tagTranssexuals & CrossdressersDawn's Diary Ch. 05

Dawn's Diary Ch. 05


I can't believe how fortunate I am that Sam found me and agreed to move in with me. We laugh about how we met. Sam told me that she was incredibly turned on when she realized that I was wearing lingerie that evening in the bar. She didn't know how I would react when she walked out of the bathroom in my hotel that night sporting a dildo, but Robin had told her that I was a regular at the hotel and seemed like a good guy. Sam said that she figured the worst case would be that I would tell her to leave.

I told Sam how concerned I had been that night about how she might respond on discovering my lingerie, but I had found her so interesting and attractive that I never considered declining her suggestion that we go to my room. I recalled worrying about how I was going to deal with my lingerie if it started to appear that we were going to be intimate, but before I could decide, she had walked out the bathroom wearing the dildo.

It only took us a short time before our arrangement started to feel so natural. Samantha is the perfect partner and housemate. She is funny and interesting and uninhibited. She is also sensitive and caring, whether she has my ass skewered on her dildo or my cock sheathed within her warm pussy.

I scheduled another round of meetings in the bay area. Sam went with me so that we could enjoy the city together and to pick up the rest of her things that she had stored in Robin's garage. We planned on leaving home after lunch for the drive so that we would be able to check into the hotel before going out to dinner.

The morning we were to leave, Samantha suggested that we shower together so that she could help me shave. As I stood under the shower, Samantha lathered up and shaved my armpits and the rest of my upper body. As she knelt down to work on my legs, my cock became semi-erect. It continued to harden as I felt Samantha slowly working the razor blade closer and closer to my crotch. Samantha had me turn around, spread my legs, and bend forward so that she could remove the hairs from the crack of my ass. As she rinsed the shaving cream from my ass, I felt one of her fingers enter my asshole. "Oops," Samantha giggled.

I instinctively settled down onto her finger and she drove it further home as she inspected my ass for stray hairs that she had missed. When she was satisfied that my rear was completely bald, she slowly extracted her finger and told me to turn around so that she could complete the job by shaving my pubic whiskers. By that time, my cock was rock hard and sticking straight out. She laughed as it almost hit her in the face when I turned.

Samantha immediately grabbed my cock with one hand as she first lathered and then shaved my balls. As she worked around the base of my cock, she pulled it first to one side, and then the other, then up, and then down. Her manipulation of my cock started having the expected effect. I let out a soft moan and started to squirm.

"Hold still or I might accidentally cut it off," Samantha said, but her laugh and increasingly exaggerated manipulation told me that she was enjoying my discomfort at trying to stifle an orgasm.

She also seemed to be re-shaving areas and I could feel her breath on my bare skin as she moved in particularly close to inspect her work. The pressure in my balls was building and it was becoming clear that Samantha wasn't in a hurry to finish the work of shaving me. Finally, I couldn't hold back any longer.

"Oh, my God, I'm going to cum," I gasped.

Samantha quickly took the head of my cock into her mouth. She looked up into my eyes and she slowly stroked the shaft. As my pulsing streams of cum erupted into her mouth, she closed her eyes and started gulping my salty goo down. The throbbing of my cock started to subside, but Samantha continued to hold it firmly in her mouth. Gently cupped my balls with her other hand, she milked the last of my cum into her mouth.

When she arose to her feet, she wrapped her arms around my neck and our mouths met. She thrust her tongue into my mouth and I could taste the remnants of my cum. When she pulled back, she giggled as she saw that some of the cum that had dribbled from her mouth had transferred to my face. She carefully licked it off. Then I licked the remaining dribbles of my cum from her chin and we shared another deep kiss.

I decide to return the favor and pushed Samantha back against the shower wall. She winced as her back hit the cold surface, but she quickly spread her legs to ready herself for my tongue. As I slowly dropped to me knees in front of her, I ran my tongue over one nipple and then the other. They were already hard with anticipation. My tongue trailed down across her taut belly toward her pussy.

Samantha spread her legs further and thrust her sex forward toward my approaching mouth. She was wet from the shower, but I could taste that her love juices were already flowing as my tongue slipped between the lips of her pussy and found her clitoris. Samantha moaned, grabbed my head pulling me toward her. As I went to work licking and sucking on her clit, Samantha started to ground herself against my face. Her moaning and gyrating hips became frenetic. Her hands were crushing my face against her sex. I was working her clit with my tongue. Finally, I felt her shudder with her orgasm. Her grip on the back of my head eased and I softly licked her swollen clit. Slowly, Samantha let her back slide down the shower wall until she was seated on the floor in front of me. I pulled her face to my chest and we embraced under still running water.

"Time to get you ready," Sam said as she jumped up.

We quickly toweled dry and Sam sat me down in the bedroom. She pulled out red nail polish and applied it to my toenails. As she moved to my fingernails, she giggled. "We should be able to get most of this off tomorrow morning before your meetings."

"I hope so," I said. "I don't think my business associates are expecting to meet with a woman."

