It is amazing the things a man will do to get laid. It was Halloween and I was being dragged to a costume party thrown by a few of my girlfriend, Caroline's friends. Although Caroline was a prim and proper insurance underwriter during the day she hung out with a rather arty crew of liberals.
They enjoyed having yelling contests about politics and being sanctimonious about everything else. While I agreed with many of their views, for the most part I thought they acted a bit self important. Caroline had been insistent about going to this party to the point that she had been witholding sexual favors ever since I had tried to get out of it. This was over a week ago and I was at the breaking point. You see when it comes to sex Caroline tends to abandon her conservative nature and adopt the more experimental lifestyle of her artistic comrades. She would try just about anything and was usually exceptional at whatever form of sexual pleasure was performed. I couldn't get enough of her. Consequently I knew I would have to put up with the party and the "great idea" my girlfriend had for our costumes.
On the night of the party I was in an absolute panic. What Caroline wanted to do was beyond my furthest boundaries.
"I wish you would stop worrying. None of your friends will see you and my friends will love it" Caroline suggested.
I was thoroughly convinced that this was a set up by Caroline and her friends. "Honey we are both 30 years old don't you think we have outgrown this sort of thing?" I replied from the bathroom.
Caroline laughed "Outgrown? Outgrown having fun and trying new things? I hope not! Now get down here or we will be late."
I finished dressing and then shuffled as best I could out through the bedroom to the foyer. Caroline heard my approach and without looking up coached me. Honey put the balls of your feet down first not the heels. It's the opposite of your normal step." She looked up. "Whoa you have incredible legs. What's your inseam again?"
"I don't know. What the hell does it matter. This fucking sucks." I growled.
"Well I have to admit your lips our nice and full for that sort of thing too." She smiled at me tugging at a few spots on my costume.
"Thanks for the encouragement." I sighed. "How long are we going to have to stay anyway?"
You see Caroline's great costume idea was to dress her as a man and me as a woman. She had thrown on a suit and tie and a pair of wingtips she had picked up at a thrift shop. While there she had picked out a long sleeve sequined black cocktail dress for me. She was also able to scrounge up a matching pair of black pumps. I had a full head of brown hair so Caroline simply styled it into a sort of lesbian look. I had to admit after her make up job I was actually passable as a woman.
It didn't matter if I looked like a runway model though. I was scared to death. This was against everything I had stood for in my life. I felt certain someone I knew would see me. We drove to a large mansion that was a museum on every other day of the year. For the past five years a few of Caroline's friends had been renting it for this party. Before meeting Caroline I would have been all over a party like this one. There would be women everywhere. Unfortunately tonight I would be one of those women.
I was still learning how to walk as we said hello to some of the 250 guests. Many of the women were amazed at how I had turned out. There were a few other guys who had attempted the same crossdressing feat but most had failed miserably. I sensed that some of these idiots were actually jealous of me. This backed up my theory of Caroline's male friends simply being a bunch of donkeys. I mean what kind of guy would want to dress as a woman. I was not enjoying the attention as the girls and some of the men ogled my legs and asked questions about my pantyhose. They were seamed and had some sort of Cuban type heel. I let Caroline handle the technical questions while I went to get a much needed drink.
I stood in a large room where a bar was set up and I got a good dose of what it was like to be a woman. It was pretty crowded and guys were staring, touching and just being animals. Most of them had no idea that I was a guy until I spoke. This was going to be a tough evening so I grabbed two drinks for myself and one for Caroline. As I lifted the drinks I felt the presence of someone behind me and then felt a hand on my bare back. I turned and saw that it was a tall black man dressed as a vampire. He said hello and I smiled and walked away. By the sound of his voice I could tell that this guy was more into show tunes than baseball. I felt myself blushing a bit and I knew that this only made things worse. He probably thought I was just shy and not scared out of my wits. I figured that there were more than a few gay men at this party so I made a point of sticking close to Caroline.
As the night progressed I got a bit drunk and loosened up. While Caroline told me she really appreciated my change in attitude she had no idea how it was going to affect the rest of the evening. I really got into dancing with her. There were so many wild costumes out on the floor, we all looked like assholes trying to move to the beat of the music. It turned me on knowing that underneath Caroline's starched outfit was her brick shit house of a body. I had to move so differently in a dress and high heels. The hem of my dress only went to mid-thigh and the material was a little constricting. Even though I was bombed I was still self conscious. Yet the smoothness of the material I was wearing was also turning me on. I was literally rubbing myself to an erection with the pantyhose.
I had gotten used to all the touching and grinding. There were even a few women trying it so all the attention was thrilling. As we walked off the dance floor I ran into the black vampire again. I was laughing at something as I squeezed by him. He looked at me and smiled. "You are very pretty." I let him run his hand down my shoulder and into my dress. He gently cupped my breast and gave my nipple a tweak. My cock gave a jump under my dress. I walked away thinking that that was way too close for comfort.
I had lost track of Caroline so I decided to take a pee, find her and head for home. There were just too many guys coming onto me. I had found a bedroom on the third floor with a bathroom. It was private and I had already used it a couple of times. I pranced up the stairs and closed the door to the bathroom. I had cut a slit in my hose so I could take out my prick to pee. When I pulled it out this time it was pretty hard. I had just finished when I heard the door to the bedroom close and the lock turn.
