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Virgin Dilemma - 5/3/2006 1:49:01 AM

merrymasochist

Posts: 156
Joined: 9/2/2004
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This one is for all you gents out there.

I've been asked by a twenty-two year old male friend of mine to relieve him of his virgin status. He's as cute as a collie pup and twice as sweet and I've accepted. He has no knowledge of my nature or tastes so it is going to be strictly vanilla. There's no romantic future between us so this is going to be a friendly thing rather than a matter of hearts.

My question is, how can I make this special for him to give him a proper introduction and send off into the delightful world of sex? I want to make it a joy for him, give him the skills that will make his future girlfriends happy and have it be something he can remember with a fond smile when he looks back on his life.

Any ideas? I've got till this Saturday to plan things out. I'm nervous as hell. I've not done vanilla in over a decade and he's the first virgin (to my knowledge) that I will ever have been with.

Suggestions would be most appreciated.

Sincerely,

merry

_____________________________

"What hath night to do with sleep?"
J. Milton

Post #: 1

RE: Virgin Dilemma - 5/3/2006 1:58:01 AM

Rumtiger

Posts: 2634
Joined: 3/4/2006
From: Vegas
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Where were the saints like you when I was growing up?

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RE: Virgin Dilemma - 5/3/2006 2:05:34 AM

merrymasochist

Posts: 156
Joined: 9/2/2004
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We were busy growing up too!

merry

_____________________________

"What hath night to do with sleep?"
J. Milton

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Post #: 3

RE: Virgin Dilemma - 5/3/2006 2:18:14 AM

GreySaber

Posts: 46
Joined: 2/27/2006
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I have a few suggestions.

First, Don't make it a one-time thing. Tell him in advance he gets a certain number, or whatever. It's a learning experience, and he's undoubtedly nervous about performance, etc. Tell him he gets to come back a few times for 'improvement.' It’s his first time, so make sure he doesn’t feel like he has to get it ALL right on the first time, and that you’ll build him to at least a basic experience level. Trust me, this will releive a huge amount of performance anxiety in him.

Second, don't just leap into bed. Go out, have a light meal (not heavy candles or anything, Chinese takeout and a skimpy outfit would be fine.) Play footsie under the table, build anticipation.

Third, be on top the first time. This way he doesn't have to learn mechanics of movement on the first go.

Fourth, Make him go down on you, and when you do use very clear verbal directions. Explain in advance how going down works on a mechanical level, and think about what sort of movements you like in advance so you have the explainations of techniques planned out. Many people don’t pay attention to what is actually being done when they get good oral, and as a result only know when it’s good rather then how to teach what they like, sinc they don't know what they like, they only know when they like it..

Other little things… If you are willing, you might want to give him a try at all the basics. Obviously vaginal, but also oral and anal. You could teach him to how to do anal without pain, teaching him to apply lube and whatnot. Some men like the idea of having tried each one at least once, and would leave him feeling well rounded. On say, the third try, you might try some odd stuff, if he’s willing. Say, the finger in the ass trick.
I’d recommend against condoms with him, if you feel safe doing that. Condoms have a very, VERY, VERY important place in the world, but they do reduce sensation, and it's his first damn time!

Making the first day be mostly about him trying things, and the second day be all about doing them right. (And tell him that in advance, it’ll make him less nervous.)

Do you think that will help?

< Message edited by GreySaber -- 5/3/2006 2:19:17 AM >

(in reply to Rumtiger)

Post #: 4

RE: Virgin Dilemma - 5/3/2006 2:24:25 AM

newdombbw

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GreySaber:

The only thing I might add is while explaining the mechanics - also mention the possibility of premature ejaculation - and that it's ok and to be expected for a first-timer. That's why he'll get additional opportunities. <grin>

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RE: Virgin Dilemma - 5/3/2006 2:27:36 AM

Wulfchyld

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I would make sure that the setting had perfect ambiance and was the most romantic you could make for yourself. He will notice and, hopefully, take notes. Start with some heavy petting before dinner. After dinner get some non-alcoholic wine/champagne and a fruit platter and move the seduction to the living room. You need to do this in a heat up and cool down pace. Let him learn where your yummy kissy/touchy spots are. Telling him will defeat the purpose and his next lover will appreciate his search as opposed to needing directions. I would then move it to the bathroom. Bathe him first, you out of the tub, for a good example of sensuality. Then have him bathe you while he is out of the tub. Again the heat up cool down thing. Move to some kissing, touching, caressing in the tub together. Once the water is boiling move to a cool down by talking about it. Now take it to the bedroom and tell him a good lover can satisfy a woman well before he wets his winky. Teach if you have to, but encourage exploration. At least make sure he can bring you to orgasm before intercourse.
Respectively

_____________________________

Loki, forum god of Mischief

Submission is not a gift... it is plunder!
Where there is a whip, there is a way!
Dom/mes of a feather, beat the f*ck out of slaves together

(in reply to newdombbw)

Post #: 6

RE: Virgin Dilemma - 5/3/2006 2:39:25 AM

GreySaber

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Oh! I just thought of something that could make him a better lover long term.

