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A Sissyboi For More Years Than You Know

"I Loved My Mother's Clothes, John/Jessica"

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This is the story of my life and marriage to my beloved Samantha.

I will forever be in love with my darling Sammy, a love so deep that I had to let her go. It broke my heart and hers as she watched me that day with my girly clothes in my bags as I walked out of her life, leaving her and our twin children. They're not mine because we could not have children due to my very low sperm count. I accepted another man's children. Who is he? I have no idea to this day.

I am thirty-five years old now, and as I write this story, I am plugged and caged. A transsexual, I divorced my first and forever love six years ago. Samantha, my beloved, has remarried.

Edward is my new love and my husband.

I have always enjoyed dressing in women’s clothes ever since that day as a boy when I found my mother's silky soft panties rummaging through her underwear drawer or in the washing basket when she was out. (I will expand on this later; but first, my darling Mother Sophia.)

My Mother was a raven-haired beauty with alabaster skin so white it was like marble. Her breasts were 36C with dark areola and large long thick nipples. She was slim, almost too thin, but her bottom was tight and firm and her pussy had soft black hair cut into the shape of a heart and blood-red lips protruding out from her bush. How do I know what my mother looked like so intimately, I hear you ask?

I peeked at her. Yes, I peeked at my mother like so many boys my age. My Mother was my first glimpse of womanhood as a 16 year old I was feeling the full flush of adolescence.

Yet, always after football practice in the showers, I looked at the other boys with their big long cocks and thick crops of pubic hair, then looked at my own. I became only too aware I was not built the same. It was as if my pubic hair never grew, or my penis for that matter. Boys can be so very nasty to each other, and the boys at my school were no different. Sissyboi, little cock, girly boy, tiny cock — all the words were said to me.

At parent evenings as i began my 6th form A levels, my Mother would walk with me alongside her. I would hear the boys muttering. “Wish she was my mom.” “Oh my word, your mother is a MILF.” “She’s a hot, sexy woman.”

My father was a good and kind man who was always talking to me. We used to do our trainspotting together, spending hours jotting down their numbers and taking Polaroids of engines passing by. My mother said it was good to have a hobby because it got me out of the house for a few hours and out from under her feet.

Strangely, Mother was always dressed in just a silk robe and was always naked under it. She called it her relaxing time. My father was always seemingly very excited to return home to Mother, and I was always shooed off to bed early on those evenings.

It was one of those evenings when I was in my PJs and I was awoken. My parent’s bed was creaking wildly, and I could hear my mother whispering to my father. Since their bedroom door was not fully closed, I put my ear to the open door.

My mother whispered huskily. “Johnathan, Dunstan parked his car on our drive today. He walked up to the house, bold as brass, and, without knocking, walked straight in. What are you doing, Dunstan? I said. He said he was now the man of this house and wouldn’t knock on the door when he came here to fuck his woman. ‘Come here woman,’ he said. I got up off the sofa and we kissed in front of the patio doors as he stripped me down to my pink panties for you know who to see.”

“But my darling wife,” my father said. “I know that excites you so very much, being watched by him.”

“He pulled my shaking hand down to stroke his huge cock through his trousers. I was trembling as he pushed me down on my knees and had me unbuckle his trousers. Oh, Johnathan, his cock just fell out in front of me. It hit my nose as it sprang out.”

“But Sophia, I know about your utter submission to him and his black cock. It excites you so very much.

“I can’t hide anything from you, my love, my wise and loving husband. Johnathan, I worshiped his big black throbbing cock with my lips, mouth, and tongue. He made me swallow his whole nine inches down my throat while on my knees dear, to the very root, and lick his shaven balls, too, while his long fingers pulled and pinched my thick hard nipples.

“Dunstan picked me up and laid me over your leather chair, the one that you usually sit on, and watch his black cock ravage my married white pussy. He hooked my legs over the arms of your armchair and fucked my wet pussy, making me cum and squirt all over the leather. Dunstan said you could lick it clean when you got up for breakfast.

“After fucking your wife in your chair, he carried me to our marriage bed where he ravaged my body over and over for two whole hours. I screamed with wonderful orgasms, and to my shame, he turned me on to all fours and plundered my asshole. He took the cherry of my anus.”

“Sophia my love,” my father said. “You have no shame left after you fucked him in front of his friends. You sucked and wanked their big black cocks until they came all over your face and naked breasts. I know, Sophia, because I picked you up outside his house and witnessed the state you were in when got into the car.”

“But Johnathan, my love,” my mother said. “It didn’t stop you from licking all their cum off my breasts and neck and face at home in our bed.”

“That was to my everlasting shame. My manhood was taken from me by you, my darling wife. That’s where your total domination of my life and sex life started.”

“Oh, don't give me that. You knew exactly what life you were descending into when we met Dunstan. I told him I would not have you disrespected. You are the love of my life, the man who gave me our son. Dunstan held my hand and told me he could give me a black baby, too. I looked at him and told him I needed more cock than you could give me. That I needed domination by a huge black cock and that he gave me that. Not babies. You know this, Johnathan.

“But I have to tell you, my love, that Dunstan has taken and fucked my anus hard. I never knew I could have an anal orgasm, but I did. I begged him for more and more sex. He even said he might bring another black man, a friend of his, to use my mouth, pussy, and anus.”

“Sophia, is that something that you wish to explore, to even have happen?”

