Category: Rim Jobs Phone Sex

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. 

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New Year’s Eve Fun with Cock, Cum and Virgin Cunt

Most folks are out partying for New Year’s Eve, but I am at home with my BFF’s teen daughter. And of course some cock. You see my friend wants her daughter to be a breeding whore. More specifically, a black breeding whore. Now, Alex is a virgin. A tiny little thing too. Poor babe has never even sucked a cock before. I thought about inviting my big black posse over, but with a tight teen virgin, I might scare her away from black cock if she pops her cherry to a 13 inch tree trunk thick cock. So, I thought a nice fat 8 inch cock was perfect for her extra tight cunnie.

We started earlier with cocksucking lessons. I showed her how to give an awesome blowjob. I was right there beside her giving her the hands on approach to cocksucking. Our model test subject was in heaven. A sexy MILF and a hot virgin teen worshiping his cock and balls. He is having the best New Year’s Eve ever. I showed Alex how to slowly work the shaft completely in her mouth, showed her how to swallow balls, and taught her all about the taint and massage the prostate to make a guy completely drain his balls. I was so proud when he shot a huge load of cum down her throat. It was so hot watching his cock pop off down her throat.  Her first load of jizz!  A very festive explosion for the end of the year. Her second load would be in her virgin cunt, but we are waiting till midnight for that celebration.

In the mean time, I am eating her young bald pussy. I want to see if virgin cunt taste different than well fucked pussy. So after she gets her cherry popped in a few hours, I am going to lick up her sweet cherry pie. For me, I am ringing in the new year with three of my favorite things: cock, cum and cunt. And instead of popping champagne, I am helping to pop virgin pussy. Before long, Alex is going to be a big black cock loving whore like me.

Black Cock for a Shy Ass

When we first met I hadn’t revealed to him that I have a chocolate bar in my panties rather than the fat pussy he assumed was there. I just had the feeling that he would never be comfortable with who i really am so I just enjoyed the time that we spent with each other. He told me men would hit on him all the time and that it scared the hell out of him. I would always assure him that cock isn’t so scary but he was convinced that it just wasn’t for him. It took me a while to convince myself that I should stick around someone like him, someone who was so afraid to explore.

I was at his house showering while he was out with his boys. He came home a little early and surprised me in the bathroom. As soon as he pulled back the shower curtains he saw me stroking my big black cock and he couldn’t stop looking at me. His eyes were fixated on my cock and he looked as if it might be something he could try rather than run from. Maybe this whole time he knew exactly what I had in my panties but he was afraid to ask me? I looked down and noticed he was hard as a rock. I came straight for him, stepping out the shower dripping wet and pressed my body on his, our cocks rubbing on each other.

He grabbed my cock and began where I left off, stroking the tip of my dick making me want him more than he wanted me! I pulled down his sweat pants and grabbed his ass, I felt him push himself closer to me so I could get a better grip on his bubble ass. He had a hand on my cock and the other was gripping my tit, I hand one hand holding his ass and the other was playing with his asshole. He loved it! He was groaning and grinding his ass back on me. I turned him around and began eating his ass right where he stood. I got his ass nice and wet for my big black cock and slowly I began to inch it into his tight virgin ass. He was pushing back into me wanting more and more. The excitement of finally being able to get into him is what made me cum so hard, and he took it all holding his ass open for me. I made a tranny freak overnight and it was a wonderful thing.

Anal Phone Sex Whore Cassandra: Take My Ass, Please

Ever since my Daddy first violated my tiny little ass when I was just a young school girl, I have been an anal loving whore.  He would crawl in bed with me every night and put his daddy dick in my pooper as he called it way back then. My back door was fucked long before my pussy. I was daddy’s subby bitch, now I am any man’s subby whore. I picked up a guy last night. Not my normal bad boy type either. More like the boring banker type. Cute though. And when we were dancing, I could feel how hard he was and it was big. I just kept thinking how good it was going to feel in my tight ass. He didn’t really strike me as the one night stand kind of guy, but I wanted his dick to fuck my backdoor something bad.

After I made him do a few shots to loosen him up, I asked him if he liked anal sex. He blushed and said he had never tried it. He admitted that he thought it was distasteful to women. I asked him if he had ever even given or received a rim job? No to both again. I grabbed his cock through his jeans, leaned into him and said, “I want you to fuck my ass.” He looked dumbfounded at first but I told him the only thing distasteful was not honoring a hot chick’s wishes. I got him more shots and once he was good and drunk, I took him home.

I got a bit forceful with him. Pushed him against the wall of my entry way and pulled his huge hard cock out. Fell to my knees like a good whore and sucked him until I was gagging and my eyes were bugging out. I then pushed him to the floor and got on top of him reverse cowgirl. I just spit on his cock to lube it up. Grabbed the base of his thick rod and worked it in my tight ass. I let out such a loud moan too. What a feeling. Brought back so many hot memories of when my Daddy fucked my ass. I was his first ass. My ass will spoil guys though! I can take it long, thick and hard up my ass. No hesitation; no wincing; no complaining; no pleading to stop.

