Since my fiance and I broke up, I got really into prostate massage and got some toys to help out. I would sit for hours and watch porn and just slowly milk myself before letting my self cum. I got into a lot of shemale and ladyboy porn in the process and eventually started jerking off to femme bois and some crossdressers as well. I even mail ordered some lingerie to wear while I do it and started to shave my legs since I have a stocking and garter belt fetish. After a while more I wanted more than just toys in my ass. I wanted to have a real life encounter but didn't know how to do it but figured a gay bar was the best bet because I could likely find someone for a casual hook up who I could let fuck me in the ass. But without the lingerie I'm just not as into it and I wasn't sure if I could really do it. I put on a pair of panties, a garterbelt and some stockings under my jeans and went to a gay bar last weekend, but chickened out because I don't know much about gay culture and don't know what they think about crossdressing. I looked at a few guys and wondered what it would be like to suck their dicks but got scared, went home and jerked one out instead. Last night I tried it again and hooked up someone. He didn't seem to mind my stockings. We sucked each others dicks for a little bit, and then I let him fuck me in the ass. It was different than milking myself, but I really liked it. Now I want to do it again, but this time I want to suck more cock and actually swallow someone's load. Some people on here will call me a fag, but whatever, I bet they'd still let me suck their cocks too.

I confess. I am a straight male with a very sexy and passionate girlfriend. I love having sexy with her, eating her out, fucking her ass (which she loves) making her scream and moan... but I also fantasize often about being a sexy lil sissy, shemale, trap cock slut for a nice fit guy (or guys). My fantasy started almost 10 years ago when I expanded my horizons and started looking at MMF porn, then that turned to bi porn and eventually I started looking at CD, sissy, trap and shemale porn. I began chatting online back when Yahoo was the place to chat. I, like so many other's, posted and pretended to be female. I started experimenting, rubing my asshole while stroking my cock, which led to a finger, then 2, etc. Over the past few years I started to wear sexy thongs and thigh highs. I have purchased several dildos for to play with. I am at the point now that I chat online on Chatave and on often get on video showing off my sexy thong and thigh highs, and get off chatting as a cock slut for horny str8, bi or gay men, sometimes women too. I will fuck my ass on cam with my favorite dildo and often will finish by throwing my legs over my head as I push my dildo deep into my cock hungry ass and cum into my wanting mouth or on my face. I love the warmth and taste of my cum. I've cum on my dildo and returned it immediately to my ass so I can get cum in my ass. I get super aroused when I suck on one of my dildo as I fuck my ass with another. I would really like to experience my fantasy. I'm not looking to be humiliated. I just want to explore my sexual boundaries.

I travel frequently for work. One of my favorite places to travel to has an adult book store with glory holes. I always make sure I don't jerk off for several days so I have a big load when I get there. BTW, I love to wear panties and pantyhose. Last night I was at the book store and had on a pair of panties and pantyhose under my street clothes. Once I got in the booth, with the door unlocked, I took off my pants and started to jerk off to some great shemale videos. Mid stroke a guy opens the door, sees me wearing pantyhose and jerking off, comes in, sits down and starts watching. I am right on the brink of cumming when he grabs my cock, shoves it in his mouth all the while feeling my panty and pantyhose clad balls. I shoot about a weeks worth down his throat and he continues to suck. Somehow, I manage to shoot another load, felt like I was a teenager again. As I pull my pants up, he drops his, and what do I see, but a hard cock in pantyhose. I couldn't resist, I had to feel his cock, which was considerably larger than mine. I rolled down the top of his pantyhose and took him in my mouth (biggest one I ever had). It took him only a few seconds to shoot a small load. We talked for a few minutes and agreed to meet up in my hotel room in day or so as my schedule allows. Looking forward to playing in a room bigger than a phone booth. More to follow...

I confess that I am a man with an addiction to being a cock loving, cum craving, anal sissy slut from time to time. I often dress in my stockings, thong, and little shirt and go into an online chat room to get some attention from, well, anyone. Especially if I haven't had a rendezvous with my "friend" to satisfy my needs in a while. I love chatting about my experiences and sharing online pictures of hot girls, shemales, bisexual pics, and gay men. I also share pictures of myself playing with my cock and ass. When I am in the mood, I share my live stream and when I'm really horny, use a couple of my toys. I like doing this because it really turns me on, especially when guys will let me watch them stroke their cocks too. At the end of the night, my goal is to get so aroused that I have a big load of cum to shoot. I like to cum right into my mouth with either fingers, a dildo, or a butt plug in my ass. I cum so hard but it satisfies my wanting mouth and tight little ass.

