tagTranssexuals & CrossdressersDawn's Diary Ch. 03

Dawn's Diary Ch. 03


Back at home it took nearly a week before I was able to sit comfortably after my encounter with Sam and her huge dildo. My thoughts constantly drifted back to her. I continued to keep my body cleanly shaven and regularly wore the outfit that I had worn that evening with Sam around the house. I bought a butt plug and inserted it on arriving home most evenings to ready myself for the experience to follow.

Relaxing at home, I would let my hand wander down to my lace-covered cock. It never took long before streams of cum were soiling my panties. Remembering the taste of my semen erupting from Sam's dildo, I would lick my fingers clean. I wondered what Sam had in mind for our next encounter and knowing that, whatever it was, it would raise my sense of risk and level of excitement.

The month finally passed and I arrived in San Francisco for another round of meetings, and a longing to again see Sam. I checked into the hotel and left a key for Sam at the front desk as she had instructed.

I had difficulty concentrating on business as I sat through the many meetings that day. Each time I caught myself thinking of Sam in anticipation of the upcoming evening I would realize that my cock was straining against the front of my trousers. I would hastily cross my legs for fear my erection would be noticed.

Finally, with the last of my meetings concluded, I headed back to the hotel. Sam was in my room when I arrived. She was sitting in a chair watching television, a drink on the table beside her. She wore a pair of gray slacks, a white shirt and tie. There was a sports coat folded neatly on the bed. I knew that the coat wasn't for me.

Sam cooly looked my way. "Hi, Dawn. I've been looking forward to seeing you again."

"Sam, you've been on my mind every day since you so thoroughly fucked me last month," I responded.

Sam told me to fix myself a drink. As I poured scotch from the flask that she had thoughtfully brought, she told me that my clothes were lain out in the bathroom and that I should shave myself to be sure there was no trace of stubble anyplace on my body before putting them on. I, of course, eagerly embarked on my assignment.

Once in the bathroom, I discovered the lingerie that I would be wearing. Sam had selected a red lace outfit for me. She had also supplied me with breast enhancers that were much larger than those that I had been wearing. "There will be no hiding those under my shirt," I thought.

I exercised extra care in shaving as Sam had instructed, taking pains to be sure that I removed all evidence of facial and body hair. I pulled on the red lace thong and could already feel the pressure of my cock against the fabric. Next I put on the bra and inserted the breast enhancers that completely filled the D-size cups. A red camisole and garter belt completed the outfit. I looked around for stockings, but could find none. Did Sam forget them?

When I emerged from the bathroom, I asked Sam if she had forgotten my stockings. She said, "No, you're not ready for them yet. Come over here."

Following her direction, I walked to her, doing my best to seductively wiggle my ass, the straps of the garter belt swinging freely against my legs. She continued to beckon for me to walk toward her until finally I was straddling her legs, my knees firmly pressing against her chair. "Let me play with your clit," she said as she started rubbing the front of my panties. "You like that don't you. You're quite a horny little wench."

I could only moan with pleasure. My cock immediately hardened and, with all the anticipation of this moment, it only took a few strokes of Sam's hand before I panted, "I'm coming."

Sam quickly pulled the head of my cock from my panties and caught my erupting cum in a glass. As I stood there, barely able to keep my legs from buckling, I wondered how long it would be before I was gulping down the salty contents of the glass. When I regained my composure, Sam arranged my cock back inside my panties.

"Sit down," she said pointing to a chair facing the large mirror on the wall. "It's time to get ready for dinner."

Sam pulled a makeup kit from her briefcase and expertly applied bright red nail polish to my toenails and fingernails. Cautioning me to let the polish dry, she continued working on me adding red lipstick, eyeliner, and mascara. Then she placed a wig on my head and carefully arranged the strands of hair. "You are very pretty," she said.

Looking at myself in the mirror, I had to agree with her.

Sam opened the closet and began to retrieve the rest of my wardrobe for the evening. First she brought out pair of black fishnet stockings, which she helped me pull on and fasten the straps of the garter belt. Next came a pair of black shoes with open toes and heels that appeared to be about 5-inches long. Sam knelt down in front of my chair to help me get the shoes on and to fasten the straps around my ankles. Then she told me to stand up. I had some difficultly doing so. I had managed with the 3-inch heels that I had worn last month, but these felt much less stable. Sam had me walk across the room a few times which I did somewhat wobbly. When Sam was satisfied with my ability to walk in the heels, she told me to spread my legs and bend over. I, of course, immediately complied, resting my hands on my knees for support.

