tagTranssexuals & CrossdressersHis Son's Teacher Ch. 02

His Son's Teacher Ch. 02

byGillianCD©

~ 3 ~

"You...you have a cock!?!" Dave asked again. His date was crying in his passenger seat after giving him the best head of his life. So many thoughts went through his head. She was beautiful, how could she have a cock? Why couldn't he tell she was a he? Did this mean he was gay? She had smelled, felt and her lips even tasted like a woman...so did the cock really matter? Why was he thinking of her as a 'she' instead of a 'he'? Why couldn't he take his hand from her cock? Slowly he withdrew his hand, he had felt her lose arousal about the time she burst into tears and felt guilty.

Tiffany started getting out of his car. "Tiff," his voice was soft, "don't go." It was a command wrapped in concern.

She paused, the door opened a crack. She thought about it. So many of her transgendered friends talked about safety and security in cases like this. Most, she thought, would tell her to get out of the car and walk back to her car. After all, Dave was still a stranger and had just been thrown into emotional turmoil. She did not know how he would take it and what his response would be. It may be all right, but she may end up in the ER or worse. A few, would argue that she should follow her gut. After all, she did not know where she was and the streets at this hour could be dangerous for any woman especially one with her secret. She looked at him. His face was a mix of emotions. Confusion, fear, a little anger, but mostly concern. She closed her door. He backed out of his parking spot and left the garage.

Kallisti's Coffee where she had left her car was a short drive from the garage and they passed the 10 minutes in a very awkward silence. As he pulled in behind her car, she started to get out, silently.

"Tiff?" His voice stopped her as she was halfway out the door.

"Yes Dave?" This time he was paying attention to the sound of her voice. It sounded sweet and feminine.

"I'm sorry about back there." He had taken the 10 minutes to try to process what had happened. Nevertheless, he was only left with more questions. "I...I don't want you to go."

This shocked her. She had taken his silence as rejection. "You don't? Even now that you know what I am?"

He smiled. "I have lots of questions, some I need answered. You've thrown me for a loop. But right now, one thing I know is what you are: a woman."

She smiled back; he had said the right thing. "Well I can give you my number..."

"I would like that." He interrupted. "And I don't mean to be insistent, but I'm not sure I can wait for the answers. I mean, as I pulled up behind your car I thought about the blowjob and how your legs looked the first time I saw you and I got hard again." She looked down and sure enough, there was a bulge in his pants. "Does that make me gay?"

She looked him in the eyes. It was late, but tomorrow was Sunday. Moreover, even though it was an accident that he had found out about her secret, she had let it get that far without telling him. She felt like she owed him some explanations. "Okay. Where do you want to go?"

"Do you mind my place? I've got some wine, if we need it."

She pondered it for a moment. Her logical side told her that it was too soon, and Dave was still a stranger. It could be a trap. But her gut told her to go for it. "Mind if I follow you?"

He smiled. "Of course not."

~ 4 ~

Dave lived in a nice apartment complex in an upscale neighborhood. The buildings were all brick and it was a gated community. The cars were all luxury class and none, aside from genuine classics, appeared to be more than five years old. She felt out of place even though her Focus was only a year old. She parked next to him and he was at her door, opening it for her. He took her hand and led her to his door. His apartment was nice, if Spartan. There was a couch, an entertainment center, some bookshelves and what appeared to be a well-stocked liquor buffet. But not much else.

"Do you mind if I use the ladies room?" She asked as she slipped out of her boots.

"Of course not, it's the first door down the hall on the right." He answered. "I want to check my messages real quick." He said dialing voicemail on his cell phone.

She locked herself in the bathroom and sat, as ladies do, to pee. She pulled out her cell and texted her friend, Shelley, what was going on and where she was. That way if her gut were wrong, someone would know where to start looking for her. She also did something unusual. Nothing made her feel like a woman more than thigh highs. When she first started living as a full-time woman, she carried a spare pair everywhere she went. That way if she needed an extra boost of self-confidence she would put them on. Today she had worn yoga pants. She slipped them off and put on her stockings.

She finished, 'borrowed' some mouthwash to get rid of the cum taste still in her mouth, and joined him in the living room. He was sitting on the couch and when she entered and stood up as he had been trained to do when a lady entered the room. "I didn't know what to pour you, so I don't have us drinks yet." He said as he started towards the buffet.

"Please, sit down. I'll get it." She said with a smile and stepped over towards the buffet. Dave smiled too and sat back down. She looked the selection over. It was well stocked. There were several varieties of red and white wine some rum, expensive bottles of various whiskies. But what really caught her attention was a greenish-blue bottle. She picked up the bottle of Blue Label. "Exquisite taste."

"Do you like Scotch?" He asked, not used to women liking whisky; much less something that was such an acquired taste like Scotch.