“I know I’ve become his white sex slave and, yes, I’d like another big black man fucking me. Dunstan came in my ass twice, filling it up with his seed, and then he pugged my anus. For you. Just for you, my husband. He told me to tell you he left you a surprise gift in my asshole for you, my cuckold husband, to lick and suck clean after he left me.

“But first, darling, will you lick my pussy clean? Will you lick all his black seed from my pussy? You're such a wonderful cunt licker. Oh yes, darling, that's it, sink your tongue deeper, suck his seed out of my body… yes, deeper. Oh my god, you're wonderful… I’m coming, baby… I’m coming!”

It was so erotic listening to my mother whispering dirty, thrilling my father, teasing him, with the words of utter submission to her black lover's cock that afternoon, and how his very large black cock had fucked her deeper than father ever could hope to with his tiny cock.

She bragged about how Dunstan had given her six orgasms, how she had sucked his nine-inch cock to the root, and how Dunstan had ravaged her anus. What's more, I could hear my father moaning and slurping on her well-used pussy.

Mother moaned, “Yes, yes darling. He’s twice the man you are. He ravaged my body all afternoon, and when I lay weak and my body broken from my orgasms, he plugged my asshole for your delight.

It was then I heard my mother moan my father's name. “Johnathan, your slutty wife is coming again, baby.” Her orgasm was huge. She shook and quivered with the strength of it.

I finally dared to push my head around the door, and what a sight confronted me. There was my beautiful Mother, lit in the soft glow of the lamp next to their bed, tied to the bedstead. Her arms were above her head and her head hung low with her long black hair stuck on her sweating body over her face and breasts. Her long legs were pulled wide open, up, and back, and her bottom was raised on two pillows. Her beautiful pussy was wide open, and she had a round black plug in her anus. Father was sitting on the side of the bed slowly fucking Mother with a big black dildo/vibrator that gently hummed away. Her nipples were clamped by two big clips with a chain between them, making her nipples stick out.

Mother was rolling her head from side to side and gasping. “Yes, yes, punish me. I’m a dirty whore for huge black cocks. Dunstan says he’s going to shave my pussy next week for you to lick clean more easily, darling.

I heard my father grunt his approval. I watched, feeling somewhat like a peeping tom. I felt dirty, and yet I was strangely drawn to the scene that was unfolding before me. And yes, I was very sexually excited by the sight, sounds, and smell of the room. I watched as again my father pulled the chain connecting her nipple clamps and fucked her with that long and fat black buzzing vibrator.

I heard my father gasp. “Yes, you're a whore, but your my beautiful whore, my lovely sexy wife.”

I watched as my mother's head rolled back and a huge smile and gentle moan came from her lips. Father pulled my mother by her hips down the bed as far as her tied-up body would allow. Then he tilted her hips upwards.

My mother gasped. “Yes, Johnathan, yes,” as he gently and carefully removed the butt plug.

Mother gasped throatily. “Suck the plug clean, my husband. Please let me see you lick and suck it clean.”

Mother watched my father intently as he gently removed the anal plug, held it up for Mother to see. He licked it clean and then pushed it entirely into his mouth.

I heard my mother gasp. “Oh yes. Oh yes.”

I watched Mother quiver as she watched my father lick the metal butt plug, then slowly suck it between his lips, twisting and cleaning it with his tongue and lips.

“Oh my,” my father said. “The plug has got hot being inside your ass, darling.” He finished sucking the plug clean and threw it aside.

A blob of spunk hung from my mother's anus. I watched my Father lower his head to her wide-open anus. I could hear wet slurps and gentle sucking and my father moaning in utter bliss as he devoured the contents of her filled anus. I witnessed my dear Mother convulsing through yet another bone-crushing orgasm.

My father wiped his mouth with the back of his hand. “That was delicious, you filthy bitch.” He picked up the butt plug, and with a grunt from my mother, fitted it in her anus.

I heard my father whisper. “That will make your pussy tighter for my cock when I reclaim you, my beautiful wife.” He then climbed over my mother and pulled the rope that held her tightly, freeing her arms. She then pushed his hard throbbing cock into her wet dripping cunt.

My mother sobbed and cried. “Yes, my dear gentle husband. Claim me back as your loving wife. I am yours. Fuck me hard. Take back what is yours by right.”

I watched as she pulled him into her open used cunt and held him with such sweet love. “Oh. I love you my darling,” she said.

As they fucked like two rutting animals, I slipped out of their bedroom and shut the door silently behind me without them knowing their shocked son had just witnessed their sexual debauchery.

Looking down at my PJs, I was shocked that my little cock was no longer little. It was hard, sticking out the open flys of my PJs, and dribbling pre-cum everywhere. I tiptoed to my room. I slipped quietly into bed and rubbed my little cock to its completion. I came in my PJs and fell fast asleep rubbing my cum into my tummy.

The next morning I got out of bed, put my dressing gown on, and went down for my breakfast. Mother was aglow. Gone was that submissive sexual woman of last night and in her place was my caring and beautiful mother.

“Here is my little man,” Mother said. “Good morning to you.”

“Morning to you, Mother dear,” I said. “Where is Dad?”

“He’s gone to work this morning. Why?”

“I was going to ask if I could go trainspotting again with him.”

“Not today,” Mother said. “I have a few errands to run and you can look after the house. I won't be long, dear.”

“Okay, Mother.”

“Don't forget to bathe. You’re beginning to smell so manly you can be so earthy sometimes. And clean your teeth, too. I’ll see you in an hour or so, baby.” Looking beautiful once again, she jumped in her Mini and she was off to Tescos.

