Note: This story is loosely based on two separate events that occurred in my life. The names have been changed for obvious reasons. I took some creative license but the facts are pretty much as stated. Enjoy! Let me know what you think!
As a musician, I meet all sorts of people but most of my friends are other musicians. We just seem to understand each other better. Years ago, I had a friend who was a keyboard player. We all called him Dee because he had that young Billy Dee Williams looks. Young, dark skinned, moustache, cool hair, the deepest darkest eyes and a smile that could melt ice.
Dee mostly played pop, R&B, soul, etc. I moved to another state and as often happens, Dee & I lost touch with each other. Well as luck would have it, I wound up on the road and while on a club tour, ran into Dee. I was stoked! Dee looked pretty much the same except that his hair was longer and he no longer had the moustache. We chatted for a bit but then I had to get ready to do the show. We exchanged numbers and email addresses and looked forward to catching up.
I had a lot of down time, as I was playing clubs that were mostly in small towns, so I didn't have much to do in the daytime. Thank goodness for laptops and the Internet! Over the next few weeks, Dee and I spent a lot of time chatting online. It turned out that Dee was still working as a musician but was mostly playing gospel in a black church. Dee had a fair bit of free time during the week and on Saturdays and Sundays after services. I have to say that I was a bit shocked at Dee playing gospel. I remembered that Dee always liked to party pretty hard and always had some good sex stories.
Once the tour was over and I was back home, Dee and I continued our chats. Then one day, Dee felt the he needed to tell me a few things. It turned out that Dee was gay. I was neither surprised nor upset by this. I told Dee that people are just people and it doesn't matter to me who my friends sleep with, as long as they're happy. Dee was relieved to hear this as he said that he'd always valued our friendship.
As it turns out, Dee had a partner, Greg. They'd been living together for some years and were raising Greg's son together. It also turned out that although Dee was playing gospel, he was still as wild as ever. Wilder, in fact, than I had ever known! It seems that they both liked to party and liked their sex a bit on the kinky side. Their son was aware of their sexuality but they kept the partying and kinky stuff hidden from the boy, as I guess most parents do.
One day while we were chatting, Dee felt the need to make another confession. He and his partner both occasionally liked to cross dress. He said that there was a certain excitement to picking up "straight" guys and having sex with them while dressed. They often would photograph and/or film their exploits, sometimes even having sex with their web cam on. At this point, Dee asked if I'd like to see how he looked dressed. I guess you could say curiosity got the best of me and I agreed. Well, I have to admit that Dee makes a damned good looking woman! I told him I was impressed and that if I didn't know better, I would have just thought he was a hot black chick. His partner Greg came in the room then and waved Hello via the cam. He too looked pretty good!
Life went on as usual, with me gigging at night and Dee and I often emailing or chatting the day away. Dee would often mention sexual exploits and I have to admit, some of them were pretty hot. Dee would email photos from time to time and I'd be lying if I said that it didn't turn me on. When cross-dressed, Dee looked really hot! Long, shapely legs, a great build and really, one of the finest Asses I'd ever seen. Dee would sometimes send photos of his cock. This I found a tad confusing. While Dee's sexuality didn't bother me, I wasn't sure why he was sending me these photos. Did he think that I was gay or was he maybe trying to seduce me? Nah...couldn't be. We're old friends and well, I guess sometimes people become just that comfortable with friends.
It was Memorial Day weekend and as luck would have it, the shows I was booked to do had to be rescheduled due to some problems at the club, so I had a free weekend with nothing to do. While chatting about it with Dee, he said he wished I could come visit for the holiday but understood that the four hour drive would be too much to ask. I figured what the heck, I've got a tank full of gas, money in the bank and a few days off so I decided I would go visit Dee. He was thrilled! He said he'd pick up steaks to put on the grill and I said I'd bring some beer and wine. I was really looking forward to hanging out with my old friend, even if he was a bit different these days than I'd remembered.