Tiffany giggled. "Yes. But I've never had Blue Label. Too rich for a teacher's salary."

"Well then, why don't you pour us a couple fingers each? I like mine over ice." She smiled as she poured the drinks. She crossed the room to the couch and handed a glass to Dave. She took a seat next to him, curling her legs underneath her. "I see you changed leggings, why?"

Tiffany blushed. Her biggest secret was out. Why hold back now? "Well whenever I'm feeling stressed, thigh highs always makes me feel a little more confident and sexy."

Dave smiled. He liked that in a woman. In fact, he had a box of thigh highs he had bought for his ex-wife that she never wore. She hated pantyhose and delighted in returning them to him. "That's wonderful. I love a woman in hose, and you've got some pretty spectacular legs."

Tiffany blushed. "Would you like to touch them?" She waited the second for him to respond with held breath. When he nodded 'yes' she slowly uncurled her legs and stretched them over his lap. Slowly his hands touched her legs and started caressing them and her feet.

"I've got to ask..." he started. "When did you decide to become a woman?"

She took a deep breath and a long drink of her Scotch, impressed with just how smooth the Blue Label was. "Well there was always something off with me. I loved Star Wars, but that was about the only boy thing I liked. I would play Barbie with my girl cousins. Sometimes I'd be the damsel in distress when other kids played something like 'cops and robbers' and no girls were around. Then when I was a teen I found the joy of wearing Mom's pantyhose." She paused to look at him, searching his face for judgment or hate. There was none, just puzzlement and curiosity. "But I was always conflicted. I wanted to experience being a girl. But I didn't think of myself as gay. I was into women, exclusively into women. Then I was married. When she found out about my dressing she made me feel horrible about it, questioned my sexuality. Eventually so did I. When we got divorced, I started experimenting with it even more. Found some ladies, both genetic and T-gurl who helped me start to transform."

"Wow." He said, taking in her story. "So the man you said you left St Louis because, was...?"

"Me." She said solemnly. Then she looked at him, appraising his expression. "So now it's my turn to ask a question. Are you pissed at me?"

The bluntness took him aback, not being used to a lady being so forthright. But then again, this was not your typical woman. "I am and I am not." With a deep, thoughtful sigh, he put his glass down. "I mean I did pursue you, hell I thought there was this spark between us at the parent-teacher conference..."

"There was." She interrupted.

He smiled a boyish smile that she had been falling for all day and night. "...so I noticed your Kallisti's Coffee cup and thought I'd help fate along a bit."

She giggled. "Then fate wanted us to meet. I just stopped in there that night because it was close to school, their chai lattes are not too horrible, and they were serving chili that day. But their coffee sucks, and the men are too young...usually."

He laughed and it was a good sign. "Why were you there today? And if I may ask, have you been with many men?"

"Shelley, my T-gurl mentor so to speak, loves the place. We were supposed to meet, but this guy she's been crushing on who comes into her restaurant on a regular basis finally took her home. So she texted me after I ordered. So I was going to finish my coffee and leave when you showed up. As for men...you are the first man I've ever even kissed, much less blown." Dave's touch on her legs was intoxicating, it felt so good and when he massaged her feet, it felt so good after being trapped in her boots all day. This guy was really putting her at ease.

Dave actually looked relieved. "So you're just as new to this as me?" She smiled and nodded. "And you're a virgin...down there?" Again, she nodded 'yes'. He thought for a second. "No, I'm not mad. I wanted to meet you, I made it happen. It's a first for both us, so I guess I can understand why you didn't just blurt out 'I was born a man' in the middle of a public place." Dave paused a second, he was having trouble thinking of this woman as ever having been a man. "Why did you go along with it?"

She blushed and looked away from him. "I wanted it to happen just as much as you. I was just so terrified at the thought of it happening. Then I was terrified on and off all the time it was happening. But I was loving being with you. Your touch, your kiss." He reached out and gently took her hand. "When you asked me over, my heart said 'yes' before my brain could remember I still have one last man-bit." When she looked back at him, his hands moved up her leg and arm to grab her and pull her into a kiss. She was happily surprised.

Dave was just as surprised as she was that he was kissing her. He was angry that she did not tell him when he asked her to go for drinks. Or before they kissed. Or before she blew him. Well, maybe he was not angry about the last one. After all, it was the best blowjob of his life. Nevertheless, he did not know who she was before she was a she. Perhaps it was the alcohol or the late hour, but he could not think of her as anything but a woman. And there was a spark.

The kiss was passionate; she parted her lips inviting his tongue to dance with her's. She closed her eyes and wrapped her arm around his neck and shoulders while softly caressing his cheek with her free hand. This opened her body to him, his hands exploring her curves. Not satisfied with groping her through her dress and bra, he found the hem of her dress and pulled it off over her head. He took a moment to admire her body as she blushed and averted her gaze, she was exited and terrified at the same time since he was the first man to ever see her this undressed in a romantic setting. She was wearing a matching black bra and panty set with her thigh highs.

