David takes Tammy further down the rabbit hole.
This story is completely fictitious and is for adult readers only, not for minors. As such you the reader must be advised that it contains graphic, explicit sexual descriptions of Gay sex. IF YOU ARE NOT OF LEGAL AGE TO BE READING THIS STORY OR IF YOU FIND SUCH MATERIAL OFFENSIVE, PLEASE LEAVE NOW.
I in no way condone the actives described below, nor do I support those that do. My stories are for entertainment purposes only.
This is the work of a fertile mind. It remains the copyright property of the author and therefore may not be copied or reproduced without their express permission. As stated, it is fiction; Any similarities between characters and real people are unexpected and unintentional. If you recognize yourself or anyone you know. Please tell me to change any future chapters.
If sex between older males and young teens, or gay sex offends, please leave now.
For those that do like the above, please read on. I try to write detailed, sexy stories; My objective is to hopefully excite the reader. So, sit back, put your ear buds in, or get your headphones on, grab hold of yourself. This is the continuing story of Timmy AKA Tammy and their awakening with the help of a kind elderly gentleman named David.
Prologue: Since this story is a work of fantasy, I have taken the liberty of bringing the timeline to the present where technology can play its part.
Awakenings
Part 03
After David had dressed me up fully for the first time, going to class the next day was a big mistake. I could not concentrate on the lectures. I was too busy fantasizing about what the girls were wearing and how their clothes would look if I were wearing them. This was a new world for me I’d never noticed or really acknowledged girls because they would usually bully me mercilessly. Now, walking between the buildings I could not keep my eyes off them. I even followed a cute redhead wearing a short tartan skirt a white blouse and best of all a sexy pair of above knee socks. They were white and had small black bows on the back. Mesmerized, I nearly followed her into the wrong class regaining my senses I dashed for the nearest toilets.
Thankfully, they were deserted, entered a stall, closed the door, dropped my jeans, and sat down. My poor little cockette needed attention so with the images of myself dressed like the redhead flashing thru my brain it didn’t take long before I sprayed cum into my waiting palm. Greedily licking the sticky cum off I knew I wanted to be a girl but only for David at his home I lamely tried to justify the decision. Jerking off had no effect on my rampant libido it made it worse if anything.
Walking out of the toilet block saw that I was late for my last lecture for the day. Amidst deciding if I would go or not, I was distracted by a tall blonde girl walking past. The first thing that I noticed was her intoxicating perfume and the clicking of her platform boots heels on the concrete pathway. Her legs were encased in a pair of black and purple striped socks they were so long that they looked like stockings. My eyes traveled upwards to see she had on a gorgeous black leather pleated skirt. Accentuating her waist was a very wide belt and a blue short sleeved blouse. From behind all I could see was she had collar length black hair worn bob style but not her face. Trying to imagine what she looked like I saw my face but everything else was hers, my little cockette began to stir. Starting off across campus, I screamed at myself.
“Fuck class I need to see Denis.”
On the ten-minute walk to my apartment, I continued to admire any woman that was wearing stockings or a short skirt. Suddenly a kinky thought crossed my mind.
‘I should send David a sexy photo or two?’ Rushing up the stairs preoccupied, I nearly knocked my neighbor Ms. Pearson flying. Head down not looking where I was going, I ran head long into her overly ample breasts. She quickly grabbed my shoulders to stop herself from falling backwards. Ms. Pearson was the only person in the apartment block that I talked to. She would stop by regularly for a coffee but having my nose buried in her cleavage that was something completely new. Apologizing profusely, I tried to step around but she would not let go of my shoulders instead she winked at me and finally released me saying.
“Oh, Timmy that’s the closest I have been to a good feel up in years.”
Blushing brightly, I stepped aside to let her pass. Still stunned by what had happened, I stood on the stairs and listened as she continued down, laughing. With a shrug, I dismissed it as another of Ms. Pearson’s many amusing quirks.
I liked Ms. Pearson. She’d become like a pseudo-Grandmother figure. She worked at the college in the Admin Department and when I was enrolling, my mother explained that due to my shyness they were going to rent an apartment for me. She asked Ms. Pearson if she knew of any places for rent. Ms. Pearson told my mother that her nephew’s apartment had just been vacated and that she could arrange a tenancy with no problems. Since she lived in the same building, she could keep an eye on me. My mother scoffed at the mere suggestion of me having a social life. So later that week I moved into the apartment across the hall from Ms. Pearson.
Taking the last few steps, I quickly continued towards my apartment, I was so horny that I fumbled with the keys. Once in the safety of my apartment my clothes were discarded as I quickly stripped, retrieving the white stockings from the bathroom where they were drying over the shower rail.
Grabbing my phone, I went to the bedroom. Putting the stockings on I felt a flood of endorphins assault my brain; The sleek hosiery made my slender legs look even more feminine. Running my hands up, my nylon encased hairless calves sent shivers down my spine. Until I noticed a small hole in one toe, angry with myself I said out loud.
“Dang it, I wish David had given me those shoes too.”
Propping my phone on the dresser, I posed facing the camera hands on hips when the flash went off capturing the image. Wanting the next to be special reached into my bedside drawer to find the butt-plug David had given me. Licking it a few times I reached back and slowly pushed the plastic bulb into my hungry fuck-hole until my sphincter clamped down around the slender neck. Looking back at my reflection, I was happy to see its fake stone flashing madly at me. Setting the camera timer, I positioned myself doggie style facing away and waited for the flash.
Grabbing the phone, I could not wait to see how it turned out. Being disappointed, I had to take it three more times before I was happy with the results. The fourth photo I took for David was of me lying on the bed facing the camera tongue wrapped around Denis’s purple head. Then a fifth with eight inches of Denis’s plastic shaft buried in my throat that I titled “wish this was you” the last was of me side on with Denis poking out an inch or so from my ass that I captioned “your better.”
Forgetting the camera, it was time to get serious before sending the photos later. Slowly picking up the pace I drove Denis’s plastic shaft into my slutty hole with wild abandonment loving the way he rubbed against my prostate. Watching myself in the mirror my fist was a blur as I fucked myself with the big plastic dildo. Looking at my reflection I suddenly thought of the redhead’s tartan skirt and stockings my little cockette exploded I just managed to catch the cum in my palm. Collapsing on the bed I licked the semen from my hand before replacing Denis with the butt-plug.
