Tich's Toyboy

My name is Steve and I have an online friend named Tich. She first contacted me after reading one of my stories on an Erotic Story website. I answered her feedback and she replied again. Soon we became online pen pals and chatted using AOL Instant Messenger.

I learned that Tich is in her late 40's with green eyes, dark brunette hair and rather large tits. All of which I found to my liking, there isn't anything more sexy than a mature women. As we chatted the topic of sex came up. It seems that Tich can never seem to get enough sex from her husband who tries to keep her happy, but just can't keep up with her. Tich had never been unfaithful to her husband and he knew she had male friends that she chatted with on the Internet. He said her chatting did not worry him, as it was only words. I explained to Tich that my wife was not very turned on by sex anymore and that I had not been getting enough. We both laughed at our situations and continued chatting and exchanging emails over the next several months. I would let her know how each new story was coming along and she always said that reading them made her so hot she had to rub herself for relief. An author can't get better feedback than that!

As time went by the IM's heated up until we were having cyber sex. Tich was very hot online, telling me how much she liked to suck cock, that her pussy was shaved bald and that she always came while reading my stories. I came hard as she described how she would suck my dick and would email me after a cyber encounter giving me the details about how she rubbed her cunt and how many times she came while online with me. We became quite close, as close as two people can be living over a thousand miles apart. We not only chatted for sex talk, but for the more normal day-to-day things that go on in a person's life. From time to time Tich would suggest a story for me to read. I liked her taste in stories and read what she suggested to help me better understand her tastes.

About three weeks ago Tich recommended a story about a man whom was dominated by an online Mistress. The story was very good and left me wanting more. We discussed the story at great length; both of us sent feedback to the author encouraging him to continue the story. We kept up our usual conversations over the next two weeks.

Last Saturday while I was at work, we often chatted while I was at work, the subject of the Domination story came up again. I told Tich that I wish I had a Mistress like in the story. Tich said that she often fantasized about dominating a man and we both wondered how much fun it would be. I asked her if she would like to be my Dominatrix. Tich warned me to be careful what I wished for. I told her I was not kidding. After assuring her that I wanted to have a Mistress and much begging Tich agreed.

We or should I say she set up the rules. I was to get a new screen name that reflected my commitment to her, I was always to address her as Mistress in any emails or IM's, I was instructed to continue to correspond with her using my regular screen name and I also had to choose a Safe word in case things got to be too much for me. I eagerly went to work and in a few minutes time had a new screen name to use when contacting my Mistress.

Now chatting as my Mistress's new Toy she asked if anyone was around at work. I told her I was alone. Mistress ordered me to unzip my fly and squeeze my wee-wee. I complied immediately and she said that I had pleased her. Next Mistress instructed me to cum in my hand. I came almost as soon as I read her words! Now with my hand full of cum I asked what I was to do next. Mistress instructed me to lick my cum off of my fingers and describe the taste to her. I sat close to my desk; my left hand in my lap full of cum as I looked to be sure no one was around. The coast clear I raised my hand to my mouth tasting my own cum. After licking all the sperm form my hand I responded to Mistress that the cum was very sweet, warm and silky on my tongue. Pleased with her control over me Mistress told me that she was going to give me some orders and that I must follow them or she would terminate our relationship. I told her that I was eager to follow her instructions.

My first orders as my Mistress's new Slave were to buy woman's panties to wear to work and some condoms to wear so my wee-wee as she called my cock would not soil my panties. I was to send her pictures of the receipts as proof of my obedience. I left work early on Saturday to buy the items my Mistress instructed me to get. I stopped on the way home at a women's clothing store, "The Fashion Bug". As I entered a female clerk asked if I needed any help. I told her that I would let her know as I felt my cock harden as I wondered if she would figure out that I was looking for panties for myself. I found the undergarments and searched the racks trying to figure out what he sizes meant. Unable to make sense of the ladies sizes I began to hold up different pairs of underwear, stretching them out to gage the size by eye. I finally settled on a black pair of briefs and approached the counter to pay. The woman at the counter asked if I found everything I was looking for and if I would like to charge my purchase. I told her that cash would be fine as I looked around at the other clerks and female customers watching me buying ladies underwear. My heart raced and my hands trembled as I paid and left the store. Early Sunday at work I took photos of the receipts and emailed them to my Mistress.

