I remember the first time I had sex for money. I never intended to be an escort, but I was wanting money for my gender reassignment surgery. When I was younger I wanted to be all girl. I was not yet comfortable with my duality; with being the best of both worlds. I had some boobs thanks to the help of hormones, and long beautiful hair. I did my nails and toes, perfected my makeup, wore beautiful girly clothes. I certainly looked the part. Craigslist still had adult listings then, so I took out an ad as a barely legal college coed auctioning off her “backdoor pussy.” I made it sound like I was all girl and wanting to sell the pleasure of popping my anal cherry. My ass is my pussy. I was just shy of legal and the boy in me was not a virgin, but the girl in me most certainly was. I was amazed how many guys jumped at the opportunity to fuck my ass for the first time. And offer good money.
The guy that offered the most was obese and rather unattractive, so I went with this Latin Lothario. Tall, dark, handsome, hung and loaded. Young for the amount of money he had. I didn’t ask what he did for a living. All I cared about was that he was gonna pay $10,000 cash to fuck my ass for the first time. I felt like Brooke Shields in “Pretty Baby.” I was nervous. This was dangerous for lots of reasons. First I was fucking a stranger who could kill me. Second, I was duping him into thinking I was a barely legal teen girl. I met him in a hotel lobby for drinks first. I slipped him some X hoping he would be so high by the time we got to the room he might not notice my cock. We started making out in the elevator. It was a struggle to keep him out of my panties. No way was I gonna let him discover my cock before I got my money.
I went down on him first. Got him good and hard and convinced him the best way to do this was to just force his cock in my ass nice and quick. I laid on my stomach to hide my throbbing cock, spread my ass and told him to take my backdoor pussy. He rammed it in as instructed. He said it was the tightest hole he had ever fucked. He came almost instantly in my ass. It hurt like hell and I bled, but it was over quick and I had $10,000 cash. I felt a bit guilty, but I now know that if a guy wants to pay for a virgin, well I should take the money and run. I sold my backdoor pussy a dozen more times and amounted enough money for a sex change operation. But, the last guy who bought my virgin ass, discovered my secret. He was actually so turned on, he paid me more to suck my cock too. He had never been with a shemale and he told me I was the best of both worlds and I should never change.
Well, I didn’t. I just worked on being the best, the sexiest shemale around. Now when I escort, I get big bucks for being the best of both worlds and I hide nothing. I bet you would pay for the privilege of being with a hot tranny.
Last week I had to get X-rays. In a drunken stupor I fell and twisted my ankle. My doctor thought I may have fractured it and sent me to the hospital. The X-ray technician was a cute little Latino guy. Very flirty with me. He enjoyed taking pics of me. After he got what he needed of my ankle, he took a few fun shots. He was clueless of my pleasant present. I tucked my cock under, and posed in such a way he would be unable to see my throbbing boner.
He said my X-ray was sexier than any pinup he had ever seen. Asked if he could keep it to think of me. How sweet. He was going to jack off to my X-ray. My skeleton was going to get him hot and bothered. When he showed it to me, I was like damn, I even have a sexy ass skeleton. I got turned on by our little X-ray photo shoot and I could see his cock bulging. So, I thought it would be fun to suck his cock and have him take an X-Ray for me to keep! Now that’s a sexy skeleton
I know we could have gotten in trouble for playing around in the X-ray room but it was so hot. He had a big cock too. I wanted to show him mine, but I wasn’t sure he was ready to discover yet that his beautiful pin up was not all female. I swallowed his fat dick and sucked him off until he came. Got a great pic of my skeleton blowing his cock too. Think I may frame it. He got an X-ray of my sexy ass and I got one of his hot cock in my mouth. We exchanged numbers. We have a date next week. He will soon find out that the X-ray did not capture my best attribute. It will be a little Halloween surprise.
Today is one of those days that is about me. Just me. It’s been storming pretty badly lately, making it hard to get out. But, I have needs you know? I bet you do too. So I decided to break out my huge box of sex toys and pulled out my three favorites. A green jelly dildo; a purple suction cup dildo, and my baby blue vibrating butt plug. I started with my green jelly dildo. Its long and fleshy and thick just like a cock. I sucked it for awhile, imagining your nice hard throbbing dick in my mouth. Felt amazing. I sucked on it and stroked my cock thinking how good it feels to have a cock down my throat; how amazing it is to taste and feel cum. And when I had that dildo good and lubricated with my saliva, I rammed it up my ass and came all over my stomach.
Since I was covered in jizz, I decided I needed to shower. I took my purple suction cup dildo into the shower with me and mounted it on the wall. After I lathered myself up real good, I backed my hot ass on to the purple dildo thinking of you fucking your first tranny ass. My cock gets so hard at the thought of you shooting a load of hot spunk in me that I come again. I love getting fucked in the ass as much as I love fucking in the ass.
