Sissy Deidre

How it all started.

I was about 14 yo and had/have an older sister who loves to wear lingerie. One afternoon I was home alone and sneaked into her bedroom. Opening her lingerie drawer my heart skipped a beat. All those lovely silk and nylon girls underwear! I took something out and let it slide down my face; so soft, so feminine, so sexy! I took a corset and some stockings and dressed in front of the mirror. OMG, I looked lovely! Could not help but touch myself and had a nice orgasm.

I returned there many times when nobody was home, till one day my sister got home early and found me dressing. Aha, she said, this is why my drawer is such a mess now and then! You like soft sexy girls underwear sweetheart? Please don’t use mine then. I stumbled something but she said; here take these stockings and suspender belt and I never wanna see you here again. With some lovely tan ff stockings and a 4 strap suspender belt I left her room.

That evening I went to bed early, wanting nothing more then put on the stockings and suspender belt. I did it in front of my mirror -with the door locked- mmmm my first lingerie, it felt soo good. That night I slept wearing the stockings and belt, must have had 3 or 4 orgasms of excitement.

A few years later, I was 16 yo, new neighbours arrived, they were from Suriname, a former Dutch colony in the Northern part of South America.The next day I was home from school early and decided to introduce myself. So I went to them and rang the door bell. The woman opened up, she wore a tight, short dress, no bra, you could easily see her nipples, she had a gorgeous big butt, bare legs and high heels; a dream for a boy my age, “Hello she said, can I help you”? Hai I said, I’m your neighbour and come to introduce myself. “That’s nice she said, please come in”.

After she gave me something to drink she sat opposite of me on the couch, her legs crossed. OMG she had gorgeous legs, her dress had moved a little bit up and I saw her thigh as well. She noticed me looking at her and said “do you like what you see?” My face must have colored red because she said “don’t be shy, a young man like you has to explore everything before he finds out what he realy likes”. This confused me, what did she mean with that?

“Come”, she said, “ I’ll show you the house”. We went to the other rooms and upstairs, she showed me the bathroom and a bedroom. On the bedside table I noticed a dildo, “did you notice it”? she said, “when my husband is away for his work I love to fuck myself with it”. I blushed again; she was so open in everything. “Did you ever use a dildo”? she asked. OMG what did she ask me, yes I use a dildo I thought, when I’m alone in my bedroom I love to push it deep in my anus, mmmm playing with my cock while fucking myself gives me such a great orgasm.

“ Do you have to think so long; I think you have a dildo as well, don’t you”? “Yes ma’am”, I said, “I use a dildo and have a great orgasm”. What did I say, I told her I use a dildo to cumm. “Doesn’t matter”, she said, “I know a lot of white boys that use a dildo to reach an orgasm”. “Black boys have big cocks to play with, most of the white boys only have small cocks”. How did she know my cock was small! I was embarassed about it, when I looked in sex magazines all the men had big cocks and the black men even bigger ones, mine was small compared to those.

“My husband has a huge cock”, she continued, “when he fucks me I moan so loud the neighbours can hear us”. “I never had a white cock”, she said, “always went straight for black”. “Did you ever had a black cock”? Was she thinking I was gay? She walked towards me and said: “I myself have fucked white boys more then once, you wanna know how”? Her beauty and apperance overwhelmed me, I could not say no.

“Okay” she said and opened a drawer, out came a dildo with belts connected to it. “This is what I use on them, it’s called a strapon, women use it to fuck their husband, because as you know in a good relation the woman is the boss”, she said. I went weak in my knees, a gorgeous black woman standing in front of me with a thing like that in her hands. “Shall I use it on you”? she said. OMG, she wanted to fuck me and that thought excited me soo much.

“But your husband”, I stumbled, “when is he coming home”? “Don’t worry he will be back around 5 this afternoon. Come, go an clean yourself up in the bathroom, I’m in the mood to fuck another white boy’s ass again”. I had double thoughts about it, but having sex with a beautiful woman like this - on top or bottom- excited me so much, I decided to give it a chance. I cleaned myself in the badroom and returned, wearing only my boxershorts.

