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To begin, I frequently crossdress (stuff like skirts, thigh highs, if you’re into femboy shit you know what I’m talking about) mainly because I feel more comfortable in clothes of the opposite sex and most of my friends know about it. Though I’m not comfortable wearing fem clothes around my other friends, I only ever really feel comfortable cross dressing around my bestfriend since he doesn’t really give a fuck. One day, I come to his house to hang out. I go out in typical clothing cus I’m shy when it comes to wearing fem clothes in public. I have a bag with my fem clothes in it so I could switch clothes at his house. I reach his house, knock on the door, say hi to his mom, and go into his room. At this point, he already knew my “routine”. I would go into the bathroom, change into fem clothes and plop on his bed then we would play games on his ps4 or just talk about anime and games and stuff. That’s how it all the time went.
But this time, it went a lil differently. I do the usual “change into fem clothes and plop on his bed” routine (I changed into a pink crop top with black shorts and thigh highs for anyone wondering) and I was expecting him to turn on his ps4 so we could play, he didn’t. He just sat beside me while on his phone. I don’t know if he felt sexual tension when he sat down but I DEFINITELY felt it.
But nothing was happening. It was just silence for 2 minutes. Then, he asked me if I go out in fem clothes. I said no. Then he said “if start going out like that people might mistake us for girlfriend and boyfriend” I jokingly said “bro, you have a crush on me or something?” then he said, with a cheeky fucking smirk on his face “maybe”. The sexual tension went to the fucking moon at this point. I nervously laugh then he laughs then I grab one of his pillows and begin snuggling them out of embarrassment. He then LAYS RIGHT NEXT TO ME and asks “what time are you gonna go home?” I said “around 4pm” and at this point I knew what this fucker was up to. So I said faintly while leaning in to his ear “dude, if you wanna do it with me just ask” he turns his head to me, we stare for like 5 seconds then I, with the little amount of courage I had left, went in for a kiss. We kissed, tongue stuff, I started caressing his erect cock through his pants then after 2 minutes of smooching, I worked my way to his dick. Started jerking it, caressing the tip then it just turned into a full blown blowjob. Idk how long i was sucking his dick but all I knew was that it was the first time I sucked a dick that wasn’t silicone and I was in bliss. I stop to catch my breath. I knew was prepared for dick. I ask if he had some lube and lo and behold, he does. He starts putting lube on his dick, i got some lube on my hand and started fingering my ass. Then, while I was in the doggy style position, he started putting it in slowly. The thrusting started off slow but as time went on he kept going faster and faster. I didn’t even know he knew how to have sex but it felt like I was being fucked by a pornstar. He kept fucking me harder and faster each thrust I couldn’t keep my mind straight. Then we switched to missionary. He didn’t begin slow, he went fast the second he put it in. It kinda hurt but omg it felt so good. He put his finger in my mouth too and this wave of euphoria just showered over me. I love getting fucked like this. Fast and rough. We started doing other positions like cowgirl and such but he didn’t slow down. He kept going like a machine it was amazing. This guy, who has never had a relationship, is fucking me so good that I lost my train of wondered. Maybe 2 – 3 hours later (idk how long we went on it was probably around 4 to 5 hours long but I doubt it) he finished on my face. After about a minute of us catching our breath, I go “hey, if you want to do this stuff again, I’m free on the weekends” and that’s that. I guess this what you call friends with advantages huh.

NSFW: yes

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