Candy's Day


This contains Sissy porn and sex acts. Leave now if you should....everyone here is above 18 years old. Love ya!


I have always loved the feeling of something lacy or sexy on my body. I call it a passion of some sorts, wearing these things made me feel very special and desirable. I was raised by my mom and the closest family we had was my Aunt Trish and her two daughters. To start my collection of these things to wear, I would take things they left lying around the house and later claimed as my own since I assumed they were things that were lost. My mom was always working or going to my aunt's house on the beach for the weekend. I never was a problem kid and always made good grades in school. Mom never required me to work a part-time job, but I did often baby-sit for the Roberts' next door.

My mom named me Andrew after a relative on her side of the family, but I grew up being called Andy. Until my Aunt Trish and mom draped a nickname on me that I have carried with me till this day Candy, when I was younger I could eat candy for dinner since I loved it so much. I didn't tell them but ring pops and lollipops became my favorites later on because I often imagine I was sucking a good hard cock. I have never considered myself gay, just someone who loved the female persona. When they say "clothes make the woman" I think it is also attitude. I feel more female than I will ever feel male. At only five foot four, finding cute girls clothes is not really hard to do and I actually love having such a small frame. My light brown hair that is about shoulder length can be styled so that it can look really cute, yet could be put together so I can just look like another teen kid in school. After my eighteenth birthday alot of things fell into place for this story.

At school, I didn't have a clique that I hung around with since most of the kids knew I lived with my mom and that I was busy with her all the time. It had been just the two of us for as long as I could remember and I liked it that way. My mom wasn't home often, so I had a lot of time to be myself. Two girls who lived in Carlton Oaks, the ritzy section of town, gave me rides to the mall after school so we hung out a lot there. They would ask me to parties but I always had an excuse like I was going out to the beach to my aunt's house. Steffi and Lisa were always nice to me, since they usually bought our food at the mall and gave me rides back and forth most of the time. They knew my mom gave to the local charities; one day each one of them left a bag of clothes at our garage door. I found some really hot stuff going through those bags and once I was done I gave the rest to my mom for charity.

At least three times a month when mom was at Aunt Trish's, I had the house to myself to do any kind of play I wanted too. I would dress up and stay that way until the second I knew she was coming home. I had my digital camera setup in my room one weekend and was letting it take snapshots of me doing and wearing various things. I couldn't get my hands on real sex toys, so I used different things to satisfy Candy's desires, usually vegetables and household items always seem to work very well. This particular weekend, Mrs. Roberts from next door called and said her husband was wondering and if I was OK since he had seen flashes of light coming from inside our house. I assured her I was fine, that I was getting pictures of some stuff my mom wanted to sell on eBay. I laughed when I hung up the phone, since her hubby brought it to her attention and it was her hubby's hard cock that I was imagining was inside of me.

The Roberts' were always very good to me and my mom, I saved a lot of money from what they paid me to do work for them. They always seemed to be happy and good people to be around, since I was there second only to my house and school. Tracy Roberts is a sharp blonde who carries herself very well and doesn't look like she has given birth to two kids. However, Mr. Roberts is a sight to behold! I love to watch him when he doesn't know I am staring. He looks like he just stepped out of a GQ magazine and the Wall Street Journal combined, any woman would love to have him between their loins. He had a really good job with a large magazine company as a photographer in which he has to travels a lot, often like his wife. He is almost six foot two and built like a rock with a sleek black bald head.

The weekend when Mrs. Roberts' called about the flashes stands out very prominently in this story I am going to tell here, but that will come in time. Steffi and Lisa dropped me off at home after our usual outing at the mall, I was hoping for some playtime but I saw the light blinking on the answering machine so I pressed it to see who had called while I was gone. It was Mr. Roberts, who I called Mr. Rob, deep voice coming from my answering machine. He said "Hi there Candy it is me, Tracy is out of town and I need a sitter really, really bad. I have a nine o'clock dinner meeting in town and hope you will call me soon. Thanks!" I got my cell phone and called Mr. Rob, he picked up rather quickly so I knew he was desperate or acted that way anyhow.

