Awkward Sexual Experiences

[FriendlyComments]

-Apologies if there's grammar issues I'm not rereading this-

My turn.

This past monday I met up with chick from Tinder. She goes to same college I graduated from and we had a few very brief interactions.

I was hyped to chill, she's way sexy, tall red head, big glasses, lots of tattoos. Basically "she can get it". So meet up at bar and start putting them back. We're having great non-stop conversation. Everything from anime to the social complexities on 'how long' you can/should wait before texting back in a new relationship. *I say right away*

So at the begging of the night she's saying she has to wake up early... so i figured there's no chance we hooking up... i was wrong.
By the time we split the bill she was all for me coming over.

We get back to her place and start watching Dumb and Dumber, a classic. We're cuddling and she starts complaining that she's getting sick.
I drop the true yet advantages fact that sex boosts the immune system. Within 10 seconds we're making out. 2 mins later we're both fully undressed.

I finger her until she orgasms then she gives best blow job I've had in years. (note we didn't have a condom. I failed to find one in my car. Trust me I was deep sea diving in-between my car seats before going up to her apartment)

Well this is where things go down hill. Right after I cum she gets up and starts pacing. She then informs me I have to leave.
I was cool with it. I get sleeping in your own bed by yourself. Until to figure out cuddling, getting a good night sleep next to a new person can be troublesome.

After I leave her place I get a text, literally 2mins after, saying she didn't want to move so quickly and she doesn't wanna be with someone were the pace is that quick. *note I'm translating here. It was a very incoherent jumbled mess of a text*

I'm bummed because this girl is way way way legit. Personality, talent and beauty.

So legit that's she's too legit for the 1 night stand...

Ugh. Sucks. But it was a hell of night 

[ADOLF SHITLER]

fuck it bruh you got yours and now the slut feels ashamed, mission accomplished 

[Kolostrum]

Wish I could sig Trhillho's entire post.

[KING TUT]

Expand Quote

I was talking to this ladyboy (yes, I knew from the beginning) for a while online, met him on okcupid.  I never did anything with a guy, but I figure if he looks and sounds enough like a girl then fuck it, what's the diff?  He was really nerdy and shut-in so I didn't figure he was the type to be hanging out in rest stop bathrooms.  Turns out he lives pretty close and we started snapchatting.  He looks short and skinny like a bit more chinful Alexa Chung in pics.   So I ask him if he wants to hang out and he comes over a few days later. 

He calls me to say he's here and the first time I answer I'm like terrified he's gonna sound like a dude, and I dunno if I can take that.  He puts on some approximation of a girl which was comforting, I guess.  I have to go out in the parking lot to find him and when I finally see him and I see his face and it's essentially a dude with a girls haircut; great big nose and chin; I'm like "yo!" and I am kind of struggling to not look at him again.  I keep saying like "you want to drink? We need to go get some juice or something to mix".  So we go to the store and every time he would get in front of me I would look at his ass in these girls jeans and it's so little and puny like the pockets are touching together. 

So we go back to my place and we hang out and he beats me bad at Mortal Kombat.  He's super easy to talk to though, so that wasn't a hurdle at all.  Was like talking to any other guy or girl.  I turn out the lights to watch some anime movie and look over and realize he looks way better in the soft light.  Like could totally be a night model, and start drinking... and after about 3 drinks I start to kind of rub his elbow, and he's not shying away or anything. 

Let me take a moment to address the way this dude smells.  I don't know if its the shots of estrogen or some weird perfume, but this dude smelled so fucking weird.  Like a nursing home, I think.  Not rotten, almost like mildew.  And it is so strong.

Now I start pushing up on him and I got my hand up his shirt rubbing his stomach and stuff, and I start inching a pinky down the top of his pants and this is the first realization that what I'm doing is pretty gay.  Because my finger brushes up against the tip of his dong.  I start thinking like "what the fuuuuck am I doing?? Why am I doing this?"  But I'm drunk and the train is already building up momentum.  With any girl, I'm just like "target acquired", and it's just go time.  So I kiss his cheek and I start rubbing his butt and he's kissing me back and I touch his dick and it's so weird and little, like he's wearing low rise girls pants and the thing is hard, but it's still not making it out of the top of his pants. 

He kind of rolls over and sits on me and is like "what time is it?" and I hop up and grab my phone and am like "midnight", so he's been there about 6 hours.  He goes and I walk him back to the car.  People see us and I immediately begin to appreciate how a lot gay people must feel all day every day, like "I hope they don't just decide to jump us for walking past them."  Anyway, we say goodbye and he goes.

I immediately block his number and snapchat and all that, but after a few hours I think "Dude's fun to hang out with.  We like the same stuff and he's pretty funny and all that."  So I unblock him from everything and he doesn't seem to notice.  And we talk some more and I'm like "want to hang out Monday?" and he's like "sure."  He sends me some snapchats of him in some lingerie and he looks like a skinny hot girl!  Face and all, looks good!  And I'm so fucking confused!  So I'm like "gonna wear that skirt Monday?" and he's all "if that's what you want."

So he shows up in this skirt and some weird white leather cowboy boot things and I'm just so bummed because, once again, it's a dude in a skirt and some fruity boots.  This time I just immediately start knocking back the vodka.  We're watching a movie.  We drink all the vodka, and I just starting drinking Jager from the bottle.  Which isn't abnormal, I like the taste of it, but I'm really trying to get drunk for this.  I start touching his legs, and they're like girls legs.  I start rubbing his butt and it's like a girls butt.  He's wearing a thong which makes me laugh now when I think about it. 

