A Year Ago Ch. 10


This is an evolving story of Sara's sensual investigation. Please review the first phases of her transition . . .


My afternoon plan was changed by Jenn's behavior. I couldn't stop thinking about what Angelica had said to her, "Go to your room and get ready."

My imagination was going wild, fueled by the other surprising statement, "be careful of his very nice cock."

She was somehow aware of her chef's member but Thomas had acted appropriately around me and in the car home. Angelica had assumed that I would try and get Thomas alone? Even after I'd told her I wasn't interested in Blair's physique?

I entered the bedroom to see that I'd left in such a hurry the large anal prick lay on the floor. Now my plan was to go to Nordstrom's for some addition work outfits and underwear. It would be after 3pm by the time I met Cheryl but I needed the clothes.

After a quick shower I dressed in a simple pencil skirt and blouse and my medium heels. I had to select a new pair of pantyhose since I not finished the wash earlier. I grabbed my bag and got the Audi started. Then I saw the small envelop on the passenger seat.

It was a sealed note from Angelica, "Thomas was able to get the car problem solved. He's very good at such things. The man always has the right tool when a girl needs one. If you need any further assistance please call or text him directly : 444-1212."

It was an unabashed offer to use her chef for whatever I needed. He was at my beck and call, his subservience more than clear.

I set the note down and started toward the store. I still wondered how she would discipline Jenn, but why was I so curious? Was it how I'd felt bossing the Maid in the car earlier?

Though I felt comfortable pushing when required to get something accomplished, handling Jenn was in a different realm. Was my anger the source of the stimulation or was it seeing her small nipples erect beneath her t-skirt the cause of my excitement? I wanted to understand the relationship she had with her Mistress. Maybe I wanted to also control her in some way. She was a beautiful woman who was now filling my mind.

WOW! Jamming the brakes hard I stopped just before the intersection. I'd almost ran through a red light and there was a police car heading the opposite way!

I put the thoughts of Jenn's body aside and focused on driving. I turned the stereo on to distract me. I remembered that I'd need to explain my name to Cheryl, or maybe not? How had she not noticed the name Michael on my credit card? Twice I'd used it to pay for my purchases.

As I approached her in the women's casual department she was folding and arranging a pile of jeans, "Hello Cheryl," I said smiling, "It's me Hallie."

She turned toward me and paused, "Well someone's been busy," she said as she took my hand.

I realized that during the passed two weeks I had affected many changes; my makeup, my voice, my breasts forms and I'd found something approaching a style.

"I need to tell you Cheryl that you were so helpful the last time I was here. I couldn't have found a better coach that afternoon. But now I need another suit and some other outfits."

Two hours later I had two new suits fitted and a huge bag of other ensembles and clothes. I also bought four pairs of shoes and some lingerie as well as three sets of earrings. I was nearly the only customer this afternoon.

"How will you pay for this Hallie? Will Michael's card be used again?" she said this so matter-of-factly.

Looking up she took my card, "We get quite a few women who shop on their boyfriend's account. It's not an issue. The bills are paid and that's all that the store wants."

Since she was honest I decided to correct her, "Listen and I hope you understand."

She stopped and looked to my face, "I am Michael, but I'm also transitioning to live as a woman. Two weeks ago when I was here I didn't know how much I would change."

She smiled and said, "Don't worry, I do understand,"

I interrupted her, "But you must know that your patience and care that afternoon was a god sent. My chosen name isn't Hallie though but Sara. I hope that you can still run the card."

She paused, "You can still sign Michael can't you?" she smiled and continued the purchase.

Returning to the Audi having added $3,500 to my card account I filled the trunk and picked up the note from Angelica.

Driving toward home I picked up my thoughts of Jenn. I again wanted this Maid; at that moment I wanted to have Jenn. I wanted to understand her behavior and what the relationship to a Mistress as about. Somehow I was becoming obsessed with the Maid but more the woman that Jenn was. I wanted to suckle at her breasts, to love her pussy.

My lust was strong as I entered the house and moved to the bathroom. I saw the toy on the edge of the sink. The day had been full of new events. I poured a glass of wine and sat on the sofa with my CPU and the new cock toy. I wanted to make this a special event though. I decided to shower and dress in my Spade dress and outfit. The toy would have me this evening.

