crossdressingstories
patreon
Sissy Transformation
🕑 Added 2022-03-17 12:39:03 +0000 UTCMy wife is 5 years older than I am and we were married when I was just 24 years old. My wife pursued me very hard as she saw something in me she thought she could control. I was really taken by her aggressive nature and found her directness in telling me what to do exciting.
My future wife worked as a legal secretary in a large law firm and she told me when we were dating that she wanted to find a man who would be willing to stay home and keep house while she worked and supported us. She said she could see I had the potential for this kind of role and men like me were hard to find. She did everything she could to get me to say yes to marriage.
At 24 I had been a lifelong crossdresser, but I did not want my future wife to know this. Later I came to find out that she had expected this from me and that is why she wanted me so badly.
I was a virgin when I met my wife and she was very clear with me there would be no sexual relations of any kind until our wedding night. She also gave me specific directions to shave off all of my body hair before our wedding day. She told me her vagina was fully shaved and she wanted me to also be fully shaved between my legs. I really enjoyed she was taking charge so I did exactly as she asked. I got an unexpected thrill when I shaved all of my body hair off as I looked like a little boy who was going to become a mature woman's husband. Before we were married I never saw my future wife naked.
I was very excited to have my wedding night experience. I was very naive sexually and I knew my new wife would be able to direct me in making love to her. I was well aware she had experienced more than a handful of male lovers since she was ten years my senior and I wanted to do anything I could to please her. I was setting myself up to be very submissive and that is just what she wanted.
"Okay my loving husband...take off all your clothes; and I hope you did what I asked." Said my new wife on our wedding night.
"I did exactly as you asked." I said as I quickly removed all my clothes revealing my smooth hairless body to her for the very first time.
"That's a good boy! You did just as I asked. Now come over to your new bride and undress me and let's see if we can get that tiny penis of yours to get big enough to fuck your new wife."
I did as she asked and my smaller than normal cock continued to grow. I unzipped her white gown and she stepped out of it. Underneath she was wearing a very feminine white petticoat and she had on a beautiful satin and lace white bra. I very slowly began to slide her petticoat down which revealed she was wearing a large pair of full cut white "granny panties" that had tons of lace on them. Lace was on the waistband, the leg openings, and in several lines across the butt. They were very pretty rumba panties. She also had on white lace top stockings attached to a white satin and lace garter belt.
"Put your hand between my legs." She said directly.
I did this and felt the lips of her pussy and they were very puffy. The crotch of her panties was also very wet.
"Go ahead...Push your fingers against the front of my panties and feel how wet I am." She sighed.
I did this as her pussy mound felt like it was getting bigger in my fingers.
"Pull off my panties but leave my stockings and my bra on. I'm going to take my tits out of my bra cups and then tell you what to do."
I slowly pulled down her panties and revealed her fully shaved pussy lips which looked to be really puffy now and glistening with her wetness.
"Starting now I want you to call me mommy when we fuck. Do you understand?" She asked.
"Yes." I said meekly.
"Then say it; Mommy, I want to fuck you." She said in a cross way.
"Mommy, I want to fuck you." I repeated.
"That's right. And I'm going to call you little boy when I tell you how to fuck me. Do you understand?"
"Yes." I again said meekly.
"Good...Very good. Now little boy, I'm going to lay back on the bed and I want you to gently push my legs apart and put your mouth on my wet pussy and start to lick it up and down. When you feel the little button of my clit, I want you to gently flick it with your tongue and then lightly suck on it. Can you do that little boy?" She asked.
"I can do that Mommy." I said getting into the moment.
It was the first time in my life I had ever had my mouth between the legs of a naked woman. I licked the juices that kept oozing from her puffy cunt lips. I really enjoyed the taste of her love juice. Then I felt her clit begin to enlarge. I put my lips around it and sucked.
"That's a good little boy! You feel so good to mommy. Now push your tongue as deep as you can between mommy's pussy lips. Push it in deeply and get as much of my love juice in your mouth as you can." She moaned.
I did this and felt her cunt lips throbbing. I had a mouthful of her juice, so much so you could hear a slurping sound as I took it in.
"That right little boy...Now bring your full mouth up to Mommy's mouth and kiss me so I can taste my juice." She was really moaning now.
