Small cock sissy.


I turned sissy  shortly after my first wife divorced me. On and off I had a few females who took me farther than I would have ever gone on my own. Being in panties or a tight skirt was becoming normal to me since I was ordered to dress as a girl by Jo. She would not allow me to be in male cloths of any sort. She called me a sissy and sissies wear girly clothing. This all came into play when my girlfriend before Jo, cuckoled me from the start and over our four-year relation ship. During that time she had many different lovers usually two or three men a week. Sometimes I was allowed to watch other times she went to their place where a cuck could not watch.


I enjoyed being a cuckold for the first year since I always was told if I wanted her pussy I could only have it after a man had filled her first. So I always had the sloppy seconds. Believe it or not I dearly looked forward to the sloppy second from a big cock male. She was stretched out and so wet being full of another mans cum.  My little dick would slide right in with no problem and it was so slippery. It didn’t take much more than a minute or two before I would add my spunk to her overflowing pussy of cum.


When I met Jo, I had not had the first intercourse with a female in over four and a half years. I was so used to getting a pussy already used I had a hard time climaxing in her fresh pussy. So I tried to be manly and do the job but the truth was I was small and had small spurts of cum when I did cum. When the third time came to have sex, Jo asked what was wrong? I broke down and told her I was so used to sloppy seconds I had a hard time cumming in her. She added way more lube to my cock which made it a lot more like what I was used to. I still did not cum much when I did ejaculate.


Once I had told Jo how I was a cuck for the past four and a half years, she seemed to be different acting towards me. She asked if I had ever sucked a cock before? I told her I had played with another mans cock but never sucked it. She asked for the details so I told her. My other girlfriend had this guy who had a huge cock and took pleasure in fucking her as I watched. He was a regular of hers and I was ordered to take his big cock and stroke it until hard. Then it was my job to guide it in her waiting wet pussy. His cock was heavy and could only get half erect due to how thick and meaty it was . I always felt very humiliated having to jack his cock until erect than put it in her. I enjoyed seconds after him because it was like sticking my small cock into a jar of jelly.


When I told Jo about all of this she told me it was going to be the same with her. The difference was I was chastised and only let out for sloppy seconds with her. She had four sometimes five guys who bred her through out the month. I never had to play with any of the men’s cocks. I was after some time made to lick her clean after I had my sloppy seconds turn on her. The first few times was the worse but after that I became used to it. Then it came to where I was not allowed to breed with her at all. My job was to clean her and eventually clean his cock with my mouth. I never had intercourse with her again once I started cleaning her lovers cocks.  She would call me all kinds of degrading names as I ate his cum from her well used pussy, than turned my attention to his cock which I would suck hard for round two. I only was allowed to masturbate once I had cleaned both of them. When I was allowed to do so, I had to catch my own spunk and eat it as she watched.



Then we broke up and I met my wife, I thought I could be a man again. Thinking I was not going to be a sissy any more. She explained to me I will never be a man. She seen right through me and knew I was not one. She took control of me and I have been in panties ever since. Now five years into our marriage I am still a cross dressed sissy male and still cleaning cocks and my wife used pussy. The only way I get release now days is from prostate stimulation with wife’s strap on or a dildo. I am a sissy and will always be one according to my wife. I know it is the truth, I have never been a man ever. Just a small cock, sissy cuck.






My son is now my daughter.


My son Tom became a trouble maker in school. When he started to get in trouble I decided it was time I feminized him.  Since he had a small cock, pushed the thought into full gear. When the summer came, I started training him by removing all of his cloths from his room when he was sleeping. The next morning all he had left for male clothing was his tighty whities he was wearing. When he awoke he yelled “where are all my cloths #@% *)% #@” is all I heard. I figured it would be the last time I was going to listen to that kind of talk. I waited until he showed up in the kitchen where I was sitting sipping my morning coffee.

Where are all my cloths he asked as he burst into the kitchen? Well good morning to you to, I said back at him. What happened to all my cloths are you washing all of them? No I said calmly, all your cloths are in the other bedroom. He turned and headed to the spare bedroom. I got up and followed him, when he entered I closed the door behind us. I had redecorated it into a girls room.  Opening the dresser he frantically looked for his cloths but it was all female cloths in each drawer. He headed to the closet where it was full of dresses, slacks, blouses, and shoes. He asked where his cloths where? I told him these are all your new cloths. Looking confused I told Tom these are the cloths you will be wearing from now on. Ho, ha. ha. ha. he asked where are they? Like I said, these are all your new cloths. You can pick out and outfit you want to wear today. No, he said as he sat on the edge of the bed pouting.


