the skilled cock

dude used to be one of my regulars however we had not hooked up in over six months for multiple reasons mostly due to scheduling.  we had been hooking up pretty regularly at one point, light skin gay guy of color, slim, average build.  he'd been with trans guys before.  total dom top.  

he's the kind of hook up that i appreciate.  we would chit chat some but not alot, he prefers to get right to the fucking and then the post fuck chat is minimal.  it was not an in and out type of situation, we would fuck then cuddle some, maybe watch something on tv, he'd invited me to stay for dinner before (which i declined but thought was nice).  a good number of my regulars like to chat and i'm into that sometimes, but other times i just want to fuck and that's it.  so this dude i have an appreciation for. 

we finally arranged to meet up.  he looks a little more worn down than the last time i saw him.  hard times all around these days....  we don't chat much and get right to fucking.  we both strip immediately and we kiss and grind our bodies together.  his lips are really chapped which i'm not so into.  but he is hard immediately.  and he has a beautiful cock, it has a slight curve in it.  i quickly  wrap my lips around it and slide my mouth up and down its smoothness.  he moans. 

i grab a condom, slip it on and lube him up.  i put the tip of his cock to my cunt and slowly slide him in.  i moan as he enters me.  i ride him slowly at first getting used to the feel of his cock.  he feels so good, his cock deep inside me, i luv the way it feels as i slide up and down its smoothness.  i ride him with a silly grin on my face thinking why did we wait so long to do this again.   however now i want him on top.  i pull him over so he's fucking me missionary (missionary is my favorite position). 

he strokes me slowly our bodies tight against each other.  i grab his ass pushing him deep inside me.  i raise my hips to meet his strokes and clench my cunt around his dick in a way that also hits my clit hard.  its majorly hot.  then he starts fucking me hard and fast, pounding into me, rough fast strokes til he cums shooting inside me. 

he lies on top of me his cock still pretty hard inside me.  he keeps stroking me.  its very hot.  then he stops and starts doing this incredible thing with his cock that i've never experienced before.  i can feel his cock pulsate inside me.  its like his cock is expanding and contracting inside me over and over again it feels like he is cumming non stop.  i cum multiple times from this.  he keeps this up for a good while it feels like we are both cumming over and over again.  until he collapses on top of me his cock now soft and i slide him out.  

as we lie there catching our breath i say to him, that was incredible.  did you cum multiple times or what was happening.  he said he only came once but its something he learned to do with his cock even after cumming.  hot. 

we lie around a bit just resting, however i need to go so we clean up and part ways with a quick kiss. 

disappointing fuck

dude hits me up on one of the sites.  his profile says he is 45 years old.  however in his pics he looks barely into his 20's.  Japanese guy.  i message him back and say there is no way you are 45 years old.  though i'm also thinking there is no way those pics are current.  however, i know alot of people of color look way younger than their age...  case in point myself transness aside.  we bond over getting carded regularly at bars and even at times for cigarettes.  i'm still a little suspicious about the pics but we keep chatting.  he's interesting.  i've found that older guys often have lots of interesting stories and he seems interesting.  he has strong racial politics which is also a major plus.

he has never done a trans guy, in fact he has only been with non trans guys his entire life.  he states he is not sure about how he will react but thinks i'm majorly hot.  we get into a pattern of sending at least daily messages to each other discussing a wide range of topics from what we want to do sexually to gentrification.

after about a week or so of this he mentions getting together to explore my body i.e. fuck.  we decide to arrange a date however i'm feeling conflicted.  on one hand he seems like a real interesting guy and his pics are cute and he said he prefers a slow sensual fuck and right now i mostly have rough dom types.  on the other i have a feeling his pics are inaccurate and he is not gonna by attractive to me.  i also have this feeling that maybe his pics are very, very old and he will not look anything like his pics.  don't get me wrong i get majorly into a hot daddy but i'm unsure if this dude is that.  however, i decide to just go for it mostly cuz i find him interesting, i tell him to meet me at a coffee shop near my place so i can feel it out.

