The continuing story of Timmy’s awakening with the help and guidance of David.
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 descriptions of sexual actives between older males and younger males. 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.
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. Take hold of yourself and listen to the continuing story of Tammy’s awakening.
Awakenings
Part 02
Waking late, I stretched and looked towards the clock. It was 11.30 AM since it was a Sunday and as such there were no classes I decided to start my day with a nice, relaxing bath. I went to the toilet and then began running a nice hot bath, pouring in a generous portion of a bubble bath. While it was filled, I went to the kitchen to grab my morning coffee. I needed a heart starter waiting for the water to boil. I mulled over the events of the previous evening. There was no shame in what I had done, I had loved every minute, and David was wonderful, so kind and caring too. When he called me, things that normally I did not like. I thrived on them, my heart had soared when he called me His Baby Boy, and it seemed fitting whenever he had called me Twinky Timmy.
Taking my coffee, I headed for the bathroom. I placed the big mug onto the bath board crossing my much-loved cast-iron claw foot bathtub (it stays warm for ages) then slipped gingerly, slowly inching my way down into the steaming water. The foaming bubbles floated up threatening to spill over before returning to cover my body as my buns touch the bottom of the tub.
Laying my thoughts returned to the previous night. David would have been in his late fifties to early sixties, and, in my estimate, he would be about five foot ten and size-wise I consider him to be a cuddly big bear. As I have said he has a friar tuck style ring of greying hair and thinking about his hair and big cannonball head made my heartbeat quicken, groaning loudly, I stated to no one in particular.
“Mmmm Tim you like bald men now. I do; There’s nothing wrong with that Baby Boy. Hehehehehe.”
There was doubt in my mind that I would contact David. Soaking in the warm water, I wanted to ring his number but mentally slapped myself.
“Don’t be silly Tim you don’t want David to think that you’re an overly eager whore. You don’t want him thinking that you’re a slut and would put out for anyone even though you had his dick in your mouth within half an hour of meeting him.”
I eventually decided to leave calling David until Tuesday after class. My thoughts turned to what David had said regarding me shaving my legs. He was right when he said that I do not have to worry about what other people say if I feel good. Fall would be starting in two weeks and there would not be any hot days before next spring I decided to give shaving my legs another go. Grabbing a new disposable razor, I slid down into the still warmish water, so my nose was just above the water level, lifted my left leg and began at the ankle shaving my calf completely smooth then up behind my knee before carefully going up my shin. Switching to the other leg, I repeated the process then sat up so I could do my knees. Finally, I stood up and reaching behind myself I quickly shaved the hair on the backs of my legs. Turning my attention to the front of my thighs all traces of hair were gone in seconds there was not that much to remove, I have never had all that much body hair back then I probably shaved my face maybe three or four times a year. Wanting to be silky smooth for David, I decided I would shave my face, butt and face the morning of our yet to be planned rendezvous. The thought suddenly hit me. Would David want to see me again?
“Oh God I hope he does I sure would love to try riding him. I would be in control and could take it easy until my slutty hole got accustomed to David’s huge dick. Then I would show David just what a fuckslut he had found by repeatedly slamming me against his thighs until he fills my bowels with sticky cum.”
My pubic area was a different story I would shave every two to three weeks when it was about the same length as a real Man’s 2 day’s growth or earlier if it started to itch. In the beginning I used shaving cream and got a rash and ingrown hairs too every time I used any. Out of frustration I tried dry shaving it was amazing, all signs of the rash or pimples disappeared, and I have not had any in-grown hairs since.
Turning on the overhead shower, I pulled the plug in the bath and rinsed my now smooth body. After drying myself I reached for my body lotion paying particular attention to my smooth legs. I loved how it felt as I massaged the cream into my skin.
Monday lectures were torture they seemed to drag on for ages I kept daydreaming or more accurately fantasizing about what David would do to me when I saw him luckily my small cock is easy to hide because I was what seemed constantly hard as a rock. It was so bad that as soon as the lecturer let us leave for lunch I went into the toilets, locked myself in a stall and beat off like a madman, caring less if anyone heard me. In seconds of gripping my small shaft my balls tightened, and I blew my wad into my cupped hand greedy for cum I sucked then licked every drop off. Leaving the toilets, I thought.
“Fuck it I’m gonna blow off my classes this afternoon I need Denis to scratch that special itch he’s so good at.”
On the short walk at my apartment block fantasies of David occupied my mind one thought kept rearing its head.
“If he was so keen to see your legs shaved, what would he say if your turned up with all of your body hair removed?”
Each time I entertained the idea my heart beat a little faster and my little dick twitched. By the time I reached my door, my mind was made up; I would do it. Dropping my bag, I kicked off my shoes, pushed my jeans down and stepped out of them. I pulled my sweatshirt over my head. Walking into the bathroom took out a new razor and a can of shaving cream. Squirting a small peak onto my fingers smeared it over my belly then chest shivering when the cool minty foam touched my sensitive nipples.
Since I did not have very much to begin with it only took a few minutes before I reached for the foam again using another daub covered my underarms, there were way harder to shave but eventually I managed to remove all traces of the wispy blonde hairs. Dropping the razor in the sink, I was too horny to clean up right then Denis was calling my name.
Crossing to the bedroom I wiggled and shook my butt until my hipsters were falling to my ankles, stopping for only a fraction of a second before kicking them off. Flopping on the bed, I looked down at my now hairless torso, I sighed saying.
“Not too bad of a job you have done Twinky Timmy I sure David will approve.”
Calling myself Twinky Timmy now seemed appropriate whenever the sentence contained David’s name.
