Sissy Amy

Amy. That was the name I used to go by when chatting online. I met my master on Omegle chat, he said he was 19, but I never saw him, so I've no idea if he was or not. I was in my mid 30s at the time and found the idea of a younger Dom humiliating. Although to be fair, I'd have found the idea of a fat, bald, 60 year old Dom equally humiliating.

I used to log on to Omegle each weekend night after a few drinks. I'd list out my interests as 'top', 'bottom', 'sissy', 'humiliation', 'master', 'Dom' and that kind of thing.

We matched one evening and had an interesting chat, I was incredibly turned on and horny. He knew exactly what to say and teased me before allowing me to cum. We agreed to both set our interest to "sissyamy" the following Friday so that we would match and chat.

This continued for a number of weeks and I soon got more comfortable with him. He began to set me tasks and I took photos as proof of my completion. They were posted to a website (I think it was called kinktalk), for him, and anyone else to see.

Nothing too extreme or testing, photos of me naked, lots of photos of me in different lingerie sets or bra and panty combinations. He was pretty fair at letting me cum, although he knew my kink for denial. We agreed on the honour system rather than a physical cage and I was committed to staying true.

Most Fridays and Saturdays we chatted until I was hard, dripping and throbbing. He'd often have me edge myself during our chats and would provide me edging instructions to follow during the week.

When allowed to cum I always had to consume my mess. He gradually began to extend the periods of denial and I got more and more horny. This made me more open to sharing my fantasises and desires with him. He knew exactly what to ask, what to say and how to behave. He had total control over me and I loved it.

It was a period of time when I was travelling around the country on business, often stopping in a hotel for a night or two and we soon realised that these were opportunities for me to carry out tasks which turned me on. Having taken account of my fantasises he set me one of my first major tasks.

I was to go to a supermarket and buy the following items:

Matching bra and panties

Cucumber

Lube

Nothing else. Just those 4 items. I was then to choose a check out with a female cashier and pay for them. My opportunity came one day as I drove into Ely and saw a large Tesco store. It was here that I would experience my first public humiliation task.

I walked into the store and picked up a basket then headed to the clothing section. I chose a matching panty and bra set. It was white with butterflies on it. Brazilian style briefs, size 12 and a 34C bra. I then headed to the fruit and veg section to choose a large straight cucumber, before picking up some KY lube in the pharmacy/bathroom section.

I was so nervous now, my stomach was churning. I wanted to abandon my basket and leave the store, but I worried if I didn't do as my master had asked, he may cut off contact with me.

I walked the length of the shop in front of the checkouts, assessing the cashiers and the queues. I saw the one I wanted. She was a very pretty, young girl, maybe early twenties with dark curly hair, but she had a small queue. I did a full lap of the store conscious that anyone could take a look in my basket and see my perverted shopping choices.

I came back down the aisle that I thought would be opposite her checkout, I could see she didn't have a queue. My mouth was dry, my cock was twitching and my heart was pounding. I was going to do this.

I almost ran to the till, to make sure no-one else got there before me. I avoided eye contact with her, as I put my four items on the conveyor belt. I was conscious of another customer at the end of the belt starting to load their shopping out of their trolley. Surely they must see what I was buying!

The belt moved and my items moved towards her. I looked up as she started to scan them, it was now her that was avoiding eye contact with me. I felt excited, sick, nervous, embarrassed, thrilled and humiliated all at the same time. It was a feeling like nothing I'd ever experienced before. After scanning the last item though she looked up at me to tell me the cost. It was at this point that I came in my pants!

I hadn't expected that to happen and tried my best to act natural as I got the cash out of my pocket, while load after load of cum spurted from my semi erect cock into my pants, while standing at a checkout in a Tescos store! I took my change, stuffed my items into a carrier bag and raced out of the shop.

Later that evening, in my hotel, I took the required photos and uploaded them to kinktalk:

All 4 items

All 4 items and the receipt

A close up of the receipt

Me wearing the bra and panties

Me with the lubed up cucumber up my arse while wearing the bra and panties.

I told master about my experience the following Friday night. He was angry that I'd cum without his permission. He said I would now need to go for an extended amount of time without cumming as punishment.

Three weeks passed and I was incredibly horny. I knew I wanted to progress to the next step. I suggested a cam session for him. He was reluctant as he didn't want to show his face. I said I would look into options.

I soon found an app called "AppearIn". I could enable my camera and he could keep his off. He would have the choice of enabling his microphone and talking, or typing his instructions. He could stay completely anonymous, if he chose to do so.

The following weekend, I shared this with him, along with the fact that my next overnight stop away from home would be in about 3 weeks time. He was excited by this prospect and agreed that we should do a cam session, but I would not be allowed to cum until that session. We counted up the days passed since Ely and the days until the planned hotel stop in Reading - 54 days in total!

I had other business journeys planned and he suggested I use these to acquire anything I might need or feel was appropriate for the cam session, but I wasn't to tell him what I had bought as he wanted it all to be a surprise.

I spent the next 3 weeks buying items to wear:

Matching pink bra and panties and black hold ups from Asda in Chelmsley Wood

Electric blue basque and panties from Peacocks in Chelmsley Wood

Short black leather mini skirt and sheer cream blouse from Matalan in Newark

A mask to hide my face and some wet look hold ups from my local fancy dress shop

The purchase of most of these passed without incident and therefore aren't worthy of comment (the lady serving me in Matalan definitely knew they were for me though), however I want to share the story of purchasing the final item/items. En-route to Reading I planned to call in at Anne Summers in Oxford to buy a suction dildo and a chastity cage.

