Kind of a weird question for these parts

[Ruth2301]

Hi everyone...long time reader, first time poster...

Here's the deal: I'm a 38 year old woman with a very healthy sex drive, but I'm a virgin. By choice. Lots and lots of choices for lots and lots of reasons.

Last night I shared this little fact with my boyfriend, but it was coupled with the fact that I'm ready to make a new choice. I mean...it didn't quite come out this way, but I basically said, "I want you to fuck me, but by the way I've never actually done this before."

So anyway...he was great about it, and I'm sure we'll get there, but it's probably going to take some time, all things considered.

What I'd like from y'all are some tips on how to make it easier on him.

Physical, psychological, whatever...

I mean...do I find someone else to break the ice on his behalf, and teach me a few things? That seems like a bad idea...and yet...

Help me, oh wise ones!

 

[backslash]

Hi everyone...long time reader, first time poster...

Here's the deal: I'm a 38 year old woman with a very healthy sex drive, but I'm a virgin. By choice. Lots and lots of choices for lots and lots of reasons.

Last night I shared this little fact with my boyfriend, but it was coupled with the fact that I'm ready to make a new choice. I mean...it didn't quite come out this way, but I basically said, "I want you to fuck me, but by the way I've never actually done this before."

So anyway...he was great about it, and I'm sure we'll get there, but it's probably going to take some time, all things considered.

What I'd like from y'all are some tips on how to make it easier on him.

Physical, psychological, whatever...

I mean...do I find someone else to break the ice on his behalf, and teach me a few things? That seems like a bad idea...and yet...

Help me, oh wise ones!

The "finding someone else" thing, unless he's down with that, sounds like a very bad idea unless you want to send him packing.

Personally, I don't see the big deal for him. Aside from going slow (at least at first) and respecting your wishes if you want to stop at some point, it shouldn't be "weird". Hell, I think you need to point out the one big benefit to him - you have nobody to compare him to, so even if he's not that good you won't know any better!

 

[elite2013]

What Backslash said.

Just jump into bed and let nature take its course. Might be worth using some lube incase you feel a bit nervous and don't get fully wet, but lots of foreplay should mean in it's not really needed.

 

[Ellafun]

Communicate, communicate, communicate. If you and your boyfriend are at a point in your relationship where you have complete trust in each other you should be able to tell him exactly what you're thinking, what you want, what feels good, what hurts...speak up! I'd be willing to bet that he's anxious, excited and just as nervous as you are! Take your time, and above all else, COMMUNICATE!

 

[boutrosboutros]

Speaking as a man, if your boyfriend is really into you and you, him, your first time should be with him. And he'll love the fact that it is and that you shared that intimate moment with him. I think it would be a very bad idea, to say the least, to "find somebody else to break the ice on his behalf"!

 

[fire_breeze]

Hi everyone...long time reader, first time poster...

Here's the deal: I'm a 38 year old woman with a very healthy sex drive, but I'm a virgin. By choice. Lots and lots of choices for lots and lots of reasons.

Last night I shared this little fact with my boyfriend, but it was coupled with the fact that I'm ready to make a new choice. I mean...it didn't quite come out this way, but I basically said, "I want you to fuck me, but by the way I've never actually done this before."

So anyway...he was great about it, and I'm sure we'll get there, but it's probably going to take some time, all things considered.

What I'd like from y'all are some tips on how to make it easier on him.

Physical, psychological, whatever...

I mean...do I find someone else to break the ice on his behalf, and teach me a few things? That seems like a bad idea...and yet...

Help me, oh wise ones!

Welcome to Lit

And no, it's not that weird of a question. We got weirder.
As Ella said, communicate, communicate, communicate. Talk to him before, during and after.

And going with someone else - not recommended. Sex is about intimacy, about communication, and what better to explore sex than with a caring partner? How about he teaches you a few things? And besides, it's not like being a virgin is a big deal - everyone was one at some point.

 

[Ruth2301]

Thanks everyone (and keep 'em coming!).

Don't worry...would never seriously consider going to someone else. How would that conversation go, exactly? "It's okay, honey, I took care of it. You're good to go, now!" LOL

I guess it's really about wanting to take the pressure off him, too. I mean I'm not naive enough to think we're going to necessarily get it right the first time, but I have plenty of time to improve. I am, after all, frickin' awesome.

100% will be using the line about having no one to compare him too, though. Fantastic.

 

[Hoselvr6164]

Communication with your partner during sex is vital. Help him out by telling him when he is doing something you really enjoy, but also let him know when he's doing something you don't like. It's best to do it in a way that gives him a suggestion on how to change what he's doing, rather than simply saying "you're doing it wrong."

Good luck, and report back here....after.

 

[Aphro]

Hi everyone...long time reader, first time poster...

Here's the deal: I'm a 38 year old woman with a very healthy sex drive, but I'm a virgin. By choice. Lots and lots of choices for lots and lots of reasons.

Last night I shared this little fact with my boyfriend, but it was coupled with the fact that I'm ready to make a new choice. I mean...it didn't quite come out this way, but I basically said, "I want you to fuck me, but by the way I've never actually done this before."