“Take those off immediately”, she said, “as you wish, Mistress”, OMG I called her Mistress allready! In the short time I was in the badroom she chanced her outfit; in front of me stood a delicious creature wearing black leather gloves, a corset, fishnets stockings and thigh high boots and a huge strapon pointing my direction, a thru Mistress. I wanted to go on my knees to worship this Godess but she said: “on the bed on your hands and knees boy!” I did, my ass in her direction. She reached for a bottle of lube and lubed her strapon and my asshole with it. “Hold on”, she said then, “I’m gonna change your life for good now”. I didn’t understand what she meant, but had no time to think, because the strapon was entering my ass already.

Oh my, it was big! But my Mistress was gentle, slowly she went in and out, untill it was wide enough to go further. And further she went, as deep as possible, in the mean time saying things like, “hope you like it because this is your future white boy” and “take this you faggot”. I didn’t listen, but tried to relax as much as possible to let Mistress go deeper and deeper. Suddenly the door of the bedroom opened, and a big dark man stepped into the room. “Hello sweetheart”, he said, “busy making another white boy into a black cock craving sissy”? I didn’t understand everything he said, but could not speak due to the enormous strapon in my asshole and the excitement that it gave to me.

“Hello sweetheart, yes by the time I’m ready with him you can shove your big meat in to finished the job”. “Mmmmm he has such a tight little asshole” he said: “I want to use him right now”. The woman pulled the strapon out and the man took her place; “a little of lube please” he said, “to make it a bit easier for him to stand my big meat” At that time I looked back and saw his enormous cock, OMG, it was even bigger then Mistress’ strapon!

“No, please, I only came to say hello”, I said. “Too late white boy, you’re gonna be a black man’s bitch now”, the man said. He grabbed my hips and slowly forced his cock in. I started to cry, because of the excitement and pain, “easy sweetheart” the woman said, “relax you’ll gonna love it”. The man was gentle and slowly moved in and out, feeling he had more room he pushed deeper and deeper. Now his cock was half way in, his wife started to assist him, she licked his cock and balls and encouraged him: “come on babe give this sissy all you have, fill him up with your cock, fill him up with your seed”, she said.

If this was the sign for him to cumm I don’t know, but suddenly he moaned: “oohhh yess white boy, here comes your reward!” I felt his cock grow even thicker and a warm flow filling me up; he must have cumm. Oooohhh it felt soo good, my asshole filled completely with this black man’s seed! I started to cumm as well, small spurts shooting out of my tiny cock. “Well well”, the woman said, “seams our little friends likes to be taken by a real man”. I didn’t reply, but although it was painfull in the beginning,the end was so good.

“As I told you little man; a BBC is what you need. Now go on and clean your masters cock with your mouth”. I did, it was the first time I had a big cock in my mouth and something inside me said it certainly wasn’t the last time. “Come back this evening and take your sisters lingerie and clothes, we’re gonna continue what we started today”, the woman said. Come back this evening with my sisters clothes, the thought excited me, I loved to go through her drawer when she was not in, and loved to smell her panties and lingerie, once I even had pulled a panty and some stockings on, that made me feel so strange, I wonder what these people had in mind for me this evening...

After that afternoon in my neighbours house I went home with a strange feeling. I went there to introduce myself to my new neighbours and ended up being fucked like a cheap street whore. Coming home I rushed to my bedroom to clean myself. Standing in front of the bathroom mirror I looked at myself, a nice slim body, but a tiny cock; was the neighbours wife right, is my cock to small, is it my future to be fucked in stead of fucking?

On the other hand I found it so exciting to lay on the bed with my ass up high, feeling a real man fucking me as his bitch. Real man? Am I not a real man, am I a sissy as she said? I heared my mother’s voice; “dinner’s ready”. “You’re a bit quiet son”, my father said during dinner, “are you feeling sick?” “No, no” I said, “had a busy day; going to bed early”. After dinner I went straight up again, first sneaked into my sisters room to collect some of her clothing and lingerie. A cute pink panties and bra, hold up stockings and a nice tight dress. Luckely we had about the same size, so it would certainly fit.

Back in my room I locked the door and started dressing myself in front of the mirror, mmm the view excited me so; the lingerie looked cute, the dress sexy. What would the neighbours say, or better what would they do to me? I undressed quickly and put my daily clothes on again. My heart beated in my throat when I climbed out of the window and into the backyard of the neighbours. I opened the back door and said: “hello, anybody home?” Didn’t get a reaction, so I went to the living room. Also no-one there, I walked up the stairs and heard a noise in the bedroom. The door was open a bit and I could look inside, what I saw there was soo hot!