I walked into the bathroom where I removed my PJs. Gosh, I thought, they’re a mess after last night's fun. I don't remember ever coming that much.

I ran a bath, dropped in a few of Mother’s scented crystals, and jumped in. I smelled nice when I got out. I dried myself off and went to put my PJs in the laundry basket, and that's when I saw them, my mother's pink silk panties from yesterday.

My hand went into the basket. My fingers caressed her pink silk underwear, then pulled them out. Oh, how I shivered when the silk brushed my hand. They were beautiful and their smell and the color were intoxicating, I held them up and ran my fingers over the still very wet sticky gusset. Not for the first time, I pressed my nose into the soft silk and inhaled. Oh my god, there was a mixture of her perfume, her womanly scents, and something else, something I had smelled many times before.

I picked up my PJs and sniffed the crotch. Yes, it was the same smell. It was a man's spunk in the gusset of my mother’s panties. My cock sprang up hard and throbbed as it leaked copious amounts of clear liquid.

An all-consuming urge came over me. So urgent, I just had to do it. It was a need I had felt many times before. I just had to do it. I had to taste the wetness on that gusset.

I licked the cum-filled gusset and tasted my Mother's cum juices mixed with her black lover's spunk. I was quivering my cock was throbbing so hard, and my pre-cum was hanging down from my cock and dripping into a puddle on the bathroom floor. I knew what I had to do next. I slipped those dirty, soft, and beautiful panties over my feet, up my somewhat hairless legs, and over my throbbing and dripping hairless cock.

I cried and moaned with a lust that shook me to my core. Feeling those silk panties against my cock and balls, without doing a thing, without touching myself, I exploded in a huge orgasm like I had never felt before. It left me breathless and gasping for air, my head spinning like a top, and my heart banging like a kettle drum. My legs shook and trembled, and I heard a wail of bliss in the bathroom. It was a wail coming from my lips, a cry from my mouth, so high pitched it could have been a woman's cry, a cry of sheer pleasure and orgasmic joy.

My cock burst forth with a torrent of spunk that oozed through the silk itself. I fell to my knees as jet after jet of thick white spunk filled my Mother's silky pink panties as my shaking hand rubbed the softness of her panties around my throbbing cock and balls. I knelt there exhausted with my head spinning and my breathing labored. Yet my little cock was still painfully hard, in all its full glory, and I was ready to come again.

I rubbed my cock and balls through my Mother's silky pink panties. My hips gently rocked as I worked that silk over my sticky wet cock. My finger slipped under the elastic and found its way to my anus, and, with all that wetness, I gently ran the tip of my finger around my anus and then pushed it gently inside of me. I moaned and my cock throbbed again with pleasure. Again and again, I pushed my finger deeper and deeper inside my bottom.

I thought of that huge black cock gently fucking my anus as I rubbed my panty-covered cock. The sublime feeling of that silk against my cock made me breathless, and I suddenly orgasmed. My body quivered, my hips thrust, and my spunk jetted out of my cock and flooded my Mother’s pink panties again.

For a while, I lay on that cold bathroom floor shaking from my thunderous orgasm. Slowly coming around, I sat up and gathered my thoughts. I wondered if I had time to slip on my mother's nylon black stockings which I had worn many times, too. Slipping my hand into the basket, I found my prize, pulled them out, and sniffed the crusted white tops of her stockings. I knew that was his and her cum juices that had run out of her pussy and down her thighs.

A car horn sounded as it passed by the house. What time was it? How long had I been there? I reluctantly pulled my Mother's beautiful pink silk panties down and off my legs. Only when I heard her car pull up on the drive did I notice I had almost ruined them, so much of my cum had drenched the silk.

I thrust her panties and stockings, along with my PJs, into the laundry basket along. I washed my cock, balls, and legs in the bath and pulled the plug out. I wrapped a towel around me and sprayed my deodorant around the bathroom which reeked of my spunk and over my body. I walked out as if nothing had happened. As I dressed and felt the effects of my beautiful wanking marathon, I looked out my bedroom window.

My mother waved. “Come on, lazy bones. Help me get the shopping in.”

I dashed out to pick up three bags

“John,” my mother said. “You have nothing on your feet.”

I ran into the house with the three bags, put them in the kitchen, and took the next three from Mother's hands. “Okay, mum.”

“You smell nice,” she said. “Did you use some of my crystals in your bath?”

“Yes, Mother. I did.”

“Don't you think it’s a little girly for a for a 17 teen year old man?”

“No, Mother. I rather like the smell.”

“I like that smell on you, too.”

“I’m going out with Paul my best friend. We’re going shopping for some jeans.”

“Okay, John, but don't be late for dinner.”

When I returned a few hours later, Mother was sitting in her chair. “Hi, Mother. What's for dinner tonight?”

“Spag bol. John, can you come here please? I want to ask a question, and I require the truth.”

“Of course, Mother. What is it?”

Mother pulled a plastic bag from behind her back. “Can you tell me what happened to these? I only put them in the wash this morning.”

I was busted! I went white and my breathing came short and fast as I started hyperventilating.

“Sit down, John,” Mother said. “Here’s your puffer. Take it easy.”

I took two large puffs of my inhaler.

“John, what have you done to my panties?”

“Uh … well … I can explain. Oh, Mother, I am so sorry”

“How long have you been using my panties?”

“For a few years now.”

“Do you like wearing my soft silk panties?”

