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My Shemale

By: 1zapatoapestoso



I was a young buck about 23 yrs. old and was touring South America. My friend and I were out and about the city of Rio de Janiero, Brazil.

We had been drinking all afternoon long and were feeling pretty happy when the evening rolled in. We were hoping to find some local girls to have some fun. 

When this lovely lady approached us and started talking. My friend being the more outgoing one started to haggle on a price. It seems that this lovely lady had decided that she was willing to have some fun, with the both of us, for the set price. 

She led us to a hotel room where I found out that we would have our fun but only one at a time. I had never had sloppy seconds so I figured it would be one for the books. 

She paid for the room and led my friend into the room for his share of the fun. I sat on this concrete ledge and waited excitedly but patiently for my turn. 

Many naughty thoughts crossed my mind. Stuff like how would that pussy feel with someone else cum in it. Would I eat that pussy, did she like anal or what would I do. These were just some of the thoughts that I can remember. 

Sometime past and then the door opened. My friend came out but was a bit silent for his normal self. I was ready so didn't give it much attention. 

Inside the room was a chair with stir ups. 

I went in and she started kissing my neck and shoulders while she took off my clothes. 

She was still dressed in her dress which seemed odd but that didn't register till later. Once I was totally nude she pushed me down on the chair and placed my legs on the stir ups. 

She then started to give me a blowjob; it was fantastic to say the least. In the process of blowing me she started to insert a finger up my ass and asked if I liked it. It felt good so I went with it. 

After a sucking me off a bit longer she started fucking my ass with her finger and then added another finger. She kept wiggling her fingers as she sucked on my cock while swirling her tongue all around it. After a bit more sucking on my cock and fingering my ass she stopped and asked me if I liked getting my ass fucked by her. I told her it felt very good. 

She then said good and dropped her dress. Wow was the only thing I could say as there stood a bronze beauty with gorgeous c cup breasts and behold her, she had a cock. It was about seven inches while hard and about 2 inches round. 

She walked to me and started to place her cock toward my asshole. I stopped her and told her on the bed. She sat on the bed and I asked her if her cock was real. She didn't answer but instead she put her hand on the back of my head and leaned back. This caused my head to go straight for her cock. 

I opened my mouth and she pushed it all into my mouth. I tried doing the same for her and she directed me on how to do it. No teeth she said, suck it in and out while moving my tongue all over the head. I did it for a while till she stopped me and said lets fuck. 

I told her to lie down and I squatted over her dick. I grabbed her tits while slowly taking her cock into my ass. It felt good feeling it spread my asshole. I loved how she was taking my anal virginity. It was the right size of cock for my virgin ass that it was sliding in nice and slow.

She would slowly shove about an inch at a time while I squeezed her tits. She keep asking me in Portuguese if I liked it and I kept saying yes. Further and further in her cock invaded my ass, it felt so deliciously wicked getting fucked up my ass while playing with her tits. I had about 5 inches in me or so it felt when she gently pulled out and slammed the rest of her cock up my ass.

It totally blew my mind. Even though I had her tits in my hands, her hands on my hips and nothing touching my cock. i started Cumming like crazy, I was even moaning like the bitch in heat that I was. 

I slumped forward with her cock in my ass, as my own cock twitched and spewed that last of my cum on her belly. After catching my breathe she pulled out of me and went to clean up. I cleaned up and got dressed. 

I had forgotten all about my friend, until I was outside. We both walked back in silence back to our place. I didn't ask him why he was so quiet but I was quiet only because I was enjoying the feeling of my freshly de virginized ass and the cock that it now missed being in it.

This is a true story and there are only 2 regrets that I have from it. One is that I didn't finish sucking her cock till it came and that I have never had the pleasure of meeting another special lady like my Brazilian bronze goddess that took my anal virginity and taught me the pleasure of having being fucked up the ass by a special girl.

My Shemale Husband



I pulled against the cuffs around my wrists; the leather had begun to work like sandpaper it did hurt me, not knowing that much worse was to come with an inspired finish. I lay face down on our bed, my face buried into a pillow. I tried to move my legs. If I could pull them together, perhaps I could ward off the strap-on about to be forced into my rectum. My feet were tied firmly to the bed posts. I was defenseless against the inevitable.

I had only one final hope. Still muffled by the pillow, I shouted, "mother."

It got no response. My female assailant began to thrust her large strap-on cock roughly into me. She slapped me with a paddle resoundingly across my ass. "Lift up your hips or this is going to hurt even worse." The impact burned my right cheek.

I couldn't help myself. I began to whimper, "mother . Please, I'm saying mother."

She didn't stop pushing into me, instead her hand had begun masturbating my cock. "This should help. Now lift up your fucking hips."

