Awakenings Pt. 02

"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 leant 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 getting out 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'd 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 and said.

"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. Half way through I plucked up my courage swallowed the mouthful of 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 the departed wife? 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 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 desert menu?"

David looked across at me.

"Would you like something sweet from the desert menu Timmy?"

I wanted to get back to David's house and time was a wasting shaking my head replied.

"No, thank you, Uncle David."

David smiled at me then looked up at the waiter saying.

"Just the check thank you, Rupert."

Who returned a minute or two later carrying a small silver tray David took the small folder from it 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 very happy. I don't want you to answer until we're home I fairly sure you will enjoy what I have in mind."

Intrigued but excited that there was something I could do to make David happy. Smiling at him 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 and we headed towards the door outside the valet had his BMW waiting for us. I thought it 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 his 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 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 a wife did she have other lovers too?"

David chuckled before saying.

"Wendy was more than okay with my Twink Kink as she use 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 bad thing He's been nothing but nice to me I just hope he isn't planning on turning me into some sort of sex slave? Nah, David's been too good to me for him 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 toys 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 a daughter 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 realise we had arrived at his house until the car stopped in the driveway. Switching of 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 very 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 be buying 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 that on the first time you wear something for me Baby Boi."

Flooded with relief I quickly maybe a little too quickly replied.

"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 open mouth and we French kissed deeply, our warm tongues danced against each other. I found 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. Your 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 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 to 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 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 I felt those massive bear paws encircle nearly 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 about my 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 him 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 feel much better than my dress trousers did. Pulling the stocking higher and higher finally reached the mid thigh when I discovered they had a band of silicon that gripped my smooth skin stopping them from falling down. Reaching down I quickly pull the other stocking up to match its twin. Squealing with delight I gushed.

"Oh David you were so right stockings feel so 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 thru 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 that 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 totally naked except for white stockings I didn't feel I was doing anything wrong or perverted in fact I was loving every second so with my hands on hips 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 recognised 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 time."

"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 flooding every fibre 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 my more than willing sphincter. Way too soon for me David pulled his finger out but he surprised me when I felt something cool touches 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 realised 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 spoke without pause.

"It started with a hair brush 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 at the moment 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 to 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 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 I felt 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 realised 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 the 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. Revelling in another new found 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 hadn't I thought of it? David's such a good teacher and so good me too I wonder how can I reward him." I was lost in my thoughts until one of David's bear paw hands came to rest on my shoulder.