I entered the Anne Summers shop and selected the dildo I wanted. It was 6", black and had a suction cup. I searched the shop, but couldn't see any chastity cages. Nothing to lose at this stage, so I asked the lady behind the counter if they had any.

"I don't think so", was her answer, before she shouted to her colleague on the other side of the store. "Jess, this bloke wants to know if we sell male chastity cages".

I went bright red and nearly came in my pants in a shop for the second time in my life. The whole store was looking at me. There was a guy in his 50's, two middle aged couples and a good looking teenage couple. I felt all their eyes on me as I purchased my dildo and rushed out of the store.

That night, at the agreed time I logged on to "AppearIn". I was dressed in the hold ups, pink lingerie set, leather mini skirt, sheer top and mask, to hide my identity. I was very nervous and very excited.

I sat on the chair in my hotel room trying to breath calmly and slowly, while waiting for my master to join the app, He was a few minutes late, but the screen of my iPad divided into two sections as the connection was made. Me dressed as a slut with my camera and microphone on, his screen black and blank.

"Hello Sir", I said in my best girly voice. His response was via typed command. It was apparent that I would not see or hear him this evening, but I resolved to put on the best show that I could.

I showed him the dildo that I had bought. He had me show him my body, do some twirls, then with hands on head he had me face front and count to ten, then to the side for ten, face away from the camera for ten, then the other side for ten.

Then he ordered me to remove my blouse and skirt before repeating the 40 second 360 degree turn, in just my bra, panties and hold ups. I was getting turned on by the humiliation of this. An anonymous person (who I assume really was a guy) was taking in every inch of my body from every angle. My cock was tenting in my panties.

Next I had to remove the bra and panties before repeating the 40 second 360 degree rotation again, this time naked apart from my hold ups. My next task was to show him my blow job skills on the dildo, before he ordered me to stick it to the chair and ride it.

I was nervous as this would be the first time I'd ever had anything in my ass, other than the cucumber, which was only in long enough to allow me to take a quick photo. I took a sip of water from the glass on the desk and eased myself on to it.

The feeling was amazing and my embarrassment level was high which made me all the hornier. I was naked in a hotel room, riding a dildo on camera for a guy I couldn't see. My hand went to my cock and I was wanking as I rode the dildo.

He didn't like that! He hadn't given me permission to touch it and ordered me to stop. I continued to ride for another 5 minutes or so, before he asked me what other clothes I had. I panned the iPad around to show him the electric blue basque, panties and black wet look hold ups that I'd laid out on the bed.

He approved and told me to place the camera in a position so that he could see me getting dressed in them. Once dressed, he had me stand facing the camera with my hands on my head for 30 seconds before his next instruction came though.

"We are going for a walk. Tuck your door card in the top of your hold ups and pick up the iPad. You must go to another floor of the hotel and walk the full length of a corridor before you are allowed back to your room."

I nearly vomited right there. Was I really going to do this? Of course I was! I was overcome with excitement and horniness. I'd have done pretty much anything at that point, with little consideration for the consequences.

I picked up my door card and put it in the top of my hold ups as he had suggested, picked up the iPad and carefully opened my hotel door. Having previously taken some photos in a hotel corridor in the Lake District, this hadn't come as an entire surprise to me, but the requirement to go to another floor was a whole new level of risk.

I'd scoped out the situation earlier in the event of this request coming up and knew that I could do a loop. Left out of my room, up or down the back stairs along the corridor which ran above/below mine and then back down the main stairs to my floor and back to my room.

So that is what I did. Wearing the electric blue basque, and panties, wet look hold ups and face mask, with iPad in hand and my hard cock straining against the fabric of the panties. I did a loop of my floor, the rear stairwell, the floor above and the main stairwell.

I got over confident on the floor above and stopped to check for messages from my master near a large window. He spotted the window, ordered me to place the iPad on the floor behind me, face out of the window and count 20 seconds - whatever I heard or whatever happened I was not to move!

Fortunately nothing did happen, I snatched the iPad up and hurried back down the main stairwell to my floor with a growing damp spot from my precum showing on my panties. I heard some voices down below near reception, which briefly concerned me, but I got back to my room without any issues.

Master was pleased. He said I'd earnt my reward and would be allowed to cum. I was really looking forward to this. 54 days of teasing, edging, doing tasks etc had got me hornier than I'd ever been and this cam session was the icing on the cake.

He ordered me to get a glass, I knew that was coming, but it didn't make me any less disappointed that I'd have to drink 54 days worth of my cum. Then he asked me if I knew what a "ruined orgasm" was. I responded, of course, that I did. That really did upset me a little as he'd never even mentioned ruined orgasms before.

And there I was in a hotel dressed in electric blue lingerie, ruining my first orgasm for 54 days into a glass, and I was so excited, so horny and so happy. As I came, my legs turned to jelly and I had to hold myself up with one had on the desk as I caught my cum in the glass in my other hand.

I was now totally spent, my horniness had evaporated and I wanted this session to be over. Master made me beg to be allowed to drink my cum, which of course I did as I wanted to please him in the hope that I could have another session like this in the future. There was a lot of it, but I gulped it down as a well trained sissy should.

After drinking it all, I started to undress. Then I saw his command on the screen "STOP, Did I say you could get undressed?"

I apologised. He had me redress, before thanking him for the session, requesting permission to undress, which I had to do while he watched, before finally getting permission to log off.