Tag: shemale phone sex

Let’s Take A Test Drive

shemale phone sex zettaI have known her for years. Not bad looking, wonderful personality, great sense of humor, very smart and also very gay. She has never dated a boy that I know of. Never kissed a man that I know of. She has always known that she likes women and has never been ashamed to admit it or hidden it in any way. It is one of the things that I admire the most in her.  Just as I have always accepted her for who she is, she has done the same for me. So when I started transgender surgery and I was so scared she was always supportive and by my side. I couldn’t ask for a better friend. The other day when she was over for a girls night of dinner and a movie, I had no clue that it would turn out like it did. After the movie she looked at me very seriously and said that she would like to try fucking a dick. She said that real men disgust her and the idea of sleeping with a body covered in hair was not something she could even stomach. My heart sunk, I knew what was coming next and was not sure how to handle it. Sure enough she asked me if I would be willing. Her reasoning was that I was a beautiful woman, soft and sensitive, but since I still had a dick and she knew I used it frequently, why not try it with me. I have always found her attractive in so many ways that my dick had a mind of it’s own and even though my mind was screaming “NO!”  My cock was rock hard and very visible. She asked me to teach her how to suck cock, how to handle it like a girl would. In the end she liked it more then she thought she would and I liked it more then I care to admit I did. I guess I will have to wait to see what happens next.

Tranny Phone Sex: Sex Shop Sex with Carla

tranny phone sex hot shemaleI hate winter. I especially hate blizzards. I need to be fucked or fuck on a daily basis. So when 3 feet of snow comes down on my city, it cuts off my access to cock. Day 8 of no cock. I felt ballistic. So, I decided to go to the sex shop around the corner from me. I needed some dildos if I wasn’t going to get any dick. I put on a snow bunny outfit, and trekked around the corner for some makeshift cock. When I arrived, the store was dead. Guess the blizzard has been bad for business.  The clerk was excited to see someone. He was cute too. I explained my predicament. He showed me to the sex toy room. In fact, he suggested I try out any I wanted before I bought them.

I gave him a little show. I selected an array of dildos, all big too. And right there on the storeroom floor, I began fucking my ass to see which ones felt the best. After 8 days of empty ass syndrome, anything would have felt good in there. But, I found a few that that got me off well. I was so lost in fucking my ass, that I failed to notice the young clerk furiously jacking his cock as he watched me. Here I was fucking toys, when I could have a young hard cock. I looked at him and said, “Stop jacking, start fucking.” He ran over to me and slid his cock right up my greedy ass. He admitted he was straight, never fucked a shemale before. In fact, he thought I was all woman when I walked into his shop.

He fucked me good despite never having mounted an ass before. He even reached around  to stroke my throbbing cock too. I shot such a big load, I covered a wall of DVDS in cum. It had been a long time since I came. I really need something up my ass to drain my balls completely. He shot an equally large amount of jizz up my ass. I bought a butt plug too. I wanted to keep his cum inside me for awhile. I bought 6 dildos and a but plug. Blizzard supplies. Fuck milk and bread, I just need ass toys.

The little clerk told me to come back tomorrow if I needed fucked again. Until this snow melts, and I can get to dick and dick can get to me, I will be getting some sex shop sex.

Tranny porn pictures making you wet?

tranny porn pictures Mariana

I’m not your every day girl. Outside, in public, I may seem like a perfectly sweet young thing, a girl who does normal girl things and has normal girl desires.

But once you get me behind closed doors, you will find I want much, much more than your average little girl. I am all woman, and then some. I will make you bend down suck my sweet tits before you get a taste of the main course.

And once you see this massive, throbbing, 12 inches of fuck flesh I have waiting for you, I know you will want it. But I don’t just give it away. Oh, no, my mama raised me with manners. If you want a treat, you must ask nicely, and we shall see what collection of treats I might have in store for you.

Would you like a taste of my delicious cock, dear boy? I know you would. All you have to do is ask. And don’t forget the magic word!