I walked over an sat beside him on the bed. I told him since he was in trouble I decided it was time for a change. You will be a nice polite girl, I informed him. He began to cry as I continued talking. You will wear panties, camisoles, tights, dresses, and blouses just like all girls your age. I continued telling him, he will be a nice smelling sweet daughter of mine. His tears falling to his bare legs now as he started sniffling. I put my arm around him and told him it will not be as bad as you think. Trying to hold back his tears he asked, what about my friends what will they think? Well if you cooperate and try to be a nice girl we can move to where no one knows you as a boy. That will only happen if you try hard and cooperate with me. If you don’t I will see to it your friends know you’re a girl now. With that I told him to put these on, handing him some black leggings and a pink top.


He dressed and pouted the whole morning until I asked if he would rather be in diapers? I then brought up we were going to move and where would he like to live as my new daughter? He told me he would like to live in California which was all the way across the US. So when I had found a place to live in California we packed up and moved. It was a fast move, from the time he told me California and the time we made there took a mere five weeks.

During the long ride I told Tom he could let his hair and nails grow out. He was already adjusted well to wearing dresses and some light makeup. I think he was actually enjoying it once we were on the road. It seemed to me he was more worried his friends  might find out before we moved. Once settled in he was a changed person. He was asking what tops went with dresses and legging, etc…. he never complained again. Tom has become very good at makeup and clothing combinations. He picked out his own girls name, Tammy.


Now he was feeling rather confident in his looks and really looking nice. I figured I would wait a year then suggest she think about breasts. I am confident she will agree by then. I just do not want to put any more pressure on her at this time. Tammy loves to dress in reveling outfits. She is young and I am just happy she feels so comfortable to dress that way. I never would have guessed she would look as nice as she does. She even watches what she eats which surprises me for some one that young. I can tell she likes her body and that is why she likes showing it off.


One day I caught her masturbating  to her own reflection so I know it arouses her to see her self looking that pretty. When she saw me she quit and told me she needed a release. I told her she can not be doing that to her self. I will need to get her in chastity before long, I can’t allow this to continue.


I was happy she was comfortable with her self. She has even met another nice girl friend who has helped her. Tammy will be a lovely lady when she gets older. I hope she meets a man who wants more than just sex with her. I will need to sit down and have that talk with her very soon. But for now I am just happy to have a daughter who is so well receiving of her new life.







Mother-in-law encouraged me to cuckold her son on our wedding night.


When I met my boyfriend he did not seem to be the kind of macho man most guys act like. Instead he seemed more reserved and not an arrogant ass hole. In fact he was somewhat shy and I found that nice for a change compared to other guys around. We hit it off pretty well I thought and he seemed to loosen up after a while. His name is Dan and I really kind of liked him. I asked if it was okay if I called him some time and he was all smiles as he gave me his number.

A week later I called Dan and we had dated ever since then. We got along well and he really treated me nice and respectful. That was a change from other guys I dated. After several months of dating he wanted me to meet his mom “Elsa” and his dad “Garry”. We visited them on a Saturday and they seemed normal as any other parents. His dad was polite and reminded me of Dan when we first met. His mom was just as polite and made me feel welcomed. In fact his mom and I hit it off real well as she chatted up a storm with me. I found it a bit funny after we left, when Dan said his mom hogged me the whole time. I told him it was a girl thing and I said I didn’t think she hogged me at all.  I thought his parents seemed like a happily married, normal couple.


About three months after meeting them Dan and I were engaged. When his mom “Elsa” heard the news, she called me up and told me we needed to go shopping. Elsa came by at nine A.M. and picked me up. During this shopping trip Elsa told me I should seriously consider sissifying and cuckolding Dan. I was surprised and confused about what she had said. I asked her what did she mean by that and what was cuckolding? It was at that point she explained each to me so I could understand what she meant. Elsa also told me Dan knew his dad was a cuckold sissy. Elsa also asked me if I was planning to have another man consummate my marriage to her son Dan? I asked in what she mean? She flat-out asked, your planning to have another Man have sex with you on your wedding night and make Dan watch aren’t you? I told her I was not planning on anything like that. I also informed her Dan and I where deeply in love with each other.


