The 28 year old virgin

[Der Cute]

SGA:
I'm going to assume you've had enough time to pleasure yourself. You're 28. You've had the teen hormone flux..and you get so koo-koo it's not funny.
Ok, my thoughts.

The advice so far about using other items (vibrators, dildos, stuff. )and things to practice with are very very smart. You can observe (somewhat) how those feel and the size of such.
Don't be concerned so much about the hymen, it's a body part. It DOES mean a milestone being a virgin. BTW, I didn't have mine when I lost my virginity. Somehow it was gone. I think the Hymen Gremlin took it. (tampons don't break it, horseback riding CAN). Ok. It IS a milestone, and for you, I think it would kind of emotional; in the sense you want someone that cares a lot to be allowed in, and to "deflower" you (can't think of a better word).
Because you're have emotions about it (this is an assumption on my end, but I think I'm kind of accurate, correct me if I'm not), you have the chance of getting MORE attached to the person who has the privilege. Most women are already somewhat invested in emotional attachment when having sex. Along the lines of "I trust, I care, I like, I'm letting him". Be careful. Understand this please before you go any further than heavy petting. Many men (not all, and this IS a psychology truth) are along the lines of "Ok, I care somewhat, but I'm not truly attached at this point." (Neanderthal males were 'procreate' and females 'nest'. It hasn't really changed much)

I know my body very well. I've kind of had to because of lifelong illnesses, so I like to know what where that those. I'm not ashamed or embarrassed about genitalia, body parts, bodily functions etc. Not saying you are. But I have met a LOT of people who don't know diddly. Explore yourself BY yourself. Explore yourself WITH someone. Know thyself. Shit, go read http://en.wikipedia.org/wiki/Masters_and_Johnson ... it may be dry and technical, but it give you an idea.

Go slow as you start. (but your hormones are going to be going nuts). If it's painful or you feel uncomfortable or it's irritating, say stop. Stop means stop means stop.

Have faith in yourself, trust in him, and say "we need to stop" if you need to.

Hugs

[sms001]

The lady is also talking about driving everywhere all night after we leave the club

Glad your original plan is back on track.

uhm.....
Hate to sidetrack but does coworker lady have a DD? (Her hubby?) I hope so.

[ShinyGreenApple]

That was another thing that concerned me. I've never heard of the guest of honor/host BEING the DD, and I don't know her well enough to know for sure she won't get trashed at the club I've never met her husband and Biscuit has only briefly met him, not long enough to form an opinion on the guy. I trust myself not to drink at least until we're safely at a place where we can crash. If Biscuit truly wants to get wasted, (although it doesn't sound like he plans to), that's fine with me so long as he doesn't puke in my truck

Der Cute, thanks for the thoughtful input, I have considered the emotional risks long and hard ( no pun intended ) and it's a risk I'm willing to take. If it leads to something more, that's great. If it's a one time thing, well, that's too bad and I only hope it won't make things too awkward between us.

[Victory Sabre]

SGA -

I'll preface this by saying that I'm a guy who doesn't have much experience with the ladies, and all of mine was way too long ago. He's a very lucky guy to be your first. Just take things slow, and do a lot of "prep" work before the deed.

I've never had the honor of being a lady's first, and probably never will. If the chance did come up, I'd be honored like you wouldn't believe.

[ShinyGreenApple]

He was trying to see if we could meet for lunch today, but he was already back home by the time I got his message. But he was trying to meet me. On his day off. That never happens, you guys. Um wow, this is new ...

Anyways we at least settled it that we're driving just the two of us alone so we're not stuck. He's never kept in daily contact with me before. Until this past week.

[xx_wolfie_xx]

He was trying to see if we could meet for lunch today, but he was already back home by the time I got his message. But he was trying to meet me. On his day off. That never happens, you guys. Um wow, this is new ...

Anyways we at least settled it that we're driving just the two of us alone so we're not stuck. He's never kept in daily contact with me before. Until this past week.

Sounds like things are going great! Enjoy yourself

[Der Cute]

This sounds more like dating than plain (uh, adjective?) sex. From here I'd go slower. Yeah, I said slower. Why? Remember the emotional stuff upthread. My logic here is this: You go date. You hang out a few weeks, and hold back on the sexual stuff. Is he going to have sex and bail? You start getting attached (you). But can you read a person if they're getting attached? I can't.
Ok, live life, doo de doo, a few dates, a month or two, trust built. Then you decide to have sex. This is a very tricky part (ooh bad bad pun sorry). With your HEAVIER emotional investment it's gonna be extremely sad if he up and leaves. I have seen /heard of couples/people doing that. A man chases a woman, they decide to date-ish and then have sex. Once he's had her, he bails. That is my cynical part, and it's concerned about you.