I sat naked letting the nail polish dry as Sam pulled out a pair of her boxer shorts and pulled them on. She followed with a men's tank top, jeans, and a sweater. I guessed right about what was next.

Sam went to my dresser, pulled out a pair of my white panties and a bra and handed them to me. When I had put them on, she handed my fake breasts to me. I started to protest, but Sam said, "Nobody will be able to see them under your sweater."

She was right. With my jeans and a loose-fitting sweater on, my size D breasts were almost undetectable. There was no need to stop before leaving town and I was confident that my feminine attire and red fingernails would not be exposed. As Sam finished packing for both of us, she made sure that I saw her putting the strap-on dildo in one of the bags.

"What do you want to bet that my sexy little wench gets fucked tonight," she said.

I knew better than to bet against that happening. Sam smiled and kissed me on the cheek as she sent me to the car with our bags.

We were on our way after a quick lunch. There wasn't anybody around and my femininity easily escaped detection. We had been driving a couple hours when Sam said that she needed to stop at a rest area. There were several trucks and a few cars parked at the rest area when we pulled in. I shut off the car and Sam took the keys. Then she pulled a bag from the back seat and handed it to me. "See you in a few minutes," she said as she jumped out of the car and headed for the restroom.

I was sure that I knew what was in the bag as I nervously carried it toward the restroom. There were only a couple men present when I walked in. The handicapped stall was free so I went in and latched the door behind me. That gave me good privacy and room to make the change of clothes that I knew Sam expected of me.

When I opened the bag, I found a white, light-weight sweater. As I replaced the sweater that I was wearing with the one from the bag, I realized that my bra showed clearly through the thin material and my fake breasts bulged out against the tight fit. Next, I pulled a dress from the bag. It was a red corduroy jumper. I removed my jeans and pulled the dress over my head. It had a scoop neckline that ran under my bulging bra and the hem was about mid thigh. I felt a slight tightening in the front of my panties as I ran my hands down over the front of my sweater and dress to smooth the wrinkles.

A pair of sandals and my wig completed the outfit. I sat on the toilet to put them on and stuffed my other clothes into the bag. I had heard the flush of urinals a couple times while I was changing clothes. I listened and didn't hear anybody else in the restroom, so I slowly lifted my head above the partition. One man was standing at the urinals looking down. He didn't see me and I ducked back down. It seemed to take forever for him to finish and leave. In the meantime, I heard somebody else come in and take one of the stalls. It also sounded like somebody else had come in and was peeing into one of the urinals.

"Shit, I'll never get out of here if I wait until it's empty," I thought.

Finally, I summoned up the courage to leave the safety of the stall. As I hastily walked toward the door, another man walked into the restroom. I tried to avoid looking at him, but could tell that he was checking me out. I kept going and didn't look back. Outside, there were several people walking around out of their vehicles, but they were all some distance away. When I got to the car, I remembered that I had locked the doors. Sam had not yet returned with the keys. As I stood nervously by the car, a truck that was leaving the rest stop slowed slightly. I looked up and saw that the driver was staring at me. I gave him a nervous glance and turned away. He resumed his exit toward the freeway.

As I looked back toward the restrooms for Sam, I realized that she had been seated on a table a short distance away watching. She quickly got up and walked over to me. She clearly was enjoying my predicament. "I think you could have gotten a ride with that trucker," she giggled.

Sam opened the passenger door and let me into the car. Once she had settled in behind the wheel, she turned to me and gave me a quick kiss. After adjusting my wig, Sam pulled out a make-up kit, powdered my cheeks, and applied lipstick. "You are so hot. It is going to be difficult for me to wait until we get to the hotel," she said.

As we drove down the freeway, we noticed several truckers who we passed checking me out. I don't know if they mistook me for a woman. A couple of times when Sam realized that a truck driver was looking my way, she reached over and ran her hand up the inside of my thigh, pushing the hem of my dress almost to the crotch of my panties. My cock would immediately respond to her teasing touch. I was beginning to realize that Sam has an incredible knack of being able to push me just beyond my comfort level and, in so doing, take both of us to new sensual heights. As we continued toward the bay area and our hotel, it was becoming increasingly apparent that Sam would soon be hammering my ass with her dildo, and I wanted it so badly.

Robin was working the desk when we walked into the hotel lobby. "Sam, Dawn, it's great to see you," she shouted as she ran from behind to encounter.

She gave me a hug and a little peck on the cheek. "My, you are looking sexy this evening."

Then she turned to Sam and hugged her. "And, Sam, you are looking great also. The move out of the city must have really agreed with you."

Sam smiled and slipped her arm around my waist. "We've been looking forward to being back in town and seeing you."

I snuggled a little closer in Sam's protective arm and smiled, forgetting that some of the other people in the lobby might consider my attire to be a little odd.

Sam and I could barely wait to get to our room. We had only eaten a light lunch and we were hungry. But we were hornier. We no sooner closed the door to our room than we were in a deep embrace, our lips locked together, our tongues exploring the other's mouth.

"I want you inside me," I gasp.

Sam smiled. "My little cock hungry wench. Get ready."

