His Son's Teacher Ch. 03

"Why don't you know what to do now?" She asked, not as an accusation but more to understand him and what he was feeling. Her voice was soft.

"Well, it's...it's..." Dave stumbled over saying the things he was thinking and feeling. "It's just that...it'd be the mystery of you...not of me."

Tiffany giggled. "So a t-girl is not a big enough mystery for you?"

Her laugh and the simple truth hidden in the humor of her questioned lightened the mood. He laughed, which was music to her ears. "No...I mean...yes...you are VERY mysterious. But I mean...I wouldn't have to figure out my own mystery. I've never been attracted to men before...or even shemales. So now, when you walk out that door...I need to figure out if the divorce changed me in some very profound ways. I mean you said that you were married once. What if I decide suddenly I want to be a girl? Also, since I couldn't tell...does that make me gay?"

She smiled and slid her feet out from his lap. She saw a momentary terror on his face, thinking he had just messed things up. She stood up and walked around the table towards him. She was stunning; barefoot in exquisite stockings and his shirt. The fullness of her wonderfully feminine breasts just hinted at through his baggy shirt, and that she had only fastened two buttons on the lower half of her shirt gave him a peak at her wonderful cleavage. He half expected her to slap him as she drew in close to him...

...and slid into his lap, wrapping her arms around his neck and giving him a soft kiss. "Thank you Dave, for being honest with me about how you are feeling." She kissed him again. He wrapped one arm about her waist and explored her leg with his free hand. "I do not think you are gay. You did not ask me out knowing that I was born a he. You saw a woman you thought was attractive..."

"Beautiful." He corrected her; she paused and bathed in the compliment for a moment.

"Okay...beautiful...thank you very much." He was rewarded with another sweet kiss. His hand played with the lace tops of her thigh highs, enjoying the different textures of nylon, lace, and alabaster flesh. "But you asked out a woman...not a man. Also, have you ever worn women's clothes...other than a joke...and just because you felt 'at home' or 'natural' in them?"

"No."

"Have you ever been accused of being effeminate? Girly? A sissy?"

He shook his head 'no'.

Tiffany giggled. "Well then darling...you have nothing to worry about. You are not going to wake up some morning and think: 'gee...I'm really tired of having a penis...I think I want a pussy'." She looked at him, her words soaking in. She had meant for them to be comforting, but they looked like they stung him a little. "Listen, I didn't mean to be a bitch. It's just that this journey to my womanhood was not sudden and it was not in reaction to getting my heart broke by a woman. I always felt a little 'off' or 'different' from other boys. Then as a teen, I felt nylon against MY skin for the first time and felt...right. Tiffany was always right here," she took his hand and placed it on her left breast just above her heart, "she has always been me."

He looked her in eyes. Her beautiful, kind, soft, blue eyes. He saw into her soul, the soul of a woman. He could feel her heart beating, her wonderfully soft and warm breast in his hands. "I've never felt anything like that." He admitted.

She kissed him again, something he thought he would never get enough of. "See...nothing to worry about." She said, and he could sense the truth in her words. The dryer buzzer buzzed, her clothes were ready. "I need to get those before they get all wrinkled." She stood up and he understood the relatively new cliché 'I hate to see you go, but love to watch you leave'. She paused just before disappearing into the laundry room. "Dave?"

"Yes, Tiffany?"

"I...I can go...if you need time to think."

He took a sip of coffee and smiled. "You said you liked Star Wars...think you'd like to watch Jedi with me? We could watch it in the living room or the bedroom."

"I would love that."

* * *

Tiffany had opted for the bedroom. She was comfortable in her modest state of dress, and the bedroom fit the mood. Now that it was past noon, she would have been uncomfortable being so casual but all she had was street clothes. She knew that once she had dressed, she would be pulled to go home and prepare for the next day at school. Moreover, she did not want to leave Dave, not just yet. So they lay snuggled up watching the third movie of the original trilogy in his bed. Her legs intertwined with his, he softly groped her and she would randomly kiss him.

After their talk, she had helped him avoid blue balls by taking the time to give him another blowjob. She understood the male sex drive as well as how it felt when that urge went unsatisfied; so she did not mind doing him the favor. He noted that she was getting better at giving head. She noted that she was starting to actually really like his taste. Now they were watching as the hero entered the villain's lair to save his friends and sister. When the Princess appeared wearing a set of revealing slave silks, she felt his cock stir to life. She looked up at him and smiled, he was flushed obviously embarrassed. "Sorry," he said, "it's...it's just that this is the first time I ever felt...well...you know..."

