daddy bear

while i have alot of luv for bears and would do one now and again (my sunday afternoon bear) i would always say that bears were not my ideal cup of tea.  however who i find hot shifts and changes over time.  lately i have had a huge thing for bears, daddy bears to be specific.  i always have luv for a hot daddy, and every now and again get a craving for a sexy bear, but a daddy bear, that's new for me. 
however, i had not been able to arrange a hook up with one.  this guy and i had been chatting on and off.  total daddy bear (that is how he self identifies) but he is not so attractive to me.  so i know this is not right, but he does however have a beautiful cock, thick with a huge head, its just so hot.  i asked my best friend is it wrong to hook up with this dude just because of his cock, he said, of course not, go for it.

its funny i was talking to a hook up recently, hot sexy dark skinned dude (gonna write a piece about him soon), swapping stories, which i luv to do, and i told him there is this one dude i hookup with who is not attractive to me however he has an amazing cock, i say thats wrong huh, the hookups says, 'nah man, u find a cock u like stick to it'.  

so we arrange to meet up.  i get to his place and on first glance he's not attractive to me.  white guy, all bear, medium height, dark hair, ok looking, i prefer my bears big and tall when i do a bear.  but i'm there so as usual i'm like what the hell.  we chat a little.  he's a wealthy bear, fancy apartment.

we go to his bedroom and start kissing and making out.  i'm his first trans guy, he is gay, just fucks non trans dudes, so i think we are both a little unsure, however he says 'wow, ur hot, way hotter than ur pics' as he kisses me and plays with my nipples.  i'm getting very turned on.  there is something about this dude that is really getting me going.

i pull off my shirt and he wraps his lips around one of my nipples.  i reach down and stroke his cock though his boxers.  he is very hard.  i pull of his boxers and take his cock into my mouth.  he really does have an amazing cock.  incredibly thick with a humongous head.  its beautiful.  i really have never seen a head that big - i luv it.  i luv just sucking the head, my lips sliding over its beautiful smoothness, really, i could do that all night.  i blow him for a bit but i really want him inside me. 

condom i say, he really is quite sizable so i'm wondering what kind of condoms he uses (magnum xl), he grabs one and slides it on.  i lube him up substantially as he is very thick and i tell him to go slow as he pushes his cock inside me. its fucking amazing.  i have never fucked a guy with such a thick head and it feels incredible - like he's hitting all the right places.  he fucks me for a while.  he likes to be on top (which i prefer).  he spreads my legs, pushes his thick head in and out of my cunt, stroking me, long full strokes, so i feel all of him, every inch, it feels so fucking amazing.  i'm getting turned on as i'm writing this.

and every now and then as we are fucking he says "are you daddy's boy?" and between my moans and writhing i manage a nod or a yes.  

then he says he needs to take a break.  pulls out and lies on his side.  reaches down and plays with my clit while he wraps his lips around a nipple.  he really knows what he's doing.  i can't believe he just fucks non trans guys.  he's stroking my clit just perfectly.  so hot.  i cum a couple times.  i'm so turned on.  i grab  a condom and slide on top of him.  i ride him, feeling his cock stretching me, he turns me onto my back and plunges his cock into me, fucks me hard and fast, pushes my legs over my head, says he's getting close, pulls out and pushes my head towards his cock.

i pull off the condom and wrap my lips around him, teasing his balls with my fingers, he groans, as i slide him down my throat, stroking his cock with my lips, he says "good boy, ur daddy's boy", i feel him start to cum and pull back as i don't want him to cum down my throat and i take him in my mouth, milking his cock (i don't usually let hookups cum in my mouth - just got a bit carried away...). 

then we cuddle and rest for a while.  i run my fingers up and down his chest, he's very hairy, not usually my thing, however this guy really gets me going.  we start kissing again and i can feel that he's hard.  i take him into my mouth and stroke his beautiful cock.  fuck me - i say.  he say's 'i don't know if i can do it again but we can try, you've got me going again'.  he slips on a condom and pushes inside me.  fucks me missionary style, i raise my hips to meet each stroke, he moans, we fuck frantically, hard and fast and i can feel myself cumming, i groan and grab onto him as i cum.  he pulls out and i lie back exhausted.

