0 comments/  36757 views/  3 favorites

Dawn's Diary Ch. 01

By: dawn43



My name is Donald. I am a single businessman in a small northern California town where I am well known. I am 30 years old and six feet tall. My hair is sandy blonde. I am fairly slight of build and thought of myself as the 90-pound weakling shown in bodybuilding ads when I was younger. However, I am an avid runner and bicyclist and keep myself in good shape.

By day, I dress in a suit and tie, but often when I get home in the evening I change into sexy lingerie. I first slip on thong panties and a bra with fake breasts that fill size B cups. Then I pull on a short slip or a mini-skirt and sheer blouse, depending on my mood. The smooth, silky feeling of women's lingerie against my skin is a wonderful feeling.

Except for my arms that others can see when I am at work, I keep my body cleanly shaven to enhance my femininity and the feel of the lingerie against my skin. Many bicyclists shave their legs to improve their aerodynamics and for faster healing of road rash. My bicycling serves as a perfect "excuse" for my shaved legs.

I frequently travel to the San Francisco area on business. When I am on those trips, I go back to my hotel room at the end of the day and slip on lingerie under my business clothes before going out for dinner and a few drinks. The lingerie and the bulges of my fake breasts are barely visible under my clothing and thrill of wondering if they can be detected by the strangers who I encounter is a real turn-on.

A few days ago, after a long day's work in the bay area, I had slipped on sexy pink lingerie consisting of a lace thong, demi bra, and pretty lace camisole under my suit before going out to dinner. As I ate dinner, I kept an eye on the young attractive waitress who served me to see if she seemed to notice the slight bulge of my breasts against the inside of my jacket or the faint coloring of my lingerie through my shirt. She gave no indication that she saw what I was wearing which suggested to me that it was not noticeable as I had feared, or perhaps hoped.

After dinner, I returned to the hotel and decided to have a couple of drinks in the bar. I went in, sat down in an out of the way corner and ordered a drink. The waitress was a tall slender young woman with short brown hair. She wore a short skirt that displayed her long legs to great advantage. From my seated position, I couldn't tell exactly how tall she was, but I guessed that she was taller than me. The name tag that she wore indicated that her name was Samantha.

It being a weekday, the place was quiet with very few patrons. A football game was on the television and, absent other distractions, I soon became interested in the game. I largely forgot the lingerie that I was wearing and, as it was fairly warm in the bar, soon slipped my jacket off and loosened my tie.

As the evening progressed, I downed a few more drinks. I thought I saw Samantha's eyes wander down to my chest a couple of times when she took my drink orders, but she didn't say anything to indicate that she noticed the slight bulge of my fake breasts against my shirt. At one point, Samantha put her hand on my shoulder as she was taking my order and it almost felt like she ran a finger over the strap of my bra, but again she didn't say anything to confirm that she had discovered my lingerie. After an hour or so, Samantha asked me to cash out my tab because her shift was ending. I gave her a generous tip and she was on her way.

I stuck around to watch the rest of the game and to finish my drink. I was pleasantly surprised when Samantha returned to the bar after about a half hour and asked if she could join me. She had changed into jeans and a loosely fitting sweater that largely hide her femininity. I quickly consented and we ordered another couple of drinks from the bartender.

"My friends call me Sam," she said.

I told her that my name was Dawn.

Our conversation covered a variety of subjects. Sam said that she was single and had moved to the bay area only recently. I learned that she enjoyed hiking and camping and had played basketball under a scholarship at a small Midwestern university. As we talked, the now largely ignored football game on the television ended and the bartender announced that the bar would soon close.

Sam suggested that we continue the conversation in my room. The fact that I was wearing lingerie suddenly flashed through my mind and I wondered where this encounter was going. Would we end up in bed? Would I be able to slip into the bathroom and take off the lingerie without her knowing? Would she discover that I was wearing lingerie and, if so, what would her reaction be? In any event, the risk and excitement of the possibilities were inescapable. I quickly agreed, we finished our drinks, I slipped my jacket on, Sam picked up her rather large purse and we headed for my room.

