Last October my girlfriend Kelly and I were drinking wine and playing cribbage on a cold, rainy night. After dating her for six months we usually stayed in on weekends. I consider myself very lucky to be dating her. She is an incredibly beautiful brunette and has a perfect 36C-24-26 figure on her 5'5" frame. I, on the other hand am no Greek god at 5'9,"145 pounds. She says I am good looking and she loves me for being attentive, open minded, and thoughtful. We have great sex; having tried everything a man and a woman can do together. Anyway, after three games each, Kelly recommended we make the tiebreaker interesting. I asked what she wanted to bet. She said that the looser would have to indulge the winner in a sexual fantasy. The possibilities raced through my mind and I quickly agreed. I figured that even if she won, it would be something new.
Kelly won easily so I asked what I would have to do for her. Her big brown eyes gleamed with mischief as she told me about a big Hallowe'en bash downtown that she wanted to go to. She said that she would pick the costumes for both of us. I was a little disappointed, as it seemed pretty tame at the time.
Kelly arranged a room at the hotel where the big Hallowe'en party was being held. That way we could party and not worry about driving home. We arrived in the afternoon with four bottles of champagne, which we got into right away. Kelly had brought several other bags as well. She then drew me a bath and handed me a razor. I was instructed to shave off all of body hair. It was apparent that she wanted me to dress as a woman, which was fine as lots of guys did this for Hallowe'en. I shaved my face extra close. Kelly helped me the tricky spots like my butt crack, armpits, and balls. She made sure my legs were very smooth. At one point she asked, "Not easy being a woman is it?"
When I was done I had a huge hard on. Kelly, seeing it, dropped to her knees and gobbled it into her throat. She sucked me off with abandon and within minutes I let a gusher go into her waiting mouth. She then shocked me by placing a kiss on me. My mouth was already open and I quickly realized that she had not swallowed any of my cum because she was giving it all back to me. She had never done this before but I liked it and ate up all my jism from her mouth. I then licked her chin and neck clean. We kissed passionately for about ten minutes before she broke it saying, "good girl, now let's finish getting you ready."
Kelly got her make up bag out and spent over an hour plucking my eyebrows, putting false eyelashes and nails on and applying make up, lipstick and perfume. During this time we drank enough champagne to sink a ship. When I was finished Kelly got herself ready. She then put a blond wig on me that made me look a bit like Donna from 'Baywatch'. I honestly looked really hot.
Kelly gave me a bag with a pair of false boobs, a lacy white push up bra, a white garter belt and a pair of white thong panties. I dropped my robe and put them all on. The panties had a pouch which kept my dick stuffed neatly between my legs and revealed no bulge in front. I then put on a pair of white fishnet stockings, and white high heels. I tried walking around in the shoes. Kelly instructed me on how to walk and after an hour of practice I was comfortable. In the meantime, she pulled out the costumes. They were nurse's outfits. She handed me my dress which fit snug, and was shear enough to see the underwear underneath. It was very short too, not even reaching the top of my stockings. Kelly told me to undo one button at the top and one on the bottom. She put on a pair of stay up white stockings with lacy tops, white pumps and her dress. She decided to go commando (no bra or panties), which showed off her dark nipples. Her dress was equally as small and barely covered her crotch, with one button undone on the bottom. She undid two on the top to show some ample cleavage. We put on our nurses caps and she said, "let's go!" Despite all the champagne, I was a little nervous. To make matters worse, my girlfriend told me not to talk too much. She didn't want people to think that I was a man dressed as a woman but wanted everyone to think we were two good looking women dressed as slutty nurses. It was her fantasy so I did as she asked. I told her I needed a shot of JD as soon as we got there. She told me that I could have one, but ladies drink wine.
We turned a lot of heads as we strolled in. We received numerous catcalls, and wolf whistles which we ignored. At the bar we quickly downed a shot of JD then got glasses of white wine. Before we could pay, we heard a man's voice telling the bartender that he would take care of it. We turned to see two tall, muscular black men, one who was wearing only a loincloth and a necklace made of bones. Kelly smiled seductively at him and thanked him. He introduced himself as Anthony, and his friend Reggie who was dressed as a vampire. I whispered in Kelly's ear that I needed another shot. Anthony said, "No secrets girls, what are you talking about?"
Kelly piped up, "My friend Heather here was just asking if I thought you were wearing anything under that loin cloth, she's a little shy." I could have bust. Before I knew it, Anthony took my hand and placed it under his cloth. I could feel an enormous prick. He smiled then excused himself for a minute. Reggie took us to the dance floor where we met two more friends of theirs, Doug and Julius who were also good looking black guys. Their hands were all over us, grabbing our asses and squeezing our tits. Kelly seemed to be encouraging them. I decided to take a break, and Reggie escorted me off of the dance floor. He put an arm around me with his hand on my bum cheek.