I stopped before stepping into the warm flowing water. I hated using a shower cap but my hair was clean and a damp head wasn't comfortable. I reached behind and pushed the medium plug into my opening. The toy felt like it belonged there. I touched my fake breasts as I lathered my body. How long would I wait for real breasts to grow? Possibly a year? I was anxious to discuss the details with the doctor.

While dressing I realized I hadn't made a reservation of Monday night and I didn't want to rush for the morning appointment. I booked a room on-line near the office I would visit Tuesday morning. Returning to the bedroom as I walked passed the tall mirror I paused. The soft rose dress made me feel beautiful. I moved a little closer and studied how my legs and ankles looked in the 4 ½" strapped heels. I felt good but I needed to touch up my toe polish tomorrow. I wasn't wearing the cincher but I'd dropped another pound. As I did my makeup my thoughts returned to Jenn. Maybe her first smile the evening we met was the cause of my infatuation?

I put the DVD in the bedroom on with another Claire movie. The girl clearly loved it in her backdoor. Her moans filled the room as I pranced about removing and hanging my dress. I looked over my shoulder at my intended lover, the realskin cock stuck proudly into the air. He was waiting for me. I saw the woman in the movie opening the fly of her lover's trousers. I was wearing just my chemise and a matching thong but without a brassiere. Walking about with the full fashion hose and my sexy strapped heels I saw the toys and pillows on the bed. I had to get passed my anxiety of the act. The toy was going to love me, I would suck this cock, and I would let it fuck my body.

I got on my knees at the edge of the bed, my hand on the base of the cock. The position recalled my prayers as a little girl. I chuckled at the error, but my mind saw me in a nightdress!

Moving toward the phallus slowly I could watch the girl sucking on the screen beyond as I reached around and slowly removed the medium plug, replacing it with the stout one. Then my mouth opened and I extended my tongue to my faux lover. My saliva coated the long side of the cock. I watched as the girl beyond lick about the man's cock, me following her lead. She opened her mouth and the head of the penis passed her lips, just as my boy toy popped into touch my tongue. I held the slim shaft as I moisten the entire head. I was shocked when I saw my reflection of this action in the mirror on the opposite wall. I was sucking off the boy toy vigorously, the shaft now well inside my mouth. I saw the wanton lust in my deeply toned eyes but the feeling of the smooth cock toy on my tongue transported me.

I shifted my eyes back to the screen to watch the girl languidly licking and sucking off her lover. She would pump him with her hand as she sucked the end of him and then slide more into her mouth. I could only handle a few inches of my toy. Trying to get more inside my mouth I gag and withdrew the toy. Watching her I noticed how she had slowed as she slid more of her man passed her lips and tried the same. Now my mouth was full of cock and I sucked the phallus strongly. I watched her moved to the bed on her side and the naked man lifted her dark hose covered right leg and touched her tight back opening with the tip of his cock. He moistened her rosebud and pushed his finger inside.

My lube was near and I applied some to my opening and the toy. I pushed the thong panel aside and a moment later one finger passed my outer muscle and than a second slipped easily in. The girl on the screen was softly moaning as the man's cock was pushed inside her bottom. My hand was on the shaft of the toy as I slowly inserted the end, there was some pain as with the largest plug but the exercises had helped me relax to allow the penetration and now was that moment. Could I allow my body to accept this new naked cock within me? The toys had been there but this was a cock. Was I about to become a girl or just a cross-dressing fetishist?

The helmet of the 'boy' slipped passed my sphincter and I paused to catch my breathe. There was a little pain just leaving the toy still. It wasn't a large cock but it was inside me. I shifted it slightly and the boy toy slipped out. I was surprised how quickly I reached and pushed it back in, gasping as it entered more deeply. I tried this a second time and it slipped back in but deeper still. I looked to the screen to see the girl smiling as the man pushed deeply into her ass.

I wanted more of the toy but decided to add more lube. My fingers were slippery but this time when pressed at my opening the toy entered fully, the soft balls of the toy stopping further invasion. I rested with this new lover, smiling as I saw that on the screen they were pausing, she holding him back for a moment with her right hand. I waited for a minute and thought that this new experience was less difficult than I thought. The toy should have a name. If 'he' was going to be in bed with me I would call the boy toy Sam.