I looked out the door and saw the vampire walking towards me. He said hello, smiled and gave me a kiss full on the lips. I tried to push him away as he put his arms around me. He was extremely strong and anchored me to his body.
"Do you realize that you just kissed a man?" I gasped rather indignantly.
He nodded and kissed me again and then moved down to my neck and ear. I told him to stop but then he found it. He gently grabbed me and began stroking through the silky smooth material. It had been almost two weeks since anyone had touched me there and it felt incredible. I decided to not fight too hard for the time being. I hung onto him as he worked me over. I remember thinking that it was okay. He was pleasuring me and as long as he did that it didn't matter that it was a man. After all I was dressed as a woman.
I started to moan a bit and hump against his hand. "That's it. That's my girl." He cooed into my ear and then he moved his lips back to mine and slid his tongue into my mouth. I let him do it. Things were happening so quickly but it didn't matter, I was too far gone. So when he pulled out his dick it only made my heart beat that much faster. I reached down and touched it. I had never put my hand on another man's penis before. It doesnt matter that I had touched my own so many times this felt so different. The jet black prong was as hard as mine now. The major difference was its size. On a good day I may measure 6". This man was probably packing a solid 9 inches.
"You like it big like that?" He asked in his sensuous lisp.
"We shouldn't do this. I can't. I'm not queer." Was all I could manage as my last protest.
He chuckled in a low tone. "You don't have to be gay to be submissive. Now I am going to make you forget about that pretty white woman of yours for a little while."
He reached behind me with both hands and grabbed my buttocks and then lifted me onto the bathroom countertop. I simply sat there and let him push my dress up my thighs. He grabbed my cock as it lewdly popped out of the pantyhose seam. He stroked me and told me to lift my legs up onto his shoulders. I obeyed. I was quickly finding that I liked being told what to do. My heart was pounding a mile a minute.
I felt him further tear the seam in my hose. He was now able reach my ass which he did with a finger. As he rubbed my rosebud with one finger, he pulled out a small tube of grease from his pocket and deftly applied it to his throbbing manhood. I was totally excited. I was breathing like I had just finished a marathon and we had not even started yet. The tall black man grabbed my thighs and caressed them.
"Just relax sweetie, this is going to be so much fun." He grinned at me like an animal that had just taken down its prey.
With that I felt something blunt against my sphincter. After a bit of an effort my muscle relaxed and the long black tube began to slide inside me. The pain was sharp and very real. I let out a gasp as I felt the huge dark purple head ease into my rectum. My own cock went limp and I felt as if I had to pee again. The pain intesified as the vein covered shaft pushed its way further inside me.
I was now flat on my back, my head propped up against the wall and my ass hanging off the counter. Dracula had grabbed my calves for leverage and I reached down and grabbed his thighs to support myself.
I could hear the greasy lube working as he began to fuck me with that big black dick. As it moved in and out of me I realized that my own cock was hardening again. Dracula's thrusts were so hard now there was a slapping noise everytime his balls hit my ass. That and my uncontrolled grunts and moans were all we heard. He began to really lean on me pressing my legs against my chest. We were kissing now as he made short powerful thrusts into my body.
After about 10 minutes of some very intense fucking he wanted me on my feet. So he pulled out of me. The feeling was so wild, not to mention the sucking noise it made as the head plopped out of my ass. I stood up and put my arms around him. Our tongues entwined and I explored his warm mouth. It was so passionate being in his arms.
"Let me fuck you from behind." He coaxed.
"Whatever you want." Was my reply. I was so excited that I would have done anything for him. I turned around and spread my legs. He came up behind me and pressed me against the bathroom wall. Then quickly, he was inside me again. This time it was easy. Hell I was so relaxed you could have driven a bus up my ass. He grabbed my hips and really started fucking me. I mean he had me singing like a rock star and my high heels actually left the ground as he thrust into me.
I felt his hand down on my erection. He was jerking me and fucking me at the same time, The sensation was so intense. It was at this point that I knew this was the most incredible sexual experience I had ever had. Dracula was right, forget Caroline this man's gorgeous black dick had me in orbit and now he had me cumming. I squealed as the hot sperm shot out of me and splattered against the wall. My body bucked back and forth and my legs convulsed as they dangled in the air.
Now it was Dracula's turn. His breath steamed onto my neck like a charging bull's and I felt his body stiffen behind me. His thrusts dissolved into complete wetness as his seed spewed out of him and into my rectum. Slowly his motions lessened and he leaned against me with his arms around me. We were that way for a minute until we heard a gentle knock on the bedroom door.
We kissed and then straightened ourselves up as quickly as possible. We opened the door and moved by two women who were waiting to use the bathroom. They were both dressed as Marie Antoinette. When we passed I caught the eye of one of them. By the features of her face I could tell that underneath the outfit, heavy make up and wig that she was a very attractive woman. She gave me a smile and her eyes drifted over to Dracula and then went wide with comprehension. I looked back at her again and she was still smiling. "How did that feel?" She cooed after us. I could hear her friend laugh from inside the room. God help me if they were friends of Caroline.
The black stud discreetly gave me his number and told me that this would not be the last time he got his dick up my ass. I told him he was welcome anytime and went to find Caroline. She was very suspicious of my disapearance and the several runs that had mysteriously appeared in my pantyhose. I told her that women's clothes and I just didn't mix as I drove home trying to figure out where a man went to find more outfits and lingerie. Afterall I had a new boyfriend to keep satisfied.