I had a few bottles of beer in the small refrigerator in the room and opened one for each of us. We sat down at the small table in my room and continued our conversation. In the back of my mind were the continued questions about where this was leading, but before I could decide what to do, Sam indicated that she needed to use the bathroom. She took her purse and left me sitting at the table still wondering.

It wasn't long before I heard the bathroom door open and looked up to see Sam approaching me. She had removed her pants and sweater and was wearing boxer shorts and a tank top undershirt. She carried a tube of KY jelly in one hand. Protruding from the boxers was an enormous dildo.

I immediately realized that not only had Sam detected my lingerie under my clothes, but that I was going to get laid that night in a way that I had not imagined. Sam told me that she had noticed the bulge of my breasts and the straps of the pink camisole while waiting on me and that, when her shift had ended, she had stopped by the adult store down the street and purchased the dildo, then had gone home to quickly change clothes.

Sam called me a little bitch for having flaunted my tits in the bar and told me that my behavior clearly demonstrated that I yearned for a good fucking. I was still seated as she continued to walk toward me until the dildo was directly in front of my face. "Suck my cock," she said as she grabbed the back of my head and pulled it toward her.

The dildo filled my mouth and the head jabbed at the back of my throat. I almost gagged, but she kept pulling my head toward her and her hips started to gyrate as she fucked my face. Despite the discomfort of having a dildo jammed down my throat, I eagerly licked and sucked it until she pulled back.

"Undress," she said.

She watched closely as I removed my tie, then my shirt displaying the sexy pink camisole and releasing my fake tits from the confines of my shirt. I then removed my shoes and socks and dropped my trousers revealing the thong and my shaven legs. My dick had grown hard and was budging against the thin material of the thong. Sam asked if I shave all over and grabbed the front of my thong pulling it out so that she could see the bald base of my cock. "My God, you are sexy," she said.

Sam handed the tube of KY jelly to me and told me to put some on the dildo. I was pretty sure I knew where the dildo was going next and made sure that it was covered with a generous amount of lubricant. Sam then told me to get down on my hands and knees on the floor and she moved around behind me. I felt her slowly pull the narrow band of nylon from between my buttocks. Then I felt the head of the dildo pressing against my asshole. Although I frequently use a small vibrator in my ass when masturbating at home, the dildo was much larger. As Sam continued to press up against me, the dildo slid into my ass and the pain caused me to let out a soft moan. Sam asked me if I had been fucked this way before and I shook my head, "No."

Although I was experiencing an intense pain from having such a large intrusion into my rectum, my own cock was growing even harder. I moaned in a combination of pain and pleasure and begged, "Fuck me, Sam. Fuck me hard with your big dick."

Sam pulled back until only the head of the dildo remained in me, then thrust it back in. Her hips were soon gyrating back and forth with increased frequency, with each thrust forward driving the dildo into my ass further and harder. Her breathing became more and more heavy as the blunt end of the dildo ground against her clitoris until with one final hard thrust she came.

Sam slowly withdrew the dildo from my ass and grabbed my head to pull me around. By her motions, I was able to tell that I was to stay on my hands and knees. As I turned around toward her, she was still on her knees and the dildo was again sticking out toward my face. She continued to pull me toward. "Lick my cock you horny little bitch," she said and pulled my face up against the dildo that had just been buried in my ass. I felt both degraded and strangely excited. I began to lick and soon took the head of the dildo back into my mouth as Sam slowly fucked my face.

Finally, Sam withdrew the dildo from my mouth and told me to lie on my back on the bed. She lifted my legs to her shoulders. As she pulled my thong aside, I took the dildo in my hand and guided the bulbous head to my asshole. It slid in easier this time as Sam pressed her hips toward me. As she started to slowly pump her hips driving the dildo deeper and deeper into me, Sam asked me if I would like her to rub my clit and I nodded, "Yes."