Since I am a horny fuck today, I get out my blue vibrating butt plug, slip it in my tight perfect ass, and fantasize about taking you. Surprising you with my panty present. Perhaps you had an inkling and were curious, perhaps I took you by surprise and didn’t give you a chance to say no. Whatever scenario, my cock is in your tight ass pumping away until I unleash a huge load in your virgin ass. If you are a good boy, I will even reach around and jack your cock as I fuck you from behind. Three hard cums in 3 hours with 3 of my favorite toys. Maybe you will be with me the next time so I can have the real thing and so can you.
Over July 4th weekend, I went to Venice Beach to visit some friends. I had heard all the freaks hang out there and a chick with a dick would blend right in. I love the beach, but on a traditional, vanilla beach, I stick out. Even in a bikini it’s hard to hide my 10 inch cock. Especially when I see all those hot men in Speedos! I decided to put on my red, white and blue bikini and a matching hat, and roller skate my hot ass right down to the beach. I met a cute little freak named Jorge. Now Jorge was wearing a Wonder Woman Speedo. Hell he had on a whole Wonder Woman outfit. Little guy, claimed he was straight and just trying to fit in with the freaks. Well, if he was indeed straight, he would not be for much longer. I was gonna have fun with my sexy little Wonder Woman.
We looked cute roller skating together in matching red, white and blue outfits. However, Jorge seemed clueless about the present in my bikini bottom. I asked him if he wanted to come back to my hotel room with me. I towered over him, so much so I could rest my tits on his head. When we got back to the room, Jorge and I smoked a joint. California weed is awesome. We started kissing and was positive he would see my dick poking out of the top of my bikini, but he was still clueless. I went down on him. Surprisingly a big package in a tiny man. Small hands and feet but huge cock. Almost as big as mine, which was now totally out of my bikini. When he came in my mouth, I stood up and well the cat was out of the bag.
He seemed a little perturbed. Actually downright angry. He tried to hit me. I was high and horny as fuck. Not to mention pissed off that a little shrimp of a man in a Wonder Woman outfit would act offended that I had a cock. I over powered him, flipped him over and yanked off his silly little Speedo and rammed my hard cock up his ass. I forced him to explore his bisexuality. He was screaming in a bad way, but he deserved my cock up his ass. Even more so, he deserved my hot spunk in his ass. I fucked him good too. No way I was letting him just walk out of my room without breaking in his tight little ass. It was so tight too. Well, maybe not as tight now.
He laid there all violated looking, crying like a pansy. I fucked his ass, I didn’t cut off his balls. Felt good to be so animalistic. I really enjoyed forcing my cock up that unwilling tight ass. I don’t do that often; but you can’t cock tease me, act like you are totally clueless when I am bulging in my panties then leave me with blue balls. Jorge learned a valuable lesson that day. Don’t pick up random strangers with a package.
I wonder if you would be so clueless? Bet you would love to find my panty surprise.
Avery and I always celebrate Sunday Funday together. Now normally we go out and pick up some unsuspecting straight guy to play with, but today we decided to watch the Steelers while playing with each other. Avery is a great cock sucker, not to mention she has the tightest ass ever. We were lazy today, but still horny as hell. So, we turned on the game, got on the couch, and pulled out our cocks. First, Avery swallowed my shaft. I mean all the way down, balls deep in her hot little mouth. She got me so hard. Apparently, I got Avery’s pretty cock hard with my hand. I always jack her when she is giving me head. She was so hard and was such a good cocksucker that I shot my load down her mouth. After that, I had to help the girl out, so I jumped on her cock with my back door pussy and let her pump in and out of me until she shot a creamy load of cum. I mean, getting fucked in the ass, while watching football is the best way to spend a Sunday.
During half time, I fucked Avery’s hot ass. Made her scream too. In a good way of course. We just fucked all day long. Everyone should be so lucky to have a BFF who is a shemale. I love Sunday Funday.
There is this guy I have known for years. Just a big bully. We went to school together when I was a traditional boy. But I was never really traditional. I mean I always felt like a girl trapped in a man’s body and that was obvious to the other school boys, Jordan in particular. He called me fag and freak and really made my life hell. He never left our city either. I have to see him sometimes at the gym. I just avoid him. The other day he approached me while I was on the treadmill. I was stunned. He didn’t recognize me as a girl. In fact, he asked me out.