we meet up one week night evening.  he shows up and he doesn't look like his pics.  however he's cute in a round, brown boi kind of way that i find very attractive.  we chat some and then i ask if he wants to go back to my place.  he says sure.  we get back to my apartment and resume chatting on my couch.  now i'm realizing maybe he's not so attractive to me.  the coffee shop lighting was a bit dim....  he also is not really as interesting in person.  we chat for a while, random usual prefuck chat, nothing inspiring.  I'm feeling disappointed as he was so interesting via email....

he seems like he could keep on chatting all night so i realize i'm gonna have to make the first move.  i ask if he wants to go to the bedroom.  he says ok and we head to my room.  this is when things start going even more down hill.  we strip and i realize he really is even less attractive to me without his clothes on.  however, i hold out for that sensual fuck he described. 

we fuck.  its not short, but not long and just not that great.  the whole slow sensual fuck he described to me is no where near what happens.  basically i ride him til i cum then he cums soon after.  nothing sensual about that.  after we are done i decide i want him to leave though its clear he wouldn't mind staying and chatting.  i toss him a towel and ask if he wants to clean off.   he cleans up, i thank him for coming over and show him out. 

you can't make this stuff up...

sometimes what happens on a hook up is almost too much to be believed.  this guy and i had been messaging on and off for a while.  tall, white, dark featured guy.  older.  a runner. 

we finally arrange to meet up and i kid you not, this is what happened.  dude show's up. he's a little less toned than in his pics, but whatever doesn't matter all that much to me.  he's a talker.  kind of talk's non stop.  he's a magician by trade.  interesting.  he has been doing it for a really long time.  he says he wants to show me a clip from one of his shows.  we watch it for a bit.  he is pretty good.  this is all fine. 

we are sitting side by side on my bed continuing to chat.  then he tells me how he's learning hypnotism.  interesting.  he says the first thing you learn is self hypnotism.  i say are you serious - what's that.  he says let me show you.  then dude, i almost can't write this, seriously fucking closes his eyes, sits with his palms up on each knee like he's meditating and says "i am powerful" or some shit like that and then just sits there with his eyes closed.  after about a minute or so during which i am really questioning how i allowed this person into my bedroom, he says the same phrase he started with "i am powerful" or whatever and all of a sudden open's his eyes.  They he says "see, that's how it works".

at this point i'm really unsure about all this, i mean perhaps self hypnotism really does exist, but why would you choose to do it on a hook up, then he leans in and plays with my nipples.  this is an immediate turn on for me and the ridiculousness of the last few minutes somehow leaves my mind.  we fuck, its good, not amazing or worth going into too much detail about, but soon after we are done i show him to the door.

lessons learned - anal cleansing

i've been doing alot more anal these days.  just a mood i've been in.  i choose the dudes i do anal with carefully though.  i prefer a cock that is medium to long in length but not thick.  i mean i've been ass fucked by quite sizable and thick members before and had a lot of fun with it, but i can often only go so long.  

the rest of this post may be tmi for some so please skip it if needed.

the other thing about anal for me is that i have an issue with feces.  its just not my thing.  no judgement for those into it, its just not what turns me on.  even though all the guys who fuck my ass don't care how 'clean' i am and if there's some mess which there is apt to be with anal fucking it doesn't bother them.  however it bothers me, which means i can't relax and just have fun with it.  clearly my issue.  i know that some mess is par for the course with anal fucking and there is nothing wrong with it.  again all my issue.

but i like to get fucked in the ass now and again and i like it to be fun for me.  this had led me to get into anal cleansing/douching.  i understand that it increases risk of hiv/stds to douche before sex but except for with one special person (with whom I have an agreement and arrangement) I use condoms and lots of lube. 

this all led me to purchase my first anal douche.  i went for the low budget model as that is my current situation plus who knew if i would be into it or not.  the thing is it comes with very little instructions so i did some reading on the internet and generally got a sense of what needs to happen.  i just use warm water.  i know there are solutions and mixtures but those seem to come with more possible negative consequences.