WAY back when, when I was a virgin in Junior High, I remember there was a lot of talk 'going around' in general in comedy and documenties about women not having a good time, much of it due to men not lasting long enough.

I was horridly intmidated, having no idea what was adverage and wanting to grow up to be Don Juan. Now, as it turns out that wasn't an issue for me, but I was terrified it would be. No one wants to be a minute man, unless they are fighting the Redcoats.

At the same time, I remember talk about cunnlingus. Now, I was terrified it would taste awful, instead of being the wonderful taste that it is. but I decided that I would find something I liked about it, and that I would be good at it, because I would grow to love it. As a result, I came to the conclusion that if I focused a large amount of dreaming on that, I would like it when I got the chance.

I think it worked, since I loved it when I got the chance.

Unfortunitly for the longest time I was simply atrocious at it, but I don't think that was my fault. I got bad advice from sex manuals about the amount of pressure to use, and not directly licking the clitorus because it was 'too much sensation' and to 'lick around it.' Add to this inexperinced GFs who didn't know what to tell me to do, and one who wouldn't say a thing because she hated it, (as a result of being molested like that, not that I was informed until we broke up....)

Eventually I changed tactics in a fit of anger, and got much, much better.

When a girl tells you that you are the first to ever make them really enjoy oral sex, it makes your heart glow.

So........... You might tell him that when he fantasies about sex, to ALWAYS toss in dreaming of a girl having an orgasm under his face.

QUICK EDIT, Wulf has a point about making him be able to work on you, and it's a damn good point. But there is the danger of giving him blue balls if you wait too long. Blue balls is the slang term for what happens in the testicals when a man is turned on too long without release. Sperm are released, but go nowhere, but stay in the tubes of the testicals, which frankly HURTS. Whilst I wouldn't say to go straight to it, I would say to not have him wait too long for the 'first' time.

< Message edited by GreySaber -- 5/3/2006 2:43:01 AM >

(in reply to newdombbw)

Post #: 7

RE: Virgin Dilemma - 5/3/2006 3:00:25 AM

Level

Posts: 25145
Joined: 3/3/2006
Status: offline

quote:

ORIGINAL: merrymasochist

This one is for all you gents out there.

I've been asked by a twenty-two year old male friend of mine to relieve him of his virgin status. He's as cute as a collie pup and twice as sweet and I've accepted. He has no knowledge of my nature or tastes so it is going to be strictly vanilla. There's no romantic future between us so this is going to be a friendly thing rather than a matter of hearts.

My question is, how can I make this special for him to give him a proper introduction and send off into the delightful world of sex? I want to make it a joy for him, give him the skills that will make his future girlfriends happy and have it be something he can remember with a fond smile when he looks back on his life.

Any ideas? I've got till this Saturday to plan things out. I'm nervous as hell. I've not done vanilla in over a decade and he's the first virgin (to my knowledge) that I will ever have been with.

Suggestions would be most appreciated.

Sincerely,

merry

First off....... I'm nominating you for the collarme person of the month award......

Now...I would disagree about what was said about not using condoms.... I would get him used to the idea of using them right off the bat. Yes it cuts down on the sensation, but trust me, it will feel wonderful to him, especially as it's his first time.

Make love to him.... don't just make it a quickie. Lie in bed naked with him, and go over some of the basics... show him where things are lol.... don't assume he knows much of anything. As the others have said, let him know it's ok for him to cum quickly, that time and a bit of effort will take care of that... and explain to him how women are usually different in terms of cumming and orgasms....

I think he's a lucky young man.

Level

(in reply to merrymasochist)

Post #: 8

RE: Virgin Dilemma - 5/3/2006 3:13:04 AM

ClassAct2006

Posts: 318
Joined: 4/12/2006
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I can't see how you can't not use condoms, sadly. He might say it's his first time and it might not be, he might have HIV etc etc.

Ideas? Like most of those above. Help him understand women's sexuality and how to please them which some men never get the hang of. Presumably he'll come too soon so do it a second time slower. Talk to him about it and what women like, what men can do, educate him in general.