As I stood in this compromising position, I felt Sam pulling the strap of my thong aside and pressing something against my asshole. As she pushed the object into my rectum, Sam said, "This butt plug will help your posture at dinner tonight."

After being painfully stretched around the perimeter of the butt plug, my sphincter finally closed around the base and Sam allowed me to straighten up. Having the butt plug firmly buried in my ass did help my posture prompting me to shift my hips forward and to pull my shoulders back.

Sam pulled a sheer white blouse with lace trim from the closet and handed it to me. I quickly put it on and buttoned the front. The blouse was cut fairly low in the front and my red camisole was clearly visible through the fabric. If I didn't know it before, I knew it now--there would be no hiding my secret femininity tonight. Anybody who saw me would immediately know. Sam then helped me put on a short black skirt. I was still unsteady in the heels and rested my hand on her shoulder as I stepped into the skirt that she held for me. The hem of the skirt pressed around the middle of my thighs forcing me to move with short steps as I again walked across the room for Sam's inspection.

She smiled appreciatively at her creation and reached out to trace the contours of my breasts, then my hips, and finally my buttocks with her hands. "You are incredibly sexy, she said. "I hope I don't lose you to another man tonight."

I smiled and assured her that she needn't worry. Her comment though raised a fleeting worry for me as I wondered for a moment if she, in fact, did plan to lose me to another man tonight. The misgivings only increased the excitement and, of course, I knew that I had no choice but to do as Sam instructed.

Finally, Sam handed a sweater to me that I slipped on and carefully buttoned as she retrieved her jacket from the bed. "We have reservations at a quiet little restaurant a couple blocks from here," she said. "We will walk."

Sam noticed that I had buttoned the sweater and said, "I don't think it is that chilly outside," as she unbuttoned it and arranged the lapels to clearly display my sheer blouse with the camisole underneath and the distinct bulge of my fake breasts against the fabric.

Because of the heels and the apprehension of going out, I wobbled slightly as I started to follow Sam to the door. She smiled and took my hand as we entered the hall and rode the elevator to the lobby. I was relieved that we didn't see any other guests, but as the elevator doors opened to the lobby, I knew that this was the moment of truth. I was filled with apprehension because I was finally stepping into a very public place for the first time dressed as a woman. Sam's soft squeeze of my hand and the excitement kept me from retreating to my room.

The desk clerk was busy with paperwork as we walked through the lobby and for a brief moment I thought we would pass by her undetected. "Good evening, Robin," Sam said.

The desk clerk looked up and smiled. "Good evening, Sam. I hope you two have a nice dinner."

Last month, the waitress in the bar had seemed to know about my feminine attire when Sam had brushed the back of her hand across my breast. Now the desk clerk was taking the way that Sam and I were dressed in stride. Did they also know how thoroughly Sam was fucking me? I was flush with embarrassment as we continued out onto the street, but I also felt a slight tightening of my cock against the confines of my panties as the excitement of exposing my femininity in public grew.

The people who we met on the street appeared confused, as they looked first at me, then Sam, then back at me. I tried to ignore them, but I knew that they were staring at me. Sam was talking to me, but my mind was spinning and I couldn't concentrate on what she was saying. The butt plug that was firmly lodged in my ass forced me to walk erectly with a sexy sway to my hips and with my fake breasts bulging out. With the way people looked at me, I began to understand what women mean when they describe somebody as undressing them with their eyes. After people would pass by, I would hear their nervously laughter and whispers and I could feel their stares at my back. I wondered what they were saying about Sam and me.

We finally arrived at the restaurant. It was fairly busy with most of the people appearing to have just stopped off after a day's work. It was quite warm inside and the men had removed their jackets and rolled up their shirtsleeves. Most of the customers were involved in spirited conversation, but things quieted considerably as Sam and I were shown to our table. I tried to ignore the many stares that I knew were focused on me as I followed the maitre de past the crowded tables.

