My girlfriend Tonya was out of town for the weekend. She was meeting some college friends and going shopping and carousing in the city. A typical girls' weekend. I kissed her good bye at about 4:30 pm on Friday. We had become pretty close in the year that we had been dating. She was a cute blonde with the lithe athletic build I loved so much. We also got along so well. We were like drinking pals that enjoyed sex together. I knew that I was lucky to have her.

Yet as close as we had become I couldn't bring myself to tell her my biggest secret. Whenever my girlfriend was out of town for any length of time I engaged in my favorite pastime. I was addicted to dressing as a woman. I would even be so bold as to take drives around town dressed up.

I know I have one hell of a fucked up pastime. Yet like so many unbreakable habits I had started young. My senior year in high school I had found some porno magazines in a neighbor's garbage. I hid them in an old tree house I had built in the yard. The magazines all had pictures of men dressed as women. One in particular had affected me, it had a pictorial that started out with an absolutely stunning woman posing in a formal evening gown. Slowly, page after page she stripped down until she was standing there in only her pantyhose and high heels. I turned the page and saw the next picture. She was standing there holding an enormous erection that she had slipped out from a slit in her nylons. To me she was still too beautiful to be anything but a woman, even with a cock. Until I saw the next picture. She was actually a he. The man had been wearing a wig and he was standing there holding it in his hand. He was smiling into the camera as if to say he knew he had fooled everyone, especially me. There was even a picture of him in the front pages of the magazine dressed as a man. An average looking man! I was blown away. How could an otherwise masculine man become that beautiful?

I began to experiment with myself. It started with my mother's closet and progressed onto the women I baby sat for. When I was alone I got into the stockings and garters and anything else that would make me look like a woman. Now at 31 I had developed the expertise and moxie to pass as a full blown woman. I had gotten so good at make up that when I dressed, the only outward sign of manhood was my voice.

By 6:30pm a mere two hours after Tonya had left town, I had gulped down a quick meal and had applied my make up and fixed my hair. My hair had some length to it for a man but the brown locks made a nice short hairstyle for a woman and I kept it androgynous enough. I parted it down one side of my head and let it flow down the other. A little goop for some hold and a greased look and I had to be honest, quite a few woman would be jealous.

It was warm for an early spring night, about 85 degrees, so I went with a bohemian look. A lot of crossdressers liked to dress slutty. I dressed more or less to fit in. Although I had never stopped anywhere dressed as a woman, dressing like a normal woman out for a drive gave me confidence. I slid some really sweet stockings on that I had discovered in a mail order catalogue. They had arrived a week or so ago and I was busting at the seams to try them on. They were a a very sheer bright royal blue color. I hooked them to my garter belt and slipped on a pair of black pumps. The loose fitting sundress I dropped over my head went down to about mid thigh. I looked in the bedroom's full length mirror. Everything matched and I looked downright sexy. I had been dieting for about three weeks in preparation for this weekend so I was down to about 140lbs. Like Tonya I have somewhat of an athletic build myself and I am 5'-8" so I was a little light but it was worth the pain and torture. It had been 6 months since I had been able to do this and despite being older each time I always looked better. My cheekbones stood out with a light coat of blush and mascara brought out my blue eyes and had them sparkling.

As I stood there admiring myself the usual reluctance hit me. Why was I doing this? I mean I wasn't gay. Hell my girlfriend was beautiful. In fact I always tried to mimic her make up and her style when I dressed. I always told myself it was the thrill. Or did I just want to pull off what that man in the magazine had done? Make myself so beautiful that I could fool anyone with my looks. I knew at this point ego was involved. I knew I looked good as a woman, as good as that man did with I am sure some professional make up help. I had begun to understand why women were so desperate to look pretty. Vanity was definitely a sin.

I hustled into the garage and hopped into the car. The street was clear and it was dark so I was able to quickly escape from my neighborhood and get across town. I was rock hard as the first car pulled up to mine at a light. The young man couldn't take his eyes off me as I sat there pretending not to notice, gently rubbing my silky smooth panties against my erection. I took a turn down a side street into a very nice neighborhood to catch my breath. Obviously most people would consider this just plain weird but to me it was an incredible turn on. Then it happened. The light for the heat sensor was blinking. I took evasive action turning my Jetta around and hoping against hope I could make it back home. It wasn't going to happen. I lived almost 10 miles away. I pulled over and turned off the engine thinking if I let it cool down a bit I could start back home. It was at that point that the steam began escaping from under the hood. I got out of the car and popped the hood. It was clear that the radiator needed more water if I was going to make it home. I leaned over the engine and checked it out.