“Yes, Mother. I am so sorry. I … I …

“There is nothing to be ashamed about, sweetheart. A lot of men enjoy the soft feeling of ladies' undergarments. It would seem you got rather over-excited?”

“Yes, Mother. I did.”

“Well, I don't want any dirty little secrets between you and me. There are enough of those in this house as it is.”

Before I could ask about the secrets, Mother spoke again.

“Is it just panties,” she said. “Or is it stockings and suspenders, or any of my dresses, slips, and bras, too?”

“I am afraid, Mother, it's all your clothes.”

“Okay, John. I have put out a few items for you to try on in the privacy of your room, dear. Old clothes I no longer use. But please don't ruin my best underwear again.”

“No, Mother,” I said. “I am so sorry.”

I dashed up to my room, threw my jeans on the bed, and looked at what Mother had put on my pillows. There was a black silk nightie, matching silk panties, and two pairs of red silk panties. With them was a note: “Put one of the red ones on now and come down and show me how your jeans fit.”

I stripped, threw my cotton boxers aside, and slowly pulled the red silk panties up my legs. Oh my word, it was just as thrilling as it was this morning. Encased in those red silk pantie, my poor abused cock became hard in an instant. I pulled on my jeans and ran down the stairs.

My cock was straining to get out,

Surprised, Mother gasped. “That was quick, honey. The jeans fit nicely. How do your new panties feel?”

“Oh, Mother. They are beautiful”

“Is it girly clothes you enjoy wearing?”

“Yes, Mother.”

“I think you are something of a sissyboi. Well, there is a site on the computer for girls like you. It’s called Train Your Sissyboi, right?”

Sitting side by side, we opened the site on her laptop.

“Look at how smooth she is,” Mother said. “John, you need to shave your legs and use the cream I set aside for your pubic hair, too,

“Can you help me, Mother?”

“No, no. John I can’t do that, but I can help with your clothes and makeup if you wish, and your hair.”

“Yes, Mother dear.”

“Now, you study what's going on here and we’ll talk again very soon.”

My mind was in turmoil and my cock was hard, I watched the site as it explained about a sissyboi. It explained how she was to be feminized and caged. Her tiny little cock was called a clitty. A sissyboi craved to suck cock after cock until her face and lips were covered in thick white cum and her eyes glazed over with lust. It explained how his boi pussy should be trained with anal butt plugs that grow in size to open their anus for real man-sized cocks.

I sat watching a beautiful sissyboi on her knees sucking cock after cock imagining it was me lusting after every cock and licking up every heavy load of cum given to her as her prize. It was then it happened. My cock exploded yet again without me touching it too much. My mother entered the room just as I had that earth-shattering orgasm.

“John,” she said, my gasps having given me away. “Did you get very excited again?”

“Oh, Mother,” I said. “I am so sorry but I had an accident.”

“Don't worry. Young men like you have them all the time when they get excited. That site must have been very exciting.”

I stood up from the chair.

Mother said, “Oh, John, you must take your jeans off. You’re staining them. Remove them and give me your panties. I’ll pop them in the wash with my pink one. Quickly!”

Mother left the room and ran upstairs, returning with a towel, flannel, soap, and a bowl of warm water.

My jeans were off and my red silk panties were wet with a huge wet spot.

She looked up at me. “My word, you did make a big mess just like this morning. Standing on the towel. I gently wiped the spunk from my tummy and my little cock and balls with the lathered-up flannel.

Mother left me to it as she put my silk pantues in the washer

“You don't have a lot of hair down there for a youth of your age.”

“It didn’t grow, along with my underdeveloped penis.”

“Well, not all men can have the blessing of a huge penis. It takes all sorts in this life, dear.”

“can you dry yourself,” Mother said. “Here is a clean pair of panties, the other pair I left out for you, and I have some panty pads to soak up the wetness from your dripping clitty. You don't need any more wet marks in your panties.”

Monday I had been home all day when Mother came to me.

“did you shave today?” she said. “I know you used the razor to shave your legs. Did you do the other parts around your penis and your testicles?”

“Yes, Mother dear. I did.”

“I have something for you. Catherine's mother asked me to take some old clothes to help the pensioners shop, but I thought of you, so I gave a donation and kept her clothes for you.” She unwrapped the parcel. There were bras, silk blouses, pretty thigh-length skirts, and dresses.

“Go try them on,” she said. “I also put out a clean pair of black silk panties along with silk black stockings and suspenders, too.”

“Oh, mother,” I said. “Why are you doing this for me?”

She looked deeply into my eyes and her hand went to my face. “I have seen you growing up and you are more a girl than a boy. I have seen you struggling with the way you are developing into a man, and I want only the best for you my darling son. I’ve seen that tiny penis you have. What do the sissybois call it?”

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“A clitty, Mother.”

“Yes, that's it. A clitty. Is it okay that I help you, son?”

“Oh yes, Mother. With all my heart, yes.”

“Good. That settles it. Let's go to your room and get you dressed up as you should be.”

I opened the door to my room and found two pairs of clean red silk panties, a pair of black silk panties, a black suspender belt, black silk stockings, and a black lace bra. I slipped out my man clothes and turned away from my mother as I pulled my black panties over my hardening cock.

“That's better without those tufts of hair,” Mother said. “It looked silly.”

“Mother, I look so beautiful now.”

She dressed me piece by piece. “You’ll need to push your clitty between your legs, dear, or it will show sticking out in front of your dress.” she showed me how to dress and slip my silk stockings over my legs and hook them to the suspenders. My bare soft smooth thighs felt wonderful.