"It's okay honey, I understand. You always wanted to do her...and I always wanted to be her." It was her turn to blush. "Once when I was in high school, my parents left me alone and I spent about three hours wearing one of my mom's pink slips, pantyhose, panties, and bra. I'd also bought a dog collar and chain and bound myself to my bed."

"Really? You...you like that 50 Shades stuff too?"

"Yes." She blushed and looked away. She felt his strong finger on her chin and her head tilted up so he could kiss her. He pulled her to his embrace, as the movie became background noise. He kissed her, passionately and possessively. She looked up at him; he had rolled her onto her back and was prying her legs apart as he slid between them. His hands were in her hair as his mouth explored her lips, earlobes, and neck. He was pulling on her hair, moving her head this way and that as he found a new place to taste.

He stopped kissing her long enough to slide a pillow under her ass, and slid the borrowed pair of bikini briefs off her. He was pleasantly surprised that the sight of her cock did not bother him as much. "Dave what are..." he silenced her by gently placing a finger on her lips. He leaned over and retrieved something out of his nightstand; a bag from the store he went to this morning. From the bag, he withdrew a box of lube. It said the brand name and 'His & Hers' in big letters above a picture of two tubes; one blue and one pink. He opened it and squeezed some from the blue tube onto his hand before rubbing it along his throbbing cock.

She groaned as he began rubbing some of the pink tube's lube along her ring, which he had learned she liked to call her 'pussy'. He watched as she squirmed beneath him as he prepared her pussy. For her part, Tiffany did her best to relax and let him have his way with her. She unbuttoned the shirt and slid out of it. He finished lubing her, and then started to rub his cockhead against her, slowly pushing in. She was still very tight, but not as tight as last night. They were not numbed by being drunk either, so he took his time as he slid into her. He paused as his cockhead slipped in and was greedily held tight by her ring. He looked into her eyes.

She moaned, it hurt but felt so good. She was also amazed that he was able to take her missionary. While considered rather vanilla and uncreative in traditionally straight couples, she had not thought it would be possible until she had her surgery. She felt him stop, so she opened her eyes and looked up at him. She smiled, not daring to say anything. He had told her to be silent, so she waited for permission to speak.

"Are you okay, Tiffany?" He asked, his voice gentle. She nodded 'yes'. "Does it hurt...bad?" He asked again, this time she shook her head 'no'. He leaned over and whispered in her ear: "I want to fuck you. I want to make you mine. I do not want to hold back, I just want to take you. Do you want that?" She nodded 'yes', this time a little more vigorously. "I want to hear you say it."

"Fuck me Dave; make me yours...do not hold back." Her voice was soft and breathless. It hurt taking him inside her, but it also felt wonderful. She loved being held by him. She loved the scent of him. Then she felt him enter her...filling her with him, and sliding all his length into her with one powerful thrust. Then he was all over her, pulling out of her until her ring caught on the lip of his glans, before slamming back into her. His mouth was on her neck kissing and sucking. His hands were squeezing her tits as he fucked her. Fucked her as if she had been born a woman.

She wrapped her legs around his waist as he slid in and out of her. Her fingernails dug into his back as she held on as his powerful body took her. She was moaning with pleasure, and even crying a little from the pain. This was the best moment of her adult life; this wonderful man was making her a woman. Then something incredible happened, he hit a spot deep inside her and she immediately came. Her body spasmed around his cock as she came, spurting her honey all across their bodies. It seemed like the orgasm lasted forever, more intensely than she had ever cum before. She was just coming down from the high when he hit it again, causing her to cum again, this time he had moved curious about the new wet sensation on his chest, so she ended up cumming on her own tits.

All Dave saw were those beautiful breasts with cum on them. This was almost too much for him. He had not seen her cock spray the cum, just this beautiful woman suddenly covered in sperm. She looked up at him; she was obviously lost in ecstasy. He enjoyed the view when his tip hit her g-spot once more and she came, once more spraying her breasts with the fluid. A glob even splattered across her lips. She parted her lips and with her tongue, lapped the glob into her mouth. The scene was just too much for him and he came, deep inside her.

His warm seed filled her, as she was finally cumming down off the intense orgasm. She made a mental note to ask Shelley just what in the hell that was...and if it was common. She felt him as he stopped thrusting and drew her into an embrace, holding her tight. Her own cock had deflated, and she could feel his doing the same inside her. Therefore, she just held on to him as long as she could, but then he was about to pop out of her and she knew she would have to rush out of bed and into the bathroom rather quickly. She kissed him, passionately as he held her.