He whispered sexy things in my ear like "you are a hot babe, I'd love to sex you up." and stuff like that. Anthony was waiting for me my wine. He glared at Reggie who let go of me. It was clear who the leader of this group was.
He handed me my wine, then took my other hand and placed it back inside his loincloth. As I touched his throbbing prick again, he gently caressed my ass as he asked, "Did you miss me?" I simply nodded a response still appearing shy.
Anthony's cock started to stiffen so I quickly removed my hand. He took my hand and led me to a both where yet another friend, Darryl, was watching the table. I squeezed into the both between Darryl and Anthony with Reggie on the outside. I had gulped down my wine and Anthony ordered another round. I nervously sat with legs crossed tightly while Anthony put an arm around me and a hand on my thigh. I drank quickly, and my glass was continually refilled. I was feeling looser, and bolder. Anthony placed my hand on his cock again. This time I left it there and massaged him to hardness. When I realized that it had been a while since I saw Kelly, I leaned over to whisper to Anthony that we should go look for her. But as I did he turned to me and pressed his big black lips on my mouth. His long tongue invaded my mouth. I found that I enjoyed the strange sensation and soul kissed with him while I melted into his arms. I lost track of time necking with this black stud. After what seemed an eternity, I heard Kelly's voice and turned to see that she had returned to the table with Doug and Julius. She smiled at me as I new I was busted. Her two partners however, had spread her legs and I could see they each had a pair of fingers buried into her naked snatch. I could see where she wanted this fantasy to go and decided not to fight it.
As she french kissed with Julius, Doug undid a button on her dress and pulled out one of her tits. He immediately sucked on her erect nipple. Being a bit wasted it took Kelly a second to realize the spectacle she was causing and stopped her friends. While placing her wet boob back into her nurse whites she shocked me again by saying that we should all go up to our room and continue the party there. Up until then I figured we were only fooling around a little then dumping these guys.
Soon we found ourselves in the elevator, Anthony pulled me to him and we continued to kiss passionately. Catching me off guard, he placed his hand between my thighs and up to my crotch before I could squeeze them shut. His hand was touching my panty covered hard cock that was wedged up tightly in my crotch. To my amazement he didn't react at all. He just continued to kiss me, as I felt puzzled yet glad that he didn't beat the shit of me right there." Now that he knew, how far would he take this?" I thought to myself. I could see Kelly watching us and she smiled her approval, as she undoubtedly saw where Anthony's hand had roamed.
In our room, Kelly opened another bottle of champagne, which we all passed around. I had gone to the bathroom to fix my makeup, being sure to add lots more lipstick. I felt good as a woman, and was turned on like crazy playing the part. Back in the other room, I sat on the edge of the bed. Anthony stepped right in front of my face and pulled his black tube steak out. I gasped open mouthed in shock, staring at a thick, purple headed, eleven-inch cock. He stepped closer, taking advantage of my open mouth by placing the tip of his cock on my tongue saying to me, "You've been wanting this all night baby, take it."
As much as I hated to admit that, it was true, I had wanted this.
Tentatively, I took the head into my salivating mouth. Anthony enjoyed the wetness, and encouraged me to take a little more in. I reached around him and placed my sweaty hands on his hard ass. They felt so good. I was so into it that I grabbed hold of his cheeks and pulled him deep into my throat.
From past experience on the receiving end I know how great that feels. As the end of cock pressed on my throat, I relaxed and swallowed. "Wow! You really know how to suck cock baby, "was Anthony's only expression. It was part knowing the equipment, part knowing how I like it, and part beginner's luck.
I had completely shut everyone else in the room out of my mind until I herd Kelly cheer, "Ya, you go girlfriend!" and various whoops and hollers from the guys.
Me, I happily kept on sucking that glorious big dick. I pulled it out after a few minutes so I could give it a kiss and tongue bath all over. I then licked and sucked on his massive balls, coating them with my saliva. After a couple minutes of ball worshipping I went back to sucking his big cock.
When he got really hot, Anthony grabbed hold of my head and began face fucking me. Within a few minutes he plastered the back of my throat with his torrent sperm. I dutifully swallowed as much as I could in a lady like fashion but a lot escaped my mouth and ran down my chin. I loved the taste of his cum.
Before I could fathom all that happened, Reggie had his erect dick out, saying how he wanted to fuck me. Before I could panic, Kelly piped up, "No, Heathers on the rag. If you want pussy you can fuck me, other wise Heather sucks cock better than anyone I know." As I looked over at my girlfriend, I saw that the boys had her dress open and were squeezing and sucking her big white tits. Julius had two fingers jammed up her twat as well.
While engrossed in the display Kelly was putting on I didn't notice the black side of beef slapping the side of my face. I turned my head only to engulf Reggie's pipe. It was big and thick though not as long as Anthony's.