So anyway...he was great about it, and I'm sure we'll get there, but it's probably going to take some time, all things considered.

What I'd like from y'all are some tips on how to make it easier on him.

Physical, psychological, whatever...

I mean...do I find someone else to break the ice on his behalf, and teach me a few things? That seems like a bad idea...and yet...

Help me, oh wise ones!

How is being your first lover going to be difficult on him to the point you feel you may need to ease that burden? I would think he'd feel quite positively chuffed at the thought of taking your V-card. I mean, I am assuming he is approximately your age, give or take a few years either side? Not many guys in their mid to late 30's get the opportunity to be a womans "first" unless they are going far too young in the dating department.

I don't think you need anyone but him to teach you a few things. It will all come quite naturally as your physical relationship develops. The first time may be a bit awkward, but a sense of humour is a great thing, so my only advice is not to take yourself, or the sex too seriously. This is meant to be fun!

That being said, I will forwarn you that my first time was quite the anti-climax, both literally and figuratively, so don't be disappointed if the earth doesn't move under you. I mean, I can only imagine how you may have built the whole thing up after 38 years!

He's not a virgin too, is he?

 

[backslash]

The first time may be a bit awkward, but a sense of humour is a great thing, so my only advice is not to take yourself, or the sex too seriously. This is meant to be fun!

It's worth noting that even for non-virgins, the first time can STILL be a bit awkward as you get to know what the other person likes/doesn't like, since everyone is a bit different. That's part of the fun, really (finding out what the person likes, not the being awkward part ).

 

[amofiga]

I'd say that the obvious thing is to be totally honest with each other. I suppose that goes along with the "communication" thing mentioned several times earlier.

I don't know what you were referring to about "somebody to break the ice". Are you talking about someone to literally penetrate you for the first time or just to give you some pointers on foreplay or what to expect from the actual intercourse experience? There's no way of knowing how much of a "virgin" you really are. Have you been living in a convent and had next to zero experience with men or are you a "technical virgin" despite considerable other experience? I knew a girl many many many years ago that was a "technical vaginal virgin" but was pretty experienced with oral sex and anal sex. Assuming that you truly are relatively naive about sex, then you should really trust your boyfriend about what to do and let yourself be uninhibited enough to learn from him. He may be thrilled to be the teacher of a relatively innocent woman rather than being told what to do by one who has a well defined set of expectations.

The most important thing I'd say was to trust your body that all will be ok and not fight it. It's like being a passenger on a motorcycle. Go along with the ride and trust the guy in front and don't try to resist too much or "drive" the action. Let him know what you really feel but trust that he will make every effort to make it as good an experience for you as possible. He's probably reasonably experienced and not some greedy horny teenager that only has one thing on his mind. Keep your expectations realistic. Often the first time isn't the bells, sirens, and whistles presented in romance novels. The important thing is that you share openly with your boyfriend. If you respect and care for each other, that will make it good for you no matter what.

 

[SkylarFalling]

Yeah as above, I've got no idea how much you would actually know already... The main thing is communication, and I think that as you're (presumably both of you) older than most when they lose their virginity, the communication thing is gonna be a lot, lot easier.

I apologise sincerely if I'm telling you something obvious (this will be, if you're not - for want of a better word - dildo-virgin) but queefing is ok!

I tell you this because I was pretty well prepared for my first time and this was pretty much the only thing I had no idea might or even could happen, and I was really mortified, to the point where I kind of think if I'd only been allowed one piece of advice after "use a condom", it'd have been "you don't have to feel like curling up in a hole and dying when you discover what queefing is".

I mean, I'd been lurking around dark places on the internet (like here ) for years before I had my first time and I'd never even come across it. I don't know how. But I would not like someone else to discover what queefing is on their first time because I thought that was a pretty horrible way to discover it.

I probably sound like a nutcase, and you were probably well aware of it already, but just in case, I hope you know I'm a well-meaning nutcase. Good luck and have fun. The better you get to know each others bodies the more fun it will become.

 

[NippleMuncher]

If he truly cares about you, then he's going to be extra gentle and go slow. Absolutely insist that if you need to stop, that things stop upon your command.

As was said, whether it's your first time or 400th, the fact that you are a new partner to him, it will essentially be his "first" as well, and there may be awkwardness involved just because you are both new to each other and inexperienced with each others needs, tells, desires, etc.

Just take it slow, don't expect a lot of romance or earth shattering excitement. Try to relax, enjoy the moment and the experience. As both get to know each other better, the sex will definitely improve.

Oh, and this is definitely one of those occasions where the more you practice, the better it will get. Just be open and honest with each other before, during, and after, and take your new found knowledge forward into your next adventure together.

Good luck and please report back with your experiences.

 

[silverwhisper]

ruth, you've gotten some very good advice already and i can't add anything new, just wanted to add my voice to the chorus. :>

ed

 

[subdued_passion]

Hi everyone...long time reader, first time poster...

Here's the deal: I'm a 38 year old woman with a very healthy sex drive, but I'm a virgin. By choice. Lots and lots of choices for lots and lots of reasons.

