This is like my third story so like I have said in my last ones, it isn't all that great. It's been a while since I made a story, I apologize for that, been kinda busy and whatnot. This story is completely fictional. Just to let people know, I really don't want any hate comments or anything, if you don't like this type of story, then why read it in the first place? I do want advice on how to make it better though, the more the better, thanks =)
All my life I grew up wanting to be a girl, but wanting to be a guy too, it was kinda hard for me to explain... As a kid growing up to a teenager I had a lot of sexual fantasies, about everything, I didn't care what it was but it turned me on. I thought about fucking my mom, having sex with dogs, fantasized about alien tentacles and a bunch of other things in that category. My sexual lust was uncontrollable for me. But first, I should introduce myself. My name's Zack, I'm 19 years old, have an 8 inch dick, and I love to think about sex. Since I finally graduated highschool my life consists of watching porn, like 4 hours day since I don't have a girlfriend(you can probably guess why). All I ever think about is the weird shit, that's all that turns me on, and I soon find out, my life gets a whole lot better because of my fantasies.
I'll start with the day the fun started to happen... I was probably 16 or 17 at the time when I was living with my parents, still in highschool, and my mom, dad, and sister Megan went to the family farm for a small vacation for a week or so. They wanted me to come but there is now way I can turn down a week at home alone. They day after they had left I decided to get into some of the porn I had gotten from friends and family over the years. I was watching this great porno of two shemales having sex with a horse in every way imaginable, when I started to get bored of the same old routine of watching porn, masturbating, and cumming in 5 minutes, so I decided to try something a little bid different just for the hell of it.
I walked into my sister's room to try and find anything that could turn me on some more. First I'll talk about my sister. She was pretty hot, 15 years old, medium length blond hair, perfect size tits for her age, and an ass so tight, I've been masturbating to her for 2 or 3 years. I really didn't care about incest at that age, I thought it was awesome and it made me even hornier when thinking about fucking my own sister. But anyway, I was searching through her room for some stuff I could use to maybe lighten up my day. I started to get a crazy idea in the back of my head that was telling me to dress up in her clothes, which there is no way I could argue with that, it just made me hornier.
As I was looking through her clothes I found the perfect pair of sky blue and black panties, one of her bras, and I even found a 6 or 7 inch dildo that was an inch or so round underneath it all. I started to undress and put her panties and bra on, then play with myself. Yeah I felt a little weird, but it set the mood for me. I started acting like I was a girl, well, a shemale at least. I was sucking on the dildo, rubbing my crotch, moaning and everything. Then I got thinking, I've never really tried anal, and I was in the perfect mood too, but the dildo was a little to big for me starting out. I was downstairs, still dressed in her clothes and sucking on the dildo thinking about all the times she probably had the dildo in her pussy, and started looking for something I could break my anal virginity with. I looked at everything but it was all too big to start out with... Banana, wine bottle, hairbrush, etc. Then I seen a pen lying on the table and thought it would be perfect.
So I went into the living where the porn was still on, sat down still sucking on the dildo, and pulled my sister's panties down. I started feeling around my ass getting a little used to it down there, then I started sliding the pen in very slowly. I really didn't feel anything at first, but the deeper I went the better it started to feel. It was great, I was sucking on a probably used dildo by my sister, having anal sex with a pen, and dressed in my sisters clothes. I came in no time. After I got done cumming and cleaning up my mess I put everything back, and went to take a nap since I was tired as hell and just wanted to go to sleep since I stayed up for like the past 2 days in a row.
I woke up probably around 2 or 2:30 PM when I heard the doorbell. I walked downstairs opened the door, and there was this hot ass Asian chick there with a package in her hands.
"Is this the Stonson residents?"
"I have a package here for a Mr..... Jacob Stonson(my dad)"
"Umm he isn't home right now, he is on a vacation, I'm his son though I can just take it..."
She looked at me very strangely for a good 20 seconds without saying anything, which was a little awkward.
"Is it ok if I come in?"
"Umm ok yeah I guess so...."
I stepped back as she walked in still holding the package, and I couldn't help[ but look at her perfect ass as she walked by, still confused why she wanted to come into my house.
"You have a very nice home"
She set the package on the table. I sat down on the couch and watched her as she made her way back to the door, I thought she was leaving, but she didn't... She locked the door, walked back to the package, and started opening it. All I seen was a shit load of sex toys come out of the box, including dildos, vibrators, handcuffs, mouth gags, etc.
"What the fuck?"
"Sit down and shut the hell up Zack, your going to get to have some fun with me"
I was a little freaked out right now, didn't know what was happening or anything.
"I was watching you through the window over there and seen you liked sucking dicks and getting fucked up the ass, right?"
I didn't say anything, still confused as hell.
"Answer me!" *SLAP*
She hit me harder than fuck right across the face, her nails actually scratching me.
"What the fuck you cocksuc-"--Shup up! *SLAP*"
She pulled out a knife and held it to my throat.
"Now listen to me little Zacky, your gonna be my little bitch for the next few days and do whatever the fuck I tell you to do, or your gonna regret it, ok?"
Now... I was scared shitless, but still kinda turned on... Just a little bit...
"Good girl, now I want you to put your sisters clothes back on like the little whore you are"
She grabbed her toys and followed me up to my sisters room, and watched me as I stripped naked, and put on my sister's panties and bra again.
"Good girl, now lay down on the bed and down even think about moving"
I laid there as she started screwing around with her box of stuff, then watched as she pulled out some rope and starting tying me to the bedposts.
"This is just to make sure my little whore doesn't try anything she'll regret... Now, let's get to the fun stuff"
She crawled up on top of me and started licking me from my leg up. Actually, I'm kinda liking this!
She reached my covered dick and started to lick it through the panties for a few seconds, then started working her way up again. She came up to my mouth and stuck her tongue down my mouth licking the inside of my mouth all over, felt a little strange but I had a rock hard boner.
"Ohh looks like my little girl is getting turned on huh? Let's see if I can help even more..."
She started to undress, piece of clothing by piece, then, I seen it. She had a fucking dick! It was a shemale! I was freaked out and turned on at the same time so much you wouldn't believe it!
"You like mommy's dick don't ya bitch?"
She started to undo the ropes and flip me over so I was laying on my stomach now.
"Let's see what your hiding in these panties"
She pulled my sister's panties down and started to lick all around my ass. She licked closer and closer until she finally got to it, licking my hole up and down slowly and softly making me numb all over.
"You like it when mommy licks your tight puckered ass? Beg for me to lick it even more slave"
"Oh my God mistress I love the feeling of your wet soft tongue inside my tiny little asshole, please don't stop licking it mommy!"
"That's a good girl..."
She kept licking it for about 10 more minutes and then I felt something press against it. I felt what was pressing in it for a few seconds and realized it was her finger. She started working her finger in and out of my ass, fingering it harder and harder, soon inserting 2, then 3 fingers.
"How does it feel with 3 fingers up your ass bitch?"
"Oh my God mistress I love it, please don't stop, just fuck my ass harder and harder, please!"
"So you want me to fuck it? Ok, let's get started"
I felt her pull her fingers our and shove them in my mouth and made me suck on them while she straddled me.