(in reply to Level)

Post #: 9

RE: Virgin Dilemma - 5/3/2006 3:20:45 AM

Wulfchyld

Posts: 2618
Joined: 12/7/2005
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Oops, I missed the no condom suggestion. Very bad idea. By all means use a condom. If he has an inflate a date at home have him use condoms on that too! Just like Oral Roberts said about the poor… “If they never had steak, the wont miss it.”

He can and will enjoy you with a condom more than he have realized and there is no sense in getting him set on sex without them.
Respectively

_____________________________

Loki, forum god of Mischief

Submission is not a gift... it is plunder!
Where there is a whip, there is a way!
Dom/mes of a feather, beat the f*ck out of slaves together

(in reply to ClassAct2006)

Post #: 10

RE: Virgin Dilemma - 5/3/2006 3:33:24 AM

GreySaber

Posts: 46
Joined: 2/27/2006
Status: offline

Personally I say if it's his first time, give him the full experince. Others disagree with me, and they have reasons I cannot help but have great respect for. They are good reasons. Nonetheless I do think the first time should be the full experince. In the end though, it's your choice to make.

(in reply to Wulfchyld)

Post #: 11

RE: Virgin Dilemma - 5/3/2006 4:03:29 AM

shygirldesires

Posts: 53
Joined: 10/2/2005
Status: offline

merry...
you rock...i am VERY jealous...

send him my way or lead me to him and i will be his next

shy, DB's cumslut

_____________________________

"We choose our joys and sorrows long before we experience them." -- Kahlil Gibran

(in reply to merrymasochist)

Post #: 12

RE: Virgin Dilemma - 5/3/2006 5:47:07 AM

LuckyAlbatross

Posts: 19224
Joined: 10/25/2005
Status: offline

It's his first time, what more do you need to make it special?

When I am with a virgin, I actually do everything I can to make it a casual, comfortable, NO stress environment. The act of losing virginity is more than enough in itself. I tell them not to worry about whether they are doing anything right, not to worry about how long they take or what reactions they have- just to feel what they feel and to go with it.

First time experiences aren't the time to compete in the Olympics or judge yourself or have any actual expectations. It's the time to just experience what it is that they are experiencing. They are usually clumsy, quirky, and hopefully fun times to remember.

_____________________________

Find stable partners, not a stable of partners.

"Sometimes my whore logic gets all fuzzy"- Californication

(in reply to merrymasochist)

Post #: 13

RE: Virgin Dilemma - 5/3/2006 5:48:55 AM

LuckyAlbatross

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Joined: 10/25/2005
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quote:

ORIGINAL: GreySaber
Personally I say if it's his first time, give him the full experince. Others disagree with me, and they have reasons I cannot help but have great respect for. They are good reasons. Nonetheless I do think the first time should be the full experince. In the end though, it's your choice to make.

Yeah cuz that whole pregnancy and exposing yourself to disease thing is definitely part of the full experience of losing one's virginity.

_____________________________

Find stable partners, not a stable of partners.

"Sometimes my whore logic gets all fuzzy"- Californication

(in reply to GreySaber)

Post #: 14

RE: Virgin Dilemma - 5/3/2006 6:02:16 AM

MstrssPassion

Posts: 2444
Joined: 1/1/2004
From: West Palm Beach, FL
Status: offline

I read over the responses & one thing came to mind.

You say you want to make this special, give him experience he can carry over to future girl friends & such...

This guy is going to be imprinted by this experience, if you send him to the moon with toes curled as an experienced sex partner... this poor kid is going to have a tough time chasing that high when he goes out with others girls that may be lacking experience.

It could do him more harm than good.

I say this because I have been with partners that were not necessarily virgins but they were rather inexperienced. I have never lost touch with these men over the years. (as mentioned in another thread about staying in touch with previous partners) These men have told me repeatedly that they have never had another partner make them feel like that again.

_____________________________

MstrssPassion

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Post #: 15

RE: Virgin Dilemma - 5/3/2006 6:18:37 AM

kisshou

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I don't think you should do this since you and him are not in love with each other.

(in reply to merrymasochist)

Post #: 16

RE: Virgin Dilemma - 5/3/2006 6:52:54 AM

TolerableCruelty

Posts: 447
Joined: 2/4/2005
Status: offline

I say go out and grab some grub, have a few drinks ( no more than a 6 pack for him, though)... then just have some laughs, get naked, and enjoy the hell out of the next 30 seconds of ecstasy !!!

once he's caught his breath.... repeat as necessary throughout the night until you see daybreak... make it a night to remember for him

T.R.