I watched the screen for a reply from her. Soon I got a reply saying that Mistress was pleased that I had made the purchases so quickly. I told her that I wished to please Mistress and was happy to obey. Next I was instructed to go to the men's room and change into the panties.

The silky fabric of the panties felt cool on my skin. Almost immediately my cock began to harden in my panties as I imagined my Mistress inspecting the fit. I left he Men's room with a tent in my pants and made my way back to my office. I sent an IM to Mistress telling her that I was now wearing my panties. Mistress replied with further instructions; I was to wear my panties form home to work each day and at night when I showered I was to masturbate until I felt that I was going to cum then squeeze the base of my cock to prevent my climax. The orders were strict and clear; I was not to cum unless given permission! I assured Mistress that I would obey her commands and asked if there was anything that I could do for her now. Mistress told me that each and every time my dick got hard I was to squeeze it for her, no matter where I was or who was around. I replied that I understood and was squeezing my hard on now. I spent the rest of the day at work with a raging hard on for my Mistress, squeezing it whenever I thought of her (which was often). It was a busy day at work; I made many trips into the plant wearing my panties under my clothes. The silky fabric kept my cock hard as I rubbed against it as I walked. Near the end of the day I received another email form Mistress informing me that I was to go to an Adult Toy Store and purchase a butt plug. Of course I was to send a copy of the receipt the next day.

I left work still wearing my panties and went to the nearest Adult Store. Inside I felt my dick harden again as I looked through all the toys hanging on the wall. Near the back I found an assortment of butt plugs, most of which looked like they would split a person in half! As I continued to look another man walked up next to me and was looking at the plugs also. He did not speak. I wondered if he was looking for a plug for himself or someone else? I finally decided to start out small; selecting a two-inch silicone plug I made my way to the register. The clerk at the register was a woman about fifty years old. She did not even look up at me as I handed her the money to pay for my new toy. Back in my car I realized that if I was going to use this butt plug I probably would want some lube so I stopped at Wal-Mart before I got home and bought some K-Y Jelly.

Finally at home I raced to the shower to masturbate. I was so desperate to stroke my cock, as it had been hard with excitement all day. I undressed quickly remembering to store my panties in my briefcase so my wife would not find them. It would be rather hard to explain why panties that were not hers were in the laundry! I started the water and began to stroke my cock. My shaft was soaked in pre cum; I switched hands as I licked the clear liquid from my fingers. My dick swelled as the taste of my pre cum filled my mouth. Switching back to my right hand I jerked my cock furiously. My balls pulled tight against the shaft as I felt my cum begin to build up to release. I remembered my orders and clamped down tightly around the base of my cock just as it started to twitch. Another stroke would have been too late and I would have cum. I felt proud that I had the willpower to stop as instructed by my Mistress and yet felt that I still needed to cum. I turned around to the showerhead reaching for the controls to switch to cold water. The cold water did the trick and my cock started to deflate. I had survived my first day as my Mistress' Toy Boy.

Monday morning I took a photo of the receipt for the butt plug and emailed it to Mistress. I waited sitting at my desk with my panties on as Mistress had instructed for her reply. Finally an email came. Mistress wanted to know if there was a female clerk at the Toy store and if it had excited me to purchase the butt plug from her. I responded that the clerk was indeed a female however she did not seem very interested in what I was purchasing. Mistress then sent me an IM. I have further instructions for you Slut, her IM read. I want you to go to another Adult Toy Store, one with a younger female clerk and get her to help you buy a cock ring. I replied that I would try another one near work that afternoon if it pleased my Mistress. Next Mistress wanted a full description of how I jacked off form her in the shower the night before. I gave her every detail of my masturbation session and she was pleased that I was able to stop with out cumming as she had instructed. Mistress wanted to know when I would have another day off from work. I told her that I would be off tomorrow, Tuesday. Mistress was pleased with this and told me I should go to the Adult store to purchase the cock ring as soon as I could and that she expected a copy of the receipt and a description of the clerk in my morning email to her. Mistress promised that we would have fun on my day off and reminded me to jack off again that night without cumming.