The silk was making me shiver with lust. Then that little black dress was put over my head and a black wig was attached to my short hair. Mother did my makeup, eyeliner, and lipstick. Then she did my hair and slipped high heels on my feet.

Mother stepped back. “Well, John, you are beautiful. Look in the mirror, dear.”

I turned and looked in the mirror. Oh my god! It was a girl looking back at me. I turned away and turned back. It was me as a woman.

“Oh Mother,” I cried. “I am a woman.” I knew right then I was that person in the mirror. I was a woman.

“What name do you wish to be called by now, John?” Mother said.

“It has to be Jessica. Yes. Jessica, Mother.”

“How does it feel, Jessica dear?”

“It's wonderful… breathtaking!”

“Well, Jessica, we can go shopping together once you have learned to walk In those heels.”

The weeks passed by and my 18 birthday arrived and went, bit by bit, I slipped into the persona of Jessica at home but still dressed as a male to go to my sixth-form lessons. My A levels were due and university beckoned.

Summer arrived, and my Mother had taught me well. One day we went shopping and Mother brought me some new clothes, including new silk undies, a very pretty summer dress, and matching sandals.

As we were walking home laden with many bags, Mr. Davison popped up. A very tall, very fit, and strong man, he lived at the back of our house. His house overlooked my bedroom, my mother’s room, our backroom, and kitchen,

He looked up from working in his beautiful front garden. “Hello, Mrs, Glover. How are you today?”

“I am well. Thank you, Mr. Davison.”

“And who do we have here?” he asked.

“It’s my niece, Jessica.”

“Hello, Mr. Davison,” I said in my most feminine voice.

“Call me Frank,” he said.

“Hello, Frank,” I replied.

“Well hello, Jessica. Is this a girls’ day out shopping?”

“Yes,” Mother said.

“If you do not mind me saying so, ladies, you both look very beautiful today in the sunshine.” He put his hand out and shook Mother’s hand and put his hand out to me. He kissed the back of my hand.

“Such a beautiful young lady,” he said. “I do hope to see more of you both very soon. Oh, Mrs. Glover, will I be seeing you at the same time this week?”

“Yes, Frank,” Mother said. “Goodbye.”

“Goodbye,” Frank said.

I looked at Mother as we went on our way. She looked at me, and before I could ask the question, she laughed. “It would seem you have stolen your first heart, Jessica.”

I looked back to see Frank watching us intently as we turned the corner for home.

A few days later I got my A-level results. I had passed with straight A’s, so I dropped everything and ran home clutching my exam results. As I passed Mr. Davison's house, he was in his garden weeding the borders.

“Hello, John,” he said.

“Hello, Mr. Davison.”

“Oh come now,” he said as a large smile passed across his face. “I thought you were going to call me Frank from now on? I think I like Jessica better than John. You are so much prettier as Jessica. I’ve watched you, John. Yes. I have witnessed you blossom as you have dressed up and slowly become Jessica in the last 12 months. I’ve watched you all these years. Your mother more so, Jessica, with her black lover when he comes over. And your father watching while her body is ravaged by a huge black cock. You are an interesting family.”

“But,” I stammered. “But how do you know?”

“It does not matter how, young Jessica, just that I do know. So, would you like to pop over this afternoon as Jessica? We could have a cup of tea and a little chat about you and how I can help you to become a better Jessica because every sissygurl needs a Daddy.”

I got home just as Mother was going out and told her of my results. She was excited and she kissed me. “Well done, darling,” she said.

I told her I was going out dressed as Jessica this afternoon.

“Okay,” she said. “But please be careful, dear.”

“I will Mother.”

I had a hot bath, shaved my legs, and used the hair remover Veet on my cock, balls, and around my asshole so everything was so smooth. I even used the shower hose up my bottom to clean myself out. I had not abandoned my studies of what a sissyboi should do, and I took notice of what a sissyboi must do to keep herself clean.

I dressed in my best panties and bra with my silicone breasts, a little skirt with a blouse, and my best silk stockings and suspenders. I went around to Mr. Davison's house and knocked on the door.

Mr. Davison opened the door in his shorts and t-shirt. “Please come in, Jessica. Welcome to my home. You’re such a pretty girl, aren’t you?”

As I walked into the back room, I looked at the TV and there I was. It was me on the TV, dressing in my bedroom. A camera was watching me dress, watching me touch myself, and, oh my god, watching my mother slip my black silk panties on me.

“Yes, Jessica,” Mr. Davison said. “I see all that goes on over there.”

Then the scene cut away from me and there was my mother with a black man. It must have been Dunstan, and only a few weeks ago, as he slowly stripped her naked. My Mother looked right into the lens as she knelt on the carpet and pulled Dunstan's trousers down and off his feet. Dunstan gripped her hair in his fist and pulled her head back. I watched as she ran her tongue around her ruby-red lips as he slowly fed his cock into her mouth. Soon she was sucking his huge black cock to the root.

Then the lens zoomed in to witness my Mother’s mouth devour his cock. Her tongue slipped out her mouth and licked his big dripping mushroom head as she worshipped his black cock. Lower and lower she bobbed her head up and down that saliva-dripping cock until eventually, she had him lodged in her throat. Her tongue flicked out to pay homage to his big fat balls.

Dunstan picked her up and threw her on the futon like a rag doll. Her legs opened wide, showing her fat red labia and how wet, hot, and horny she was. Frank had caught every look of ecstasy on my Mother's face as Dunstan fucked her smooth-shaven pussy and her anus. There was no sound, but I could see Mother's cries of ecstasy and her orgasms as she arched her back and pulled Dustan in between her legs.

