Where We Left Off Ch. 06

I didn't feel like I was dressed like a girl. It didn't feel like Halloween to me. It felt like I had always been Tiffany, but never realized it before this moment. I felt like myself

"Come here Tiffany," John said, seated in a chair by the bed, "Lay across my legs."

I knew what was coming. A camcorder was setup on a tripod. It's red light flashed. I laid over John's legs. John pulled down my shorts.

The first swat came down with a slap. It wasn't too hard. John rubbed my cheeks then gave me two more slaps. John slowly massaged my bottom. He gave me me two more little slaps and one big one. He spread lube on my entry and worked a finger into me. He fingered me awhile and then spanked me. He alternated between the two for awhile and then inserted a butt plug into me. He gave me ten hard swats with plug secured in me. It stung but I was so horny. Being spanked had never made me horny with Randy. I allowed Randy to spank me because he enjoyed it. Being spanked by John felt good. John made it pleasurable for both of us. John put me down gently on my knees. He bent over and kissed me on the lips.

This was my first kiss ever. He kissed me passionately and held me close. He cupped my red cheeks. John picked me up and brought me to the bed. He positioned the camera and made sure it was setup properly. He laid on the bed with his upper body propped up by pillows.

"Make love to me with your mouth, Tiffany." He said.

I was excited. I had dreamed of sucking his monster for months. I pulled his pants down. I pulled his briefs down and revealed his manhood. It was rock hard and now it was all mine. I kissed all around the head and licked his mushroom and shaft. John tasted like pure man and sweat.

I worked my mouth around John's engorged member. I brought in as much as I could and sucked him gently at first, rubbing my tongue on his head, working it in and out. John moaned as I worked my magic on his tool. He leaked precum and I icked it up. His taste was better than dinner. I was addicted. I got the head to the entrance of my throat, but no further. I worked what I could of his massive cock. I licked every square inch. I took him back in my mouth and sucked hard on the withdrawals. John moaned in ecstasy. John looked at me with lust in his eyes. I knew he wanted more.

John picked me up and threw me to the side of the bed. He went to the closet and came back with a box full of restraints, chains, and ropes. He locked cuffs around my ankles and wrists. He placed a collar around my neck. He locked my collar to a ring on the footboard of the bed. I couldn't move my head and was stuck looking at the wall of the room. He shackled my wrists to my ankles. John pulled my thong down to my knees, exposing my entry and my boy parts. John placed a cage over my little cock and locked it in place tightly. He slapped my bottom with his large cock. He pulled on my legs until I was in the position he wanted. He grabbed my hair and put it in a ponytail. I could hear him squirt some lube out to grease up his cock. I waited with bated breath. He removed the plug from me and I could feel him push his monstrous cock up to my entry. He penetrated me. I relaxed as much as I could, but nothing could prepare me for his size. He pushed slow and his mushroom head popped completely inside. My entrance now relaxed around the other side.

"Are you okay Tiffany?" John asked

"Yes sir." I replied.

The initial pain was replaced by intense pleasure as he pushed deeper into me. He allowed me to acclimate to his size. He then grabbed my pony tail and yanked hard as he thrust into me. He pumped in and out of me. He increased his rhythm and flat out pounded me. His cock smashed into my button. He found it with ease and pulverized it. My body was pushed and pulled hard against the restraints. My little cock was so hard in its cage. I came harder than I have ever cum in my life. John picked up his pace more. My orgasm set off a chain reaction in him. He erupted in me. My void filled with his seed.

John removed all of my restraints except for the cage on my cock and my collar. Those were permanent. He kissed me and held me til we both feel asleep.

I slept in the next morning. John wasn't in bed. My bottom was sticky from his seed. The top sheet and blanket had been removed from the bed. The blinds were open, which was unusual. John was a private person and kept them closed. To my left was a note.

It read, "Give him a good show. You may unlock yourself and masturbate with toys and your hand. You must stop if he leaves. You are only allowed to have an orgasm if he has one first. Put your cage back on and find me once you are finished."

I looked out the window and saw the landscaper that had spied on Randy and I earlier. He stared at me and stroked his olive colored cock. John had placed lube, my toys, and a key on the nightstand.

I bit my lip and thought about it for a second. I slowly got up and let him see all of me. My soft body, my bottom that was still red from being spanked last night, and I even flashed my boy parts in the cage. The landscaper stroked harder.

I removed the cage and grabbed the purple dildo with a suction cup on the bottom and attached it to the window in front of his cock. He came closer to the window. I began sucking on the dildo as if it was a cock. Soon I had the dildo down my throat, while he stroked furiously, only an inch away from lips. I rubbed the lube over the dildo I turned around and pulled down my thong. I lubed my hole and fingered myself seductively. I pulled my finger out and sucked on it while I stared at him. I then backed up to the dildo and worked it deep into my anus. Looking forward I could see the camcorder on its tripod, it's red light flashed on and off. I fucked the dildo. I gyrated my hips seductively as I fucked the dildo.

I looked back in time to see him cum. He came all over the window. I picked up the pace and soon my little cock exploded in my hand. I showed him my cum. He smiled at me and put his cock away. I cleaned up, put my cage back on. I went to the bathroom and flushed myself out and brushed my teeth. I then looked for John.

I found John in the living room. The Suzuka Grand Prix Qualifying Recap was on TV. Villeneuve had put his Williams on Pole. John was not happy. John was a McLaren super fan. The whole house was filled with Senna, Hakkinen, Hunt, Lauda, and Prost memorabilia.

"Mika is going to have work his magic tomorrow," John said with disappointment.