So, you can "feel" him out MORE if you take it slower. Let's say you go hang out for lunch. He asks you for it again. Ok, lunch and chatting. You get together for dinner later that week/month. Sounds good. At this point I'm going to assume you've got a crush (more than today's) on him. This is where you have to find out wtf is going on in his head. Is he starting to get more attached to you? (gah, get help on the body/voice/speech thing here I can't give any advice on how to tell). Is he RESPECTING you? By this time he'd have hinted about sex or R-rated subjects. So you go and decide to do it. Is he respecting you after? Is he concerned about your well-being right then? Good.
That is more emotional investment, but it's also sussing out if he's interested, and if you still trust him for this. I mean, let's say you have sex tomorrow for the hell of it. So how does he treat you afterwards? Are you really ready for a one-nighter?

I know. Yeah. Such a messy emotional bodypart aaaaarghghghghgh! When I lost mine, I'd had that boyfriend for a month. (I was in school, ok, forgive me). We had our fun, and afterwards he avoided me for a good while. Then I was his booty call. Take into consideration I was a teen, so was he, our hormones were WHACKED, and my emotional/executive thinking/dating experience was crap at the time. After a time, I told him to bug off.

Get this. YEARS LATER, I'm an adult, living on my own, doo de doo. HE CALLED ME AND LEFT A MESSAGE ON MY MACHINE. Seriously? Teenager sex, wait 5+ years, call me out of the blue??? That's chutzpah. I ignored the call(s). <<<<<< that is not normal. Just an anecdote about being a booty call.

Oh. Use protection. He has to, someone has already said bc hormones take 28 days to set in. Have it within an arms reach, in sight. Don't keep it in a car, or squished in a wallet. I had wayyyy too many scares of pregnancy as a teen. Shit, even as an adult. That's proof there that your thinking when aroused isn't so good. That's how I got pregnant; J and I weren't thinking much besides having sex. I now have a 2 yr old. I'm 37. J and I were irresponsible, and we have a kid.

I hate emotions. I sooo much prefer logic it's nuts. Right now, just enjoy life.

[Greenday]

Kinda surprised no one else has said it, but I don't think doing it after a night of drinking is really the best of ideas. It has the potential to make the first time a bad time and pretty much ruin sex. What if he gets whiskey dick? What if he forgets to be extra gentle? Personally, when I drink, I take a lot longer. Not really a big deal these days since my partner enjoys long sessions, but for my first time, I'm glad it wasn't a long affair.

As far as telling him you're a virgin, I'd definitely mention it before the session even starts. Have a conversation with him at some point, somehow get the topic on sex, and then mention never having done it. If I was messing around with some woman and thought it was going to lead to sex, then she mentioned she was a virgin, I'd be thrown off. I've taken a few women's virginities and I've introduced a fair amount to the fun of being sexually active in general. It wouldn't bother me if I knew before hand, but it would be a big shocker if they just blurted it out in the middle of doing stuff.

[ShinyGreenApple]

Der Cute, he and I have been doing the lunch thing for a while now. We usually go around once a month or so, sometimes there's another person, usually either my bestie from pharmacy or his brother, but mostly it's just the two of us.

I probably should have mentioned this in my OP, but when I said I have a friend I like very much, I meant it in every sense of the word, I like him very much. He's divorced and hasn't been in a committed relationship in at least three years or so, and seems to keep walls up, so to speak, emotionally. I'd love for this to go someplace, but well, it's been two and a half years. At this point I figured I'd been Friend-zoned and that he would always be 'that' friend, the one who is frustratingly attractive and easy to get along with, but that it would go nowhere. But no matter how many times I've come close to not letting myself get into him emotionally, I've never been able to turn off the sexual attraction, ever. I can't even watch a porno clip without the guy somehow turning into him, sometimes it gets incredibly frustrating, LOL.

Ok, so at this point, I figure he's a very open-minded guy. If there is anyone I could have a 'casual' encounter with, yet trust enough to teach me things, it's him. So when he brought up this whole go out next weekend thing, I was like ok, he'll get a little tipsy, maybe we can go somewhere with this. And again, I will NOT try to seduce this man if he's three sheets to the wind and obviously not in his right mind. That would just be gross, or like Greenday said, he could have whiskey dick or all other manner of disgusting things that happen when we get too torn up. Also, would I like it if someone (even if I *was* interested in them) messed around with/took advantage of me when I was effed up/passed out? No, I'd lose all trust and respect I ever had for that person. I was thinking more along the lines of a few drinks, like a couple of rum & cokes or something like that.