Our table was right by the windows so that we were able to watch the passersby on the street and, of course, they could see us. Sam was a perfect gentleman as she helped me with my chair. As I settled into my seat, the sharp pressure of the butt plug reminded me to maintain good posture. Sam then reached to help me remove my sweater. I briefly resisted, knowing that removing it would even more clearly expose my femininity to the other customers and to the people walking by on the street. But, of course, the sweater was soon hanging from the back of my chair. Sam removed her jacket and sat down across from me. Smiling, she reached across and softly took my hand.

I could sense the other customers as they would steal glances our way and then whisper among themselves. I was becoming accustomed to that and was soon concentrating on the menu. When our waitress came over to take our order, she greeted Sam by name. Then she smiled at me and said, "You must be Dawn. You are as pretty as Sam said."

I felt the flush of embarrassment as I realized that Sam had told her about me and again wondered about how much Sam had told her. "Don't be embarrassed," she said. "You are making Sam very happy."

Sam ordered a bottle of wine and our dinners. As we sat eating, drinking, and talking, I began to forget the compromising situation in which Sam had put me, or perhaps in which I had put myself. Periodically, I sensed that the other customers were glancing our way and I noticed several people staring at me as they walked by on the street. I'm sure that one couple walked back and forth staring at least four or five times. However, as time passed and after a few glasses of wine, I had almost forgotten that I was a man and I proudly sat across from Sam as her sexy date for the evening.

We finally finished dinner and Sam paid the bill. As we left the restaurant, I was still quite warm, so I carried my sweater over my crossed arms. Sam wrapped an arm around my waist, her hand resting softly on my hip. As we walked down the street, I proudly held my shoulders back forcing my breasts to press against the front of my blouse and letting my hips wiggle in as enticing a manner as I could. As each person that we met on the street would stare at us, Sam and I would exchange smiles and soft giggles as we walked back toward the hotel.

Robin was still at the front desk when we arrived back at the hotel. "How was your dinner," she asked.

"Delightful," I said. "Sam is treating me to a beautiful evening."

"Wonderful, you two have a nice night."

We walked to the elevator and, as the doors closed, Sam took me in her arms and gave me a deep kiss. I felt her hand slowly move from my waist, up my side and around to my breast. I willingly surrendered to her touch and let out a soft moan of excitement. For a few moments, I forgot that I was a man, but the pressure of my rising cock quickly reminded me. Sam felt it too, smiled, and kissed my again. We broke our embrace when the elevator stopped at our floor. When the doors opened, I saw that another couple was waiting. It was the same couple that had seen me in the in the hall last month. I nervously returned their smiles. I guessed that my lipstick had smeared during our embrace and I knew my erection was bulging out against my skirt. I was sure that I saw them both glance down at the bulge. As Sam and I continued toward my room, I wondered if the couple had any idea of how badly I wanted Sam to fuck me or how thoroughly I was about to be fucked.

The door had barely closed behind us when Sam again took me in her arms, then with me backed up against the wall, her hands explored my breasts, my ass, and the bulge in my crotch. The sexual tension was intense and I could feel the cum almost ready to explode from my erect cock. Sensing my approaching orgasm, Sam abruptly stopped and told me to remove my blouse and skirt while she retired to the bathroom. I was becoming increasingly aware of the butt plug that was still planted firmly in my ass and I asked if I could remove it. Sam responded, "Not yet."

I undressed as she had instructed and sat down on the side of the bed waiting from her to emerge from the bathroom. I, of course, was not surprised when she opened the door and slowly walked toward me, the now familiar dildo jutting out from her boxers. "Lie back," she said.

Sam straddled my head and lowered herself down onto my face. I eagerly licked the inside of her thighs then went to work on her crotch. I worked her boxers to the side with my tongue and was able to reach up toward her sex, but the straps of the dildo prevented me from licking the lips of her pussy and I instead found myself licking the fake balls of the dildo. Although I was not able to truly give her oral pleasure, the friction between my face, the straps on the dildo, and her clitoris were clearly exciting Sam. She soon started to moaned and drove herself down on my face as she continued to rock back and forth faster and faster until I felt her shudder with an orgasm.