the very first time i tried it i didn't use lube.  maybe its just the way my ass works but i could not get the nozzle in and quickly realized i needed to lube it up just a little and then it slid in just fine.

however then another challenge arose.

the first few times it was really hard for me to squeeze that water into my ass.  like i would have to really strain and squeeze the bulb of water really hard.  even then it could only get about half of it in.  however it generally seemed to do the trick.  though i noticed sometimes i would be totally clean and other times not.  after maybe the 3rd or 4th time i realized what i was doing wrong.  basically i think i was inserting the nozzle (for lack of a better word) so far that it was blocked by whatever part of my inner lining it stopped at.  if i pushed it in then pulled it out just a little i was able to get all of the water in with no problem with much better results.

great.  seemed like i was getting the hang of it.  however, in my effort to be clean one time i over did it.  lets just say i did one more bulb of water than i should have and didn't properly evacuate.  luckily when i felt a weird gurgling in my lower region i was alone at that point and able to make it to the bathroom just in time.   

after all this i think i've pretty much got it down now i.e. how to get the water in my ass and how to make sure it all comes out.  feel free to share tips if you'all have them : )

itchy

it had been a lazy day.  i had hung with a friend earlier and i was just at home drinking some wine, cooking some food, i was looking for a hook up but in a kind of lazy way.  not having any luck on any of the sites - slow day when i got a call on my cell.  i didn't know the number so i didn't pick up - as is my practice.  i listened to the message and it was some dude who said we'd been emailing, that we had met through CL and wanted to know if i was free to fuck.

i have no idea who the hell this guy is.  i had not posted on CL in a number of months.  so i went back through my email to try and figure it out cuz clearly we had been chatting since he had my number.  after some investigation i figured it out.  its this dude that had responded to an add almost six months ago.  we had emailed on and off but neither of us could host and i'm not into motels.  also he was ok looking in his pic like it could go either way. so i'm feeling indecisive, i'm not incredibly horny, can't decide what to do. 

i text him back and he calls.  i hate talking to hook ups on the phone, i would rather text, but whatever.  turns out he lives three blocks away.  for folks who follow this blog you know i have two major weaknesses:  1) anything local, 2)  dom tops.  so 3 blocks is fucking hot.  i think what the hell, lets do it.

he says he can host, but he'll have to sneak me in.  i'm not sure what that means, but whatever i'm game.  i say i'll be there in a few minutes.  i walk over to his place.  he comes to the door and does not at all look like his pics, not attractive to me, however i'm here and now horny and i've learned that physical hotness and sexual hotness do not always equate meaning i've fucked hot dudes who suck in bed and i've fucked unattractive dudes who are majorly hot in the sack and really i'm just here to fuck.

it turns out that sneaking me in just means tip toeing past his roomie.  he lives in his studio, he's an artist.  cool art.  no bed but i don't care there are lost of places to fuck.  we kiss, he showered right before i came which i appreciate however it means his long hair is damp which sometimes is hot but in his case is not.  he lays me down on some blankets on the floor.  he sucks my nipples, blows me, all good.  however i want to be fucked.  i suck his cock but he can't get hard.  he jerks himself off, i suck him some more but no go.  he apologizes says he did some coke earlier and has coke dick.  great.....

it turns into an oral session, he sucks me off, finger fucks me, i cum, but its not really doing it for me.  afterwards i get up to leave and he says 'no stay a little longer'.  i lie back down but realize something about this is making me feel itchie.  so i get up, grab my shit and bounce.

i was feeling bad about this hook up.  not so attractive dude, high on coke, limp dick.  my thoughts ran on these lines - what the hell is wrong with me.  if there is ever a time to walk away that was it.  why don't i have enough self respect.  why am i such a chicken shit. 