I sucked and licked it with equal vigour as I watched Kelly getting fucked by Julius. After he came inside her, Doug jumped in and buried his schlong into her wet snatch. Meanwhile Reggie blew his nut deep into my throat and I swallowed it all.
Next I blew Darryl, than Julius who still tasted of my girlfriend Kelly. I tried sucking both Julius and Doug at the same time, which was great except when they came at the same time I couldn't swallow either of them and took both loads on my face. I was a mess. I scooped up what I could and ate it. Realizing that my makeup was gone I went to the bathroom to freshen up.
When I was freshly dolled up I returned to find Anthony balls deep in Kelly who was on her elbows and knees doggy style and sucking Reggie at the same time. I felt suddenly jealous, though not of my girlfriend getting fucked but of Anthony cheating on me with another women. I know it sounds stupid, but...
Noticing my expression, Anthony pulled his foot long log out of her slurping pussy much to her disappointment. Reggie took his place and she felt better. Anthony came over to me and said, "Heather baby, how would you like my big dick here up your sweet white ass. Winking at me he said, "I'll just pull your panties to one side so your tampon stays put."
I knew that he knew what I was, and honestly, I really wanted him inside of me. I slowly bent over the bed with my ass high in the air. I had never felt so lewd in all my life. My skirt was already riding up over my ass cheeks, exposing my garters and stocking tops. Gently, Anthony pulled my white panties to one side, taking my engorged prick with them. Next thing I felt was his face between my globes. His wet tongue licked trails up and down my crevice and soon after snaked its way deep into me rectum. He lovingly tongue fucked my anus in preparation of the main event.
After ten minutes of this Anthony stood up and started pressing the end of his slick magic wand into my bum hole. Although it hurt, I pressed back onto him, wanting it all. Eventually he was buried deep inside my bum. My muscle was finally relaxed enough for him to start fucking me. I whispered to him to fuck me hard. He did. The whole time he pounded my ass he kissed the nape of my neck and licked my ears passionately. I was also watching Kelly who had Darryl in her pussy, Reggie up her ass and Julius in her mouth. She looked as if she were in heaven.
Doug sat in front of me with his erect nine inches and I eagerly started sucking him. I went at it with double the gusto, slurping and slobbering all over his dick with each deep-throated stroke. I was really into getting double banged but I easily got Doug off in record time as he shot a monster wad deep into my stomach to join the other five. While licking him clean he could only exclaim, "Damn girl!" I was then able to concentrate my efforts on the foot long dick boning me up the ass. I pushed back to meet each of his strokes, making his balls slap against my satin covered pair. I was lost in a trance, my mind floating when I felt a warm, wet sensation on my crotch. I soon realized that it was my own come soaking my panties and lubricating the junction of Anthony's cock and my asshole. Feeling this sensation, Anthony increased his thrusts into me at a blistering pace. With a grunt he climaxed, filling my rectum with his salty goo. He lied on top of my exhausted body, kissing the back of neck until his member eventually went limp enough to pull out. He then rolled me over, placed his mouth on mine, and we shared the most passionate kiss I could ever remember.
By then everyone was about spent. Kelly had polished off her lovers and they were getting dressed to leave. Soon Anthony joined them and the five of them left. I looked over at Kelly who was buck-naked and was staring back at me with a gleam in her eye as if she were saying, "I want more!" Her pussy was red, swollen, stretched, and flowing with the cum off four guys and her butt was leaking a load as well. She looked incredibly sexy. She noticed me staring at her crotch and asked, "Hey Heather, wanna eat me?" in a playful voice.
I dove right into that overflowing honey pot and lapped up all hers and the guys' juices. It was the most delicious thing I've ever eaten. After swabbing her pussy and asshole clean, and giving her a tremendous orgasm, she pulled me up to her face and kissed me. It was equally as hot as the one Anthony and I shared. Kelly mumbled amidst our lip lock for me to fuck her. "Not a problem, "I thought as my dick was like iron again. I ripped off my panties and allowed it its first freedom all night. My cock felt bigger than ever as I eased it into my girlfriends gaping snatch. She was so stretched that I could barely feel the sides but I was so turned on it didn't matter. I pumped her fast and filled her with my own load in a few short minutes.
After we just lied there, holding each other, kissing. It was six in the morning. She admitted to me that she planned the whole thing. Anthony was a co-worker of hers who she has lunch with sometimes. He had opened up to her that he fantasized about having sex with a transvestite one time. She added that she always wanted to see me with another man and figured that I would go for it. She has no idea how much I enjoyed it. She also asked Anthony to help her with her fantasy of being with several partners who in turn set up his friends. None of them knew that I was a man. I was very happy with the evening and told Kelly that I loved watching her getting fucked, and that felt extremely sexy dressed like a woman and how I really got off sucking cocks, and getting fucked by a man and would do it any time she asked. I told her that she would now have to do another woman while I watch though.
She says she's all for it. I can't wait.