Then the camera focused on a chair and there was my naked, cock-caged father watching every erotic move that Mother and Dunstan did together. I could even see Mother calling him over to clean her pussy and asshole, and then Dunstan commanding him to kneel and suck his cock clean. Dunstan used my Mother again and left her passed out on the bed, and made my father suck him again. He then dressed and left as my father licked Mother clean of his seed again. My mother hugged and kissed my father and then let him reclaim her body.

I was gasping. “Frank… have you, you know… have you…”

“Are you asking if I have fucked your mother?”

“Yes.”

“Jessica, a gentleman never tells that sort of thing, just as I will never tell anything about you and myself dear.”

Frank moved next to me and gently stroked my leg. “I love sissybois, Jessica,” he said. “I will be firm yet gentle with you, my dear gurl. I will become your Daddy, and I will train you to become the best gurl you can be for your male lovers. Now, come show me what you look like in stockings and suspenders.”

I stood up and before I knew it my skirt and blouse were around my feet. I stepped out of my clothes, picked them up, and folded them over the chair.

“Beautiful, Jessica,” Frank said. “Turn around and let Daddy see you. Oh yes, you are a pretty girl. Now remove your panties and bra.”

I did as asked, and there I stood in just my black silk stockings with my clitty sticking straight up in the air dribbling and throbbing away.

Frank knelt in front of my almost naked smooth body. I could feel his ragged breath on clitty and his hard rough hands traveling down my smooth back and down over my smooth bottom. When he got to my tight cheeks, he told me to open my legs as he pulled my cheeks wide open. His fingers slipped over my little pink anus. I was quivering and shaking with excitement.

“It’s okay, baby gurl,” Frank whispered. “Daddy will take care of you now. I will love you and be gentle with you. I will train you so you know your place in life, sweetheart.”

“Oh yes, Daddy,” I moaned.

“May I touch your clitty, baby gurl? Between us, it’s only to be called your clitty from now on. I’ll own this clitty for myself alone. You’re mine, baby gurl, from now until I release you.”

“Yes, Daddy. Please.”

“Good gurl.”

I felt Frank’s big hand gently rub my throbbing clitty, slowly spreading the copious amount of sticky pre-cum juice over my cock and balls. His ring finger dipped into my foreskin and moved around and around. “Oh, you’re such a juicy little gurl, aren’t you?” He bent his head and tenderly kissed my dripping cock head.

My whole body quivered because that was the first time anyone had kissed my throbbing clitty. I was on fire as his tongue softly slid around and around my clitty head and his ring finger started to press and gently rub at my anus. I gasped and panted for breath as just the tip slipped inside. He gently rotated the tip, getting my tight little anus used to his thick, fat finger. I pushed back on his finger as his tongue lashed my clitty.

I pushed forward as Frank sucked my clitty into his mouth. My hands gripped his head as I rocked my hips back and forth fucking his mouth as his ring finger slipped in and out my anus. I quivered again as he sucked my cock hard and lashed my clitty with his tongue. It was then his finger found my prostate gland.

I moaned and gasped. “Oh Daddy. Yes… right there. Daddy, yes, yes. Oh my god, I’m coming… I’m coming, Daddy!” His finger flicked my prostate and my clitty exploded in his mouth. He sucked me gently, taking all my virgin spunk in his mouth. I cried out loud and my head started to pound. My breathing was ragged and hoarse and I swooned, my legs giving way. With a wet pop, my cock left Frank's lips and I was on my knees with my soft cock dripping with Frank’s saliva. I looked up to see Frank looking at me with a wonderful smile on his lips.

“That was your first blow job wasn't it, baby gurl?” he said.

“Yes, yes, Daddy. It was wonderful. I have never felt anything like it before.”

It was then we both put our arms around each other and we kissed for the first time. His tongue slipped between my lips. I moaned as we kissed, tasting my cum.

We broke our kiss and I giggled. “Oh my god, Daddy. That was my first kiss too.”

“You mean with a man?”

“With anyone, Daddy.”

“Are you telling me you’re a virgin, baby gurl?”

“Yes, I am.”

“Well, you won't be when you leave this house tonight.” Frank got up and held his hand out. “Come with Daddy, baby girl.”

I put my hand in his hand and felt his full strength as he easily pulled me up into his arms.

“Get up those stairs and get in my bed, baby gurl.”

I ran up the stairs followed closely by Frank. I dove onto his king-sized bed and rolled onto my back, throwing my arms over my head and opening my legs so wide to show off my now hard throbbing clitty.

“Is that for Daddy, baby gurl?” Frank said.

“Well, it’s yours now, Daddy. All yours.”

Frank pulled off his shirt and I saw how his muscles rippled. Then his shorts fell along with his boxer shorts and his big, hard cock, shaven clean and smooth and dripping with his precum, bounced into view.

I gasped. “Daddy, it’s beautiful. Is that for baby gurl?”

“How could it not be for you, my sexy little minx?”

He got on the bed and kissed me again passionately. His cock was rubbing against mine and I could feel how heavy it was. My hand went around his cock and I pulled it, wanking him slowly and exposing his big fat mushroom head. I held it and looked at it, feeling it pulsating in my hand and I knew then I had to kiss it, to love it. I looked up at Frank who was smiling down at me.

“You’re going to fall in love with my cock, Jessica. It will be the centre of your universe. Now why don’t you make love to my cock? Kiss it, suck it, lick it, taste me, baby gurl.”