I was angry. I was being violated and humiliated, yet I had no other choice, I lifted my hips and felt her 12inch strap-on move to its full length inside me. This time I screamed, "mother, for fuck sake, mother. mother. mother." I was desperate to make her stop.

"I can't hear you, boy. If you want to act like a she-male, you have to expect to be treated like one."

"Please, you don't have to do this. Not like this." I couldn't help myself. I began to cry. I was sobbing and begging.

Then I started to cum, a strong one. I stopped my sniveling and began to gasp. Her fingers worked steadily on my 2 inch cock and I felt a shiver overtake me.

"I am a slut. I've fucked other men. I deserve this. Don't stop, Elisabeth."

"You worthless bitch. I knew you were sucking of your friend Frank. Take it." She grabbed my buttocks with both hands on either side and rammed with all of her weight against me. 

I could feel her slide deep into my rectum, which felt raw from the intrusion. When she pulled out I could feel traces of oil still flowing from her strap on dribbling on my crack.

"OK, you've gotten what you wanted. All of it. mother."

"Sorry, Willem, you still need to pay." I could hear her go out of the room and then return seconds later. A flash of bright light and I knew I was being photographed with the entry of my ass still wide open, another picture for her private collection, no doubt. Then came the strap across my back. It nearly took the wind out of me. Ten sharp whips with the narrow leather flails. Each was painful and was inflicted with enough force to leave a painful mark that would be visible for days.

It was then that our 20 year old twins walked into the bedroom, my daughter said oh mum you were great. We culd see everything on the TV as you had told us to watch. Seeing dads cock erupt when you used the flails made me really wet while my brothers cock nearly jumped out of his pants so hard he was. It was then that I understood why their had been such a big charge made on our creditcard by the Dick Smith TV and electronics business.

I was angry and fought to control my temper. Bad things happened when I couldn't. It was no use. I began to cum once more. My climax was obvious and I knew it would only lead to farther punishment. Another five stokes across my back for my insolence. Now is your chance my son was told, your sister and I would like to make a DVD of you fucking your dad. Only you strip first and make sure that you both yell, out your family relationship when you fill his ass. So we can sell copies of them to pay for my pleasure place. The twins looked at her with disbelieve, what pleasure place? She told them."I show you after."

Comforted by my daughter, before I was ordered to be on hands and knees, while our son Howard was pushing his cock in my anus. My daughter yelled out make sure that dads tiny cock is shown when Howard's large cock was pushed slowly in to my rectum. I felt my own cock come back to attention once more, when our daughter said how could you possibly get pregnant from that little prick. My son must have been enjoying himself taking his time slowly fucking me so his large cock became a dominant part of the DVD. After he had cum and his semen was dripping from my stretched anus the girls clapped. Probably for the benefit of the DVD, finaly I was untied. To be told to lick my sons cock clean. Me protesting that it had been in my ass and some shit would be on it. It was than that Elisabeth told me you better if you don't want to have your daughter use her riding crop on you when you give your son another blow-job, in our dungeon.

"Fuck it, Elisabeth. I said the safe word. If you aren't going to go by it, how can I trust you?" My face flushed with anger but I willed my voice to remain clam.

Elisabeth's face presented me with a black stare. "Don't be such a baby, Willem. You know you wouldn't enjoy it, if I wasn't pushing you past your limits." She kissed me as I sat up next to her.

"I was forced," I said. "You could have hurt me." I wanted her to understand that we had to draw a line somewhere.

"A wife can't force her own husband. Not in this state of Australia." I said. Her smile seemed cruel and condescending. 

"Maybe not legally, but being forced against my will, is still morally force."

She laughed, the woman actually laughed at me. "And you can't get off without it."

That was true, at least mostly. "mother" was our agreed safety word. A single word that was discernibly different for any sex talk we'd likely have. Elisabeth was supposed to stop without questioning whenever I said the safe word. or not? Elisabeth had wantonly dishonored our agreement for her own gratification. I was now at her mercy daily not just on our weekend sub/dom sex romps, me performing in front of our children or the life I had enjoyed would come to a sudden end. It was as if I was walking on a tight rope without a net.

At that moment, I silently vowed to take revenge and punish her for this violations of my trust. I'd always been an enthusiastic submissive in our relationship but she was becoming increasingly domineering and savage. I knew I had to take back some form of control before this got farther out of hand.

I'd always been the compliant participant in my relationship with Elisabeth. She was the first woman to recognize it in me. I'd had sexual encounters with other men before we met, but none ever satisfactory. I began to wonder if I might be frigid. Then Elisabeth, on our fourth date tied my arms behind my back took my pants down and forced me to eat her out in front of her friend and male partner it was our first sexual encounter. 