I start rubbing his gooch because I don't know what the fuck I'm doing.  I know what girls like, but what the shit do I do with this stuff?  So I start rubbing on his asshole... start pushing some digits in.  Rubbing his dong and stuff and I'm so bummed.  I so badly want it to be girl parts and I'm treating his dong like a big clit refusing to stroke just rubbing it with the middle and ring fingers.  I start using more and more fingers and I stop for a second and think of Band's sig of that dude greasing his hand up.  I grab a bottle of lube from the other room... I come back and start doing three digits.  Then four.  I'm literally doing my best to fist this DUDE'S. ASS.  And it starts smelling so bad like a fucking broken sewer pipe.  I just start thinking "How the fuck does GAY do this? It's so horrible."  And I can't quite get past the knuckles and he's into it, I guess?  I can feel little bits of shit going up in my nails and getting all over his ass.  Eventually he says it hurts, so I stop, and go wash my hand for five minutes.  He wants to go lay down, so we go lay on the bed.  He starts bending over and pushing his ass at me and saying "You have a condom, right?" and I am so fucking limp like a fucking shoe string no way no how that is going to happen.  So I just flip him over and I'm kissing his stomach and hips and I can feel his ball hairs brushing across my mouth and I'm biting his thighs and tugging on his ridiculously hard crooked little dong and stuff but I just CANNOT BLOW HIM, no, no-no.  So I just kind of roll off and am like "my arm's tired."  And I go back to the other room and start the movie up again (we were watching Arachnophobia).  He goes into the bathroom and I can hear him farting like a fucking whoopee cushion.  He comes out and sits down and after a few minutes he says he needs to go. 

So he takes off.  I washed my hand for, at least, another 20 minutes with vinegar, bleach, peroxide, rubbing sliced lemons and limes all over it, I boiled my ring for like 45 minutes.  It took 2 days for it to go away, or at least for me to be able to notice it anymore.  Haven't talked to him since, blocked him on everything.  Anyway, if you ever see a tranny and think "what's the diff?", that's the diff.

[close]

yo you took the gnar pretty far! my favorite part is how your internal monologue referenced both 'band' and 'GAY'. i don't think you're gay so much as slap happy.

definitely a tad gay, maybe doesn't realise he is gay yet. Straight men just get head off trannies not kiss or fondle their penises.

[summertimebluesdaddy]

Expand Quote

Expand Quote

I was talking to this ladyboy (yes, I knew from the beginning) for a while online, met him on okcupid.  I never did anything with a guy, but I figure if he looks and sounds enough like a girl then fuck it, what's the diff?  He was really nerdy and shut-in so I didn't figure he was the type to be hanging out in rest stop bathrooms.  Turns out he lives pretty close and we started snapchatting.  He looks short and skinny like a bit more chinful Alexa Chung in pics.   So I ask him if he wants to hang out and he comes over a few days later. 

He calls me to say he's here and the first time I answer I'm like terrified he's gonna sound like a dude, and I dunno if I can take that.  He puts on some approximation of a girl which was comforting, I guess.  I have to go out in the parking lot to find him and when I finally see him and I see his face and it's essentially a dude with a girls haircut; great big nose and chin; I'm like "yo!" and I am kind of struggling to not look at him again.  I keep saying like "you want to drink? We need to go get some juice or something to mix".  So we go to the store and every time he would get in front of me I would look at his ass in these girls jeans and it's so little and puny like the pockets are touching together. 

So we go back to my place and we hang out and he beats me bad at Mortal Kombat.  He's super easy to talk to though, so that wasn't a hurdle at all.  Was like talking to any other guy or girl.  I turn out the lights to watch some anime movie and look over and realize he looks way better in the soft light.  Like could totally be a night model, and start drinking... and after about 3 drinks I start to kind of rub his elbow, and he's not shying away or anything. 

Let me take a moment to address the way this dude smells.  I don't know if its the shots of estrogen or some weird perfume, but this dude smelled so fucking weird.  Like a nursing home, I think.  Not rotten, almost like mildew.  And it is so strong.

Now I start pushing up on him and I got my hand up his shirt rubbing his stomach and stuff, and I start inching a pinky down the top of his pants and this is the first realization that what I'm doing is pretty gay.  Because my finger brushes up against the tip of his dong.  I start thinking like "what the fuuuuck am I doing?? Why am I doing this?"  But I'm drunk and the train is already building up momentum.  With any girl, I'm just like "target acquired", and it's just go time.  So I kiss his cheek and I start rubbing his butt and he's kissing me back and I touch his dick and it's so weird and little, like he's wearing low rise girls pants and the thing is hard, but it's still not making it out of the top of his pants. 

He kind of rolls over and sits on me and is like "what time is it?" and I hop up and grab my phone and am like "midnight", so he's been there about 6 hours.  He goes and I walk him back to the car.  People see us and I immediately begin to appreciate how a lot gay people must feel all day every day, like "I hope they don't just decide to jump us for walking past them."  Anyway, we say goodbye and he goes.

I immediately block his number and snapchat and all that, but after a few hours I think "Dude's fun to hang out with.  We like the same stuff and he's pretty funny and all that."  So I unblock him from everything and he doesn't seem to notice.  And we talk some more and I'm like "want to hang out Monday?" and he's like "sure."  He sends me some snapchats of him in some lingerie and he looks like a skinny hot girl!  Face and all, looks good!  And I'm so fucking confused!  So I'm like "gonna wear that skirt Monday?" and he's all "if that's what you want."

