His Son's Teacher Ch. 03

~ 5 ~

Slowly Tiffany awoke from a very wonderful dream. The man she had been crushing on had asked her out and in a terror and magic filled evening, she had experienced her first sexual encounters with a man. Although not quite awake, she smiled and whispered his name: "Dave." What she did not expect was the bed to move in response! Slowly as she awoke to different smells than what she was used to in her apartment, she realized that she really was in a man's bed! A dull ache in her ass also reminded her that her V-card really had been punched! And then there was the taste in her mouth...

There was also the warmth of another human being and an arm wrapped around her. She beamed in delight! It was true! She felt his morning wood stiffening against her heart shaped ass. She was still wearing his dress shirt, although in their sleep his hand had found its way inside and was now resting possessively on her tit. Even in his sleep, he was claiming her! She rubbed her foot, still clad in nylons, along his athletic legs. She felt his cock stiffen against her and she had to bite her lip to keep from either squealing in delight or giggling in joy.

"Mmmmmm...." He moaned and rolled over onto his back. Wide-awake, Tiffany knew this was her chance to make a good first morning impression. She gently turned to him and started kissing down his chest. It was muscular and hairless, and she was thankful that he slept in the nude. She found his cock and slid it into her mouth, slowly sliding the thick shaft in and out of her mouth. Last night she had admired and worshiped the member, but now she wanted him to wake up to it in her mouth as she orally made love to him. She did her best to ignore the smell and strange taste, it was not as bad as she expected. Maybe he had cleaned himself up after she fell asleep?

Within seconds, she was rewarded with his hand on her head, his fingers intertwining with her hair and gently pulling it as he started using her head to jack off into in his sleep. She smiled, yes, she knew she was being used, but she did not care. This was her way of thanking him for being a gentleman and making a dream come true, and allowing her to wake up in his arms with her dignity intact. Although, as he moaned she caught herself wondering who he was dreaming of as she sucked his cock. She could tell he still mourned for his failed marriage, but there was a spark between them. In her heart she hoped he was dreaming of her. But how would she ever know?

Slowly, she slid her tongue along the base of his shaft as he stopped pressing her head down. Right before his glans would pop out of her mouth, he pushed her back down until the tip of her nose was tickled by his pubic hair. "Oh, Tiffany..." he moaned. The words lifted her spirits, but also gave her a split second warning. She felt his shaft swell and his glans erupt inside her mouth. Once more, she tasted his cum, this time it was a little bitter. She wondered if the first time she tasted it was so good because it actually tasted good...or if it was the emotion of the moment. Then she wondered if it could have been all the whiskey he had drank the following evening.

But, it tasted good because it was her name on his lips as he came. She had worried that he would cry out another woman's name. But he had said her's instead! She was smiling as she slowly kissed her way back up his chest and then her head slowly slipped out from beneath the covers. "Good morning, handsome."

He smiled down at her. "Good morning, beautiful." He said, sleepily. "Did you sleep well?" He asked as he gently pulled her out from under the covers and held her close.

She beamed; he seemed to actually care for her comfort. "Dave...may I take a shower before I go?" She was feeling him out; she really didn't want to leave.

He frowned a little. "Do you have plans today?" He looked at the clock by his bed. "It's only about 8:45. We could cook breakfast."

The disappointed look on his face made her happy; he did not want her to go either. "No...I don't have anything until tonight...and that's just getting ready for work tomorrow. I could hang around a little bit." She noticed the weariness in his eyes. "Would you like to sleep a little more? I'm awake...I could shower and start cooking."

"That sounds wonderful, Tiff." He replied. "There's a linen closet next to the bathroom, there should be a pack of toothbrushes in there. Help yourself." She got out of bed and he took a moment to admire her. She looked so damn hot in his shirt. One thigh high's elastic had failed and now drooped on one leg. The other had a run in it.

"Listen, if you want you can use my washer and dryer." He said, realizing that he did not want her to change back into her attractive, but all covering dress. "You could borrow another shirt. Also, my ex-wife didn't like that I was always buying her thigh highs. So when I moved out she gave them back to me...still in the packaging. Help yourself; they're in the closet behind my dirty clothes hamper."