Elsa explained my life will be a lot easier if I start out the marriage right.  If her husband doe’s not listed to what she tells him to do she beats his ass with a good old  hair brush. You need to cuckold Dan so he does not expect he is the only one who will be having sex with you. Elsa went on to say, Gerry had not had intercourse with her for  many years now. Elsa enjoys many different lovers she said, and has Garry find them for her. She gives him one week to full fill his obligation to supply a nice size cock, lover for her to have sex with. He can do what ever it takes in order to assure her lovers cock is a minimum of 8 inches long and 1-1/2 inches round or bigger. Normally Garry runs an ad to find the lager ones she explained. However it is not always easy for him to find someone so I have Bob as my regular lover. He and I have sex regularly as Garry watches us in his lingerie and chastity.


Now on your wedding night Elsa continued, Garry can find you a large cock if you like. Once you have Dan cuckolded you can have sex with who ever you choose. She even told me she would help cuckold Dan if need be. Elsa suggested I buy lingerie for Dan to wear under his suit when we get married. That will let him know you’re in charge of the marriage. This was a lot to think about I told her. Then she strongly suggested to have another man have intercourse with me on my wedding night and have Dan watch. She was very persistent about this and told me to make Dan guide the other mans cock into me.


The more I thought about it, the more appealing it became. Here I have my fiancé mother telling me how to have affairs with other men with his total knowledge. Heck she was giving me the okay to go through with it and instructions on how to do it. When the wedding day arrived, Dan was wearing lingerie under his tux. I decided to have two cocks for my wedding night to fuck me in front of my new husband while he watched. He was already sissified and now would be cuckold. That was three years ago and I like his mother, have lovers with large cocks for my sexual pleasure. My husband Danny boy finds them for me and sets everything up. Life is good and I have Danny’s mom to thank for a pleasurable life and a husband who obeys.


Happy wife.

“SM” Sissy Maker




Wife turns husband into a sissy for her amusement.


My wife of three years decided it was time to feminize me. She had been talking about it for over a year. This seemed to be something that she wanted to do quite badly. It was something sexual about it which made her hot thinking about it. Well I guess I knew what made her hot about it. She wanted to have sex with a female but have the pleasure of a cock also.


So the time came on a weekend she decided she was going to transform me. I willingly let her do it since it was a fantasy of hers. I figured what happened behind our closed doors was our business. This turned out to be what I thought was a lot of fun. I was getting sex every weekend and I didn’t mind that. We had played this way for over a year now and I was used to dressing the part. She even put makeup on me to make me look more feminine. Just like anything, after some time this become old to her also.


It took a lot of convincing on her part for me to accept another cross dresser to join us in our bedroom. I gave in and we ran an ad on Craigslist. This brought many responses, but none that where appealing to us. Then we caught a break according to my wife. We found some one who was height to weight proportionate and interested in what we were looking for. We emailed back and forth getting to know each other and eventually gave him our phone number.


We ended up meeting and he “Dan” seemed to be a perfect fit. We set up a play date and he showed up just as planed. Dan dressed once at our place and while he dressed, I also dressed.  I was so nervous I had to have my wife help me. We met in the living room and I figured we were just going to sit around, talk and maybe have a few drinks. That was after all, what we agreed to do when her and I set this up. However after a few stiff drinks which my wife had made for us. She proceeded to take charge of the situation.


She told us to take out our pricks and see who had the largest between the two of us. Who ever had the largest cock would get to have sex with her. She stood up and announced this and also said come on girls lets compare our cock’s with each other. We both got up and pulled out our cock and placed them side by side. She took Dan’s cock over mine which was close to the same size as mine. After they had sex which lasted for about an hour, it was late and Dan thanked us and left. We went to bed and I had kept drinking as they fucked so I was out like a light.


My wife and I sat down the next day and talked about the night’s play time we had with Dan. We agreed Dan made a nice enhancement to our play time. It was agreed by both of us to have him return for another play night. I asked my wife when was it decided for Dan and her to have sex? She told me, she will make the decisions when it comes to two sissies in her house. What ever she decides to do or wants to happen, Dan and I better cooperate. She continued with, if I do not agree with what she says she will expose me for the cross dressing sissy I am. With that said, I did not have anything to say. I knew she was not bluffing and would expose me if I didn’t listen. We set the next play date with Dan for the following weekend.

