more on motel fucking

so i realize that this was a risky hook up.  just want to say that from the get.  my best friend was not happy i did this.  however i've been a little bored lately and that boredom has caused my judgement to decrease....

due to work it had been six days since i had been fucked.  there was one fuck session in those six days but i don't count it because it was just ok - one of my regulars who has gotten less hot and fun lately, definitely gonna downgrade him on my list.

i had made plans the night before with "racist guy".  yeah i know why am i fucking someone who i refer to as "racist guy" however he is a really hot fuck.  so racist guy cancelled on me and we rescheduled for tonite.  got a text from him midway through the day saying he needed to cancel again.  annoying.  i have one or two regulars that are flaky and i put up with it because a) they are hot, b)  they are hot fucks, c) i like them as people despite their flakiness.  racist guy is just a hot fuck and convenient and usually available so i'm not willing to put up with flakiness.  sorry, i digress, not the point of this post

so clearly i am horny as hell.  

i had posted an ad on craigslist a few weeks ago.   not something i usually do as craigslist can be a bit of work and i'm lazy.  however i was bored.  i got two interesting hits - neither of which could host.  i prefer to travel.  but this one dude and i had been texting pretty regularly for a few weeks trying to arrange something.  hot texts.  he's a dom top which for those who follow this blog know is one of my weaknesses.

so i text him to see if he's free.  he is but not till kind of late and its the middle of the week.  however as i said i'm horny as hell and i'm not feeling like any of my regulars. 

the other thing is if we are gonna fuck we are gonna have to get a motel room.  i've done a motel room fuck before and its not so much my thing.... however this dude has got me curious and as i said before i'm horny as hell. 

so i say ok.  lets do it.

i'm nervous about this hook up.  usually i don't get nervous anymore however the combination of late night, motel, part of town i'm unfamiliar with, and the fact that he's gonna pick me up in his car at the bus stop and drive us to the motel all are making me a little nervous - ok more than a little nervous. 

but i want it.  so i make sure i have enough cash for a cab if needed, text my safety bud the hook up info, and head out. 

he picks me up at the bus stop.  he's attractive, has that roughneck look and vibe.  we're chatting on the ride over to the motel.  the vibes cool.  he's never fucked a trans guy before but has fucked trans women.  he asks if i've hooked up in a motel before, i say yeah and i wasn't so into it.  he said well maybe after tonite you'll change your mind. 

we get to the motel.  its clearly a hook up motel.  he tells me to get a room and he'll give me cash for half and to text him the room number and he'll meet me in the room.  this dude is very dl

the last time i did a motel hook up the dude paid, but the motel owner made me show ID cuz he thought i looked too young....  so i'm nervous getting the room.  however i get a room for a few hours, no ID needed at this place.

i text him the room number.  he comes into the room and turns on the tube.  there is porn on the tube.  lol.  this place is clear about what's its used for.

we strip.  he's hard, smaller than i expected but that doesn't matter to me tonite.  he tells me to suck his cock.  i take him into my mouth, blow him for a while, he face fucks me hard and rough, but i need to get fucked and i tell him so.  he grabs a condom and plows into me.  fucks me hard - which is how i like it.  the room has a whole wall of mirrors so i watch as he fucks me.  he pounds me pushing my legs over my head, holding me down, slaps me around a bit.  hot. then pulls out and cums on my face.

there is an element of danger to this that keeps me a little on guard and not totally relaxed, like i don't know this dude and something about being in a motel makes me feel more nervous.

we both rinse off.  then he says ok, lets go.  i say, really?  Your only going to fuck me once?  He says ok, suck my cock.  i blow him for a bit, he's hard again.  I say fuck me.  He says no, suck my cock, do as i say.  Hot.  I suck him off some more then say again "fuck me".  He says no.  I suck his cock some more.  Then i ask again, "please fuck me".  He responds by slipping on a condom picking me up and slamming his cock into me. 