I pulled up to their house and as I walked up to the front porch, I could hear Dee practicing piano inside, playing some upbeat gospel number. He hadn't lost any skills over the years, that's for sure! I'd say he was probably the best keyboard player I'd ever known! I stood on the porch for a while just listening.
After a few minutes, I rang the bell and Dee answered. I was hoping he wouldn't be dressed like a girl but he was. He wasn't dressed slutty or anything, in fact, quite the opposite. He was wearing a very nice blouse, short yet tight shorts and sandals. He invited me in and as soon as I set down the beer and wine I'd brought with me, he gave me a big hug. He was wearing perfume and I have to admit, he smelled good! He introduced me to his partner Greg, who was suffering from a bout of the flu. Sick or not, Greg was also dressed, wearing a skintight black minidress, stockings and high heels. Their son, it turned out, was at his mom's for the holiday weekend and Dee & Greg were ready to party! Little did I know, I was going to be the party favor!
Dee asked me into the kitchen so that he could work on dinner. It was looking like rain, so Dee had decided to cook the steaks inside on the stove instead. We were having beers and just catching up and having a good time. When dinner was ready, we all took a seat at the table and let me tell you, it was one of the best meals I've ever had! Strangely, it didn't seem odd sitting there having steaks and beers with two guys dressed like women. That is until I felt someone's foot rubbing my ankle under the table. It was Dee. I figured he was just joking around but seeing him sitting there looking like a woman, and knowing some of the stories he'd told me about their sexual exploits, I was more than a little aroused and curious of the possibilities.
After we finished dinner, Greg went into the kitchen to get us all more beers. Dee lit a cigarette and told me that they were both hoping that I might consider having a threesome with them. I almost choked on my beer. Dee apologized for being so abrupt and added that with Greg still feeling ill, a threesome would probably be out of the question. "So what do you think? Are you up for a little gender-bending?" Dee asked with a laugh. "It'll just be you and me though, old buddy. Are you up for it?"
I was speechless. Dee just looked at me and laughed and said, "Well, at least that's not a NO!"
I told Dee that while I considered myself to be open-minded, I just never really thought about a situation like this.
"But you're not against the idea, right?" Dee smirked.
"Well, no but..." I tried to think of how to finish but Dee stopped me.
"Look, if you're uncomfortable we don't have to. We can just hang out and party like old times. And if you're really uncomfortable, Greg and I can change into guy clothes. It's just that this is how we usually dress around the house and well; we both think you're really hot. I always did. When I showed Greg your picture, he agreed."
I really didn't know what to say. If I didn't know that they were both guys, I probably wouldn't have guessed and would have just dealt with the consequences when/if they came up.
"Look Dee, really, I'm flattered but man, this is all just so sudden. But I'll be honest; I think you look really hot as a girl. But man...I just don't know..." I said, trying to be as honest and open about the subject as possible.
"Hmmmm, I have an idea. Wait right here, drink your beer and I'll be right back." Dee suggested, with a sly look in his eye.
So there I sat at Dee's dining room table, drinking a beer and wondering just what my old friend had in mind. Part of me was a little freaked out but a bigger part of me was getting really turned on.
After a few minutes, Dee came back in the room. He had changed into a really sexy black bra and panties. "Does this help?" he asked with a sly grin.
My jaw just dropped. My mind knew that this was my old friend Dee but the person standing in front of me was a hot `woman' who really wanted me. I stood up and it was obvious from the bulge in my pants that the answer was yes. I walked over to Dee and kissed him as passionately as I had ever kissed a woman. I don't know if it was the weeks of chats, the smell of the perfume he was wearing, the beer or what...but I was ready for anything at this point. Dee returned my kiss just as passionately and soon our tongues were touching and exploring each other's mouth. My dick was as hard as it has ever been and so was Dee's! I could feel it against me and it was really turning me on.