Opening the top drawer, I fished Denis out and took the bottle of lubricant shimmied across until I was in the center of the bed. Popping the lid open squeezed a large glob into my hand then started working my little dick putting one hand around my shaft and balls pulling everything up squeezing my balls against my pointer finger before sliding down. Having had multiple fantasies running wild thru my brain all morning was far too excited to waste time pulling my pudgy little dick, it had already been too long to wait.
Rolling over, I assumed my favorite position when using Denis, doggie of course.
Squirting more lubricant onto my still slippery fingers reached back pushing three fingers knuckle deep prying them apart as they hit bottom and sliding them back out again. Squirting another large glob of lube on to my fingers I repeated transferring it to my now super slippery fuck-chute eagerly shoving my lubricated digits deep. Turning my head to one side I managed to take Denis’ shiny latex head into my sucking mouth all too soon my need to bury his lovely shaft overtook me. Positioning my body so I was reaching up between my leg’s dildo in hand I started sliding the cool latex over my sphincter bringing mews of pleasure from my throat.
This did nothing to sate my desires so repositioned again so I could now reach back over my ass cheeks. Holding the dildo about halfway along the shaft waving in the air as I moved it closer to my willing anus. Feeling it touching its slippery destination, I lost control and shoved it hard, only stopping when hitting my clenched hand, grunting with disapproval said.
“Damn it Denis you know Timmy likes it deeper Baby deeper.”
Sliding my fingers back along the purple shaft until I was holding only the head, now there were six inches more available to me. I did not hesitate I started pushing the fake dick further into my bowels before slowly sliding it backwards halfway and in again.
“Mmmm that is it Denis, you know what your little Twinky Timmy needs. Faster Baby faster please, Mmmm “
I moaned as my arm and wrist picked up the pace becoming a blur the purple toy flashed back and forth spearing my wanton fuck-hole repeatedly. Reaching for my little dick I wrapped my fingers around the base and tried to keep pace with the dildo invading my ass. A hopeless task even if I say so myself neither the less, it did the trick and seconds later my seed flooded into my waiting palm while I squeaked.
“Ohh I’m cuming Denis I’m cuming because you feel so good deep in my slutty asshole.”
Usually once I had blown my load away, I would pull Denis out but this time I did not. Instead, I continued slam fucking my hole saying.
“This is right, a twink should be well and truly fucked by his favorite dildo if his name is Denis the double headed dildo so fuck your slutty twink as long as you want Denis.”
It would have been five minutes before I finally dropped Denis on the floor beside my bed deciding I would wash him and put him in the dishwasher after I had a nap. I drifted off with those well-fucked contented feelings flooding my sleepy brain.
When I woke up, it was dark outside, I was starving, pulling my silk robe around my shoulders headed for the kitchen. The clock on the microwave reads 1:45. Throwing a TV dinner inside, I tapped the buttons, set the timer, and started the microwave. As I waited for my meal, I thought.
“You’re wide awake and you won’t be able to sleep. What are you going to do about classes tomorrow? If you don’t get more sleep by lunchtime, you’ll be a fucking zombie.”
Seeing the microwave only had a minute to go, I buttered a couple of pieces of bread and waited for it to finish heating my meal. Stopping the countdown with two seconds on the clock I took my TV dinner to the table peeled the top the rest of the way off and wolfed down the Turkey special. Throwing the disposable tray in the bin made myself a coffee and went to the lounge room, put the mug on the coffee table, reached for the remote control, and switched the television on then pressed start on my PlayStation saying to myself.
“An hour or two of Grand Turismo 2 should help you get to sleep Tim.”
It was well over two hours later when I finally switched off the TV and went to brush my teeth. Climbing between the sheets I glanced towards the bedside clock on my dresser, the numerals glowed a red menacing red 4:52 AM.
“God classes start in just over four hours let’s hope you can get to sleep Tim.”
Before finally drifting off over an hour later I had already decided to blow off my first class for the day so that I could sleep until around 10:30 AM and still take my afternoon classes. Having forgotten to set my alarm, I slept until 1:00 PM so my plans had been ruined, scratching my balls said.
“Well, Tim you fucked up there, didn’t you? You will just have to have the entire day off, won’t you? Now I know you are hungry, how about brunch?”
Eating a hearty plate of bacon and eggs with dried tomato on the side, munching on a piece of toast, I thought. What am I going to do for the rest of what looked like a sunny Tuesday afternoon? Not that I am a sun lover, the opposite applies because I burn easily so I could hit the book’s yuck, no thanks or there is the PlayStation. I knew Grand Turismo would win that contest nine times out of ten. Loading the dishes into the dishwasher, I remembered where I had discarded Denis under my bed early that morning and went to retrieve him; He needed a deep clean.
It is the best way to clean sex toys of all sorts if they are waterproof i.e. No battery-operated devices any moron should know that. Before sitting down to play my favorite computer game I buried myself by giving my small apartment a general clean, wiping down the counter tops mopping the kitchen floor then dusting before finishing with the vacuum cleaner. It was after 3:00 PM when I flopped down on the sofa to play Grand Turismo 2 instead of reaching for the game controller, I picked up the telephone. All the time I had been cleaning all I could think about was David and how I wanted to see him again. What I really wanted was to have David treat me how Denis does, I wanted him to fuck me properly. Having wrestled with my thoughts regarding it being too early in the week to call him, I justified it but telling myself it was only one day earlier than I had planned to ring him anyway. I punched in the digits and waited for him to answer, my heart pounding in my ears. I was heartbroken when his answering machine cut in.
“Hello, this is David I can’t come to the phone right now. Leave your name and number and I’ll get back to you ASAP.”
I was not prepared for this and stammered at first.
“Errr umm hi David it’s Timmy I was hoping to catch up with you again my number is 555—–.”