"Had your air conditioner on, huh?" Came from the walkway I had landed in front of.

I jumped out from under the hood. After a couple of years of wondering whether I could pull it off as a woman, I was now going to get my chance. Only I knew it was hopeless. I had a man's voice and a fairly low cut dress that showed off quite the Adam's apple. I had been busted and it was going to be pretty embarrassing. The well built black man had come out of his house. He was wearing a tee shirt and what looked like a pair of bicycle shorts.

He had long dreadlocks, which hung down his back. He was standing there in his bare feet checking out my legs. I knew as soon as I spoke no amount of darkness would protect me and he would know I was a man.

"You need some water?" He asked in a funny accent I couldn't quite place.

"Ugh yea, well I was at this costume party and ..." I thought I had come up with a half decent excuse for my outfit but he didn't bite.

"Well you're a long way from Halloween." He smiled after showing some intiial shock at hearing my voice. "Come on in. I even have some of that anti-freeze that plugs holes." He started back into his house having satisfied his curiouslty as to what had been going on in front of his house. If I wanted his help I was going to have to follow him inside. I had never seen him before and probably never would again. Besides he seemed willing to help me despite my being a transvestite so I decided to get this embarrassing situation over with as quickly as possible.

"Come on in." He repeated as he opened the front door to his house for me. I walked into the living room and the black man held out his hand. The first thing I realized was that I had never interacted with anyone dressed as a woman. I had no idea how to act or what to say. I decided to not try and be feminine with my voice. It just wasn't going to work and the cat was already out of the bag anyway. We shook hands.

My name is Jacques." By his name I finally recognized his accent as French.

"Hi I'm Dennis." I replied.

Don't you girls have a woman's name when you go out dressed up?" Jacques asked curiously.

"Well I am not really one..." I started to think of yet another explanation and then gave up.

"You look familiar." The black man stated as he looked me over. Now I really wanted to run away. This guy was going to pick me out of his past and then everyone in town was going to find out that I liked to go out dressed as a woman. I was thinkng about Tonya's reaction, my friends and quite possibly my family. I was devastated. He must have picked up my panicked reaction. "No, no I don't know you like that. I mean I think you look like someone famous or at least that I have seen somewhere. Don't worry by the way, your secret is safe with me." He finished with a comforting smile that made me feel a whole lot better. "I must think about this woman. Please do have a seat." He turned and went off to the kitchen.

I sat down on the couch and looked around the room. It seemed to be a large TV room with a more formal living room running off the side. I could tell by the size of the house and the way it was decorated that this man was successful. We looked to be about the same age but he could afford some rather expensive furnishings that I hadn't even thought of buying for my home. There were some impressive paintings on the walls and the room was framed with a dark expensive wood trim. I guessed the couch I was sitting on was custom made. It was very large and comfortable and made of a dark green chenille fabric.

"Well I remember who you look like." The black man said as he entered the room carrying two beers. "She was in a Bond movie with the one that only lasted a couple of movies. Forgive me but I am a fan of Sean Connery not the others. Although Roger Moore could make you laugh."

"I know who you mean. Thanks. I guess" I didn't want him to know that I was actually flattered. I had always thought that I dressed as a woman because I looked good doing it. Now I knew. The rush was a part of it too but there was my ego again. I knew I was better looking than the transvestites whose websites I checked out for ideas and inspiration. Jacques' compliment went a long way towards proving it. "Anyway thanks for the beer but I shouldn't."

"Well we are going to have to wait before we fix your radiator. It has to cool down." He was right. We were going to have to sit for a little while longer. I took the beer and I noticed him staring down at me and he shook his head. "You know you really are a dead ringer. You have the same hair and everything. I can't remember her charactor's name but maybe you should call yourself Carey, her real name."

He sat down next to me on the couch. While I would have been content to get this over with as quickly as possible, Jacques was bubbling with curiosity. "Who does your make up if you don't mind my asking?" Where do you shop? How long have you been dressing as a woman and what got you started?" The questions came at me a mile a minute. I could tell that Jacques was simply curious but I still had my legs crossed with my dress down as far as it would go. I could see him trying to sneak an eyeful of my legs and unfortunately for me the dress was loose but short.

"You do this often, play dress up?" Jacques asked his French accent shaping the words.