Sam and I rested for three minutes with me on my side and him nearly six inches deep within me. I was ready to explore, not just being penetrated but being fucked. The screen showed the girl now with her back to her lover and his cock deep in her bum as he pumped quickly back and forth. I shifted to my knees while holding Sam within me, then I slowly pulled him out slightly. There was no pain now and I pushed the cock back fully inside myself. Again and again I move Sam into my body and pulled him nearly out. The action seemed almost work like, and a bit awkward. I shifted and positioned him beneath me while I held him about the balls and rode up and down on his shaft. I looked to the screen as the girl did the same; she was fucking her man. Sam was taking me, bring me along to a new place. I watched the woman as I was fucked to orgasm.

In the morning I stood naked looking at the bed, my lingerie scattered about, my beautiful hose snagged. Sam had fucked me twice more last night. I smiled noticing the toy on the nightstand. Each orgasm seemed to get better but produced less semen. I needed to shower and to clean him as well but I felt empty. I found the long double head toy on the opposite side of the bed. It had been inside me as well. I retrieved the small plug and inserted it.

In the shower cleaning the toys and myself I considered my day. I'd planned to leave for the City at 2pm so I couldn't dilly-dally. A simple breakfast and packing, then I'd stop at the office to check the server.

Arriving at the building I met Avery outside. I'd explained my plan at the party Saturday evening.

"You're headed to see the doctor tomorrow? Don't feel embarrassed about why you're there. You are a woman and we need a different level of care."

I was a little anxious, "What if she laughs, or scolds me?"

Avery moved closer and hugged me, "No worries Sara. You are on an adventure and you need to adjust some things. Ask her for guidance and don't be immature. She sees many people who are going through a similar change remember?"

I kissed her cheek, "How Madison will be jealous," she said.

She kissed me back and patted my bum as she turned to get into her car, "Good luck Sara."

I drove silently thinking of the two week passed. No one had stalled my progress, nor interfere with my plan. Only strong support had been provided by all of the women I'd met, even Lynn. Her promise to not share the news probably didn't include Cynthia. But I hadn't followed up now five days later. I was thinking of last Wednesday night at the bar with Matt. Even he had given me a positive perspective. I worried that I hadn't spoke with Bill. He was my best friend, but we both didn't reach out regularly. I needed to get a hold of him soon. The text method may be the best.

I was happy I'd booked at the Hyatt. I could get a simple meal and not have to leave my room. I settled my outfit for Tuesday, pantyhose with white lace underwear and the red dress with my black leather medium heels. The mini bar had a small bottle of wine and it was a good evening just thinking of my day and where I had come from.

I slept well past the alarm; I had set the level too low.

Getting clear of the hotel I would leave the Audi here and walked the two blocks. The office was in a nice low-rise building less than a quarter of a mile from the hotel. I just had to stop at the front desk.

Exiting the elevator I glimpsed an old associate from my previous employer walking right toward me. I'd booked here because I had used the hotel previously. It was Jake, a hardware designer, but he was with two others, now maybe fifteen feet away. Maybe I could just walk passed unnoticed. I did so and headed to the desk to checkout.

I was standing at the desk looking in my bag for my wallet, "Excuse me Miss. Don't we know one another?"

Jake was at my side, I turned and looked directly at him, "No, I'm sorry, I don't recall."

He smiled and stepped back a bit, "Yeah, uhm, I've mistaken you, for someone else. I apologize Miss."

He moved slowly away, but looked over his shoulder, twice. He'd recognized me but was being polite.

I moment later my phone buzzed. He was trying to reach me. I made a split second decision to not turn, not allow him to confirm it was me going for my phone. I was glad I kept the ringer off and didn't even flinch as I spoke with the agent.

"Do you need to get that call?" the woman asked.

I was a little nervous. Jake was clearly gone. I slowly turned to confirm that the elevator door had closed. My life was still so unsettled.

I looked back to the agent, "No I'll deal with him later, that call can wait. I would like to leave my car in the underground parking until this afternoon. Is that OK?"