I knew that I could not say what I really wanted in my text message. I lamely tapped out “Hello David, I thought you would like to see what your Baby Boy has been doing” and pressed send before thinking. Seconds later my phone pinged David had replied “wow that was quick” I thought. Opening his message, I was delighted to see him naked with his huge cock in hand, the text said.
“This is what you do to me Sweety.”
I quickly tapped out my reply.
“OMG! What a delightful sight, wish I were there to take care of that monster one eyed trouser snake you’re holding David.”
“Do not worry Sweety I’m saving my yummy cum for my Baby Boi. I saw my doctor today and got some little blue helpers for our weekend.”
I was a little worried about his health and I was so naive that I didn’t know what he meant so tapped in.
“Are you, OK David? What do you mean by Little blue helpers?”
His reply didn’t clarify anything either.
“Yeah, I’m fine thanks for asking. Well, I’m not talking about Smurfs LMAO. You’ll find out this weekend Sweety I know you won’t be disappointed.”
Glad he wasn’t ill, I typed.
“You had me worried there for a second.”
I then asked the question I had wanted to do on our last car ride.
“Have you ever thought of training a new toy without your Wife’s help David?”
He didn’t reply for an hour. I had gone through a range of emotions trying to think what I had said wrong when my phone finally pinged. My heart soared when I read his message.
“Yes, Sweety, but only since meeting you have those thoughts crossed my mind.”
I was so happy that he’d sent a message without thinking I replied.
“I think it will be good for both of us David.”
His reply took me by surprise but excited me too.
“I’ll pick you up tomorrow at ten sharp Sweety.”
Thinking to myself “cool, I can’t wait” sent only a single in word reply.
“Okay.”
Waking early, I gave myself an enema then showered since it was supposed to be a warmish day. I wore a pair of denim cut-off shorts with a short sleeve fleece top and runners with ankle socks. I didn’t care if anyone saw my smooth hairless legs because I had nice feminine legs and with my bubble butt I have been mistaken for a female from behind more than once. Seeing David’s BMW approaching, I propped a hand on one hip, dropped my head slightly and tried my hardest to portray a petulant teenager who had been kept waiting.
David pulled into the kerb beside me. His broad smile told me that he approved of my little show.
“Well, you look yummy today, throw your bag in the back Sweety.”
Dropping my small overnight bag on the rear seat sank into the plush leather interior.
“Hi David, I’ve missed you.”
Instead of asking myself why I had said that all I could think of was. “It’s true I have missed this wonderful man. Whenever I am with him, I feel better than ever.” Thankfully, David didn’t seem to notice.
“Hi Sweety, I see your showing those gorgeous legs you’ll make all the girls jealous. It’s such a lovely day you could get a bit of colour while we lounge around the pool?”
Again, I was fixated on only one of David’s subtle prodding questions.
“You have a pool?”
“Yeah, Wendy had it put in I’m sure you will like it Sweety its nice and private.”
“I didn’t bring any swimmers with me David.”
“If you were serious about becoming my pet project, I will take care of things like that for you, Sweety.”
David’s mere mention of me becoming his project made my heartbeat increase tenfold, and my little cockette twitched; My palms began to sweat. Reaching his driveway, I leaned across and placed a hand on his shoulder, smiling. I spoke only three words.
“Deadly serious David.”
“Well, if we work together, I’m sure you will make me an incredibly happy man Sweety, I promise that you won’t be disappointed either. And I promise that I will never force you to do anything that you do not want to do. I only have your best interests in mind Sweety.”
Walking from the garage David’s large meaty paw firmly planted on my bubble butt guiding me as we entered his house. Closing the door, David scooped me into his massive arms easily, and his tongue was halfway down my throat in seconds. Our tongues danced against each other, prodding and probing as if they were in a sword fight. Finally parting to catch our breath, a string of saliva still joined us for a second or two. I could not help myself, I giggled, saying.
“Hehehehehehe. Who’s the eager beaver now David?”
Oh, how I wanted to call him Daddy I was determined not to until he asked me, or better still ordered me to. Putting me down, he simply said.
“Who would blame me if they saw how sexy you are Sweety they would understand for sure. Where are my manner’s drop your bag here come with me and I’ll give you the grand tour.”
Over the following twenty minutes he proudly showed me his substantial dwelling but only showed me two of the five bedrooms. A woman obviously furnished the master; The room was quite feminine with flowery wallpaper and stuff. I thought “Wendy’s handy work and I guessed poor David could not bring himself to change it. We finished the tour in the humongous kitchen which overlooked a large fully landscaped inground pool surrounded on three sides by a high privacy fence fifteen feet tall. My first thought was “gee that must have cost a packet” at one end was a waterfall that has a grotto underneath and a slide wrapping around the side. Opposite it stood a huge, raised spa, a swim up bar and a cabana housing a complete kitchen I found out later that it even had a TV. David’s voice brought me back from fantasy land.
“She’s a beauty isn’t she Sweety? Wait until you see it at night with the lights on and fire bowls alight.”
“I can’t wait.”
“It such a beautiful day would you like a swim before we have lunch Sweety?”
Having seen the fence around the pool, I knew it was private enough that I would not need swimmers, so fluttering my eyelashes answered.
“Yeah, why not I can go skinny dipping that’s if you do not mind David.”
His reply took me by surprise until I remembered what he had said in the car.
“There will be no skinny dipping in my pool Sweety, I told you I have something you can wear. Strip off I’ll get it for you sweet cheeks.”
David was gone for less than thirty seconds and returned a piece of hot pink material draped in one hand. Smiling, he watched as I removed the rest of my clothes.
“This should fit, Sweety.”
David gave me the crumpled piece of flimsy cloth, as I unrolled the material discovered it was a one-piece G-string. Looking up in disbelief was about to say something, but David quipped.
“Trust me Baby, I’m the only one who will see you, and you’ll look incredible. Wendy had them made especially for Girlie Boy’s like you, Sweety. Your sexy bubble butt will look great. Come on Baby Gurl put them on for your Daddy.”