I left work as soon as I could. I pulled into an Adult Toy Store called 'Vicious Boutique' after ringing the bell and waiting to be buzzed in I heard a woman's voice on the intercom. 'May I help you?' came the voice over the speaker. I relied that I would like to come in and that I hoped that she could help me. Inside I walked past a display of fetish clothing, mostly woman's undergarments, some made out of latex and all very sexy. Passing through a beaded curtain I found the clerk waiting for me. She looked to be in her mid twenties with long black hair and a nice build, even if it was hidden under a loose sweatshirt and sweat pants. She explained the sales they were having and asked if there was something special I was looking for. I told her that I was told (just told, not by whom) to get a cock ring. She showed me some jelly rings and some that looked like condoms with ticklers on the end. I told her that my instructions were to buy a cock ring that would help maintain an erection and control ejaculation. My cock swelled in my panties as I explained what I was looking for and I squeezed my hard on as instructed by Mistress. The clerk noticed and smiled as she lead me to another room were a male clerk was hanging new stock on pegs on the wall. The clerk began to explain the different types of cock rings to me. She suggested a set of three rings made of white latex. I asked how they should be worn. She explained that the large one goes around the penis and the balls, it has to be put on before the penis gets an erection she smiled as she watched me squeeze my cock again. Then selecting the smallest one that will fit it should be slid over the penis until securely at the base. She seemed very knowledgeable and I complimented her being so and that it was nice to find a place that had such a helpful staff. She thanked me for the comment and asked if there was anything else she could help me with. I told her that I was also supposed to be looking for a butt plug (I had already purchased a plug, but she was so helpful I thought I would see what she recommended). We moved to another wall and she described all the different kinds of butt plugs to me. I told her that I was interested in one that could be used for an 'extended' time. She suggested a four-inch silicone model that she explained could also be used with a strap-on harness; she smiled wide as she told me about the strap-on harness. My cock was about to explode! I wished Mistress were here with me to enjoy the attention this young female clerk was giving me. I purchased the cock ring set and the butt plug. Thanking the clerk for her help I turned to leave. She smiled and winked at me as she told me to enjoy myself and to come back again.

On the way home I stopped at Wal-Mart to buy some more panties as Mistress had suggested. My cock was still hard thinking of the clerk at the Adult Toy Store as I looked at the 'Just My Size' selection of panties. The packaging was very helpful giving hip sizes along with the panty size. I selected a three pack with yellow, silver and purple (Mistress' favorite color).

I went home, masturbated in the shower thinking of my shopping trip, the hot little clerk and of course my Mistress. I was only just able to stop jerking off before I came in the shower that night.

Tuesday after my wife had left for work I took pictures of the receipt for the cock ring and new butt plug and attached them to an email with a complete description of my shopping adventures to my Mistress. Soon I received an email telling me to put on the cock rings as the clerk had described and to were a pair of my new panties. I quickly put the items on and returned Mistress' email confirming that I had done so. I also told Mistress that I had some errands to run and that I wished to IM Mistress when she had time for me. Mistress returned my email instructing me to try out the rings and small butt plug and to run my errands with it inserted in my ass. If I was a good Slut and did as Mistress asked I was to IM her to tell her how my errands went.

I grabbed the K-Y Jelly and the small butt plug. Nervously I put a small drop of lube on my finger and worked it into my asshole. My cock swelled in the rings, which I had put on as the clerk in the Adult Toy Store had instructed. I stroked my cock a few times then picked up the small butt plug covered it with lube and slowly worked it into my ass. As the tip of the plug pushed past the outer ring of my ass I stroked it in and out as my Mistress had described in her email. Once I was used to the feeling I pushed the plug in until the flange at the base was against the outside of my butt hole. The full feeling was new, but not uncomfortable. I pulled my panties up then my pants and headed for my car.