I have never shown up at a hook up and walked away.  While i feel confident that if a situation ever felt unsafe I would walk away I have been fortunate so far.  my best friend has no problem walking away from a hook up.  he does it with ease.  though the times he has had to walk away are mostly when its been a sketchy situation.  however, its hard for me to do and i know that i have a problem rejecting people - clearly my issue - that maternal, self sacrificing, put others over myself instinct that i can't seem to get rid of.

i was feeling really down on myself, went to bed feeling like shit.  however i woke up the next morning and decided to give myself a break.  while i acknowledge my areas of needed growth and the hookup did make me feel itchy....  at least i did take enough control over the situation to get what i wanted out of it - which was simply to get off...  the rest i'll keep working on

On Fucking Femmes

This is the 3^rd girl I’ve fucked in the last few weeks of my recent sexual transformation. 5 years ago I would never have even seen this coming, this strong sexual attraction for femme women. But this is where I find myself these days and I’m having to learn how, in my present fully passing black masculine self, how to approach and talk to women about casual sex, how to fuck women and be pervy and kinky, how to top and dominate a woman in a way that makes her feel sexy, horny and trusting enough to give over control. This particular woman actually approached me and, in my oftentimes-clueless state, I didn’t know or understand she wanted me to invite her over to my place and fuck the hell out of her. Not when she stepped to me and asked for a kiss at our 1^st hang out (see An Ode to Trans Guys.) Eventually she had to spell it out for me in our ensuing texts and, since then, I’ve jerked off many times thinking about her riding me wildly.

Well that 1^st hang out was several weeks ago. We’d been trying to hook up since then, but she lives out of town, is in seriously committed non-monogamous deal and quite busy. The odds of us actually meeting up started to look really slim. Eventually the odds were in our favor (shameless Hunger Games-phile here) and she happened to be in town one week when I actually had money in the bank. I invited her over for a home-cooked meal and thought that afterwards, if we were still feeling each other, we’d make-out and eventually fuck.

Later that night we chilled in my living room, drinking after dinner. A dinner I’d just whipped up that fell far short of what I’d hoped and dreamed it could be. She seemed to like it, or at least she said she did. The conversation was more relaxed now that wine had made an appearance. It made her smile and laugh more. It made her gestures more dramatic. As she talked I switched seats and sat right next to her. I put my hand on her thigh and felt the strongest urge to kiss her, but I was still new at this dating-and-fucking-femme-women thing, so I held back.  The sexual tension between us was thick in the air. We’d spent so long talking tonight, and still the tension was in the air. Eventually…

“I want to kiss you,” I stated once she paused for air.

“Okay.”

I kissed her while the smile was still on her lips. They were soft and wet and felt hot in my mouth. That I expected.

What I didn’t anticipate was the degree of sexual attraction that lay between us.

It took a few minutes to build.

Suddenly, as mouths parted and tongues collided, she climbed on my thighs and started grinding her hot crotch on mine. My dick was hard, so fucking hard. I grabbed her ass as she rubbed up against me.

 I slipped my warm hands underneath her blouse. One hand crept to her bra strap while the other cupped her big soft breasts. She moaned in my mouth, sucking on my tongue, twisting and grinding on my crotch as her hands wildly caress  my back. Eventually she wants more access and pulls my shirt up my back, reaching underneath the A-shirt, I wear to flatten my chest, to my bare-back.  By now I’ve unbuttoned that bra, my hand twisting and squeezing her bare nipples. She’s moaning, sighing, saying “shit”, “damn” and asking me to squeeze them harder.

“Wanna go into my room?” I ask as we’ve outgrown this couch. She nods and we kiss and grope and fondle our way into my bedroom. On the way I squeeze my hands down the back of jeans to her naked ass. I squeeze softly at first, then hard and bring her closer to me, kissing her mouth and playing with her tongue.

In my room she pulls away.

“Can we talk about safe sex?”

I’m in the process of taking my pants off. I nod and gesture for her to continue.

“Latex all the way. If you’re strapping on, if you’re fingering me, all of that is happening with latex. I brought condoms and,” she bends over and retrieves a box and some condoms from her bag, “gloves.”

