Mr. Wallace and Me Pt. 08-10

"Mmmmm," she murmured. "I've been wanting to do that all night."

After we reached the penthouse floor, Tina took my hand as we walked to her door. As soon as we were inside, she took off her trenchcoat, let it fall to the floor and crossed her slender, bare arms around my neck. My hands went to her bare midriff and I experienced the softest, most tender kiss anyone could imagine as she opened her mouth and ran her tongue over my upper lip. I couldn't believe this was happening. I wasn't sure what I was supposed to do, but as we kissed, Tina pressed her body against mine and started to moan softly, so I thought I must be doing OK.

After about a minute, Tina broke our kiss, put my right hand on her covered left breast and kissed me again. It was the first female breast I had ever touched, and it felt amazing.

"I'm going to change my clothes," she said. "Why don't you call your parents and tell them you won't be coming home tonight."

I nodded dumbly as she turned and disappeared into the bedroom. I found a phone in the suite and called home, telling Mom that I would be spending the night with one of my friends. She said that was OK and thanked me for calling.

A few minutes later, Tina stood in the bedroom doorway wearing only a tiny white teddie.

"I hope you don't think I do this with every man I meet," she said. "You're just such a nice guy, and I haven't met too many nice guys lately."

Tina slowly backed into the bedroom, motioning me to follow. She hopped up on the bed playfully and watched with a gentle smile as I rushed to remove my shoes, jacket, shirt and pants. I stood there in my black socks and white jockey shorts, my small penis straining inside.

"I'm not ... you know ... very big ... you know ... down there," I said to her, more than a little defensively.

"That doesn't matter," she said, giggling. "You've got an incredible body. It's so sleek. There's not an ounce of fat on it. I wish I had your skin tone, and I think your waist is even thinner than mine. Come here, silly."

I pulled my underpants off, moved my body atop hers, and we began kissing again, my hands clumsily exploring her body under her teddie. My mind was a blur, but I realized one thing: "I'm going to get laid."

Tina moved her teddie slowly over her head and off her body, and there were her firm breasts right in front of me. My mouth went to them, teasing with my tongue and teeth. This is what I had feverishly dreamed of all through my teenage years. I hoped I was doing it right. She opened her legs and I got between them. I pressed my lips against hers, and soon our tongues were playing. She was there under me, ready to be taken.

There was just one thing wrong. My penis had gone soft.

Here I was with the most gorgeous woman I'd ever seen ... and I couldn't get it up.

I moved off of her and started to apologize. She shushed me.

"It's OK," she said. "You just might need a little help."

Tina gently got me onto my back, moved so sexily onto her knees between my legs and gently grasped my soft four inches while planting tender, wet kisses on my hairless chest. It felt so good, but my damned penis got no harder. With the kindest smile I've ever seen, Tina bent over and took me into her lovely mouth, her hair falling over her face. It felt so wonderful.

But still, I couldn't get hard. It didn't help to remember that the first time I was at Mr. Wallace's house, I got hard the instant he put his lips on my penis.What was wrong with me?

Tina kept up her amazing sucking for a very long time, but finally gave up.

It was so terribly embarrassing. I apologized over and over again.

Tina put her arms around me and gave me a tender kiss.

"It's OK," she said. "I'm told it happens to all men sometimes. Besides, there are other ways to please a woman."

With that, Tina lay back and spread her legs. I noticed for the first time that she had shaved her pubic hair. She gently grabbed my pony tail and moved my face to the first pussy I'd seen since I was born. It smelled kinda strange, and when I licked it, it tasted terrible. I began licking rapidly and moving my tongue inside like I had read about in all those porn magazines and websites. Somewhere, I had heard that if you draw the alphabet with your tongue, it drives women crazy.

Tina seemed to be enjoying it, breathing hard and moaning, but it smelled awful and tasted worse. I kept it up as long as I could, but I wasn't the least bit horny while doing it, and finally stopped.

"I'm sorry," I said as I plunked down next to her on the bed. I was so ashamed of my poor performance, I almost started to cry.

"It's fine," Tina said, grazing my smooth chest with her fingernails. "You're probably just a little tired. It's all right. Bill, I'm just curous, though. Is this your first time with a woman?"

I thought I was going to cry. I nodded, "yes."

Tina smiled kindly. "I understand," she said, giving me a quick kiss on the lips. "We can try it again in the morning."