She reached down and started rubbing the front of the thong that by now was barely holding my erection. With the same rhythmic movement of her hips driving the dildo into my ass and then pulling back, she ran her hand back and forth over the bulge in my thong. After the long buildup of energy and anticipation, it did not take long before I experienced one of the most intense orgasms ever and cum exploded from my throbbing cock.

Sam continued to slowly pump the dildo back and forth in my ass and stroke my cock until I finally relaxed in post coital bliss. As she reached up to tenderly caress my cheek, I instinctively turned my head to take her fingers in my mouth. They had the salty taste of cum. She smiled as I eagerly sucked and licked the last vestiges of my own jism from her fingers. 

Sam slowly withdrew the dildo and, as I remained stretched out on the bed thinking about what had just happened, she silently went into the bathroom. When she came back out, she told me that I should call her the next time I was going to be in town. With that, she wrote a phone number on the note pad by the bed and let herself out the door. I can hardly wait for my next business trip.

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.



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.




Dawn's Diary Ch. 03



Sam told me how fascinated and excited she had been when she saw me in the bar that first night and realized that I was wearing lingerie. She confessed that she frequently wore men's underwear because something about doing so excited her. She said that she had barely been able to contain herself the first night that we met as she had dashed home after work to change. Sam giggled a little as she admitted that she had allowed her hand to creep down to the crotch of her jeans that night as she had driven hastily back to the hotel. We both laughed as we realized how perfectly matched we were.

Sam wrapped her arms around me and pulled me toward her. Our mouths met again, each of our tongue's exploring the other's mouth. Finally, Sam pulled away, looked into my eyes, and said, "I love fucking you, but I also love being fucked. I hope you will be my girlfriend again, and again, but right now I want your cock in me."

I quickly pulled her to me and kissed her deeply. I couldn't believe it. I realized that Sam was the woman of my dreams. A beautiful woman who understood and shared my crossdressing urges and who could take me to incredible heights of orgasmic satisfaction with her dildo. And, a woman who also wanted to experience my cock buried in her pussy.

Samantha crawled out of my embrace, pulled my baby dolls over my head, and unfastened my bra. My fake breasts tumbled out onto the bed and, with a laugh, Samantha gathered up the accoutrements of my femininity and discarded them onto the floor. Then she climbed on top of me and gave me a deep, long kiss. Breaking the kiss, I was able to get my mouth down to her breasts. They were small, but from my standpoint more than adequate, and I softly licked and sucked her hardening nipples. Samantha's legs were splayed on either side of mine and she ground her pussy against me. My cock immediately sprang back to attention and Sam quickly guided it home. Her pussy was already moist and easily engulfed me. The feel of her pussy around my cock was almost as nice as having her dildo jammed up my ass.

It did not take long for the gentle rocking of our coupled bodies to give way to the hurried thrusting of our hips together as each of us rocketed toward orgasm. I felt the cum welling up in my balls until I could hold it no longer. Samantha continued to pound her pussy against me until I felt her body tighten and she let out a soft moan. As the spasmodic throbbing in my cock and Samantha's contractions around it began subside, I felt her body slowly relax down onto mine, my cock still embedded in her warm pussy.

As we lay together in bed, Samantha told me that she didn't think that she was really cut out for life in a big city. She said that she had grown up in a small town and now realized that she liked a lower pace away from the city. I pondered what she had told me and mustered up the courage to say, "Sam, you know, if you moved in with me, you could fuck me more than once a month."

Samantha quickly responded with a smile, "And you could fuck me more than once a month."



Dawn's Diary Ch. 04



We've exchanged email regularly, but I haven't seen Sam for more than a month. She called last night and said that she had worked her last shift at the bar. She is moving out of her apartment this morning and will be on her way. She assured me that her dildo was safely packed in her purse so that it would be readily available when she gets here. I've been saving my cum in a glass in the refrigerator. It's almost half full.

