Loraine's Quest Ch. 03

I was miserable. The bent over position with my head forced back was causing cramps in my back, shoulders, neck, and thighs. My nipples were a constant source of acute pain that was intensified by my Mistresses occasional teasing with her foot. My cock and balls consumed a great deal of my attention. The rubber band behind my balls was the origin of an excruciating, burning pain that threatened to drive me insane.

If only there was some relief from the ever tightening elastic band. The elastic band of the condom encircling my genitals at the base of my cock and balls was another source of burning pain. It wasn't as agonizing as the pain from the rubber band behind my balls, but the two combined had me believing my manliness was being slowly pinched off by their unrelenting constriction.

To add to all this pain, the enormous butt plug that Mel shoved up my poor ass was making its presence known. My ass hole was stretched beyond belief and the pain was intolerable. My bowels felt as if they were stuffed with an expanding intruder that would eventually split me in half.

The inflated penis gag held my mouth open so wide that I thought my jaw would dislocate. The aching in my jaw led me to conclude that not even relief from this oral intruder could restore function to my poor jaw.

Every time James turned a corner a little fast, stopped quickly, or accelerated briskly my position shifted a little adding to my discomfort. The constant nasal moaning let my Mistress know that I had crossed over the line and was losing control of my ability to maintain any decorum.

Much to my amazement, my cock remained rock hard through all this. Mistress Catherine would check occasionally and let me know that she was pleased that I maintained my erection with all the painful distractions. Mistress checked my cock and balls once again and told me, "Loraine, your cock is still as hard as before. Your balls still look wonderful in their latex covered bondage. It is obvious to me, from your constant erection, that this form of cock bondage/punishment is enjoyable for you.

That makes me very happy. I did notice, however, that your balls feel a little cool from restricted blood flow, and want you to know that relief will come as soon as we are home."

I looked at the vision sitting in front of me. Her skirt had hiked up as she slid forward to check on me and her beautiful smooth, milky white thighs were exposed making her silk covered pussy more visible. A pussy that was only 10"-12" from my distorted face. She was such a wonderful Mistress; it was obvious she was concerned about my very painful bondage and wanted to have her TV back in drag as soon as possible.

"Loraine, we're almost home." Having said that, she scooted farther forward on the seat and started releasing the bindings on Leonardo and Venus. "Let's get you two loose now so we can speed up the process of getting Loraine upstairs to remove those elastics on her genitals--and remove her nipple clamps."

As she was leaning forward to release them her pussy was thrust forward, that wonderful feature of femininity was only inches from my nose. I could smell the wonderful musky odor from her crotch. I could see her silk panties, imagining that they were damp and that the sight of her property in bondage really excited her. If I could only close the gap and bury my nose in that restricted portion of her anatomy.

I could feel the blood pulsing in my cock from this additional stimulation adding to an already incomprehensible pain. Was it possible to get any more erect?

Leonardo and Venus were sitting back on their heels and stretching their muscles. Mistress Catherine moved to unlock their handcuffs, and as she did her dress fell over my head. There I was with my head under her dress, inches from paradise. I was breathing and moaning even louder now!

Mistress sat back as Leonardo and Venus released their legs from the leather strap securing them to the floor. Mistress looked at me and smiled, "Did you like getting that close to my pussy slut?"

I looked at her and tried to communicate my longing for her and my desire to rid my body of the many torments. She reached out with her toe and flicked my nipple clamps again. My eyes closed as the pain escalated once more. She smiled, "I thought so, you have done extremely well today and will be rewarded for your good behavior later."

My two sister slaves were now sitting next to my mistress. "I want the two of you to help Loraine to the elevator as soon as we're stopped in the garage. I'll have James gather the merchandise and put it in the elevator to help speed things up."

Mistress pulled the zipper at the back of Venus' head and pulled the yellow latex hood forward so it was resting on her chest. "You may remove your ball gag dear." Venus popped out the ball and immediately said, "Thank you Mistress." "You're welcome my lovely Venus." Mistress turned to Leonardo, "I know your discipline helmet was to stay on one more day, but I want to look at your lovely face again--take off the helmet and show Loraine how pretty you are."

Leonardo complied and I was looking at a beautiful woman with shoulder length blond hair. She had high cheek bones and soft pouting lips. Her beard stubble was apparent, as she had been in the helmet 6 days. I understood why she was always looking at mirrors.