Naughty Secretary Phone Sex: Shemale Office Party

Naughty Secretary Phone Sex trannyA fellow tranny friend of mine got me hired on as a temp in her office. Just through the winter months, I am going to be a secretary with her in a busy medical office. Friday, we got stuck at work because a blizzard came through Pittsburgh. It was just us and this account executive that were working overtime. While we were waiting for the plow trucks to come out, we partied with some Fireball Whiskey I had stashed in my desk for just such an emergency. Pretty sure Jim was clueless about our special nature. But he was about to get a double surprise.

We all started making out, and before long, two naughty secretaries were sucking his cock. He has a decent cock too. More than enough for two tranny tongues to devour. We were swallowing his cock, playing with his balls, when my 10 inch cock starting sticking out from my skirt. I unzipped my skirt, and stood in front of him in my sexy lingerie with my hard cock. Trina did the same thing too. Standing before him were two sexy shemale secretaries.  I thought he might be upset that we concealed our identity, but he couldn’t wait to fuck us both. He didn’t want to get fucked sadly, put he pumped his big hard cock into both our asses. When he fucked my pretty tight ass, I sucked Trina’s cock and vice versa. It was so hot. I had cum running out my ass, and my mouth. Not a bad way to spend a Friday afternoon snowed in.

After a couple hours of fucking and sucking, we got word that the main road had been cleared. We decided to keep partying for a bit longer. I loved being a bottom for a change. How would you react if you discovered your sexy secretary had a 10 inch cock?

Give Yourself a Cock for Valentine’s Day

shemale phone sex big dick trannyWanna give yourself a present for Valentine’s Day? How about my pretty cock? I am the best of both worlds. I have nice tits and a pretty face with a killer body. Bet I am hotter than your girlfriend or wife. But, unlike your female companion, I have this nice hard cock. Give yourself my love rocket!  How many times have you found yourself wondering what it would be like to have some dick? Thinking about how good it would feel to bend over and submit to a guy or better yet, a hot shemale? Have you asked your girl to play with your ass? I bet you have trouble sustaining an erection with boring old missionary sex.

I bet if you have dick issues, it is because secretly, you want some cock. You don’t know how to get it, don’t know how to talk to your woman about your bi curious thoughts. Well, I am here for you and your ass. My long hard cock up your ass,  and down your throat is the best gift you can give yourself this Valentine’s Day. While your woman is out with her girlfriends getting her freak on at “Fifty Shades of Grey,” get your freak on with me.  I promise not to tell your girl you love a hot load of jizz up your ass.

What are you waiting for? My hard cock is waiting for you Valentine.

tranny phone sex hot shemale

Happy Ground Hog Day: Let My Cock Cast a Shadow on Your Face!

shemale phone sex pretty trannyI have a Groundhog Day ritual I have been practicing for a few years now. I hate winter. I have too hot of a body to cover up. Don’t you agree? I’m from Pennsylvania, so every year I travel to Punxsutawney for the festivities. I get a hotel overlooking where Phil makes his appearance. The day before official Ground Hog Day, I pick up a guy in the hotel to fuck. I make sure he stays the night with me. I love fucking on balconies in the morning as the sun is rising. Makes it really hot if there is an audience, and the morning of Ground Hog Day, there always is!

You see, if my ten inch cock casts a shadow on the face of the dude I am about to skull fuck, I know Phil will not see his shadow, which means a shorter winter. My cock is big and thick, and should cast a shadow at sunrise over any guy’s face. My cock casts the shadow instead of Phil. It was working until today!  I had a young stud on the balcony this morning sucking my huge cock. The sun was shining even though it was freezing out.  Now I’ve been cold before, but never had shrinkage. I don’t ever get turtle syndrome. My stud was sucking the hell out of my rod too, but no matter how I positioned myself, no cock shadow this year.

tranny phone sex hot assI knew what that meant. Six more weeks of winter. Sure enough Phil saw his shadow since I did not and cinched what I already knew. I gave up on trying to keep winter at bay, and took my stud into my hotel room to fuck in the warmth. We got a steamy shower going, and I fucked his tight ass against the shower wall. Gave him a big load of cum.  If I am going to have to hide my hot ass for six more weeks, I am going to spend winter in bed, fucking. No better way to stay warm than with a hard cock in your ass or mouth. Body heat is the best kind of heat around.

