tagTranssexuals & CrossdressersDawn's Diary Ch. 02

Dawn's Diary Ch. 02


The month before I was due to go back to San Francisco on business went slowly as I thought about the incredible fucking that Sam had given me and the prospects of another, even more adventuresome trip. I hoped that the next trip would again find me with Sam's dildo up my ass. The anticipation kept me in a constant state of excitement, even though I jerked off regularly with my vibrator up my ass.

Wanting to be my sexiest, I found a cute skirt and sheer blouse to wear while with Sam. I paired these with a lacy black bra, thong panties, a garter belt and stockings. Finding shoes that fit was a challenge, but I finally located and ordered a pair with 3-inch heels. Given the experience with Sam, my confidence and willingness to risk allowing others to know how I was dressed also prompted me to order larger breast enhancers.

I called the number that Sam had given me a few times, but she didn't answer. On my last try to reach her, I left a message letting her know when I would be in town. When the day of my trip arrived, I carefully packed my purchases and headed back to the city. I didn't dare wear a bra or camisole under my business clothes during the day, but I did wear a thong, the garter belt and stockings. The feel of these under my suit pants provided a constant reminder of Sam and the anticipation and wonder about what she would do to me made concentration on business a challenge.

When I arrived back at my hotel room that evening, I carefully shaved my entire body to be sure that there not even be a hint of stubble. I lightly spread baby powder over my cock and ass to sooth the irritation of such a close shaving. I put on the lingerie, inserted the new size C breast enhancers into the cups of the bra, and put my business suit back on. When I looked in the mirror, I could see the faint outline of the camisole and my fake breasts were clearly pushing against the front of my shirt. I momentarily considered changing into something that would better hide my femininity, but thought again about what I hoped would be another adventure with Sam and headed out the door to find dinner.

I walked a few blocks to a local restaurant encountering several people along the way. Two young women who I met on the sidewalk seemed to stare at my chest as they approached and I could hear them whisper and giggle after they passed, but I couldn't be sure that they had noticed my breasts or if it was something else that sparked their interest. Seated in the restaurant, I ordered dinner and looked around to see if anybody was staring at me, but all of the other patrons where engaged in conversation and didn't seem to be paying any attention to me. I thought I caught the waitress staring at the front of my shirt a couple of times as she served me, but she didn't say anything. As I sat eating my dinner, my excitement slowly grew in anticipation of seeing Sam.

I headed back to the hotel bar, sat down at the table where I had met Sam the previous month and looked around. She wasn't there. Another waitress came took my order. When she returned with the drink, I asked if Samantha was working. The waitress said that Samantha had arranged to take the evening off. As I sat sipping my drink, a month's anticipation crashed down and I pondered what I should do. I began wondering if the encounter with Sam would ever be repeated and considered going back to my room jerk off in solitude.

I finished my drink and the waitress came over to me table and asked if I wanted another. I was unsure. On one hand, I wanted several more drinks to drown my disappointment that Sam wasn't there. On the other hand, I considered just going back to my room to relieve the tension that had built up in my cock. However, before I could make a decision, Sam walked in carrying a briefcase and sat down at my table. She was dressed in dark slacks with a white shirt. The top button of her shirt was unbuttoned and a tie was knotted loosely around her neck. But for her astonishing beautiful face, she could have passed for a man. She reached over to me as if to straighten the lapel on my jacket and let the back of her hand slid down over my bra.

I don't know if the waitress noticed the curve of my breasts under the press of Sam's hand, but she smiled and winked at me. After ordering drinks for both of us, Sam explained that she had been quite busy and had not been home much. However, she had received my message and had arranged to take the night off so that we could have more time together. We finished our drinks and asked for the bill that Sam quickly took and paid. Sam put her arm around my waist as we started out the door of the bar, making me feel even more feminine. The waitress bid us a good evening and urged us, "Have fun."

Once in my hotel room, Sam didn't waste any time. She told me to take my cock and to kneel in the middle of the room. She handed a glass to me and told me to jerk off into it. I had expected her to fuck and fondle me as she had previously done and was confused by her instructions, but did as she said. I took the glass with one hand, pulled my cock out of my pants with the other and started pumping. After the long month of anticipation, it did not take long before my semen was spurting into the glass. Sam told me to take the cum filled glass into the bathroom and to leave it on the counter. She smiled as I pulled my new skirt, blouse, and shoes from my suitcase before departing.