Before I knew it, I had spilled my phone number, it did not worry me in the slightest that was strange, usually I do not like giving it out. Barley, five minutes later my phone started ringing, pressing the answer button, and lifting it to my ear.
“Hello.”
“Hi Timmy, it’s David how is my favorite little cocksucker?”
“I’m good, thanks for calling back. How are you?”
“Well, Baby Boi to tell the truth, I’m dying to have your sweet lips wrapped around my hard dick. What do you think of that Sweetheart?”
I was so excited just talking to him. My heartbeat must have been well over one hundred times per minute. I did not even hear him refer to me as sweetheart I simply replied.
“Oh David, Twinky Timmy would love to suck your big cock anytime you desire.”
What David said next thrilled to the core.
“That’s my Baby Boi. I cannot wait either Honey. What are you doing tonight?
David was as eager as I was for another meeting, so I felt comfortable when I told him.
“I don’t have any plans, in fact I’m free as a bird all night if you’re interested.”
“Excellent, give me your address and I’ll pick you up at 6:30 sharp. Dress nicely, I wanna show you off we’re going out for a meal, Baby Boi.”
I had not expected him to want to show me off as he put it, but my horny nature accepted it without any qualms, and I asked him.
“Do you have a pen and paper David?”
“Yes, Baby Boi I’m ready.”
Rattling off my address, I told him I could hardly wait to make a kissing sound then quickly hung up.
What the fuck did you do that for Tim? I asked myself if I really cared that much because what I wanted from him was kinkier than a simple kiss.
“Just over two hours to get ready lucky I have shaved my legs already, but I’ll still have to shave my pubis and ass. You want to be slippery smooth for David don’t ya, ya fucking Cockwhore?”
I asked myself, then answered.
“You know it is Baby Boy the smoother the better and I’m sure David will like your surprise.”
Taking two new razors to my bedroom, I expertly removed the light fuzz above my little dick before stretching it up so I could shave down along the base of my shaft. Moving down lower I spread my legs wide and did either side of my hanging ball sack before finally flattening my scrotum to assist with the removal of the few wispy hairs I had missed last time. Rolling over into the doggie position, I took the second razor and completed the task I’d begun ten minutes earlier.
Next was an enema then a quick shower. If I had more time, I would have run a bath but wanting to wash my hair in a shower would suffice. After drying off I wrapped the towel around my body and took another to wrap around my wet hair. Leaning forward, I put the towel around the back of my neck, pulled it tight across my forehead, twisted it a couple of times and straightened, reached back, and tucked the loose end up under the towel behind my head. Grabbing my hairdryer, I headed for the bedroom half an hour later having dried my hair that always frizzes out more than usual whenever I wash it turned to the closet to decide what I would wear.
“David told me to dress nicely. I wonder where he’s taking me?”
I decided on a white hipster briefs a pair of white tennis ankle socks with a cream pair of dress trousers and a crisp white shirt. I had cream patent leather shoes to match because it was the outfit my mother helped me pick out for my cousins’ wedding the previous year. I’d wear the same old school blazer as Mum said, it made me look handsome and smart.
Pulling the trousers on the feel of the fine material sliding against my smooth legs sent a shudder down my spine, I was starting to remember the benefits of having hairless legs. Perching myself on the edge of the bed, I put my shoes on before standing buttoning my shirt and stepping into the lounge room. Looking at the clock on the microwave, I saw David would be here in ten minutes. Grabbing my key’s wallet headed downstairs across the car park and stood waiting. Less than five minutes later David’s BMW pulled into the kerb he motioned for me to get in. Opening the door, I slid into the seat beside him saying.
“Hi David, it’s great to see you. You look very sophisticated tonight.”
David put the car into gear and drove off as he replied.
“Thank you, Baby Boi, I don’t get many compliments at my age. You look good enough to eat Honey.”
He hadn’t mentioned any reason he was early, and I was too far gone in the throes of fulfilling another fantasy that I wasn’t about to bring up either, instead I simply said.
“I’m yours for the night David, it’s up to you what, when and where things go down tonight.”
I couldn’t believe what I was saying but didn’t stop because everything sounded so right. I was starting to realize that I liked being submissive, especially where David was concerned. “I promised you dinner first Baby Boi besides we have a reservation. What has my Baby Boi been up to since I saw you last?”
Again, the comfort factor kicked in.
“Err well umm I took your advice and shaved my legs. You were right, it feels unreal, so smooth, and my pants rub them in such a strange but delightful way.”
“Ha, ha told you Timmy you’ll learn that David always knows what’s best. I would never do anything to hurt you, Timmy. You’re too precious and valuable to an old geezer like me.”
There he goes again making me feel more wanted than I had ever been, quickly saying.
“You are not old David, or a geezer either, in my eyes you’re a gorgeous big cuddly bear.”
“Thanks Sweetheart, how old do you think I am then?”
I thought for a second before replying.
“Let me see you have some grey hairs that are sexy as hell. Your still quite virile oh and you said that you are retired so my best guess is sixty years old. Am I close to David?”
“Ah close, I’m fifty-eight Honey.”
“Umm sorry for adding the two years, I’m nineteen by the way.”
“About what I thought and don’t worry about your pretty head Baby Boi at my age two years is nothing. Here we are.”
He had only pulled up at the valet service in front of the best Italian restaurant in town. It had a reputation for delicious food, but it was quite expensive. Walking to the entrance the Doorman greeted him by name. Seeing his home and now this I thought “he must be rich but if he is why doesn’t he have a partner?” The head waiter rushed over when he saw David almost gushing.
“Sir, it’s good to see you again. Your usual table is ready, David.”