His final two words melted my heart. David wants to be my Daddy. Without another word I stepped into one leg hole followed by the other side and began sliding the stretchy material up my smooth legs. Reaching my hips, I adjusted the swimmers encasing my stiffening little cockette pulled the thin band up between my bubble butt cheeks when David stopped me.
“No, Sweety, stop Let me get some ice and I will teach you one of the most important lessons a sexy Twink like you will learn this weekend.”
David stepped over to the refrigerator, placed a glass under the ice dispenser capturing half a dozen small cubes intrigued, I asked.
“Ice Daddy, what is that for?”
“It’s to help with lesson one that is tucking.”
Showing my naive side again, I asked.
“What’s tucking?”
Reaching down, David ran a finger along the shaft of my now rock hard cockette.
“It’s how Girlie Boi’s hide these unimportant things. Do you want to be Daddy’s Girlie Boi Sweety.”
Always being taught that honesty is the best policy, I plucked up all my courage and answered him truthfully.
“I want to be your special Girlie Boi more than ever David, hopefully I can become the daughter you have always wanted, if you will have me ummm err Daddy.”
There I had said it I had called David, Daddy. Thankfully, he had mentioned the Daddy word first, but I turbocharged the situation when I asked him if I could be his daughter. Hearing myself saying those words seemed perfectly natural since I had secretly fantasized of being forced to serve a Master. David hadn’t been awful or overbearing whenever he had suggested that I wear girl’s clothing, so I was happy to oblige. The bonus was that I enjoyed it more than I had ever dreamed possible. David’s voice brought me out of my daydream.
“It will be a pleasure for both of us I assure you, Sweety. Pull down your swimmers and let Daddy show his Baby Gurl a new trick.”
Thrilled at the way he had referred to himself as my Daddy made me giddy with delight. Watching David take a handful of ice, he pushed the stretchy material down my thighs. I didn’t have time to wonder what he was up to because he opened his hand cupping my stiff little cockette and balls. The cold ice had an immediate effect on my erection; It began to wilt. Within a minute or two it was back to its normal puny thumb sized nub. David dropped the ice back in the glass took a cloth wiped his hands then my soft dick paying particular attention to drying my hanging ball-sack before saying.
“Now, that’s better we can start Sweety. Place two fingers either side of your shaft then pull your little cockette forwards thru them.”
Wondering where this was going, as David directed.
“Open your legs a bit for me Sweety.”
Shuffling my feet apart several inches giving him better access heard a murmur of approval.
Good Gurl, now this won’t hurt at all, but it may feel a little strange since it’s your first time.”
I felt David’s other huge bear paw as it came from underneath, squashing my small nuts upwards until they were bulging out under my fingers.
“OK Sweety this is it, do not push so hard against your pubic mound.”
As I released the pressure, David pushed one of my small nuts further up until it suddenly popped inside of my body quickly followed by its partner. David was right, it had not hurt a single bit, and looking down I could see them sitting above my tiny shaft vaguely reminding me of a woman’s Venus Mons.
“Step two is where we take your clitty bend it down and cover it with your now empty ball-sack like this.”
Within seconds David had my what he was now calling my clitty folded down hidden beneath the soft skin of my scrotum.
“Now you can pull your swimmers up Sweety.”
As I pulled the thin stretchy material up my thighs, David adjusted the gusset making sure my smooth hairless ball-sack was trapped evenly. Wriggling the swimwear up, I loved the way it hugged every curve and after putting my arms through the straps marveled at how well it fit. The high cut hip line accentuated my ample bubble butt cheeks, and the top half covered me nicely too.
What I liked best about the swimwear was that it had a four-inch-wide ruffled skirt around the waist that was several shades darker than the rest of the swimsuit. I could feel it just brushing the top of my naked buns with every movement. David was looking down at me, smiling broadly. He reached for my crotch and placed a finger right where my tiny cockette was trapped. Curling his fingertip, he did something that felt like he had turned my cockette’s shaft inside out because I felt the head of my cock sliding upwards towards my trapped nuts.
“There you go just like any other sexy girl, what do you think Sweety?”
Looking down although small, there was no trace of my cock and balls at all only a close inspection would reveal the truth.
Mmmm Sweety does not seem quite appropriate any more Daddy will have to give his daughter a proper name.”
Looking over my shoulder, I tried to see my naked buns and in frustration began turning in a circle. Finally, having craned my neck I could see the pink material disappearing between two big fleshy globes. David found this amusing. He picked up his cell phone and offered a solution I didn’t expect.
“Let Daddy take your picture Baby Gurl then you will see how cute and sexy you are Tammy.”
Tammy! David only changed the vowel in my name, and I absolutely loved it. Timmy sounded strange to me now, but when David called me Tammy somehow, it made me feel more feminine in a way I had never experienced before. Instead of asking where they would end up as I answered him, my only thought was that every Daddy should have a photo of their daughter.
“Oh yes I wanna see, please Daddy take my photo pretty pleasssssssse.”
“Okay Sweety rules for Daddy’s photos are chest out, stomach in, ass out.”
David stood back and directed me when to turn as he took three pics from the front the side and from behind. Rushing across to him I hung off his shoulder, looked down at his phone, and excitedly said.
“Show me Daddy, show me, show me pleasssssssse Daddy.”
The first photo I recognized my face but had never seen my body encased tightly in what was obviously female swim wear, nonetheless, liked what I saw.
“I wish I was prettier Daddy.”
With one of his huge bear paw hands, David gently patted my head saying.
“You are pretty Tammy very pretty, and Daddy will help his Baby Gurl with anything she needs to make her feel pretty. After all a Daddy’s job is to help make his daughter’s dreams come true.”
David swiped across to the second photo immediately after I saw the effect his three rules revealed. From the side I could see one whole creamy white cheek accentuated by the cut of the swimmers. In the first pic I could have been easily mistaken for a prepubescent teen girl but seeing the second anyone would start thinking.
“What parent would let their daughter wear something so revealing?”
David swiped to the final photo and from behind my white bubble butt shone like a beacon the narrow pink strap of the G-string disappearing between my ample buns.
“You’ve got the best ass I’ve seen in years Tammy. Have a swim while I prepare lunch I will call you when its ready Sweety.”
