Tag: Anal Phone Sex

Taking the Train

I love taking the train to town! So many horny men just leering and staring at me! It really turns me on! I always find one LUCKY man to give a hand job too! There is something super fantastic about sitting next to a handsome guy and seeing his cock JUMP to attention for me!  I just smile. Then I lay his coat over his lap and start rubbing that hard cock RIGHT there in the middle of the train! So many people standing EVERYWHERE as I jerk him off. Of course he tries not to show how much he LOVES it! His hard cock throbbing for me! Leaking for me! Until I feel him EXPLODE! And all the warm creamy cum cover the front of his pants! Mmmmm It just gets my motor running! Then I always invite them to my place later for a good fuck! Today was Matt… we are meeting later tonight. I hope he like surprises! I have a big black throbbing one for him!

Cum Whores!

Who knew the Train could be such a good place to pick up guys. I met Matt earlier. He is in for such a surprise tonight! I invited him over for a good fucking! Of course he doesn’t know about my big black cock! He arrived right on time! His cock already hard and throbbing as he walked in the door! I pulled him straight back to the bedroom! He let me strip him completely down. I even dropped to my knees and sucked his cock till his balls were nice and tight for me! Then it was time for the reveal! I stood up and started taking off all my clothes! He was so fucking turned on his body was shaking! When he unleashed my big black cock his face went so white! I could tell he wanted to bolt so I grabbed him and pushed him down. I didn’t give him time to think about it. I just shoved my cock right down his throat. After a few seconds he started sucking like a whore! Swallowing my thick cock like I wanted! By the end of the night he was BEGGING me to fuck him! And I of course I did! So tight and warm! He took all of me and came so good. I love turning men into my cum whores!

How a Cougar Shovels Snow

Mother nature is fucking crazy this year. Woke up yesterday to several inches of snow before December. I don’t do manual labor unless fucking big black cock counts as labor! So, needless to say, I don’t shovel snow. But , my car was buried and there was no pee path for my pups. What does a hot cougar do when she needs snow shoveled? She calls her hot stepson. Before I even made my coffee, there were 4 hot college studs and my stepson at my door shoveling snow. I was getting hot and bothered watching them in my yard doing all that labor. I jokingly yelled out the window, “Give me a show.” Suddenly, they started taking their clothes off. In 20 degree weather, these college studs shoveled my snow naked. Now that was a show.

I invited them in to warm up, well warm me up. I sucked their hard cocks. How they stayed hard in that chill was beyond me. My stepson said it was my hot body they kept them warm. I thanked each one with my hands, mouth and boobs. Made sure each one gave me a hot creamy load of cum. My stepson did the most work, so he got to fuck me first. I was riding him reverse cowgirl in front of his friends. Even though I had just made them all cum, they were hard again watching my show. They stood their stroking their cocks for me as my stepson pumped his dick in and out of my ass and cunt. I was so turned on by all the hard throbbing dick around me, I squirted. Full on jet stream. I hit the boys with my juice.

Well squirting on my college studs turned my afternoon into a gang bang. I ended up fucking all four of my stepson’s  fraternity pals. They covered me in cum, I covered them in cum.  Hot jizz is better than a hot toddy on a snowy day anytime.

A Good Mommy Never Says No

Recently my son’s boss told him he was up for promotion, but there was a string attached; I was that string. His boss wanted me, well wanted my ass. Guess my son brags about his hot mommy and his boss is married to some ugly dominate bitch who doesn’t give up the ass. I knew I could not say no. I cannot deny my son anything. Pointless to even try because he will just force me if I even utter the word no. The deal was I had to put on something extra slutty and meet his boss for drinks at the country club first. He wined and dined me first. Did he not know my ass was a sure thing?

After boring chit chat, lunch and a few drinks, we went back to a hotel he had rented for us. When I walked in, he had the room prepared. There was a plate of coke on the table for me. He had a wide assortment of dildos and ass toys, plus all sorts of lube. In addition he had big fluffy pillows. I assumed to put under me while he fucked me up the ass. He had no idea how much I could take up my ass. I’ve been getting ass pounded for decades. But I indulged him, let him think I was not a total anal whore.