I was pleasant but told him I don’t go out with strangers. He asked to friend me on Facebook in an attempt to not be a stranger much longer. Well I reluctantly agreed. I really despised Jordan, but perhaps he had changed? His Facebook feed was filled with gay bashing. I just hated him more, but now I thought maybe I should fuck him to teach him a lesson. After a few days of interacting via social media, he realized we had a bunch of mutual friends from our youth and that we went to the same school. I thought I would be sly. I asked him if he knew Carlton Heinz? I passed myself off as his half sister. Jordan actually admitted to being mean to my brother, well um, me. Then the most shocking thing ever, he admitted he had a crush on him/me in school but was afraid to admit it because he never considered himself gay. I said we are all bisexual if you really think about it. So I guess he taunted me to deflect his own feelings for me and now lives in the land of denial about his own sexuality, so he gay bashes.
He needed my help. He needed my cock. So, I finally agreed to go out with him. Jordan was attracted to me still after all these years, but he just didn’t realize it. I had to fuck him now. After a wonderful dinner and a play, we went back to my loft. We started making out and his cock was throbbing in his pants. Mine was throbbing in my panties, tucked under my ass as not to show through my dress. I went down on him, swallowed his cock. He guided my head up and down his shaft. He came in nothing flat. He wanted to pull my panties off and return the favor. I told him I very much wanted him to reciprocate but I had a small confession. He thought I was on my period or was having a personal grooming issue. He was shocked, but pleasantly so when he saw my throbbing rod. I explained I use to be Carlton. His cock got hard again almost instantly. He admitted he has been carrying a torch for me since our school days and I looked even more amazing than I did then. He fell on my cock. I could tell I was his first cock, but it still felt great.
We continued to fuck in my steam room. I am usually a top, but I was a bottom for Jordan. He clearly had been waiting a long time to fuck my hot ass and now he finally had his chance. Not sure if I like him yet, but his cock felt good in my ass. I have issue with closeted guys who can’t accept who they really are. But didn’t stop me from jacking my cock as he pumped inside me, jizzing all over my stomach and tits as he came. It was an incredibly hot experience. He got to fuck his school boy crush, I got a hot load of cum. Still hard to believe he crushed on me all these years when he was so mean to me that I hated him for decades. Guess it is no different than a traditional boy pulling the pigtails of a traditional girl because he likes her. Now we are grown up and pulling on cocks instead!
It is so nice to have a special bestie like Avery. Not only can we share men together, but we can also fuck each other. Yesterday, we picked up a couple at the sports bar we are always trolling for cock at during football season. Now, we thought a traditional couple and they thought Avery and I were just two regular hot chicks. When we got back to my place and started fooling around, we were all pleasantly surprised. The girlfriend of our stud was a special gal just like Avery and I. How hot was that? Four cocks. Yummy. In my world, 4 cocks equals a tranny train!
We didn’t waste any time. Avery, the cock sucking queen she is, got down on her knees and sucked our guests off at the same time. She double stuffed her greedy little mouth, while I took her pretty cock down my throat. She even slide a finger up each of their asses making them cum so hard. I wouldn’t let her swallow the load though. I’m a greedy cum guzzler too. I made Avery snowball that jizz with me. Once Avery came in my mouth, I was so hard I had to fuck.
I started with Avery, my beautiful best friend. I had her sit on my dick reverse cow girl so I could grab on to her lovely tits. She is so gorgeous. As I am pumping my big cock in her ass, I look over and our guests are following suit. The dude’s special girl is pumping his ass, exactly how I am fucking Avery. Really hot to watch a shemale fucking as you are fucking. Something so hot about cocks up asses and balls bouncing on balls. And shemales always groom so well too. Nice to have a smooth pair of balls to suck on. At one point we had a tranny train going on. I was in Avery’s ass, Avery was in our shemale guest ass and she was in her boyfriend’s ass.
Avery and I made sure our guests each had a load of cum from both of us. No one’s ass went home empty. But Avery got the must cum. I gave her 4 of my loads alone. She is such a hot bitch. Tightest tiniest ass around. Sometimes when it’s just girls night, I find myself hard for her. I love fucking Avery solo, but there is something extra hot about fucking her tight ass while watching her get a load of jizz in the face or shooting a load up an ass.
Would you like to get on board of our tranny train? Like we always say, two dicks are better than one!
Today was a lovely Fall day in my city. So one of my BFF’s and I decided to go to the botanical gardens. I love change of seasons, especially the beautiful colors of Fall. We were the only ones in the gardens today. It felt like a private tour. We were smelling flowers, absorbing the beauty of the trees with their vibrant orange, red, green and yellow colors. She then informed me my true self was showing. That is our code for I got a boner in my pants.
