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Sex + Relationships

Real Live College Guy Joe: What to Do When He’s a Virgin and You’re Not

  Ever wonder what guys think, how to deal with them, or whether instead of listening to you, they just imagine you naked? Our Real Live College Guy Joe will answer all your questions about men and relationships with wit, clarity, grace and physical attractiveness (can you tell he wrote this intro himself?) all while imagining you fully clothed! Well, usually – he is a college guy.
 
My boyfriend and I want to take it to the next step (sex), but he seems nervous and insecure about the fact that he’s a virgin and I’m not. He acts hesitant every time we get to that point right before we are about to have sex. What’s the best way to reassure him that I am not bothered by his lack of experience?
    — Stuck at Skidmore

For inexperienced guys, the more you take control, the more comfortable he will be. You initiate the kissing, you take off your clothes and his, you fasten the leather straps – all that good stuff. Don’t tell him how he should be doing things because that will destroy his confidence. Use your hands to guide him (that’s way better), or Morse code the way he should be doing things by tapping on his buttocks. And don’t ever, in any way, bring up the fact of his inexperience. Say nothing like, “I don’t care you’re a virgin, virgin,” “Can you pass me that water bottle, virgin,” or, “Hey virgin, how are you liking the sex so far?” In all seriousness, don’t say things like, “It doesn’t matter to me that you’re inexperienced” – all that will do is remind him of his inexperience. And then, instead of a sexy hulk pleasuring you all over the place, you will have a weeping little fetus of a boyfriend who, once again, you need to rock to sleep in his boyfriend-sized diaper. 
 
Since that’s all I have to say on the matter, here are some pithy scenarios to dramatize what I mean: 

Girlfriend: I don’t care that you’re inexperienced. 
Boyfriend: (Entering fetus state) Get my diapers! 

Gf: You know, the other boys I’ve had sex with have done it like this. 
Bf: Wow, that sounds really pleasurable. Are these boys single now? 
 
Gf: I can’t decide whether to order the chicken carbonara or the shrimp scampi. 
What Bf hears: Virgin virgin virgin virgin. Virgin virgin?  
 
Now here’s what will happen if you follow my advice: 
 
Scene: Bedroom. Lit candles sit on every sill as a gentle breeze comes in through the open window. Is that a scent of cinnamon in the air? The bed is surrounded by white drapes, swaying lightly. BOYFRIEND and GIRLFRIEND lie upon the bed, dry humping ever so gently and romantically. Barry Manilow is there – singing, or not singing, it doesn’t matter. 
 
Gf: Are you ready? 
Bf: Yeah, I think so. 
Gf: (Guiding him with one of her hands and tapping with her other hand what she thinks is Morse code but is actually the beat to “Stayin’ Alive”) Oh my God, you’re so good at this [Author’s Note: Say this no matter what – even if he’s terrible].
Bf: Really? 
Gf: Yeah. Is Barry Manilow just going to stand there all night? 
Bf: Well, I booked him for four hours. 

 
So there you go. To recap: You take control. You guide him. Don’t bring up his inexperience. Also, don’t make a big deal about the whole affair. Don’t have a “DANNY’S LOSING HIS VIRGINITY TONIGHT” party cruise that you invite all your family and friends to or anything. Just, the next time you’re hooking up, if the time’s right, let it happen – with some helpful nudges in that direction from you.  
 
And if Barry’s busy, book Luther Vandross.

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