"Did you give Juan a good show?" John asked.

"Yes sir," I replied.

"Good girl," he said, "I laid some clothes out for you, take a shower, do your makeup, and get dressed. We need to leave the house in 40min."

I ran to the shower and did as I was told. John had set out a thong, a medium length black skirt, a black garter with black stockings, and a white t shirt that would expose my midriff. I dried my hair, put on my makeup, and got dressed. I checked myself out in the mirror. I looked hot. Hopefully we wouldn't be outside much because it had cooled down this week.

We stopped at our usual cafe for coffee. My favorite barista was behind the espresso machine. He looked at me a little surprised, then smiled.

"Let me guess, two tall white chocolate mochas. Extra whip cream for the sir?" Brad, the barista, said.

"That sounds great, young man." John replied.

Brad made our drinks. He kept looking at me as he made them. Something was familiar about him. His smile reminded me of a kid that was a close friend of mine during middle school. He smiled a lot, the same way. His family only spent the summers in town. I lost track of him during high school. He had been my closest friend as a kid. Coincidentally, his name was also Brad.

Brad handed a coffee to John, and said, "Be careful sir, it's hot." Brad then handed me a coffee. He looked at John and said, "I don't have to warn her, she is already hot."

Brad had a big goofy smile on his face and said, "Come here for the coffee, come back for the jokes! Y'all have a nice day!"

John grinned as we walked outside. John mentioned several times in the past that he thought Brad would go far in life. John grinned at me and said, "He recognized you and he thinks you're hot." John slapped my ass and said, "He's right, you know."

Sometimes a compliment can make a girl feel good, and I felt great at this moment. I truly had feelings for John, but Brad could make my heart stop with a blink of his eyes. Being called hot by Brad made my year.

John pulled up to a tattoo parlor. He wanted me to choose a tattoo that commemorated the birth of Tiffany. The artist designed a butterfly with the previous day's date designed into it. John thought it would look sexy on my lower back. The artist got ready and took my drivers license. He looked at the license and then at me with a puzzled look on his face. He finally photocopied it and gave it back to me. John loved the tattoo. I liked it too. It was the first tattoo for either of us. John then chose a navel ring and ear rings for me. I went over to the piercing side of the shop and the artist pierced my ears and navel.

John and I focused on work that winter. He trained me as his submissive. The rules started out slowly. They were only focused on the bedroom activities at first. Then more and more rules came. The punishments came too. John would do our erotic spankings with his hand, but his punishments were with straps and paddles. John also believed in maintenance punishment. A punishment in between punishments, a sort of reminder every once and a while.

I practiced hair and makeup. We went back to the waxing salon as needed. We feel into a good rhythm. Randy had moved in with Brantley. Brantley rented a carriage house downtown. It was part of a mansion owned by an eccentric guy named Andy. Randy told John that Brantley paid his rent with sexual favors instead of money.

It was the spring of 1998 and John still had some issues in regards to any masculinity that remained. He discussed options with a couple different doctors.

"Your penis is small and doesn't really bother me. Both doctors said it would be too small for them to make into a usable vagina. Especially to be of use to me. Your ass is perfect for me in every way, I don't need another entrance on you," John said, "I believe our best option is hormones and some plastic surgery in the future."

"Do I have a choice, sir?" I asked.

"Yes, you always have a choice," John said, "but only one of your options will advance our relationship. I cannot continue in a relationship with you in your current state."

My time with John had been good. John was strict, but all my needs were met. John had always been right. I never planned on having children, but this was medical procedures. I had no alterations to my body besides a few piercings and a tattoo. I could end my relationship with John and physically resume life as a boy. Truthfully, I was too far down the rabbit hole to resume life as a male emotionally.

I couldn't go back home as a sissy. My parents would be so embarrassed if anyone in their church heard I was a sissy. They had sent me to bible study retreats as a teenager. It didn't take long to notice each time that it was always boys, and the boys all seemed gay. Each lesson was about homosexuality and our eternal souls. My parents could never accept me like this.

Randy was with Brantley and I do not think we could ever be close friends again anyways. I had a great job with John. I would have to find a job, a place to live, a roommate, and I would still struggle. John protected me, supported me, and loved me.

I agreed with John and started hormone treatment and blockers. I couldn't believe how feminine I started looking. My little cock shrunk even more, as the doctors predicted. It could still get hard, and my sex drive remained high. My orgasms from bottoming were still intense.

The hormones softened my skin. I grew curves. I had to be more careful with my diet. A plastic surgeon shaved my Adam's Apple and made a slight adjustment to my chin and cheekbones, which made me look more feminine. John started me on laser hair removal treatments. John looked into implants, but the doctors recommended we wait to see if I grew breasts on the hormones. John became worried about my weight. He wanted me to weigh ninety-five to one-hundred-five pounds. He put me on a strict 800 calorie a day diet with no sugar and almost no carbs.

Men in public stared at me, cat called me, groped me, and tried to get my phone number. It didn't help that John insisted that I dress provocatively. John loved the attention I got in public. John's appetite for sex increased ten fold. He could not keep his hands off me or his cock outside of me.

We helped Randy and Brantley celebrate their 1 year anniversary in July. I could tell Randy had no sexual attraction to me anymore, I was too feminine. John sold my old car and bought me a new Volvo sedan. He wanted me to have a safe car. John loved teasing Brad at the cafe. John would send me to get coffee in outfits that revealed more and more as time went on. Brad eventually became unable to hide how he felt about me. He understood that I was in a relationship. He just wanted me to know his feelings if my relationship with John changed. I kept this information from John.