So he shows up in this skirt and some weird white leather cowboy boot things and I'm just so bummed because, once again, it's a dude in a skirt and some fruity boots.  This time I just immediately start knocking back the vodka.  We're watching a movie.  We drink all the vodka, and I just starting drinking Jager from the bottle.  Which isn't abnormal, I like the taste of it, but I'm really trying to get drunk for this.  I start touching his legs, and they're like girls legs.  I start rubbing his butt and it's like a girls butt.  He's wearing a thong which makes me laugh now when I think about it. 

I start rubbing his gooch because I don't know what the fuck I'm doing.  I know what girls like, but what the shit do I do with this stuff?  So I start rubbing on his asshole... start pushing some digits in.  Rubbing his dong and stuff and I'm so bummed.  I so badly want it to be girl parts and I'm treating his dong like a big clit refusing to stroke just rubbing it with the middle and ring fingers.  I start using more and more fingers and I stop for a second and think of Band's sig of that dude greasing his hand up.  I grab a bottle of lube from the other room... I come back and start doing three digits.  Then four.  I'm literally doing my best to fist this DUDE'S. ASS.  And it starts smelling so bad like a fucking broken sewer pipe.  I just start thinking "How the fuck does GAY do this? It's so horrible."  And I can't quite get past the knuckles and he's into it, I guess?  I can feel little bits of shit going up in my nails and getting all over his ass.  Eventually he says it hurts, so I stop, and go wash my hand for five minutes.  He wants to go lay down, so we go lay on the bed.  He starts bending over and pushing his ass at me and saying "You have a condom, right?" and I am so fucking limp like a fucking shoe string no way no how that is going to happen.  So I just flip him over and I'm kissing his stomach and hips and I can feel his ball hairs brushing across my mouth and I'm biting his thighs and tugging on his ridiculously hard crooked little dong and stuff but I just CANNOT BLOW HIM, no, no-no.  So I just kind of roll off and am like "my arm's tired."  And I go back to the other room and start the movie up again (we were watching Arachnophobia).  He goes into the bathroom and I can hear him farting like a fucking whoopee cushion.  He comes out and sits down and after a few minutes he says he needs to go. 

So he takes off.  I washed my hand for, at least, another 20 minutes with vinegar, bleach, peroxide, rubbing sliced lemons and limes all over it, I boiled my ring for like 45 minutes.  It took 2 days for it to go away, or at least for me to be able to notice it anymore.  Haven't talked to him since, blocked him on everything.  Anyway, if you ever see a tranny and think "what's the diff?", that's the diff.

[close]

yo you took the gnar pretty far! my favorite part is how your internal monologue referenced both 'band' and 'GAY'. i don't think you're gay so much as slap happy.

[close]

definitely a tad gay, maybe doesn't realise he is gay yet. Straight men just get head off trannies not kiss or fondle their penises.

.
Yeah the go to move with a tranny shouldn't be stick as many fingers in the butthole as possible.  It should be get head with eyes closed than don't tell anybody ever and repress the memory deep in the banks until the next time you need to jerk it.

[shark tits]

man, all ya'll go to moves on tranny are gay

[captainfalcon69]

man, all ya'll go to moves on tranny are gay

haha goddamn, i was ripping the bong and that made me lose it. Crazy story though thrillho

[Flume]

I was talking to this ladyboy (yes, I knew from the beginning) for a while online, met him on okcupid.  I never did anything with a guy, but I figure if he looks and sounds enough like a girl then fuck it, what's the diff?  He was really nerdy and shut-in so I didn't figure he was the type to be hanging out in rest stop bathrooms.  Turns out he lives pretty close and we started snapchatting.  He looks short and skinny like a bit more chinful Alexa Chung in pics.   So I ask him if he wants to hang out and he comes over a few days later. 

He calls me to say he's here and the first time I answer I'm like terrified he's gonna sound like a dude, and I dunno if I can take that.  He puts on some approximation of a girl which was comforting, I guess.  I have to go out in the parking lot to find him and when I finally see him and I see his face and it's essentially a dude with a girls haircut; great big nose and chin; I'm like "yo!" and I am kind of struggling to not look at him again.  I keep saying like "you want to drink? We need to go get some juice or something to mix".  So we go to the store and every time he would get in front of me I would look at his ass in these girls jeans and it's so little and puny like the pockets are touching together. 

So we go back to my place and we hang out and he beats me bad at Mortal Kombat.  He's super easy to talk to though, so that wasn't a hurdle at all.  Was like talking to any other guy or girl.  I turn out the lights to watch some anime movie and look over and realize he looks way better in the soft light.  Like could totally be a night model, and start drinking... and after about 3 drinks I start to kind of rub his elbow, and he's not shying away or anything. 

Let me take a moment to address the way this dude smells.  I don't know if its the shots of estrogen or some weird perfume, but this dude smelled so fucking weird.  Like a nursing home, I think.  Not rotten, almost like mildew.  And it is so strong.

