The 28 year old virgin

[Cookie]

In regards to the TMI (highlight to read):

It's not always about being relaxed enough. Some women have a lot harder time with initial penetration than others. Once you get there, it's fun, but it can be a gradual "stretching" process that might happen over more than one session.

It this happens, it doesn't mean anything is wrong with you. I was in tears after a few times trying to figure out what was wrong with me. The answer? Nothing. Go easy on yourself.

[ShinyGreenApple]

I had the same thought about the change of venue thing So the whole shebang, as it were, might not happen after all. But we can still do lots of fun stuff without penetration Truth be told I think I'd feel better doing this after I get on some kind of oral contraceptive, anyways. If we broke a condom it'd freak me the eff out and I'm not ready to deal with that.

Really though, wow you guys. I was afraid this was going to be a really awkward discussion but you all have been so supportive and helpful, thanks so much!

[Dasota]

I've got a friend that only until recently was a virgin. Just something that I learned through her experience though, don't hold it against him if he chooses not to have sex with you once you tell him, and do tell him before the clothes come off or before the heavy petting even, but depending on folks tolerances, one or two drinks into the night might make folks more at ease.

If you're close friends, see if you can slip it casually into a conversation that you're still a virgin and gauge his reaction. If you like the reaction, then pursue him then. For my friend it backfired when she tired to bring it up casually as they were getting hot and heavy.

TMI to Follow:

If you want to avoid any of the mess of the breaking hymen during intercourse, I'd highly suggest getting a small vibrator or dildo and having fun with yourself before trying to break your hymen or practicing getting used to penetration itself. It'd be a good idea to go slowly of course and let yourself have a go more than once before trying this by the way so that you are fully relaxed

[iradney]

Whatever you do, make sure he wraps his tool. It's better safe than sorry - birth control pills prevent pregnancy, not STIs.

[BookstoreEscapee]

Well since we're doing TMI, I've never been comfortable with tampons, either, but that hasn't been a problem in, um, other areas, so I wouldn't worry too much about that. But also what Cookie said.

[Andara Bledin]

The hymen isn't a solid barrier; it's got openings, and just being able to insert a tampon won't ensure that you can fit larger items (such as boyfriends ).

One thing I can't stress enough is to have a good lube on hand. You don't have to use it, but if you don't provide enough of your own physiologically, you will both be better off if you have a little extra help in that department.

Also, if you're worried about comfort, or fit, you can do a little digital penetration to start and get your body ready for more intimate activities. This will actually serve several purposes; stimulation, checking readiness, as well as increasing readiness.

It's worth noting that a woman has a limited amount of space available, but as she becomes more aroused, that space becomes less constricted. So going in cold would be a much more difficult task than going in after things have heated up sufficiently.

^-.-^

[ShinyGreenApple]

Oh there will definitely be a condom, whether there is BC or not. But yeah, I really, really would like some BC. I just dread the doctor's visit required to get them. I already know that's not an issue with him because hey, he doesn't censor himself - I know so much personal crap about him it's not even funny, just because it comes out of his mouth. He learned his lesson about wrapping it when he was 17. He's still paying child support for that lapse in judgement. He takes no risks now.

More TMI, yay! The lube is a good idea, although I'm not sure it'll be a necessity. I've always felt I'm so like a guy in that it doesn't take much, if ya know what I mean. Last time I stayed over with him, I was having, erm, issues and all he'd done was turn over and put his leg between mine in his sleep I was thinking FFS this isn't even funny at all, I'm gonna need to change my underwear when I get home.

But yeah . . . I'd really rather not do this in someone else's bed, that's just kind of gross. But hey, I'll try playing around and if we like the samples, he can always take me home for a full course later

Gods, we're all disgusting.

[Andara Bledin]

I'll counter your TMI with some TMI on my part: I don't need it, myself. Normally. However, there have been all-day make-out sessions that have required a little assistance in that department round about the, say, 10-hour mark. Also, consider having a towel or two on hand or in place.

And, on that note, be sure to keep a glass of water, juice, sports drink handy. Dehydration while doing physical activities takes away from the fun.

^-.-^

[Flying Grype]

Tell him when you start discussing the idea of having sex with him. If he rejects you on the basis that you're a virgin, he's not the guy you thought he was, clearly.