She then bent forward into a true 69 position that finally gave my mouth access to that wonderful dildo. I eagerly took it into my mouth and felt Sam's hips undulating up and down as she fucked my face. "Would you like me to lick your pussy," Sam said. I couldn't really respond with the dildo jammed almost down my throat, but Sam must have assumed that my answer was, "Yes" because I soon felt her warm tongue tracing the outline of my raging erection through my panties.

We continued to lick and suck until I couldn't hold the building pressure in my cock any longer. As the cum erupted from my cock thoroughly wetting the front of my panties, I tasted my own salty cum being ejected from the reservoir in the dildo and filling my mouth. I eagerly gulped it down as Sam continued to work her tongue against my wet panties. Sam finally rose up off of me, pulling the dildo from my mouth. She turned around giving me a deep kiss, and another taste of my cum that lingered in her mouth. With Sam's body pressing down on mine, we rested there on the bed in a deep embrace.

I was beginning to doze when Sam told me to go into the bathroom to remove the butt plug and change into something more comfortable. When I got to the bathroom, I discovered a black baby doll negligee that Sam had left for me. I quickly removed my shoes, stockings, camisole, and panties. I was finally able to relieve my ass from the pressure of the butt plug. Remembering the pleasure that Sam's caresses of my tits gave me, I left my bra on as I pulled the negligee over my head. I paused briefly to check myself out in the mirror and realized that my wig was gone, lost in the frenzy of our oral lovemaking on the bed. My makeup was badly smeared so I quickly washed my face, removing most, but not all of it. I was anxious to rejoin Sam, so didn't spend any more time than necessary.

When I emerged from the bathroom, Sam had turned the lights down and was in bed. She beckoned for me to join her and, as I crawled between the sheets beside her, I felt the dildo pressing against my thigh. Sam slowly ran her hand across my stomach, up to my breasts, and down to my leg, avoiding my cock that again had started to stiffen. Sensing my growing excitement, Sam gently pushed me onto my side with my back toward her. As she continued to caress my body, I became aware of the dildo pressing against my buttocks. I willingly shifted my body and slightly raised my leg to help guide it home.

"You're still horny aren't you," Sam asked.

"Yes," I said. "I have waited a month for you to fuck me."

"I've waited a month to fuck you, my sweet little wench."

I shuttered as my asshole finally yielded to the pressure against it and Sam pressed her hips forward burying the dildo to the hilt. "I think you like my cock, don't you?"

I could only moan softly, but Sam could tell that my answer was, "Yes," as I pressed back toward her trying to drive the dildo further up my ass. Soon our hips were violently undulating back and forth as Sam would drive the dildo deep into my ass and I would press back against her trying to take as much of it as I could. Then Sam would withdraw the dildo until only the bulbous head remained in me, only to slam her hips forward, impaling me again and again.

I felt Sam's hand again exploring my body, first caressing my tits through my negligee, then running her hand down my stomach, lifting the hem of the baby dolls, and then back up across the smooth shaved skin of my stomach to my bra. She continued to massage my breasts until finally, I felt her hand move down again across my stomach to grab a hold of my erect cock. Sam continued the relentless pummeling of my ass and used her grip on my cock to guide me even more firmly back and forth to meet the thrust of her hips. I couldn't hold myself any longer. The anticipation of getting fucked again by Sam, the intense pleasure of having my ass so thoroughly violated by Sam's dildo, and the constant tugging on my cock soon caused the cum to well up in my balls and to erupt from my cock in pulsating streams.

Sam wasn't done. She continued to pummel me with the dildo and I quickly regained the rhythm of her hips pounding against my ass. Finally, Sam gasped, "I'm coming," and drove the dildo into me as deep as it would go. I, of course, met the thrust of her hips as best as I could reveling in the realization that I was Sam's girlfriend. I wanted to satisfy her sexual needs as completely as I could.

I was completely spent as I dozed off in Sam's arms, her dildo still planted firmly in my ass. I awoke to the light of early morning and was pleasantly surprised to find Sam still in bed beside me. I reached over to touch her and, as I ran my hand across her soft skin, discovered that she had removed the dildo. Sam slowly opened her eyes and smiled at me. "You are the sexiest person I've ever been with," she said.

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