He rammed his cock in and out of my ass for hours. We never even made it to my bed. That’s okay, I’m not exactly the bedroom type. I’m the down and dirty whore who picks up strangers and let’s them ass bang her for hours on a cold floor. Who are we kidding, I am the woman of YOUR dreams.

BBW Phone Sex with Glenda: Cum on My Tits

I hate winter. I don’t like being cold. I know I am not a skinny bitch, but I still would much rather be prancing around half naked, flaunting my curves than wearing extra layers that hide my big tits and round ass. Despite being in a big bulky sweatshirt and a ski jacket, this guy at the mall and his friend asked me if I wanted to have some fun later. They were having a party at their apartment. I was like sure, why not. I like to party, they were cute and I had no plans. I arrived in something much cuter than they had seen me in earlier. Turns out it was going to be a party of three. I figured why not, they looked normal enough.

After a few drinks and a couple hits, they whipped their cocks out for me. Pretty nice cocks too. Thick, juicy and hard as rocks. I took turns sucking them, but eventually they both ended up crammed in my mouth together. Two cocks are always better than one. I worshiped their dicks like they were my last meal. I wanted to make them cum on my tits. I love licking cum off my own titties. When you got boobs as big as mine, you can easily do that.

We titty fucked for awhile in between cock sucking. I got that cum on my tits I wanted. But I wanted to fuck too. They took turns eating my ass and pussy while their cocks recuperated. Then I got down on all fours and let them double penetrate me. Took one up my luscious ass, another in my plump pussy. When you are getting fucked by two dudes at the same time, your big ass titties swing everywhere. I got a good pounding. My pussy and ass are still a bit sore, but it was worth it. Most Friday night fun I have had in awhile. Hopefully I can party with them again soon. Good weed, two cocks, lots of cum, double stuffed. Yeah I hope we do it again real soon.

If you like chubby girls like me with nice big tits, check out my fellow sexy BBWs at our new site BBWPhoneSexFreaks. Fat is where it’s at.

Fall Is Time For Hunting

The leaves are changing colors and dropping from the trees. Animals are foraging for food and preparing to hunker down for the winter. Hunters are dressed in camouflage with their manly guns, hunting for meat like cave men.
It is a very primitive time of year. And very erotic in a way.
Some friends of mine that enjoy the sport of hunting invited me on a hunting trip last week. Laughing hysterically I told them I don’t know how to shoot a gun nor could I ever kill a living creature.
They told me not to worry I could sit at the hunting cabin, enjoy the peace and quiet of the woods, as long as I made sure they had dinner when they got home from the hunt.
After thinking about it I agreed, and I am glad I did!
I spent my days reading, listening to the radio and sitting out side in the open jerking my cock that seemed to stay hard more then normal out there in nature.
It was fun making sure the manly men were fed and taken care of in the evenings. And I liked sitting around the fire with them listening to the stories of the day and drinking beer.
On the very last day of our trip, one of them came in early and there I was, eyes closed sitting outside, cock in hand beating my meat hard and fast.
I felt someone looking at me but I was to far gone to stop, look or care.
When I finally blew my load and opened my eyes there he was with his dick in his hand.
He came to me and told me that he had never had the guts to approach me and that inviting me was his idea. He knew this was his last chance to come to me and tell me what he had always wanted.
I took him by the hand and led him inside. By the cabin fire I kissed him gently working my way down to his throbbing cock. Taking it into my mouth and working my magic, my dick got hard again as his body responded.
I sat back and asked him what he wanted to experience. I told him not to speak it to just lead me and I would follow.
Tentatively he put his mouth on my dick. I knew he had never sucked a dick before. But he mimicked what I did to him and he was fabulous.
He looked at me and asked if it would be OK if he stopped before I came. He wanted to feel me inside him and he wanted to be inside me.
I was delighted and took him gently, licking his tight virgin ass before stroking him as I eased in. He responded by rocking back against me and moaning. His desire brought me to orgasm quickly and before I knew it he was inside me fucking me with all the passion he had pent up.
He came deep inside me and kissed me hard, thanking me.
We laid on the blanket in each others arms for a while before cleaning each other up and cooking dinner together.
I guess my hunter bagged a deer on this trip. Just not a four legged one, a three legged one.

The Scent of a Woman

Normally my preferred choice for a bedroom companion is tall, dark and hung like a horse. But every now and then I enjoy some Sapphic love. There is something so sensual and sexy about fucking another woman, especially if that woman is a mature beauty like Rose. When I saw her at my spa last week, I got weak in the legs and moist between them. Rose is a far cry from a well hung black stud, but I wanted her nonetheless. I struck up a conversation with her, friended her on Facebook and worked up the courage to admit my girl crush.

Turns out Rose found me equally as lovely. She prefers young cock of the family kind if you know what I mean; but she was drawn to my body as I was hers. Two women in their sexual prime with rock hard bodies, what is not to love, right? I invited her over for brunch. I really did have intentions of feeding her more than my pussy, but from the moment she walked in I could think of nothing else but her body and how good it would feel to touch and taste.

