Sissy Awakening Ch. 04

Sarah)

I didn't know what to do. I searched the house like it was some kind of a joke she was playing on me. This was completely out of character for Sarah. I checked the kitchen and saw the personal appliances that were hers were missing. All of her toiletries were gone as well.

In our bedroom it was a similar situation. She had taken all her clothes and left mine behind. She left some of the clothing I had bought for her over the years, things I guessed would remind her of me. It was all so surreal and I was having a hard time comprehending the situation. I went to my room to lay down and cried myself to sleep...

I awoke early the next morning and just sat there in the clothes from the previous day. I couldn't find the will to do anything. Sarah, my best friend of over ten years didn't want to see me again. She packed up and left. She didn't love me anymore. I can't say I could blame her either. I didn't think I was worthy of love thinking about all the things I'd done over the last week.

I wasn't sure I wanted to do anything at all. I wasn't sure I even wanted to play these games anymore. She was the reason I was wearing the dresses and panties... I did like the clothes and panties but what was her idea and what was mine?

(Knock, knock, knock...)

Someone was pounding on the door. Who the fuck could be pounding on the door this early in the morning.

I ripped the door open, ready to yell at whoever was knocking that damned early when, none other than Trinity Stevens was standing at my door looking as beautiful as ever. She saw that I hadn't even changed and could tell that something was wrong by the look on my face. She stepped inside when I broke down and started sobbing right in front of her. It was as though all the built up emotions of a lifetime lost came flooding out. And the remorse for the last week of indiscretions and infidelities from both my end and hers.

"It's okay Sam." She said hugging me.

I tried to give her a response, but nothing coherent would come out. Everything I was up to this point, good and bad had pieces of Sarah attached to them. My job, Sarah knew someone that worked there, this house that Sarah and I bought together, Sarah found it and fell in love with it. She painted the living room that dark blue even though it made the room seem smaller. This was her home and I fucked it all up by wearing her fucking panties! I fucked our life off because I couldn't resist women's underwear.

I felt like maggot shit. I destroyed a perfect relationship because I wanted to wear her panties. I wanted to die right then because of how much I hurt her.

I was a mess and she held me right there inside my doorway until I managed to say more than two words. I gave her the note Sarah left for me and let her read it. I was thankful she spared me the discomfort of reading it aloud.

She couldn't see everything the letter said that wasn't written down like, I don't want to spend another Christmas where we spend more money than we have on each other. I don't want you to be my Valentine ever again. I don't want you to hold me after you've had a rough day ever again. I don't want you to ever touch me again. You disgust me and there's no way you'll ever not be disgusting again. I wish I would have never met you.

When she finished she hugged me long and hard and didn't let go until she sensed I was getting better. She called in sick for the both of us that morning and she stayed with me until later in the afternoon talking about how life had a funny way of working out. I told her my story of how I had gotten to where I was right then and we discussed where I saw myself in the coming months and years.

I did actually enjoy living as a woman, a slutty woman no doubt. I liked certain aspects of being a sissy but for the most part it was a fun fantasy. I missed touching my cock but since it was not an available sexual appendage, I focused on other ways to get what I wanted.

"What do you want to do?" Trinity asked.

"I have a couple weeks vacation time saved up, I'll just use that and get some shit figured out." I said.

"I don't really want you staying alone right now. Will you please come stay with me?" She asked.

I didn't know what to think of that. There were some issues with that on its own. I was still attracted to her and I felt she was worth more than to be a rebound. She was likely my unicorn and I didn't want to ruin that too.

"If you and I are ever going to be anything, I don't want to jeopardize that with how fucked up I am right now." I said.

"Let's both promise to be completely honest with each other okay!" She said.

"I'll go first... I've always had a bit of a crush on you ever since you hired me, and then Thursday you started changing... I found my interest had doubled." She said.

"I really had forgot your name, but I always did like looking at your body and I often fantasize what it would be like to be with you. And even more so that I know you have a penis!" I said taking my turn.

"I feel like I need to be punished for what I've done." I said not really thinking.

I was near tears again. I wanted to hurt physically more than emotionally. I could deal with the physical pain more than the mental anguish.

She helped me gather a bag of clothes for Sam and another one for Samantha. I wasn't sure who I was right then. We closed up my house and I left a note for Sarah just in case she came by when I wasn't there.

(Sarah,

I'm sorry I fucked our life up. I'm sorry I hurt you. I'm sorry that I couldn't stop being me. I don't expect you to ever forgive me. Take what you want from the house, I think I'm just going to sell it anyway.