When I emerged from the bathroom, Sam was sitting in the reclining chair with her feet up watching the television. She told me to walk across the room and turn around so that she could inspect the way that I was dressed and the manner in which I walked. As I began following her instructions, she corrected me telling me to stand up straighter with my shoulders back so as to better display my breasts and to let my hips wiggle back and forth as I walked. Once she was satisfied that I was sufficiently feminine, she told me to walk over and stand beside the chair in which she was seated.

Sam reached up and fondled my breasts commenting on how nice and firm they felt. She then ran her hand up over my stockings, across the straps of the garter belt, and finally under my thong to the base of my cock. She complimented me on how nice I looked and how smooth and silky my hairless skin felt underneath my lingerie. Sam then pointed out the flask that she had placed on the table and told me to pour a scotch on the rocks for her. I realized that I had not filled the ice bucket in the room earlier and apologized for my oversight. Sam assured me that that was not a problem and that she could wait until I did so now.

I suddenly realized that Sam had just elevated the risk and excitement of my private femininity. Up to this point, I had always keep the lingerie that I worn mostly hidden when in public. Although I enjoyed the excitement of wondering if the lingerie and my fake breasts were detectable, I hadn't allowed them to be blatantly visible. The ice machine was at the other end of the hall and Sam clearly expected me to walk down there dressed as I was to get ice. I meekly agreed.

I slowly opened the door and peeked out into the hallway. Thankfully, nobody was there. As I started to step out into the hall, Sam reminded me to walk with my head up, my shoulders back, and to wiggle my ass. I, of course, did my best to follow her instructions. I made it to the ice machine without seeing anybody else in the hallway. With the ice bucket filled, I had just started back down the hallway toward my room when I heard the elevator doors open. The elevator lobby was in the middle of the hotel, halfway between the ice machine and my room. As I slowly walked down the hall, hoping that nobody had gotten off the elevator, a middle-aged man and woman came around the corner and immediately spotted me walking their way.

They looked at me nervously and then continued walking toward me. I could feel their eyes as they stared. I tried to look past them as I headed toward my room but knew that both of them where checking out my breasts, my short skirt, and my stocking clad legs. The hallway was narrow and their eyes continued to wander all over my body as we passed. I didn't hear anything and couldn't tell if they had stopped to watch me as I continued toward my room still doing my best to walk as Sam had instructed. When I finally got to the door of my room, I allowed myself to look back down the hall. The couple had stopped and were looking at me. The woman smiled and gave a little wave of her hand. I reciprocated with a nervous wave and smile, opened the door, and was finally back to safety in my room where Sam was patiently waiting.

I carefully filled a glass with ice, poured the scotch fro Sam's flask, and delivered the drink to Sam. She then told me to kneel at her feet and remove her shoes. Sam had gone all of the way with the masculine look and was wearing men's oxfords. Once I had removed her shoes, Sam asked me to massage her feet. I eagerly complied with her request and she continued to slowly sip her drink as I slowly rubbed first one foot and then the other. After handing the empty glass to me, Sam got up from the chair, picked up her briefcase and walked into the bathroom.

When Sam emerged from the bathroom, she was clad only in boxer shorts and a tank top undershirt. Just had been the case in our previous encounter, a dildo protruded from the front of her boxers, but this one was different. It was larger and it seemed to have small hole in the head. Sam returned to the chair in which she had been sitting and told me to pour her another drink, which I quickly delivered to her. She then told me to kneel in front of her. She grabbed the back of my head, pulling it to her, and saying, "Suck my cock, you little wench."

I eagerly took the dildo into my mouth and, with her encouragement, was soon vigorously pumping my head up and down. This dildo almost completely filled my mouth and, as I pulled my head back so that only the head was in my mouth, I could feel the hole in the tip with my tongue.

The pumping action of the dildo in my mouth must have caused the base to rub on Sam's clitoris because she soon was moaning with excitement and I could feel her body become tense. She crossed her legs across my back and pumped my head up and down with increasing urgency with her hands. With one big final thrust that drove the dildo clear to the back of my mouth, she sighed deeply, and reached down to her side with one hand.