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When the weekend arrived, I was already dressed before Dan showed up. I greeted him at the door and he went and changed cloths. Upon his return my wife had made us drinks which we relaxed and talked some. During out talk we found out Dan was bisexual. He was completely open to trying anything my wife wished. My wife told us, she wanted to see us two girls do some hot play time with each other. This took me by surprise since we had never talked about this before. Dan took the lead and before long he was playing with me and I with him. I glanced at my wife, who I could see by her smile she approved of what was happening.


As the night continued and the drinks kept coming, things became more and more sexual.  My wife kept encouraging me to suck Dan’s cock. Dan took my cock without any hesitation. We continued to kiss and embrace each other which made me feel more comfortable. Before long I heard my wife tell me to go down on Dan’s cock. Still not wanting to I just went for it and tried not to think about it. I heard my wife say, I knew you were a cock sucker! At this point, I figured this is what she wanted me to be so I tried my best to deep throat Dan’s cock. It took some time but with my mouth and hands I managed to make Dan climax. I took his load on my face since I knew I would never be able to take his load in my mouth. My wife made the comment, there is always next time. So I know this will not be allowed when we get together again.


“SM” Sissy Maker


Cross dresser in love.


I have cross dressed for some time and gone out in public. One night when I was in the night club in which I frequented. I met a guy who I took a liking to. He was funny and made me laugh but most of all he talked to me as if I was a normal girl. Now I now he knew I was a cross dresser.


We talked most of the evening and I enjoyed his company very much. In fact I was attracted to him and I was sure he was interested in me.  When he suggested we leave and go back to his place for coffee I accepted. Once we arrived at his place I made coffee and he got more comfortable. When I brought the coffee in to him it was obvious he had more than coffee in mind.

01I wanted his cock and was not interested in coffee at that point. I decided it was time to show him what I could do to please him. “Hell I want to suck his cock so bad I told him to stand as I freed it for him” .

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I took his cock in my mouth and showed him what I could do. He moaned with pleasure as  I sucked on his cock.  He told me he wanted to have sex with me. I was all for that s I showed him what I had been hiding under my short skirt.


At that point he was going to wait any longer and he took me for his pleasure. I allowed him to do as he pleased since I was craving his cock anyway. I turned around and sat on his stiff manhood.

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He slid right in and we fucked until he was spent. Since that night we have been inseparable. I love him and he loves me. I have never been so happy and I feel secure and feminine around him.

264_1000q   Sissy Me and my boy friend.

“SM” Sissy Maker

Cross-dresser to sissy cock sucker.



I have cross dressed since a young age. I was caught by one of my girlfriends and she trans-formed me in to a cute sissy. She took me out in public which was very scary for me. I was made to dress like a slutty girl when at home.



Towards the end of our relationship she took me cross-dressed to a club. This was for me to pick up a man to have sex with. We did pick up a stud and took him back to our place. When he revealed his big cock she took over and fucked him as I watched. They kept in contact and she ended up leaving me for him.


I did enjoy being in public dressed. I have gone out on my own many times since then. I have only dated men who are interested in a cross-dresser. I have found I like sucking cock and having anal sex with men. I do not feel I am gay but more bisexual. I would even consider myself a sissy male.


Regardless I have not had sex with a female in over five years. I do not see myself ever having sex with a female again. The picture below shows you what I enjoy the most when it comes to having sex.

pussiwyllow-qs8nh-a8e22f“SM” Sissy Maker




How I turned sissy



When my girlfriend and I had a disagreement on things that work and things that don’t work. I was giving a bet by her which I accepted and I was going to become the test subject. The bet was that if I took two vitamins over a six month period, I would grow breasts. I told her I would take them and prove to her they would not work.  She told me the two to take where fenugreek and red clover. She bought them off the internet, so when they arrived I started taking them. After four months I noticed it looked like my breasts where getting bigger. I figured it was just my imagination and kept up the regiment. By the fifth month I could see I was indeed growing breasts. I stopped when I realized they where growing. They were AA when I stopped taking the vitamins. But they continued to grow until I ended up with A size breasts.


My girl friend during this whole time talked about feminizing me which I assured her that would not happen either. I was wrong, over the four to five months she slowly convinced me to try on female clothing which at the time I seen no harm in doing. By time I stopped taking the vitamins I was wearing panties. I also was getting an erection when ever I put them on. This lead to my wearing leggings and T-shirt which I found felt very nice and light to wear. She pointed out my pert nipples showing through my T-shirt. I didn’t care at the time until she talked me into going out in public dressed like that. When I got whistled from guys it made me feel funny. My girlfriend asked what I meant funny?  Do you mean funny as in sexy funny? Yes, I guess so I told her. I started wearing an A cup bra because of my new boobies.