Sam)

Sarah and I ended up splitting for good. We talk every now and again but irreconcilable differences is what it's called.

I rode out my two weeks vacation time with Trinity. We had become quite close in those two weeks. It was Monday and I was due to be back to work. I got dressed and ready for work. Doug knew I was coming back in and wanted to talk.

I pulled my favorite black thong panties up my legs then put on a pair of slim cut jeans that made my ass look amazingly fuckable and pulled a black button up shirt over a camisole and added a black sport coat. My fingernails were painted midnight blue, and my hair slicked back. I thought I looked like a more metro-sexual version of David Blaine.

"Lots of changes over the last month!" Doug said.

"Yeah, lots of changes." I copied.

"Come let me have a look at you!" Doug said.

"About that... WE aren't going to make that mistake anymore." I said.

He looked floored, but regained his composure and accepted the fact that he would have to go back to picking up male prostitutes wherever he used to find them.

"What do you want to do then? Your desk is still down in the basement unless you want to go back out in the field. Your position out there has been filled, but you might be able to work into something." He said.

"I'm good with the desk job sir." I said

He nodded his approval and I turned to walk away.

Work ended up being work, and the office ladies were still catty toward me but I got to see Trinity a lot. And I didn't even have to turn my work truck in.

At the end of the day, we sat down for a nice dinner together. The food was good and I was glad to be sharing a meal with Trinity. I kept stealing glances at the dungeon door. We hadn't consummated our relationship yet and I was still wearing the chastity cage at her request. My dick felt like it was constantly hard with how horny I had been and how little sex I was having. Two weeks was Trinity's request and it had been two weeks.

"Do you think you're ready for that?" Trinity asked.

"I'm ready for whatever you want!" I said.

She unlocked the door to the dungeon and flung the door open wide.

"Go down, pick where you want to be this first time, strip naked and assume the position." She said before she walked away toward our bedroom.

"I'll be there soon." She added.

My mind went off like fire crackers. I didn't need that much time to decide where to go! I almost ran down the stairs to the dungeon. I hastily stripped everything off and found the narrow table that she strapped me to two weeks ago. I laid across the table and positioned my neck in the large hole and my arms in the smaller holes of the stocks. It was in the exact same position two weeks prior.

Ten agonizing minutes elapsed before Trinity walked down the stairs. I could hear the clicking of her heels on the concrete floor behind me. She strutted like a runway model right in front of me. I immediately noticed her large breasts and how her nipples stood out like dark gum drops begging to be chewed on. She wore an underbust corset that was as black as a lake at midnight. Six thick straps fell out the bottom and dropped into her shiny black thigh high pumps.

She paced in front of me as she explained the rules. She used the same Red, Yellow, Green safeword system the Millers had used. I heard what she was saying but all I could focus on was her prick. She came down without panties on and her cock swayed back and forth as she walked. It was six inches long and somewhat thick. It would have been just fine if she were hard but I knew it was going to grow! I could barely wait to get ahold of that cock!

Trinity finished her instructions and rules and then dropped the top of the stocks down over my neck and hands. My head and arms were immobilized. She pulled the table forward away from my legs and started playing with the cage entrapping my cock. All I could think about was how beautiful she looked and how big her dick was.

The moment the lock came off, my dick forced the cage away from the ring holding my balls. I felt the tube being pulled out of my urethra. It was such a foreign feeling not having it in there. My cock hung free for the first time in three weeks.

Trinity stroked my throbbing penis and fondled my balls. My breathing quickened from her touch and my mind didn't know what it wanted. I wanted her to make me cum by playing with my cock and I wanted her to touch my ass. She was so close to it. I wanted her to fuck me!

She brushed her fingers along my anus, and my whole body trembled with desire. I wanted her inside me so bad!

"Is this what you want?" She asked.

"Oh my god, yes!" Was all I could say.

Fire erupted from my left butt cheek, and a sharp cracking sound registered in my ears.

"You'll address me as Mistress down her slave." She reminded me with a voice that carried a bit of playfulness.

"Yes Mistress." I replied

She took the striking end of the crop and started rubbing my balls with it. They tensed up involuntarily when she gently slapped one with the crop.

"Is that what you want?" She asked.

"If it would make you happy Mistress..." I replied somewhat reserved.

I had shared everything with her. The ball beatings included. While it wasn't the worst thing I could think of, it definitely wasn't on my list of top ten favorite things she could do, but if that made her happy, I could deal with the pain.

Trinity gently slapped at my sides, right over my kidneys, and then up my ribs and under to my nipples. The strikes weren't meant to cause pain, she was just looking for a response from my body. When she started striking the tender flesh of my nipples, my skin prickled up into goosebumps.