"Hi Mr. Rob, I just got your message and you sounds like you need help" I said.

"Yes, I really do. When can you be here Candy, I will pay you double" he replied.

"Oh! It is no problem, today is Friday and mom is already on her way to the beach. I will get some stuff and see you in about ten minutes" I told him. Since it sounded like I might be spending the night, I got my bag and packed it, freshened up with some powder I bought at the mall as a gift for mom and put in a really cute and new belly button ring that I bought as a gift for myself. I changed into a pair of red running pants, but not before I slipped on my favorite pink thong and grabbed a cute tee shirt since I knew I could workout in the Roberts' exercise room. I checked my hair and pulled it up in a rubber band, slipped on my running shoes and headed out the door. DAMN! As soon as the door closed I remembered my keys on the dining room table, so I looked in our hiding place for the spare key, but that key was also gone since Aunt Trish used it last weekend to stop by the house.

I knocked on the door when I got over there, Mr. Rob came to the door looking as good as ever and I smiled as he invited me inside. I was on the phone with my mom telling her I needed her to come to town and let me in the house sometime this weekend if she possibly could. Mr. Rob heard me leaving mom a voicemail and just started laughing. "You're locked out?' he said but I pretended to be pissed off, just not with him. "Yes, I am and she is in a dead zone with her cell phone." I told him. We both laughed and he said, "Well, me and the kids have you longer this weekend then we planned but that's OK. You know the kids love you and this is like a second home to you Candy."

"You need to keep that nickname quiet you know, I don't want everyone knowing it," I said as I dropped my bag on the living room floor. He smiled and started to get his stuff ready for his dinner meeting. I went to looked for the kids so I can keep them out of his way for a few minutes. Before he left, I gave him my new cell phone number and got his too.

Things went really great sitting for them, they had dinner, played and watched TV for a bit and just when I was about to put them to bed Mr. Rob called my cell phone. "Candy, my Mother-in-Law just called and wants to keep the kids this weekend, she will be there shortly to get them so can you get their overnight bag in the hall closet ready to take with them and can you can make sure they're ready for me. I know you have the key problem but it's fine with me if you still want to stay over at the house." I told him I would have them ready to go when she got here and that I was sorry for the inconvenience about the key. Snoozing over the problem, he agreed that I was welcomed to stay over for all the time I needed too. Tracy's mom was so nice, she thanked me for having the kids ready to go and was thankful that they had planned days ago to get their grand-kids, since they hadn't seen them in three weeks or so. "Oh really, I thought this was a spur of the moment idea" I said, pondering the idea of all that. After kissing the kids goodbye, I headed upstairs to take a long hot bath since it would be at least three more hours before I expected any interruptions.

Mrs. Roberts had lots of bath products, one which was really sweet smelling, lavender scented body wash that was so dreamy I wanted to keep them for myself, but I thought better of that idea. I felt so refreshed and sweet I wanted to find something to play with in the house. I looked through the drawers in the bathroom and found one of those lint roller brushes that had a very interesting looking handle that I knew would make an awesome toy for Candy. I had a bottle of Vitamin E oil in my overnight bag which came in handy for playtimes just like this. Squatting on the bathroom floor, I was able to lower myself onto the makeshift dildo and began maneuver my sweet little ass up and down while holding the toy still. Without even touching my boy clit, I had an intense orgasm.

"Wow Candy, that was good girl! You should be proud of yourself," I said as I stood in front of the huge mirror in the bathroom. Looking at my trim little body, I used a pair of scissors to snip the little patch of pubic hair to a small area. I stayed in the bathroom and pampered myself as a young lady should for a good while, before I put on my white patch thong bikini panty and waist length robe. I slip into a pair of Mrs. Roberts' high heels and heads off to the guest bedroom where I am to stay for the next two days until mom gets home. Turning on the light as I walk into the room, I saw that it has been cleaned and made up since the last time I was here. I went over to the bed and saw a manila envelope lying on the pillow with "Candy" handwritten on the outside.