He was ugly and in not so good of shape. I did a shit load of coke to prepare myself to get fucked by this fat bastard. I didn’t mind duping him a little, playing more innocent than I was, but turns out he was the one playing me. He tied me to the bed, blindfolded me, then opened the adjoining door. I heard a lot of voices. Turns out my son’s boss decided that all his friends, who had never successfully fucked a girl up the ass, could have my ass too. Glad I was fucking high. All these sweaty ass fat men were fucking my ass. Sure they used lube and pillows and I was high, but I could feel their fat, hairy, sweaty bodies mounting me like dogs in heat. I just took my mind somewhere else. Thought of young buff black guys anally gang banging me instead of a bunch of middle aged fat fucks.

These guys went wild too. A taste of the ass hooked them, got them addicted. They did a train on my ass that lasted all night. Sometimes they even double penetrated my ass. Thirty three ugly executives with unfulfilling sex lives fucked my ass and used me as a cum dumpster. Best piece of ass any of them ever had or will ever have again. I am way out of their league. But my son’s promotion was on the line, so I just remained quiet and took all their sweaty cocks up my ass all night long. A good mommy does whatever she needs to do to help her offspring, no matter what their age.  Thank goodness for cocaine. Makes the more unpleasant things we do more bearable. Can I be a good mommy for you?

T-Girl’s First Time: Popping the Cherry on That Back Door Pussy

Every girl remembers the first time she lost her virginity. Even though I am not a traditional girl, I am no different. I was nervous too. Girls are worried about making a mess when they pop their cherry. No girl wants a guy to see all the blood that usually accompanies the first time, nor does she want to endure the pain that is rumored to come with losing one’s virginity. My traditional girlfriends talked about doing things to prep themselves for their first time. So when I was ready to pop my cherry, I tweaked some of the advice my girlfriends gave me to fit my unique situation.

I bought a big dildo and began using it on my ass so it would not be quite as tight. Every day for weeks I fucked my ass for hours with my special toy. I was afraid of shitting myself  when the guy I was seeing popped my cherry. I read about enemas, found a video online, and decided to make my own coffee bean enema. I was too embarrassed to go into a drugstore and buy a pre-made one.

The day before I planned on letting Ryan fuck me, I gave myself a homemade enema so my ass was cleaned out and I would have no embarrassing accidents to ruin the moment. I pretty much just drank water until I met him. After our date, I told him I was ready. He was not prepared. I had been stalling him for months. I told him I wanted him bareback in me. I mean, he didn’t know I could not get pregnant. We had to do it in his parents SUV in the back seat as we had no private place to go.

I was nervous for lots of reasons. Would it hurt? Would I make a mess? Would he realize I was not 100% female. I was in school still and only a few teachers and friends knew my secret. I fit in as a girl. Anything else I was a freak and I desperately wanted to fit in, but I could not avoid the first time forever. I had him take me from behind to hide my cock. It was dark. I had inserted all sorts of lube to make my ass feel like a wet pussy. It was his first time too so I figured he would have no baseline to judge.

It worked. He slid his hard cock in my back door pussy for the first time, popping my cherry. It felt so good. Better than I could have imagined. I don’t know if it was because I prepared myself for the first time, or that I was just meant to have cock in my pretty back door pussy, but I started fucking all the time. Soon my secret was out. But so many guys had fucked me and they didn’t want folks to know they had been with a T-girl so they kept their mouths shut. Now I don’t hide who I am. I am proud of my duality.  Proud of my big throbbing cock.

Happy Veterans Day: 21 Cum Salute Tranny Style

Happy Veteran’s Day vets! Too all the soldiers who have so bravely served this country, I give you a BIG 10 inch salute.

I have nothing but respect for the men and women who have served our country. In fact, I was in my local Veteran’s Day parade today. I wore a hot patriotic bikini and made vets smile. I like making soldiers feel great.  I have gone over seas on USO tours with regular hot women and soldiers have never known the difference, well until they get me naked that is. Today, on that float was no different. When the parade concluded, there were several vets waiting to meet me.

One in particular, was a WWII and Korean War vet. Needless to say he was a dirty old bird. I like dirty old birds. He told me I was the most beautiful woman he had ever seen and I reminded him of a 50s pinup. Said I was a classic beauty. I let him take me to lunch. He could no longer drive, but he seemed financially well off, had a limo. We got in the back of the limo and he offered me a lot of money to spend the night with him. Said it had been too long since he enjoyed the company of a lovely woman. I was smitten. He was 3 times my age, but such a gentleman. I wondered though if a special girl like me would give him a heart attack. I was struggling with telling him, when he saved me the awkwardness by admitting he knew my secret. How I asked? He said he just knew. When he was in Korea, he frequented a brothel that specialized in Asian lady boys. So my dirty old bird was a freak. I was in love!