The man was lying on the bed, his wife sat on his lap with her legs spread, she was riding his cock. Her big tits moved up and down, she moaned and said things like; “yes babe fuck your bitch, shoot that hot cumm deep inside me, empty those balls in your slut, oohhh God it feels so good!” I was embarresed to witness this and decided to go back, wait 5 minutes and ring the door bell then. I did, and a few moments later the woman opened the front door. “Hello hunny, please come in, we’ve been waiting for you”.

“How are you sweetie, did you bring some girly stuff?” “Yes”, I said and showed her my sisters clothes. “Mmm”, she said, “I have something better for you, follow me”. We went to another room and she opened a drawer, ooohhhh so many sexy lingerie was lying there! “Pick what you want sweetie; we want you to look as girly as possible tonight”. I took the soft, silk and nylon lingerie in my hands and smelled it, mmm just like the first time I went through my sisters lingerie drawer. I picked out a cute pink corset with white stockings; “good choice”, the woman said; “my husband loves his sissies in pink and white”.

She helped me dress and we went back to the living room. There was here husband, sitting on the couch. “Well, well”, he said, “you look good, I love my sissies in pink and white! Come over here girl, I want you to take my cock out and play with it to make it hard”. I kneeled before this huge man, he helped me getting his cock out. It was not hard yet, but big already. I grabbed it with both hands and started to kiss the helmet. “Good girl”, his wife said, “I knew when I saw you the first time you’d be an excellent cocksucker”.

I continued kissing the helmet while tossing his cock, “lick me”, he said, “lick the shaft down to the balls”. I did, the taste was salty, think he didnt clean his cock after fucking his wife. “Good”, he said when I reached his balls; “lick them one by one”. Mmmm his balls were big, filled with seed, seed that would go into my body this evening. “You want her to lick your ass as well?”, the woman said, “no we’ll keep that for later, she’s doing a good job so far”. Licking his ass? OMG didn’t want to do that, I thought. His cock was harder now, “come”, he said, “let’s go to the bedroom and have some fun”.

We went upstairs, the woman followed us; in the bedroom he told me to lie on my back on the bed and spread my legs. He lubed his cock and my boi pussy (she told me that from now on I had a clitty and boi pussy (in stead of a cock and asshole) “Relax”, he said, “I’m gonna make a girl of you”, slowly he pushed his cock in me, out and in, out and in, further and further, deeper and deeper. I moaned, “oohh sir it is so big”, I said, “relax girl I’m going all the way in to make you my cock slut”. The woman stood behind her man and watched him ride me. “Its making me soo horny seeing that big cock of yours fucking this tiny pussy”, she said, “I need a tongue to satisfy me”.

She went onto the bed and manouvred her pussy right above my mouth. “Lick me”, she said, “lick me to an orgasm”. As I said before, she was a beautiful woman with a nice ass, now that ass was above my face! If I could, my cock would have grown hard, but I was not in the position to have a hard cock. “Yes ma’am”, I whispered and started licking her. It tasted as salt as her husbands cock, so she hadn’t cleaned her pussy as well. “Mmmmm you’re good at it sissy”, she said; “lick out my husbands seed, that will make you even more girly”. At that moment her husband started moaning; “mmmm girl, I gonna pump you full with my seed now”, he said, I felt him throbbing and felt his warm seed fill my ashole, ooohhh gawd, that felt soo good! The woman on top of me screamed: “yes, yes, I’m gonna cummmmm as well”. She moved her pussy over my face, back and forth and then stopped. “Mmmmm that was soo good”, she said, “and did our little sissy like it as well?” “ yes ma’am”I said, my clitty had squirted while I was pumped full and that felt so hot!

“Okay now it’s time for the next step”, the woman said. Next step, I thought, what did they have in mind? She left the room and came back with something colored pink. She held it up high and said: “this is step 2; a chastity cage. You’re gonna wear it when your not in our house, it is the ultimate way to control your orgasms. You may play with your dildo and have sissygasms, but never touch your clitty again”. I felt sad, I loved to play with my clitty and dildo, but that pleasure was past now.