I opened my mouth and my tongue slid out and over his cock head just as a large bead of pre-cum oozed out the tip. I gently lapped it off his cock head and tasted his pre-cum juices. At the same time, I slowly sucked, taking more into my mouth as my tongue lashed his cock head. I tried to copy Frank’s technique when he sucked me, but I gagged when I got it to the back of my throat.

“Take your time baby girl,” Frank whispered. “Try getting on your knees and sucking me.”

He lifted my body over his. He kissed my anus and his tongue worked on the opening me, probing in and out, deeper and deeper. Suddenly his finger delved inside of me and was quickly joined with another finger so there were two fingers up my bottom.

I sucked Frank’s cock, alternating between hard and soft and flicking the tip with my tongue to taste his sweet pre-cum juices. I dropped my head lower and lower, and all the time I could feel his fingers delving deeper into my ass. I was bucking my ass on his fingers as slowly his cock reached my gag reflex.

“Jessica,” he said. “Just relax and take your time and do it slowly, honey. Your mouth and tongue sure feel wonderful on my cock. Hmm, yes…”

Frank’s moan of pleasure spurred me on to try and swallow his whole 8 inches of cock. On and on I tried until, eventually, his cock head slipped past my gag reflex and I swallowed him to his balls. My tongue flicked out over his tight ball bag.

Frank gasped. “Yes, Jessica. It’s beautiful… it’s making me… you’re making me… Oh my god, baby gurl, I’m coming. Take it all in your throat and down into your belly. Daddy is coming!”

Frank's cock throbbed, twitched, and then jerk as jet after jet of spunk flowed from his balls through his cock into my stomach. Franks’s huge hand on the back of my head held me tightly to his scrotum as he bucked his hips. All I could do was moan as jet after jet filled my belly. Slowly the flow stopped and I pulled off his cock with a loud pop and gasped for air to breathe.

“Breathe, baby gurl, breathe. You must learn to breathe through your nose when I am that deep in your throat.”

I was still breathing hard when my big bear picked me up, pulled me in his arms, and spooned me with his still hard and dripping cock slipping up and down the crack of my bottom.

“Daddy wants to fuck your beautiful pussy ass baby gurl,” Frank said. “But first I have to stretch your boi pussy. I have some baby oil here. Let me pour a little in your pussy and over your pink little starfish. Honey, can you roll over, face down, open your legs wide, lift your bottom, and pull your cheeks wide open for me, baby gurl? That’s a good gurl.”

I felt the cool oil squirt inside me and then squirt over my bum hole. Frank reached over and opened the drawer of the table next to the bed. Reaching in, he pulled out a black pouch and from it a steel plug just about the same size my mother had in her anus. This one was silver, not black, and it had a red jewel in the end that flashed like fire in the lamplight.

“This is for your boi pussy,” Frank whispered. “It will gently open you so I can glide easily inside instead of my cock ripping you apart.”

I felt the cold steel point slowly move around my anus, then Frank pushed and turned the plug as it very gently opened my asshole up.

“Now push back, Jessica. Push as if you’re going to the toilet.”

I pushed back hard and the fat end of the plug ripped its way into my anus. The pain was instant and astonishing, a burning that ripped its way into my virgin boi pussy, then it was over. I felt the huge plug being sucked down into my sissyboi pussy.

Frank turned me over onto my back. I was muttering as my body got used to the feeling of utter fullness, and the movement within me, as the muscles of my anus tried expelling that invading lump of steel only to suck it back inside of me. I lay there in wonderment with my legs wide open. “Oh Daddy,” I gasped. “It’s beautiful.”

Frank’s rough hand went to my throbbing little clitty where he rubbed the excess baby oil all over my clitty and balls. He pulled at the plug in my ass hole and it was quickly gobbled back up inside of me, bumping my hot little prostate gland and making me moan and cry out in pleasure.

Frank lay on his side. I humped his hand as he played with my body, pulling my thick long nipples with his fingers then dropping his head to suck each in turn, lash them with his tongue, and pull them with his teeth. I gasped and cried out and arched my back as his mouth worshipped my hard and long nipples.

“You even have female nipples,” he said. “Just look at those beauties. You need to be given breasts.”

“You would turn me into a woman then, Daddy?”

“You’re already a beautiful woman, Jessica.” Frank bent his head and kissed me full-on. Our tongues twisted and turned together as he pulled my nipples once and flicked them to full erection.

We broke our kiss. “You’re such a beautiful baby gurl,” Frank whispered. “But with a tiny cock.”

I gasped as I lay wanking my 4-plus-inch cock.

“Stop doing that, sissyboi, “Frank said. “That clitty is mine, did I not tell you? If you don’t stop that, Daddy will have to cage you. Now put your hands behind your back, you bad gurl. Do I not please you? Do I not pleasure your body, baby gurl?”

“Yes, Daddy,” I said. “It’s wonderful, but I cannot help myself. I need to feel my throbbing clitty. I need to cum. You're driving me to the edge, then pulling me back again.”

“That’s what daddies do, baby gurl. We give your body the pleasures you crave.”

It was then Frank started to pull the plug that was lodged deep in my asshole. He’d pull it almost out and then let the head slide back inside my ass.

“Jessica,” he said. “Can you push the head out your pussy yet? Try pushing it out. Go on, push it out, then suck it back inside your beautiful pussyass. Yes, that’s a good gurl. Now suck it back in. Pull it deep. Yes. Now do the same thing over and over.”