So...I met a "gurl" online, after some time, she says she would like to be my little cum slut, I asked what she meant, she stated she would do as I say. i asked how would I know as she was a long way away from me, she said she would video/pic proof...going forward, she hit me up while she was at a party(I heard lots of laughing and music, I thought what a good time to see if she was serious, I told her to send me a video of her sucking random dick....She did it! This was ongoing for a few weeks as I tasked her over and over....turns out she was a spun shemale slut! She asked how I felt...well I have her fucking in the train station, getting cum dumped on her, from cab drivers to abandoned buildings
A lot of fukked up shit...lol All this and hav never met her personally...I had her posted on another site..took it down, but you guys are freaks....ENJOY

I confess that I've always wanted to be dominated by a shemale. I am a straight guy who wants to meet a girl and then while having sex find out she has a dick. It is a sweet fantasy that I would love to some true. To be deepthroated and fucked in the ass by a shemale would be amazing. Then to feel the hot cum down my throat. wow it would be something

I have a confession: I am a 23 y.o. student at ISU ("Which one?!" Aha, you'll never know!) and I looooooove shemale porn!

I've always been bi-curious, and I really like to watch lesbian porn. Usually only if I haven't had any dick in a LONG time or if I'm a bit tipsy, though. But something about shemale porn...mmmmm.

It's like the best of BOTH worlds! Sexy, curvy women, but with hard, sometimes really thick cocks! I like to watch trannies get fucked by guys and watch them suck their dicks, just like in a normal porn, but I also like watching girls get fucked by trannies, too. It's the allure of lesbian strap-on porn, but better, because it's REAL - no plastic dildo. If I ever met a passable enough shemale, I'd *totally* date her! At the very least, I want to find an older guy who would play top in recurring threesomes with a tranny. ^_^

What I would like an answer to, though (if anyone does know it), is why it seems that shemales NEVER cum a whole lot in porno. I know that if a guy has a lot of orgasms in a short period of time, he cums less and less - gotta give it time to refuel, lol - but is that what's going on with these 'girls'? Are they just so oversexed that when it comes time to film, they've got nothing left, as it were? Or do all the surgeries and hormones mess with how much cum they produce?

I'm not into biology that much, so I don't know details, but I am curious. I guess I got off on a wild tangent. I really just wanted to confess that I love looking at sexy, passable shemales and I hope to have a LTR with one some day, or at least with a guy who likes to fuck them as much as I want to! C:

I confess. I am a straight male with a very sexy and passionate girlfriend. I love having sexy with her, eating her out, fucking her ass (which she loves) making her scream and moan... but I also fantasize often about being a sexy lil sissy, shemale, trap cock slut for a nice fit guy (or guys). My fantasy started almost 10 years ago when I expanded my horizons and started looking at MMF porn, then that turned to bi porn and eventually I started looking at CD, sissy, trap and shemale porn. I began chatting online back when Yahoo was the place to chat. I, like so many other's, posted and pretended to be female. I started experimenting, rubing my asshole while stroking my cock, which led to a finger, then 2, etc. Over the past few years I started to wear sexy thongs and thigh highs. I have purchased several dildos for to play with. I am at the point now that I chat online on Chatave and on often get on video showing off my sexy thong and thigh highs, and get off chatting as a cock slut for horny str8, bi or gay men, sometimes women too. I will fuck my ass on cam with my favorite dildo and often will finish by throwing my legs over my head as I push my dildo deep into my cock hungry ass and cum into my wanting mouth or on my face. I love the warmth and taste of my cum. I've cum on my dildo and returned it immediately to my ass so I can get cum in my ass. I get super aroused when I suck on one of my dildo as I fuck my ass with another. I would really like to experience my fantasy. I'm not looking to be humiliated. I just want to explore my sexual boundaries.