He patted my bubble butt as he ushered me out onto the pool deck, I felt pampered and vowed to make this weekend special for David too. For some reason I still do not know why I decided that my trapped cockette would escape from its tight confines depending on how I entered the pool. So instead of canon balling like most teenagers would I quietly slip into the cool refreshing water. Nothing down there moved so I tried breast stroking my way from end to end. Still not a single movement it was like I didn’t have a cock anymore. I thought. “It’s not like you had one before and what you did have was useless, your much better off being David’s special sex toy Daughter.”
Climbing from the pool, I settled down on a sun lounger face down. I was proud of my naked bubble butt and wanted to show it off. I was away with the pixies busy thinking about what David had said about making my dreams come true regarding being prettier. Was I prepared to do whatever David wanted to show me how prettier I could be? You bet I was, in fact I was looking forward to seeing what I would look like. Would I recognize myself? Strangely, I didn’t really care; I just wanted to see an improvement. Having not noticed David was now standing beside the lounger, his voice startled me when he spoke.
“You do not want to get too much sun on those cute bubble buns Tammy. Lunch will be here soon. if you like I can put your hair up for you while we wait Honey.”
“Oh yes please Daddy.”
Standing, I slipped a hand into one of David’s huge bear paws.
“I love it when you do my Hair Daddy, it makes me feel so feminine no, girlie is a better description.”
David set me down on the kitchen island within a few minutes. He had brushed out my damp rusty hair and pulled it up into a matching pair of ponytails. David even styled my fringe so for the first time in my life I was sporting bangs.
“There is something I can do that would make it feel ten times better when you see it, Tammy.”
“There can’t be anything better than having these lovely ponytails brushing my face whenever I do this Daddy.”
I shook my head from side to side but like a moth to a flame I took his bait completely, asking.
“What Daddy, what could be better than my ponytails?”
I hadn’t picked up the part where David had said “when you see it” I just looked at him expectantly.
“Tell me have you ever seen Goths or Punks?”
“Well yeah, of course I have but what do they have to do with me, Daddy?”
Chuckling David opened a drawer and retrieved what I first thought was a shaker can of pink paint.
“Hehehehe we could use this special-colored hairspray Wendy had for Halloween.”
Seeing my obvious concern, he quickly added.
“Do not fret Tammy, it will disappear with a couple of washes. It will be gone before you leave.”
It was my turn to play the part I wanted. Looking up at him, I put a finger on my lower lip and in my best Girlie voice said.
“If my Daddy says it will make me prettier of course, I will do it because I trust my Daddy and want to be pretty for him.”
“That’s my Baby Gurl. I love your adventurous attitude to life Tammy we are going to get along so well.”
Just then the doorbell rang.
“Good Pizza is here.”
David took my hand and guided me into the hallway leading to his front door, I was about to tell him that I could not answer the door when he said.
“I want you to stand right here with your back to the door but bending over showing off your super sexy cheeks. Will you be a good daughter and do that for me Tammy.”
Relieved, because I would not be recognized, I stayed where David had positioned me until I heard the big, wooded door close, and I heard David’s voice.
“You should have seen his face when he saw your gorgeous bubble butt Tammy it was priceless.”
We ate in the kitchen and this time it wasn’t lost on me that David poured me a glass of Pop but had a beer himself. Somehow, in a funny sort of way it just seemed right. After lunch David picked up the pink hairspray and said,
“Follow me Sweety and we will do your hair.”
He took me to the bathroom, quickly removed the elasticized bands, which held my hair up in ponytails. David then placed a towel around my shoulders and began spraying my shoulder length hair. The instant the spray began hitting my hair it changed from its usual rusty blonde to a bright pink. Looking at my reflection, I could not believe the transformation simply coloring my hair had had. David was only satisfied when there was no trace of my natural blonde. Watching David’s reflection in the mirror, I shook my now long pink mane from side to side saying,
“Oh my God, I will never doubt you ever again Daddy I feel so pretty no I feel sexy.”
“That’s good because we have just started. I want my baby Gurl to feel pretty because she is uniquely beautiful in my eyes.”
His praise made me blush and my face felt so hot you could have cooked an egg on it. Smiling weakly, I replied.
“You think I’m beautiful Daddy?”
Turning me so I was now facing him David lightly placed his massive hands on my shoulders.
“Yes, Sweety, Daddy thinks his Baby Gurl is beautiful and he will prove it but first let me do your hair Tammy.”
This development had me intrigued but I decided to be patient. David pulled my now bright pink hair up into a single ponytail but instead of placing it low down on the base of my skull where I normally would. David positioned high on my crown so that I could see it in the mirror. He then used a different brush to curl and style my fringe so that it fluffed out more than ever. I could not contain myself any longer, after clearing my throat excitedly said.
“I love my pink hairdo Daddy but how will you prove I’m beautiful?”
“Okay little Miss Eager Beaver, hehehehehe. For your first meeting with the real you, the result should be a surprise.”
“Oh, I like surprises Daddy.”
David reached into the drawer on the side under the hand basin retrieving a largish pink tote bag then took my hand.
“Come with me I do not want any mirrors while I prepare you for your meeting with the real Tammy.”
Back in the kitchen, David pointed towards the stools beside the central island.
“Have a seat little lady.”
I’m sure my heart fluttered missing a beat when he called me “little lady” quickly taking a seat watched as he opened the tote bag. From which David took several small dark tubes, two little pencils, one brown, the other black. Then a couple of things I recognized, the small plastic snap close containers used for eyeshadow and blusher. Finally, it dawned on me that David was going to apply makeup from them. The only thing going through my mind was “hurry up Daddy, hurry up.” Gone were any negative thoughts in my mind. It was a natural progression because I wanted to be the best daughter David ever had.
For the next twenty minutes or so David took great care, changing my appearance. He used a brown pencil to accentuate my eyebrows. The black one was an eyeliner. David expertly applied the latter after telling me to either, look up or down.” Next was the eyeshadow. There were three colors in the small pack, two shades of pink one light the other darker, and the final colour was a slightly darker shade of purple.
David used the darker pink on my eyelids followed by a thin line of purple that started above my eyeball gradually widening the closer it came to the corner of my eye. Lastly, he used the light pink on my upper eyelids, blending it perfectly. David picked up one of the small tubes then directed me to look down while he brushed my eyelashes with Mascara several times.