Tiffany giggled. "I don't guess she left any panties with you, would she?" She wanted to wash her panties, but did not want her 'clitty' flopping around all day ruining the illusion.

He laughed. "I have some boxers and bikini briefs in my top dresser drawer." He watched her as she gathered the clothes. She first picked a black pair of bikini briefs from his drawer. He thought it was a good pick; boxers would have covered up more of her wonderful thighs. She then leaned over and her heart shaped butt was shown off as she dub-out the nylons.

"Wow!" She said. "You've got great taste!" She was impressed by his selection, expensive silk stockings from around the world. She found one with elastic lace bands; she recognized them from the internet. "I always wondered how these would feel."

He smiled, sleepily, from the bed. "They're yours. Also, I'd put on some weight after the divorce. The shirts on the right in the back are a little larger, if you want a more loose fit." He thought she was hot and by no means needed to lose weight. But she was tall for a woman and the loser fit would give her a more feminine appearance. She selected a light blue shirt with white cuffs and collar. Gathering her change of clothing she headed off to the bathroom. Dave smiled, self-satisfied, at the way she walked awkwardly. As she softly closed the bedroom door behind her, he closed his eyes and drifted back to sleep.

* * *

The warm water felt good on her used body. She had a dull ache in her ass, but her heart was flying. Twenty-four hours ago, she was getting ready to hit the coffee shop for another Saturday night alone. Then she was surprised when the man of her dreams showed up at the coffee house, in pursuit of her! As the night's events replayed in her head, she found that her hand had drifted down to her clitty and was stroking it. She was surprised how everything was different now as she masturbated. She could taste his cum and smell his cologne. As she thought about his cock buried inside her she could feel it.

It was sensually different now. It was as if it was happening to her all over again. Her hand, lathered in soap, felt so good as she stroked her shaft. She was cumming before she knew it. "Mmm...Dave..." she softly moaned as she sprayed her honey over his shower wall. She watched in fascination as the water carried her love juices down the drain.

* * *

After a long, cleansing shower she toweled off and dressed in his clothes. The designer thigh highs felt as good as she imagined they would as she slowly rolled them up one shapely leg and then the other. His bikini briefs were a little big on her, but she looked at herself in the mirror. They were passable, and reminded her of the days when she would buy underwear like that to cross-dress in. They were more comfortable than women's panties. She might find an excuse to keep them. She giggled, realizing that now that her V-card was punched, she was considering going back to wearing under things that were comfortable instead of sexy.

She slipped into his shirt. She only buttoned the middle two buttons and looked at herself in the full-length mirror. She was pleased with how loosely it hung on her, and she was glad he had suggested putting on one larger; it looked more feminine hanging off her. She stepped out of the bathroom to retrieve her purse. She kept a spare make-up kit on her during the weekends. More than one time Shelley had called her to go out, and there was not enough time to go home and get made-up. As she quietly made her way through Dave's apartment, she could hear him quietly snoring in the bed.

Once she was done with putting on her face, she took one more look at herself in the mirror. Her long, straight brunette hair was down, brushed and freely laying across her shoulders. She put her glasses on, with better than 20/20 vision she did not need them, but she thought the black rimmed glasses gave her a more feminine appearance. Besides, she had always thought the sexy librarian look was...sexy.

Pleased with her appearance, she went into his kitchen. She marveled at the place. Dark wood cabinets, stainless steel appliances and expensive cookware...all more than she could afford on a first year teacher's salary. She found his coffee and it smelled wonderful, so much better than the stuff they sold at Kallisti's. She scooped several scoops into the coffee maker; she was delighted that he had a more traditional coffee maker than the modern, pre-measured cups of some of the newer and more gourmet coffee makers.

Happily, she began cooking breakfast.

* * *

Dave awoke to the smell of coffee being brewed. He smiled, glad that Tiffany had decided to stay and was now cooking them breakfast. He got up, went to the bathroom, and started taking a shower. The steam helped clear his head. He really liked this girl, and that really surprised him. He was a straight guy, and was never even curious about 'she male' porn or the intern at work. She was passable enough, but knowing that she was a he from the start...kept him from finding her attractive.