Now I start pushing up on him and I got my hand up his shirt rubbing his stomach and stuff, and I start inching a pinky down the top of his pants and this is the first realization that what I'm doing is pretty gay.  Because my finger brushes up against the tip of his dong.  I start thinking like "what the fuuuuck am I doing?? Why am I doing this?"  But I'm drunk and the train is already building up momentum.  With any girl, I'm just like "target acquired", and it's just go time.  So I kiss his cheek and I start rubbing his butt and he's kissing me back and I touch his dick and it's so weird and little, like he's wearing low rise girls pants and the thing is hard, but it's still not making it out of the top of his pants. 

He kind of rolls over and sits on me and is like "what time is it?" and I hop up and grab my phone and am like "midnight", so he's been there about 6 hours.  He goes and I walk him back to the car.  People see us and I immediately begin to appreciate how a lot gay people must feel all day every day, like "I hope they don't just decide to jump us for walking past them."  Anyway, we say goodbye and he goes.

I immediately block his number and snapchat and all that, but after a few hours I think "Dude's fun to hang out with.  We like the same stuff and he's pretty funny and all that."  So I unblock him from everything and he doesn't seem to notice.  And we talk some more and I'm like "want to hang out Monday?" and he's like "sure."  He sends me some snapchats of him in some lingerie and he looks like a skinny hot girl!  Face and all, looks good!  And I'm so fucking confused!  So I'm like "gonna wear that skirt Monday?" and he's all "if that's what you want."

So he shows up in this skirt and some weird white leather cowboy boot things and I'm just so bummed because, once again, it's a dude in a skirt and some fruity boots.  This time I just immediately start knocking back the vodka.  We're watching a movie.  We drink all the vodka, and I just starting drinking Jager from the bottle.  Which isn't abnormal, I like the taste of it, but I'm really trying to get drunk for this.  I start touching his legs, and they're like girls legs.  I start rubbing his butt and it's like a girls butt.  He's wearing a thong which makes me laugh now when I think about it. 

I start rubbing his gooch because I don't know what the fuck I'm doing.  I know what girls like, but what the shit do I do with this stuff?  So I start rubbing on his asshole... start pushing some digits in.  Rubbing his dong and stuff and I'm so bummed.  I so badly want it to be girl parts and I'm treating his dong like a big clit refusing to stroke just rubbing it with the middle and ring fingers.  I start using more and more fingers and I stop for a second and think of Band's sig of that dude greasing his hand up.  I grab a bottle of lube from the other room... I come back and start doing three digits.  Then four.  I'm literally doing my best to fist this DUDE'S. ASS.  And it starts smelling so bad like a fucking broken sewer pipe.  I just start thinking "How the fuck does GAY do this? It's so horrible."  And I can't quite get past the knuckles and he's into it, I guess?  I can feel little bits of shit going up in my nails and getting all over his ass.  Eventually he says it hurts, so I stop, and go wash my hand for five minutes.  He wants to go lay down, so we go lay on the bed.  He starts bending over and pushing his ass at me and saying "You have a condom, right?" and I am so fucking limp like a fucking shoe string no way no how that is going to happen.  So I just flip him over and I'm kissing his stomach and hips and I can feel his ball hairs brushing across my mouth and I'm biting his thighs and tugging on his ridiculously hard crooked little dong and stuff but I just CANNOT BLOW HIM, no, no-no.  So I just kind of roll off and am like "my arm's tired."  And I go back to the other room and start the movie up again (we were watching Arachnophobia).  He goes into the bathroom and I can hear him farting like a fucking whoopee cushion.  He comes out and sits down and after a few minutes he says he needs to go. 

So he takes off.  I washed my hand for, at least, another 20 minutes with vinegar, bleach, peroxide, rubbing sliced lemons and limes all over it, I boiled my ring for like 45 minutes.  It took 2 days for it to go away, or at least for me to be able to notice it anymore.  Haven't talked to him since, blocked him on everything.  Anyway, if you ever see a tranny and think "what's the diff?", that's the diff.

[matter of fact]

someone's gotta follow that so...

i'm over my friend's apartment and we're hanging out with this girl that lives upstairs, friend goes to bed and she invites me up. we're chilling for a little while and i make a move. now we're making out, bra's off, great. except i haven't eaten any food in six hours and this is seriously fucking with me. she says she can't get off when she's high so ok. she unbuttons my pants and starts sucking my dick. except i can't get hard. just wasn't happening, my stomach was growling the whole time but i was suppressing the hunger for some stupid reason? also i think her teeth got a little too involved but i'm pretty sure it was really low blood sugar or something. called it off after a few minutes then we went for a cig walk after i ate an old dry terrible, terrible hamburger. like a dry sponge.

anyway, going back tonight when she's off work. it was awkward but she made it not awkward in the end but it reeeeally sucked having her go to town on my flaccid dong

[essal]

not nearly gay enough unless it was a ladyboy.

[JB]

Expand Quote

Expand Quote

Expand Quote

I was talking to this ladyboy (yes, I knew from the beginning) for a while online, met him on okcupid.  I never did anything with a guy, but I figure if he looks and sounds enough like a girl then fuck it, what's the diff?  He was really nerdy and shut-in so I didn't figure he was the type to be hanging out in rest stop bathrooms.  Turns out he lives pretty close and we started snapchatting.  He looks short and skinny like a bit more chinful Alexa Chung in pics.   So I ask him if he wants to hang out and he comes over a few days later. 