He led us to a table, obviously set up for romantic dinners we sat down, and David turned to the waiter.
“My usual time’s two tonight please Rupert.”
“Of course, Sir perhaps a drink while you are waiting for your meal?”
“I will have a Bourbon on the rocks, and my nephew Timmy will have a Gin and tonic.”
“Right away Sir.”
When Rupert was out of earshot, I leaned across the table and whispered.
“Why did you tell him that I am your nephew?”
“Don’t worry Honey, it’ll save confusion and stop them from jumping to conclusions, it will keep em off the scent. You don’t want our secrets to get out, now do you Baby Boi?”
I answered by saying.
“No, David, I don’t want anything to come between us.”
Whilst thinking there he goes again thinking of me he’s such a gentleman any woman would be lucky to have him in their life. I know I was happy he picked me up last Saturday night.
Rupert appeared beside the table carrying our drinks. David waved him away saying.
“Leave us until the food is ready Rupert, I haven’t seen my nephew for years and we have lots to catch up on.”
“Of course, Sir as you wish.”
Not long after Rupert left us alone, I felt what I assumed was David’s foot sliding up my shin.
“So Twinky Timmy shaved his legs. Did you do it for me Baby Boi? Did you shave your legs for David’s benefit?”
Feeling turned on by having both of his sock covered feet rubbing against my lower legs drove me wild. Our eyes were locked when I replied. I lowered my head, looked at him half sideways, lifted a finger placed it just below my lower lip, pouted saying.
“I didn’t stop there David your little Cockslut is now smooth all over.”
David’s eyes widened and he asked.
“What even your underarms to Honey?”
“Yep, the whole lot it’s all gone as the saying goes, I’m as smooth as a baby’s bottom everywhere and I did it for you, David.”
Rupert soon returned with our second course a quite tasty pasta dish of some description. Halfway through I plucked up my courage, swallowed the mouthful of the delicious Pasta, and asked.
“Why don’t you have a partner, David? You seem lovely to me and as my Mum says, would be the perfect catch.”
Looking at me, he winked, replying.
“Ah that’s the problem Timmy everyone I meet is either a gold digger or an air head Hollywood Wives type. What I need is a special person someone my dearly departed wife would have liked.”
What was that he said, his wife is departed? My heart went out for him, poor guy all alone in that huge house.
“I’m sorry to hear of your loss David. If you don’t mind me asking, when did your late wife pass away?”
“Wendy battled the MS for eight years in total I cared for her totally for the last three years that she was with me. It’ll be five years next month.”
I could see the pain in his eyes reaching out my fingers touched the back of his hand David gave me a weak smile.
“She must have been a wonderful wife because it’s obvious you loved her dearly.”
“Ah she was amazing Timmy no irreplaceable would be a better description.”
I wanted to ask what he meant but Rupert approached the table.
“Will that be all David or would Sir like to see the dessert menu?”
David looked across at me.
“Would you like something sweet from the dessert menu Timmy?”
I wanted to get back to David’s house and did not want to waste any time, So, shaking my head I replied.
“No, thank you, Uncle David.”
David smiled at me then looked up at the waiter saying.
“Just my check thank you, Rupert.”
Rupert returned a minute or two later carrying a small silver tray David took the small folder from it and had a quick cursory view. Snapping it closed, he placed a credit card on top and waved Rupert away.
“There is something I want you to think about Timmy. If you say yes, it will make me incredibly happy. I don’t want you to answer until we’re home I fairly sure you will enjoy what I have in mind.”
I was intrigued but excited that there was something I could do to make David happy. Smiling at him, he replied.
“What do you want me to do, David? I just want to make my cuddly big bear happy.”
He only said four words.
“Wear stockings for me.”
They floored me but didn’t repulse me. I had never thought of it myself. As I toyed with the thought of me parading around wearing them for David, my little cockette twitched, I knew my answer would be yes. Rupert returned David’s credit card, we headed towards the door, outside the valet had his BMW waiting for us. I thought it was slightly strange when the valet held the passenger side door open for me. To start with, the drive to David’s house was silent. I suspected he was giving me time to think about his question. Five miles into the journey, David began talking.
“Wendy was the perfect woman a sexual dynamo in and out of the sack. Over the years She opened my eyes to the kinkier side of sex.”
I quickly interjected.
“No wonder you miss her so much, you poor man.”
David continued as if he hadn’t heard me.
“She was the one who introduced me to the delights Boi’s can provide. Boi’s like you, Twinky Timmy.”
“You mean she was OK with you fucking guys like me? Wow, what wife. Did she have lovers too?
David chuckled and he said.
“Wendy was more than okay with my Twink Kink as she used to call it, she joined us. Wendy loved turning them into our personal living sex toys. It was one of her favorite activities.
What have I got myself into here I inwardly asked myself. Does David want to turn me into his personal sex toy? That wouldn’t be a terrible thing He’s been nothing but nice to me I just hope he isn’t planning to turn me into some sort of sex slave. Nah, David’s been too good for me to do that. Finally, I broke the silence by asking.
“You and your wife had sex slaves?”
“They weren’t slaves Baby Boi, everything they did was of their own free will. They were simple playthings there for only one thing that was the satisfaction of our kinky desires, Wendy had quite a few that would turn heads. We always wanted children, specifically daughters. We tried IVF and everything else under the sun but never had any luck.”
Being so engrossed in what David had been saying, I didn’t realize we had arrived at his house until the car stopped in the driveway. Switching the ignition in the dark interior, David reached over caressed my hair and cheek with the back of his bear paw sized hand then asked.
“You have gorgeous legs Timmy, I know they will look even better now you have shaved them for me. Will you make me incredibly happy tonight, Timmy, will you wear stockings for David? You will love how they feel I know I do Honey.”
