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

How did you find me?

My wordpress stats are always good for a hoot.

Here I am, trying to find things to do in the next several days to ward off the start of school [denial, i know], and i’m trolling my stats for the search terms people use to get to…me. Here are the best of the 1’s [spelling is, of course, optional!]:

Search Views
braless at church 1
sex girls 1
fucking pose & tips 1
how to introduse your swettie to anal sex 1

Braless at church. I’m so impressed that anyone would think to google that. How awesome!

In touch,

Holly

Even Christians Need Gaydar

I had the mildly unpleasant duty of telling my friend Charlotte that the boy she has a crush on is gay. Bi, at the very least.

Not that there’s anything wrong with that… 🙂

Being bi myself, I can’t really judge Charlotte’s boy at all. But the unfortunate part of all this is that Charlotte assumes everyone at her church is straight…because they’re at her church.

Being Christian doesn’t mean you’re straight. Most Christians are straight because most people are mostly straight.

Christians at conservative not-so-gay friendly churches are not allowed to be gay. And if they are, as long as they don’t partake of any gay sex, they’re technically not sinning.

Christians at progressive, liberal churches can be as gay as they like.

But my dear Charlotte has liked this boy for some time now. She’s spoken of him often and last sunday I attended her church, mostly to see this dude. She insisted I wear a bra, btw.  🙂

So in about 10 seconds after meeting this guy, I knew he was gay. And he, of course, doesn’t know she has a crush on him. I can’t tell if he knows he’s gay or if he’s just ok with being who he is. He just seems to like Charlotte. And why not. She’s awesome.

But the assumption that males at conservative churches are worth being attracted to because they’re not gay for sure, is a bad one. It means girls don’t have to cultivate gaydar. This can be a debilitating disease.

Now, our agenda is to figure out why Charlotte is falling for a gay guy. Has she done this in the past? What has been her relationship like with her father? Is she looking for a safe guy to avoid real sex pressures or actual commitment?

These are the questions we are now talking about.

And maybe I’m reading too much into it. Maybe Charlotte just lacks gaydar. But either way, we’re going to get to the bottom of it!

In touch,

Holly

Why I’m Only a Bit of a Prostitute

Prostitution. I’m in favour. To not be is to be a hypocrite. But with limits.

Last weekend i spent a wonderful time in Kelowna. At the Delta. A big ass expensive hotel, with nice sheets. But sadly, not a view of the lake. For me anyway.

Technically, I was a prostitute. I was driven in the fellow’s car, had my meals and the room paid for [tho his business covered the room], enjoyed the gifts of lingerie and a summer dress, and got fucked a number of times in exchange.

I returned home with no $100 in my purse or anything tho. So technically… 🙂

But beyond technicalities, I hooked.

The guy was no stranger. He is the separated husband of a woman who taught at my school until last year. She was hard core in the micromanaging, cold fish, control freak way. She didn’t “get” students. And their need to not work 100% of their lives. They had been together for about 9 years. Married for  5. He got over her intensity and dumped her.

He works in branding/marketing. Two things I REALLY don’t like, but I like his body. And he’s really funny.

Over the weekend, I learned his soon-to-be ex was an intense fucker. Intense like at school. Liked to suck him till he came, then get him hard again and make him work her until she came. Sometimes more than once.

So I did a bit of that. He enjoyed parts of the weekend doing the exact same stuff he did with her, but with the difference being me and my body and my style. Same process, different content he called it. These marketing people, eh! 🙂

But my highlights were my times to explore what of him i’d always found attractive.

I wore no bra in the car and took off my panties on the highway. Did some rubbing in the car, of me, not him. My breasts and my clit.

And when we checked in i walked into the bathroom, into the shower, turned it on and wet me and my dress all up. And he fucked me all wet on the bed. That started the weekend well.

We got some room service and drank a bit, then he went out to the casino with some clients/marks.

Around 1130pm he phones me and asks if it’s ok to have some boys over to the room. I say sure. Committed to not fucking all 3 of them. And I didn’t, but I know that was a thing in his mind to see if it would end up there. Saucy man.