I took a seat on the bed and opened the envelope to see some photographs and a note. The photographs were the biggest shock I have ever had in my life! They were pictures of me wearing a hot pink outfit and pleasuring myself as a little sissy slut. "What the hell is this?" I say out loud! Immediately, I went to the note that came with the pictures. Written on the note was "I hope you are not too shocked by these pics Candy, especially since I loved them so much. I hope my plan works out for this weekend so I won't have to publish these on the internet. I have left you a gift hanging in the closet in front of you and I am expecting you to be wearing it when I get home tonight. Love Rob!"

I begin to shake like crazy as I am sitting on the bed, thinking I may lose my virginity to a gorgeous black lover. I went over to the closet to see what is in there and saw the most beautiful hot pink lingerie outfit I have ever seen in my entire life on a ruffled pink hanger. Attached is a note that says, "If you like this, there will be more to follow!" A full set with the bodice, hose. garter, a very small thong panty and the heels were on the floor underneath. Alot of effort went into getting this stuff together, not to mention the sheer confidence that I would not balk on the whole idea. Somewhere between totally flattered and frightened is where I was at right now. I sit the outfit on the bed, steps out of the heels and removes my thong panty. Beginning to dress as Mr. Rob's sissy actually was getting ready for my first date I thought, as a girl mind you. Everything fit so nicely and when I slid the thong panty up over my thighs and in place set off the warmest feeling inside and I just felt like the most beautiful girl in the whole world. I tucked, tightened and checked the last bits of the outfit and went to the huge mirror to see Miss Candy. The heels were a bit taller than what I was used too but managed nicely. Sitting at the vanity and applying my makeup for my date added about 100 butterflies to my gut and at times yet all I could do was smile.

Bringing my camera with me in my overnight bag seemed now to be a good idea and I used it to take some self pics in the huge mirror. Posing like a Playboy centerfold I felt just as pretty as anyone ever in that magazine. "Playboy Centerfold Candy" I spoke out loud and laughed.

"I think you could be in a magazine anytime you wanted to Candy!" I hear from the doorway.

I almost fell on my face right there and catching myself on the back of a sofa chair that was in the bedroom. "Mr. Rob!" I sounded off. Reposing myself and wondering what to say I looked over to him and all I could do was smile. Pulling my hair behind my ear I composed myself and looked over to Mr. Rob standing in the doorway.

"You are actually prettier than I thought you would be, yet I am not surprised at all! I hope you like the outfit I picked out since I thought the pink would fit your personality. Above all I was worried about the size but one more size down would have been way too small. You look amazing Candy, he started by saying to me making me lose a few of those butterflies in my gut.

The man who I had known as Mr. Rob was standing there in a knee length white robe smiling at me and I know I had the deer in the headlights look on my face. "Well I hope I get at least a runway walk, so I can view the beauty in pink I know as Candy. I am sure some photographer would pay good money to do a photo shoot of you in the outfit" he said.

Slowly I begin to walk towards him and then to the right, back to him and over to where I was standing by the huge sofa chair. I stop with one leg bent and my hands on my hips, giving him a really big smile. Mr. Rob walks over to the bed, sits down and motions for me to come over and take a seat beside him. "So how shocked were you when you opened the package and everything was described to you Candy?" he said. and added "I want you to tell me everything."

"Shocked was not the word to describe how I felt and when I first read it and saw the pictures, I wanted to run home and lock all the doors. But I thought if you went to all this trouble you must really be someone special. I love the outfit and I think you are the most incredible looking man I know. I feel very lucky to be here and I want to say thank you for making this a night I will never forget" I spilled my guts to him. Acting as giddy as a kid over a new bike I have this smile that, seems painted on as we sat on the bed.

