It’s a Friday night and my best friend calls me up to hang out and have beers. I go, not thinking the night will be anything other than some drinking, talking and doing the dumb stuff we always do. So there we are drinking , music playing and talking about his girlfriends. Normal back and forth about how they don’t do this or that. He tells me how she doesn’t like anything really kinky and is boring. After more beers he puts on the tv flicking through the channels. He stops randomly on the end of a movie. Some softcore late-night porn comes on. He tells me how bad he needs to get some.
Feeling good and tipsy. I headed to the bathroom. I see his girlfriend’s panties on top of the hamper. They were simple black with pink flowered silk panties. It really turned me on. I looked through the hamper and found the matching bra. While looking for the bra I seen a white dress. The whole outfit just sent me over the edge. I had to put it all on. I have dressed up plenty of time by myself but at that moment I didn’t care.
Once I was dressed I didn’t care that my friend will see me. In fact I craved it. With the alcohol courage running through me and being so turned on, I walked back to the living room. What I saw confirmed it for me. There he was slowly stroking his cock watching porn on TV. He looks up at me, and just says, wow. He stands and walks over to me, never looking away from my eyes. I start to blush and ask if it is ok that I changed. He looks at me pushes me towards the wall and kisses me. I cant help but melt into his kiss.
His arms around me, his body pressed tight against me, his tongue pushing past my lips. My arms come up and wrap his neck. He slowly guides me to the couch as we keep kissing. He sits on the couch as he pulls me to straddle him. I now feel so sexy and wanted. His hands are slowly working down my lower back towards my ass. I do the same sliding my hand down to his cock. Feeling his rock hard 7.5 inch cock I break the kiss. I look into his eyes as i take out his cock and start to stroke it. At this point I feel his fingers slowly stroking my tight asshole.
Feeling his fingers there, I have to taste him. I kiss his head and slowly circle it with my tongue. I lick his cock up and down. As I take the head into my mouth he slides his hand inside the panties to get at my hole. I am sucking his cock up and down as I feel his finger enter me. I moan on his cock, pressing my ass to get his finger deeper into me. He notices and adds another. As his dick enters my mouth his fingers slide out. As his dick slide out his fingers go deep. I am moaning hard on the head of his cock as he uses his fingers deep in me.
He lifts my head off of his cock and pulls me to his lips. His tongue in my mouth, his fingers in me, I am hot and rubbing my hands all over his back. He breaks the kiss and looks into my eyes. Alls I can say is I am your sissy now. He pushes me down onto the couch on my back. He lifts the dress and starts to lick my freshly fingered hole. Feeling him eat me has me moaning and begging for more. His tongue slowly entering and leaving has me spinning. I just moan out to fuck me.
He looks up at my and asks if I am sure. I just bite my lower lip, look into his eyes and shake yes. He reaches into a draw and pulls out lube. He lubes up my hole and works it into me. I fell the head of his cock in my hole teasing me with it. I look at him to tell him to fuck me when he leans into me kisses me and pushes the head into me. I yelp with the feeling. He keeps kissing me as he slowly works into me and stops allowing me to relax and get used to it. Before I know it he stops kissing me. I look at him and he starts to work his cock in and out of me.
After a few minutes he flips me over so I am on all fours. Feeling his hands pulling me onto his cock i am moaning and loving it. I start begging him the fuck me harder and faster. He grabs my hair pulling me to look at him. He tells me I feel so good on his dick and I am now going to be his fuck toy. He spanks my ass. I am moaning, yes baby i am now yours. I feel him pushing harder and deeper into me. He wrapped his hands on my chest and pulls me to the side without ever pulling out of me. Lifting my leg as he thrusts deep in me. He whispers into my ear i am going to cum in my sissy bitch. He grabs my mouth to kiss me as he cums deep inside of me. At which point I cum too.
We just lay there both spent. At this point I am kind of scared that he might regret what we had done. Then he turns me over looks into my eyes and kisses me. Then asks if I want a drink because he wants to have a round two.
Source: reddit.com/r/Erotica/comments/j5tguc/my_sissy_fantasy_with_my_best_friend_part_1_m