“Almost finished Baby Gurl, just a touch of blush and your lippy then you can meet Tasteful Tammy.”
David started brushing the pinkish powder along my cheek bones before I could answer.
“I can’t wait to see if I’m pretty Daddy.”
David’s reply took my breath away.
“You are fucking gorgeous Baby Gurl. Now close your eyes, open wide, and stretch your sexy lips so Daddy can put your lipstick on.”
If Ms. Pearson saw me, she would say that I was swooning, but I think she would never have said what David had. Automatically following his directions, I was amazed at the feelings simple lipstick had on me. It was as if my lips were somehow encased in something stretchy, and the feint flavor of strawberries excited me too; David’s voice brought me out of my daydream.
“Run your lips over each other to smooth it out Sweety.”
Having watched my mother do this hundreds of times knew exactly what David meant. The encased feelings were intensified and when I ran my tongue over my painted lips discovered it was flavored strawberry. My first thought was “I hope it’s pink too” but what David said made me feel extra special.
“Wow Tammy, you’re the sexiest daughter that I have ever had the pleasure of training. With you it’s not really training because you’re such a natural Sissy Gurl. All the other Gurls have taken weeks longer before they were as comfortable as you are Sweety.”
Intrigued about his other Gurls asked.
“How many Gurls have you trained Daddy?”
“Well, Sweety there was Vicki previously Ricky, Jenny previously Kenny and Wendy’s favorite was Kylie previously Kyle. So, Tammy, you are the fourth little darling I have had the pleasure of taking on for Sissy training.”
“Gee, do you still see any of them?”
I asked, David’s face took on a faraway kind of look, as if he was reminiscing about days gone by. He smiled, saying.
“No, they have moved on in their lives in fact they have all married nice men.”
It was my turn to be shocked; It never occurred to me that a sissy could get married. So, my next question showed how young and ill-informed I was.
“They’re married, no way?”
David chuckled, saying.
“Hehehehehe why shouldn’t they get married if they find the right person. It’s what all little girls dream of their wedding day. Go to the bathroom and see how God Damn cute you are Tammy.”
The anticipation was killing me I jumped off the stool and ran towards the bathroom to the sound of David’s voice.
“There goes my daughter Tammy the eager beaver hehehehehe.”
Entering the bathroom, I wasn’t prepared for the image that greeted me in the mirror. There was no trace of Timmothy Gracewell. The only thing I recognized was my green eyes.
David had done such an expert job of applying my make-up that I was stunned in silence. All I could do was stare at the pretty girl looking back at me. I hadn’t noticed that David had followed me and was standing in the hallway watching; His voice broke the silence.
“There’s just this Tammy, and Daddy’s work will be done.”
I glanced at David’s reflection but couldn’t see what he was holding. When he entered the bathroom, I turned to face him and noticed a pair of large gold hoop earrings in his hand. Seeing my concern, David reassured me.
“Do not worry Tammy they are clip on earrings; Daddy knows his daughter ears are not pierced yet.”
David emphasized the “yet.” I was relieved when he said clip on, I hadn’t really listened to the rest of what David had said so I missed the all-important “yet” instead I excitedly said.
“Daddy I can’t wait, how do they work?”
David showed me how the small spring-loaded tab could be attached to my ears. In seconds, he clipped each one to a lobe. They hung down and stayed in place while I shook my head. I loved the way they smacked my neck with every move.
“Oh, Daddy there perfect and by the way you are right too.”
Standing on my tipsy toes, I planted a kiss on David’s cheek.
“Thank you thank you for showing me that I am beautiful I really like Tammy.”
“Oh Sweety, we have only just started there is so much more your Daddy has to teach you. When I have finished Tammy, you will not only look like, but you will feel like and act like the beautiful Gurl your Daddy knows you are, inside and out.”
Again, I didn’t pick up on the double meaning David had implied. Taking it on face value I innocently thought “I’ll be so beautiful that I will feel like a real girl, oh god yes” instead of inside and outside meaning indoors and outdoors. Wondering what else David could do to make me even prettier dumbly asked.
“How Daddy?”
“Hehehehehe you will learn how Daddy wants his daughter to dress. Sometimes demur other times slutty and how to do your makeup accordingly. Then there’s how to walk, talk, and act so no one would ever know our special secret. Not that anyone would ever find out anyway because Daddy knows his Baby Gurl is way too shy and he accepts that.”
Wanting to show my appreciation I reached for David’s groin and began massaging his semi erect dick thru his pants. Looking up, batting my thick dark mascaraed eyelashes, and pursing my lips seductively, as in my best little girl’s voice asked.
“Daddy, can Tammy suck your big cock?”
“No, not yet eager beaver there is one more thing before I let you have your way with Daddy’s fuckstick. You stay here I will be back in a flash.”
David’s first word left me crestfallen but as he continued, I became intrigued. Spying my reflection, I could not think of anything that would improve what I saw in the mirror. Looking back at me was a girl that would get a whole lot of attention from the jocks at college. That thought gave me an unexpected rush. David appeared at the door holding a pair of shiny black high heels with straps that go around the ankle. Seeing the shoes, I gulped in a breath and blurted out.
“Gee, I hope I do not break an ankle, Daddy.”
“Do not worry Sweety these are only Kitten heels you will get used to wearing them in no time. Soon you will to be able to run in them if necessary Sweety. Then you can graduate to proper Cat heels”
My gaze was fixed on the shoes all could think was, “this man knows me better than I know myself. How did he know about my desire to try heels?”
I didn’t notice that David had started taking photos. It only registered that he was in the room when I felt his rough hand touch my smooth calf.
“Lift up Sweety and Daddy will help you with your heels.”
Dutifully I lifted my leg, allowing David to strap the two-inch high heel to my foot. As I stepped up and took all my weight, I was amazed at how well it fit. I teetered there on tippee toe getting used to being much taller than usual while David quickly strapped the other shoe in place. It is easier to balance now that I had four points of contact with the floor even though two of them were only an inch across. David stood beside me; We both looked in the mirror, and he was smiling broadly.
“Give me your hand Sweety I’ll help you get used to them.”