While Sam rummaged through her suitcase for the dildo, I sat down on the bed and quickly pulled my panties off. I watched impatiently as Sam seemed to fumble with the straps for the dildo, my hardened cock forming a tent on the front of my dress betraying my sexuality.

Finally, Sam had the dildo secured and was standing in front of me. I grabbed it and opened my mouth to take the head between my lips. As my tongue flicked around the head of the dildo, I ground the base against Sam's sex. She moaned, "Suck my cock."

I looked up into Sam's eyes. She smiled in ecstasy. She grasp the back of my head and pulled me to her pushing the dildo further into my mouth. I continued to suck as Sam ground her hips with increasing urgency.

I pulled loose from the hold that Sam had on my head. "Fuck me, Sam."

As I scrambled to kneel on the floor, I gathered my dress around my waist. I leaned forward, my face on the bed as Sam positioned herself on her knees behind me. I briefly felt the head of the dildo poised against my asshole. Then with a sharp thrust of her hips, Sam drove it home. My arms were by my side and Sam grabbed my wrists pulling me back toward her. I eagerly responded arching my back to open myself to the probing dildo.

Sam began to pummel me with the dildo, thrusting her hips to drive it deep into my ass, then pulling back and thrusting again. "My sweet little wench. My cock hungry little wench. Oh, fuck. You sexy little thing."

I was about to explode. "My clit, please rub my clit," I begged.

I felt Sam's hand snake its way down past my hip to grab my cock. She held it tightly as she continued to fuck me. I felt the pressure of my own orgasm building. I tried to hold it. Sam's thrusting was becoming more urgent. Her thighs were slapping against mine.

I couldn't hold back any longer. "I'm cumming," I gasp as my spurting cum coated the insides of my legs.

Sam was moaning. Her excitement was continuing to grow. She had a tight grip on my cock with one hand. She was steadying herself by holding onto the back of my dress with the other. The undulation of her hips was becoming more and more urgent. She was grunting with each thrust of the dildo.

With one final thrust, she let out a deep sigh. As she slowly ground her hips against my ass, I felt her slowly lower her body down onto mine. She released her grip on my cock and let me suck my cum from her fingers. We relaxed there in mutual bliss still coupled together by the dildo.

When our heart rates returned to normal, Sam slowly withdrew from me. "Stay there," she said.

She dashed to the bathroom and returned with a wash cloth. As I continued to kneel with my ass in the air, Sam gently milked the last of the cum from my cock and wiped the sticky residue from my legs. "We don't want any stains on your dress," she said giggling.

We flopped down on the bed side-by-side. I turned my head to look at Sam. She was looking at me, a contented smile on her face. She reached up and caressed my cheek. As we lay there together, the room darkened as nighttime approached.

We realized that we had not eaten dinner. Sam suggested that we call out for a pizza. I retrieved my panties and went to the bathroom to repair my makeup while Sam placed our order.

Sam walked to the corner grocery store to get beer. When she returned, she said that Robin would be off duty soon and would be joining us. Sam opened a couple beers and arranged chairs around the table while I grabbed a towel to mop my cum from the carpet.

I had barely finished that task when Robin arrived. If the room still smelled of sex, she didn't give any indication that she noticed. We sat down to sip our beers and chit chat while we waited for the pizza delivery boy. Sam told Robin how happy she was having moved in with me. I blushed when Robin smiled at me and said that whatever I was doing, it must be great.

I didn't think about my attire when I jumped up to answer the knock on the door. I was halfway across the room when I realized that I was still in a dress. I turned back toward Sam. She smiled and nodded toward the door. I slowed my dash to the door, made sure that my shoulders were back, and fell into my most provocative, hip-swaying walk.

The pizza delivery boy's jaw dropped when I opened the door and led him over to the table where Sam and Robin sat. Sam paid for the pizza and I escorted the delivery boy to the door. When I returned to the table, Sam and Robin were laughing.

"What," I asked?

"We're jealous," Robin said. "He was checking you out more than us."

I blushed.

"We're going to have to find an ugly chick to hang out with," Sam teased.

Sam and Robin coached me on my feminine mannerisms as we dined on pizza and beer. They assured me that I was pretty enough to pass as a woman except on a very close examination. My confidence at going out in public grew with their encouragement and advice.

Before Robin left for home, we decided to double date with her and her boyfriend the following evening. They were planning on dinner at a local nightclub. Sam and I will join them.

We undressed for bed. We were both nude when Samantha realized that I was still wearing nail polish. She dashed for the bathroom to retrieve polish remover and tissues. We sat on the bed as she carefully removed the polish from my fingernails in preparation for my meetings the following day. As she studiously concentrated on her task, I let my eyes roam from her face, down to her beautiful breasts with their little button nipples, then down to the dark pubic patch covering her wonderful pussy lips. Samantha looked up once and caught me surveying her body. She blushed and giggled a little, then went back to work on my nails.

I felt slight twinges in my cock as we sat there, but, alas, I had already blown my load twice that day. I knew that I needed to reserve some for tomorrow.

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