Last night I shared this little fact with my boyfriend, but it was coupled with the fact that I'm ready to make a new choice. I mean...it didn't quite come out this way, but I basically said, "I want you to fuck me, but by the way I've never actually done this before."

So anyway...he was great about it, and I'm sure we'll get there, but it's probably going to take some time, all things considered.

What I'd like from y'all are some tips on how to make it easier on him.

Physical, psychological, whatever...

I mean...do I find someone else to break the ice on his behalf, and teach me a few things? That seems like a bad idea...and yet...

Help me, oh wise ones!

As a 38 year old virgin shouldn't you be more worried about making this easier for yourself?

I mean physically, psychologically, whatever...

 

[Ruth2301]

Thanks, everyone, for your wonderful advice. I would have come back sooner but I was...uh...busy

I suppose some details are in order, given the crowd...

It started innocently enough: we were just sitting on the couch, enjoying a little time together. I was a little buzzed, but that was just the whiskey doing its job. He asked what I wanted to do with our evening, and I responded that I’d mostly just really like him to have his way with me.

Turns out he'd been doing a little preparing himself, and had decided that this should really be all about me. So after we made our way to the bedroom and successfully removed one another’s clothes, he scooped me up, set me down on the bed, and tied my hands to the headboard and my feet (loosely) to the base. This itself is a pretty huge turn-on for me for so many reasons, but I have to say that the best part of this portion of the evening occurred when he was straddling my upper body, reaching forward to put my hands where he felt they belonged: his rising cock made for a pretty nice view, and I may have reached out for a little taste.

Anyway, from here he proceeded to explore and touch my entire body, stopping to focus on a few areas of particular sensitivity, and to express appreciation for the sights. This effectively removed any remaining nervousness on my part: by the time he reached my clit I had thrust my hips in the air and was about as wet as I'd ever been. From the slightly predatory look in his eyes I think it was his plan all along to have me begging for it. And I was.

The rest is a bit of an extended blur, to be honest. There were multiple finger fucks, some serious work on my clit, and a few pauses for a little eye contact. And at one point he took the time to run his tongue from my raised hips, up through my neck, in agonizingly erotic slow motion. This action also gave him a nice opportunity to begin to tease my pussy with his dick. “Desperation” might be the best word to describe my state at that point.

When he finally got to easing himself into me, I was pretty much putty in his hands. There was a little discomfort, but he was gentle and slow, and of course it had already been a night of many orgasms: my body was ready for nothing but to have him inside me. As he entered it occurred to me that he had been hard the entire time, enjoying himself (almost) as much as me. Which of course just made me open my hips all the wider, and gasp a little louder. Holy. Fuck.

So really…no complaints. He’s a giver. I’m an up and comer

 

[subdued_passion]

Thanks, everyone, for your wonderful advice. I would have come back sooner but I was...uh...busy

I suppose some details are in order, given the crowd...

It started innocently enough: we were just sitting on the couch, enjoying a little time together. I was a little buzzed, but that was just the whiskey doing its job. He asked what I wanted to do with our evening, and I responded that I’d mostly just really like him to have his way with me.

Turns out he'd been doing a little preparing himself, and had decided that this should really be all about me. So after we made our way to the bedroom and successfully removed one another’s clothes, he scooped me up, set me down on the bed, and tied my hands to the headboard and my feet (loosely) to the base. This itself is a pretty huge turn-on for me for so many reasons, but I have to say that the best part of this portion of the evening occurred when he was straddling my upper body, reaching forward to put my hands where he felt they belonged: his rising cock made for a pretty nice view, and I may have reached out for a little taste.

Anyway, from here he proceeded to explore and touch my entire body, stopping to focus on a few areas of particular sensitivity, and to express appreciation for the sights. This effectively removed any remaining nervousness on my part: by the time he reached my clit I had thrust my hips in the air and was about as wet as I'd ever been. From the slightly predatory look in his eyes I think it was his plan all along to have me begging for it. And I was.

The rest is a bit of an extended blur, to be honest. There were multiple finger fucks, some serious work on my clit, and a few pauses for a little eye contact. And at one point he took the time to run his tongue from my raised hips, up through my neck, in agonizingly erotic slow motion. This action also gave him a nice opportunity to begin to tease my pussy with his dick. “Desperation” might be the best word to describe my state at that point.

When he finally got to easing himself into me, I was pretty much putty in his hands. There was a little discomfort, but he was gentle and slow, and of course it had already been a night of many orgasms: my body was ready for nothing but to have him inside me. As he entered it occurred to me that he had been hard the entire time, enjoying himself (almost) as much as me. Which of course just made me open my hips all the wider, and gasp a little louder. Holy. Fuck.

So really…no complaints. He’s a giver. I’m an up and comer

Seems like there was a mix-up, should've posted here.

 

[jollyball]

do I find someone else to break the ice on his behalf, and teach me a few things?

Hi Ruth,

Congratualtions and welcome to the club ...of pleasure

Glad he made it easy for you. Perhaps when you get comfortable with him after another few round of creating the 'backosaurus' you can do something nice for him ;p