Tina put her teddie back on. I got under the covers naked. Still ashamed of myself, I turned my back to Tina and tried to sleep.Why had I gotten so turned on by those old, ugly men, but I couldn't keep an erection with the most beautiful, sexiest woman I have ever seen. A few moments later, Tina snuggled against me. I could feel her firm breasts against my back, her hands moving on my sides, her sweet breath at my neck.

"You're so smooth," she whispered. "I just love your hair, and you have such a wonderful body. It's so nice, almost like being with another girl."

Like another girl? I didn't know how to feel about that. She kissed my back, then turned over and went to sleep.

I hoped the morning would bring my virility back. When I woke up, I felt something wonderful down below. Tina's mouth was on my tiny penis, sucking slowly and tenderly. My organ responded, getting hard before I even had a chance to think. Her gentle hands were playing with my scrotum, and she was taking my whole four inches into her mouth. Finally pulling me atop her, Tina spread her legs under her teddie and kissed my neck, guiding my penis to her pussy. It was by far the nicest thing anybody had ever done for me. Here was this stunning, sensitive, fantasic girl doing everything she could ... and before I could enter her, my damned cock went soft again.

I rolled off her and covered my face with my hands. It was the most humiliating moment of my life.

Tina couldn't have been nicer, telling me that it was probably her, and not me, that I probably wasn't all that attracted to her. I told her that was ridiculous, that she was everything a man could want. I couldn't get dressed and out of there faster. Standing there looking like an angel in her teddie, Tina helped me on with my suit jacket and gave me a tender kiss on my cheek. She had a confident look in her eye.

"Don't worry," she said as I left the suite, "everything will be fine."

End of Part 8 (To be continued)

Part 9:

It was still only 6:30 in the morning when I went to reclaim my mom's car from valet parking. My necktie was still in my jacket pocket, where Tina had put it so seductively last night. The attendant, seeing me in my blue suit, gave me a knowing wink and asked me if I had a good time last night. He had assumed by the fact that I had checked the car last night and was leaving so early that I had spent the night having sex with someone. I nodded and gave him a fake little grin. Let him think what he likes. Why should everyone know that I couldn't get it up?

I went home and tried to reconcile what had happened. I had a really good time being with Tina, but what kind of man was I? Why could I reach orgasm dressed like a girl with aggressive old men, but not as a man with a woman any guy would give his left testicle to sleep with? Did it bother me just a little bit when we were together that everybody ogled Tina and I was ignored? I told myself "no, of course not," but ...

Would Tina say anything to Mr. Drummond about our date? What would I tell Mr. Drummond this afternoon when he asked me if I had a good time last night, as he most surely would?

Mom was surprised that I was home so early. I got to eat breakfast with her and Dad, mostly listening as they talked about Dad's work. Knowing I had to be at Mr. Drummond's office at 3 o'clock, I told Mom I had to work an early shift this afternoon because my supervisor wasn't going to be there. Mom said she didn't need her car, so it would be all right.

After breakfast, I went upstairs to my room to see if I had a fresh shirt to wear. Emptying my pockets, I noticed that I still had almost 450 dollars left from what Mr. Drummond had given me. Tina was not only beautiful, she was anything but an expensive date.

I showed up on time at Mr. Drummond's office, and the pretty receptionist told me to go right in, that "they are expecting you."

"They?" I thought.

Mr. Drummond, wearing an expensive-looking suit, met me at the door and closed it behind me. Sitting in one of the two chairs opposite his desk was an attractive, 40ish, slender woman with glasses and her brown hair in a bun atop her head. She sat there with her legs crossed in a fashionable turquoise skirt, a crisp, white blouse unbuttoned enough to show a hint of cleavage, and a form-fitting turquoise jacket.. Mr. Drummond introduced her to me as Miss Hendricks. She didn't get up as I shook her dainty hand and said hello before I sat down in the chair next to her.

Mr. Drummond sat in a big chair behind his desk, picked up some papers and read them for a few moments.

"Bill," he said, his face serious, "We've got something to talk about."

I worried for a moment that Mr. Drummond had found out from his goddaughter Tina that I had slept with her.

"Bill," he said, "I've got an interesting proposition for you. I want you to think about it seriously before you say yes or no, OK?"

Curious, I told him I would.