My first stop was at the beer store. I purchased a six-pack to be used to cook Bratwurst for dinner that night. The clerk at the beer store was a woman and my cock was hard so I grabbed it to give it a squeeze for her to see. She seemed indifferent my a man in the store squeezing his cock in front of her, maybe this was a frequent occurrence? She was pretty ugly so I doubt that was the case. Next I went to the bank. I walked right up to the teller. Sara was her name. She helped me with the banking as I leaned against the counter rubbing my hard on against the hard surface. My heart was racing standing in public with a butt plug in my ass and cock rings on covered by women's panties. Could anyone see my panty line? Could they tell I had a plug in my ass? Surely anyone who looked could see the bulge in my pants, as my cock was rock hard and throbbed with each beat of my heart.

Back home I went to my computer to IM Mistress. Thankfully she responded. I gave her all the details of my exciting errand run and begged her to allow me release. Mistress toyed with me, asking if the Clerk in the Adult Toy Store where I had purchased the cock rings and second butt plug made me hot. I truthfully told Mistress that she had made me hot, but only because she was helping me to select toys that my Mistress wished me to have. I asked if I could stroke my cock for Mistress. Mistress told me to wait. Mistress then asked if I realized that the clerk in the Adult Toy Store must be a Dominatrix? I asked why she thought that? Mistress told me that how else would the clerk know so much about cock rings and butt plugs and that the butt plug was well suited for use with a Strap-On harness and that she smiled at me every time I squeezed my cock in front of her. I agreed that she was probably right. Mistress asked if I would like to cum for her. For you Mistress, I replied. Mistress then gave me precise instructions on how I was to masturbate for her and signed off.

I was sorry Mistress ended our chat, but very glad she had ordered me to cum. I turned off the computer and went to the bathroom. I removed my panties and grabbed my cock as I began to stroke it. Pre cum leaked from the tip. I scooped it up and licked it from the fingers of my free hand. My balls swelled up as the largest cock ring held them close to the shaft, my hand hitting them with each stroke as I jerked my cock. I removed the smaller butt plug, lubed the larger four-inch butt plug I had purchased from the Dominatrix clerk and pushed it past the opening of my asshole. I worked the plug into my ass until it was in all the way and was placing pressure on my prostate. I imagined that Mistress was fucking me with a Strap-On as she had indicated in my instructions. My knees began to weaken as the cum boiled in my balls. Just as my cock started to twitch I pulled the plug form my ass causing me to shoot my load onto the vanity top. I trembled as my dick squirted sperm until my knees became too weak to hold me up. I knelt down to complete my Mistress' instructions. Licking all the cum off the vanity I rolled it around in my mouth savoring the taste before swallowing it down my throat.

I cleaned up my toys and put them away in my briefcase before taking a shower and cooking dinner for my wife. I had a hard time sleeping that night thinking of my Mistress fucking me with her Strap-On and how good it felt to cum earlier in the day.

Wednesday morning I read the days instructions before emailing the description of my masturbation session with the butt plug in my ass the day before. I was instructed to wear the small butt plug to work along with the cock ring and my yellow panties. I had orders not to make a mess by cumming in my panties and reminded that if I did cum in my pretty panties I would be punished. A slut that comes in her panties would have to wear her cum filled panties for the rest to the day to remind her what a dirty slut she was. Now I was being referred to in Mistress's emails as a Slut and a she. I sensed that I was going to be feminized even further as time went on. As I thought about this my cock began to harden and I knew if I was going to get the ring on I had to hurry! I quickly left the computer found my butt plug, K-Y Jelly, my smallest cock ring and my panties. In the downstairs bathroom I placed the cock ring on my dick just before it got too hard to get it all the way on. Next I lubed the small butt plug and pushed it at my asshole. To my surprise my butt opened right up to except the plug and I pushed it home without any trouble. I slipped on my yellow panties, pants and boots and headed for work.