We all had drinks. They were generally polite, asking what I did, etc., but not so much about how me and “John” met. I guessed he told them, but I don’t think they know much about his marital past. New clients, or newish.

And then they left and I stripped and tied up John and gratified myself beside him on the bed while seeing if he’d cum. Nope. Good boy. Then I ordered pizza.

And while I opened the door only enough to bring in the pizza, John wasn’t so sure I wouldn’t fling the door wide open for delivery boy to see. Cue the porn music. I don’t know why he was worried. Maybe because that’s what I said I’d do with the door.

Bitch?

Bitch.

Whore, too.

Saturday, John’s is in conference/meeting/sales/branding/inspiration mode. I miss him all day. Sniff. I got shopping with his two . There are only 7,000 stores on Harvey. And one thing I love about the OK is that wearing a bikini around town, in the Subway, in the mall, is a uniform for some and not a problem for anyone [outwardly anyways].

And when I was in Sweet Dreams there were 3 girls [and by girls I mean 18-20] trying on things. One ended up quite high maintenance because each of the 3 of them and the staff sweetie all had different opinions about her “real” bra size. Clearly she had never had a proper fitting before. But after 19 million opinions she got some truth. 38C not 36D. That was fun to watch. But in the end she had to come to terms with not self-identifying as a D.

After the fitting and more hijinks and tryings-on, I mentioned to her in the corner how I’m a B. And while it’s not size that matters, it IS what you do with it. And I went into my stall and tightened up my bra one clasp and came back out and said that this difference makes a dull evening at the bar quite unpredictable. Then I went back in and loosened it to one clasp too loose and came back out and said, same for this. in a different way. It’s all about how you introduce your breasts to the world. And then I said I’d still fuck a penis regardless of which way it curves. FTW.

Anyway, I came away from there with this:

It’s a nice piece. Feels smooth. So picture this without the discrete bra and panty underneath it and that’s what i wore the rest of the weekend when we were in the room. Lots of access. And it got good and creamy.

Spent some time in the pool and sauna, got a bit frisky with myself in the sauna. That was nice. Then around 430pm John comes back to the room and I model my outfit for him. I ensure some time demonstrating the sheerness with which to see my nipples. And how I can untie the top to pull out a boob for him and rub a recently released cock head on it. And how I can lie back on the bed and push the skirt down to cover my cunt but not hide its terrain. And how I can sit on the back of the couch with one foot up there too showing how such a little skirt allows his cock to rub along my lips while I rub his balls. And how I can hold his phone and take a short video of his cock rubbing my sticky lips [not inside my cunt, mind you, because that would be fornication] and how for all day he hasn’t been able to fuck me that as i pull off the shoulder of my top and push his fingers onto my nipple, that he can cum on the outside my cunt and cream the skirt.

Then we dress for dinner, coMMANdo! With me in a navy sheer top over a cream cami and yoga skirt.

We came back to the room and slipped into the tub for a http://www.soapymassage.com. Me likey.

For breakfast, I sat on his face and he ate my cunt. Then I wouldn’t fuck him. Just kept saying no until it got so late we wouldn’t have enough time to get down to the restaurant to eat before his session. Cutting it close, I made him fuck me fast so we’d still be able to rush downstairs. But I took the poke up against the window with my yoga skirt up in the back, wondering how many people out there were drifting off to find a good local church. No one looked up and stared, though a few did glance up. They weren’t obvious though if their looks lingered.

After a quick tidy up we breakfasted and I swam and we checked out cruised a few girlclothes shops until I found a great summer dress with which to drive home in, coMMando! Of course.

He dropped me off and I felt nothing like a prostitute. I felt like a girl on more than a one night stand. It lasted 3 days, but it was much like a one night stand, which is usually not prostitution. Sure I got food, clothes, travel, rooms, uninterrupted naps, etc. but when i go out on dates, the fellow [only if he’s new] pays for dinner and a movie/play/cover and usually drives. And buys me liquor. And I either fuck him or i don’t.