"Listen, Bill," he said, "The main office for my firm is in Chicago. That's where I do most of my business, and Chicago is where my most important client lives. This client has some -- well, he has some unique perspectives when it comes to his companions. I think that from what I've learned about you, Bill, I'd like you to come to work for me for a year in Chicago."

I was totally confused.

"Unique perspectives?" I asked. "What does that have to do with me working for you in Chicago? Mr. Drummond, I don't understand. What kind of work would I be doing?"

"Bill," he said, "you're a young person at a crossroads in life. Seeing you at Ted's house the last two weekends, I saw one of the most beautiful girls I have ever seen ... except you're a boy. Before making you this offer, I had to be certain that you were better suited to be in a female role than a male one."

I was still confused.

"Mr. Drummond, if this is about your goddaughter ..."

Miss Hendricks and Mr. Drummond exchanged a knowing glance.

"Bill," Mr. Drummond said, "I have a bit of a confession to make. Tina isn't my goddaughter."

My eyes got really big. I gripped the arms of the chair.

"What do you mean? You told me you were there when she was born. She told me all about you when she was growing up. I don't understand."

Mr. Drummond's eyes were kind, but his voice was firm, like the lawyer that he is.

"Tina is not my goddaughter," he said. "I never met her before Monday, when I hired her."

"Hired her?" I said.

"Bill," he said steadily, "Tina is a five thousand dollars-a-night escort. She's got a bachelor's degree in theater, and on Monday, we went over a script she could use involving growing up with me as a friend of her family. She's absolutely top of the line when it comes to this sort of work, and escorting is how she's financing getting her master's degree."

The room started to swim around me as Mr. Drummond continued, glancing down at the notes on his desk..

"I like you, Bill. I wanted to be sure that I was doing the right thing. Tina -- by the way, that's not her real name -- Tina has given me a full written report on your evening. It would appear that you ... well ... you had difficulty performing with this desirable, beautiful woman."

This was a nightmare. Mr. Drummond knew ... everything?

"Listen, Bill, if it makes you feel any better, Tina liked you. She reported that you're a -- he looked down at the paper in front of him -- a very sweet boy."

My eyes started to tear up. Miss Hendricks just sat there impassively with her impressive legs crossed. With a halting voice, I asked Mr. Drummond why he had gone to all that expense and trouble to embarrass me. Then I couldn't help it. I started to cry.

Mr. Drummond sighed and walked slowly around his desk, bent down and put a fatherly arm around me. It felt good.

"Listen," he said, "some people are just not meant for a traditional role. It would appear you are one of those people. As Bill, you're really not all that impressive, but as Billie ... my goodness, you're so incredibly special."

I sat there, Mr. Drummond's comforting arm around me as I tried to regain my composure.

"What is it you want from me, Mr. Drummond?" I asked as I wiped tears from my eyes. "What is this about a job in Chicago?"

Mr. Drummond's arm left my shoulder. He stood up and leaned back against at the edge of his desk, facing me.

"I want Billie, not Bill, to move to Chicago," he said. "My firm will pay all your expenses, your apartment, your meals, your transportation, your dresses, nightgowns, your makeup, training ... everything.

My dresses, nightgowns, makeup? My training?

"Billie," he said, "I've seen the effect you have on men. With the right clothes, beauty advice and training, you could be a great benefit to my law firm. I have a client -- a very special client -- who has an affinity for beautiful young women who have ... well ... a little extra. Eventually, I'd want you to meet him."

"You want me to sleep with some guy?" I said, angrily rising from the chair. "That's what this is all about?"

Mr. Drummond's face turned stern. His eyes bore into mine, immediately intimidating me and calming me down.

"I'm a lawyer, Billie, not a pimp," he said sharply. "No one expects you to sleep with anyone. All you will be required to do is to make yourself as feminine and attractive as possible and to attend the opera and some social gatherings where you might meet my client. Whatever might happen after that would be entirely up to you."

I sat back down, my mind in a whirl. Turning into a full-time girl? Wearing dresses, meeting men? Do I really want to do that?

"How can I move to Chicago?" I asked blankly. "What would I tell my parents?"

Mr. Drummond's face softened.

