The 28 year old virgin

[ShinyGreenApple]

Just what it says on the label, folks. Only a select few very close friends and family know this little fact about me. When I was younger, I figured I'd stay one for religious reasons, but since then I've been living WAY more 'secularly' and my personal morals are much less narrow than before. I'm much happier this way, and the reason I'm still a virgin now? Well, it just hasn't happened and I haven't met the right person, nothing more, nothing less.

My question is, though, on the off chance something does happen with someone soon, should I tell him? When? I have a friend from work that I've known for about two and a half years that I like very much. I trust him and I'm very comfortable with him. To put it plainly, I want to bed the guy, and he's very experienced. We're going out next weekend to someone's birthday party at a club and I'm his designated driver, so we'll more than likely be out until stupid o' clock in the morning and I'll end up staying at his place rather than drive home. We've shared a bed before so it's no big deal, but I'm seriously thinking of seizing the opportune moment, as it were. (I didn't try anything when I slept with him before because we were in a hotel room and his brother was in the next bed. I'm sure poor Teddy didn't want to be audience to that, haha)

I kind of think he might already suspect I've not really been around. But yeah, I don't want to get pounded to death or have him be surprised, so when should I come clean about my inexperience?

[AmbrosiaWriter]

Uhm...

Well I suggest you do it before he gets blitzed! XD

This is a bit tricky, because sometimes the information turns the guy on, sometimes it turns them off, or sometimes (I think this is the majority?) it doesn't affect them much other than they know to take it easy.

Some guys I know will actually ask the girl if they've made no indication on whether or not she's done it before but I wouldn't rely on him to do that.

My personal opinion is for you to be frank, but if you're too shy maybe you should see if he's interested in some... sheet dancing... before popping out with the information.

[Lil Bunny]

At first I was thinking you should just seduce him and enjoy the heck out of it. Then I remembered that when my ex popped the fact that he was a virgin until he met me I freaked out, well, you may not want to approach it that way.

Is it possible to start an innocent make out session and then bring up the fact that if he takes things easy, the innocent could get down and dirty? Clue him in with out just slapping him in the face that he's taking your "V card"?

Good luck! Remember to relax the best you can and enjoy it.

[ShinyGreenApple]

Him knowing to take it easy is the main thing, for me. I don't wanna just be hanging out and turn and blurt out "Hey did you know I'm a virgin? Wanna change that?" But I also don't want to have each other's pants off and announce "WELCOME TO NO MAN'S LAND, BUDDY!"

And yeah, if he has a shot or ten too many, the whole thing is pretty much off the table

It just seems odd that he's mentioned next weekend to me three days in a row and also snuck in "Oh yeah, Teddy probably won't go if he has work the next day, so you can drive us." Then even looked in my truck and said "You need to clean your shit out of here, especially if you're gonna be riding me around next Saturday." He also doesn't seem yo be fussed about staying with the rest of the group, saying that he and I will get there just whenever we feel like it.

One last thing, a few weeks ago, I got incredibly drunk and my friend took my phone away, but not before I managed to send him a message saying that I wished he was at the party with me because I wanted to "do bad things to him". He thought it was funny as hell and took it like a good sport, but still - drunk words are truthful thoughts, no?

[AmbrosiaWriter]

But I also don't want to have each other's pants off and announce "WELCOME TO NO MAN'S LAND, BUDDY!"

I'm so lucky that my glass of water was empty at the point that I read this. I scared the shit out of my dog Daisy, busting out laughing as hard as I did.

You owe her a chewie toy for the near heart attack. *pout*

Can't stop laughing...

That's not what I meant by "frank," by the way. I think the best time is when the... erm... heavy petting starts in. So prior to the pants being off, definitely.

Damnit I know so many freaking metaphors for sex I should be a romance novelist. -.-;

By frank I mean that trying to "clue" or "hint" or "imply" you're a virgin might just go straight over his head. I know if I try to hint anything at my boyfriend he often doesn't catch it. At all. >_>;

[Kheldarson]

Not a 28 year old virgin, but did remain a virgin until my wedding night.

BUT.

Kabe and I did do some things, if you will. And the conversation mostly played out as things were happening. So dating for a while, things start getting hot, I got a little worried, pulled back, and told him that, yeah, kinda a virgin. And was my intent to stay that way.