After telling her how I felt when wearing them. She kept wanting me to dress like that all the time. I actually had to admit I kind of liked being in them. Before the year’s end she had me dressing like a girl at home all the time. I was taken into public once a month with some make-up help from her. I seen my reflection in the mirror and I didn’t know it was even me. It made me feel good and I even  looked good.  Looking back she sissified me and I took the bait.  She won and I ended up being a sissy girly boy with small tits. I know if it were not for the tits I would have not become a sissy girly boy.


Since those days I have become more girly and try to be sexy and attract guys. I have let my hair grow out and lost weight to look more sexy. Since I was no longer having any girls interested in me now that I dressed like a girl. I figures I would go all out and get guys interested in me. Yes, guys. It seems I have bisexual tendencies and I am interested in men with large cocks. Since we parted our ways I have had several men and I have enjoyed the sex I have had with them. To this day I still dress like a sissy and date men interested in sissy boys.

Sissy Boy


“SM” Sissy Maker

Sissy Dee’s Training.


Groomed all her life to be a special girl, Dee is ready to be sexually awakened, a project her father will take care of according to her mother. He shows her how to please a man orally, but when his need to breed drives him away, Dee mother is willing to join in the training to have him finish teaching her.


Ever since I can remember, my mommy dressed me up like a girl and we did all the typical little girl things like having tea parties, collecting dolls, and shopping for frilly dresses, usually in pink since it’s my favorite color in the whole world. For a long time, I assumed other families did this with their special girls. I mean I never asked anyone after all why would I? I thought it was normal, I didn’t even realize I was different from other little girls until I played doctor with a neighborhood boy.

We moved shortly after that and I pushed the information to the back of my mind. I honestly never thought anything else about it until the day I came of age, the day everything changed. Mother said, she will have daddy teach me about sex. She called daddy to the kitchen and told him I was of age to be taught about the birds and the bees.  Oh Daddy, I playfully patted his beefy arm. I know all about that.  You do he asked? Sure, when a boy loves a girl they get married and then they have babies.  But do you know how that happens he asked me? The romance novels mommy had allowed me to read never went into details on that part. There was just a lot of meaningful looks, hand holding, and passionate kisses. “More than anything, I wanted a boy to kiss me passionately”. Well mother asked, do you know about blow jobs, masturbating, and intercourse? No, I answered.  Then daddy will start teaching you tomorrow.


  I remember getting a new pink short dress with matching panties. I loved my cute pink dress, the shortness of it showed off my long legs and my matching panties. When I first started wearing it mommy told me to go show daddy how well it looked on me. I remember going into the room and he was reading the news paper. Standing in front of daddy I asked him how he liked my new out fit? When he looked at me I lifted my short hemline to show him my matching panties. Very cute daddy said, he continued to look as I twirled around in front of him. Mommy had been so proud of me being willing to wear cloths that she picked out for me.

The next day mommy said it was time for my father to teach me about sex. I know your father will do a good job with all of this, but you need to do as he says mommy told me. Despite his obvious embarrassment mommy told me he was determined to do his best for me. You’re going to do just fine daddy, I told him as I patted his arm. I didn’t want him to feel bad. You’ve always been there for me and I trust you to help me with this, I told him. Good, daddy smiled softening the tension from the lines around his mouth and eyes. Let’s go down to the basement he said. Now normally I didn’t go down there. Mommy would go down and spend time down there and sometimes daddy joined her. Daddy had spent untold weekends installing carpet and paneling and heavy wooden furniture. The basement had always been called daddy’s man cave. He retreated there when he got overwhelmed by femininity, his code for needing a break from all the girly things I did with mommy.

