Craigslist/Similar - Gay Encounters

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Typing up a story now, just getting the /gif/ requirements down.

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> Decide to try out CL for an encounter
> Lurk around for a bit; find a guy nearby
> He offers to pick me up for carplay
> Agree. Walk to spot and he comes by
> Get in his car and just stare
> Guy is huge, like not his dick but height
> At least 6' 5"
> Drives over to a secluded area
> He pulls down his pants
> Around 6 inches
> Start blowing him
> He looks like he's enjoying it
> He starts fingering my ass
> Asks if I've ever done anal before
> Tell him no
> He gets a grin on his face and pulls out a condm
> Opens his door and runs around to the passenger side
> Repositions me and bends me over at the passenger door
> Puts the condom on and instantly jams his cock in my ass
> ouch.gif
> He's moving at a decent pace
> Keeps telling me how tight I am and how he's loving it
> Eventually get used to the feeling and start to relax
> He starts going faster
> Faster again
> Slows after a bit then says he's about to cum
> Pulls me out of door (With ease, due to the size difference)
> Pulls off the condom and jams his cock into my mouth
> Fucks it for a few seconds then pulls out
> Warmth
> Cums on my face
> Not a huge/thick load unfortuanately, but quite a bit of spatter still
> Clean off his cock and my face
> Drops me back off at the original spot
> Go home and fap to some sissy stuff


For a comparison, btw, I am only 5 feet 5 inches tall, so he had a good foot on me.

Been really horny recently for another encounter. If anyone is in Delaware, hmu on gmail: m4mdelaware

>>10446461
>21 curious me
>into lots of diff porn, involving gay sissy shemale all that
>curious to be a bottom and see what its like
>have no female clothes to attract men as i wanted to be a sissy
>add on cl from a top wanting a sex slave bottom
>reply to add and we chat
>agree to prove myself with a blowjob and if im good enough he will be my "daddy"
>go to his place give him best bj i possibly could. 7inch cock not too thick but was good to suck on.
>after he came in my mouth told me I had proven myself and to go buy lube and condoms and come back
>went to servo and came back
>told me to go into bedroom and change
>on his bed was a blonde wig, black high heels and a tight blue dress. heels just fit but where tight
>walk out into his lounge room and walk over to him
>he throws me on couch and rips dress off me and eats my ass
>get extremely horny by this, tell him to fuck me
>he lubes up my ass and puts a condom on and slowly eases his way inside me
>first few minutes hurt as i hadnt put anything larger then a small dildo in my ass
>he comes after about 10 minutes of slowly and deeply thrusting into my ass
>asks if i want to stay the following weekend over at his, agree.
>clean up and before i leave he give me a box and tells me to practice with this before the weekend.
>dildo in box is bigger then his cock and thicker
>leave and practice every night up until weekend.

will continue with the weekend at his after work

B-bump!

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>>10447378
That's a good story, I hope the next session is just as nice! Reminds me of the first time I got dressed for anyone.

> Guy on CL wants a cockslut for him and his buddy
> Tell him I'm interested
> Asks if I enjoy dressing up
> Drive over to his motel/hotel thing
> Kinda sketchy but too horny to care
> Before I can knock one of them opens the door and pulls me in real quick
> He's a bit taller than me but much more heavyset
> Says the other guy went to get condoms
> Asks me if I like dressing up
> Tell him I have never tried
> He smirks and says, "You're going to love it by the end of the night"
> He points towards the bathroom and tells me to get dressed
> Some fishnets, a skirt, blonde wig, heels, and low-cut shirt
> Awkwardly try to dress in the bathroom
> Again, it's a motel/hotel thing so it's quite small shower/sink combo
> Come out and the other guy is there
> Another bigger guy, but nothing crazy
> Walk over best I can in the heels
> They start feeling me up and push me to my knees
> Pull out one of their cocks and put it in my mouth
> Grab the other's and start teasing it some
> Take turns blowing them both while on my knees until one of them grabs me and bends me over the bed
Cont?

>>10447482
please

>>10446461

Why is this ladys poop keep going in and out of there ass?

>>10447498
i would love to take that so called poop any day!

>>10447482
Yes!