After kissing and sucking and licking her tongue, after taking one erect nipple into my mouth, sucking softly then hard and repeating, after I put my thigh up against her pussy, grinding and feeling the hot wetness slide up and down my thigh, after she reminded me to put gloves on because my eager fingers started to part her wet and warm pussy lips, I slipped a couple gloved fingers into her pussy and played with her clit. Even through the glove I could feel the heat of her. She was so wet that sounds of my fingers playing with her pussy filled the room.

I have a huge, huge acoustic fetish. I love dirty talk, moans, grunts, curses, and most especially wet fucking sounds. I started finger fucking her, first it was shallow and slow, her hips moving in response. Then her hips moved faster and my fingers plunged in deeper, she arched. Her soft warm body undulated beneath me. I fucked and she moaned, bending her neck backwards, head pushing into my pillow. I finger fucked her harder, which deepened her sounds, mouth opening wider. I bent my head and pushed my tongue into her warm open mouth and twirled with hers. She greedily reciprocated, taking all of my tongue into her hungry mouth, sucking. I ground into her more vigorously, egged on by her sounds, the degree of wetness on my hands. Suddenly I pictured my dildo buried all the way in her warm tight snatch and it was an image I wanted to bring to reality. Quickly I got off her to retrieve my strap-on.

10 embarrassing and ultra dorky minutes later, we gave up on using the strap and just opted to use the dildo alone.

It turns out the harness was broken.

We still tried to use it. That’s how badly we wanted a strap-on to feature prominently in tonight’s activities. 

You would think all that fumbling around and tinkering with a broke harness would kill the mood, but as soon as she got on top of me, her full breasts dangling over my face, nipples poised on my lips, I got hard in seconds. Her nipples slipped into my mouth and I bit them, she ground her pussy on me, rubbing her clit on my thigh, until the intensity of that made me sit up and hold her naked body to my sweaty one, breasts in my mouth, sucking a little hard this time. It was time to use the dildo. I laid back down and positioned the 8-incher on my crotch. This was my fave one. It was thick as hell and I’d never used it on any one else before, but I was ready to try that.

She climbed on top of me and slowly slid down my dick.

Her mouth fell open.

“It’s huge.”

She moved slowly on my dick, coating it more and more each time. I loved watching my dick emerge from her pussy wet.

I loved the feel of her bare ass in my hands as she rode me.

She started moving faster, hungrier.

I grabbed her supple ass harder and moved my hips, thrusting up to meet her, feeling like this piece of silicone was actually my dick, disappearing in and out of her. We moved faster. I sat up again because I wanted to feel her body against mine, her breasts pressed against my chest. My dick slipped in deeper and I grabbed her ass hard and fucked her deep and rough for a long time. Eventually she grabbed my shoulders, squeezing, head tilting back and let out a loud loud moan. As she’s bent backwards like this, I can’t help but take a nipple into my mouth, which makes her gasp and gently push me away.

“Once I come they feel really sensitive,” she barely gets out in between pants, before practically collapsing on the bed beside me and nestling her bare ass against me.

I’m a panting and sweaty mess, so I get up to wipe off. Once I’m somewhat dry I get back into bed, my arms wrap tightly around her.

The last thing I remember thinking right before passing out is how much I love the smell of her pussy.

my first STD

we said we would write about the good and the bad.  we promised honesty and realness. here goes. 

i went to the doctor because i had a yeast infection.  i used the over the counter stuff which helped but it didn't feel like it was fully gone.  since i was at the doctor and it had been exactly three months since i was last tested i asked her to also test me for STDs.  she confirmed i had a yeast infection and gave me meds.  what's funny is this time i wasn't actually worried at all that i had an STD.  I was actually very confident that i was fine.  this i believe shows how i had been getting lax.

a few days later i get a call from my health clinic.  they let me know that i had tested positive for an STD.  that it was easily treatable and that i just needed to come down to the clinic for the meds.  the guy who called was very nice about it all.  he said my partner should get treated and tested as well and asked a question about my partners gender (i don't remember the exact question) to which i responded guys - plural.  he paused.  interesting assumption that i have one partner.

as he's telling me more about the std, i'm just half listening as my mind is racing through my last 3 months of hookups trying to figure out how this happened. 