Prostitutes have sex for money.

What’s the difference?

Braless Parties Have Rules Like the Fight Club

ok, so i haven’t seen the fight club, but i know there are rules. like the first rule is to not talk about fight club? right?

the first rule of braless parties is that girls who do not arrive without a bra are required to take them off. they may take it home when they leave.

that’s it. otherwise, it’s just a party, except with nipples everywhere. and a heightened state of eroticism.

i like games with a small number of rules. like, orgasm=suck me. simple.

we’ve had about 5 nights in the last few weeks that have been declared braless. we’ve tried for 4 more, but various girls vetoed the idea.

i can respect that. we tried once they were already over. not everyone was interested. now we give fair warning. but not every party is braless. that’s just CRAZYass!!!

so our tina’s young fresh nubile virginal adventurous timid honest shy outgoing cool nerdy sister has moved to town. going to sfu studying arts. pick a major lllllllllllllllater girl. good girl.

and she’s living in res and enjoying meeting people.

and she’s come over a few times. only 1 was a time when we were having a braless party.

that’s her bra above. C-cup. but she’s already gained 3 pounds since she moved to town in august so we’re bugging her about the other 10 pounds she’ll gain this year and how she’ll need all new bras. she’ll have none of that. good girl again.

at any rate, she’s a good girl. christian too, so i approve. 🙂

she’s had some boyfriends, she’s been to third base, she’s dated guys who weren’t virgins, but she still is. and her goal is to change all that. not in the same crazy sex-fiend way that i did 6 years ago when i came to vancouver. at least i hope.

no i take that back. i hope she does what she does. even bad shit is a learning experience.

me and tina and her have created an adultfriendfinder.com account for her. we won’t tell her i.d. though. but if you ask me [smwr1982] i might tell it if i screen you and you pass. lol

she realllllly wants to go in there and hang out in the chat rooms and hear how all that’s done. i told her it’s less representative of the real world than the real world. our parties are also less representative, but at least at our place there won’t be 900 boys trying to get her to watch them cum.

not that there’s anything wrong with that. 🙂

so of all the hijinks going on at our braless parties, tina’s sister has been a good little girl. granted the majority of girls at these parties don’t spring into orgies. in fact, most nights nothing happens.

but one things for sure. her statuesque build and big boobies are a hit.

and while she has not been ignored by the boys, she’s staking out her turf.

this is just one benefit of braless parties.

i highly recommend them. especially if you like the boobies!:)

in touch,

holly and tina

Victoria Hippie Chicks

ok, this girl could live in Victoria right now:

click on it and you’ll see it’s from Boston in 1971, but there’s a kind of fashion vibe in Victoria, BC that i like to call hippie chick or earthy chick.

long hair. baggy jeans. loose t. flannel shirt, not buttoned. long hair, without product. maybe a bra. it’s a nice look.

what am i on about? well i’m in victoria now. mostly to not be in Vancouver. it’s just killing me. the Olympics are starting later today and for weeks the black helicopters have been buzzing around and grinning zombies with blue jackets are making everyone feel guilty for not loving how 6-10 billion dollars on this stupid party for the rich [gold medal men’s hockey tickets are going for $8-12,000 right now on ebay] have led to huge health, education and social service cuts.

pardon me for thinking it’s a waste of cash for a 2 week party that no one i know can afford to attend.

and since i’m sick, wicked cold, sinus bullshit too, i can either lie in bed at home or lie in bed at a Faisel’s apartment in Victoria. so i packed up my Diane and we hit the bus/ferry/bus to UVic. Faisel is Diane’s friend. they met at a poetry reading. how hippie eh!

he lives in an attic bachelor suite near campus. he has a porch that fits 3 people standing. exactly. it has a view of 3 arbutus trees.

great for smoking a spliff in honour of the Olympic torches which are shaped like joints. i love that.

dude has let us sleep in his bed. if it weren’t a double i’d invite him to join us. platonically of course. 🙂

he said he’s never had 2 girls sleep in his bed before. it titillates him to think about what we might do in his bed. whether he’s awake or asleep.