>>10446461

sort of request but anyone have the webm from this vid?

https://xhamster.com/movies/6490689/daddy_like_standing.html

>>10447482
nice webm

>>10447482
sauce that

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>sissy
>likes the getting dolled up girly aspect of it
>have whole day/night to myself
>laser hair removal appointment for back and chest in the morning
>waxed legs for first time that afternoon
>went shopping and bought a new dress
>50s housewife style
>horny af
>get hotel room
>do makeup 50s glam style
>red lipstick
>huge lashes
>most dressed I've ever been
>looking on point
>answer CL ad from college jock looking dude
>he comes over
>sexy as fuck, muscular
>we start making out
>were both super into it
>start rubbing his dick through his pants
>get down on knees, undo belt, pull out cock
>not that big
>easily suckable
>he grabs my head and hard forces it onto his dick
>not a problem since its kinda small
>fucks my mouth
>starts cumming
>pulls out
>cums on floor
>i lick my lips and make eyes like I want to lick cum off dick.
>he looks down at me
>looks different
>tears in his eyes
>screams "fucking faggot!"
>starts punching my head
>i try to cover but he keeps punching
>i run out of room
>run to stairwell and sit for a while. shaking, crying.
>realize all my stuff is in the room
>go back, knock, no answer
>go to front desk in drag with makeup all runny from crying looking like a hot tranny mess and ask for another room key
>go back to room, he's gone

It was pretty terrifying to be honest. I haven't done anything like it since.

>>10447723
Fuck dude that sucks. Hope you're doing alright.

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> 21
> virgin
> live with parents
> watching sissy trainers all the time
> decide I wouldnt mind sucking cock
> posting ads every couple days
> not responding, just jerking to the the thought
> one guy responds with more then just, "i suck you dick"
> I decide to email back.
> we chat for a week, talking about what I like and what he'd do to me.
> I work up the balls to set a date when my parents wont be home
> day comes, having a lot of anxeity
> never got a pic of him, slight panic everytime I see someone outside my house.
> finally shows up.
> older guy, looks like a math teacher I had
> greet him, he thinks i look young? asks for id, I show him
> we sit down on the couch, have a computer hooked up to tv watching cumshot compilation
> we talk about how we wish we could be those girls taking all those loads
> he asks if im hard. I say yea and pull my cock out.
> he starts stroking it
> leans over starts sucking
> tells me to take my shorts off completely.
> i do, we change positions.
> we talking about edging in the emails so he'd suck me good for like a minute, then suck my balls for bit
> when he took it slow it was amazing, i could barely last 10 seconds
> he tried deepthroating it but im not long enough and he wasnt great at it
> after like 30 minutes he asks if i want to cum, i say yes
> cum in his mouth, he gets up asks with cum filled mouth if he can see a mirror
> goes in bathroom and looks it the load in his mouth.
> comes back asks if i want to go again.
> fuck yea, he starts sucking again. a few minutes go by
> I hear a car come down the driveway
> I stop him, just to be sure its not my parents look out window
> its not my parents but my friend
> Shit.
> Doors are locked shades are down, he'll just leave after a minute
> knock on door
> more knocks on door
> phone rings
> awkwardly sitting with half nacked with the man who just swallowed my cum
> couple minutes of suspense friends leaves

>>10447723
You deserved it.

>>10447921

>asks if I want to go again
> yes.
> Decided to go fast this time
> cum in a few minutes, he swallows
> he asks if he could jerk off
> he jerks off watching the porn, while i sit there and stroke a little
> completely forgetting the I only did this to suck not get sucked.
> he cums, awkwardly asks for a tissue
> he cleans up, gets dressed and leaves
> I jerk off
> start getting that anxiety back, what if he had siphilis or something
> take long hot shower
> go back to couch notice theres precum stains all over the cushion he was laying on.
I'd definitely do it again, it was awkward but enjoyable and I didnt do what I wanted to
Looking back on the emails, we chatting a little afterwards but I stopped for some reason.
I just wish there was another way then strangers from the internet. And I dont want something like this >>10447723

>Big butt Chubby Bottom
>Been on Craigslist but only fucked older dudes
>No preference but secretly preferred BBC
>Reply to ad about black guy want to fuck big ass.
>Send him a pic and to bring condoms and lube.
>He comes over. I freshen up and cleaned everything up.
>sits on my bed and hands me condoms and lube.
> I get on my knees.
>Unzips and he lets it out.
> Fucking 9 inches or so.
>Thick
>He face fucks me. Want some to gag.
>Spit everywhere
>Flips me over
> Lubes Me up and puts condom on
> He enters my tight hole Slowly.
>It hurts but it feels amazing.
>Beg him to fuck me harder.
>He proceeds to drill me for a while.
>Super deep. I feel it and cum harder than I ever had.
> He pulls the condom off and finishes in my mouth
> Been craving big black dick ever since. I want to have that feeling again.