It sounded bizarre, since I knew nothing of the B&D scene, but that was the very first time I was able to cum. A revelation of the missing piece of my sexual needs. My sperm shot on the gras and my pants and as I helplessly licked, I had come with a blast, with a spermload I didn't believe I had in me. From then on, I was hers to do with as she pleased. I gave myself, body and soul, to her demanding tyranny.

I've been willingly and eagerly bound, whipped, and spanked many times. The domination was like a drug, exactly like a drug. The more I got, the more I wanted and the more it took to get me to the same level of arousal as the previous time.

It was august or late winter, I lay completely naked bound in a coffin, in a portion of the basement, which Elisabeth had converted into her dungeon for a more advanced dominance play sessions. The walls were painted black, a job I was told to do. Dozens of candles provided the only illumination in the room below ground-level. A ring had been mounted onto the brickwork to which I was securely chained many times for hours on end, otherwise the room remained unused. The flicker of the candles gave the room an eerily macabre yet romantic look.

Now the children were introduced to Elisabeth pleasure room, after leading us all into that place from the bedroom we just had vacated. She took one of the candles and held it over me. A single droplet of wax fell onto on one of my nipples. I winced at the hot touch of the paraffin. More drips landed on me and a splatter of small burning drops kissed my tender flesh. A red ring surrounded each drip as it landed. While the candle was held downwards so that the flame consumed the shaft more rapidly, a steady stream of red wax rained down upon me. I yelped as a cascade of molten liquid poured over my helpless torso. When one candle was finished, Elisabeth grabbed another and repeated the process.

The small silver rings that went through my pierced nipples became splattered with wax. Elisabeth pulled at each blue captive bead on the upper curve of each of the hoop. My aureola's became sensitive from the stimulation and I cried out with a familiar mix of pain and exhalation. 

The candles were different colors and slowly a rainbow of warm wax built across my chest and belly. I watched as my navel filled with a deep red candle paraffin and slowly cooled. The pain subsided when I became used to the melted liquid stings and a cover of hardened wax began to protect my sensitive skin.

When Elisabeth had only three candles left to light the dungeon, Elisabeth carefully pried the built up wax off me. A near perfect form of my upper body formed and she placed it on a shelf mounted on the wall. I hoped she'd fuck me now. I was melting from my own desires, but she had more plans for my suffering. Your tiny prick will be done by your daughter next time now she has seen how its done, I was told.

Elisabeth held a large round white candle, that she worked it into my rectum. It hurt going in since the bottom was flat with edges and I tried to move away. I knew such behavior might rate a slap across my thighs, but I couldn't help myself.

Eventually, the candle was inserted inside me to about three quarters of its length. My heart beat became faster when I realized what she had next in mind. I heard a match strike and smelled the scent of sulfur. She lit the wick and fire danced near my anus. 

"I'll blow out the flame...as soon as he cums," she announced.

"Please stop, this is getting dangerous."

"Oh, are you going to use your safe word to get out of this and prove what a scared little boy you are? Maybe your rather play with dolls than fuck." 

Elisabeth had ways of intimidating me into not using our safe word. I'd be shamed for days on end after I had. 

"Well, what are you waiting for? You'd better get started with a blow-job on our son, unless you want your ass scorched."

She placed Howard's cock near my mouth. I moved my head up to begin sucking it. She teased me by pulling it away. Then she laughed and ran it over my lips. Once again, I opened my mouth, only to have it moved out of my restrained grasp. I had to beg to suck the son of a bitch's penis. My rectum was beginning to feel the heat of the candle's flame. While either my daughter or my wife were filming the whole performans.

By the time he blew his load in my mouth and she had been assured I'd swallowed every drop, I could feel the flame starting to heat my anus. She blew it out with a single puff and I came in a blinding blast moaning in a high pitch girlish voice that said how much I loved the experience.

I was released from the board, only to be chained to the ring on the wall. Elisabeth intermittendly between her and our son fucked me with a strap-on cock, a rubber dildo and a thinner candle for two more hours. I could feel my anus tingle against the surgical steel ring held within and its piercing. I was always aware of its presence, originally inserted as constant reminder of my acceptance of my servitude, as my cock began to swell in anticipation; the ring added a devastating sensual stimulation.

I came and came again like the shameless she-male I am. By the time my arm and leg manacles had been unlocked, I was filthy from laying on a floor mat covering the bare concrete, but too satisfied to feel the mortification I should have. Next Howard took over with the camera so to clean me up, both mother and daughter pissed all over me while I was left, and locked in my wives dungeon while the three of them left me there in her locked pleasure room.