I felt a salty liquid squirting into my mouth from the head of the dildo. I immediately recognized the taste. It was the same as the cum that I had licked from Sam's fingers during our previous encounter. The dildo apparently had a reservoir that Sam had filled with my cum while she was getting ready in the bathroom. With one hand, Sam continued to slowly guide my head up and down forcing the dildo to continue slide back and forth over my lips while pumping cum into my mouth with the other hand.

With a mouth full of dildo and my own cum, I finally had to swallow. When she allowed me to pull my head back far enough so that the dildo was no longer in my mouth, she said, "Lick my cock and make it nice and clean."

I carefully ran my tongue over the dildo making sure that the last vestiges of my cum were gone, and swallowing all of the thick salty goo.

When her orgasm had subsided and I had licked the last of my cum off of the dildo, Sam asked me to get her another drink. I promptly refilled her glass with ice and poured another shot of scotch from the flask. When I gave the glass to her, Sam told me to kneel again in front of her. She wiped a couple of droplets of cum from my chin and telling me, "We don't want any of this to go to waste," made me suck the last of my cum from her fingers.

As she slowly sipped her drink, I nervously glanced down at the dildo that was protruding from her boxer shorts. Sam assured me that it would soon be lodged in my ass and asked me if I had ever been fucked with a real cock. I assured her that I had not. She asked me if I had considered getting fucked by a man. I told her that, while I liked dressing up and loved the feel of her cock in my ass, I was not attracted to men.

Sam said, "Good. I can give you all of the cock that you need."

Sam finished her drink and put the empty glass down as I continued to kneel in front of her. When she got up from the chair, the dildo passed enticing close to my face and I tried to take another taste of it as it went by. "Maybe later," Sam said, "but that's not what I have in mind right now."

Sam walked around behind me and pushed my shoulders forward so that my upper body was resting on the seat of the chair that she had just occupied. The chair had the faint musty smell of her sex and I immediately felt my cock begin to stiffen with excitement. I felt Sam pull the hem of my skirt up exposing my ass. Then I felt her tug the strap of my thong panties to the side. Sam complimented me on how well I had shaved observing that even the area around my puckered, waiting asshole was cleanly shaven.

I felt a well-lubricated finger enter my ass and I moaned, "Fuck me, Sam, please fuck me."

Sam responded, "You're a horny little bitch aren't you. I'll fuck you. I'll fuck you harder than you've ever been fucked."

She removed her finger from my ass. For a brief moment, I felt the dildo pressed up against my asshole before Sam drove her hips forward burying the huge rubber cock to the hilt. I let out a sharp cry at the pain of such a large intrusion. Sam keep her hips pressed forward and slowly caressed my buttocks as the pain slowly subsided. After a couple of minutes, Sam started to slowly fuck me. The pain had become pleasure and I responded to her thrusts driving the dildo deep into my ass and then pulling back so that only the head remained embedded. Sam increased the tempo and started moaning softly. As the pace of her thrusts quickened, she reached around me and grabbed my erection still encased in my thong and started pumping. It did not take long for the dual pumping action of the dildo in my ass and her hand on my cock to bring me to orgasm.

As my cum seeped through the thin fabric of the thong onto her hand, Sam said, "That didn't take long you little wench, but we're not going to stop now."

Sam continued to pummel my ass with the dildo faster and harder moaning her pleasure as the base pressed against her own sex. Her body finally shook with ecstasy as she came. The pumping of the dildo in my ass slowed and she leaned forward placing her fingers in my mouth. I could taste the salty remains of my orgasm. I was in a state of bliss there kneeling on the floor with the dildo up my ass licking my cum from Sam's fingers. Finally, Sam slowly pulled back and allowed me to straighten up. I turned around and Sam smiled. "I think you like my cock. I'm looking forward to fucking you again."

I said, "I'll be back in town next month. I can hardly wait."

Before Sam left my room, she made my write my measurements and clothes sizes on a piece of paper that she tucked into her briefcase. She told me that she would be dressing me for my next experience and that I should be sure to leave a key to my room at the front desk for her the next time when checked in. She then gave me a light kiss on the cheek and disappeared out the door leaving me spent and wondering what my next trip would bring.

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