My hand was dwarfed by David’s big hand; I instinctively grasped what was comfortable and manageable that was three fingers. David laughed and led me up the hallway towards the kitchen. With every step my heels clicked loudly on the tiles, the sound hypnotized me. I found it increasingly easy to walk in the two-inch heels. Reaching the kitchen, I felt confident enough to go alone, so I released my grip on Daddy’s arm. David watched intently as I circled the center island a few times. By my third lap I was striding confidently not touching anything because my balance was perfect. David began clapping and wiping his eyes,” said.
“Oh, Sweety you surprise your dear old Dad yet again. You do not know how much I have missed that wonderful sound your heels make. Wendy used to wear heels everywhere.”
Seeing his reaction and then him mentioning Wendy pulled at my heart strings. Suddenly a thought sparked my pansexual brain. Stopping opposite David, I leant on the cool marble countertop pouted my lips and stated.
“Well, Daddy all little Girls want to emulate their mothers since I am your daughter I will wear heels for you whenever you wish, I just want to make my Daddy happy.”
“So, you want to make your Daddy happy do you, Tammy?”
“Oh, yes please Daddy. Please tell me what I can do that would make you happy.”
He took his time before replying. I thought he was trying to compose it in his head before replying, but I didn’t quite expect what David said.
“You know I would never do anything to hurt you, Tammy.”
I was about to speak when David placed one of his huge fingers against my lips. All I could do to tell him that I knew that was by nodding my head. He continued.
“You are the most beautiful special Gurl your Daddy has ever seen. Your transformation has been miraculous to say the least. The problem is that Daddy will miss having your gorgeous form gracing his home, your heels clicking their way deeper into his heart with every step.”
David stopped for suspense. I looked at him doe eyed reveling in the praise he showers upon me. Smiling, he took a breath or two before continuing.
“Sadly, there is one thing we can’t change which is I only get to see you on weekends but there is something you could do that would help greatly whenever you’re not here Sweety. If you really want to make me happy, you will let me take photos of my gorgeous daughter, Tammy Tossco. Then I can look at my Baby Gurl when she’s not here that will make your Daddy happy.”
Months later I will realize this was the point of no return but with David’s excellent conditioning my answer was a foregone conclusion. In my mind it was just another natural progression after all I had already sent him photos of me using Denis the double headed dildo. Then it hit me that this was the perfect situation to use the cloud.
“I will miss you during the week too Daddy God I hate school I can’t wait until graduation. Of course, you can take pictures of me but under one condition.”
David raised an eyebrow and his voice deepened a touch.
“Condition Sweety what condition?”
Batting my long eyelashes at him, I said.
“Daddy, I want you to put them on the cloud so I can enjoy them too.”
“The cloud what is that?”
“Yeah, it’s an online photo album where you can store hundreds of photos and videos.”
“Videos”!
“Then I could hear your sexy heels and see that cute bubble butt sway while you walk. Oh my God Tammy you amaze your Daddy yet again. What other sexy surprises do you have in store for me? Hehehehehe.”
David exclaimed excitedly. I found out later that he knew all about storing things in the online cloud. I had only meant photos but something about seeing myself done up as Tammy performing for the camera excited me to no end. There was no way that anyone who knew me would ever recognize me, not that I had any friends at that time. The only person in this town I ever really talked to my elderly neighbor, Ms. Pearson. Most of the apartment building residents considered her a Nosey Parker, and I thought “if she saw me Ms. Pearson would never guess the pretty girl called Tammy Tossco was really her neighbor Timmy.” Seeing the excitement in my eyes, David didn’t wait for an answer, he picked up his cell phone saying.
“You’re the best daughter ever, Tammy. We will start with a few stills of you the videos can wait until later. Now smile sweetly for your Daddy, you sexy little sissy Boi.”
David stood across the countertop from me holding his cell phone. Looking directly into the lens, I tilted my head to one side and smiled. The flash went off four or five times before David was satisfied.
“That’s a good girl Tammy how about we get some action shots now?”
“Action shots Daddy what do you mean by action shots?”
“I should have said it sequentially because I will go out to one of the benches beside the pool. I want you to walk around for a little bit acting girlie do a few twirls so I can take some pics of that juicy bubble butt poking out from under your sexy swimsuit. When I call you over telling you it’s time to claim your reward, I want you to confidently stride to my side and do what you do best, my sexy cocksucking daughter.”
He was outdoors when David stopped and walked back towards me. Wondering what was happening, I asked.
“Is everything okay Daddy?”
“Yes, Sweety but I did have a sort of kinky thought.”
After reaching into a lower drawer in the kitchen, David turned to face me. He was holding out what looked like a pair of black rimmed reading glasses.
“I do not need glasses Daddy.”
“Hehehehehe they are clear lenses and they are not for vision they are to make you look more innocent with the added bonus of adding to your disguise.”
Taking the glasses, put them on, then waited inside while David assumed his position beside the pool. All I could think was “finally Daddy’s gonna let me suck his gorgeous dick again.” The anticipation was killing me I could not wait to perform for my Daddy finally I saw David signaling me to begin. The afternoon sun filled the enclosed pool area. David didn’t have to use the flash, so I had no idea how many pictures of me he was taking. He followed me with his cell phone happily snapping away as I sashayed around the pool pirouetting four or five times to show off my naked bubble butt. David finally said the words I had been hanging on.
“Tammy it’s time for your reward; come and get it Baby Gurl.”
Rushing around the pool, my heels clicked louder than ever, which made David smile even more. What I didn’t know was that he had swapped from photos to video and as I approached, he asked.
“What do you want, Tammy? Tell Daddy what his special Twink wants.”
Taking his hint, a got into character by standing in front of him, arms crossed with a pouting disappointed look.
“I’m here for my reward, Daddy. You promised that if I were a good Gurl you would let me suck your big dick and swallow all the delicious cum I can. Your Tammy has been a good Gurl Daddy. Can she please, please, please suck your big cock?”
“When you ask so nicely Tammy who am I to deny such a pretty girl what she desires.”