So why now? So many thoughts ran through his head. They clicked. She gave amazing head, and he had finally experienced anal sex...and he liked it. He liked it a lot. She was incredibly tight, and it somewhat hurt. However, he figured it would get looser as they continued having sex. Was 'sex' what he thought they had done? Was it as meaningless as a random hook-up? Or was it something deeper, had they made love? He moaned, which stirred him back to reality, a reality where he was stroking himself as he thought of all they had done. He smiled as he jerked off, thinking of the girl he had last night.

His mind wandered to pleasuring her, something he loved doing to and with his ex-wife. Kissing her lips, nibbling on her earlobes and neck before slowly making his way down her chest...kissing and exploring her body. His hand stroked faster and faster. He could smell Tiffany's perfume and taste of her skin, it was a pleasant change from still dreaming of his ex-wife. In fact, Tiffany was the first woman he had masturbated to since his ex...something he had been doing since he met her a few weeks ago.

In his daydream, he was kissing and tonguing her belly button before making a final dash for her pussy. Then it hit him; she did not have a pussy. Instead of the pink lips that he so loved, there was a hard cock. This mental image shocked him back to the reality of the situation. He was in his shower and about to cum thinking about a 'chick with a dick'. He had always prided himself in being a slow lover who loved pleasuring his woman. But he did not want to suck a cock; did she want or expect that? What about her desires...did she want to fuck him? These thoughts grossed him out; he was a straight man and in his way of thinking, sucking cock and taking it in the ass were not things straight men did.

He thought about this as he turned the water off and toweled himself dry. What should he do? He had mixed feelings and had nothing in his moral compass to point him in the right direction. He slid on a comfortable pair of designer lounge pants, no underwear...it was a Sunday after all. His world, he thought as he dressed himself on autopilot, was typically ordered and linear. However, ever since the divorce, nothing seemed to flow logically in his life. He felt as if having a failed marriage meant he was a failure as a man. Now he had had sex with a girl who was not all girl...but he could not think of as anything but a woman. Would he get past his aversion to touching another cock enough to be fair to her?

The logical side of him thought that perhaps it would be best to stop the relationship from progressing. Promise her they will be friends and then not have anything to do with her after she left his apartment. Not because dating her would be completely illogical, but rather was he emotionally ready for it? It would hurt both of them when she walked out the door, but would it be less painful in the long run? Would it be fairer? Should he talk to her and express his concern? He put on his t-shirt, deciding that he would be blunt with her. Talk about his fears and maybe let her down easy. 'Yeah, letting her down easy won't be so hard' he thought as he opened the bathroom door and was greeted with the smell of breakfast.

'It did smell good...Laura was not much of a cook, what if Tiffany is?' His heart finally having the courage to think. 'Is that a whiff of her perfume? Remember Gillian, your first love way back in high school? Didn't she wear that perfume?' His heart continued its assault on his logic.

He shook his head, willing his feelings aside as he walked into his kitchen. After all, logic had never steered him wrong by ever...looking so incredibly sexy wearing his shirt while cooking him breakfast. Logic never loved wearing black thigh highs as much as he loved seeing her wear them. Logic never delicately brushed an errant strand of hair from her face in a graceful, feminine motion that made him want more. And logic never turned and smiled at his entrance, happy to see him and say; "Good morning, Dave. Sleep well?"

It was her voice that was the final straw that broke his logic's back. "Good morning, Tiffany." He said as he confidently crossed the distance between them. "Damn logic, full speed ahead." He whispered as he swept her into his arms and kissed her, firmly and passionately on the lips.

* * *

Tiffany heard him coming, her own thoughts of logic, terror, and desire battling it out for supremacy in her heart and mind. She wasn't sure what to do, so she stood there for a moment allowing him to look at her. She blushed in her partially dressed state, and part of her wished her clothes were not in the washer but instead on her so she could flee his apartment and this awkwardness. But at the same time, her heart reminded her that he had not kicked her out and had even given her expensive thigh highs. So perhaps she should keep it simple. She turned to him and smiled, her smile brightening when she saw him. "Good morning, Dave. Sleep well?" She said.