I went back to his house and gave him a show worthy of a veteran of his stature and experience. I started with a sexy striptease. I can work a pole, hehe, both kinds of poles! I ended with a sexy lap dance. I could feel a lot of life in that old cock of his. My senior citizen needed no Viagra. I pulled t out of his pants and gave him a Happy Veterans Day blowjob to die for. He called me his sexy little Hoover. He came so hard in my mouth. He wanted to kiss me afterwards too. I love a man not afraid to taste his own cum. I wasn’t sure he could cum again so quick, but I was wrong. He was hard again in no time flat. I told him I thought it would be hot to fuck him in his dress blues with all his medals on it. He agreed too. I mean it is an appropriate tribute. I bent over, spread my cheeks and let an 86 year old decorated General of the US Army fuck my ass. Age is just a number. That old fox fucked me like he was a 25 year old Marine.

We fucked for hours. I gave him a creamy tribute all over his face and in his ass numerous times. A sort of 21 cum salute. I can’t wait to spread the honor today. Soldiers deserve my respect, my cock, my cum!

Use My Ass to Keep You Warm

A few years ago, I went to visit my oldest son at Harvard during winter. I was in this little bookstore with him when a blizzard of epic proportions hit. We had to wait it out as it was a complete white out outside with dangerously cold temps. Well a few hours in a bookstore, turned into a few days. Small town, so the blizzard incapacitated the whole town.  The snow did not stop and drifts covered the door so we were physically trapped. We had some food in the bookstore  and a bathroom thanks to the employees. But after 4 hours of being trapped, we lost power. It was my son, myself and two other boys working the store.  We had to stay warm. We had to entertain ourselves. Not that I am not a literate whore. I’m actually very well educated and schooled in literature. But, being the smart cookie I am, when presented with cock or books to pass the time in a cold store, I’ll pick cock every time; especially young cock.

I had three well hung college age studs all to myself. It was purely bonus that we lost power. We had to fuck to stay warm. We had to fuck to stay alive. Turns out a few days of being trapped makes guys more aggressive, a bit cagey so to speak. After the second day, the sex got rough. They no longer cared what I wanted. They forced me on the cold floor and fucked  all my holes at the same time. I had a cock in my mouth, my cunt and my ass. My son could be aggressive, but it was the other two that egged him on to obliterate my ass, use it for heat. My son forced my face down on the floor, which rose my ass up and the other two shoved both hands in my cunt and ass. Stretched me way the fuck out.  No lube, no warning; just  started double penetrating my holes. Eventually my son joined in on the torture. They sodomized me with their fists for what seemed like forever. They used my ass and my cunt to keep their hands warm in the freezing temps.  All three of them inserted their cold hands and arms up my ass. I never knew you could go so deep in a person’s ass or cunt until that day. To keep me warm, they came all over me every couple of hours.

Finally we were rescued. My ass has never been the same since. My ass was stretched out further than it ever had been before, or ever has been since. I became an anal queen during that time trapped in the Harvard Bookstore. I secretly loved how they distorted my ass; the pain I felt being triple penetrated by fists. Every anal experience now, I hope to create that same sensation. What would you put in my ass or how would you fuck my ass to stretch it out further than it’s ever been stretched before?

Anal Phone Sex With Betty

I can’ get enough of anal pleasure.

I believe everyone should try it, whether you are forced or willing to try it.

I love everything there is about getting fucked in my beautiful ass.

Since its the Holiday season, which by the way is my favorite time of year! I must tell you about my first time Having Anal!

It was thanksgiving day and I went to my roommates family thanksgiving where I met her really sexy uncle. 

He was a beast. so sexy! Tattoos, big arms and ugh he smelled so amazing! Just hugging him my pussy got wet. He smelled that good! All women love it when their guys smell good! Any way lucky for me he was going through a divorce. And he looked like he needed some. I being cocky and almost an adult felt like it was my gift to him to give him some pussy. 

 

I asked him to help me set up my room, which was the office and had a pull out couch and a bathroom off to the right. I was excited, He walked in after me he had blankets, pillows and a sheet for the bed. He he set them down and turned around I had my pants off. 