Still my lesson needed to be taught so I followed Daddy down the thirteen steps. Oh, you moved some furniture around since the last time I’d seen it. There was a big bench thing or what ever you call it in the middle with leather straps on it. That’s, well we’ll get to that. I couldn’t help staring at the strange rocking horse with a rubber thing rising up from the seat. The more I looked at it I realized it was a fake cock. I thought that was a weird thing to have where you sit. I started feeling weird deep inside my stomach. Not like I was going to get sick, but almost like I had to pee. Your mother like’s to ride that horse daddy said. I will conditioned or I mean educate you on that in time. You know about why mom like’s to ride it he said.

imagesVTCCZI7IWhen do we start, I was now excited to see what daddy had to teach me. I could tell he was still nervous so I walked up to him and put my arms around his neck. Then I gave him a big kiss on his lips. I continued kissing and my embracement until he responded by putting his arms around me and gently squeezed my ass as he kissed me back. When we broke our embrace I smiled and asked daddy what do you want to show me I asked? Well a man is going to want you to play with his cock and suck it. Do you think you could do that? Yes daddy, I can do that. He removed his pants and underwear standing in just a T-shirt he told me to touch his cock. I reached out and cupped his big heavy balls. Then lifted his heavy cock as it started to grow. I was watching it become erect, I was surprised how big his cock became.  Standing straight up now the big cock head was purple and bobbing as it throbbed. Go on now and suck on it he told me. I opened my mouth and put the head of his cock in my mouth. I licked it with my tung, it was so soft.

Daddy told me he wanted me to go up and down on it and try to get it down my throat. He held the back of my head and he moved his cock back and forth. That’s it he said, good job keep up the sucking he said as he stood over me. I sucked his cock the best I could. Then after several minutes he told me to stop. Removing his cock he told me to masturbate his cock.  Doing just like he showed me his cock exploded all over. Wow, so much cum, came from daddy’s cock I was impressed. I let go once it stopped ejaculating and stared at it as it continued bobbed ever so slightly. Now baby I want you to lick the tip of my cock which I did. You will need to get used to the taste of a mans cum he said. You will need to swallow it as it fills your mouth. Oh daddy, I don’t think I will like that. He told me I will get use to it and even like the taste in time. From now on I will have you eat some each time we have lessons so you become use to it he told me.

Then he said, by the end of the month I will be able to take his load in my mouth and swallow it. By the end of the month I asked? Yes, we will practice every night until you can swallow my load. He told me to play with his cock and as I did I noticed my little cock was stiff. I told daddy my pee-pee was stiff and I asked him if I needed to play with mine? He told me to remove my cloths, so I did as he said. My pee-pee standing stiff was very small compared to Daddy’s. His was a massive eight inches or more and mine was hardly an inch or two at best. When daddy looked at it he smiled and told me to sit on the table and lay back with my legs hanging off the edge. Now my pee-pee stood straight up and was really hard. Daddy lowered his mouth to it and sucked on it. The warmth of his mouth felt so good and after thirty seconds I leaked some cummies “as mommy called it” into his mouth. When he finished sucking and licking my hairless sex organ, he stood up and told me he will need to put me in chastity?  A young girl like you needs to keep her parts contained. I didn’t know what he was talking about, but then I was still trying to recover from the sucking he gave me.


The next day daddy took me to the basement again and had me remove all my clothes. My white pail hairless skin looking milky white except for my pink nipples and pink cock head. Daddy sat in a chair and told me to stand in front of him. He took some plastic tub and fitted it on my small cock and locked it with a tinny padlock. The tube felt funny and I asked what it was for? He told me so I would not get sexually aroused during training. He told me to get on my knees and play with his now exposed cock as he laid back and watched me. When it started to grow he told me to kiss it and suck on it but keep jacking it at the same time. Daddy’s cock grew very fast and once hard I sucked and licked and played with it for a long time. Daddy liked it because he kept grunting which I found funny. He kept saying I was a good girl.

He told me he was going to cum and wanted me to catch it in my hand, so I did as he asked and when it started to run out of my hand he told me to lick some up. I tried it but it was warm and slimy and tasted kind of salty. I made a funny face after my first taste and daddy told me to keep licking at it until it was gone. He watched me and kept telling me that I was such a good girl each time I swallowed some. Encouraging me to keep licking it out of my hand. Then he told me I was such a big girl when I finished it. I told daddy my cock was trying to get stiff but the plastic tub was holding it down. He told me that is what is supposed to happen.