When David didn’t move his cell phone but kept it pointing in my direction, I should have realized what he was up to. Although at that moment in my confused brain all I could think was “David has done so much for me, and he has been extra supportive, always full of praise. Never have you felt so alive it was like you have a new purpose in my usually boring life. David has not forced me to do anything and everything he has done for me would not have been cheap. So, get over here Girl and show your Daddy how good of a cock sucker his daughter really is.”
David had been watching intently waiting patiently, from experience he knew I was putty in his hands, and he didn’t have to rush me. Moving between David’s knees, I reached down and opened his robe to find he had discarded his boxer shorts and therefore was naked underneath. I got the shock of my life when I saw that he had shaved the pubic hair from his big plum sized ball-sack and shaft.
The way he had left a large tuft of greying pubic hair on his pubis made David’s semi hard cock looked even bigger. I could not drop to my knees; I would have torn them to pieces on the rough pool decking. Sinking down splaying my legs apart so I didn’t fall backwards, I was amazed because the entrapment of my throbbing cockette was intensified.
David moved forward onto the bench, allowing me to get even closer. Reaching out I circled his now three quarters erect dick as best as I could after stroking several times, I licked my shiny pink lipstick coated lips and looked up at David, half of his face was obscured by the cell phone. So, in my best girlie voice I said.
“Oh, Daddy you’re smooth and your dick looks so much bigger now but best of all I won’t get pubic hair stuck in my teeth. I’m so hungry Daddy can you feed Tammy some of your yummy cum please?”
“You know how to make Daddy blow his load Tammy. Open wide and suck my cock you little tease.”
Leaning closer, I began licking my way down the left side of his shaft, totally ignoring the head hidden by his foreskin. Reaching his smooth ball-sack I greedily sucked on his large plumb sized nut’s first one then its twin before licking my way up the right-hand side of David’s now fully erect flagpole of a cock.
Again, I ignored the fat bulbous head instead I used both hands to roll his foreskin back fully exposing his shiny purple helmet. Cooing like a baby showered kisses all over the head of David’s rampant tool while still slowly stroking the shaft with both hands.
“Stop your teasing Tammy and suck Daddy’s cock you know you want to Baby Gurl.”
I didn’t need any encouragement I wanted to give David the best blowjob he had ever received. Adjusting my position, I opened wide taking the entire head of David’s cock into my warm wet mouth swirling my tongue around then up and over the fat head. Tasting the first hint of precum I pointed my tongue and violently stabbed at David’s piss-hole.
Davids’ groans only spurred me on I wanted to show my new daddy how well I could control my throat muscles. Taking around thirty seconds but in one single motion never stopping engulfed David’s gorgeous dick until he had filled my throat. With my chin resting on his smooth ball-sack the only thing left for me to do was swish my wet tongue back and forth across the underside of his fuck-pole.
“Mmmmmm that’s the way Tammy, suck your Daddy’s fat cock. Look up Sweety Daddy wants a photo of you deep throating him.”
It wasn’t an easy task, but I managed to look up through my pink fringe at the cell phone’s camera lens. Needing a breath, I pulled back stopping when just the fat bulb of David’s cock head was about to pop free. My cheeks puffed in and out as I gasped for air. This was when David took control, he swatted my hands away from his cock taking hold himself said.
“Rub those pretty lips over Daddy’s dick Baby Gurl. Back up a touch Sweety your Daddy wants to smear his daughter’s lipstick all over the place. The photos will look so, so sexy in our cloud album.”
I had to stop myself from laughing when David “cloud album” I covered by giving the head of his cock one last suck before forming my painted pink lips into an oval. David rubbed his knob from side to side, going well past my lips with each successive pass. When he stopped, I mistakenly thought David had finished, but then he said.
“Here Sweety your lippy needs fixing.”
Looking up, I saw he was holding a tube of pink lipstick. I could not help giggling like a little girl excitedly replied.
“Hehehehehehehe gimmie Daddy, gimmie.”
Taking the tube, I thickly smeared the strawberry flavored lipstick liberally across my lips using way more than any real girl would have. All the while thinking “if my Daddy wants to smear my lippy then it’s up to me to ensure that there is plenty to go around.” Even though I knew when David finished, I would have bright pink clown lips; That fact just excited me more than ever. Looking down at me, squatting between his legs, David said.
“Mmmmm that’s much better Sweety but it’s time to get back to your reward.”
Taking this to mean that I should suck his delicious cock I tried to push his shinny purple knob into my willing mouth David stopped me by saying.
“Whoa, Tammy your Daddy still wants to mess that pretty lippy up some more.”
Grabbing David’s thick shaft, I got right into his fantasy this time. Taking control, I sent a shiver down my spine. I moved my head from side to side while oohing and ahhing using his fat bulbous knob against my lips to spread the bright pink lipstick. At one point I felt David’s knob hit my nose. All I could smell was strawberries and wondered if they had left any trace. I knew David was enjoying himself when I heard him encourage me.
“Mmmmmmmm you are such a good Gurl Tammy show Daddy how sexy his daughter is now.”
Without letting go of David’s ridged fuck-pole, I rocked back and looked up at him, I heard the shutter of the cell phone camera go off once before David said.
“Come on smile Sweety, you want to look your best in our photos Baby Gurl?”
“Yes Daddy.”
I started grinning soon, breaking into a broad smile. David took several more photos until his free hand moved to my ponytail silently telling me it was finally time to get my reward. Looking down, I burst into the fits of giggling. David’s knob wasn’t purple any more it was totally covered in pink lipstick.
“Hehehehehehehe, Hehehehehehehe, Hehehehehehehe oh Daddy your knob is the same colour as my lippy.”
I dove right in; I positioned the head half an inch from my lips I was sure David could feel my warm breath I didn’t wait to hear David’s reply out came my tongue swiping away the pre-cum leaking from his snake eye. Taking a deep breath, I crammed David’s cock as deep as I could, cramming it against the back of my throat till I gagged. David’s flagpole of a cock felt hard, but silky soft at the same time, smelled musky, tasted salty but none of it in a bad way.
Taking my Daddy’s cock was gorgeous, his pre-cum flavored it more, it was greasy with pre-cum and throat slime, I could not get enough of it. I moaned as I sucked on his thick cock, nerves in my mouth thrilling at all the delicious sensations. David let me do whatever I wanted for the first few minutes but gradually his grip on my ponytails tightened his directions more forcefully, but I liked it.