"Not really. My girlfriend doesn't know so I have to wait till she isn't around." I replied.

Jacques looked at me like I had two heads. "You mean you are not gay or at least bisexual?"

"Oh no!" I shot back suddenly nervous again. "You know most crossdressers and transvestites are heterosexual."

"I have to be honest. You wouldn't think someone who looked as good as you in a dress would want a girlfriend let alone have one. I mean. You must take so much effort and time to look this good." Jacques was truly astonished and his accent was getting heavier. "What is your girlfriend's name?"

"Tonya. She is a great girl." I replied as I pulled on my second beer and ignored what I had considered a derogatory comment.

We talked a bit longer and got into a college basketball game that was on the tube. Just a couple of guys hanging out except one was wearing a dress. I was into my fifth beer and getting pretty looped. I went to the bathroom and when I got out Jacques was standing there.

"I will be out in a minute and then we can get you on your way." He was smiling and looking at my legs again. I knew I had long muscular legs. In fact my inseam was a good 3" longer than the average guy of my height. Maybe when you put them in high heels and stockings even heterosexual men had to stare. Although the stares still unnerved me it still felt good to know he was admiring me. I went back to the TV room and sat back down on the couch. Jacques returned with a gallon jug of water and some anti-freeze.

"Well here we are. Are you ready to hear my deal?" He asked as he stood in the archway leading to the foyer.

"What deal?" I asked.

Jacques chuckled as he sat down next to me and pulled a squirt bottle out of the waistband of his lycra shorts. He put it on the coffee table which was now littered with beer cans. "Well you want some water, some anti-freeze. I want a full body rub."

"What! Aw fuck! Jacques I told you I'm not into guys. I can't do it." I barked. If I wan't sure before, I knew now that his stares were more than just curiosity.

"Well you are going to have to walk home in those pretty high heel pumps. It seems such a shame to ruin them." Jacques was gently caressing my crossed knee with his hand.

"You've got to be kidding me?" I pouted. I felt helpless. "Here I am dressed as a woman but as it turns out you're the faggot!"

"Hey I just got through lifting. I'm sore." He replied ignoring my dig at his sexuality. He took off his shirt exposing a thin but amazingly well developed upper body. The skin looked smooth and very dark. I stared as he twisted onto his belly and spread his legs out behind me on the couch.

"Just use some of that oil in the bottle." he said confidently as he pointed to the squirt bottle he had just brought in.

What could I do? I wasn't going to just grab the water and run. Four inch high heels tend to slow you down. I squirted some oil onto his back which was really just a series of muscular bumps and grooves. Then I pressed my fingers into the softness of his ebony skin. Jacques let out a low groan as I began to rub. I put the dreadlocks to one side of his head and rubbed his shoulders.

"That's it my dear but you need more leverage. I really want to feel you. Straddle me with those lovely legs of yours so you can really lean into me." The black man suggested. I reluctantly got up and swung my leg over him and lowered myself onto his ass. My dress slid up my body as I leaned forward. My cock also rubbed against the hardness of his buttocks as I moved. The feeling was unsettling.

I put more oil on his back. Jacques was drenched in it now. I worked the muscles hard and soon had him moaning and groaning. I wanted to get this over with but Jacques simply told me to move lower and to peel his shorts off.

"I'm not putting my hands on your ass!" I exclaimed.

"I said full body rub remember?" he retorted.

"Oh shit" I muttered. I was really in it now. I hesitated but Jacques started whining about not having enough water so I peeled the tops of the stretchy shorts down over his ass. Jacques pushed his ass up in the air and helped with the front part of the shorts and then plunged back down onto the couch. He was naked now and I was still straddling him. I noticed that some of the oil had stained my stockings and I was worried about the dress.

"Hey this oil is getting on my dress." I complained.

"Well then why don't you take it off?" Jacques responded.

"No way." I almost hollared back at him.

"Hey Bond girl, I am just laying here facing the other way." Jacques replied quietly trying to calm me down.

I thought about it and then lifted the dress over my head. I resumed rubbing his lower back and dribbled some oil on his ass. I put my hands on what were basically two large balls of muscle. Jacques didn't have any hair on his body and I noticed how soft and smooth his skin felt. I quickly slid down to the backs of his thighs. They were just as muscular as his buttocks. As I worked the crease where his legs became his ass Jacques spread his legs and his scrotum spilled out in front of me. It was large and his balls hung loosely in it. I also noticed that the round hardness from which the scrotum hung was basically the butt of his dick. It was thick and impressive. I got away from it by moving down to his calves. It really didn't matter though. I couldn't take my eyes off of it.

