Shemale Transvestite

Probably one of the best stories and most popular posts on this site are the ones with a tranny surprise ending. Now shemales aren’t always about just finding straight guys who want to have sex with them, they’re looking for fun and excitement to keep their transvestite lifestyle always at maximum capacity. There’s this fucking sexy shemale by the name of Kelli who by far is one of the hottest trannies out there. She could easily pick up almost any random guy and get him begging on his knee’s for a quick nasty fuck in any alleyway.

Kelli was always a really healthy shemale so she was always in the grocery store buying fresh fruits and vegetables since she cooked all her meals always. She always goes to the same grocery store at the same time and usually sees the same people in there. She never really liked to fool around with people she sees on regular basis such as her gym. There are plenty of horny guy’s there just waiting to cum inside her but she just ignores them all. Then it happened, someone new showed up in the grocery store, and it’s a fairly small store as well so he must just be passing by. Kelli kept a close eye on him to see what he was doing but not enough to make him notice that she was looking. Guy’s tend to get all cocky when they see a chick checking them out. This dude however looked like a macho man with his army pants and tattoos. He instantly noticed Kelli and how crazy sexy she was of course not having a single idea that she was a transvestite. Once Jason saw how hot she was, the brain turned of and the penis brain turned on. He didn’t even remember what he was in the store for and all his efforts where now focused on getting in her underwear.

Kelli sensed that she “got” his attention and had this funny feeling in her stomach that this macho man would be a fun fuck and was eager to find out how easy it would be to trick him and how surprised he would be when she starts fucking him in the ass. Kelli went up to Jason and asked him if he was really in the Army and that if he was, how long he was off-duty for. That instantly got Jason turned on and he dropped the apple that he had in his hand. His eyes turned directly towards her, looking her from the bottom up, observing her slim sexy legs which lead up to her short jean skirt. He then made his way up to her tight tank top imaging what her breasts looked like underneath.

Kelli stood there in silence while Jason undressed her mentally until she reminded him that she was still standing there. She asked “Do you like what you see?” and Jason simply nodded his head like a little puppy. She then asked him if he was done shopping and wanted to leave? Of course he just left whatever he was going to buy and followed Kelli like a little dog up to her apartment where she let him suck on her perky nipples. Kelli felt her shemale cock getting a little hard so she went down to give Jason a quick blow job. She took his army pants down and pulled his underwear away to reveal his semi-hard cock with a little bit of cum on the tip. She licked it up like candy. Jason was in heaven as Kelli slowly put his cock in her mouth right till his balls.

Jason started to move his hands towards her inner thigh and removed her underwear while she was sucking him down. She pulled away and showed Jason her shemale dick and asked if he was still interested in some shemale sex. He was completely surprized that Kelli was a tranny but what the heck, he wanted to cum and he wanted to make her cum. He threw her on her stomach and started stroking her cock like he was milking a cow. She loved that he was so rough with his hands like he had never done this before. He was so surprised that she could actually get as hard as him and that her cock was almost as big as his cock. He spit in her ass and said in his mind “this is going to be my first shemale sex experience so I better make it a good one”. He then held his hard cock in his hand and pushed it deep down Kelli’s ass.