He continued saying, Dee, you’re a sissy and sissies only get to squirt when they are being penetrated. Do you want to squirt he asked? Yes daddy my cock wants to squirt I told him. He asked me to bend over and he rubbed something slippery on my butt hole. I felt him stick a finger in me and asked how it felt. I told him it hurt and he said relax and the hurting will stop. After a minute or so he started moving it in and out which started to feel good. My pee-pee was harder now than before as it strained to get free. Soon he put another finger in side me and kept the motion going. before I knew it I was pushing back on his hand. Good Dee he said, keep humping my fingers. It feels good don’t it he asked? Yes daddy, it feels real good I told him. When we finished he told me tomorrow we will try a dildo and then a plug. I was eager to continue out sex lesions because daddy made me feel so good.

The next session daddy used a small dildo on me and I leaked just a little bit. When I was loosened up from the dildoe he fitted a plug in my ass which made me feel full. Now Dee he said, you’re doing so well I want you to give me a complete blow job and swallow all my cum. Now it will fill your mouth full but you need to swallow it as fast as you can, understand? Yes daddy, I will do my best but you have such a big load daddy. I know honey but you mother could do it and I know you want to make her happy don’t you? Yes daddy, and I want you to be proud of me also. Okay he said, then take my cock in your mouth and sick it.  This took what seemed forever but I finally felt it growing and daddy said swallow fast, as he shot the first streams of cum followed by a gush of cum. I gulped several times but there was so much it leaked out of my mouth and dripped off my chin. I could not keep up with the massive amount and pulled away. The last two streams went in my face as he finished. Good girl he told me but next time you keep your mouth on my cock until I finish. Okay daddy, I am sorry I couldn’t eat it all fast enough.


Daddy told me to keep the plug in my rear so I get what he called “Conditioned”. I asked what was I conditioning for? Some day you will meet a nice man who will be interested in you and he will want to have sex with you. He will want to put his cock in your ass and have sex with you. You need your ass stretched so you can accommodate his cock. I asked how big will I need it stretched? He told me when I can take a dildo and it don’t hurt much, then I will be ready.

I asked daddy why my pee-pee was so small? He told me there are men and then there are boys who grow up to become men. Just like their are women and girls  that grow up to become women. You Dee are what we refer to as a girly-boy or better known as a sissy. Sissies he told me, are boys that should have been a girl and that is why your mother raised you as a girl. You will hopefully meet a nice man and marry him some day. I told daddy I would really like that. He smiled and we continued my training.

About a month and a half passed before I was able to eat daddy’s load of cum. I also had mommy show me how to ride the rocking horse with the dildo. Mommy showed me how it went into her pussy and she would rock back and forth. She would keep rocking until she started to shake and saying O-my, O-my, until she had what she called an orgasm. Then she would sit still until she was ready to get off the rocking horse. She would wipe all the water off since it became wet from her. I think she must have wet herself while riding it. Then it was my turn to rid it but the dildo went in my ass since that was my only hole. Mommy told me men will want to mount my ass when I date them. I asked why and she said that is what boys do when you find one you really care about.

Mommy told me after I have ridden the rocking horse for a month or more, daddy would show you how a boy will mount you. When that day came daddy strapped me down on the table with my ass in the air. I asked why I had to be strapped down. Mommy told me so I would not try to get away.  I still didn’t understand what she meant.  She watched as Daddy smeared lube on my hole then he lubed his cock. That is when mommy told him to go slow and I knew what he was going to do. I asked mommy, is daddy going to mount me? Yes sweetie she said, just relax and he will enter you. Just then I felt pressure being applied to my rear hole and something slipped in. His cock slowly slid in as I felt my ass stretch wider than it ever had before. I told mommy it was hurting and to tell daddy to stop, but she told me to relax and take his whole shaft.

sexy_sissy_trap_sucks_not_daddy-4_tmbI started to cry as he kept pushing it in farther and farther until it felt like it was inside my belly. Their daddy said I am all the way in and he stopped pushing as I adjusted to his big cock.  We stayed that way for a minutes or two then he pulled out some and pushed back in. He did this slowly for a while then picked up the rhythm. He kept on for some time in which I started to enjoy the feeling. I started moaning and mommy said, that’s it honey just enjoy daddy riding you. It feels good doesn’t it he asked? Yes, oh, oh yes, I answered,. Then I felt myself squirt at the same time daddy climaxed inside me. I felt his big cock pumping cum in me time and time again until daddy stopped moving. Mommy told me I did real well and daddy will be making you squirt many more times.


