My 29F and I 27M engage on rather soft activities and we both we mainly use it to better our own sex: she flirts, teases and flashes other people but never beyond that really, and I'm always there when it happens. But an opportunity to take things further as presented itself and I don't know how to go about it.
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For context, I teach an evening introductory course to software development. It's pretty chill, small group of 18 to 22 year olds that want know if programming is for them or not.
One of this boys, he's probably 20 or 21, lives near me so we take the bus to class together and my gf picks us up after work and we drop him at his place on the way back. He's a little weird, struggles to socialice with the rest of the group, but he's a good kid, introverted but funny in his own way. He and his family moved from another country when he was a teen, so I guess that plays a part in him not being fully adjusted.
Anyways, we have about 45 minutes on the bus before every class, so we talk about lots of things. It was mostly about why he joined the course and class related topic, but those topics were short-lived and we quickly started talking personal stuff. I thinks he feels someone he can talk about. I know he hasn't many friends his own age, and I like him too honestly.
A while ago he started talking more and more about his struggles with girls and his dating life, or lack thereof. He mentioned he's still a virgin, that he never even frenched a girl, and how much pressure there's on him about it at this age. Let me tell you, this kid is in no way bad looking. He's more of a twink type, but I'm sure his looks are not what's holding him back, I thinks it's more a lack of confidence or experience.
Recently he's been more desperate about the subject, as he's going on his first ever solo trip soon since the course was about to be over, and I've been encouraging him to use it as an opportunity to gain experience and get out of his shell while far away from this daily life. I can tell he's exited about the idea, but even more afraid.
One day while we waited for my girl to pick us up, he confessed he was about going to a sex worker, to get it over before going to this trip. I advised against it, since I feel he's probably not getting the right support he need on that experience. And I also think that he really has every chance to get those experiences organically, again, he's young and good looking, just a matter of letting go of fear and insecurities.
Anyways, you probably can guess were this is going. I can very clearly see how he looks at my gf from the back of the car, when she said hi and when he get off at his house. A couple of days ago he told me he had been invited to a party, and I told him to let me know how it went as classes where now over and we wouldn't be meeting on the way as we usually did. So he was texting me pretty late at night, saying that he started talking to some girl but couldn't deal with the pressure and froze up. He was devastated, and drunk.
That's when he said something along the lines of "I just want to have a girl like you do" and "if I could get with a girl like that I could do anything". His intentions where very clear. And I'd be lying if I said I hadn't already thought about it. That night my girl was out with her friends, so being all by myself I started getting really aroused by that idea. I asked him if he would really think it would help, and he said that "just learning out how to tongue kiss and having a girl tell me what she thinks of my penis would change my life". The idea of this young guy putting his sloppy tongue on my girls mouth had me immediately jerking off. I was so horny that I probably let my mind get ahead of myself.
– I'll see what I can do – I texted him.
– What? – I immediately thought I was out of place.
– Would you really do that? – I felt relief, and the adrenaline I had just experienced pushed me further.
– Listen, you're a great guy and on the verge of one of the best times of your life, so if I can help I will.
– How could you help me?
– My girlfriend will help you learn how to kiss properly. And if you want, you can ask her about your other doubt.
I saw him type and delete for a while.
– Would you really do that for me? When?
I realized I needed to talk to her first, so I just replied
– Just have a good rest of the night and we'll see.
When my gf comes home after a night out, she's usually had some drinks and is super horny. This was no exception. We talk about other people a lot while we fuck, so I though this would be a great time to introduce the topic. I asked her if she found him attractive.
– He's cute – she replied nonchalantly – and a guy that tall and skinny, he's probably packing.
– He needs someone to tell him just that. Boost his confidence. Someone how can show him how to properly kiss a girl. And you're the best kisser I know.
– Yeah? You just want me to kiss him then, huh?
– I want you to do everything you want.
– How about I jerk him off? See what he's working with for myself. Maybe let him suck on my tits while I do, too.
It was melting and couldn't respond to that, as I immediately started releasing one of the biggest nuts I've had in a while.
After that we took a shower and there she asked.
– So was that just dirty talk, then?
– It's whatever you want it to be. You'd be the one doing the heavy loading.
– You know I'm well overdue for a good deed anyways. And you know I love how kind you are, so you'll get rewarded too.
– Let's make it happen, then.
Jump back to the present. Her and I agreed to no penetration. And I've told him to hang out the 3 of us this weekend. But I'm still unsure how to go about this. I want this to feel like a sort of sex-ed space where he's confortable exploring my girl's body. I feel like inviting him to our house would probably make him too nervous, so would a more public place. Maybe the car?
Have any of you had similar experiences? Have any other recommendations? I'll answer any other question and I'll give an update after it's happened.
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