Our tongues intertwined, I felt her sucking on the juices in my mouth and I let them pour into her mouth. My penis had gotten longer and harder than I can ever remember at this point. With my mouth empty of her juices, I pulled back and asked;
"Can I fuck you now mommy? I want to see if I can ejaculate inside you. It will be my first time ever."
"Of course you can little boy. Let me feel your cock to see if it is hard enough to fuck mommy." She gasped.
I raised up as she put her hand around my erection that I was most proud about. She felt it up and down and said;
"Well, it's not the biggest mommy has ever had, but it is very hard, so 'yes', let's put you inside my pussy and see if you can cum. I'm always on birth control pills, so go ahead and see if you can squirt your sperm inside me."
She was so wet and so puffy it was very easy for me to find the opening to her vagina. I put the head of my cock at what I thought was the hole and she grabbed me and quickly guided me inside of her.
"Oh that's it little boy! You're inside mommy. Now fuck me till you cum!" She yelled.
I began moving my erect penis in and out of her cunt faster and faster. I felt a feeling I had never felt before as my cock swelled up and quickly started shooting semen and sperm into my bride.
"Oh my God...Oh my God...Oh my God!" Was all I could say. "That was wonderful!" I gasped.
While I was cumming I felt my wife's pussy lips squeezing up and down on my erect cock. Her cunt lips actually milked my cock of its semen.
"Oh baby! You really shot a huge load into mommy! You're not done yet little boy! I want you to get your penis out of me and to get your mouth back down between my legs." Ordered my wife.
"Between your legs?" I asked.
"Yes honey. You filled my cunt with your cum and it is so full some of it is coming back out. Get down there and lick up your semen. I don't want it leaking onto the bed." My wife directed.
Not really knowing what to expect I just did what she asked me to do. The slit of her pussy was very visible as my bright white cum was oozing out of the lips.
"Hurry up! Lick me clean! Get all of it; keep it in your mouth. I want to watch you swallow it." Said my wife.
I did not think, I just reacted and did as I was told to do. The sticky, white cream had a very pleasing taste to me and after slowing beginning to lick I found myself not only licking the surface of her cunt lips, I found myself plunging my tongue inside her to get as much as I could. When it appeared I had gotten all of the spunk I could see and feel I raised my head up to show my wife my mouth was full.
"That's a good little boy! Now swallow your semen so I can see you enjoy it!" My wife directed as she watched me.
The load of semen slid down my throat easier than I thought and I really enjoyed the taste which was mixed with my wife's pussy juice. This was without a doubt the most sexy and kinky sexual experience I could ever have imagined and it happened on my wedding night with my new wife. I was clearly in the role of a submissive husband.
"Did you like fucking me? Was your first time cumming inside a girl all you thought it would be?" Asked my wife.
"It was wonderful! I loved it! I can't wait to do it again! Do you think I can get you pregnant?" I asked in glee.
"Whoa...Slow down there little boy. I'm your wife and I control our sex life. I take birth control pills, and have for a long time, so I will decide where and when I try to get pregnant. And honey...I hate to be so honest on our wedding night, but...The size of your erect penis is about half of what I am used to fucking." Sighed my wife.
"But I was so turned on! I have never felt myself bigger!" I said in protest.
"I guess I'll get used to it. Now lower my bra and gently kiss, lick, and suck on my nipples as we get some sleep. You might also think about gently using your fingers on my pussy to relax me." Directed my wife.
I quickly did as she asked and her nipples were bigger than anything I had ever seen! I loved sucking on them. I slowly stroked her hairless pussy as she moaned and we both relaxed into a comfortable sleep.
On our honeymoon we engaged in sexual intercourse a minimum of three times a day. My new wife taught me how to lick her pussy. She took full control of our sex life. I followed all of her directions exactly as she instructed. I found myself enjoying being submissive to her.
When we returned home from the honeymoon, I began my agreed upon role as a "house husband." I did not mind this and my wife really got into the role of controlling our married life. Every morning she went to work and returned home around 6pm. I kept our house running and having the house to myself, I soon began indulging in a favorite activity of mine; dressing as a woman.