"Venus, please get Loraine ready to go, we're almost there." Venus unhooked my pinioned elbows from the ceiling anchor along with the strap forcing my head back. I sat back on my heels and felt a little dizzy from the sudden change in position. Mistress looked at my engorged cock and tortured balls, reaching out to squeeze my balls.

She retrieved a latex genital whip from a side compartment and let fly with 10 strokes. "Hate to see a well bound set of balls go without a little extra 'treatment', Venus loosen her legs." I grimaced at the additional pain from the genital whip as Venus released the straps on my ankles and I relaxed a little.

I looked down at my poor tortured nipples and genitals. I was amazed at the amount of tit meat Cleo had managed to capture with the devilish clamps. The squashed flesh looked terrible. It was three colors, blue, red and white depending on the proximity to the jaws of the clamps. I prayed the increased pain when they were removed would be bearable.

I looked further and focused on my cock and balls. My balls were a tight spherical package under my cock. The rubber band had tried to return to its original size and the only thing stopping it was my ball sac. I couldn't believe how tightly restricted they were. They were blue in color and covered with the shiny latex of the condom. The pain was unbelievable. My cock was standing straight out and also turning blue. The elastic from the second condom was causing another painful burning sensation that was now almost equal to my poor tortured balls.

The car finally stopped and James opened the door. "Get the things from the trunk and put them in the elevator please." James quickly moved around the car to the trunk and started picking up the many parcels.

Venus and Leonardo helped me from the car. I could hardly walk due to the pain, the unusual jack boots and the huge plug in my ass. I walked with the help of my slave sisters, but could only take 8" steps due to the short hobbles.

I watched my tormented cock swing from side to side from my mincing steps as we walked to the elevator. I thought to myself how sensual a cock and balls looked bound as mine were. The pain was excruciating, but the visual sensation incredible.

I decided that in spite of the discomfort, this was to be a favorite cock "treatment" of mine. I smiled inwardly as I thanked Cleo and Mel for their "gift".

By the time we got to the elevator, Mistress had opened the door with her magnetic card and James had put the parcels in the elevator and disappeared.

On the way up Venus took my cock in her hand and massaged it gently while tracing her fingers over my bundled balls. Mistress watched and said, "Does her cock feel good Venus?" Looking embarrassed at being noticed she said, "Yes Mistress, it does. It's so hard and her balls are so cold!

Look what those mean slaves Mel and Cleo did to poor Loraine. May I make her feel better later?" We'll see Venus. Right now I want to get those devices off of her. But we have to be careful not to hurt her in the process." "Yes Mistress," responded Venus.

Leonardo was stroking my ass and said, "Mistress, I have never seen a plug this big, do you think her ass is OK?" "Yes Leonardo, ass holes can be stretched a long way."

The tender strokes from my sister slaves helped a little, but the pain was overpowering. I had to get relief and soon!

I was surprised that the gentle massage from Venus wasn't stirring me to think of orgasm. I guess it was due to the oppressive pain racking my body.

The elevator finally opened and Venus helped me walk to the ante room. Leonardo removed the parcels while Mistress locked the elevator. Once in the ante room with everyone we three slaves dropped to assume the position in from of Mistress Catherine. "Stand up my lovelies", she said as she produced a pair of surgical scissors that had one rounded blade. She slipped them under the rubber band around my balls. When the band severed the intensity of the pain subsided quickly leaving a dull ache.

She cut the elastic of the condom and the blood flow to my genitals was re-established as the pair of condoms was removed. My cock was free of its tormentors. Leonardo removed the leather hood that was enveloping my head and deflated my gag. She pulled it out with a "pop" and I slowly closed my mouth. "Oh, THANK YOU." "You're welcome dear," said Leonardo.

Mistress Catherine left the room for a minute and returned with a tube of some salve. "Leonardo, please remove those nipple clamps carefully. Loraine, the pain will intensify when the clamps are removed but Venus will apply some of this and the pain will diminish quickly." "Yes Mistress, I understand," I replied.

Leonardo released the cam lock on the right nipple clamp and I staggered from the increased pain. I took in a deep breath and moaned through clenched teeth. Venus immediately massaged some of the balm into the punished flesh. It hurt even more for a moment as she rubbed the nipple, but the balm quickly did its job and the intense pain was replaced by a dull ache. The same was repeated for the left nipple and I was rid of them.