He was pleasantly surprised. She had a flat tummy, but not one with manly six pack abs. Since he had found out that she was born a man, he had wondered about her breasts. The two times he had seen her, she had been wearing dresses that concealed her cleavage. So he wondered if they were some sort of fake breast forms. Instead, they were real. Dave had learned a few things about transsexuals, his firm had hired an intern who was going through 'transformation' and she talked about the process. Some of his co-workers shunned her and called her 'it', but it was her life and what she did with it did not bother him. So he tried to be nice to her, but you could tell that she had been born a he.

But not Tiffany, had it not been for the bulge in her black panties (that he was trying damn hard to ignore for the moment) he would have sworn she was a natural born woman. She had a wonderful hourglass figure and smooth, soft skin. Her bra had a front hasp that was only too eager to be unfastened and he removed it revealing two perky breasts with quarter size areolas. Now topless, she changed position. Once more she tucked her legs underneath her and placed both hands on her ankles in a pose that jutted her breasts out in invitation to his caress.

She moaned as he touched her. They felt wonderful, he could not tell any difference between them and a natural born woman's breast. Tentatively, he leaned forward and kissed an erect nipple. Again, it was like kissing a woman's breast. He began to suckle lustfully. With each new discovery of her body being more woman than man, the less he cared about her bulge. Soon he was nibbling and sucking on her neck, not caring that he was leaving a nice sized hickey on her neck. "I need you, I want you." He whispered hungrily in her ear.

"Yes." Was all she said, all she needed to say. He lifted her off the couch and carried her into his bedroom. Gently laying her on the bed, he started taking his own clothes off, admiring the beautiful woman in his bed. He kissed her deeply and then gently guided her to all fours and pulled her panties off and tossed them to the side of the bed. He had always wanted to do this with his ex-wife, but she thought anal sex was gross. He was not prepared, he did not have a condom or lube so he spit on his hand and rubbed it on his thick, erect cock and on her tight brown eye. Slowly, he eased into her. She was tight, tighter than he had expected. She grunted and groaned in pain as his thick cock entered her. He hesitated, not wanting to hurt this wonderful woman.

Feeling his hesitation, she pushed back taking some more of him into her slowly. "Oh, Dave..." she moaned. She smiled as he responded by grabbing her by the hips and pulling her towards him as he pushed in. It hurt and she grunted as her sphincter struggled in vain to push the invader out. She screamed into his pillow as he took her, stretching her well past the largest training anal plug she had so far tried. He stopped again and she looked over her shoulder at him, smiling through the pain. "It's okay Dave; Shelley said it would hurt the first time." Her eyes were tearing up as she spoke, seeing that this caused him concern she wiggled her ass and pushed back a little bit. "I want you." She said, and then gasped as Dave could no long restrain his passion and plunged into her.

He began pounding her ass, his ball sack slapping against her's. Slowly, it started feeling good as her sphincter relaxed and his head rubbed against her prostate. Her moaning softened from one of pain to one of pleasure. Recognizing that he was no longer hurting her, he began pulling out only to thrust back in harder than before. He was moaning as her ass was now comfortable tight on his cock. "Fuck, Tiffany!" Was the only warning she got as he swelled inside her and let loose a hot stream of cum deep inside her. The sensation was too much, she came, spraying her honey all over his bed.

Satisfied, he pulled out quickly. She squealed suddenly feeling herself empty but full of cum. Holding her hand close to her ass, she quickly a lighted to the bathroom and shut the door. It caught Dave as funny and kind of cute. He began laughing. While the sound was music to her ears, that it was directed at her predicament made her blush with embarrassment. "Don't laugh at me!" She yelled through the closed bathroom door.

"I'm sorry," he said from the other side, "can I get you something to sleep in?"

He could not see her face, but she was beaming, happy that he wanted her to stay. "Yes please...and my panties."

He brought her one of his old dress shirts. He had lost some weight since the divorce, as well as toning up. So when she came back to bed after cleaning herself up, it hung loosely on her so she looked like any woman coming to her man's bed wearing her shirt. "Thigh highs?" She asked. "Leave them on or take them off?"

He had always wanted his ex-wife to sleep in nothing but thigh highs and loose shirt. Now it was his turn to beam, this was the woman of his dreams. "Leave them on." She said nothing but smiled as she slid into bed next to him. He took her into his arms and held her close, smelling her hair and perfume. He kissed her good night. "You're beautiful." He said.

These words echoing in her ears, she smiled as she fell asleep in her new lover's arms for the first time.

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