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Planning first sissy encounter with someone i know.
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My friend always talks about how we should smoke weed together and iā€™m pretty sure heā€™s bi or at least finds me hot. When he gets drunk he always asks for a kiss and even when weā€™re sober he sexualizes me but that could just be seen as two dudes fucking with each other. He asked my roommate one time if he thought i was hot and just gives off the vibes that he would be down if it came to it. Finally i worked up the courage to ask him to smoke yesterday and we are doing it today. Iā€™m always insistent on paying my friends back and today im going to act like i have no money. Iā€™ll offer a ā€œlast optionā€ or blowjob in this case as an alternative as a joke and heā€™ll likely joke around with me about it. Once weā€™re done smoking iā€™ll bring it up again and say i really wish there was some way i could repay him to help him out. Heā€™ll bring up the last option again and i wonā€™t back down about it saying ā€œim a man of my wordā€ or ā€œyou gotta do what you gotta doā€ and heā€™ll joke around and be ask if i really mean it. Iā€™ll push it further and say ā€œwell i canā€™t do anything while you have pants onā€ and if at that moment he drops his pants iā€™ll start sucking his cock. Hopefully if all works out then iā€™ll be able to give him a blowjob best case scenario he ends up fucking me in the ass and asks me to stay and smoke more weed with him. worst case scenario he figures out iā€™m gay and i donā€™t even get to give him a blowjob.

Small Update: He texted me last night saying we are going to get sooo high so i agreed and he said he was excited. So i responded saying ā€œim excited to get really high and have sex with youā€. which made him say ā€œwait actuallyā€ and i told him that im a man of my word. So im already hinting at it and have him thinking about me.

Final Update: Unfortunately it didnā€™t work out i never even got the chance. i started it off good and offered him his blowjob and we joked around about it but he had two other people there constantly. I kept trying to get him alone in his room but by the time the other people left we were both extremely high and tired. I even made sure to touch his dick a couple of times when his pants were on we were watching a scary video and i reached over and put my hands on his crotch and told him i was scared. I just never even really got my chance to try which makes it all the worse. On the up side this was my first time wearing fishnets, panties, and even a compress crop top outside even if it was under my regular clothes.

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9 months ago