he doesn't cum but i'm too tired to care and i figure if he wanted to he would (i sometimes feel self conscious about if a dude cums or not, like if he doesn't that its because of me or something which is clearly bullshit and my own shit, so i try not to feel that way and remind myself that if a dude wants to cum he pretty much across the board most definitely will...). 

typical daddy he asks if i'm hungry, says i can stay the night if i want.  i almost never stay the night at a hook ups place, just a thing i have.  however i am tempted, but i can't i don't have a change of clothes or anything and i need to work the next day.  so we cuddle for a bit more and i don't want to leave but i know i should so i clean up, grab my shit and kiss him as i walk out the door.

new luv for the moment - daddy bears

my sunday afternoon bear

i had hooked up with one of my regulars friday night. he's what i think of as a marathoner, meaning, i know if we're gonna hook up i won't get home until 3am at the earliest and that i may need the next day to recuperate (which i did). however, i had been feeling the need for something new, yet had not been having much success.

its now sunday afternoon and i'm just lazing around, i have my sites up but am not paying a whole lot of attention when i notice a new message. the subject says "FTMs drive me wild"

ok, that catches my eye. I check him out. he's a big, 6ft something, 280lb, bear. Much luv to all the bears out there, however bears are not usually my thing.

But every once in a while I get a craving.

He's cute and is a 5 minute bike ride away (again my thing for anything local).

We chat some, turns out he's never been with an ftm before, but has been wanting to for sometime and finds the idea incredibly hot. I tell him what i'm into and ask what he'd like to do - he says theoretically he would like to finger fuck and pussy fuck me, theoretically cuz he's never done either before, but no kissing cuz he has a boyfriend (open relationship).

Sounds good to me. i kinda luv that he said "theoretically".

Then he says you know i'm a big guy right. I say I like big guys.

He only has an hour or so before his boyfriend gets home. So i head over. I get to his place, big place, you can tell a couple lives there. We sit down on his couch. He says he would never know that I'm trans - that i even walk like a guy - I just had to put that in cuz i thought it was interesting - what does a guy walk like? Anyways, we're chatting and i'm very aware of time.

He says he's really nervous. Sometimes nervousness is a turn off and sometimes I love it. In this case I love it. Dude is almost 3x my weight and way over a foot taller and i'm making him nervous - its very cute.

Its clear i'm gonna have to take the lead which is also not so much my thing, i'm on the sub side, but sometimes taking the lead is hot and in this case it is so I say babe don't be nervous and i stroke his face. then i climb on top of his lap and kiss his neck while i grind against him. I pull of his shirt and help him with his pants. I strip. he's sitting on the couch, he's such a big mountain of a guy i kneel down in front of him and take his cock into my mouth. he's semi erect so i help him out. he moans as i guide my lips up and down his shaft.

i climb back up on top of him so i'm sitting on his lap. i take his hand and i guide his fingers into me. he starts stroking my cunt with his long thick fingers. i ask him if he likes it, he moans and nods. I ask if he wants to fuck me. he nods. i grab a condom and slip it over his dick. then i guide him into me. he squeezes my nipples as i ride him. he cums quickly - but its very hot. he apologizes for cumming so quickly, says he was just so nervous. I say no prob man, don't worry about it. he says with a grin if we meet again i promise i will last longer. i smile - nice.

I clean up, get dressed and head out. He says, 'thanks man' as i'm heading out the door. I get home and text him - Thanks - you made my sunday much more interesting.

roof top screw

So I have a thing for roof tops. Hooked up with my regular who I’m always
questioning if I should hook up with again. I’ve written about him before. Latino bear daddy type. Its just I have a thing for daddy types sometimes… so we arranged to meet at his place, he said he had a family thing to go to beforehand but I was like no worries I can hang at the bar if you’re running late. Got to the bar and he texted that he was gonna be late and that I could meet him at his family thing if I wanted (oh yeah forgot to mention the reason I’m always questioning this guy is he is a bit much, he wants way more than a hook up… borders on obsessive... however he is a really good fuck). I said no I would hang at the bar. Waited for a very long time…. Annoyed and about to leave but then he showed up.