While I laid there strapped down catching my breath daddy pulled his cock out and mommy plugged my ass with a large plug right away. I yelled as she forced it in me. Then she asked daddy, how was she tight?  Yes daddy said, she will stretch out after  several more fucking’s. Mommy told him to make sure he plugs me after each time he fuck me to ensure I stretch properly. Then mommy came and unfastened the straps. Oh I squealed as I tried to get up. Mommy asked what was wrong and I told her my ass was so full I could hardly stand straight. I was told I had to keep the plug in for and hour. She told me I should lay down and rest while the dildo loosens me up some. When it was removed it hurt but then a lot of daddy’s cum ran out of me when I stood up. Mommy old me to go take a shower which I did. I had a hard time walking after daddy mounted me.

My training went on for several more months. Riding the dildo rocking horse and sucking daddy’s cock and swallowing all his cum. My pee-pee was locked up all the time but I would squirt when riding the horse and when daddy fucked me. I didn’t need to be strapped down any more I would sit on daddy’s cock as he sat in a chair. I would ride it like the rocking horse until I squirted which didn’t take long. Daddy would make me stay seated on his cock until he climaxed in me. When I bent over daddy could slide his cock right in me and it barely hurt at all. Daddy told mommy I was ready to date which made me happy.

ab631736d4c4bbd24dd328bd3b22b02d--sissy-boys-ladyboySissy Dee

“SM” Sissy Maker



Husband shares ladyboy wife.



I am Kathoey or as say in USA “ladyboy” from Thailand. They say 1 in 15 males are ladyboys. Some say much more but no one knows. Some say we are ill in head why we take drugs and have implants to be girl. Some even have surgery to look more girl. Many have average to small penis. Some are doing because economical reason. Some parents think a ladyboy son could bring in a little income , even a GOOD one if he become top ladyboy.  

1475506895_3931_hidefporn_wsSome of us just “born to be “ woman, even though they was born as a man but inside of their heart they think of themselves as the pretty girl . They like to put make up on and wear beautiful dresses. I do same and look very nice girl. I meet man who like me. This man want to make me wife of his. We both have sex with each other.


I now am wife to man but he has other idea. Now husband and wife he let man friends play sex with me. I am used for they joy and have many men lover daily. Husband say this is why he marry me to make money. I am now sex whore he say. I have sex all day and more men come to try me. Husband is happy and I do as I told. Husband also like me to make sex with him still.


I taken care of husband is good to me. I happy to be sex for husband and he happy me with sex. Now have money and live nice.


Pretty Ladyboy

“SM” Sissy Maker




Wife and I share lovers.



I have been a cross dresser for a long time. When I met my wife I told her about my sissy side. She did not believe me until I showed her. We ended up marring some time later but I always seemed inadequate to full fill her sexual needs.  While I cross dressed at home on weekends I would convince her she need a real man with a bigger cock than mine to please her. She was more than willing to try a real man and I wanted to watch her being fucked with a big cock. I especially enjoyed seeing a large cock go in and out of her pussy until it unloaded and filled her pussy. I would masturbate to the sight until I shot my load.


After watching many real men fuck my wife she became board with it and asked for multiple men to please her sexual apatite. I agreed and again enjoyed seeing two or three men fill each of her holes while I jerked off and shot my load. This continued for a long time and she was very happy and a cores I was too.


One day she told me I would look better with some makeup and I could probably be passable. She did my makeup one day and I was so surprised at how well I looked. I asked if it was alright for to go out in public cross dressed. I felt pretty and very excited as we walked to a club.  She took me on my birthday to a gay club. I did not get much looks from anyone other than a few girls. This was alright with me since I did not want to bring any attention to myself.


Then it happened, she wanted me to have a sex partner. I did not want to have one but she was persistent about it. Wen we were out and I was dressed like a girl she told me tonight would be a good night for me to meet some one for sex. I asked her which girl did she have in mind? She laughed in my face, than told me not a girl a man silly. You need to become a full sissy girl and have a man for a night. Now I was afraid thinking I would have to be with a man. I had thought about it several times in the past but did not really want to go through with it.


She found a guy showing interest in me and after some drinks she asked if he was interested in spending the night with me? Shure he said and we left to get a room. I had butterflies in my stomach knowing what was going to take place. My wife was all smiles and giggles telling me how she wanted to see me with a man and watch like I do. She got her wish as she watched me take my first cock in my ass until he climaxed in me. It made me feel more confident in myself. We go out together now looking for men, me dressed like a girl. Sometimes we each get a man and other times we share the man.

Sissy husband


“SM” Sissy Maker