Join me in staying warm for the next six weeks. I’ll give you all the hot loads of warm cum you can handle! Let my massive hard on cast a shadow on your face. Happy Ground Hog Day!

Game On Big Boy

tease and denial phone sex zettaI am not much into football but when he approached me with a bet I decided to take it. No matter what the out come of the game I am going to enjoy every minute of this.
Five thousand dollars is on the table. That would put a big dent in my surgery fund.
Here is the deal. He is into tease and denial, edge play, but he can never find anyone that makes it last long enough to satisfy him. So he is coming over for the Super Bowl game. If I can tease him for the entire game and not make him cum he will give me five thousand dollars. I have to be touching him in some fashion the entire game with the exception of half time. If I can make him last all the way through the game, I get the five thousand.
Now for the side bet. He told me to pick a team, if my team wins then he will fuck me when the game is over and if his team wins then I have to do what ever he wants so that he can finally cum after all that teasing. he won’t tell me what that is.
It doesn’t really matter, either way I win for sure!
So it is game time baby, Sunday is the day!
By the way he let me pick first. I know nothing about who is playing so I picked the team with the prettiest helmet. I picked the silver ones with the red white and blue man on the side. I didn’t like the dark green color and the mean looking bird on the other one.
Do you think I might get fucked for all my effort on top of winning the five thousand?

National Hugging Day with Carla: Let Me Hug Your Cock with My Mouth and Ass

 

shemale phone sex big cockApparently it is National Hugging Day. I didn’t know there was such a thing. I suspect it’s just another created Hallmark type day to get folks to spend money. I was out last night, well technically early this morning, at a club when this cute guy informed me it was National Boys Hug Girls Day and that he was under obligation to hug me. I indulged him. He was wicked cute. He had no idea when he gave me a big bear hug, that I was a special girl. I danced with him quite a bit. He said dancing is really just hugging to music. Never thought of it that way before.

bisexual phone sex tranny sexHe had some serious dance moves, but the more he pressed up against me , the more he hugged on me, the harder my cock got! He had no idea that it was actually National Boys Hug Boys day! He kept telling me I was the most beautiful woman he had ever seen. I was beginning to feel a tad bad about concealing the special factor tidbit from him. But, in the past, the majority of straight men who have hit on me never freaked out when they found out my secret. So, I stopped letting guilt creep into my head and had fun hugging on the dance floor with him.

tranny phone sex anal sexClosing time hit and he wanted to take me home. My cock was rock hard. No way he couldn’t feel it in that skimpy little dress I was wearing. We grabbed a bottle of wine, and head back to my loft. We started making out, of course I unzipped his pants to give him some head. My cock sucking skills blew him away in more ways than one. “Wow, are you like a porn star? No one has ever blown me like that,” he said. I coyly replied, “That’s just my mouth hugging your cock.” He wanted to see my body so he could lick my pussy.  I tried explaining about my back door pussy, but he really didn’t get where I was going. When I took off my dress and he saw my cock peeking out of my panties he got it. His eyes got really big. He couldn’t believe I was not all girl.

anal phone sex bi curiousI assured him I was all girl, just a special girl. I suggested his mouth hug my cock. He paused for a moment, looked at his hard rod, then at my smoking body, and fell to his knees and hugged his first cock. Once he got the hang of it, I never would have known I was his first. Things really heated up then. I hugged his ass all morning long. He even hugged my ass too. National Hugging Day may be my favorite  silly holiday now. I’d love to hug your cock all day too!

Anything You Can Do … I Can Do Better!

Shemale Phone Sex

The whole day started off in a rush, there was entirely too much going on. My sister was getting married and I was late to her rehearsal dinner because I missed my flight. So typical of me to let work hold me from my family once again. I was rushing off of the last flight and just had to head into the bathroom, hell I was already late. Not even paying attention I ran right into the men’s bathroom. I was in too much of a rush to go and wait in the women’s line and besides, the men’s room was empty.

