Loosing Virginity

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>>5466889
take lots of pictures

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>>5466889
Communication is key! Tell her what you want, what feels good, etc. If it's your first time doing anal, especially if you haven't anally masturbated using a dildo or toys before it's probably going to be uncomfortable and maybe even painful, so tell her to take it gently, which she probably will anyways since it's your first time. Other than that, enjoy your sex anon!

>>5467024
pain on insertion? dont panic just take it out wait 20 seconds, use more lube and try again

the biggest issue is learning how to relax, tensing up makes it painful... + lots of lube

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>>5466889
>So today I'm gonna loose my anal virginity with a shemale.
Hahaha may god have mercy on your soul, dont be a fag and lose your anal virginity to a real man!

>>5467024
>>5467171
>>5467179
Ok I will try. Guys

Does anyone have the /r9k/ trans prostitute greentext

Enjoy your HIV

Good luck anon!

>>5467642

this exactly

>>5467627

I was there for that post

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>>5467627
>>5467642
>>5467809
>>5469105
>>5469105
Op Here I chikened out because the shemale looked so gross. But this shemale only have sissyfication.

>>5469776
ARE YOU FOR SERIOUS ALL THIS HYPE AND YOU CHICKEN OUT
REEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEE

>>5469827
Dude look that thing

>>5469827
Ya, but if that's the shemale in question, do you really want to remember losing your virginity forever for that swamp beast?

>>5469827
OP Here. Just no... I will waith until find a nice shemale

>>5469840
>>5469843
>>5469852
sorry for lashing out like that it's just I've had this thread open for hours waiting for something interesting to happen and nothing ever did.
desu OP I can't blame ya she looks like... jesus fucking christ if I know

>>5469908
Op Here I will take photos for my first time and mabie a video for you. I just want a good shemale.

>>5466889
if you don't do 3 or 4 you need to learn how to fuck

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>>5467627
>>5469105

Late but delivered

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>>5470385
Oh God. What do you guy thinks about this shemale

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When he shows you how deep that rabbit hole goes, remember that you have actually taking the blue pill.
The Truth? Who knows. You believe whatever you want to believe. Wake up in your bed, don't wake up in your bed.
it doesn't matter. You are already dead.

>>5472310
>>5469776
honestly would fuck them both

>>5470385
>the 1 month later
oh my god
my sides

>>5466889
Sounds hot.

>>5470385
>forces me to suck her balls for 10 minutes while she verbally abuses me

fuck thats hot

>>5472373
Wow that's pretty low man.

>Shemale

These are prostitutes correct?

If your serious about loosing your anal verginity i recommend she go's slow warms you up with some light touches then may be a finger and work up from there... Also alot of lube! more then you will need.. I find for people i go with who try anal for the first time that if you go slow work them up to a finger and go from there they enjoy it they get off they come back for seconds.. So my honest advice is go slow use a shit load of lube and if it hurts Stop anal sex should not hurt you should feel some pressure alot of plesure but never pain if you feel pain your going to hard or your not ready for that size yet.. warm up like i sad touch';s 1 lubed finger for a bit then 2 and if shes big 3 fingers i find 2 for me works on 1st times.. Just relax and enjoy it.. also use protection condom is a must!!! and if shes gonna dress you up get a mask and take some picks or video tape it nothing is hotter then a 1st timer getting his anal opened up for the first time..

>>5466889
Get a power washer first

>>5466889
Suggestions. DO EVERYTHING. Lucky bitch

Remember to deep throat that cock, and gag each time you violent hit the base. Definitely make sure your eyes are completely rolled behind your head. Also, make sure to eat sloppy joes; makes your puke extra chunky.