A very sweet boy hits me up and directly asks me if I’d take his virginity. His bio says he’s 19, but he later tells me he’s really 18 and hasn’t fixed the error on his social media. We talk for a while, I’m hesitant about the arrangement. He’s a nice boy, kind-hearted, socially awkward, and nerdy. I can see why he’s having troubles, especially with his glaring lack of confidence. He says he’s ready but he never makes it to First Base with a girl before they blow him off; this is not surprising based solely on how he presents himself when he feels uncomfortable. I invite him over after we speak on the phone, if nothing else I’m going to give this kid some tips on how to be a little more approachable for the ladies. I have suspicions he may be autistic or have some kind of mild mental illness that prevents him from getting over the emotional ugly-duckling stage we all go through around age 12.
He comes over and we sit on the bed to talk. We talked for probably 2 hours. Mostly I let him speak and I kept a running log in my head of the things he needed to work on to come across better. The first thing I critiqued was his insistence on pushing how ‘weird’ and ‘strange’ he is; he’s not either of those things, he just word-vomits when he’s nervous. I give him the pointer that even if you are weird and strange, you have to up-sell yourself to make a positive impression. I get him talking about things he’s done that are interesting- he’s got some stories! If you have to repeat “I’m just so weird” over and over, it’s forced and not organic. It’s ok to be weird, it’s ok not to be weird. Just be yourself and own it, but don’t sell somebody on the weirdness. Sell them on your greatness. Cliff jumping in Hawaii? Yeah, talk about that- not how you scared off therapists when you were a shitty teenager. We’ve all got shitty teenager stories- they can’t be the pinnacle of your personality or you’re either a potential mass murderer, or a complete asshole. He tells me he wants to join the Navy next year… DEFINITELY TALK ABOUT THAT. I encourage him to join sooner, it would do him some good to get out of his comfort zone. Also I’m a sucker for uniforms.
Next we need to work on body language- the kid has had darting eyes for most of our conversation, or he’s looked down and away when being spoken to. This will not do. I tell him eye contact is extremely important in engaging another person, and if it makes you uncomfortable to make eye contact just focus on the space between the eyes. I tell him a way to keep himself in check with this is to operate under the assumption every person he speaks to is deaf and you must face them so they can read your lips. Don’t turn away when someone is speaking to you, and look them in the face when you speak to them. He thanks me for what we’ve talked about so far. He’s such a gentle soul. We also work on body blocking to give the visual cues you’re receptive and not closed off. He moves stiffly and awkwardly as I uncross his arms and tilt his body to face me, I tell him the best way to keep yourself from closing back off is to throw one arm behind your head. Now he looks relaxed, he looks engaged, he looks kinda sexy.
We keep talking, and I’m sure to give him positive feedback for maintaining eye contact and keeping his body in check. He tells me he’s actually looking through my glasses- good job! Good!! I tell him any girl he gets in this scenario is going to feel he’s listening and interested. He is listening, he appreciates that I’m taking the time to give it to him straight where he’s missing the mark and shooting himself in the foot. He tells me he’s never kissed a girl, I ask him if he’d like to with me or if he’d like to save that. I understand either way. He wants to learn, he wants to be a good kisser for a girl he has feelings for later. I understand completely! Before we get to that point, though, he needs to get over his fear of making a move. I reach over and place my hand on his hand, and I gently move my fingers around his palm. Gentle, simple, not too forward. He tells me it feels nice. I tell him it should feel nice, and if he gets this kind of contact with a girl he cares about and nothing else- he should be grateful and appreciate it. This is intimacy. This is what it feels like to just enjoy someone’s company and touch, without any expectations of anything else. No pressure. I put my hand back on my leg and tell him it’s his turn to make the first move- just do what I did. He’s stiff again, his arm moves robotically over to mine. Once he starts stroking my hand softly he loosens back up. Good! See how easy it is! I put his hand back on his tummy and tell him to do it again. This time he’s much more fluid, more relaxed. Yes. Good boy. Now it’s time to kiss me.
I tell him to kiss me he needs to come to me; he moves forward eagerly and we very awkwardly brush lips a few times. It’s ok to need some work, we’ll get through it. Gently and persistently I get him to open his mouth and explore different ways of kissing until he gets into a groove. His hands start moving on my body… the natural instincts are kicking in. I can already tell he’s not going to be a bad lover, he just needed the right nudge. We’re up on our knees kissing and pulling each other into more passionate embraces. We get undressed. He’s not acting nervous, he’s not stiff and robotic, he’s excited and comfortable. The sex itself was not as quick as I thought it would be, and it was pretty enjoyable; he figured out a rhythm right off the bat and took my direction well. I got off twice. It helps he’s also not poorly endowed. He says nothing and we just kind of slow to a stop, I ask if he’s came and he says yes. Ok, so I tell him to withdraw before he gets too soft and the condom slips off. This is to protect both of us. He does as instructed and we cuddle up to talk about it.
The first thing he tells me is he loved it. Sex is great. He’s a fan. Then he tells me he wants to do more things, more positions. Ok, no problem kiddo- we just have to wait until you reboot. Surprise, his refresh rate is instantaneous. New condom, round two. He wants me on top to start, I’m alright with that. I get into my groove and get my rhythm going, he gets into me getting into it and starts moving with me at the right times. Quick learner. I tell him to get behind me and he complies- this position is great with him for sure. I end up needing to take a break after a while because he just isn’t getting off and my lady parts can only take so much. We talk some more. I give him some more sage like advice regarding dating and relationships- like, there is no ‘friendzone’ and women don’t owe you shit. There is not a single scenario that another person OWES you sex, so don’t treat them like they do. I also give him the tip that no matter what they say, or how they say it, or when, strippers do not like you. A kid this sweet and gentle could very easily get eaten alive. I tell him the only truly effective way to keep from being a Daddy is to use 2 methods of birth control- one for him (condoms) and one for her (birth control.) He tells me this is better advice, and more informative, than anything he learned in Sex Ed in high school. You’re welcome! We have sex one more time on our side, and switch into on my knees. He gives me some hand action for a while which felt good but got too rough and I had to tap out. We snuggle and sleep, and everything is wonderful. In the morning he leaves when he’s supposed to, and tells me he’ll be in Anchorage for a couple more days before heading back home to the peninsula if I want to teach him anymore things. He tells me he thinks he might become a sex addict, that this is his new obsession. He thanks me for everything I’ve done for him, and informs me he feels like a whole new person. I’ve made him a man. A real man- one with confidence. He reminds me he’ll come back and visit me on leave from the Navy so I can play with his buttons. I’ll see you again, kid! Now go slay those ladies and live your fucking life to the fullest.