"Good morning, Tiffany." She heard him say along with an incoherent mumble seconds before being swept into his arms. His lips were on hers, and she had surrendered to them before she could even think about what was happening. She wrapped her arms around him as he leaned into the kiss, bending her backwards like that sweet World War II picture of the sailor and the nurse. One barefoot clad in stockings, gently caressed his leg as they kissed. Their tongues danced her mouth for an eternity that was way too short.

She was blushing when he returned her to her original upright position. Now her path was clear. She would spend the day with him. It may not be forever, but being with him felt right...at least for the moment.

"How long until breakfast is ready?" He asked.

"I don't know, twenty minutes?"

"Cool." He replied thoughtfully. "I need to run to the corner store real quick...do you mind? I want some OJ to go with it, I'll be right back."

She smiled as she kissed him good-bye. It was a good sign that he felt comfortable leaving her there alone. But then again, she was not just a stranger he met at some bar, he knew where she worked.

~ 6 ~

Dave returned about thirty minutes later and put the OJ in the fridge and put something else away as she served breakfast. They sat down and began to eat. As passionate as the good morning kiss was in the kitchen, the breakfast table conversation was nonexistent. They just stared at each other with a mix of admiration and trepidation. Neither not sure how to proceed, neither wanting to mess things up. Finally, she took a deep breath. "Dave...would you like to talk about 'it' some more?"

'YES!' He almost said very loudly and very eagerly. He coughed, gathering his thoughts. "Sure..." he said, still thinking where to begin, and then thinking perhaps starting with her name would be a good beginning. "Why Tiffany? Why that name, if it isn't too personal?"

She had to suppress a giggle. A few hours ago, his dick was in her ass, and she wondered if anything would ever be too personal to talk to this man about. "That's an easy one. Had I been born with my physical gender matching my real gender, I would've been named Tiffany."

"Have you had any surgery done?" He said, he had been wondering about it all night. Had she always been so feminine or did she have work done? Also her breasts felt so natural, not like the strippers that had occupied his idle time since the divorce.

"I've had a nose job and a face-lift. Nothing too major, just enough to make me look more natural." She explained. "I've been on hormones, that's where my breasts came from. My doctor was surprised that I was able to reach stage five on the Tanner scale. Most transwomen who start in their twenties like I did are lucky to reach stage four. I was expecting to get implants, but that's $10,000 I can save for the last operation." On one hand she felt a little uncomfortable talking about it, she was afraid it would break the illusion of her as a woman. But on the other hand, if this had any hope of continuing he would have to know what the process was.

"Well, I think you're very beautiful." He reached below the table where her foot was and gently grasping it, pulled it up to his crotch and began to rub it. She smiled and cooed as his strong hands massaged the stress out of her. "Last operation?" He asked expectantly. If it was what he thought it was, that would solve many problems.

She blushed. "Yes, I'm saving to go all the way." Tiffany felt more than a little nervous. She was opening up to a guy she barely knew about the most intimate details of her life. But then again, outside of her therapist, doctor, and Shelley, he was the only one in Portland who knew her secret. Dave smiled, and she could tell that it was a relief for him. She felt mixed about it; on one hand, she wanted to be accepted for who she was. On the other hand, she herself tried to pretend that she had a different set of equipment between her legs. She knew he was a straight male and was attracted to the parts of her that were all woman, and that he had not kicked her out but instead was talking to her about in an effort to get to know and possibly date her. "I can see you would prefer I'd been born the 'other' way?"

Dave realized that his reaction to her answer had given away too much of what he was thinking. While he did not want to hurt her feelings, he did want to be honest with her from the beginning. Besides, he loved the feel of a woman's feet in stockings, and Tiffany seemed to share that fetish. As he massaged the soles of her right foot, she slowly rubbed his crotch with her left foot. "Honestly Tiffany...yes I wish you had been born a girl." He examined her expression; it was neither happy nor hurt so he continued. "It's because I've truly enjoyed the last 24 hours. Even if your secret has spun my head around. I'm not sure where to go from here. I mean, if you had a pussy...I'd know what to do."