He calls me to say he's here and the first time I answer I'm like terrified he's gonna sound like a dude, and I dunno if I can take that.  He puts on some approximation of a girl which was comforting, I guess.  I have to go out in the parking lot to find him and when I finally see him and I see his face and it's essentially a dude with a girls haircut; great big nose and chin; I'm like "yo!" and I am kind of struggling to not look at him again.  I keep saying like "you want to drink? We need to go get some juice or something to mix".  So we go to the store and every time he would get in front of me I would look at his ass in these girls jeans and it's so little and puny like the pockets are touching together. 

So we go back to my place and we hang out and he beats me bad at Mortal Kombat.  He's super easy to talk to though, so that wasn't a hurdle at all.  Was like talking to any other guy or girl.  I turn out the lights to watch some anime movie and look over and realize he looks way better in the soft light.  Like could totally be a night model, and start drinking... and after about 3 drinks I start to kind of rub his elbow, and he's not shying away or anything. 

Let me take a moment to address the way this dude smells.  I don't know if its the shots of estrogen or some weird perfume, but this dude smelled so fucking weird.  Like a nursing home, I think.  Not rotten, almost like mildew.  And it is so strong.

Now I start pushing up on him and I got my hand up his shirt rubbing his stomach and stuff, and I start inching a pinky down the top of his pants and this is the first realization that what I'm doing is pretty gay.  Because my finger brushes up against the tip of his dong.  I start thinking like "what the fuuuuck am I doing?? Why am I doing this?"  But I'm drunk and the train is already building up momentum.  With any girl, I'm just like "target acquired", and it's just go time.  So I kiss his cheek and I start rubbing his butt and he's kissing me back and I touch his dick and it's so weird and little, like he's wearing low rise girls pants and the thing is hard, but it's still not making it out of the top of his pants. 

He kind of rolls over and sits on me and is like "what time is it?" and I hop up and grab my phone and am like "midnight", so he's been there about 6 hours.  He goes and I walk him back to the car.  People see us and I immediately begin to appreciate how a lot gay people must feel all day every day, like "I hope they don't just decide to jump us for walking past them."  Anyway, we say goodbye and he goes.

I immediately block his number and snapchat and all that, but after a few hours I think "Dude's fun to hang out with.  We like the same stuff and he's pretty funny and all that."  So I unblock him from everything and he doesn't seem to notice.  And we talk some more and I'm like "want to hang out Monday?" and he's like "sure."  He sends me some snapchats of him in some lingerie and he looks like a skinny hot girl!  Face and all, looks good!  And I'm so fucking confused!  So I'm like "gonna wear that skirt Monday?" and he's all "if that's what you want."

So he shows up in this skirt and some weird white leather cowboy boot things and I'm just so bummed because, once again, it's a dude in a skirt and some fruity boots.  This time I just immediately start knocking back the vodka.  We're watching a movie.  We drink all the vodka, and I just starting drinking Jager from the bottle.  Which isn't abnormal, I like the taste of it, but I'm really trying to get drunk for this.  I start touching his legs, and they're like girls legs.  I start rubbing his butt and it's like a girls butt.  He's wearing a thong which makes me laugh now when I think about it. 

I start rubbing his gooch because I don't know what the fuck I'm doing.  I know what girls like, but what the shit do I do with this stuff?  So I start rubbing on his asshole... start pushing some digits in.  Rubbing his dong and stuff and I'm so bummed.  I so badly want it to be girl parts and I'm treating his dong like a big clit refusing to stroke just rubbing it with the middle and ring fingers.  I start using more and more fingers and I stop for a second and think of Band's sig of that dude greasing his hand up.  I grab a bottle of lube from the other room... I come back and start doing three digits.  Then four.  I'm literally doing my best to fist this DUDE'S. ASS.  And it starts smelling so bad like a fucking broken sewer pipe.  I just start thinking "How the fuck does GAY do this? It's so horrible."  And I can't quite get past the knuckles and he's into it, I guess?  I can feel little bits of shit going up in my nails and getting all over his ass.  Eventually he says it hurts, so I stop, and go wash my hand for five minutes.  He wants to go lay down, so we go lay on the bed.  He starts bending over and pushing his ass at me and saying "You have a condom, right?" and I am so fucking limp like a fucking shoe string no way no how that is going to happen.  So I just flip him over and I'm kissing his stomach and hips and I can feel his ball hairs brushing across my mouth and I'm biting his thighs and tugging on his ridiculously hard crooked little dong and stuff but I just CANNOT BLOW HIM, no, no-no.  So I just kind of roll off and am like "my arm's tired."  And I go back to the other room and start the movie up again (we were watching Arachnophobia).  He goes into the bathroom and I can hear him farting like a fucking whoopee cushion.  He comes out and sits down and after a few minutes he says he needs to go. 

So he takes off.  I washed my hand for, at least, another 20 minutes with vinegar, bleach, peroxide, rubbing sliced lemons and limes all over it, I boiled my ring for like 45 minutes.  It took 2 days for it to go away, or at least for me to be able to notice it anymore.  Haven't talked to him since, blocked him on everything.  Anyway, if you ever see a tranny and think "what's the diff?", that's the diff.

[close]

yo you took the gnar pretty far! my favorite part is how your internal monologue referenced both 'band' and 'GAY'. i don't think you're gay so much as slap happy.

[close]

definitely a tad gay, maybe doesn't realise he is gay yet. Straight men just get head off trannies not kiss or fondle their penises.

[close]

.
Yeah the go to move with a tranny shouldn't be stick as many fingers in the butthole as possible.  It should be get head with eyes closed than don't tell anybody ever and repress the memory deep in the banks until the next time you need to jerk it.

some people wait a lifetime for a moment like that.