"Thank you, oh thank you Mistress."

"You're welcome my pretty slave."

Venus released my elbows while Leonardo freed my hands, moved behind me and unlocked the seven straps loosening the waist belt. I could breathe easier now. The straps over my shoulders were removed and the crotch strap was also removed as my now semi hard cock and balls were freed from the genital ring.

"I'm going to remove your butt plug," said Leonardo, "Please bend over a little so it will come out easier." I bent over a little and Leonardo pulled on the leather straps to extract the butt plug. At first it didn't move and she pulled harder. As the bulge reached my sphincter I cried out, "Please hurry, it hurts so much!" Leonardo gave it one last effort and it pulled out.

Venus immediately applied some balm to my ass hole, pushing her finger as far up my ass as she could to spread the balm around. "Oh, that feels goooood Venus, thank you." Venus took a handful of the balm and started smearing it on my cock and balls, massaging it gently into my suffering genitals. My erection returned as I moaned with pleasure. Venus stopped her wonderful massage to help Leonardo remove the boots and hobbles.

I was totally naked, with another roaring hard-on. Venus hugged me and said, "Welcome to our family Loraine, I love you." She pressed her latex clad body against me and kissed me pushing her tongue passed my lips. I responded and kissed her back. Leonardo took her turn; bending at the waist she hugged me pressing her leather clad body against me.

The spider web breast covering chaffed a little on my tender nipples as she said, "Loraine, I have longed to have another sister, welcome home. I Love you." She kissed me passionately, thrusting her tongue into my mouth. I responded and felt another wave of emotion pass over me. "I LOVE ALL OF YOU!" I said.

Mistress Catherine walked over to me and hugged me gently, kissed me on the forehead and said, "It's official, welcome to your new home. You have demonstrated the ability to withstand an extremely severe session without losing your self-control. You accepted your fate without question and passed an important test." There were no words in the English language to describe my joy at the sound of those words.

"The three of you have about two hours to bathe and get to know one another, before you clean up the penthouse and get ready for tomorrow's activities."

Venus took my cock in her hand and led me out of the room squealing with delight. "Come on Leonardo, time's a wasting!" Leonardo was right behind me. As I followed Venus' shapely, thonged, and latex covered ass, watching it move in response to the gait enforced by her ballet boots, and 18" hobble. I felt a desire to kiss her all over her pretty ass.

We went to the bathroom with the big roman tub. Venus said, "Help Leonardo out of her catsuit, you'll find all the keys in the top drawer over there. I'll get the bath started." She turned and adjusted the faucets, adding bath oils, as I started unlacing Leonardo's Catsuit. Venus came over to help and in no time Leonardo was naked except for the cock restraint.

I got the key and released Leonardo's splendid cock. God, she was beautiful, tall and statuesque, lovely facial features, large firm breasts, flat stomach, and that big exquisite cock! Her body was devoid of hair and with the exception of her cock and balls was a woman. I reached out and fondled that beautiful appendage.

I was full of mixed emotions, I loved my new sister Leonardo and wanted to kiss and fondle her tits, to fondle her cock and balls, yes, to even kiss and suckle that manly appendage. I had never considered myself a cocksucker, but it was not at all like some hairy masculine cock, rather a smooth feminine cock. "I love it too," said Venus. "Go ahead and kiss it, it won't bite." I dropped to my knees and took her cock in my hands.

It WAS beautiful. I felt my own cock swell as I hesitantly licked around the heavy gold ring and kissed the now swollen head. I stroked that magnificent shaft and leaned under her cock and took one of her hairless balls into my mouth. As I gently sucked her right ball into my mouth Leonardo moaned with pleasure. I shuddered with pleasure also at the idea that I had excited sweet Leonardo so. My cock was fully engorged now as I got into this erotic endeavor. I started to take some of her cock into my mouth, silently cursing the cock ring for being in the way.

"Hey you two, I'm here too." We had forgotten about Venus, and stopped what we were doing for now. I stood up and patted Leonardo on the ass, bent over and brushed my lips over her left nipple and said, "I have never known a love as intense as I feel for the two of you and Mistress Catherine."