I could hear the slurping of my anus as that large plug slipped in and out. If I went too far and pushed it out my pussy, Daddy would push it back in for me. I moaned and rolled my head from side to side each time I pushed out that plug and my muscles sucked it back in.

“Oh Daddy, it’s beautiful. I feel it through my whole body. Oh Daddy…”

“You’re feeling the power now of your boi pussy being invaded. Wait until you feel Daddy’s cock deep in your sissyboi pussy, baby gurl. You're going to go crazy with lust for Daddy’s cock. You’re going to cum without touching your clitty. You’ll be bouncing up and down on my big fat cock deep on your sissy cunt. Your clitty will be going off like a fire hose.”

“Take me, Daddy. Please take me now. I want your big fat cock deep inside of me. I want to feel you deep and throbbing in my boi pussy. Daddy, please.”

“You want to do it now, Jessica?”

“Yes, Daddy, more than anything. I will do anything for you, Daddy.”

“Anything, baby gurl?”

“Yes, Daddy.”

“I will remember that, Jessica.”

“Okay, baby gurl. Push that plug right out.”

I grabbed the wooden bars of the bedstead and held on tightly as I pushed and pushed until the anal plug popped out.

“Very good, baby gurl,” Frank said. He moved up the bed, took my ankles, and pushed them over my head.

I felt the mushroom head of his cock tap my scrotum. “Oh, Daddy. Yes. Make me your baby girl.”

Frank lubed his cock up and then my anus. I felt his cock head press into the opening of my sphincter. “Push, baby gurl,” he said. “Push hard.”

I pushed hard and felt his cock open me and slip inside my ass. “Daddy it hurts,” I gasped.

“The pain will pass and there will be only pleasure,” Frank said.

The pain passed as Frank pushed his cock deeper and deeper into my pussyass. As he fucked me, I trembled with excitement.

“You’re so tight, baby girl. You’re so so tight, my darling.”

His big, heavy balls slapped the cheeks of my bottom as he slowly sped up his fucking of my ass, and then there was my clitty jumping and squirting pre-cum juices over my belly and filling up my belly button. I could hear sounds traveling around the room. I heard someone crying and sobbing.

Suddenly Frank stopped fucking and looked down at me. “Oh, baby gurl. l ‘m hurting you.”

It was me that was sobbing and crying. “Daddy,” I begged. “Don't stop. It’s beautiful and I love you. I love you, Daddy! Their tears of joy because I finally understand who and what I am.”

“You’re my sissyboi,” Frank said. “You’re my new love in my life, Jessica.”

“Then show me. Fuck me, please Daddy/ fuck me.” I grabbed his big shoulders. “Come on, Daddy. Love me, fuck me. Breed my boi pussy.”

Frank lowered himself over my body and kissed me gently and lovingly, and his hips started moving as he fucked me again. “Baby gurl, you’re so wet your cock is squirting pre-cum juices everywhere as I fuck you.”

“Daddy, Daddy. I’m coming!. You’re making me come by fucking my asshole.”

“It's your pussyass, baby girl.”

“It’s… it’s… Yes! Oh, Daddy!” My cock went wild it exploded with such force. I squirted huge amounts of spunk. The first salvo hit my chin and lips. The second jet hit my shoulder, the third splashed up and over my right nipple, and, yes, a fourth jet hit the middle of my chest. A final shot splashed into my belly button. I was swimming in spunk as Frank continued fucking my ass.

Shivering and shaking from my orgasm, I was still bent in half by Frank as he screwed my boi pussy with my spunk all over us.

He licked my shoulder clean and sucked my nipple clean. I slowly licked my lips clean to show him I loved my own taste. He then kissed me and allowed all that spunk to dribble into my mouth. I tasted my cum as Frank went on fucking my tight little pussyass. On and on he fucked me, both hard and softly until my head was swimming and I felt myself starting to tremble.

“Daddy,” I gasped. “I’m coming again. I’m coming again, Daddy.” I screamed as my body broke under his cock. As if in the distance, I heard Frank roar like a lion as he rammed his cock deep. His cock throbbed and jumped inside of my ass as jet after jet filled my sissy pussy. “Breed me, Daddy,” I cried. I was coming with my lover at the same time.

After our orgasms subsided, Frank lay in my arms and my legs fell over his back. I did not wish to lose his cock just yet.

He picked up the plug. “Open your mouth and make this nice and wet. Quickly, my darling.”

I sucked on the plug as Daddy’s cock slowly shrank and grew soft until my anus pushed it out. Frank took the plug from my mouth and easily pushed it into my ass.

“There, my darling. You will keep this inside you until you get home and then you can show me how you lick Daddy’s cum from your boi pussy.”

“Oh Daddy, it was wonderful. Thank you, Daddy.”

Frank moved off of me. “Now we have to get you cleaned up and you have to clean my cock up, too.”

“How do I do that, Daddy?”

“With your mouth and tongue,” Frank said.

We got into a sixty-nine position. I sucked on his now soft cock that was still pretty big. A little dribble of semen leaked from his pee hole as I licked. I opened my mouth and tasted both him and me on his beautiful cock. His heavy balls divided between my nose and settled over my eyes while I sucked and licked his cock. Finally, Daddy rolled away and we held each other. My mind filled with erotic images as sleep took me while Frank, my big Daddy, held me to him with his cock snuggled between my bum cheeks nudging my butt plug.

End of part one

Published 
Written by Spanishmum69
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