"There all done." I said but Jacques rolled over and looked up at me.

"You know you are a natural at this sort of thing." He smiled.

"At what?" I nervously replied.

"At being a woman. You act like one and you most cetainly look like one. You know all those men you say dress like women but are heterosexual?" Jacques asked and I nodded down at him. "They just haven't tried it with a man yet. No one who looks this sexy is going to just drive around in a car and be satisfied. Somewhere deep inside you are longing to feel a man." He was right actually. I was getting more and more turned on being with Jacques and I was like any other stuck up girl. I just needed a good fucking. I had satisfied my heterosexual side by playing hard to get but a new side had come out tonight. Why had I ultimately agreed to progress at each juncture taking off my dress, massaging Jacques' ass and actually agreeing to give him a massage in the first place? This side of me that had been hidden ever since I had been dressing as a woman wanted to explore the feeling of being with another man and more desperately to feel like a woman sexually.

"Big isn't it?" I heard Jacques say through my trance.

I looked down and saw that he was gently stroking his enormous erection. The biggest Goddamn erection I had ever seen. It arched up like a veiny tree stump and curved down to the large flared head that dug into Jacque's belly just above his navel. I didn't know what to do. He was just lying there staring up at me. The black man knew he almost had me. I ran my fingers through my hair and looked back down at him.

"Go ahead and touch it." The black man urged like a pusher selling his drug.

"I can't." I replied. Although I knew already that I was going to do it. My hands were resting on his upper thighs, too close for comfort.

"Carey my dear, look at you. You are wearing a bra, panties, a garter belt and stockings and some seriously sexy shoes. You know what? You look better doing it than most women. Someone with a body and a face like yours doesn't dress this way to stay a virgin. You've been looking for this for a long time. Go ahead give in. There's no one here but the two of us. This is your chance to really be a woman." Jacques was pouring it on and he had his hands all over my legs caressing up and down my thighs. And he certainly knew what I was thinking. He reached down and took one of my hands and placed it on his manhood. The first thing I noticed as I touched the underside of the prong was it's hardness. It felt like a bone. I gently ran my fingers along the shaft.

"How long is it?" I asked.

"Just a bit over 10 inches." Jacques said with a satisfied smile. I continued to touch it all over and it was having an effect on Jacques.

"Have you some ideas on what you want to do with that 10 inches?" Jacques inquired.

"I wouldn't mind watching you sink it between my girlfriend's thighs." I replied. I was so far gone I was giving up Tonya to Jacques.

He grinned. "We can arrange that later on and it will be my pleasure, but right now it's just us. Why don't you suck on it for me?"

I had no inhibitions left. I leaned forward and grabbed the large ebony prong at the base. It barely bent upwards it was so turgid with blood. I hovered over it for a bit and took in the musky smell. Then I opened my mouth wide and slid it down my throat. I immediately started to gag as he touched the back of my throat. I had no idea how to suck another man's dick and it showed.
"Easy baby easy." Jacques said softly as he looked down at me. "Just take the head. Relax baby. Oh God yea that's it... so nice." He cooed as I sucked the head back into my mouth. I used my fingers on the length of the shaft and his scrotum. I felt that his balls had started to rise up into the sack. I knew then that I was really exciting him.

I was more relaxed and really getting into sucking Jacque's dick. I was able to get more and more of the thick shaft down my throat with each gulp. Jacques was urging me on between grunts and groans. I thought about how Tonya had joked about the big cocks in a porno movie we had watched, calling them donkey dicks. I knew they had excited her. How jealous would she be watching me suck off this big black hog of a penis.

I felt Jacque's hand in my hair as I bobbed my head up and down. He was controlling my movement. Suddenly what I was wearing became a part of what I was doing. The pumps, the stockings, my make up and the lipstick that was gliding over the black man's manhood made me feel so feminine and I knew I looked it. I was absolutely busting out of my sheer blue panties. I reached down and stroked it. The hardness was the only remnant of masculinity left in me.

That's why I didn't protest what came next. Jacques lifted my head out of his crotch. His dick glistened with my saliva. He stood and began pouring some of the oil onto his manhood. I could have called a halt to it. Said fuck it. I'll walk home you fucking queer Negro get another bottom bitch. Yet I just watched him as he continued to smooth the oil along the length of his erection. The black seemed to glow like some hard metal. He walked behind me and got on the couch. My knees were tucked underneath me and my ass was in the air. Hell I wanted it why not make it easy for him.