My mind still wasn’t made up, but I had to say something.
“I couldn’t go into a shop and buy them David I would die of embarrassment.”
“How can they know who they are for? For all they know you could buy them for your girlfriend, it’s all about having the confidence to say. Fuck You, I don’t care what you think I’m having fun. Besides, I don’t expect you to worry about the first time you wear something for me, Baby Boi.”
Flooded with relief, I quickly, a little too quickly said.
“If you have some David, it will be a pleasure to wear them for you.”
Grasping my thick dusky blonde hair he pulled me closer our lips met, his tongue pushed its way into my hungry mouth and we French kissed deeply, our warm tongues danced against each other. This highly erotic David’s cologne was intoxicating, and the stubble of his bread drove me wild with desire parting David said.
“Let’s continue this indoors I can’t wait to see my Baby Boi in stocking. You’re going to be gorgeous Honey my cock is getting hard at the mere thought.”
David opened the front door and ushered me inside a huge hand planted on my butt cheek, guiding the way. Closing the heavy wooden door, David patted my butt softly saying.
“Strip down to your briefs and make yourself comfortable on the sofa I’ll be back in a minute Baby Boi.”
Kicking off my shoes, I quickly slid my dress pants off, folded them neatly, and placed them beside my blazer over the back of a high-backed chair in one corner. Quickly unbuttoning my shirt, it joined the rest of my clothes over the chair. Slipping off my socks, I put them inside of my shoes, so I was sitting in a pair of white hipster briefs waiting for David. Almost five minutes later walked into the room dressed in a knee length silk robe; He was carrying a black plastic shopping bag. He smiled widely and crossed the settee.
“Stand up Baby Boi I want to see how well you have done.”
Standing up I was conscious of the little lump in my briefs with my hands clasped in front I hid it easily. David crooked a finger in my direction, motioning my closer saying.
“Come here my Baby I wanna feel those gorgeous legs.”
Taking a few steps forward, I found myself standing between David’s knees. David playfully swatted my clasped hands.
“Your Cockette is beautiful, you never have to hide it from me Honey. Here let me help you with these.”
His huge hands slipped around my waist and in a single movement David had my hipster briefs sinking to my ankles. Steadying myself by placing a hand on David’s shoulder, I lifted each foot for him to remove my underwear. David tossed them onto the chair with the rest of my clothes then those massive bear paws encircled my entire lower thigh slowly David began sliding them up and down murmuring. My hard little cockette was poking skywards only inches from him, but things felt different. After hearing how he talked about his dead wife, I had decided that night wasn’t me receiving pleasure. I wanted David to have the best night he’d had since losing his wife.
“So smooth mmm God, I have missed this.”
Hearing this touched my heart. I’m a big softy really and pangs of empathy flooded my brain. Automatically my hand went to the side of his head. I caressed about him and concentrated on what he was saying.
“Well, you don’t have to miss it any longer, David. Where are those stockings you promised Twinky Timmy then?”
This brought David back to reality, looking up; He smiled.
“Sit on the table I’ll show you how to start.”
David took a packet from the shopping bag and ripped it open, bringing out a pair of white stockings. Giving me one he took the other showing me how to gather the thin material up until reaching the toe.
“Point your foot over here Baby.”
David expertly stretched the nylon over my toes and up over my ankle then stopped.
“Your turn Baby but don’t stop at your ankle pull them all the way up stretching as you go.”
I shuddered when the nylon slid across my hairless calf for the first time. David was right, they felt much better than my dress trousers did. Pulling the stocking higher finally reached the mid-thigh when I discovered they had a band of silicon that gripped my smooth skin, stopping them from falling. Reaching down, I quickly pulled the other stocking up to match its twin. Squealing with delight, I gushed.
“Oh, David, you were so right stockings feel so goooood. I’ll never doubt you again.”
Looking at David, I saw a concerned look on his face, crestfallen that I’d done something wrong continued.
“Is everything OK David, have I done anything wrong?”
“No, Honey I was just thinking that we don’t want any runs in your new stockings, do we?”
Relieved it wasn’t my fault said.
“Definitely not, I don’t want to ruin them the first time I wear them.”
David’s smile told me all I had to know he reached into the bag saying.
“Here’s the solution Baby these pretty slip-on shoes will stop you going through the toes.”
I didn’t question his reply or why they were pink I simply took them from him and slid my stockinged toes into the perfect fitting soft canvas shoes. Marveling at how well they fit thought.
“How did he know what size to get?”
“Stand up and give me a little dance Honey show me how sexy my Twinky Timmy is when he wears stocking for me.”
Standing my cockette was again level with David’s face, I quickly turned away stepping to the opposite side of the coffee table. Facing him naked except for white stockings and the pink shoes. I didn’t feel I was doing anything wrong or perverted, in fact I was loving every second so with my hands on hips I asked.
“Can I have some music please David?”
“Of course, Baby anything for my sexy Stocking Boi.”
To which my only thoughts were gee, that’s a new one and seeing myself in a Christmas stocking hanging from the fireplace. David pushed play on his stereo remote immediately I recognized the song thinking “Man I feel Like A Woman” is one of David’s favorite songs too. Feeling so at ease in his company, I sang along with every word faking a microphone in my hands while twisting and grinding away for David’s admiring gaze. His eyes widened when and smile broadened each time I chimed in with the chorus. Loudly singing the last four lines of the song I rotated and thrust my hips so my tiny cockette was doing little circles in time with the music.
“Oh yeah
I’m totally crazy.
Come, come, come on baby.
I feel like a woman.”