so we came over today. a box of tissues at the top of my backpack. we had dinner at the Reef. yum, of course. and drank pots and pots of tea tonight.

tomorrow and the weekend are who knows what. and if i’m better, it’s back home on sunday night.

but not before we do the Victoria hippie chick thing. since Diane and i dress like them as well we kinda fit in. at the Reef we saw 3 of them, individually, not in a pack. they often travel alone…easier to slide up beside them.

so our goal is to find 4 hippie chicks this weekend. tough call because i’m sick and i don’t know if i’m up for that much socializing/sex, but i’ll work on it.

and if you’re a hippie chick in Victoria, or know one, send me a note because i’m in your hood! hopefully in more ways than one!

in touch,

holly

Sex Tip #17: Listen to Your Elders

I was sitting at a bus loop today and a girl comes and sits next to me. She’s oblivious as many teens are, on her cel phone. But then again many of my friends walk around like cel zombies too so I don’t need to be all agist and everything.

She’s cute with long dark hair. She looks Malaysian or Filipino or something like that. Real gorgeous anyway, for a 15 year old.

And she’s wearing white shorts, flip flops and a loose fitting burgundy t-shirt with a scoop neck. Very attractive.

So as she sits down she leans forward, arranges some stuff in her bag, pulls out an apple. All the regular normal kinda stuff. And as she’s sitting its leaning here and there, sometimes sitting on one foot, sometimes leaning forward with her elbows on her knees.

And all of my focus on her posture is all about more than just her being a cel zombie. She’s also somewhat unaware of her body. Unaware that in various postures, someone standing in front of us actually at the curbside in line for the bus can look up her shorts a bit. Burgundy panty. Quite elegant. And since we were on the west side it fit that she could look so nice like that.

But more than the loose legs on her shorts was her scoop top with a thin and loose fitting bra. And even if it were a tight fitting bra, it covered a small enough amount of her breasts that there was much to look at. Especially when her shirt fell forward from her posture.

So her cel call ended and I struck up a conversation. I introduced myself and said how much I liked her bag. She complimented me on my bag, which feels like an army utility duffel, but is actually quite functional. And then I said I wondered if I could tell her something somewhat personal about her. And being an open friendly girl [and courageous enough] she said sure. And I said that I spent a lot of time flirting with guys in bars and dressing for clubs and things [which I don’t go to clubs, but I knew she’d get that] and I intentionally dress to show off my body for those kind of places.

And I told her what I could see of her body for the last 10 minutes. And that being that provocative as a concept is fine, but there are times to use it and there are times to avoid it and everyone needs to make up there mind on that.

And though we were on the west side, we weren’t surrounded by corporate lawyers and personal trainers at this bus stop and that the general public is a mix of people, not a controlled group of people at a bar seeing a folk music duo for instance.

And then I asked about her English teacher and whether they had talked about how to write for different audiences. She said ya.

So I said the same goes for dressing and how we present the erotic parts of our body. And I tried hard to say not to dress and sit like all that at bus stops, but that she should think at least a little bit about context and the effect of what she does. And how to find places to dress and be a certain way and to be wary of accidentally doing so in other times.

Cuz, I said, when we get on the bus, it’ll be crowded and a few people will have a nice view down your top if you sit a certain way. If you don’t they’ll just see a pretty girl. And that you can’t control which guys are standing beside/over you.

And then I apologized if I ended up making her more wary than I intend [which is not so wary at all, just clever about things], but the world is full of risks that we can sometimes minimize.

And I felt like a big sister, young aunt, even the hip grandmother that tells the secret secrets of life.

And I feel comfortable in my role as an elder. And she listened to me and thanked me. And I wrote down my blog address. 🙂

And the sex tip is to listen to your elders. Not all of them cuz some are fucking nuts. But discern who is worth hearing. And listen HARD. Cuz it can make a real difference in your love/sex life and even all aspects of your life.

So there. Felt good!