A closet crossdresser meets his match

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.
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