I looked around, there was no one in site. I didn’t even see any employees. So, I unzipped my jeans, pulled out my cock and began stroking in the outdoor garden while my girlfriend watched and snapped a few pictures. I didn’t really care if anyone saw me either. I always have been an exhibitionist. I was stroking furiously under a beautifully colored tree, when a couple came out of nowhere. MY BFF was enjoying my show and failed to notice the oncoming traffic so to speak. I was going to put my throbbing cock back in my pants, when the lady said, “Oh my are you one of those lady bugs?” I giggled and said, “Not exactly, but close ma’am. I am a shemale or transexual.” Her eyes got big and she asked to see it again. Of course I pulled it back out. Who am I to deny an old broad’s curiosity.
She actually touched it. Didn’t ask, just put her hand on my shaft and ran it all the way up. Felt strange, but good. My cock jumped a bit and startled her. It was amusing; like she was petting a turtle or something. Her male companion said nothing, but he was popping a chubby in his dockers. She looked at my friend and informed her, she was a very lucky girl to have such a pretty boyfriend. Once the couple passed, we had a good laugh. I was a couple’s first tranny sighting. It made me hard all over again. So my cock made a second appearance in the gardens, but this time I took no time to cum.
My girlfriend and I will have a funny story now. I have to admit though, it was pretty hot getting caught like that, especially by an older couple. Would you like to catch me stroking my pretty cock in public? If you did, how would you react?
Nothing hotter than waking up with BFF Avery and an overnight guest from partying last night. The nice thing about not being all girl is that I still wake up with morning wood. In fact all three of us did. So what do 2 hot chicks with dicks and a horny guest have for breakfast? You guessed it, cock. Avery is just as horny as I am all the time. Her and I play together often, but we do like threesomes with unsuspecting straight men. Last night we picked up this clueless well hung stud in the Strip District and brought him back to my loft. He was shocked when he saw our presents; in fact, he tried to leave until Avery put her mouth on his cock, and well he was all ours then.
Avery, as well as myself, are excellent cock suckers. Once a man feels how good we can polish a knob, they rarely care we have dicks. This guy went from wanting to leave, to begging to spend the night after having two hot shemales suck his cock. He woke up ready to play again too. Avery put her cock in his mouth as I sucked him off. Then, her beautiful mouth went on my cock as I sucked him, and eventually Avery fucked us both and I fucked them right back. That is how you spend a weekend morning. In bed naked getting your rocks off and being covered in cum. You may think you would never be with a special girl, but they all say that. Chicks with dicks are the best of both worlds. We have tits and cock and we know how to suck cock better than any traditional girl. Plus, we can fuck your tight little ass all day and all night.
Are you bi curious, maybe a sissy boy or even full on homo? Then you need Avery and myself. We love all kinds of guys, but our favorites are you straight guys we get to convert! Once you go tranny, pussy is lame.
I get horny all the time. Now, usually I can go out and pick up a guy or girl with no problem. But today, I was shut in from a major storm. There is only so much TV watching and pork rind eating a chick can do to pass the time. I had to get fucked. It was very clear from the monsoon and tornado warning, I was not going out to get fucked, and I doubt I could get someone to come fuck me. It was time to get creative. I have these French doors throughout my loft with these door knobs I have eying for awhile now. I like to put things in my ass to get off. I prefer a cock, yes or even a dildo, but sometimes I get experimental and/or desperate. Today I was both. I decided I was going to get that door knob in my ass. All I had to do was put some lube on it, and back my ass up. Simple, right? No so much. I was out of any lube. Not sure how that happened; I usually carry enough lube to supply all the tight ends on a football team.
I didn’t even have any Vaseline. But, I did have some Chapstick in my purse. I took it out and I rubbed it all over the door knob and the put some on my ass. My finger slid up my ass easily with my Chapstick lube, so I decided I was ready for my date with that ornate door knob. I bent over, spread my ass cheeks and backed right on to it like it was a throbbing cock. My makeshift lube and my horniness too k over and I got that door knob in my ass. I just started rocking back and forth on it and in seconds my cock was hard. Within minutes I was spraying a load all over my chest and face. When I get horny, I got to take care of it, or I can’t think straight. I do masturbate daily, several times a day, but I also try to get cock once a day too. Just sometimes like today, it isn’t meant to be. But that door knob certainly turned out to be a decent fuck.
By the time I was done cleaning my jizz off myself, the sun was coming out and the monsoon had subsided somewhat. I thought, why not go try to get laid. I put on a sexy little number, and headed out. But, my front steps were covered in earthworms from the storm and those things freak me the fuck out. No way was I stepping on them in my expensive leather boots. I marched right back inside, lubed that door knob up with the remaining Chapstick and fucked my ass some more. I had a few hard cums. Coming always give me the munchies too. Good thing I had some pork rinds left.