Rose has a body better than any 20 year old. I kissed her as soon as she took off her coat. She was at my place for only one reason. The only thing she had on under her coat was a pretty pink corset, black thigh highs and black pumps. I couldn’t help but draw her in for a long, deep passionate kiss. My cunt was so wet just from feeling her tongue in my mouth. I slipped a finger into her pussy and she did the same to me. Finger fucking is a lost art form, but not for Rose. She finger banged me until I creamed all over her fingers. I hated to feel her fingers slide out of my cunt, but when she put one finger in her mouth to taste and the other in my mouth, I fell to my knees to worship her perfect pussy.

She came hard on my face. Her scent and taste were better than a 50 year old bottle of wine. I got on all fours for Rose. I felt her hands caressing my ass, her tongue rimming my asshole, her finger rubbing my clit. Didn’t take long to cum again all over her face. I returned the favor again by laying her down on my bed and licking her from head to toe. I used my favorite dildo on her tight snatch. I devoured every inch of her delectable flesh. The scent of a woman, the scent of Rose made me consider full on lesbianism. But, as good as she made me feel, as hot as her body was, I cannot give up big black dick; just like she can’t give up those young cocks.

Rose and I spent the entire day in bed. Worked up a great appetite for more than just each other. I love the way a black man owns me and fucks me so savagely, but not going to lie, the sensuality and softness of a woman, especially a mature beauty like Rose, is a welcum treat every now and again. Perhaps you would like to watch us, maybe even join us? Two mature gorgeous sluts could teach you a few things and drain your cock better than a bevy of coeds.

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.

Ass Worshiping Phone Sex with Vinny: Kiss My Ass

Do you appreciate a fine ass? Look at mine. I am quite proud of my derriere.  I am closer to 50 than 40, and my ass is so tight you could bounce a quarter off of it. Its ample, shaped nicely, tight and  loves to be worshiped. In fact, I have a few ass slaves. What you are thinking is correct. I have men and a few boys, and even a couple gals, who fall to their knees and worship my fine booty.  You see, I am a slave to big black cock, but that is the only time I am submissive. I am a rather sensual domme away from those black cocks. One of my favorite things to do with my admirers is make them worship my ass. I know my ass smells like roses,  and taste just as good. So, I enjoy making a subject bury his or her face in my ass and begin with a rim job. Nothing says I control you, like a loyal subject putting their greedy little tongue up your asshole and licking your taint, and getting off doing it.

After my ass is properly licked, I smother a subject with my ass. I sit on their face sometimes for hours making them smell nothing but my fine ass. If they prove themselves good ass worshipers, I will let them lick and finger my tight cunt. Some prove to be really good pussy lickers too. And a mature woman can never have too many ass and pussy worshipers at her disposal. I fuck a lot, daily usually, but there is still something about having your  wholes licked and worshiped. So I always make time daily for someone to come over and literally kiss my ass. Are you ready to submit yourself to me? Worship me? Clean me? Pleasure me? Cum bury yourself in my ass and pussy.

Boob Struck

I was standing in line at the theater the other night, there were so many people pushing bumping into each other, in front of me was a nice looking man very dark and handsome, the little tyke behind me got shoved into me and I flew forward right into this man, he smiled and said are you alright? I smiled and said yes, going to the movies is a dangerous affair. He said my name was Scott, maybe you should sit with me? I said great this is a scary flick my best friend Steph couldn’t come tonight so I’m here by myself, I would love to sit with you as long as I can buy the popcorn and soda, Scott said fine I’m buying the tickets and I just smiled. We found a great place to sit and started talking softly, as we were talking he reached down and took my hand and gently kissed me, I felt like I was in heaven he would reach over to get popcorn he would rub his hands against my beautiful big breasts, which made my nipples so hard, mmm.
The movie was so scary, I jumped, hid my face and screamed, Scott just laughed. After the movie, we went and got some coffee and walked through the park in the moonlight, it was so pretty out I said, Scott replied from my view point it’s beautiful, we walked to my house and I moved closer to Scott and whispered in his ear, I want you to fuck me now, he unlocked the door we quickly went into the house and I took him by the hand straight to my room, removed his clothes and mine as soon as he saw my tits he said he was in heaven, I pushed him down on the bed kissing him sucking his nipples, I had him get on his hands and knees as I licked his ass, rimming his asshole sticking my tongue deep into him, exploring his tight hole, then I took his balls and put them both in my mouth sucking and playing with them as he moans, he gets up and kisses me, sucking my big tits loving them totally, into them, we 69 and I lick his cock suck the head and take his cock deep into my throat feeling him sucking and licking my wet, tight pussy, his cock gets rock hard and he’s ready to cum I take his cock between my breasts so he could see it all and titty fuck him, he exploded all over my tits and face, he goes back down and tongue fucked me until I squirted all on him. we got up and took a shower together, and fucked again…afterwards we made a date for another movie night together. including a night of fucking.