The deal with Sarah was simple; I'd have to humiliate and degrade myself fully and of my own free will. We often used each other for pleasure. It wasn't a relationship, it wasn't friends-with-benefits, it was just convenience.
Sarah lived in the flat next door. She was a petite girl around 5'5 and had a sweet, innocent look. You'd never imagine her to have a filthy mind or be interested in some of the things we got up to. Our orgasm trading began when we'd both been single for 6 months. Drinking and watching a film the topic arose of not having a good fuck in a long time and it somehow developed into her bent over the sofa and me entering her from behind... and then it ended. She attributed my short burst of sexual virility to the alcohol and long drought in my sex life, got me to eat her out and went home satisfied. She shortly discovered, however, that my smaller-than-average cock and short stamina meant I wasn't going to satisfy her by fucking her and an arrangement was made. We would take it in turns to get our orgasms. On my turns I could fuck her as long as I could last, but on her turn I was reduced to eating her out. She trained me well in how to please her with my mouth and hands but no matter how many attempts were made my cock could never give her the pleasure she needed. She never complained. She never laughed. She just let me fuck her and then got me to finish the job orally.
One night it changed. We went out drinking with friends and upon our return Sarah requested her I let her have her turn. We entered her flat, she removed her thong from under her dress and lay down on the sofa. I climbed up and got to work. That was when she made the comment that changed everything. "This is more like having a girlfriend than a man pleasuring me". The first true indication that I wasn't "man enough" for her. We both knew it was the case, but it had gone unsaid and that wasn't the problem. The problem was me drunkenly blurting out my fetish to be dominated, humiliated, feminised and fucked as a response to the comment.
The agreement had been simple: exchange orgasms. Fetishes stayed out of it. Simple, clean orgasms to avoid the monotony and dull nature of just masturbating. I had broken the agreement and as a result the agreement stopped. For another 2 weeks after this I heard nothing from Sarah, then a simple message.
"Prove to me you will go all-in. Fully humiliate yourself and submit yourself and show you belong to me - Your place, 7pm".
I was excited and nervous. I wasn't sure what to do at first. Finally I snapped into it and went on a shopping spree. I spent a couple of hundred getting prepared for the evening on an exciting shopping spree.
First I left a necklace with a key and a strapon harness on the table by the door. A note for Sarah explained that these were gifts for her when she entered the flat and that she should make herself comfortable with a drink and watch TV until I was ready. I left the door unlocked and headed for the bathroom to finish getting ready.
I began the long process of making myself more feminine. I lathered myself with sweet, fruity shower products; ridding myself of any manly odours. I shaved my face. Then I moved downwards - my chest and legs. Finally I used my clippers to remove most of my pubic hair before shaving and waxing my balls (the discomfort from wax seemed appropriate and left them feeling silky and smooth).
I showered again to remove any residual hairs, feeling the smooth and feminine skin beneath my hands as I scrubbed my body. The excitement of what was to come caused an erection. I reached for the bowl of ice I had prepared for this eventuality and used it to calm myself before entombing my cock in the plastic cage of the chastity device I had bought. The empty space at the end of even the smallest available cage reminded me of the inadequacy of my penis and how I had ended up in this situation. A situation that was once an enticing fantasy and was now all-too-real.
With my cock trapped I had committed to the scenario. I took out a makeup bag to make myself beautiful. By the time I was done I had full eyelashes and moist, red lips. I'd decided to make it painfully clear I was wearing makeup, without looking too much like a child had got into her mother's makeup. I had made the conscious decision to buy cheap makeup to ensure it'll smudge and run and make me look like the slut I am by the end of the evening.
It was finally time for my outfit. I had chosen a matching set of lingerie - red satin with black lace details. First was the garter belt and stockings, which I slowly rolled up my leg. I loved the feeling against the freshly shaven skin. Then the thong. I knew my place and that the thong would need to be easily removed. Finally I added the matching bra. I admired myself in the mirror and thought about how much I'd love to have Sarah in this costume. My cock strained against the walls of the cage in excitement as I added a black, mid-thigh dress to the outfit. The finishing touches were a pair of red heels and a pale-pink wig.
Fully dressed in my outfit I prepared one final surprise for Sarah. A gift box containing items for her to use should the evening head in the right direction. The pink box, topped with a shiny stick-on bow, contained everything she would need to continue owning me, should she desire.
By this time Sarah had let herself in and I could hear the TV. I closed my eyes and took a few deep breaths to calm my nerves as I unlocked the door and walked as sexily as I could along the hallway to the living room. She took no notice of me as I stood in the doorway. I leant against the doorframe and admired what I could see; she was simply wearing a t-shirt and jeans. Through the fly of the jeans protruded the erect strapon cock and around her neck the silver chain and key shone.
It was just an "Average Joe" dildo in the harness, but it far outweighed my own, now locked, cock. She continued to ignore me until the programme she was watching stopped for adverts. A look in my direction, a smirk on her face and a glance down at her hard cock told me what to do. I walked over and dropped to my knees. A kiss to the tip of the penis before I began to softly lick around the head whilst my hands because to tenderly stroke the shaft.
"No hands!" A simple instruction. She stood me up, spun me round and unzipped my dress. It fell to the floor and revealed the lingerie I had spent so long choosing for her. I spent so long trying to decide in the store that the sales assistant had asked me a number of times if I needed any help, enquiring about the sizes and styles I needed, whether it was a gift and so-on.
"Very sexy, looks like somebody was expecting to get laid tonight." She removed her belt and used it to tie my hands behind my back. With one hand she groped my breast and with the other slapped my bare ass cheek before pulling up the thong into a wedgie.
I was spun back round and pushed down onto my knees once again. Sarah repositioned herself on the sofa as I took the head of her cock into my mouth. With her hand on the back of my head to control me, my head bobbed up and down as I gradually took more and more of her cock into my mouth. With each movement up I flicked my tongue around the head and bobbed back down, attempting to please and pleasure the silicon in my mouth.
Soon the advert break was over and Sarah's attention moved from controlling my head to watching the show. My attention remained on the blowjob I was giving. I was now ready to push all the way down and begin deepthroating her. A brief pause at the tip of the penis before I pushed my head all the way down to Sarah's groin. I felt the head slip past the back of my mouth and felt my gag reflex go. I gurgled as I held the cock in place, wiggling my tongue over it as best I could to give it pleasure. My mouth filled with slimy, glistening saliva. It poured over the cock in my mouth and dribbled down onto Sarah's jeans.
I felt a hard slap to my face.
"If you're going to do that at least do it quietly!" she stood up and removed her jeans, revealing nothing underneath but the erection protruding from its harness. "And avoid making a mess of my clothes."
Sarah sat back down and I continued my work. I held off my audible gags, spluttering slightly with each thrust down my throat. It must have been another 10 minutes before Sarah acknowledged me again. I heard the credits rolling on the TV, and then silence. The TV was off and Sarah was staring down at me with a huge grin.
"You certainly seem to be good at this" she said as she stood up. Drool coated her entire lap and a long strand of it connected my mouth to her penis. "Looks like you got it nice and wet for me."
I was pull up off the floor and inspected. Thrown onto the sofa on my knees and my face buried in the cushions - unable to adjust myself with my hands still tied. She grabbed my thong and ripped it down to my knees.
"Oh, so that's what the key is for." Sarah chuckled at me as I felt the warm, slippery dildo move up and down past my asshole. She took little time in teasing before thrusting it in. I groaned in shock as the head slipped in. I felt lucky I had experimented with buttplugs in the past. In. Out. In. Out. She toyed with me, using only the head to stretch out my sphincter.
"Are you ready?"