In your case, just change that last bit as needed. Could be, just slow down and let's ease into it. Or could be not tonight, want to get used to all of this first. Whatever you need at the time.

[ShinyGreenApple]

I'm so lucky that my glass of water was empty at the point that I read this. I scared the shit out of my dog Daisy, busting out laughing as hard as I did.

You owe her a chewie toy for the near heart attack. *pout*

Can't stop laughing...

Aww, I'm sorry, Daisy, I'm sorry! Poor doggy, lol.

I wouldn't really spring it on him like that, though. Seducing him sounds hella fun, although I'm sure he'll have to find out at some point. Like I said, he's had plenty of experience and if he doesn't realize, I don't want him to be, um, too enthusiastic. I guess it all depends on how he reacts and such. Hopefully he won't drink too much. Hopefully after we get home, I'll drink a little. Liquid courage and all, heh. He has to at least have some idea I'm attracted to him.

[Cookie]

I was a virgin until I got married at nearly 27, so I get the long time virgin thing. That said, I think I remember from previous threads that you're a girl? (Gonna be so embarrassed if I'm wrong here!) If you don't let him know somehow in conversation, he'll figure it out pretty soon and you wouldn't want him to freak out at that point. Not to be squicky, but the first time can be a little...messy.

[fireheart]

Not to be squicky, but the first time can be a little...messy.

It depends on whether you're physically a virgin as well.

If you use tampons, the hymen would've already been broken by now.

If you're not a "physical" virgin (i.e. hymen's intact) but a virgin in all other aspects, then by all means, it shouldn't be a huge issue.

Warning: NSFW stuff ahead! YOU HAVE BEEN WARNED

My advice in the meantime as well would be to get to know each others bodies. Thoroughly. Find out what erm...turns you on in the bedroom. Relaxing and enjoying it are key components. Also find out what turns him on. Even if you're still a virgin, if you can pleasure him in other....ways....he'll appreciate you just as much. (without giving TOO much away, let's just say that my previous relationships prior to my current one all fizzled out before my virginity was taken, but they all seemed to love it when I pleasured them in other ways...)

Also, TAKE IT SLOWLY in the "intercourse" department. I say this based solely on experience: my boyfriend and I kept adding too much on in terms of toys and whatnot too early, and found that it killed the mood. Also, unless there's a reason for you to do so, don't try woman on top until you feel more comfortable doing so.

I constantly panic about whether I'm doing enough or not during intercourse, so unless you're lying in the starfish position, I wouldn't worry about looking too inexperienced. Even just little things, like wrapping your arms around your partner (if he's on top) or reaching around to touch him (if he's behind you) are little things that can work wonders.

Obviously make sure that you're both prepared physically as well, so using condoms and whatnot. Lube might also be useful...you can get warming lube.

But yeah, explore your own body as well.

[lupo pazzesco]

I think it really depends on your personality and his. Like Cookie, I was a virgin until 27, so when I finally had someone interested in me, I had gotten to know him by that point well enough to say "So, I've never done this before, and I'm prone to freaking out"

Luckily his personality was such that he simply shrugged and went "Ok, we'll just take things as slow as necessary until you're comfortable with the next step"

And oh, dear lord, the "NO MAN'S LAND" comment, I'm SO glad I wasn't taking a sip of tea at that. As it is, I made a weird noise that startled the cats and has said boyfriend looking at me funny.

ANYWAYS, Cookie had another valid point about the first time potentially being messy, and I have to add on to that, and say it can be quite painful. If your guy knows you've never done this before, then you'll need a bit more...shall we say "prep work" to ease some of the discomfort.

Even then, it widely varies from person to person, how you're built, what kind of extracurricular activities you've done previously. No this is not a euphemism. If you're active athletically, it can play a role in how much it may hurt: i.e. gymnastics, track and field, sports, etc.

I just asked my guy how he'd like to be told the girl he potentially is getting naked with is a virgin. After reassuring him this ISN'T a trick question to start an argument, he said the earlier the better, and to be honest about prior experience if any. Definitely early on, though, because in his words "It mentally helps me prepare for how she'll react to the whole thing, and can adapt to her level of (in)experience"

Anyways. However it turns out, good luck! And above all relax as much as you can and just ENJOY yourself.