I asked him how long it would take him to get off and he just smiled at me. He bent me over the arm of the chair and slid his cock into my dripping wet pussy, He spit of my ass and slid a finger up there. He was going to town on my pussy. 

He was so big and so strong I came in just a few minutes, He stopped and was so sweaty.. He kissed my neck and as he pulled out his finger I felt him push the head of his big cock into my ass. The pain of his cock being in my ass was so harsh , but the feeling of his cock packed into my tight virgin ass was so marvelous. I laid there trying to relax my body for him to bury his cock into me, I started to caress my clit… that orgasm  was overwhelming!! 

 

 

 

Tranny Phone Sex with Carla: I Love Bi-Curious Virgins

I picked up a guy at the club I went to last night. I sometimes frequent this little bisexual S and M club. I have a bit of a latex fetish. Combine that with my dominate bitch side, and this place is a treasure trove of subby boys wanting to service a hot special bitch like myself. I strutted into the club like I owned it.  Hot pink latex thigh highs. Metallic blue itty bitty latex dress. Black ass kicking latex boots. And the best part, my latex whip. I commanded the place the moment I walked in and had my pick of the litter. All sorts of subby boys buying me drinks, lavishing me with their attentions.

I picked this one guy because he was a newbie. Said he was bi-curious, but outside of his head, had never been with a man before, let alone a shemale. I like popping back door cherries and helping men discover their bisexual side. I brought him home with me. Gave him a lesson in cock sucking and rim jobs 101. He did quite well for his first time. Manage to take all 10 hard inches down his throat. Of course he gagged, but he did make me cum. I gave him his first load in his mouth and first load in his ass.

His ass was sooooooo tight. I love virgins. I used some KY warming jelly, went slow at first to get past the wall, then once I was in, I started thrusting hard and steady. My big cum filled balls left a mark on his ass. I always cum quicker with a tight virginal ass. Bi-curious virgins are the best. Tight, always eager to learn, and usually submissive.  Are you bi curious? I bet I could have some fun with your back door pussy. Never say never is my motto. You don’t know what you are missing. Trust me, you will cum harder and better with me in your ass then you ever did with your cock in your wife’s pussy. It can be our secret. I promise. Let me be your first cock.

Incest Phone Sex with Vinny: My Son’s Monster Cock

When I was much younger, not even out of school, I got pregnant. My folks forced me to give my son up for adoption despite the fact that I wanted to raise him. Thirty years later, thanks to the Internet, my son found me. He wanted to meet his birth mother. I was so nervous and excited too. We agreed to meet some place neutral. I couldn’t believe my eyes when I saw him. Big, tall, handsome young man. We had an instant connection. An instant taboo attraction. He felt it too.

We decided to get a hotel room so we could have more privacy to get acquainted. But as soon as we entered that room, we could no longer contain our desire, our natural attraction. I knew he was my son biologically, but he felt more like a lover. We kissed while sitting on the bed and sparks ignited. Next thing we were rolling around on the bed passionately kissing, tearing each other’s clothes off. I could feel how big his cock was and I was impressed. When I unzipped his pants, I got a wonderful, beautiful surprise.

My son, a white boy, had at least a foot long very thick cock. I was salivating for it. My cunt was dripping with anticipation of my son’s thick huge monster cock in my pussy for the first time. First, I had to devour his shaft. I have sucked a lot of huge dong in my life, but this was not only a big cock, but a very special one. I was nervous as I worked the big purple head into my mouth.  After a few minutes, my nerves went away. It felt natural to have my son’s cock in my mouth. He even called me Mommy as I was giving him the best head of his life. His balls were huge, full of cum for me. Veins popping out on his shaft like  it was Frankenstein’s cock. He was close to cumming, but he wanted to explode his spunk inside his mommy’s pussy, inside her womb where he came from.

I hopped right on his dick. I couldn’t believe I was about to fuck my son. But, it felt right, felt natural. And when his big dick started pumping in and out of my pussy, it felt like heaven. What an amazing fuck my son  turned out to be. He shot the biggest load of sperm I have ever had in me too. I kept dipping my fingers in my cunt to scoop some out to taste it. Yummy boy batter. After we fucked for hours, we just laid there, in each other’s arms, talking. We agreed, this was taboo, but right. I have a date with my son this weekend. I can’t wait to feel his cock in my pussy again. Can’t wait for him to take my ass.