looks like i have me a new young bitch to fuck now.
i was at the tire shop today getting new tires on my truck when a sexy little shemale there think she was getting a flat fixed not sure and dont care.
i walked out to smoke and when i did a couple minutes later she came out to smoke also. i was about to say hi when out of the blue she ask are you SO AND SO i said yep. then she just out right said i need you to help me. then she told me she is a bottom virgin. and was told that i wouldn't hurt her. damn i felt great hearing that.
i told her when my truck comes out i will give her my address and she can come by anytime. and she told me she knows where i live and she just needs me to tell her when.
so i said do you mind if people are there or do you want to be alone. she said alone at least the first time. so i told her 7 pm where that and no panties and be clean shaven if she isn't. she said she was.
and let me tell you she showed up at 7 pm on the dot.
i figured she would be shy when she came in and was a little but not near as shy as i thought.
she told me his G?F was the same size as him. thats why he dates her and she thought something was up with him but wasn't sure until he went out of town for 3 weeks and came back with B cup tits the same size as hers. she packed her bags and left that day and he is wearing what she left behind. then one of his friends tried to rape him with no lube but couldnt get it in but hurt his ass so bad its taken him another 2 months to even try to bottom again. now he said he has sucked alot of dicks and topped about 5 guys but never bottomed. then he heard i will be gentle. and really wants it so i said no trouble. took her by the hand and stood her up and slipped her shirt off and sure enough there was some nice little perky tits. i leaned down and start licking at her neck and worked my way down to her tits. as i did i reached under her skirt and started touching her penis and rubbing it not touching the balls. then as i went down some more i removed her skirt to the floor and there she was buck naked standing there with a almost 6 inch skinny hard cock pointing at me.
i cupped her balls and started walking to the downstairs bedroom we walked in and i set her on the edge of the bed and dropped my shorts. she reached out and took ahold of it. and i pulled away and said no this is your night then i laid her on her back legs hanging off the edge of the bed and i set down in front of her and started licking her cock and balls after a couple minutes i put her feet up on the bed also. that hole was begging my tongue to lick it so i did then i moved up to ther tiny little balls and started licking them again and before she knew it i had 2 fingers up her ass playing with her prostate. and she came so hard it hit her in her own face i told her to clean herslef up and she started wit her fingers cleaning up and i told her to lick them clean and she did i did that for about 5 more minutes
i got on my knees leaned over and started ducking her tiny tits. and let the head of my dick touch her hole then i i moved up a little more and gave then sexy lips a good licking and i was about 1 to 2 inches in her tight ass then i gave her a big kiss on the mouth and i was balls deep in her. and i have fucked and been fucked enough i can hit the prostate anytime i want to and i picked up a mirror and told her to look and as soon as she was i was in her she came again. i was making love to the virgin ass Not fucking it or Pounding it. i was making love to it with lots of lube and she was loving it.
i knew if she showed up i was going to need help so i took a little blue pill as she drove up the driveway and now it was working great and no plans on going down anytime soon.
then i got her on her hands and knees and started fucking her again and fuck if she didn't come again a 3rd time and never touched her dick one time because i told her not to. thats when i told her its my turn and i filled her sweet ass with a large load of cum . then i took her by the hand and lead her to the shower and i gave her a shower from head to toe. i cleaned her up nice and sweet.
i watched her get dress and about the time she slid her top on my friend Bob showed up and she was getting ready to leave and i told her she need to kiss it goodby and from now on when she comes over she needs to kiss it hello and good bye before she leaves and she looked over and bob and he leaned in and kissed it hello so she leaned over and kissed it goodbye. and before she left i told bob to show her what she can have anytime she wants it.so he pulled out his 8 3/4 in fat cock. she got a shock look on her face. i told her its up to her noone is forced to do anything they dont want to here. never.
she said she would like to come back and i told her if she sees my truck i'm here. but there might be someone else here. but if she wasnts to be alone we can go to that room again. if not we can fuck infront of everyone that is there man and women. from 18 to 84 we had a 87 year old that would come join in sometimes but sorry to say he passed away a few years back. and we dont care the color of the skin if they are skinny tiny or big and fat. male or female. just no drugs we see one track there out of here and will never be allowed back. she said great.
i cant wait until that sexy little thing comes back because i want to know her name.