I took special care when shaving this morning and put on the red lingerie that Sam gave me that last time I saw her. Then I pulled on a pair of jeans and a light work shirt so that I can help Sam unpack her car. God, I hope none of the neighbors drop by when I am outside. The buttons on the front of my shirt are almost ready to burst under the pressure of my size D breasts and, despite the confinement of the thong panties, my hard cock is straining against the front of my jeans.

The doorbell rang at a little after 2:00 p.m. I was in the bedroom making room in the closet for Sam's clothes and hadn't heard a car in the driveway. The doorbell startled me and my first thought that it was a neighbor who had walked over for some reason. Here I was with the front of my shirt bulging because of my fake breasts and the front of my jeans bulging because of my perpetual hard on. I quietly went to the front door and peered through the peephole. It was Sam.

I flung open the door and Sam lept into my arms, her purse dropping to the ground. We embraced, holding each other tightly and exchanged deep kisses. Finally, Sam broke free, picked up her purse, and said, "Let's go inside."

I had barely closed the door when Sam wrapped her arms around my waist and backed me up against the wall. She tugged my shirt free of my pants and slid her hand down the small of my back to the waistband of my panties. I felt the pull of the narrow band of nylon between my ass cheeks as she gave my panties a small tug. Breaking our kiss, Sam smiled, "Nice."

My arms were wrapped tightly around Sam's shoulders and her mouth again met mine. As our tongues continued to flicker together, Sam's hands continued to explore my body. By now, she had freed my shirt from my jeans and I felt one hand slide up across my belly up to the outside of my bra. As Sam massaged my breast, her other hand dropped to my crotch and she started rubbing the growing bulge on the front of my jeans.

I let out a small moan as she released her grasp on my breast and unbuttoned my shirt revealing the red camisole. Sam's mouth and flickering tongue moved down to my neck. Her left hand returned to my breast while her right hand continued to caress the growing bulge in my pants. There I was standing in the hallway of my house, backed up against the wall. Sam had only been there a few minutes. We were still clothed. Her grip became more firm and the rubbing became more urgent as she continued to manhandle me. I could feel the pressure in my cock rapidly building toward eruption. "I'm going to cum," I gasped.

Sam continued to massage my crotch as the involuntary heaving of my hips against her hand became more urgent. Finally, I could hold back no longer and jets of sperm spewed from my throbbing cock soaking my panties and jeans. As the throbbing began to subside, the rubbing of Sam's hands became soft caresses. Sam whispered, "I think my little wench's pussy is wet."

I was embarrassed. The wet spot on the front of my jeans was growing. But Sam just smiled. As I regained my composure, Sam said, "Let's get my things out of the car."

"Great," I thought. Here I am wearing red lingerie, the front of my pants soaked with cum, and Sam wants me to go outside.

I re-buttoned my shirt. I hoped that, by not tucking it in, the wet spot on my jeans would be hidden if somebody saw us. Sam giggled as she reached up, unbuttoned the top button of my shirt, and headed out the door. I, of course, followed her.

We hurried to carry Sam's things in from her car. It only took a few trips. Sam said that, having graduated from college earlier in the year, she really had not had time to accumulate very much stuff. She said that she had left a few things in Robin's garage and hoped to retrieve them the next time we went to the bay area.

A neighbor from across the street spotted us and waved. For a moment, I thought he was going to come over, but he must have sensed that Sam and I didn't want to be interrupted. I was thankful of that. I don't think he was able to see my red lingerie showing above my partially unbuttoned shirt or the cum-soaked front of my jeans.

