I need some help. I have a friend who just got out of the navy. He was very shy in high school, and really hasn't changed. He's 41 now, says he never had time for the ladies. Long story short, we got us a 41 year old virgin. I'm looking to get him a little experience so he'll loosen up and eventually meet someone. Any ladies wanna pop a cherry? Here's the basics: he's black, 5'8" and muscular. He's good looking with a great smile. Like I said though, he's VERY shy. So I need someone who can take charge with him. If interested, message me and I'll send a picture of him.
seems a little fishy, 41 year old virgin that "doesn't have time for the ladies"to top it all off he's in the navy. Sounds to me he prefers the seaman...pun intended.
Haha, gay jokes, navy, very clever. I really do appreciate you attacking my best friend who is lonely, and at his age feels like love just isn't in the cards for him. But if getting it out here will keep a puppy from getting kicked, than its ok. He's not gay. He uses that as an excuse to not face his fears. His shyness is paralyzing to him. He just needs confidence.
Why don't YOU 'do the deed'? I mean you're a swinger and stuff so you shouldn't have any moral qualms about fucking another guy...and if he's super shy, meeting (and fucking) someone he doesn't even know might be very stressful for him. Seems to me that having a trusted friend pop his cherry would make the situation far more comfortable for him and even sort of special in that his first time would be with someone he knows and trusts. You could even continue fucking him in a FWB type situation to give him more experience and confidence until he's ready to fly on his own. Alternatively you could take him over to Nevada and hire a pro who has probably successfully de-virginized a LOT of young guys. I could be wrong (usually am) but it seems like having his 'first time' with some random swinger chick could be a little too much for a super shy guy who's never had sex. 
DELICIOUSLYWET wrote:
We are all individuals and life rolls out differently for all of us. It is hard not to see other people wanting major events to happen, in their lives, much the same as we want or wanted them to happen for us. I have never been a 41 year old virgin or a man that is overly shy. Shy people are often sensitive and I can relate to being sensitive and enjoying the ability to feel and especially to have feeling for people. Many people and maybe more often than not, most sensitive people would prefer to have sex the first time, with someone they care about in at least a crushy or love struck sort of way, but it often happens in a manner a bit more random than that and it can still be fun and enlightening.
You two know the dude and are talking to the dude, and with him being one of your best friends you have a better idea than we all do about what makes him tick. Guessing, and realizing I am only guessing, it seems that perhaps, the lady should be a gentle sensitive sort of girl herself, that can take some time to let him feel comfortable, and yet have the ability to start taking his and her clothes off once the time seems right. First time perhaps, should be a bit more multidimensional for your friend if that is possible. We all sometimes know someone that we think might like someone we know and we might even encourage a meeting. Is there a lady you already know within the community, that you think might hit it off with your buddy physically and socially just enough to make his first time special?
Makes the most sense that mrs encore takes the task on.
Wow, some strong opinions here. I'll try to answer each one. First, Mrs encore and I have decided it's not a good idea for her to do it. Like delisiouslywet said, you don't know our situation and the choices we've made, so no, that's not an option for us. And I know him. He can either hope someone in this repressed state will take charge enough to get him out of his shell, or I can approach a community that I hoped wouldn't be judgmental of him. (Or me). Give him some experience so eventually he can feel confident enough to approach a woman. If you don't agree, that's fine. There are plenty of topics to weigh in on.
Encore wrote:
Haha, gay jokes, navy, very clever. I really do appreciate you attacking my best friend who is lonely, and at his age feels like love just isn't in the cards for him. But if getting it out here will keep a puppy from getting kicked, than its ok. He's not gay. He uses that as an excuse to not face his fears. His shyness is paralyzing to him. He just needs confidence.
We're not attacking anyone, we were thinking you might not have considered the possibility that your best friend's shy and not having time for the ladies might be his subtle way of telling you he's not interested in the ladies. There isn't anything wrong with that.
Mistress Wanda will take GOOD care of him! GROVEL, WORM!
Wait, which of his cherries did you want popped?
Wait, which of his cherries did you want popped?