I walked right up to the urinal pulled my skirt up and pulled my cock out, closing my eyes and enjoying the release I’d forgotten I was out in the open in the men’s restroom. The far off gaze he had on my dick startled me when I opened my eyes. Before I could reach the sink to wash my hands he was begging me to fuck his wife. He pulled out his phone and she was a hot bitch, I was sure he couldn’t have been fucking her right. We exchanged numbers and I was off to see my Bridezilla sister.

After the dinner I needed to release some tension bad, so I called Mr. Fuck My Wife PLEASE and headed straight there. I got there and she was waiting for me in nothing but a white lace thong, her tits were sitting so nice, the site of her was making my cock hard. I grabbed her by her chin and licked her mouth, shoving my tongue deep inside. I felt her sink into my hold and grabbed her ass tighter. I knew she was going to be such a good fuck. Pushing her hand under my skirt she eagerly grabbed my cock and moaned loud in my ear. I grabbed her little bubble butt and pushed my cock right onto her pussy.

She was on her knees sucking my cock like it was all she ever wanted. As she was sucking my cock trying to get me to cum, I told her I wasn’t going to fuck her until her husband begged me to shove my big black cock in her pussy. She looked at her husband with desire and need, he came to her rescue begging again. I bent her over with her face in his lap as he begged me to fuck her harder. I grabbed her waste and she pushed her ass back on me as she came all over my cock. I could feel her nut dripping down my balls and making a puddle between my legs. The mess was making me want to cum deep inside her needy pussy, she felt my dick stiffen hard inside her and she begged her husband for me to cum inside her. He was begging for my nut as I fucked her harder and harder, pushing my cock so deep inside her juicy pussy. I pulled her head up out his lap so her could see her eyes as I gave her all the nut I had in my big black balls.

He was rock hard watching his wife take all of my huge cock. Knowing he could never fuck her like that or ever get the chance to see that look on her face again without me, he asked if I could help him again. I could never resist a begging man… 

My Own Private Sissy

sissy phone sex analAs a grown ass woman, well special woman, I don’t ask much for Christmas. But this year, I wanted a sissy. My very own sissy I could dress, humiliate, shame and use.  Not sure why. I think because when I was young, being forced to live as a boy, I was not allowed to play with dolls, and sissies are sort of life size dolls, but better because they can do shit for you. My company here has a site sissy and the girls have so much fun taunting and laughing at her;  I decided I wanted one of my very own. The only thing I asked Santa for this year was a sissy. Sure enough, under my tree was a sissy just for me.

I dressed her as a pretty little sissy shemale helper. It was like she was my private Barbie doll. I dressed her from her pretty red undergarments, to her slutty little Santa dress. Even put a wig on her and did her make-up. She was to be my assistant of sorts. We began with her shaving my body. I like to remain hairless from my head to my toes and everywhere in between. She gladly shaved my legs and all my nooks and crannies.

sissy phone sex tranny dommeShe also cleaned my house, made me lunch, cleaned up the dog crap in the yard… I was in heaven.  Why did I not get a sissy sooner? I played with her on that first day to try her out. Tested her cocksucking skills, rim job ability, and of course had to see what kind of ass pounding she  could handle. She struggled with my cock, it is pretty big, but she understands she is here to do whatever I need. She understands my needs vary from being a sissy maid to a sissy sex slave.

Every day she services me in some capacity. From cooking me dinner, to wiping my ass and everything in between . Her ass still needs some working on. It’s so tight. But daily fucking  and dildo play will loosen that backdoor pussy right up. The best part was now I have a live in pretty toy to take care of my sexual needs. If I want my ass licked, or my balls drained, or I need a tight fuck hole, I have one at my immediate disposal.  My house stays clean, and my cock drained. And, I have the gift of laughter right in front of me too. A sissy is the best gift ever. 

sissy training phone sex shemale