Walking along the street to my appointment I realized there was little chance he hadn't known it was me. I could just let it pass or call and ask him to meet. Ask him to share my secret without broadcasting that he'd seen me. Seen me dressed as a woman. There was risk either way. I reached for the phone. I had an extra ten minutes and it would be better to control the information he might pass to others. We'd worked on two projects together and he clearly looked into my eyes.

Our old office wasn't near but the firm had moved into the neighborhood within the passed year. I pushed the re-dail.

"Hello Jake, it's me Michael. Yes, yes, I've been going through some changes since we last saw each other. But please don't laugh." He corrected his tone and was kind, his comments respectful.

I had a plan, "Can I buy you lunch later today? Maybe around 1:30pm?"

It was set. He would not tell anyone he'd ran into me for now. He agreed to respect my privacy and I would explain myself at lunch. There was a simple bistro a block from the hotel we'd had lunch at several times with business associates staying at the Hyatt. Meeting there made sense.

Hanging up I wished I'd had gotten out of bed earlier. My plan was to have a simple breakfast in the Lounge. I would possibly have missed seeing Jake. I had pushed the risk aside when I'd booked the room.

As I entered the doctor's waiting room a few minutes before my appointment I was surprised to find two other 'women' and a guy. I guessed I'd be waiting for a while.

Twenty minutes later I was alone; the guy had left with his girlfriend. She was actually quite passable. One of the femmes was also waiting for someone. Her friend came back into the waiting room. She was a tall girl, made even taller by her 4" heels. She wasn't unattractive but definitively not passable due to her height and size. 'Telly's' head almost touched the doorway as she and her smaller femme friend left the room.

I spoke with the other girl. She had initiated the conversation, "Don't tell me you're a 'boy'. I'll be beside myself."

I smiled and didn't provide my history. She talked and I listened for ten minutes.

"I've been transitioning for eighteen months. My breasts started to grow but too slowly. I had some modest implants done six weeks ago. My girlfriend loves my new titties."

She asked about my hair, "It's an amazing short do. I couldn't feel comfortable without a wig for well over a year. Now its all my own hair."

I asked, "It has taken over eighteen months for yours to grow to your shoulders?"

"Actually more like two years. I didn't cut it for six months prior to my decision. Sure Sara, and I eat all of the right foods, shampoo only three times a week. Excessive washing will cause you to lose length dear."

I was so out of touch with what most transitioning girls dealt with.

"Have you had any work done?" she asked.

"You mean to my body or face?"

She realized I hadn't, "I'm sorry to ask such a personal question. You do know that you're quite extraordinary Sara. To look like you do, without a wig and have that figure. No facial fem work, really? How much do you weight?"

I was tiring of her questions but was polite, then the nurse call for her. A few minutes later I was escorted to a room as well.

The nurse handled my chart and prepared a baseline of my vital information, took a blood sample and a urine sample. She also requested a semen sample, which I was surprised by.

"The Doctor will suggest that you have several stored for future use. Can you please remove for clothes and put the gown on Miss."

She left me alone with a collection of magazines. The lesbian porn one seemed most interesting.

As the doctor entered with my chart she spoke, "Sara, it's not typical for these consults to start this way, but, your transition is unusual. Without your test results we can only review the actual conditions. Your weight is perfect. Right on the slope for your height, for a woman. May I see you naked please?"

She stood watching, "and please remove the heels Sara."

She was of average height, maybe 5'-6", but she was in a heeled shoe. She was still an inch shorter than me standing barefoot. The silicone breasts seemed not to surprise her. She examined my chest then turned to look at my back. With her stethoscope she listened to my heart and lung sounds.

"I'd like to examine your anus. When was the last intercourse?"

I paused as I bent over and two of her fingers entered my opening, "Well, with myself only on Sunday, well, actually early Monday." I was blushing, "I've never been with a man."

"Please explain your cleansing method. Too aggressive can be harmful Sara."

Ten minutes later she leaned against the edge of the examine table, "Shall we start hormones today? I want you to try a new product, and let's assume we'll schedule an in-patient surgery for your implants for four weeks from today."

"So quickly? I had assumed you would require at least a year. Are these hormones safe, will they affect my sexual functioning?"

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