That being said though, he seems to have thrown in a bit of a wrench here, insisting he really doesn't want to get wasted with these other people, when I know for a fact that he usually enjoys crazy shit like that. Then there's the daily little texts and teasing on FB. Sunday I was just going to wave at him and go inside to work, but he checked the time and said "I know you have a few minutes before y'all open. You can sit." And then he was wanting to see me today, on his day off, when that's another thing that never happens, it just doesn't. If we can't make our schedules work together to meet for lunch, he doesn't go out of his way to meet.

So I have no idea what to think and I'm really looking forward to Saturday to see what happens. And yes, if it's clear he wants to try being more than friends, I definitely agree with postponing the sex, as it would obviously have more meaning if we're both more emotionally attached than we would have otherwise been. I mean, either he really does have to know I like him at least a little bit. I've given him compliments, and there have been a few parties where we both had a little too much and I either ended up glued to him with my arms around his neck or like that one time, asleep in his bed. On my birthday I flat out slapped his rear end and then grabbed a big handful of it and he clearly still talks to me, and that was months ago

But yeah . . . it's all a little confusing.

[NorthernZel]

Just chiming in with a little tidbit:

Supposing that everything goes alright, the both of you agree to commit to a relationship and therefore will have a whole lot of intimate moments together, your thighs CAN and WILL be sore for the first couple of months. So make sure to do some exercising!

(Take it from me and Mr. Zel - going up (or down) the stairs to (or from) 5th floor was a drag the first month we were together )

[PepperElf]

It sounds like your relationship is going at a pace you're mostly comfortable with - and it sounds very sweet. :congrats:

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.

This. It sounds trite but if he cares for you anything close to what you feel for him, this won't drive him away. It may make him nervous - but perhaps in the "I hope I do it right!" kind of way.

(My first was very nervous and a bit scared about hurting me).


Also... if you have time before your first night, I'd recommend talking to your doctor or ob/gyn... not just for pills or birth control advice, but to make sure your other concerns [blank](mainly your concerns about breaking the hymen and the tightness)[/blank] can be addressed.

Also, as others have said, I recommend investing in some lubricants. Being your first time, I wouldn't recommend anything crazy (like tingling or warming), just something that's either water-based, or silicone-base. The latter is longer lasting. Glycerin-based can be OK too, but be careful since they can encourage yeast.


But above all... communication.
Communication is the riskiest thing you can do with your partner really... but it can also be the most rewarding.

[Gizmo]

I know I'm late to this thread but TMI {self play isn't always the same so don't expect it to be the same and don't worry too much about the tightness issues. The human body does know the difference and can react differently.} Still tell him and still be careful and go slow but allow your body to lead you on what is ok and not. Also I suggest having lube available - sometimes even if you are 'responding' well it can be beneficial.

[PepperElf]

I know I'm late to this thread but TMI {self play isn't always the same so don't expect it to be the same and don't worry too much about the tightness issues. The human body does know the difference and can react differently.} Still tell him and still be careful and go slow but allow your body to lead you on what is ok and not. Also I suggest having lube available - sometimes even if you are 'responding' well it can be beneficial.

good point on the blank stuff.
[more blank]also, the canal will widen as your arousal increases, so don't feel wrong about wanting more foreplay... it can help prepare your body more adequately[/blank]

[LewisLegion]

Ehn, I just turned 37 and I'm still a virgin...though no longer 'physically' thanks to a couple of darned intra-uterine ultrasound I had to have.

I have never hidden the fact, and a SO should definitely know. When the time is right for you then it's right for you, if not then it's not. At least if he knows, he can take that into account and not scare/push you too hard. If he cares about you, he'll be respectful and patient about it.

My virginity has lasted as long as it has because I only very recently came into full realization that I'm gay. Any man I was dating that even got close, I physically couldn't stomach the idea of actually 'doing it'. Now that I'm with my girl, it's just a matter of time

[Seshat]

You can practice 'loosening up', either on your own or with him. Fingers or toys, with generous amounts of lube. It will also help you - and him - learn what angles are likely to work well for you.

Each woman has a slightly different internal .. 'layout' of nerves, and slightly different size and shape. So we're all unique. Let him know what you enjoy, what you don't enjoy, and if anything hurts. (For example, some people enjoy having the cervix touched, some are 'meh', and for some it's as cringeworthy as a baseball to the balls for a guy.)

You won't know what's right for you until you try, so consider getting a good book of ideas and suggestions, and .. well. Playing.