"Here's how it would work, Billie," he said. (I noticed that now he was calling me by the feminine Billie, instead of Bill.) "We'll tell your parents that because my old friend from Vietnam thought so much of you, I've decided in his memory to offer you the annual internship at my firm in Chicago. Next week, we will fly you and your parents to Chicago, put all of you up in a nice hotel and give them a tour of our facility. We'll tell them that while they won't see much of you except for a Christmas visit next month, if you finish the 12-month internship, you will receive a $50,000 college scholarship in addition to some excellent experience at a major firm.

"Oh, and one more thing, Billie, as executor of Ted Wallace's estate, I'll see to it that in addition to the scholarship money, at the end of a year, you will be the beneficiary of his $75,000 life insurance policy."

I thought for a moment. Mom and particularly Dad would jump at an opportunity like that for me.

Mr. Drummond went on.

"While you're in Chicago, you'll get a new name, a new identity, and once your female persona is settled, we'll give you a temporary job at the law firm to keep you from getting too bored."

My mind was racing. A new name? A new identity? That would help solve the problem of hiding from Dr. Phillips. But do I want a new sexual identity, too?

"Would I have to ... you know ... get implants or anything?" I asked.

Mr. Drummond smiled.

"No, Billie," he said. "We would put you on a regimen of doctor-prescribed hormones and exercise. Miss Hendricks here will be in charge of all that and of teaching you all about fashion and makeup and how to walk, talk and purport yourself as a young lady."

I looked at Miss Hendricks, who stood and with perfect posture slowly walked around me in my chair. Even though she wasn't a young woman, she oozed sensuality. Her breasts were still firm, her posture regal and her perfume subtle but attention-getting.

"She's even prettier than the pictures you showed me of her, Nathan," she said.

I realized to my shame that Mr. Drummond and Miss Hendricks must have seen the photos of me on Mr. Wallace's computer, and Miss Hendricks was referring to me as "she."

"She's so fresh and vulnerable, and that blonde hair is to die for. I can do a lot with her, Nathan. Give me two months -- 10 weeks tops -- and no man will be able to resist her."

I looked at Mr. Drummond.

"I don't mean any disrespect," I said, "but wouldn't it be better if ... well ... if a man who also dresses taught me?"

Mr. Drummond and Miss Hendricks exchanged knowing looks.

"Billie," he said, "Miss Hendricks is a crossdresser. She's a man."

I didn't believe it. I stared at Miss Hendricks, making a point to look for what tipped off Dr. Phillips about me.

"She can't be a man," I said. "She doesn't have an adam's apple."

Miss Hendricks turned to me.

"I've had what's known as a tracheal shave, Sweetie," she said softly. "It's a minor operation where a doctor shaves the cartilage that makes up the adam's apple. You can see what the operation looks like on YouTube. The operation is really no big deal. I had a sore throat for a couple of weeks, that's all. You can get the procedure done in Chicago if you like, isn't that right, Nathan?"

Mr. Drummond nodded.

Miss Hendricks stood next to me, took my left hand and placed it on her groin for a moment. There was no doubt that this person wasn't born a female. She gently stroked my hair, then sat back down in her feminine way, crossing her legs.

"As I said, Billie," said Mr. Drummond, "I don't expect you to make a decision right now. Go home and think about it. I'll be attending Ted's funeral at St. Mary's tomorrow and then leaving town to fly to Chicago on Friday, so I'll need your decision by then, OK?

I said, "OK," my mind a blur as I got up to leave. Mr. Drummond walked me to the door, his reassuring hand on my back. I paused and asked if Tina had said anything other than writing that I was a sweet boy.

Mr. Drummond walked to his desk and fetched the report Tina had written. He showed me the last paragraph she had typed.

"Bill is very likable, a gentleman," she wrote. "It's too bad he doesn't know that he's so much better-suited to please a man than a woman."

I couldn't believe that I had been manipulated so effectively by Mr. Drummond and Tina, or whatever her name is. My mind was swimming as I left the office building. I got into Mom's car and just drove off aimlessly. What was I going to do? Who ever had a choice like the one facing me? On the one hand, there was the scholarship, the cash, and being far away from Dr. Phillips when he searched for me. On the other hand, I'm a boy, not a girl.

I just kept driving, my brain spinning. An hour or so later, I came upon a shopping mall I had never been to before. With Mr. Drummond's $450 in my pocket, I decided to see if there were any video games there that I didn't already own. Inside, on my way to finding the video store, there was a big department store. I decided to go in.

End of Part 9. (To be continued)