The song finished, I looked across at David, he reached up and wiped a tear from his eye. I rushed to his side.
“Is everything OK David.”
“Yes, Baby I was just thinking Wendy would have loved you, Sweety she would have made you a pet project.”
I should have picked up on what he was saying the only thing that came into my brain, but I didn’t say was.
“That darn Wendy there she goes upsetting David again.”
Dwarfing my hand in his David led me around in front of his chair holding both of my hands smiled up at me saying.
“Now then Baby Boi turn around and bend over its time for a David style smoothness test.”
Spinning around I quickly bent over and rested my hands on the coffee table having never had anything other than fingers touch me there. Amazingly for how large David’s hands are he gently pulled my cheeks apart, I wasn’t expecting the thrill I got when this warm wet slippery thing with a mind of its own hit my perineum moved up and didn’t stop until it reached the top of my butt crack before diving back down again.
“Ohh aghh ohh aghh that feels so good David.”
Poking his tongue out he used it to probe at my wrinkled sphincter. Alternately stabbing then wildly circling my greedy hole, hearing his muffled voice, it took me a second to catch what he was saying only hearing the last few words.
“Good job Baby Boi.”
My heart soared and cockette twitched when David praised me. Soon a finger replaced his slippery tongue my sphincter was so slick with David’s saliva that his big finger slid across my puckered fuck-hole. Moaning deliriously asked.
“Mmmmmmm, please push it inside David.”
“That will depend on one thing my little Twink.”
Looking back over my shoulder as best as I could in the position, I found myself then desperately asked.
“What David?”
“Have you cleaned your fuck-hole properly Timmy?”
Cutting him off, I blurted out.
“Oh yes David, I took an enema before my shower this afternoon. That is what you meant, isn’t it?”
“Yes, Honey it was what I meant. I’m glad because that will save us time tonight. I want you to have done that before we meet each other.”
“Of course, David it’s the least I can do.”
I heard him spit and felt a wad of saliva hit my anus the finger he’d been twitching across now slid along my crack spreading the glob along his digit. As David’s finger reached my sphincter, he curled it, forcing the tip inside he didn’t stop. He simply straightened his finger and kept pushing until his second knuckle disappeared. Having a real person doing some things I’d fantasized about for years and the pleasure of flooding every fiber of my being at that moment had a strange effect on me. I started going right off.
“Ohh fuck yeah, push it deeper David deeper please. Finger your Twink’s slutty fuck-hole David. Agh yeah, agh yeah, agh yeah.”
I moaned in time to David’s fat digits, prodding me more than willing sphincter. Way too soon for me David pulled his finger out, but he surprised me when I felt something cool touching me there. He pushed it forward an inch or so into my slick fuck-chute instinctively I knew it was larger than the finger it had replaced.
“You’ll like this Baby. David knows best for his Baby Boi.”
Another inch of the cool thing entered my asshole but felt like it was three times thicker, more like two of David’s fingers. He continued pushing a third inch of what I had realized was a butt-plug up my accepting slut-hole another half inch and the pressure lessened as the main body slipped inside. My stretched sphincter snapped down around the inch diameter neck of the butt-plug pulling in the last inch trapping four and a half inches of plastic sex toy. David playfully slapped my upturned butt several times saying.
“Stand up and turn around Baby Boi. You’re such a good Twink you took that without a single complaint. Have you been practicing with that hole too, Timmy?”
Shuffling my feet, I couldn’t bring myself to answer; I just nodded.
“Well, I bet you didn’t use bananas for that, Timmy. They are way too soft. Tell me what you use Sweety tell David what his sexy Baby Boi uses to fuck himself.”
Again, the comfort factor had its familiar effect, and I was honest. Not wanting to hide anything from David, I spoke without pause.
“It started with a hairbrush then a screwdriver handle or carrots then I discovered courgettes they satisfied me for a while, but it was so hard getting them long enough without being far too thick. To cut a long story short my favorite toy now is Denis the double headed dildo. He’s made of purple Latex is about ten inches long and two in girth.”
By the time I had mentioned carrots David had slipped a hand inside his robe I could clearly see him rubbing his stiffening cock while he listened. The description of Denis brought a little moan of approval.
“Mmmm you’re a fucking marvel Sweety. Sometimes it would take Wendy months before her conquests were anywhere near as good as you, Honey. Before you come over here and suck my dick you sexy Boi, there is one last thing that I need you to do for me Honey. It’ll make you into a cocksucker of the highest caliber.”
My eyes hadn’t lifted from watching David stroking the hardening snake in his hand. My Pansexual nature together with my over riding desire to do the best I could in anything I ever done. My answer was simple, direct, and to the point.
“What would that be David? What would make me a better cocksucker?”
He only said a single word.
“Handles.”
I was flummoxed handles, what the hell did he mean by handles?
Tilting my head to one side and pursing my lips questioningly asked.
“Handles? What do you mean by handles David?”
“You trust me don’t you, Sweety?
Answering a question with a question should have sent alarm bells ringing in my head but cock hungry me just nodded.
“That’s my Baby Boi you’re such a good Twink. Turn around and sit on the floor between my feet Sweety.”
Mindful of still having a butt-plug firmly planted in my ass in, gingerly lowered myself to the floor front of David, mind was racing with all kinds of things still trying to decipher what he had meant. Soon his huge hands start gathering my shoulder length blonde locks on one side of my head. Bunching my hair tightly in a clenched fist, David expertly wrapped something around the base several times when I suddenly realized he was putting my hair up into ponytails. Switching to the other side, David took less than a minute to finish the second ponytail. Thinking he was finished, I was about to shake my head when David took each side in turn split the ponytail between his hands gently tugging them apart, tightening the grip of what I later found out were elastic hair-ties.