I can't think of any other reasons to NOT tell him beforehand, and plenty of reasons why you should tell him.

Now adding more TMI to the pot...

Lube is gooooood. Get good lube, not drugstore stuff. Go to a sex shop that's female-friendly, and tell them what's up. They'll help you out.

Hymens: I can't help you there, I lost mine to a toy when I was twenty-two. Now, depending on how far in the future you expect to get with this guy, you might want to consider that route yourself. Get a toy, play with it, and get the painful part over with (gently!) while you're comfy at home. (Again, a sex shop that caters to a female clientele will be able to point you towards something that's realistically sized and suitable for a beginner or a virgin.) Do it a week or more ahead of sex with him. More time is better, but honestly I didn't notice any soreness more than a day or two after. Then when you're with another person, you can both concentrate on pleasure rather than trying to work around that particular pain.

[ShinyGreenApple]

Holy undecidedness, Batman. Stopped and talked to him before I clocked in this morning and he says he thinks he's too scared too stay at this chick's house because she keeps warning him and apologizing in advance for what she might do or say to either of us because she's a touchy-feely drunk he said his brother might could swing by and pick us up from the club, but we're thinking the original plan of just me and him taking my truck and going back to his place afterwards would be best. The lady is also talking about driving everywhere all night after we leave the club and he's not comfortable enough with then to do that and stay at their place. Frankly, neither am I, I don't want to be carted all over creation.

Yes. His place. Drinks, couch, snuggling. That sounds good.

[AnaKhouri]

Bit of a warning: if you're going on the pill, it won't be at its full effectiveness until you've taken at least one full pack (28 days). Having a condom as a backup is good but if you want super-double-protection you might want to wait a month.

[BookstoreEscapee]

Holy undecidedness, Batman. Stopped and talked to him before I clocked in this morning and he says he thinks he's too scared too stay at this chick's house because she keeps warning him and apologizing in advance for what she might do or say to either of us because she's a touchy-feely drunk he said his brother might could swing by and pick us up from the club, but we're thinking the original plan of just me and him taking my truck and going back to his place afterwards would be best. The lady is also talking about driving everywhere all night after we leave the club and he's not comfortable enough with then to do that and stay at their place. Frankly, neither am I, I don't want to be carted all over creation.

Yes. His place. Drinks, couch, snuggling. That sounds good.

Oh geez, yeah that sounds best to me. I generally prefer to drive myself places, anyway. A.) I'm not the most social person in the world so I like to have the freedom to beg off when I want to, and B.) I get carsick when I'm a passenger for too long. I'm not a big drinker, anyway, so generally it isn't a problem for me to drive.

[AmbrosiaWriter]

Here's another bit of TMI for your safety.

You've very likely to get an urinary tract infection from having sex. (Not 100%, but it's a good chance.) Just because of everything poking around down there. So, after you've finished, get up and go pee if you can. Yeah sorry it's awkward but that will flush your uninary tract so less likely to get an infection.

Trust me. You do not want one. It burns and makes your pee smell funny. >_<;

[ShinyGreenApple]

I've heard about the peeing thing, so if anything happens, I'll keep it in mind. I've had either a UTI or kidney infection before (is there a difference?) and it was the worst thing ever. Oddly enough I didn't have any symptoms when I peed, it was just the most excruciating pain in my side/back that I've ever felt, my head felt like it was going to explode, and I was extremely nauseous. No one could figure out how I ended up with it, since the test was clean, I'm not sexually active, and I drink probably more than the recommended water intake.

I'll definitely be letting him know later this week though that we can just drive, if he doesn't mind. That way we can get there when we want, leave when we want, and go wherever else we want. I don't want to be at the mercy/convenience of our co-worker, but I don't want to spoil her night, either. So it's best we all just meet up and hang out instead of sticking together all night and having everyone unhappy. Hopefully when we get home he'll offer me whiskey and coke or somesuch like he always does and we can go from there, or I'll bring rum or something. Then if things are awkward because of it, I can always blame the alcohol.

[malmalthekiller]

It seems like you're in a good place, emotionally to make this decision. I'd say go for it.

You will always learn new things about your body. I do really think that knowing what your body likes will make you a more relaxed person, and a better lover. With each person, it's brought a bit of myself out into the open.