[skate_bored]

anyway, going back tonight when she's off work. it was awkward but she made it not awkward in the end but it reeeeally sucked having her go to town on my flaccid dong

anytime that's happened it turns out way better in my favor. its come from nerves before, being sick, and of course being fucking hammered. but each time the girl has been so sweet about it, almost like a bonding experience. the best part is that the next time she will be on a mission to satisfy you, because no matter what, she took it personally.

[doublesteveburger]

thrillho for president.

[skate_bored]

thrillho for president.

yeah his story is post of the year.

[doublesteveburger]

Expand Quote

thrillho for president.

[close]

yeah his story is post of the year.

given the fact that he thought of SLAP during gay sex makes it POTY 2015 contender too.

[Paco Supreme]

Holy shit, this is one of those moments that make me glad i lurk SLAP, fuck.

[Bobby Peru]

I was talking to this ladyboy (yes, I knew from the beginning) for a while online, met him on okcupid.  I never did anything with a guy, but I figure if he looks and sounds enough like a girl then fuck it, what's the diff?  He was really nerdy and shut-in so I didn't figure he was the type to be hanging out in rest stop bathrooms.  Turns out he lives pretty close and we started snapchatting.  He looks short and skinny like a bit more chinful Alexa Chung in pics.   So I ask him if he wants to hang out and he comes over a few days later. 

He calls me to say he's here and the first time I answer I'm like terrified he's gonna sound like a dude, and I dunno if I can take that.  He puts on some approximation of a girl which was comforting, I guess.  I have to go out in the parking lot to find him and when I finally see him and I see his face and it's essentially a dude with a girls haircut; great big nose and chin; I'm like "yo!" and I am kind of struggling to not look at him again.  I keep saying like "you want to drink? We need to go get some juice or something to mix".  So we go to the store and every time he would get in front of me I would look at his ass in these girls jeans and it's so little and puny like the pockets are touching together. 

So we go back to my place and we hang out and he beats me bad at Mortal Kombat.  He's super easy to talk to though, so that wasn't a hurdle at all.  Was like talking to any other guy or girl.  I turn out the lights to watch some anime movie and look over and realize he looks way better in the soft light.  Like could totally be a night model, and start drinking... and after about 3 drinks I start to kind of rub his elbow, and he's not shying away or anything. 

Let me take a moment to address the way this dude smells.  I don't know if its the shots of estrogen or some weird perfume, but this dude smelled so fucking weird.  Like a nursing home, I think.  Not rotten, almost like mildew.  And it is so strong.

Now I start pushing up on him and I got my hand up his shirt rubbing his stomach and stuff, and I start inching a pinky down the top of his pants and this is the first realization that what I'm doing is pretty gay.  Because my finger brushes up against the tip of his dong.  I start thinking like "what the fuuuuck am I doing?? Why am I doing this?"  But I'm drunk and the train is already building up momentum.  With any girl, I'm just like "target acquired", and it's just go time.  So I kiss his cheek and I start rubbing his butt and he's kissing me back and I touch his dick and it's so weird and little, like he's wearing low rise girls pants and the thing is hard, but it's still not making it out of the top of his pants. 

He kind of rolls over and sits on me and is like "what time is it?" and I hop up and grab my phone and am like "midnight", so he's been there about 6 hours.  He goes and I walk him back to the car.  People see us and I immediately begin to appreciate how a lot gay people must feel all day every day, like "I hope they don't just decide to jump us for walking past them."  Anyway, we say goodbye and he goes.

I immediately block his number and snapchat and all that, but after a few hours I think "Dude's fun to hang out with.  We like the same stuff and he's pretty funny and all that."  So I unblock him from everything and he doesn't seem to notice.  And we talk some more and I'm like "want to hang out Monday?" and he's like "sure."  He sends me some snapchats of him in some lingerie and he looks like a skinny hot girl!  Face and all, looks good!  And I'm so fucking confused!  So I'm like "gonna wear that skirt Monday?" and he's all "if that's what you want."

So he shows up in this skirt and some weird white leather cowboy boot things and I'm just so bummed because, once again, it's a dude in a skirt and some fruity boots.  This time I just immediately start knocking back the vodka.  We're watching a movie.  We drink all the vodka, and I just starting drinking Jager from the bottle.  Which isn't abnormal, I like the taste of it, but I'm really trying to get drunk for this.  I start touching his legs, and they're like girls legs.  I start rubbing his butt and it's like a girls butt.  He's wearing a thong which makes me laugh now when I think about it. 

I start rubbing his gooch because I don't know what the fuck I'm doing.  I know what girls like, but what the shit do I do with this stuff?  So I start rubbing on his asshole... start pushing some digits in.  Rubbing his dong and stuff and I'm so bummed.  I so badly want it to be girl parts and I'm treating his dong like a big clit refusing to stroke just rubbing it with the middle and ring fingers.  I start using more and more fingers and I stop for a second and think of Band's sig of that dude greasing his hand up.  I grab a bottle of lube from the other room... I come back and start doing three digits.  Then four.  I'm literally doing my best to fist this DUDE'S. ASS.  And it starts smelling so bad like a fucking broken sewer pipe.  I just start thinking "How the fuck does GAY do this? It's so horrible."  And I can't quite get past the knuckles and he's into it, I guess?  I can feel little bits of shit going up in my nails and getting all over his ass.  Eventually he says it hurts, so I stop, and go wash my hand for five minutes.  He wants to go lay down, so we go lay on the bed.  He starts bending over and pushing his ass at me and saying "You have a condom, right?" and I am so fucking limp like a fucking shoe string no way no how that is going to happen.  So I just flip him over and I'm kissing his stomach and hips and I can feel his ball hairs brushing across my mouth and I'm biting his thighs and tugging on his ridiculously hard crooked little dong and stuff but I just CANNOT BLOW HIM, no, no-no.  So I just kind of roll off and am like "my arm's tired."  And I go back to the other room and start the movie up again (we were watching Arachnophobia).  He goes into the bathroom and I can hear him farting like a fucking whoopee cushion.  He comes out and sits down and after a few minutes he says he needs to go. 