* * *

It was around eight at night when Tiffany got back to her apartment. Dave had waited a few minutes to knock on the bathroom door. He had toweled off, his chest had been smeared by her honey too when she came. She had feared that this would be too much for him to deal with and he would want her to leave. After all, she remembered her early days when she would feel guilt the second she came while dressed. Would it be the same for him...or had he fully bought into her identity as a woman despite still being 'pre-op'?

What he wanted was to shower with her. It was a sweet affair; he washed her first, using his hands to lather her body as the warm water soothed her body. He even intentionally touched her cock for the first time, but well spent it did not rise to the occasion. When he had rinsed the shampoo from her hair, they shared a kiss under the warm shower.

Then it was her turn to wash him, a chore she relished. She loved watching the water as it ran down his chest. The feel of his muscles as she explored his body with her soapy hands. She was amazed at his virility as his cock became hard as she washed it. She was on her knees, her fingers teasing the cock back to life while she watched in fascination. She started to lean in to kiss and suck it, but he pulled her to her feet and asked her for a handjob. Without waiting for an answer, he kissed her and she obediently began to stroke his cock. His hands ranged over her body, relishing her tight ass. Squeezing her breasts. Her hands, slick with soap, stroking his cock. She felt his heart beat as the vein along the top of his shaft pulsed with life. The large mushroom shape of his glans. She teased his balls with her fingernails, and was soft and gentle with the underside of his shaft. Soon the whole dick was throbbing in her hands as he came for the last time that day. It sprayed her thighs, cock, tummy, and hand. She made a show of licking and swallowing it off her hand as he washed it off her body.

After the shower, he gave her another shirt, bikini briefs, and pair of thigh highs. She was delighted that they shared the fetish. They settled into bed and finished watching the movie. They kissed and lightly groped until dinnertime when they opted to order Chinese in. She answered the door and he relished how the driver looked at her in her immodest state of undress with lust. They ate snuggled up on the couch watching an evening news 'magazine' that had been a staple of Sunday evenings since they were both children. When it was over, she rinsed what few dishes they used and loaded his dishwasher for him. Sadly, it was also time for her to go home.

She closed the door behind and just leaned against it, happy to be home and happy to be confused over a romantic conundrum. He had taken a call from his son, and when he laid the phone down after the call and stepped into the bathroom, she entered her phone number. She really, really, really wanted him to call. However, even if he did not she had her memories, as well as his shirt which she had sneaked into her purse when he was not looking. She would sleep in it for the next couple of months. Moreover, it was a good trade; she had left her opaque thigh highs and panties under his pillow as a trophy for him. She smiled, wondering if he had found them yet.

* * *

After Tiffany went home, Dave collapsed into bed and tried to think, but found thought elusive and sleep insistent. He did not find his trophies, which had been neatly folded, perfumed, and tucked, under his pillow, until the next morning when he stripped the bed to wash the very used and dirty sheets. He smiled as he inhaled her scent. Since he had gone to bed much earlier than normal, he beat his alarm by about 45 minutes, which gave him ample time to enjoy another hot shower and decent breakfast.

He drove to work listening to the radio station she had wanted to listen to Saturday night. Normally, he listened to the news or talk radio, but this morning he was in the mood for music. It was in traffic that he realized he had made a mistake not getting her phone number. His mind brainstormed ways to get it; would showing up at school be creepy? Should he make another romantic gesture? Perhaps he should start going back to Kallisti's Coffee? As traffic slowed to a stop, he decided to get his mind into work mode, so he took out his phone to scroll through his contacts to see if there was a client, he could call. He smiled when he saw her name in his contacts, and a picture. Not only had she left her number, but she had left a picture of her as well! He opened the picture up in full size mode and was pleased. She was holding the phone up so it was from the point of view of looking down at her. She was kneeling on his bed and besides her beautiful face; he could see a nice down the shirt of her breasts as well as her nylon-clad legs. He resisted the urge to call her just then; she would be busy at school. Nevertheless, his mood was once again buoyed.

His co-workers commented on his demeanor and his best friend at his firm pulled him aside and asked him who had made him so happy. He blushed and showed him the picture. James, his co-worker, punched him the shoulder and complimented him on his conquest. He even told Dave that he should call her and see her again, that he had not seen Dave this happy since the divorce. He also warned Dave about calling too soon, that the perfect time to call was to wait three days. Dave thanked him for the advice, after all, he had been out of the dating scene for twenty years and James was a confirmed bachelor and the office womanizer.

That night, all alone in his apartment and her perfume still lingering in the air, he tried to resist the temptation to call her. James knew what he was talking about when it came to women. But then again, Tiffany was not your average woman by a long shot. It was about eight when he gave in and pulled up her contact and pressed send. "Hello Tiffany, its Dave...would you like to do dinner Wednesday night?"