Need Advice for My Sweet Friend

so yeah, i’m not much for asking for advice.

not because i’m perfect or genius but because i usually only write about things where i’m the expert. and that’s ok.

it’s also ok to say hey. what do you say to this dude. i’m at a bit of a loss for words.

there are 2 issues going on. they may be related, but only distantly. either way, they came up around the same time the other night.

we had another bra-less party that turned into a bit of a sex party on saturday. it was full of weird shit. booze, pot, chicks with assertive nipples and the men who love them.

i fucked no one, but i watched 3 orgasms, including one penetration event that made me want to cum right there. but i didn’t. i was the host.

but there was an afterparty. as there always is.

and a sweet dude friend of mine was the last one to be awake with me. on my bed. just talking. he lacks confidence. not that there was going to be the sex with me, but still. confidence thing.

within a few minutes of each other, these 2 things came out.

1. in grade 5, he did something bad in school. no memory of what it was. he was generally a good kid. still is! but he got yanked out of the classroom where his nazi teacher started tearing into him…for whatever the thing was. she was tall and imposing and generally mean anyway. once she got a few sentences in, he peed his pants. right there in the corner of the hallway outside the classroom. i asked what he did after that. he guesses that he went back into class. he must have smelled like pee. everyone must have known, but he has no memory of that. but i don’t see how they couldn’t. no other memories of that day. no surprise there. amazing that he didn’t block that out. in fact, blocking that out would have been awesome. but it’s tormented him for almost 2 decades. so my question for advice is below. now read the next thing.
2. we were also talking about things that were demeaning to us. sexually. i have a bunch of stories from university. i had low sexual self-esteem. boys did degrading things to me. not on my terms, unlike now. 🙂 but i have recovered my sense of dignity from those events. my sweet dude friend, though, is similarly tormented by this sexual encounter. despite it being different from the pants peeing, it has the same effect on him. he was dating a girl in university. she worked in the library [not a student] and he was. they would watch movies at her place. sitting on her bed [studio suite]. he liked her. she was sexually self-determining. he was happy to get any kind of making out. but he was lacking confidence to “make a move” on her. so sweet! at any rate, they had a respectful friendship, with attraction. one night she “made a move” on him. she reached over and held his hand and said she wants to have a good time now. he blushed and kept telling the story. she started kissing him and rolled on top of him. grinding and going mmmm when he rubbed her ass. she talked dirty to him, “squeeze me, bitch” and “what are you going to do with that cock, you girlyblouse”. she took off her top and pants and helped him take off his clothes. but then she wouldn’t touch him. she lied there and when he touched her belly she grabbed his hard cock and squeezed. he winced and she said, there’s a price for touching her. so he had to think about that. hard, because all his brain blood was in his penis. so he rubbed her belly again and she squeezed him again. huge price for any contact. he thinks, how will he ever get to make the sex with her if she keeps squeezing his penis. good point. next move: he rubs a breast, over her bra. kind of hard. and yes she squeezes again. all this is new for him and he’s wondering how much touching her he can do before she squeezes off his penis. next: breast under the bra and pressing her nipple. squeeze, still the same amount of pressure. thank god, i guess. next: he pulls down the top of her panties, fast, to reveal her bush. squeeze. he lets go. then he moves around in position to pull her panties right off. i remark that that sounds really bold. and he’s like, yeah. if he’s going to be hurt he wants as much as he can get for it. i say that sounds very transactional. so yeah, he pulls her panties off next. she sits up reach for his penis for the squeeze. he gets them off eventually and when he stops touching her she lets go. she lies back. he pushes her legs apart, far. squeeze. then he lies down between her legs with his face close to her cunt. and he watches her box. she seems to be pretty solidly not moving, just letting him watch her cunt as her body breathes and her lips get more flushed. and he knows she can’t reach his penis in this orientation. so he puts his finger about a centimeter in front of her labia. he moves it up and down without touching her. this is fun for him. and her. he brings his finger back and kisses her cunt. he gets about 2 seconds there, feeling the warmth of her cunt and she leaps up and jumps at his cock. squeeze. 2 seconds, harder now. she ends up lying on the bed in a loose 69 orientation, with his penis within her easy reach. and her cunt is close to his face and hands. he pushes her legs apart again. squeeze. he spends a bit more time looking at her close up labia and bush. breathing her in. then he dives in. fingers rubbing and pulling her labia [squeeze], finger into her vagina, in and out getting creamy [still squeezing his penis], then his tongue on her clit just pressing but no flicking [constant squeeze now] and he just wants to stay in this position until…..he dies of pain or something else. after a few seconds [or hours in non-linear sex time] her hips pull back, he pushes his finger further up her vagina, and she moans a bit [all while squeezing]. at the moan, he cums. despite her squeezing. and he describes this cum as “trying to get your whole body through a basketball hoop.” ok, right. not the clearest analogy, but i get the point. hard to push the cum out of a squeezed penis. “but once it got out it was magic.” and his penis softened a bit and was less pained by her grip. did she cum, i ask. “yes?” he suggests. typical. 🙂 juuuuust kidding. he’s a sensitive, giving man. and i ask what happened next. he said he was stunned because she didn’t wipe up his cum or dry up her creamy cunt. [not everyone worships kleenex] she just hopped up to the top of the bed, slid under the covers and called him up to get in there with her. and they watched tv. touching, hugging but no sex or other sexy acts. while he wonders if he should have tried to fuck with her, he is most “disturbed” by all that squeezing. that she wouldn’t “let” him have contact with her without there being a price. i said that it was a game. he wonders if i might be wrong and he’s right in presuming she wanted to hurt/oppress him and dangle her sex in front of him to be able to control him. i said the snuggly behaviour after he came shows she was in it for play. he mostly believes me. but i’m not going to try to fight to convince him that i’m right. so i’m crowd sourcing your wisdom.

so. my questions.

1. what would you say to him about holding onto this self-torturing memory of peeing his pants in elementary school?
2. and, vote on library girl: just playing or trying to degrade him?

i encourage/welcome your responses in the comments!

make my/his day! 🙂

i love you all!

in touch,

holly