i had recently, really just two weeks prior hooked up with two regulars, one who i've been seeing now for a long time and one who i've been seeing for a bit but is newer.  with both of them we had fucked without condoms for the first time.  with both i had really thought about it before we did so, though in retrospect i was most focused on hiv and didn't really think about other stds (clearly a mistake).  With one we had talked extensively about testing and safer sex practices with the other to be honest we didn't, we had been hooking up for a long time on a very regular basis and i just felt a level of comfort and trust with him that made me lax.  i hooked up with them just a few days apart. i'm sure many folks are shaking their heads reading this, i know it was not the best decision.  other than that in the last three months i had been safe. 

i said to the clinic guy, i am normally safe, but i had unprotected sex with someone two weeks ago, could it happen that fast?  he said yes and that's probably when you got it.  he said this std is common and alot of people have it and don't have any symptoms.  I didn't say unprotected sex with two people, i just felt stressed, embarrassed and was afraid of judgement. 

after hanging up the phone i just sat there for a minute feeling like shit.  i felt ashamed, embarrassed, stressed, and overall i just felt stupid. 

i called my best friend and told him.  i luv my best friend.  he said its nothing to be ashamed of, its just an infection, its common, if you had an ear infection you wouldn't be feeling like this.  its easily treatable.  however, he said, maybe you need to rethink this no condom thing.  to which i said i know.

all of what he said is true however i still felt like shit.  i told him that i was planning to text the two regulars to let them know so they could get tested.  he said are you sure you should do that?  what if one of them gets violent or something.  to which i said, one of them i have no worries about, the other i'm not sure but while we've been playing for a while we are very anonymous so there is little he could do if he was angry about it.

this all just sucks.  i text both of my regulars and let them know in a very non blaming way, non accusatory way, and tell them they should get tested.  the one i had no worries about sent a really nice response, which i knew he would, he said he was so sorry if it was him and that he didn't know if it was and said he hoped i was ok.  so nice, to which i responded that he didn't need to apologize and that i hoped he was ok too.  the other one at first was like, wtf, its not me.  to which i just said your probably right but i just wanted you to know so you could get tested just in case and i hope your ok.

i'm feeling really down and bad about myself.  i start to worry what if i got it from one then gave it to the other.  i start to feel all guilty and bad about it all.  again i'm talking to my best friend and he says it was as much their decision as it was yours.  you are both equally responsible. which i know is true but i still feel like shit.

later that day, i'm still feeling shitty, and all of a sudden i remember that there was one other.  this one was a total mistake.  just a total fuck up on my part.  yet somehow i had totally forgotten about it.  honestly it just slipped my mind entirely. 

i hooked up with this dude, i didn't know before we met up, but we run in the same social circles. for some reason the fact that we know alot of the same people made me feel very comfortable with him and i was lax.  we also both were very drunk, again not something i normally do with a first time hook up, but i was feeling very comfortable.  we fucked of course and we started out using condoms however there was a point where we fucked without a condom for a bit.  this was a mistake.  i made a promise to myself that while i might bareback sometimes that it would only be with regulars who i've know a while and after we've discussed testing and safer sex practices and that i would very rarely do this.  this incident was just a total fuck up. 

and i had really just forgotten about it.  now i'm starting to feel really shitty.  as i had told the newer regular, when we were discussing possibly going raw, that i used to bareback sometimes but it was too stressful and that i had been safe since.  what if i gave the std to him? (he texted me a few days later to say he'd tested negative)

i never heard from the other dude again.  we had been hooking up on a pretty regular basis for a long time, really good fucks, major hottie, we also got along as people - he's a really nice guy.   par for the course in the hook up world.  i actually would have hooked up with him again, safe only, if he had contacted me and let me know he got tested, even if he found out he had the std, yuh know shit happens.  i am very judgemental of myself less so of others, clearly my own shit. 

i know that i had been getting cocky (no pun intended) and over confident and lax.  having an std is bad enough and i know i'm just lucky its something curable, adding on worrying that i gave it to someone and having to notify my hook ups - all sucks