Having unloaded Sam's things from her car and given her a short tour of the house, I realized that I was getting hungry. I suggested that we clean up and go down to a local bar for a bite to eat. Sam agreed and started to remove her clothes. She kicked off her shoes and slipped out of her jeans and sweater throwing them onto the bed. Next off were the boxer shorts and tank top. Before I could remove my shirt, she was standing nude in front of me.

It was at that moment that I realized how stunningly beautiful Samantha is. Her high cheekbones accent a face not encumbered by makeup. Her pert breasts easily pass the pencil test. She is trim and athletic with muscles rippling in her legs, arms, shoulders and belly—not bodybuilder style muscles, but sexy and smooth.

Samantha giggled when she saw me staring. She gave me a quick kiss before unzipping my pants and proceeding to help me divest myself of the rest of my clothes. My cock quickly sprung back to attention as we headed for the shower. I tried to wrap my arms around her as we stood together under the warm water, but Samantha resisted, "After dinner, my little wench."

After a quick shower, we hurried to get dressed. I put on a garter belt and stockings. As I was preparing to put on a pair of thong panties, Sam said, "Stop. Bend over. I want to give you a little something so you don't forget what you are in for tonight."

There is no way I was going to forget, but quickly spread my legs and bent over, resting my hands on my knees. Sam pulled a butt plug from her purse and deftly shoved it up my ass. By now, I was conditioned to being violated in such a manner and easily accepted the penetration. As I pulled the panties on and tucked my cock into the thin fabric, I could feel the strap of my thong panties pushed against the butt plug.

Sam pulled the harness for the dildo out of her purse and put it on. She said that the rubbing of the straps against her pussy would help her remember what I was in for later. Then, she put on a pair of boxer shorts and a tank top undershirt. We both put on jeans and sweaters over our gender bending underwear and headed out the door.

We ran into a few of my friends at the bar. I introduced Samantha to them and could tell that they were impressed. As we sat together in the booth eating dinner and enjoying a few drinks, the butt plug served as a reminder of my impending fucking. A couple times, Sam leaned over and kissed me on the cheek. As she did so, she rested her hand on my thigh and discreetly hooked her finger on the strap of the garter belt hidden under my jeans. She giggled a little as she pulled her hand away and the strap snapped against my thigh. My cock responded to her flirting and strained against my panties with increasing pressure.

We finished our dinners and jumped in the car for the quick trip back to the house. As I drove, Sam rested her hand on my leg, her fingers playing with the garter strap. My cock continued to swell. By the time we got to the house, the fabric of my panties barely contained my erection and the pressure of my hard cock bulged out against the front of my jeans.

The door had barely closed behind us before our jeans and sweaters were laying on the floor. I told Sam to grab a couple of beers out of the refrigerator as I headed for the bedroom to top off my feminine attire. The bra that I selected was a size D to accommodate the breast enhancers that I had worn the last time Sam and I were together. My camisole was made of spandex and had lace trim. It stretched tightly across my breasts and hugged my belly. They complimented the panties and garter belt that I had worn to dinner.

When I emerged from the bedroom, Sam was smiling. She was holding two bottles of beer in one hand and the half glass of my cum in the other. She gave me one of the beers and said, "Be right back," as she disappeared into the bedroom.

I dropped to my knees in the middle of the living room when she emerged, her now familiar dildo poking out of her boxers. She stood in front of my eager mouth, teasing me by slapping the dildo against my cheeks, letting me get the head between my lips only to pull it away, touching it to the tip of my nose, letting me touch it with my out-stretched tongue, all the time giggling. "What an eager little cocksucking wench."

Finally, Sam let me take the dildo into my mouth. I reached up and grabbed her hips pulling her toward me until the head was almost to the back of my throat. She drew back a little when I gagged, then grabbed the back of my head and thrust her hips. The gag reflex passed and I was soon able to take more and more of the dildo in my mouth as she drove her hips forward while holding my head. I responded. My hands had slipped down to her ass and I was matching her rhythmic thrusting by pulling her deeper into me.

