A
female
age
,
*aughtycougar
writes:I live alone, and there's a boy in my neighborhood who helps me out with odd jobs. He turned 18 two months ago. He's leaving for college in September and has been nervous about the whole thing. We were talking about it recently. I told him not to worry. He's smart and handsome (all the girls will be after him). Then he told me he had a major crush on me. Well, I was stunned, but very flattered. I suspected something like that, but it felt so sexy hearing him say it. We kissed. After that, he confessed to me he's still a virgin. He's very shy around girls. I said that's OK, not to worry since a lot of guys are. But since he's not experienced, we didn't go further. I think he was really nervous just kissing me.We definitely share some chemistry, despite the age difference. I know he wants to sleep with me, and frankly I love just thinking of it! However, I have never had sex with a virgin before. I want to make his first time memorable. I want to be a caring lover, a good teacher initiating him into the wonders and mysteries of sex. Anything I should know or keep in mind? What sort of things do virgin men need reassurance or support on? Physical or emotional things I should know? How can I best prepare him for future lovers? Also, how can I let him know this will be a no-strings-attached relationship without making him feel unwanted or used? Mainly I don't want to pressure him into a relationship--young men should sow their wild oats! At the same time, I want him to be healthy and secure for all those hot college girls he deserves to bed.
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male
reader, infamous +, writes (11 July 2009):
for this young man(in a sense), you are his golden ticket to willie wonka's chocolate factory... if wille wonka was a women... and if the factory was your goodies :) one thing i do agree with is that he will most likely shoot off a round faster than a western sharp shooter in a gun fight, SO tell him to use condomns or to pull out. second, give him tips here and there while in the act and when he does something right just plain out moan in pure ecstacy. tell him how good it feels and that will give him a major confidence boost. after the lessons, pointers, and tips and hes got it down pretty good, and he gets tired and sweaty, you should take over and just rock his world. use your arsenal of the sexual things you can do to give him an orgasm that will send his mind spinning out into space.you are givin this guy a great opportunity so dont let him forget it.oh oh oh and have fun
A
reader, anonymous, writes (10 July 2009): Just show him where the hole is - all the rest is of no consequence to him. Honestly. That's the truth.
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A
male
reader, anonymous, writes (10 July 2009): Since he is a virgin he may come early. This is opposite of how it is for women; less experience means faster orgasm. Let him come quickly the first time, but show him how to last after that. This alone will make him a standout on any college campus.
Flip side of the coin he will need less time to recover. Make sure not to just have sex once. He will probably be ready to go again soon.
Also show him basic anatomy of a vagina. He may only have seen female genitalia in textbooks and porn. Show him where the clit is and how to use.
Enjoy!
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A
female
reader, eyeswideopen +, writes (9 July 2009):
 Why can't I stop thinking about Rod Stewart..and somebody named...Maggie?
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A
female
reader, babymama99 +, writes (9 July 2009):
 LOL,
The ladies are saying "are you crazy - leave him alone"
The guys are saying "are you crazy - go for it!"
I think I'll stay neutral. :)
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A
male
reader, anonymous, writes (9 July 2009): i am 18 and i lost my virginity to an 40 year old who lived near me,, she didnt look that old but she was AMAZING and i knew we were only sex buddies so to speak... and nothing more just tell him that im sure he wont mind just having sex with u,, he will love it i asure you
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A
female
reader, Honeypie + ♥, writes (9 July 2009):
 HE will not get the no-strings-attatched. If he was a little experienced then maybe, but the guy has a serious crush on you.
It's a nice fantasy. And honestly he could do a LOT worse for his first time. BUT the whole Mrs. Robinson (The Graduate) seems a little wrong. I do believe in the first time ought to be done with love. With someone special. You think you can be that one?
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A
female
reader, anonymous, writes (9 July 2009): Teach him how to deliver a beautiful passionate kiss for all those lucky ladies, but thats it. By sleeping with him in this way you will hurt him; he has said he has "FEELINGS" for you, don't mess with his emotions by leading him on. Also don't you think a first time should be about an emotional connection hopefully in a first relationship?? Or at very least with someone his own age?!
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A
female
reader, anonymous, writes (9 July 2009): I'm not sure that having sex with an 18 yr old guy with your maturity is a good idea...just because it may well be frowned upon in your neighbourhood...plus at that age he could beome emotionally dependent on you.
I think the one thing you could definitely help with is drumming into him the importance of safe sex - a condom is a must if you're all for encouraging him to "sow his wild oats".
Also one thing men his age lack sometimes is respect for a woman; you could teach him respect and emotion - these all heighten the act of lovemaking. Although I don't condone you actually sleeping with this young man, it's your decision; just make sure you understand possible implications of doing so and you practice safe sex.
I personally think you should leave his virginity to be taken by a sweetheart at college and you could help his first experience go well with advice, not actions.
Best wishes.x
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A
male
reader, Beingblack  +, writes (9 July 2009):
 Ha! I like your name. Naughtycougar. COUGAR! You acknowledge what you are.
When I was 19, I was having a fantastic fling with a 36 year old. I was not a virgin, but our different levels of experience meant I might as well have been. She taught me so many things ..... damn!
So I wouldn't worry about anything you are about to do, except the reaction of his parents. I think that everyone can remember their first time, good or bad. It was special as long as the person you had sex with was special. He clearly thinks you are special, so he is far more worried than you are.
Many mature women want to seduce young boys. As far as I am concerned, there is not much wrong with that. If it were the other way round, (older man, young girl) I would have something to say. It feels perverse, though it should possibly not be viewed as worse than anything a 'cougar' might do. See what happens. Have a good time.
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