“There you go Sweety your very own handles.”
I’d put my hair back in a single long ponytail, but that was because I was helping Mum clean out the garage. It didn’t feel anywhere near as good as what David had done. Reveling in another newfound delight, I shook my head from side to side.
“Oh, David you were right, I love my handle’s hehehehehe.”
Swinging my head caused the ends of my new ponytails to slap my cheeks. “They will be perfect, why didn’t I think of it? David’s such a good teacher and so good to me too I wonder how I can reward him.” I was lost in my thoughts until one of David’s bear paw hands came to rest on my shoulder.
“How about we try them out Sweety? Turn around my cock aching for a good sucking.”
While repositioning it wasn’t lost on me that David had moved forward on his seat the robe was open and his glorious dick was standing at attention. I began licking yummy pre-cum from his piss-hole and the realization suddenly hit me. “David hasn’t called me Timmy or Twinky for a while he keeps calling me Sweety, Honey or Baby instead.” Taking the bulbous foreskin covered knob in my mouth, clamped my lips around his shaft, and pulled down the loose skin just below my lips, exposing the head to my swishing tongue. My thoughts continue. “There is nothing wrong with that they are terms of endearment after all. Yeah, but they are usually used where females are concerned, then again Mum calls me all of them.”
David reached for my ponytails. I knew it was time to get serious. I wanted him to use me for his pleasure. Instead of pushing his big cock into my willing throat like I expected David lifted me off his flagpole like member. I looked up with my most disappointed look ever to see David smirking.
“Hehehehe don’t fret Sweety you’ll get my cock soon enough; I just wanted to see the look on pretty your face before you start Baby.”
I smiled broadly then opened my mouth into a wide-open cavern in need of plugging. David smiled down at me and began guiding me down onto his rampant tool not stopping until my chin touched his hairy nut sack. He held me impaled on his fuckstick for around thirty seconds before pulling up to allow me to breathe. David repeated this for a few minutes when he said what I had fantasized about the last couple of days.
“Do you want me to fuck you, Sweety?”
David lifted me from his dick with a pop, not wanting to be the eager beaver I licked my lips to stall for time, but my answer gave away how turned on I really was right then.
“Make me your whore David. Take your Baby’s anal cherry with your monster cock.”
“It will be my pleasure to take your cherry Sweety now let me up, you lean on the table so I can get at your slut-hole again.”
Doing as I was told I wiggled my butt at David as he stood behind me. He playfully slapped my right butt cheek two or three times saying.
“Steady up there Sweety I’ve gotta get a hold of your plug.”
I froze allowing David to grip the small, rounded base between thumb and forefinger. David pulled it backwards against my tight sphincter. It felt like it would never come out. When he suddenly released the butt plug driving what little he had gained back in. This process was repeated each time a little more was removed gradually stretching my hole getting it ready for David’s huge dick. Finally, the plug slid freely of my punished hole and before it could regain the tightness David squirted several globs of lubricant into my open fuck-hole and three more across my now winking sphincter. Using his large member, David rubbed it between my butt cheeks, spreading the slippery lube along his shaft. My heart was beating out of my chest. Looking back at him, I almost screamed.
“Don’t tease me David, Fuck your Baby Boy with that gorgeous hunk of man meat.”
He didn’t answer but he positioned his fat knob against my hungry sphincter. Thinking he may like it when I beg for it, so I said.
“Mmmmm that’s the spot David now please push your big cock inside.”
David rewarded me with four to five inches of that lovely fuckstick. Still not satisfied I whined.
“Give it to me David treat me like a whore. Fuck me David fuck me hard.”
As I said “hard” David drove the rest of his wonderful dick deep into my fuck-chute with a grunt. He held me there for a second then with his huge hands around my waist guided me forward until only the bulbous head was still inside me before slamming back into my willing body. Again, I was nothing but David’s plaything just a sex toy and I fucking loved every second because I was making David happy. With every powerful stroke his huge hairy nut sack would slam into my tiny hairless scrotum and balls whilst my cockette slapped against my pubic area. It was driving me wild and hearing David’s grunts and groans I knew he was enjoying himself too.
“Fuck yeah, yeah, yeah, yeah, yeah, yeah.”
I exclaimed in time to the hard thrusting of his flagpole dick as it speared my willing hole repeatedly. Feeling the familiar sensations of being on verge of blowing my wad quickly scooped up my cockette catching my modest load in the palm of my hand. A kinky thought hit me, and I looked back at David, showing him cum covered hand and said.
“Look your gorgeous big cock made me cum David without me even touching my little cockette.”
Still holding his gaze, I greedily lapped the tasty morsel from my palm, David grunted and said.
“You are a fucking little slut; You’re a superb cock sucker and one hell of a fuck too. Here’s your reward Sweety.”
David drove his fuck-pole as far as he was able into my slutty ass I felt his huge dick pulsate as spurt after spurt of David’s thick sticky cum was injected deep into my bowel. All I could think was “gee that’s a waste” don’t get me wrong I liked having David fill my wanton fuck hole with his man seed but would have rather swallowed it instead. David kept his ridged tool implanted until his balls were spent and his seed plastered my Boy pussy. Pulling his softening fuck-pole from me he suddenly pushed the butt plug back inside it slipped in much easier this time though. David sat back on his leather chair saying.
“Are you sure you haven’t had any training Sweety? You are one hell of a piece of ass. Show me how good are Baby, come here and clean David’s cock for him.”
Crossing his chair, he replied.
“Only self-training David, lots and lots of self-training hehehehehe.”