Sam started to gasp and moan softly. The tempo of her thrusting increased as she fucked my face with more and more urgency. With one final thrust, she drove the dildo into my mouth and pressed my head against her. I felt her slowly rotate her hips massaging the base of the dildo against her pussy and I tasted the salty cum that I had been saving filling my mouth. I couldn't swallow fast enough and some of the cum dribbled out of my mouth and down onto my camisole.

Sam dropped to her knees and wrapped her arms around me. Our mouths met and her tongue flickered out to meet mine. She pulled back. Some of my cum was smeared on her chin. I wiped it off with my fingers. She took my hand and pulled it to her mouth, licking my fingers clean. I felt her hand slid down my back and her fingers probed between the cheeks of my ass. "I think it's time to remove this," she said as she lightly tapped the base of the butt plug.

I hurried to the bathroom where I slipped out of my panties and removed the butt plug. The pressure in my ass was relieved, but my cock stiffened with the thoughts of Sam's dildo and the building anticipation that she would soon be fucking my with that wonderful rubber cock. I pulled the little negligee that Sam had given to me over my head and hurried to rejoin her.

Sam had switched off most of the lights in the house while I had been changing. Only the bedside lamp illuminated the bedroom. Sam was sitting on the bed, clad only in her boxers, the dildo jutting from the fly. She smiled as I approached, my hard cock poking from under the hem of my negligee. "Lie down on your stomach," she said.

I climbed onto the bed beside her. As she leaned over me, I shuttered in anticipation at the press of her dildo against my leg. However, she didn't immediately mount me like I had expected. Instead, I felt the flick of her tongue, first in my ear, then on the back of my neck. Her hands traced the straps of my bra through the thin fabric of my negligee, then slide down to the hem and back up to cup my breasts. She slowly slid down, letting her breasts slide over my back. She lightly bit my butt check and then started to run her tongue down the crack of my ass. I moaned and instinctively raised my hips slightly. She continued down pushing my legs apart until her tongue could reach my quivering balls.

Sam licked and sucked my balls as I squirmed and moaned. My erect cock was underneath me and the grinding of my hips was rapidly taking me toward ecstasy. I felt Sam's hands spreading my buttocks and her warm tongue pressed against my asshole, gaining slight entrance with its pressure. I felt the pressure of an orgasm building and knew that I needed her inside me. "Fuck me, Sam," I pleaded.

Sam quickly moved to take me. I lifted my ass to meet her as I felt the dildo sliding up my leg toward its target. Sam positioned the head of the dildo against my eagerly waiting asshole and drove her hips toward mine. I pushed back against her impaling myself. The massive intrusion into my rectum produced a mix of pain and pleasure. I gasp, "Oh, God. I want all of you in me."

The urgent thrusting of our hips was pounding my own cock into the bed. Sam whispered, "My little wench likes my cock, doesn't she," as she nibbled my ear.

I could only moan as I continued to meet her thrusts driving the dildo further and further into my ass. Sam sensed my impending orgasm and slid her hand down to grab my cock. I couldn't hold back any longer and cum exploded from my throbbing erection. Sam eased her pounding of my ass as the contractions in my balls slowly subsided.

We lay there on the bed spent, Sam resting on top of me, the dildo still firmly lodged in my ass. Sam released her grip on my cock and we took turns licking my cum from her fingers. She softly kissed my cheek. I tried to turn to meet her mouth with my own, but couldn't reach. She smiled and nestled her face on my shoulder, her fingers idly tracing my bra strap.

I was in heaven. Sam fulfilled all my dreams and here she was in my bed. I think I dozed a little but was awake again as Sam gently raised herself off of me pulling the dildo from my battered ass. When she emerged from the bathroom, she was nude. I quickly removed my negligee and bra as she turned out the light and crawled into bed beside me. We slept soundly that night, Sam curled up in my arms, both us completely spent, and dreaming of adventures yet to come.



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.