Trinity stopped and walked around to the far wall and retrieved something. She squatted only an inch from my face. Her cock had stiffened substantially and was maybe 8" long.

"These are nipple clamps. They're only meant to add contrasting sensations." She said as she clipped each one onto my nipples.

Trinity stood and stroked her girl dick an inch from my face. She grew to just about 9" and thick as a rope. She rolled a condom over the head and stroked it down the length of her shaft. I watched with intense desire as the condom changed the color of her dick from a pale peach to a dark grey and, like a pair of pantyhose, everything was smashed down and smoothed out.

What started out as intense nipple pain slowly changed into a warming feeling in my chest. She switched to a flogger, and would toss the tassels into the air and let them fall across my back. It sounded amazingly sexy. She positioned herself directly behind me and worked the entirety of my back, letting the end wrap around and hit my sensitive nipples. Every flick on my nipple produced a shocking sensation. Deep massaging impacts thudded across my back and she occasionally countered her soft blows with sharper stinging blows.

She had moved down to my buttocks and upper legs. Sharp stings would fall only an inch from my balls and I would jump. Trinity was delighted by the fear and would giggle in such a playful way.

After ten minutes she stopped and had resorted to using her bare hands. I felt warm fingers brushing the inside of my thighs and across my sex hole. I poked my ass out toward her fingers as she touched the opening of my hole. All my nerve endings were turned on and ready. I felt her hands as she explored my lower back, ass and legs while she licked my balls, taint and anus.

She jabbed her tongue into my anus like a small wet penis. It was so intense I couldn't concentrate on anything and my mind became a puddle of pleasure.

I felt her stand up and place the head of her cock at the slimy opening of my asshole. Her fingers raked down from my shoulders sending electric shockwaves where ever she touched until she grabbed ahold of my hips.

Intense pressure built at my hole as Trinity forced herself into me. I could feel my hole stretching to accommodate her cock and with every thrust I felt my own dick leak a little bit.

Trinity fucked me from behind for an imperceivable account of time. My cock was rock hard and spurting fluid with each thrust into my ass. I felt her nails dig into the soft flesh over my hips as she started shuddering. She pulled her cock out of my ass and air sucked in to replace it.

She stepped around in front and removed her condom. Her thick cock throbbed and bounced as she unclipped the lock on the stocks.

"On your knees!" She said pointing at the floor directly in front of her.

"Yes Mistress!" I said eagerly.

The clamps on my nipples moved with each step and small jolts of pain courses through my chest. I knelt down and she locked handcuffs behind my back, and stepped back around in front of me.

My mouth was directly in front of her thick bouncing cock, and she pushed it toward me. I parted my lips and touched the head of her dick with my tongue before she even got it in my mouth. Trinity didn't move.

I fucked her cock with my mouth. I wanted to taste her cum! I wanted it to fill my mouth, and only a short moment later I got my wish. She grabbed ahold of my head and fucked my face hard as she shot rope after rope into my open mouth. Her um was thin and watery with a salty sweet flavor that I instantly loved. I sucked her as long as I could. She ended up pulling her dick out of my mouth with a loud poping sound.

"Stand up, it's my turn." She demanded.

I stood best I could with my hands cuffed behind my back and stretched my back out. Trinity knelt in front of me and took my slime covered prick into her warm velvet mouth. She licked my balls with my cock buried in her mouth and probed two fingers into my asshole. The moment she touched my prostate I started shooting my seed into her throat. She pulled back and let me fill her mouth.

She was still on her knees when she opened her mouth to show me how much I had given her. She stood up and clamped her mouth over mine and plunged her cum covered tongue into my mouth and pushed my own seed in with her kiss. She spit the cum into my mouth and opened hers to receive it back. We swapped my cum several times until she was satisfied and she swallowed her share. I left mine there a moment longer and swallowed when she released the clamps from my nipples.

Fresh pain erupted from my nipples and she placed each one into her soft sensual mouth to ease the pain. I bit my lip to contain the building excitement she was causing with her mouth already.

We left the dungeon, her still wearing her corset and boots while I was still naked as a Jay bird. Trinity peeled her costume off and stood at the foot of our bed completely naked. My cock had stiffened again and I was ready to fuck. Trinity shuffled backward onto the bed and opened her legs.

"Come make love to me Sam!" She cooed.

I climbed onto the bed, hovered over her, lubed my prick and kissed her open mouth. I then pulled her legs up to her chest and placed my cock against her opening.

"I think, I love you Trinity!" I said as I gently pushed my cock into her ass.