"Well Candy I have seen you a few times in play mode while your mom was gone and I knew you had to someone I wanted to explore more to see what makes you tick.. You have an incredible body and that outfit is surely made for your frame.. Given the right tools I have no doubt that you could make incredible money with that body. I have seen lots of things in photography and you are really special!" Mr. Rob claimed. He had a very eager listener and all I wanted to do was rip that robe off of him and see that specimen of a man. As he spoke he motioned for me to lie down behind him on the bed and relax. "I think I have waited long enough to get my hands on this little body and I want you to feel like a real lady" speaking to me as I made myself comfortable on the huge bed. I was on my belly but I had my head turned to him the whole time as he got behind me and began to massage my lower legs and thighs. Up and down using those large hands of his my body could be wrenched I know with just a thought. But Mr. Rob was really wanting this night to be nice I knew. Stopping just below the edge of my ass cheeks he would go back down to my calves and begin his ascent to the top. I felt a tug on my hips and he slid a large pillow under my hips as to arch my back and raise my tiny ass a few inches. Then is when he placed those hands on my ass cheeks and I felt all of those butterflies leave my belly and my body temperature must have hit new highs. I turned my toes inward to make my ass cheeks open a little more, burying my head in the pillow.

"So how's your evening going so far Candy?" he asked leaning down to my body I feel his body touching mine for the first time. "I am doing just wonderful so far!" I reply feeling his hard rock body on my backside. I can feel the pressure against my hips and ass as Mr. Rob begins to grind that hard cock into me. "Does that feel good on your backside Candy? Do like the feeling of my hard cock pressing your tiny body? I want to make this very special and I hope you are ready!" Mr. Rob tells me. At this point all I can do is moan and try to keep my nerves together, "Yes Mr. Rob. I am ready for you to do whatever you want to with me. That's why I am here right? That's why you have done everything to this point to put us together, right?" I ask him.

"You are exactly right Candy and I am going to make you into a sexy girl tonight, exactly what I think you have wanted for a long long time." Mr. Rob. states. I then feel him rise up and touches the top of my thong panties and removes them over my legs and feet. Out of the corner of my eye I see the panties land on the pillow beside me and I feel my ass cheeks getting nudged open. The thick fingers spread my cheeks and starts poking around my tight little boi cunt. Teasing me as I can only moan and enjoy the first touch to my rosebud. Pressing a little harder Mr. Rob's finger presses into my sphincter and causing my boi clit to stiffen like a steel rod. "That's just a tease of what you are in for tonight young lady so why don't you turn over to me and get your late birthday present" Mr. Rob says. I turn around and with a little nudge I end up on my hands and knees facing him and I come face to face with a black men's thong that holds the object of all my desires.

Up on his knees Mr. Rob. instructs me to remove his thong and see what I have been missing all of these years. I reach out to remove his thong and slowly I see the most wonderful thing in the whole wide world. I didn't know what to compare it too but was semi hard and hanging at least eight inches from the base and the head looked like I could spend the rest of the night feasting on cock and not finish.. "That's all yours Candy so Happy Birthday, and I hope it is the right size for you!" he tells me. I lower my mouth and kisses the base of where it is hanging from and starts to lick the dark black shaft. My own juices wet up the shaft so it glistened like black marble. "It is the most beautiful gift I have ever received and I can't wait to show you how much I appreciate it too." I tell Mr. Rob. I then lowered my head to the long shaft and starting back licking it up and down.

I must have been doing a pretty good job because as I did the head of it began to rise up until it was as high as my mouth. I wanted to wait but the sight of that hard black cock made me crazy. The head tasted better than any candy I have ever had in my mouth and was already wet with his wonderful precum. Engulfing that black rod was all I had in mind and that's exactly what I did. I slid down to place my head under his cock and pulled his hips to where I could easily suck the head without moving very much. I was moaning like a dog in heat and he knew I was really enjoying myself. Occasionally looking up I saw the pleasure on his face and was happy to be doing this for him. Up until this time I had yet to touch is cock with my hands and didn't need to either, my lips kept it exactly where it needed to be. I began to bob up and down slowly taking a little more than the head but I could not resist going back to the head of that sweet cock. I feel Mr. Rob's strong hands lead me to the edge of the bed so that my head hung off the side and he brought that black cock right back to me. He began to move his ass around and made his cock roll around in my mouth and then it popped out and slid across my face causing both of us to laugh very loudly. I was glad because a seconds break seemed to ease some of the tension and gave me time to catch my breath too.

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bydaisyboi_sissy© 14 comments/ 90677 views/ 44 favorites

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