has reached the heavy petting stage it would be good for him to get 3 or 4 condoms - "just in case" he might have that type of night. She will appreciate that.

Otherwise, he should just keep concentrating on the heavy petting and kissing everywhere (DATY soon too) and don't go too heavy on the booze as he wants the event to have repeaters and a future. Precede and follow the event with plenty of praises and cuddling.

lee commented on Sep 21 09 at 8:24 pm

I dated a guy for a while and I was his first. I actually found it kind of a turn on. I was able to direct him and teach him how to please me and we had some mind blowing sex. I taught him how to be a (imo) great lover, and he taught me to be vocal in what I like in bed.

Lisa commented on Sep 21 09 at 9:42 pm

Booze...possibly weed.

Felix commented on Sep 21 09 at 9:51 pm

I once told a woman, truthfully, that I was a 26 year old virgin. She succinctly typed back "bs." Mind you, I was on Adult Friend Finder trying to lose that virginity.

Eric commented on Sep 21 09 at 10:51 pm

I'd say *definitely* tell that girl you're a virgin. Not only does it relieve pressure you're feeling currently but she'll be eager to show you the ropes.

Coheed commented on Sep 21 09 at 10:54 pm

hit it! tell her as soon as possible also. It is better to apologize than ask for a favor.

megarie commented on Sep 22 09 at 2:20 am

Don't forget the lube/lots of female oral sex. A vagina that is anything less than... slippery is an enemy to rubbers

Caitlin commented on Sep 22 09 at 2:26 am

Second letter - I think what you tell the woman would depend on how experienced she is herself. I am 37 and had been with a few partners, had experienced incredible sex and know exactly what I am after. This letter was a turn-on! You could definitely admit this to me!

A girl in her early twenties may not have a clue yet on how to deal with inexperienced male and could need a lot of guidance herself. On a bright side, she may not even notice anything strange and just think this is the way you do things. I wouldn't tell her.

In the mean time, can you go to a bar, pick up an older chick and practice?

NU commented on Sep 22 09 at 1:35 pm

I think that if she's really a great girl she won't mind the confession, and might actually like it. I once dated a guy who, though he wasn't a virgin, had had sex (of any kind) a total of twice before me. I had honestly kind of expected him to be a virgin, and didn't mind the situation at all - it actually took a lot of the pressure off me to perform and impress, and relaxed is always good. And may I say, he was a surprisingly good cunnilinguist. Said he'd done some research.

barlova commented on Sep 22 09 at 4:39 pm

First, DO NOT tell her you're a virgin. It may not, but it freaks some people out. If you tell her at all, it should be months later. Second, beat off twice before the date when you expect to have sex. This will take the pressure off worrying about premature ejaculation. As for not knowing what to do, don't sweat it-- first time sex is often less than perfect even with experienced types, so what's the big deal. After the first time, commit to get better.

polevod commented on Sep 22 09 at 6:48 pm

I think your advice to the cougar is a little too optimistic. I had a girlfriend over ten years my senior. It was great for a couple of years, but I started feeling trapped by the age difference. She was too old to be a mother, which derailed some of my big goals in life. The breakup sucked for both of us, but was eventually necessary. We're still friends, but the memories of what we had complicate things.

Eric commented on Sep 22 09 at 8:11 pm

I was fooling around with a girl in bed when she asked me how many women I had sex with. I truthfully replied 'None'. I had to convince her I was a virgin. Then, I turned down sex. While she was naked. Still not sure why I did that. Maybe because sex probably meant having breakfast with her police officer father, mother, and 11 year old brother.

Now it's a year later and I'm a 24 year old virgin.

Scott commented on Sep 22 09 at 9:56 pm

One more tip to the virgin: don't be surprised if you have trouble staying hard the first time you attempt penetration. Many, many guys have that problem, especially with girls they really like, and condoms certainly don't help. (I agree that should you use a condom -- VD sucks -- but I'm also really tired of preachy safe-sex advocates who aren't willing to acknowledge that they really do make sex less pleasurable.) If the first time doesn't happen, the next time will.

S.F. commented on Sep 22 09 at 11:18 pm

mike is right, don't wear a condom the first time, every time after that use protection but you want to get the full experience the first time. I wore one and I regret it to this day.

JF commented on Sep 23 09 at 12:48 am

I was a rather late starter, but once I got going, well....

It depends very much on the person of course, women tend to like prior experience in a partner and men don't, both of which ideas are stupid. But basically, once she has decided to do the deed with you, she pretty much has, and likely not much you say about this will change her mind one way or another, though it might be either a slight turn on or a slight turn off.

But as said above, first times are almost always awkward no matter how experienced you are, and often not particularly good for the female partner, these things take time.

In any case, both sexes make far too much out of virginity, in different stupid ways. Just do it and get it over with, then start trying to apply some rationality to your sex life (as if that were possible).

(In my own case, I fessed up right after, and she refused to believe me, which true or not, made me feel like about a million bux. We broke up as a couple fairly shortly after, but remained FWB for many years thereafter when we were in dry spells. She eventually married my best friend.)