His family was home when we got to his apartment, which is awkward, so we went up to his roof top. This made the wait worth it. It’s a nice summer night. We drink some wine. He kisses me and plays with my nipples through my shirt, very hot. I unbutton his pants and kneel down in front of him. I take his cock into my mouth, he is already hard, I suck him off while he plays with my nipples through my shirt. He unbuttons my pants and fingers my clit. He puts his shirt on the ground and lays me down on top of it and pulls off my pants, i slip a condom over his dick, he drops his pants to his ankles and he pushes into me. The ground is way too uncomfortable so I stop him and get up. At this point he kicks off his pants and picks me up in his arms, i wrap my arms around his neck, my legs around his waist and he slides into me, fucks me standing – love it. Love that he is so big and strong and can fuck me like that. We fuck like that for a while. Then he carries me over to a bench that they have on the roof and I ride him for a while, i look up at the stars as we fuck. Shit so hot. I ride him til we both cum. I put my pants back on and we drink some more wine. We head back downstairs to his apartment.

We get to his room and he lays me on the bed and we start kissing and grinding. We strip again and he sucks me off and then starts tongueing my ass. He’s hard again and he turns me over and asks if he can fuck me there. This is not something I normally do but I’m in the mood (I’m also a little sore in front from previous hookups…). I say yeah but to go slow, he slips on a condom and rubs the tip of his cock against my asshole, until i'm wanting it, grinding back on him, then he slowly pushes in, fucking me slow at first then fast and hard until I can’t take it any more. I tell him to switch condoms and he fucks my pussy for what seems like forever until we both cum. I lie on top of him exhausted.

At some point I must have fallen asleep, I wake up and the sun is starting to come up, I don’t like to spend the night at my hookups, just a thing I have, however I’m still here… he's spooning me and i feel his cock against my ass, he’s hard, we grind for a while then I tell him to get a condom and he pushes inside me, fucks me slow and hard, I rub my clit as we fuck, he keeps fucking me then pulls out, takes of the condom and shoots all over my back.

I clean up and tell him i have to go, he offers to make breakfast, to call me a cab, all which i decline. i kiss him goodbye as i leave. The sun has just come up as i'm walking home, love early mornings especially after i've been fucked...

motels...

I had been messaging with this guy for a bit and we decided to make it happen. He'd been with a trans guy before. We met at a bar near his place. My type, more attractive than I had expected based on the pics. Cute, brown skin, latino, medium build, beard. We chat some, or more so he talks non stop and he buys me a drink. He says so you wanna do this. I’m game.

So we leave the bar and he calls a cab, he says his place is a mess and he doesn’t want to go there tonite that he has another place to go. Cabbing it somewhere with a hookup is not something I normally do, but the vibe felt safe though I was definitely nervous. We chatted during the cab ride, ok guy. We pull up at a cheap motel in some random part of town. He pays for the cab. I’m still feeling a little nervous but decide to go with it. He pays for a room. Of course, the guy at the counter asks me to show ID (i look pretty young...).

We go up to the room, its your typical cheap pay by the hour motel room, everything is that slightly dirty color of beige, along with a flashing neon sign outside the window.

he kisses me, I unbutton his pants and begin sucking him off, he smokes while i suck his dick which i actually find really hot, we strip, this is when I realize he is less my type without clothes on, a total bear (no offense to bears just not my thing usually), but at this point, whatever, he sucks me off, grabs a condom and fucks me for a long time in a couple different positions, he’s a pretty good fuck, big guy which I like…

Afterwards we lie in bed and chat some about our lives, backgrounds, etc. He starts kissing me again, I feel him getting hard, I suck him off some more, he grabs another condom and we fuck again. Afterwards I tell him i need to get going so we head out.

He’s a total daddy type, insists on paying for my cab ride home, wants to see me again…… I have a taste for daddy types every once in a while.