I felt his finger first. It pressed against me and then it slid inside.

"Oh God!" I gasped as all the air rushed from my lungs. I squirmed underneath his hand as he wiggled around inside me. It hurt like hell at first and my erection went limp.

"Relax baby just relax. You know you want it. Just let me loosen you up." Jacques cooed as he rubbed my back with his free hand and continued to probe me with his other. I grabbed the arm of the couch and groaned. He was right. I so wanted to experience being fucked like a woman but I was scared. If it hurt like this with a finger what would it feel like with an 11" black cock up my backside. Jacques was pumping his finger in and out with ease now and my cock had inflated again.

"You ready?" He whispered into my ear as I felt his hands on my hips.

"MMMMM do it to me." I purred trying to hide my apprehensiveness. I smiled back up at the black man as he climbed on top of me and began working his way inside me. It was a blunt pain at first as the bulbous head cleaved its way past my sphincter. I spread my legs some more to accommodate him but it still felt like a freight train was riding up my ass. I was moaning loudly and tears were streaming down my face but Jacques was relentless. All at once I felt a rush of flesh. My sphincter surrendered and Jacques was balls deep into my rectum. He rested his torso on my back and reached around and gently tweaked my nipples and began kissing my neck and ear. He was doing his best to relax me and keep me sexually excited. At first his caresses did little as the pain was incredible.

"Oh fuck Jacques! It's so big! It's too big!" I howled. I felt like I had to pee real bad and more importantly I thought I might get hurt taking this much cock up my ass. Yet the wiry black man had me and he knew it. There was no turning back. He was going to fuck me and there wasn't a damn thing I was going to do about it.

"How does it feel my sweet?" I heard in my ear.

"Christ! Like I'm on a shish ke-bab! How do you think?" I squealed.

"Relax baby" He whispered for the millionth time. "and you shall enjoy. Just move your hips back and forth." I did as I was told and I could feel his dick slithering in and out of me. "Oh God yes baby that's it Now you're doing it. We're dancing together now." Jacques stuttered out in an ecstatic tone.

He began to fuck me, wrapping his arms around me and undulating his hips up and down. I clung to the couch and just took it as Jacques gave it to me harder and harder. I could hear the wet sticky noise of his balls slapping against mine. It was so intense, so much more exciting than any sexual experience I had ever had with a woman. I didn't care how taboo this was in fact it only turned me on more. Meanwhile Jacques kept up his unrelenting assault on my ass. I had relaxed completely and he had me singing like a choir girl. There was very little pain now, just a slick wetness between his dick and my rectum.

We were both dripping with sweat. I could feel Jacques' warm moisture draining off his body and onto my back. His hands seemed to be everywhere caressing every part of my body all at once. Although I had never been with a man before I knew that this black stud had superior sexual prowess and he was in total control. He pulled me up into a kneeling position and then rolled me back on top of him. I was sitting on Jacque's lap with his thick black dick still buried 11" up my ass. I looked down at my legs. The stockings were soaked with sweat and oil and the high heels turned my leg muscles just right. My chest had turned a crimson red. I realized that this was a close as I would ever come to being a woman.

I was grinding my ass into my lover's pubic hairs and he was jerking my cock. I had leaned back and we were kissing when it happened. A surge of pleasure rushed through my loins and up through my cock. It spewed out of me as a big thick load of semen. It went everywhere, stream after stream of hot cum. Later Jacques told me he saw one of the cumshots gush a couple of feet in the air only to splatter on one of my stockings.

Now Jacques pushed my buttocks a bit higher so I was squatting over him. He proceeded to thrust up into me at a brutal pace. There was more pain but I just took it. It was worth it just to give so much pleasure to the black stud beneath me. All at once he grabbed my hips and pulled me back down totally impaling me on him. I let out a high pitched sigh and I felt Jacques shaking beneath me. His moans joined my cries as he came inside me.

I fell back onto the black man's heaving body. He hugged me and I turned and kissed him. I was already hard again as we lay together on the couch. I ended up spending the night in Jacques' bed. We made love twice more during the night and I was in heaven. As I lay there with Jacques' arms around me I knew things had changed for me. I had discovered a new and wonderful part of me. Getting turned on driving around town would no longer satisfy my feminine side. Experiencing a man sexually had become the ultimate turn on. And this wouldn't be the last time I tried it.