Norm & Al commented on Sep 23 09 at 2:09 pm

Is it occurring to anyone that it's not totally, unequivocally up to Inexperienced if he wears a condom or not? Sex does not happen in a vacuum, and two people have to consent to what's going on. Yes, obviously, condoms feel different than going at it bare, but they don't make it feel BAD and there's brands and styles with varying degrees of sensitivity. I mean, seriously, some of these comments make it seem like it's the end of the world if you have to do anything more during sex than thrust for three minutes. A little desensitization your first time might not be the worst idea. Personally, I choose Lifestyles, I like the texture and they gotten good feedback from partners (I'm hetero female, btw. Condoms change the feeling of sex for women too) I know Trojan is kinda the top dog amongst condom manufacturers, but I've always liked them the least--very thick and overly rubbery feeling to me. Also, you can let her know you're inexperienced w/out outright stating "I'm a virgin". If you wanted to mention that you've not done this alot, or not been w/many girls, or however you want to phrase it, it may compel her to take the lead so you can relax about performing a little and let her give you an idea of what you like and show you what she likes.

NM commented on Sep 23 09 at 9:32 pm

Advice for the 25-year-old virgin:

Erin is right that sex and desire are messy and unpredictable and wonderful. So stop trying to plan it out. Your body -- and hers -- will tell you what to do, if you actually take the time to pay attention.

However -- one thing that you can study up on, are the many techniques for eating really good pussy. So:

1) Get yourself a good book (Good Vibrations, either in-store or online, is a good choice) and see how many different books they have just about making a woman come with your mouth. Then get one and study it fully.

2) Do not -- I repeat, do NOT -- use porn as a guide on how to eat pussy. As a matter of fact, try not to use porn as a guide to what you should do. Very fun to watch -- but you are a beginner, so don't try it at home.

3) Not all women like to be eaten the same way, and some women find that their moods dictate what they like or don't like-- it may change based on the time of day or how many times she has come already or what she just watched on TV or a million other things. It's why you study and get lots of techniques, uh ... under your belt.

Don't go into your first time with all kinds of expectations -- it'll probably be a bit messy, a bit awkward, and a bit fantastic all at the same time. But no matter what happens, you'll be able to say, "I had SEX."

Go get 'em.

bluecats commented on Sep 23 09 at 10:49 pm

To the 25 year old virgin: Maybe you could relate to my situation? I was celebate for 3 years. The initial suggestion was to do it for only one year, and somehow that turned into 3. Not that I'm not attractive, personable, sexy, etc. Just happened that way. I always wondered the same thing, "Should I tell the person who pops my born-again-virginity cherry before hand, or should I just fuck the mailman to get it over with?" The way it worked out seemed to be perfect. Began dating a lovely person, we had sex after a few weeks of dating, when it just felt right. It was casual, no pressure. The foreplay and sex itself was simple, straightforward, not drawn out long, and perfect. He had NO idea until I told him afterwards that it had been my first in over 3 years... I think that was a good idea because he didn't feel the pressure of giving me some 3-years-worth-the-wait experience (although it proved to be that, on it's own, over time) and the advice I've seen that people have already suggested to you which is to let go of your own expectations is right on. Remember that human sexuality is natural. You dont have to have done it a million times with a million different people to know what to do. It's in your genetic make-up. Just relax and go with the flow. It'll happen and it'll be great.

Sara commented on Sep 24 09 at 9:57 pm

Make sure to practice beforehand how to put on a condom. I recently deflowered an older virgin, who I didn't know had zero experience before we hit the sack. He had no clue how to put on a condom. That's how I realized he was a virgin.

TM commented on Sep 25 09 at 11:09 pm

Make it easy for yourself, Virgin; just say "tell me how you like it." You don't have to say why you want to know. And if there is any confusion, ask her to show you. Be observant of how she's doing. And make sure you have a selection of lubes, and be generous with the one she likes. That was my worst mistake my first time.

I would suggest not whacking off beforehand; if you come early, switch to fingers and/or oral, keep her rolling along, and soon enough you'll be ready for another go, and it will last longer. When you are practicing on your own, try pacing yourself, push it close to the edge, then back off; keep it going for a while before you let it rip.

If you're relaxed, observant, communicative, quick with the lube, and can pace yourself, she'll think you're an ace.

Nomad commented on Oct 16 09 at 5:19 am

25-virgin: NW is right on. Maybe let her know you are inexperienced; ask what she likes and such. If you want to tell her outright, that is up to you. But, the whole no condom thing is stupid. I am not a 'safe sex infomercial' but condoms are essential. Yes, it will feel different than bare, but when I started having sex, the slight (and it is VERY slight) desensitization was welcome. Girls I dated did not want/request a gloved penis for oral, and it was some time before I could take the sensations of that particular act.
Oh, and a condom making you subject to a half-hard, never happened for me. Lastly, be ready with a couple of condoms, at least. If your first time turns out to be quick, being ready to go again will be appreciated.

@ Cougar: go for it! when I was 24, I met my then 36 year old wife. We dated; she tried to set me up with her 30 year old roommate. Well, I didn't want the roommate. 2 years later, we married. Now, 14th anniversary coming up... 39 and 51 and still loving every minute of it. He may just be feeling the same as you and thinking.. 'she is so great and personable and attractive. I just like the time we do get and I don't want to push it cuz then she will toss her 'boy toy' aside for a mature man she has more in common with' You never know until you take the chance...

grad student commented on Oct 26 09 at 2:56 pm

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