[Cookie]

If you use tampons, the hymen would've already been broken by now.

Not always. It wasn't in my case.

[AmbrosiaWriter]

It depends on whether you're physically a virgin as well.

If you use tampons, the hymen would've already been broken by now.

Not true. I've used tampons all the time when I was a virgin, and the first time I had sex I could tell when the hymen was breaking and I bled. So just because you use tampons doesn't mean that you've broken your hymen.

[BookstoreEscapee]

I would tell him when you are fairly sure things are leading up to that, but before your clothes come off. But don't make a huge production of 'preparing' to tell him. You don't want to freak him out with a "you should sit down cuz I have to tell you something and it's a HUGE DEAL but I don't want you to freak out" sort of revelation. Especially since it sounds like your attitude towards the idea is fairly laid-back...but at the same time, you don't really know how you will feel in the moment, and depending on how much importance he puts on the idea of 'taking' someone's virginity (I don't really like that concept; sex should be something a couple shares, not something one "gives" to or "takes" from the other), he might get upset if you don't tell him until afterwards. And just practically speaking, he'll know to take things a little more carefully than he might otherwise do if he thinks you have more experience.

[ShinyGreenApple]

Okay, here comes more TMI, in case anyone cares anymore.







I've *attempted* using tampons, I think twice, and both tines I could definitely feel it up there and I know you're not supposed to, so I took it right back out. When I was a teenager, I rode horses a lot, probably bareback as much or more as with a saddle. Warning, WAY TMI: highlight to read I'm not ashamed to say I, um, explore myself like a healthy person does, and I can never usually go in past my second knuckle. But maybe I'm just not relaxed enough.

Also, slight change of plans. The person organizing this insane outing is a girl from his department, whom he introduced me to today, it's her birthday. She was really great and just warned me she may get unruly when drunk no worries, we're peas in a pod in that case. She also told me not to worry about driving because she wants everyone to have fun and that Biscuit (what I shall refer to my friend as) and I can just ride with her and her husband. When we leave the bar, we're going back to her house and she's already reserved a bed and spare room for us O_O

Sad thing is, I'm mostly relieved that I don't have to drive around a college metro on a Saturday night. Bit still, omfg.

[sms001]

Hetero guy's perspective here SGA.

I've shared this experience with a couple of women and it went very smoothly.
BUT (Yeah, I'm sure no one saw that coming.) Two issues.

Physical
I'm a little concerned about the tampon and knuckle thing. Is this resistance from an intact or partially intact hymen or simply vaginal wall pressure? If the former, there may be issues with full penetration. Obviously, everyone is different, and the strength of that tissue runs the gamut from rice paper to full plate armor.
As an aside, I don't know if I fully agree with the woman on the bottom opinion expressed earlier. It worked out very well for one gf that she could lower herself at the pace and distance that she preferred and was comfortable with. ymmv. Other than that, everything FH said was spot on.

Emotional
Glad you said all bets are off if he's had too much to drink. I think I would add that this change of venue thing should probably ko the idea as well. Unless you are incredibly comfortable with this other couple, I would think worrying about what they'll hear and/or see (spotting or other "discharges"on sheets after you've left) might put one or both of you off a bit. If you have the privacy there, I'd vote for your own bed being ideal.
Make sure your guy knows where HE stands on this issue. Our culture tells men that this is a rather important step for a woman, and most of us interpret it that way (true or not) unless told otherwise. He will be likely to think that this moves your relationship to a different level so be sure to let him know if it doesn't. (If that is in fact the case.)

Incidentals
I was lucky in that the lead-ins to my experiences were (mostly) long term, with both of us planning for it well in advance. The only impromptu one was with someone who was very active and athletic who gave me about 3 seconds notice. We were poised for intercourse, and I assumed she HAD done it before, so the quick whisper took me by surprise and I didn't have any time to react differently than normal. I wouldn't recommend that if there's going to be any physical issues.
A guy with a decent amount of experience in bed with a woman he likes isn't likely to run into the problem, but there's a possibility that the pressure of the importance of this will cause psychological E.D.

So I think your best bet is the one you already seem to be leaning toward - seduction, progression, information, dénouement.

Good luck and have fun whichever course you take.