I was always very careful never to be dressed as a woman when my wife got home. And for three or four years this went very well. Then one day the garage door went up in the middle of the day and I was fully dressed as a girl with make-up, wigs, dress, and the whole nine yards. My wife was home at an unexpected time and I was stuck. I stood still as she entered the room and saw me.
"Oh my God. This is great. You look beautiful. You're not a "house husband" you're a "house wife." Said my wife.
"I can explain." I said quickly.
"Honey...Don't worry about it. I think you look really sexy. Lift your dress and let me see what you are wearing under it." She ordered.
I did as she asked and exposed my panties. My smaller than normal penis was fully retracted in embarrassment.
"Look at that pretty pair of panties! And the front of them is so flat. You really no how to hide your tiny penis." She said with a sneer.
"I've...I've had lots of practice." I stammered.
"Isn't mommy's pussy enough for you?" She asked.
"It is! I love to lick it. I just don't know if my penis is big enough for you." I said quickly.
"Well it isn't. And this is the perfect time for me to suggest a change." Smiled my wife.
"A change? What kind of change?" I replied.
"Let's just put an end to you and me having sexual intercourse. It really doesn't do much for me and it appears it doesn't do much for you. I'll still have you lick my pussy when I tell you to, but we just won't have any more intercourse. I can back off on my birth control pills as you won't be ejaculating inside me at all." She said in a matter of fact way.
"You mean you'll stop having sex altogether?" I asked surprised.
"...Not entirely. You would not believe how many guys at work hit on me. I've told them "no" that I am married, but it doesn't stop them from asking."
"What are you suggesting?" I asked in a cautious way.
"Maybe it's time I started saying "yes" to some of these men. I will tell them you have to be in the bedroom with us when they fuck me, but that's the only condition. What about that?"
"I don't really know what to say." I answered.
"You don't really have to say anything. I'm telling you that's how things will be going forward. It's not like you have a choice do you? And I want you to start wearing panties and a bra everyday starting now, plus every night I want you in a pretty nightgown. I assume you have that lingerie, am I right?" She sneered.
It was a little over three months before my wife told me she would be bringing home someone from her office who wanted to fuck her and who said I could watch. My wife had not allowed my penis anywhere near her vagina, but I had been told to lick and suck on her cunt at least a dozen times to help her cum. I wore a training bra and panties on a daily basis and a nylon and lace nightgown at night. My wife made me throw out all male underwear and she purchased silicone breast forms for me to attach to my hairless body so I could begin wearing a full size bra, which I did with glee.
"You are now my full-time sissy cuckold." Said my wife, "and you're going to do what I say and help me enjoy a sex life that fulfills me."
As I now lived as a girl full-time, having a man invited into our home seemed oddly natural. I was curious to see what a real male penis in full erection looked like. The man who arrived at our home at my wife's invitation was a very handsome thirty-something married co-worker of hers. His name was Greg. We had very little chit-chat and soon the three of us were in our bedroom and my wife stripped fully naked as did Greg. My wife told me to remain fully dressed.
"Sissy, will you lick my pussy and suck my clit so Greg does not have to?" Said my wife.
I climbed on the bed fully clothed in a sun dress and did as I was told. My wife's clit seemed to be larger than normal as I sucked on it and got her pussy fully drenched.
"Now Sissy, I want you to lick the head of Greg's cock and get it nice and wet for me. Do it now." She said.
I did as she asked and marveled at the size of his every expanding cock. The hole in the tip of his cock gaped open as I licked and sucked on it as if he was very close to cumming.
"That's enough Sissy. Pull Greg's cock into position in front of my pussy and when I tell you to, you help him insert his hard cock inside of my cunt. I want you to be the one who allows and helps Greg fuck me." Said my wife.
Without a word I followed her instructions and watched as I guided Greg's man-sized cock to my wife's wet pussy lips that seemed to puff out to meet and consume his penis. Greg's erection slid inside my wife with ease. I was still fully dressed as my wife and her lover were fully copulated in front of me. Greg put his mouth on my wife's lips and the two of them shared a deep tongue kiss as he began to thrust in and out of my wife's pussy. Soon, Greg grabbed her hips as he fucked her in a way I never could have imagined.
"Oh Greg! You are so big! You are a man! Not the Sissy I've been letting inside me! I want you to cum inside me and bred me with your sperm!" Gasped my wife.