"WE know." they said in unison. We released Venus from her latex bondage outfit, and climbed into the tub. Leonardo and Venus were already kissing and fondling each other’s breasts, so I took a deep breath and went diving to find Venus' love mound. Finding her smooth shaven pussy, I locked on to her clitoris and sucked it gently into my mouth where I tongued the shaft of her clit. I felt a hand on the back of my head pushing me tighter against Venus.

I responded by rapidly flicking her trapped clitoris with the tip of my tongue. She responded by pushing my head even tighter against her pussy. She was really hot and the clitoral stimulation did the trick. Venus stiffened a little and released the grip on my head. I came up for air. I think I would have drowned if she hadn't cum so quickly.

The next 45 minutes was spent discovering each other. I learned that Venus can experience almost unlimited multiple orgasms. A fact that certainly made me jealous.

I stroked and fondled every square inch of my new slave sisters' bodies. I learned that Leonardo's cock ring was not a permanent one. Mistress had a special tool that removed it whenever she wanted. The ring had been a gift from Mistress Catherine for Leonardo's acceptance of Mistresses desire to have her transformed from a man to a woman.

Soon after the hormone treatments began, a piercing specialist was called in to pierce Leonardo's cock and insert the ring. This specialist, Mistress Enide, a statuesque black Mistress, also pierced Venus' nipples. I was told by my sisters that Mistress loved pierced slaves and had informed them that more piercing would be done at some future date. I kissed and sucked her fabulous cock and Venus gobbled up Leonardo's cum--several times--as well as mine. Nectar of the fountain of youth, ya know.

There was about an hour left when we finished in the tub. Venus gave Leonardo a facial treatment with the hot towels and the gooey lotion followed by the strange smelling soap. "This hair control process is European and lasts about 4 days," said Venus. "Feel your face Loraine." I did and it was just as smooth as this morning and it was after 4:30 in the afternoon. Amazing!

Leonardo and Venus showed me how to properly apply make-up to make me into the beautiful TV I saw this morning. They showed me how to make my long permed hair look soft and feminine. Additional balm was applied to my sore nipples and genitals.

There was about 40 minutes left and Mistress Catherine announced over the intercom that she had laid out outfits for each of us. We were instructed to eat the meal to be found with the outfits and get dressed. "Thank you Mistress" we all said. Leonardo and Venus showed me where the outfits could be found. They explained that we were in the part of the penthouse called the slave’s quarters. There were no locks on any door as slaves have no privacy. The main entrance to the slave quarters was a pair of automatic doors controlled by our omnipotent Mistress.

We walked into a large bedroom furnished with three queen sized poster beds. These beds were of heavy duty construction with a complete frame around the top of the posts and a built-in mirrored ceiling. The posts were extra strong and the bed equipped to secure a slave in a multitude of very strict bondage positions. I could see that the phrase "going to bed" could take on a whole new meaning. "Yours is the one on the left Loraine," said Venus. "Mine is in the middle and Leonardo on the right."

We dressed, assisting each other as necessary wolfing down the lunch that was left for us. I was wearing the now familiar latex dildo pants with the cock restraint strap attached to a waist belt. These were different in that the dildo was as large as the average erect penis and not just a butt plug. The dildo still slid easily into my enlarged anus, thank you. A lovely red and black latex, heavily boned waist cincher that squeezed me down to 26".

My chest was enhanced by a male breast harness that required the help of Leonardo and Venus to push and pull my tit flesh until I had what looked like a well shaped, but small set of tits. All the pushing and pulling of my tits and nipples was painful due to tender state of my recently tortured nipples. The straps of the breast harness were lined with soft rubber to hold them in position insuring that my tits would not slip out of their embrace.

My new tits were covered with a tight fitting black shiny latex bra that made me look very sexy. My mouth was filled with 2 pair of soiled panties that Mistress had retrieved from the hamper and then taped with 3 pieces of 2" wide red vinyl tape to seal them in. A three inch leather slave collar adorned my neck and my legs were encased in a pair of red seamed stockings attached to 6 garters from the waist cincher. The shoes were a pair of red and black, 6" heeled pumps with locking ankle straps connected with a 14" hobble chain. The feeling of the feminine lingerie was intoxicating. I gently stroked myself basking in the sensations from the nylons, garters, and latex.