(in reply to kisshou)

Post #: 17

RE: Virgin Dilemma - 5/3/2006 6:55:33 AM

withsmooches

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merry, what a lovely thing to do and so thoughtful of you to look for advice to make it special for him.

whatever you do it will be special - we all only have one "first time".

i may be in the minority when i agree with saber about no condom - it saddens me that this generation has to experience everything through a sheath of latex - you know him better than we do and if you feel safe then by all means let him truly experience the joy of your body.

also pointing out the naughty bits and letting him experiment is a terrific idea - reading and looking at video is no substitute for hands on exploring.

just one girl's humble opinion!

(in reply to kisshou)

Post #: 18

RE: Virgin Dilemma - 5/3/2006 7:10:04 AM

merrymasochist

Posts: 156
Joined: 9/2/2004
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Dear Everyone,

Thank you very much for the advice and suggestions thus far. Y'all have given me a lot to think about and a lot of ideas to run with.

GreySaber - I'm not planning on it being just a one shot deal, just for as long we are comfortable being together. Rome wasn't built in a day and neither are good lovers. Heaven knows it took me quite a while with a very honest and patient gent to learn how to get things right. Your mechanics advice and suggestions to have him try everything make a lot of sense. Truthfully I hadn't thought that far ahead but your ideas are sound. I may be back for more suggestions on how to introduce the more exotic things. (Well, they'll seem exotic to him anyway.) As for going down on me, I figure to have some chocolate sauce on hand or some other tasty just in case.

Wulfchyld - I'm not sure how romantic I want it to be for we aren't romantically involved. But I do see your point at creating a good atmosphere. I don't want to overwhelm him though as I think he's going to be nervous enough without making things too elaborate. Your bath/massage and warming/cooling periods ideas are terrific and will make us both more at ease.

newdommbbw - I figure he's going to be fast the first time so I'm planning on enough time for at least three goes the first meet if he's able and willing. I'm hoping that will be enough to get him to slow down to enjoy what's happening and perhaps learn a little too.

Level - You've just put me to blush.

As far as I know, most of all he knows of the mechanics has come from porn so I'm not going to assume anything. From a guy's point of view of a first time, would it better to lead his hands to the right spots and what feels good or should I just let him roam at will and applaud in the best way when he hits the hot spots?

shygirldesires - I'll mention you to him.

As for the condom debate, I'm still thinking about that one. Everyone has made some excellent points on the subject. I'm on the pill and do full check-ups twice a year so I know I'm safe and clear. Part of me wants to give him the full no barriers go. The other part of me believes strongly in condoms and the protection they offer. I may just split the decision and have foreplay and oral condom-free and when it comes time, just mouth-slide one on him at the last minute for the act itself.

I'm going to be talking with him Friday to sound out just what he would like to happen too. That way if there are any ideas or wishes he has in mind I'll see what I can so if it's within my abilities and means. A little wish fulfillment is a good thing.

I'm just afraid I'm going to imprint him with my likes and tastes. I -like- unnecessary roughness but there's the fact that many women don't like it. I can and do enjoy levels of pain that many wouldn't go for. In short, what works and works well for me doesn't exactly fit for the mainstream populace. Is there a way to know how to scale back? I don't want his next girl to be saying "ouch" instead of "oh yeah."

Please keep on with the ideas and thoughts. They are helping me tremendously. Thank you all who have responded so far.

Sincerely,

merry

_____________________________

"What hath night to do with sleep?"
J. Milton

(in reply to shygirldesires)

Post #: 19

RE: Virgin Dilemma - 5/3/2006 7:44:44 AM

merrymasochist

Posts: 156
Joined: 9/2/2004
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LuckyAlbatross - Good points. I've always held to the belief that sex is one of the last true playgrounds for adults and should be as anything-goes, relaxed, joyful and playful as it can be.

MsstrssPassion - You've hit the nail on the head of one of my greatest worries. I'm not exactly a beginner's model but I'm the one he's chosen. I don't want to hold back because I don't think that's a good way to begin but I also know what I like and can do is not what he's going to find in his age group.

kisshou - I respect your opinion. Sex with love is one of the greatest things in life, but I'm not going to pretend something we aren't. It took a lot of courage for him to sit down to talk and ask me for this and while we not be each other's happily-ever-after love, we are good friends and respect each other.

TolerableCruelty - Wheeeeeee!!!!!!!!

withsmootches - As I said before, I'm still debating this.

Thank you everyone. The thoughts, ideas and points are great. Please keep on.

Sincerely,

merry

_____________________________

"What hath night to do with sleep?"
J. Milton

(in reply to merrymasochist)

Post #: 20

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