Greg said nothing but began to grunt, and this time when he thrust all the way in, he stayed deeply embedded inside my wife as his body muscles convulsed sending what had to be rope after rope of semen deep inside her pussy.
"Oh that's it! I feel your hot cum inside me you are filling me up! You are a man, not a sissy!" Screamed my wife as she convulsed with her own orgasm.
I had never seen such an intensely erotic display of sexual intercourse. I felt the panties under my slip and dress become wet as pre-cum had leaked into my crotch. I felt my nipples become engorged. Watching my wife have sex with another man was very exciting!
"Sissy...get between my legs and lick off the huge excess of Greg's load." My wife ordered.
The two of them detached from each other and I immediately got between my wife's legs and began to lick her pussy taking in Greg's semen that was oozing out of her pussy lips. I enjoyed the taste of their love juices mixed together. I was still fully dressed in my full make-up and my sun dress and stockings. My breast forms were in place and by now my tiny penis had stopped its pre-cum and had retracted into my body.
""That's enough little sissy. Leave enough of Greg's sperm inside me where it belongs. Did you like watching mommy fuck a real man?"
"I must admit, it was very exciting. I also would admit I would like to have been the one shooting sperm into you, but Greg's cock is certainly very manly." I replied.
"Well your days of shooting sperm inside me are over sissy. You know that. Now I want you to go do some housework for an hour or so. Greg and I are going to cuddle here naked while we wait for him to get another erection. I told Greg he could fuck me twice tonight and I don't want to disappoint him."
"Yes, mommy. I'm your sissy and I will do what you want." Was my response.
As I was answering her, my wife and Greg faced each other lying on the bed and began a very deep tongue kiss as they tightly cuddled their bodies together. It was as if I did not exist. My wife lifted her free arm and hand and motioned for me to leave the bedroom. I did as she asked as the two lovers intertwined their naked bodies tighter than I had ever seen two people together.
"Oh Greg, it's so wonderful to finally be fucked by a real man! Your cock is so much bigger than Sissy's. I can't wait for you to get hard again." I could hear my wife moaning as I went down the hall.
I kept myself busy with some light housework, but I stayed within earshot of our bedroom as my wife and her lover made continuous moaning love sounds as it was obvious they were enjoying each other's naked bodies. This activity went on for a little over an hour and then I heard my wife's voice call out to me:
"Sissy...My little Sissy...Greg and I are ready to fuck again. Please come into the bedroom and insert his huge cock inside me again. Don't keep us waiting; I can't wait to fuck this handsome man!"
"I'll be right there." I answered as I came up the stairs and went to the bedroom door. As I entered the open door the two lovers were still in a tight embrace and looking into each other's eyes. My wife turned to me when I entered the room and said;
"Thank goodness you're here. I want you to insert Greg's cock into my pussy like you did before. And I want you to swear to me you have not ejaculated your tiny penis into your panties."
"I have not even had an erection and certainly not an ejaculation. I'm your pretty little Sissy, and my job is to make sure you can enjoy sexual intercourse with a real man." I replied.
"That's my good sissy! You are perfect! Now guide Greg's cock into my cunt!" Moaned my wife.
As I guided Greg's enormous erect cock toward my wife's pussy, her puffed up cunt lips seemed to reach out to suck in his penis. She was so wet he slid inside her easily. I watched as his huge cock completely disappeared inside her cunt.
"Oh my God! I love it when a man fucks me!" Shouted my wife as she turned to me and said; "Greg and I are going to make a baby, and after I give birth you are going to take care of the baby to give you something to do at home all day."
My wife turned back to Greg as the two of them began to engage in vigorous intercourse. Greg pushing in and out of my wife faster and faster as both of them moaned and grunted as they each came near their own climaxes. I stood next to the bed fully dressed watching it all and concentrated on not cumming a single drop in my panties.
"Greg honey, I'm really cumming!" Shouted my wife. "You are such a great fuck! Your cock is wonderful inside me! Shoot me full of your sperm and impregnate me!"
At that moment her entire body convulsed as Greg grunted loudly and slammed his cock deep inside my wife's cunt as it was obvious he was ejaculating rope after rope of his semen inside her. It was a very physical orgasm for both of them as they fell together exhausted after it was over deeply kissing each other as lovers do.