I ride him for a while then he turns me around and pushes into my ass.  He holds me down and pushes my head into the bed as he rides my ass, i'm moaning and grunting, rubbing my clit as he pounds me.  He's pushing my face into the bed, he's much stronger than i am, its hot, however there's a moment when i think what if i want him to stop and he doesn't, i realize my vulnerability in these moments, however when i push back he lets me up, I turn around, pull off the condom and grab a new one.

i say i want you in my cunt.  he slides into me, fucks me hard and rough, pushes my legs up over my head, pounding into me, i'm watching him fuck me in the mirror.  so hot.  he pulls out and cums all over me.

he gets up and hops in the shower.  when he's done i do the same.  now i'm starting to feel nervous again, what if he just takes off and leaves me in this random ass place.  however he doesn't.  i drop the key off and he picks me up outside.  we chat as he drives me to the bus stop.  he asks if i fuck alot of girls.  i say have in the past but now mostly dudes.  i ask if he does.  he says yeah with a grin.  he runs a bar so he says he gets alot of offers.  i feel like we are having some convoluded, sexist, male bonding type of moment.

he drops me at the bus stop, i have to ask him to give me half the money for the motel room, but he does without trouble.  i hop on the bus and trek home.

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

Reflections on my year of fucking around

Sitting at my desk at work today (procrastinating), I started to reflect on what a surprise this year is turning out to be. My co-blogger and I comment on this from time to time. Early last year, I never would have foreseen this sexual bent to my life - the explorations of hook up sites and anonymous sex. Many people in my everyday life would probably be shocked to learn of what I do when I'm not hunched over a computer or facilitating a workshop. In fact, maintaining this double existence (and let's be real, it is a double existence) can be quite taxing. When people at work share their dating stories, I'm usually mum. The most I can offer is, "yes I did have a date last night and it was...nice." Instead of moving on to the next topic, they become even more intrigued and unsuccessfully try to get more information out of me. Over time I've discovered that my vague responses have the opposite effect: they just bring on more questions.

Not that I feel ashamed of what I do on my free time. There just never seems to be the right time to say to your co-workers, "oh last night? I met some dude off the internet. We fucked in his apartment and then I had to scurry out of there before his roommates got home." Maybe this just means I'm not super close to my coworkers. After all, a few of my good friends know. 1 or 2 actually read our blog. But I don't talk about my sex life at work and maintaining this double life is certainly the least enjoyable part of this journey, especially when I want to do the complete opposite. I actually do want to talk about my sex life every chance I get. I do want to find out how other people feel about sex, what they enjoy the most, what they're not into, and what they secretly want to try but feel too shy or ashamed to mention (feel free to share your responses to these questions in the comments section!) I want to be able to share how allowing myself to enjoy sex, without being limited by guilt or shame, has unveiled this whole new me that can appreciate the beautiful imperfection known as my body.

For years I internalized messages that told me I was ugly because I am black, have a wide nose, big lips, etc. Now I can look in the mirror and know that my nose looks like my mother's nose and hers, in turn, looks like her mother's, and so on. I can cherish my lips because my father had these same lips. In fact, my face is a manifestation of the interplay between numerous genetic and cultural legacies. I did these histories a huge disservice by buying into those messages that equate blackness or trans-ness or queer-ness with "undesirable". My salvation hasn't been sex per se. I'm not saying that you should go fuck around so that you can feel good about yourself. I'm merely pointing out that, taking control of my sexuality and my body, not allowing them to be defined for me, was my saving grace.

I also don't want to give the wrong impression that I walk around always feeling good and happy about life. There are certainly days when I feel heavy. I wish I didn't have to live paycheck to paycheck. I would love to just meet someone and not have to do a trans 101 discussion. I would love to not have to encounter the particular type of racism black men face. On the train the other day this white woman took one look at me and, rather than take the empty seat beside me, chose to squeeze into another already teeming with bodies. I want to be able to tell her I'm not the monster society has concocted and stamped into her subconscious. And I would most definitely love the stares to stop. God, how I want those damn stares to go away. Sometimes that shit can just weigh you down. There are still a lot of these moments…

But all in all, fucking around for the past year has been an incredibly rich and multifaceted ride and through it all I can be thankful that I feel alive, in more than one sense of the word.