So he takes off.  I washed my hand for, at least, another 20 minutes with vinegar, bleach, peroxide, rubbing sliced lemons and limes all over it, I boiled my ring for like 45 minutes.  It took 2 days for it to go away, or at least for me to be able to notice it anymore.  Haven't talked to him since, blocked him on everything.  Anyway, if you ever see a tranny and think "what's the diff?", that's the diff.

A couple details I thought deserved attention. I also just want to say that I appreciate the fact that you were really dedicated to go as far as you can despite seemingly never enjoying yourself for more than like three seconds at a time.

[DillAndKalis]

You're a good writer Thrillho, I read your story twice haha. The gnarliest part was definitely his ball hairs on your chin. One thing I was wondering, did it ever cross your mind to get a BJ from him?

I guess I got to throw a story in here. I was on OKcupid one day and I gave a girl my number. She was big and black and I didn't think much of it. She texted me at around 9pm that same day to see what was up. We flirted over text for a while and talked about meeting up. She asked if I was just trying to fuck. I lied and said that I had thought about fooling around but not really fucking. I had definitely thought about fucking.

I invite her over to my place but she says she is in for the night and that I should come over to hers. She gives me her address and I punch it into google maps. She lived really close to this gas station that I completely stopped going to because it's shitty and a bunch of hoods are always hanging out in front of it asking for money and cigarettes. I think for a minute about backing out but I was in the middle of a decent dry spell and she was down to fool around so I put 2 condoms in my pocket (in case we did end up going there), and a big pocket knife for "protection" in her shitty neighborhood.

By the time I leave it's almost midnight. I passed the gas station near her house and saw a bunch of dudes standing out in front. A car pulled out of the gas station parking lot and was behind me when I was going down her street real slow trying to find her house. I found it but there were a group of guys standing in the yard next door that I was suspicious of so I called her before pulling into the driveway and going into her house. The car behind me was making me nervous too, but I didn't have to pull my knife that night so I guess I was just being a suspicious asshole.

The inside of her house was really dark. She led me to her bedroom and we talked for about an hour before I asked her to suck me off. She started sucking and she was pretty good but I was taking too long so I asked her if she wanted anything from me. She said she didn't like getting head from guys and that she wanted to fuck but knew I didn't want to. I was like What the fuck because I had lied to her about not wanting to smash because I thought she would think I was an asshole or something. So I pulled the condoms out and we started fucking. Like I said, she was big, and it was dark so it was pretty difficult, but eventually we got our groove going in a couple different positions.

I almost busted in the condom but I hate doing that so I asked her to take it off and suck me again. It was pretty dope because I was laying on my back and she was down between my legs and she let me grab the back of her head and face fuck her, which was somewhat new for me, most girls don't like that shit. It was my first real experience with black girl hair. It was braided and felt brittle, I bet it can be hard to deal with. It's hard for me to finish when I'm with the girl for the first few times. I don't know if I'm shy or what but I kept getting close and not busting. Eventually she gets pretty fed up and I basically have to beg her to keep going every minute while I jerk myself off to keep it up. She says she doesn't want me to bust in her mouth but she lets me do it anyway. Shit felt pretty good, but she didn't swallow. She went to her bathroom sink to spit it out. As soon as she came back in the room she pretty much started escorting me out of her house, which I didn't really have a problem with.

After I left I got to thinking about the stereotypes that different races have when it comes to girls giving head. White girls swallow, black girls don't. You can be a little rougher with black girls while they suck you off, but the white girls I've been with don't really like that. With Asians and Hispanic girls it's a mixed bag. Any of you guys want to weigh in on this?

[Dr Steve Brule]

After I left I got to thinking about the stereotypes that different races have when it comes to girls giving head. White girls swallow, black girls don't. You can be a little rougher with black girls while they suck you off, but the white girls I've been with don't really like that. With Asians and Hispanic girls it's a mixed bag. Any of you guys want to weigh in on this?

White girls definitely give the most head, and do a pretty good job (B+) . Hispanics know how to suck dick (A+).

[JB]

Lol. Had no idea there was blowjob stereotypes.

[sleepypancakes]

Lol. Had no idea there was blowjob stereotypes.

Neither did I.

But I'm a homo and we drink that shit like protein shakes.

[nice_guy_2]

But I'm a homo and we drink that shit like protein shakes.

beautiful

[jimi420]

There's this girl I've been trying to get to know for the past couple years. We started kicking it a few weeks ago but had no sexual contact. Last night we were watching Juno at her place and drinking 4Lokos (disgusting, I know). I've also been getting over a flu so my stomach has been empty for days. We get drunk and start fucking, just going at it raw dog. After 40ish minutes I start feeling sick, start salivating more, I'm gonna ralph BUT I was also close to cumming. Well, I ended up puking all over her back, didn't get to cum. She rushes to the bathroom, I just sit there in shame. After she showers she refuses to allow me to go home, makes us a cot on the floor and gets me a bedpan. I wake up in the morning and she's cooking me breakfast. She tells me not to worry about last night and shit happens. Idk whether to ever show my face again or not because to her I'll always be that guy that puked on her while fucking.