She put the chastity cage on my cock and closed the little padlock, “the key is save with me”, she said and added it to a chain around her neck. “It is between these two friends of mine, they will guard it”, she pointed at her breasts. “Mmm time for a second round sweetheart?” she asked her husband. “Yes of course, I wanna see this sissy riding me reverse cowgirl with here clitty locked,”, he said. He took place in a chair opposite a big mirror, “come sit on my lap sissy”, he said, “both feet on my thighs, now you may controll the rithm”.

I sat on his lap and looked at us in the mirror.

As I sat there looking to myself in the mirror I realized what had become of me. There I saw a boy, dressed in a pink corset and white stockings, between his thighs was a pink cage in which his cock - or what was left of it- was securely locked. And the strange thing was: I loved it, loved to be dressed in fine, sexy lingerie, loved it to feel girly and most of all, loved it to be dominated by these 2 dark skinned people.

“Are you admiring yourself?”, the woman said, “mmm, yes you’re a good looking sissy boi, my husband loves to use you”. “Oohh thank you ma’am”, I whispered, “yes I was watching myself in the mirror and overthought what had happened to me since this afternoon”. “Okay”, the man said, “I’m gonna put you on my lap and you slide over my cock till you can’t go further, It’ll be in ballsdeep then”. “Then you move up and down, you search for the right rithm, all I do is sit here and hold your waist so you can’t get away when my cock starts growing thicker and throbbing”.

I did as he told me to, moved up and down and in the meantime watched myself in the mirror. I saw his cock disappear deep inside me and then come out again. But I also saw the plastic cage locking my cock, eehh clitty, it looked strange, felt strange, but on the other hand also save. I knew the key was in good hands and it would help me to achieve better orgasms when I was toying my ass, eehh boi pussy. The man grabbed my by the waist now, “faster sissy boi, faster, Daddy wants to pump his load deep inside your faggot ass now”. I started to move faster and felt his cock grow thicker, “ooohh Daddy, your soo big”, I whispered, right a that moment his cock exploded deep inside me. “Aaaahhhww” I shouted, “mmmmmm, yesss, ssooooo goood”! It felt like my complete ass overflowed, his seed shot out of my pussy in big streams. I almost passed out of excitement, after a minute or so he lifted me up and sat me on the bed. “Mmm sissy boi, your pussy does magic to me, I’m gonna keep you and breed you every day from now on”.

Every day? I didn’t have that much time, “no, no, I said, I have my school and homework to do, you can’t fuck me every day”. “No?”, his wife interrupted “Yes, Because if you don’t show up everyday we’re gonna show these pictures to your friends, class mates and your family; they’ll be suprised to see what a faggot you are!” She took a digital photo camera and showed me some pictures she apparently had taken of me while her husband fucked me. My facial expression was in ecstasy while his big cock was pumping in my pussy. “Oohh no, you wouldn’t”, I said. “No?” she said, “are you willing to take the risk?” She grabbed for a photo album and showed me several pictures of boys that were in the same position as I was. “See, all sissies, all being fucked by my man, all loving it. This photo album is to secure they wouldn’t run away or tell anybody, I will add your pictures to it”.

Oohh dear, I had no place to hide, they had power over me, for his and her pleasure I had to come here every day from now on! I went to the bathroom and changed into my boys clothes, “see you tomorrow 7 PM sharp the woman said, don’t be late! Oh and shave yourself from toes to nose, a good sissy must be smooth”. I went home, exhausted, but satisfied. Mmmm to feel this cock penetrating and pumping me full everyday, have to get used to it, but feeling as girly as I did was heaven to me.

When I started to live on my own the first thing I did was buying lingerie and a tiny dress. Mmmm at night I loved to dress in front of the mirror and then toy my boy pussy with a large dildo, while watching pictures of dark guys with big cocks.

A few months later a friend was over for a drink, I must have had too much to drink and told him about me dressing up. I’d love to see you dressed he said, go on dress as a sexy girl for me. I hesitated but went to my bedroom and returned in sexy lingerie and a short dress. My friend was sitting there with his cock in his hand, and a big cock it was! Come on, he said. I could use a good blowjob from a handsome girl like you….

-unfortunately I’ve reached the maximum no of characters now, so can’t continue my “About You”-.