Soon David cock was filling my throat blocking my air supply and when he finally released his grip enough to allow me to catch a breath I went into a coughing fit. When it subsided, David rammed his huge dick back down my throat my eyes were watering and snot leaked from my nose, but David didn’t slow down. This was the first time that I had seen this side of David. I liked his dominant side.
I was a rag doll in his grip allowing David to do as he wished. He used my willing throat like it was a pussy, fucking my gullet deeply then each time he pulled out so I could catch my breath David rubbed his saliva coated tool across my cheeks. Tears filled my eyes, closing them, I tried to squeeze them away, they just streamed down my cheeks, but when David said.
“Look at the camera Tammy Daddy wants to see his pretty Twink Slut’s face.”
Slightly annoyed that he wasn’t letting me suck his big dick I decided to go all out and tease David until he demands I give him head. Sucking hard on his cock I pulled back until his fat knob popped free with an audible “SWOOMP” sound. Looking up, I used my index finger to push my glasses up the bridge of my nose and smiled just in time to hear the shutter click and David saying.
“Oh yes that’s the way Baby Gurl, show Daddy your slutty face. A few more photos and you can finish sucking Daddy’s cock and collect that reward you are so hungry for Sweety.”
The voice in my mind screamed “about fucking time” instead I battered my eyelashes at the camera tilted my head and ran my tongue along the side of David’s shaft while slowly stroking his huge cock.
“Please Daddy please let me suck your dick. Tammy’s been a good girl, she just wants to please her Daddy?”
“Ah, Tammy, you have exceeded any expectations I have ever had. You are the best daughter a man could have, and you are an incredibly good Gurl.”
When David described me as “the best” and “very, very good” it made me want to put on a performance for my Daddy.
“Well, if you do not know if I am good or not then I guess I’ll have to show you just how well your daughter can suck your big cock.”
Not waiting for David to reply, I drove forwards impaling myself on David’s thick member stopping a few inches short of the base so I could swirl my tongue across the underside of his fat tool. With the abundant saliva my coughing fits had produced easily began rocking rhythmically back and forth. Only stopping whenever David’s fat bulbous knob filled my mouth. After a quick gasp of air, I slid back down, stopping when I was only halfway along his hefty shaft. I began throat fucking David’s big dick, driving his knob further into my throat with each successive thrust. David’s encouragement told me I have been doing well so far.
“That’s my Baby Girl, show Daddy that you are a good little cock sucking whore. When Daddy blows his load, you know he does not like waste so, you will show the camera your mouth full of his tasty cum before swallowing and showing us your empty mouth.”
David’s hands moved to my ponytails taking control, he started forcing his huge cock deeper until his pubic hair tickled my nose. I didn’t care at that moment all I wanted was a taste of Daddy’s yummy cum and the warm feeling I would receive once I swallowed his sticky load of jizz. David picked up the pace I knew he would not be long before I finally received my reward. Moving my hands to his thighs allowed me to get a slightly better angle where I could drive my body against his flagpole of a dick from root to tip. As David used my throat for his pleasure, he punctuated each forceful stroke by saying.
“Fuck yeah. Fuck yeah. Fuck yeah. Fuck yeah. Fuck yeah. Fuck yeah. Fuck yeah.”
After a few minutes of this punishment my jaw started to ache when David’s grip relaxed, and I finally heard him say the three words I longed for.
“Daddy’s close Sweety.”
Pulling back, I pursed my lips then held Daddy’s big fat cock head in the gap in between them. Popping my wet tongue forwards, I swished it back and forth across his piss slit and was rewarded with the familiar sweetish, slight metallic with a hint of mushroom taste of David’s pre-cum. Once I had David’s fuckstick planted against my mouth I tried to milk his seed by using both hands to rapidly stroke my Daddy’s tool.
“Get ready Tammy here comes Daddy’s baby juice. Aghhhh yesses.”
I barely had enough time to move my tongue out of the way, dropping it just as David’s huge cock began spewing hot cum against it. Since I had been warned I captured every drop easily but still waited while I squeezed the last morsel from David’s wilting dick. Before releasing his cock, I looked up to see David I had to push my glasses back up the bridge of my nose. He was smiling broadly, thus encouraged I slid my hands back onto his thighs. Pushing myself up until my face was about a foot below the cell phone David held. Opening my mouth wide I was careful not to let his cum escape, but I did push my tongue up to show the creamy semen. David quickly tapped the phone, taking several pictures then nodded for me to continue. Looking up directly at the three lenses on the back of David’s cell phone, I closed my mouth and smiled with an extravagant gesture swallowing hard. Batting my eyelashes my smile slowly widened until my mouth was wide open, I pushed my tongue out to show the camera David’s cum was gone.
“Thank you, Daddy, your cum is yummy.”
“Take your glasses off show me your sexy cock-suckers face Tammy.”
I thought this was a little strange what did he mean by “my cock-suckers face” but did as I was told without question while David snapped a couple of photos.
“Wow Sweety you’re a natural the camera loves your look.”
David turned the cell phone around showing me the last photo he had taken my face filled the screen. My makeup was atrocious lipstick smeared in an inch wide band over where it should have stopped. The tears had made my mascara run leaving twin black streaks running from the corners of my eyes. When I tried to squint the tears away it had caused the Mascara to leave dark marks above and below my eyes in short I looked like a complete and utter mess I stuttered.
“OMG!”
Then I began laughing uncontrollably I could not help myself.
“Hehehehehehehe, hehehehehehehe, hehehehehehehe, hehehehehehehe, hehehehehehehe, hehehehehehehe, hehehehehehehe, hehehehehehehe, hehehehehehehe, hehehehehehehe.”
Placing his cell phone on the bench beside himself David asked.
“What is it that you find so funny young Lady?”
Wiping away a tear I said.
“I look like Bozo the clown Daddy.”
“More like Suck-Zo-Good the cocksucking clown Sweety come inside I’ll show you how to take your makeup off quickly and easily.”
David led me to the bathroom where he handed me a small container reading the label I discovered were alcohol free wipes made especially for removing makeup. They worked a miracle taking only three to remove all traces of my demented clown features.
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