[GOKU]

There's this girl I've been trying to get to know for the past couple years. We started kicking it a few weeks ago but had no sexual contact. Last night we were watching Juno at her place and drinking 4Lokos (disgusting, I know). I've also been getting over a flu so my stomach has been empty for days. We get drunk and start fucking, just going at it raw dog. After 40ish minutes I start feeling sick, start salivating more, I'm gonna ralph BUT I was also close to cumming. Well, I ended up puking all over her back, didn't get to cum. She rushes to the bathroom, I just sit there in shame. After she showers she refuses to allow me to go home, makes us a cot on the floor and gets me a bedpan. I wake up in the morning and she's cooking me breakfast. She tells me not to worry about last night and shit happens. Idk whether to ever show my face again or not because to her I'll always be that guy that puked on her while fucking.

You should totally show your face again, she sounds like a good sport and a sweetie! Plus she likes 4loko and raw dogging on the first jump, so you know she's a keeper

[skate_bored]

There's this girl I've been trying to get to know for the past couple years. We started kicking it a few weeks ago but had no sexual contact. Last night we were watching Juno at her place and drinking 4Lokos (disgusting, I know). I've also been getting over a flu so my stomach has been empty for days. We get drunk and start fucking, just going at it raw dog. After 40ish minutes I start feeling sick, start salivating more, I'm gonna ralph BUT I was also close to cumming. Well, I ended up puking all over her back, didn't get to cum. She rushes to the bathroom, I just sit there in shame. After she showers she refuses to allow me to go home, makes us a cot on the floor and gets me a bedpan. I wake up in the morning and she's cooking me breakfast. She tells me not to worry about last night and shit happens. Idk whether to ever show my face again or not because to her I'll always be that guy that puked on her while fucking.

anytime you feel that ashamed and embarrassed and she is still around then you know shes a keeper.

[doublesteveburger]

There's this girl I've been trying to get to know for the past couple years. We started kicking it a few weeks ago but had no sexual contact. Last night we were watching Juno at her place and drinking 4Lokos (disgusting, I know). I've also been getting over a flu so my stomach has been empty for days. We get drunk and start fucking, just going at it raw dog. After 40ish minutes I start feeling sick, start salivating more, I'm gonna ralph BUT I was also close to cumming. Well, I ended up puking all over her back, didn't get to cum. She rushes to the bathroom, I just sit there in shame. After she showers she refuses to allow me to go home, makes us a cot on the floor and gets me a bedpan. I wake up in the morning and she's cooking me breakfast. She tells me not to worry about last night and shit happens. Idk whether to ever show my face again or not because to her I'll always be that guy that puked on her while fucking.

that's so fucked!

I'm glad she's rad enough to be an adult about it. You should definitely keep that going.

[posguy]

Expand Quote

There's this girl I've been trying to get to know for the past couple years. We started kicking it a few weeks ago but had no sexual contact. Last night we were watching Juno at her place and drinking 4Lokos (disgusting, I know). I've also been getting over a flu so my stomach has been empty for days. We get drunk and start fucking, just going at it raw dog. After 40ish minutes I start feeling sick, start salivating more, I'm gonna ralph BUT I was also close to cumming. Well, I ended up puking all over her back, didn't get to cum. She rushes to the bathroom, I just sit there in shame. After she showers she refuses to allow me to go home, makes us a cot on the floor and gets me a bedpan. I wake up in the morning and she's cooking me breakfast. She tells me not to worry about last night and shit happens. Idk whether to ever show my face again or not because to her I'll always be that guy that puked on her while fucking.

[close]

that's so fucked!

I'm glad she's rad enough to be an adult about it. You should definitely keep that going.

Damn man, luckily she played it cool afterwards so you should play it cool and next time you go over, control yourself, bring alcohol that's not 4loco and make her cum at least a couple times to say sorry.

[jimi420]

Went back with a bottle of Hennesy, ate her out for half an hour as a thank you/apology. Gonna stay away from fruity canned drinks from now on

[posguy]

Went back with a bottle of Hennesy, ate her out for half an hour as a thank you/apology. Gonna stay away from fruity canned drinks from now on

[dirtyweemidden]

Expand Quote

There's this girl I've been trying to get to know for the past couple years. We started kicking it a few weeks ago but had no sexual contact. Last night we were watching Juno at her place and drinking 4Lokos (disgusting, I know). I've also been getting over a flu so my stomach has been empty for days. We get drunk and start fucking, just going at it raw dog. After 40ish minutes I start feeling sick, start salivating more, I'm gonna ralph BUT I was also close to cumming. Well, I ended up puking all over her back, didn't get to cum. She rushes to the bathroom, I just sit there in shame. After she showers she refuses to allow me to go home, makes us a cot on the floor and gets me a bedpan. I wake up in the morning and she's cooking me breakfast. She tells me not to worry about last night and shit happens. Idk whether to ever show my face again or not because to her I'll always be that guy that puked on her while fucking.

[close]

anytime you feel that ashamed and embarrassed and she is still around then you know shes a keeper.