Instead of being repulsed at the thought of cleaning his dick after having it shoved up my butt all I could think was “I hope there is some of his yummy cum still sticking to it.” Taking my position between his knees, I slowly sank down until the backs of my thighs were resting against my calves. With the butt plug sitting neatly between my ankles, I was in a quite comfortable position. Taking David’s now semi erect cock in my hand finally my fingers could manage his girth. Directing the head towards my face out snaked my tongue, taking several swipes across his fat knob. I looked up to see David smiling down at me. It didn’t take my slurping tongue to clean David’s cock I was happy to do it for him; it was the least I could do for such a kind caring man. My only disappointment though was I could hardly taste any cum. Sensing I had finished, or I may have been getting him excited David reached down and lifted my head from his dick saying.
“Wendy definitely would have loved you, Sweety she would have made you her pet project for sure.”
Mentioning Wendy didn’t hit a raw nerve instead I thought “why wouldn’t she I’m an expert cocksucker and a hell of a piece of ass as David put it? I think I may have liked being someone’s pet project” Now I am interested in Wendy more than ever,” I asked.
“Did your wife have sex with her projects David?”
“Yes, she did but it was on her terms.”
“Her terms?”
“Well, Sweety I will put it this way, Wendy would fuck them, but she never let them fuck her. She said their little cockette’s couldn’t please a woman so the rest of their body should be used however a woman needs it to gain her pleasure.”
I thought about this for a minute or two before replying.
“She sounds like a very smart woman David I wish I could have met her.”
“Me too Sweety me too.”
Since talking about Wendy hadn’t upset David, I was emboldened.
“Tell me more about your wonderful wife please David.”
I sat in silence for the next few minutes listening intently, hanging on each word.
“Where do I start? Well, the woman was well into girlie Boys before I met her. She liked it so much that she helped find them we would then mold and train them into the real person she knew was hiding deep inside. She could tell their type from a mile away. Wendy was a Dome where Girlie Boi’s were concerned; she wasn’t cruel; She just loved turning them into the daughter she never had. She told me that they were better than a real daughter because she got to do all the Motherly things with them like hair make up shop for clothes and stuff. Then they had the added bonus of being able to fuck their brains out in a legal sense of the word.”
Having never thought of myself as a girl, I found the thought exciting. I loved the way the stockings David gave me had made me feel. Thinking, “You could do it if you kept it inside David’s home,” asked.
“She took them out in public?”
This brought a chuckle from David.
“Hahahaha yes Sweety she took her special daughters out in public as you put it but only when the said daughter wanted to. Wendy always left that decision up to her Girlie Boi. She said it was better for them to decide rather than force the issue she never failed by the way.”
I was intrigued and as soon as David stopped, I asked.
“Did people know they were Boys?”
This incited yet another laugh from David.
“Hehehehe Sweety we were that good it would depend on whether we wanted her to be seen as a prim and proper sweet as pie daughter, an out and out slut or an obvious Tranny whore. Wendy would decide upon their attire and look depending on the situation or destination.”
“I could never do that David I would die of embarrassment for sure.”
“They all said that in the beginning Sweety but soon changed their tune when they saw the real Girlie Boi hiding inside.”
My little cockette was rock hard leaking precum I couldn’t believe I was thinking about doing it. Reaching down I stroked my aching dick noticing David said.
“Ooooo poor Baby, talking about Girlie Boi’s has got you all excited. Stand up Sweety and let David take care of that for you.”
Standing a little too quickly was reminded of the sizeable butt plug still embedded in my ass. David shimmied forward in his seat, took my stiff little cockette to the balls and rolled his tongue around the shaft. His huge bearlike paws gripped my butt cheeks holding me in place while his hot tongue danced its way around my tiny dick. I wasn’t going anywhere though because David was giving me far too much pleasure. I knew I was close to draining my nuts again. When an image of me dressed as a slutty schoolgirl popped into my brain, I exploded screaming.
“Cummming oh fuck, oh fuck, oh, oh, oh.”
Only when David was sure my orgasm had subsided did he finally released my softening cockette. Knowing what came next, I dutifully sank to my knees, poked my tongue out and looked up at David expectantly. Leaning forward he let my cum slowly dribble and them drip the inch or so between us. Swallowing the tasty morsel lifted myself and sucked his tongue into my mouth for a passionate French kiss parting David nearly broke my heart.
“It’s getting late Sweety get dressed and I’ll drop you off.”
“I wish I could stay longer David.”
“Me too Sweety, I suppose you could spend the weekend with me if you’re free.”
Having a nil social life, it was a given that I had nothing to do that weekend, or any other was about to answer when David continued.
“It’s a big decision and I don’t expect you to answer right now, take a little time to think it over Sweety I’ll call you on Friday. You can keep your stockings and the plug Sweety, keep it in and them on until you get home.”
All I could muster in return was feeble.
“Thank you, David.”
Twenty minutes later I was striding across the parking lot towards the stairway to my apartment reveling in the fat that I was wearing stockings and had a large butt plug in my asshole. My little cockette was getting harder the closer I got to my front door. Slamming the door behind me, I ripped my clothes off and paraded around the lounge room in my stockinged feet. Walking into my bedroom I spun around in front of the mirror I wanted to see if the butt plug was visible. When I saw that it had a big round fake plastic clear gem that caught the light flashing brightly whenever I moved. Turned on more than ever, I gingerly sat on the edge of my bed now loving the feeling of being so full. Rocking slowly at first I took my little cockette in one hand, the other on my stockinged thigh rubbing both in time to my rocking movements. From nowhere I suddenly blurted out.
“Fuck me Daddy fuck your Girlie Boi. Fuck my ass hard with your big cock Daddy.”
Shooting the biggest wad of cum in my short life I knew what my answer would be when David called.
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