Dee took me by the hand and led me into the living room, where his piano and organ were. The sight of his perfect ass in those tiny black panties completely overwhelmed me. I maneuvered Dee to his organ bench and told him, "I have to see that ass!"
Dee put his hands on the organ bench and leaned forward while I dropped to my knees and slowly pulled down his panties, revealing the most perfect black ass I had ever seen. It was a big, round, smooth bubble butt...and it was right in my face. Something overcame me and I just started kissing and licking Dee's ass cheeks. I had never done anything like this before but it just felt so right!
Dee started moaning and I started to lick up and down the crack of Dee's ass. I just couldn't stop myself! The more I licked, the more Dee moaned. The more Dee moaned, the more I licked. I was burying my face in my old friend's previously panty-clad ass...and I wanted more! I was stretching my tongue as far as I could up his asshole, tongue fucking him. It was great! It was better than any pussy I had ever eaten!
We heard Greg come in the room and he asked if he could take some pictures. Neither of us said no...Dee was too busy moaning and I was too busy tongue fucking Dee's perfect ass. I reached around with one hand for Dee's cock. It was massive! Fully erect, it felt like it was a good 8-9" and thick! With my other hand, I started to jack myself off. It was just crazy! Here we were, two old friends, and I'd never been with a man before, and my face was buried up my friend's ass. The excitement and lust I was feeling was like nothing I'd ever felt before.
Dee stopped me briefly and turned around. "Suck my black cock!" he ordered and I was ready! I took it in my mouth as far as I could. I tried to shove the whole thing down my throat but soon it was hitting my gag reflex, so I back up a bit and licked and sucked like a cheap slut! Soon, I was licking Dee's balls and sucking on them. I was still jacking myself off and blew a load all over the floor. Dee then ordered Greg to lick it up and to lick my dick clean. Greg's mouth was hot from his fever but it felt so good. I had Dee's hot, hard black dick in my mouth and Greg's hot mouth on my dick...this was heaven!
After a few more minutes, Dee stopped me and told Greg to stop sucking my dick. Dee was definitely in charge! Dee ordered Greg to go get us some beers and Dee took me to the couch, where he started kissing me and caressing me and undressing me the rest of the way. By this point, I had no idea where my pants or shoes were not nor did I care!
"Whew! I need a cigarette!" Dee exclaimed with a bit of a chuckle. "Damn, I didn't know you were an ass eater! We should've done this years ago!" I laughed and said that I hadn't known I was...but that I was really enjoying it.
Greg brought us our beers and sat demurely on the floor, waiting for Dee's next order. We sat drinking our beers and had a smoke and just chatted a bit. Dee started to fondle my cock, stroking it hard. I tried to kiss him but Dee told me that he had other uses for my mouth. He took my head and lowered it to his still erect cock and told me to start licking it.
I did as told and licked the shaft, slowly up and down. I took the swollen head into my mouth and slowly bobbed up and down on it, as many women had done to mine over the years. My cock was fully erect again. Dee told Greg to stroke me but not to let me cum. When Greg asked if he could suck my dick, Dee flatly told him NO. My dick was now Dee's to use as he saw fit.
Dee was certainly enjoying being in charge and it was turning him on more and more by the minute. He told Greg to stop stroking me and to go get some condoms and lube from the other room. "I need fucked and I think it's time my friend gets to fuck me!" Dee laughed.
This was about to be another first for me! Just a few hours earlier, I'd never kissed a man or eaten anyone's ass. I'd never sucked a dick before. Now, I'd done all of those and was about to fuck a man. Part of my mind was confused but whatever part of the brain that controls our actions was pushing me to fuck Dee's ass!
Greg returned with the condoms and lube. Dee told me to lick his ass and get it good and wet. I promptly buried my face back in my friend's perfect black ass and got it as wet as possible. Greg was unrolling a condom onto my hard dick. As I pulled my face out of Dee's ass, I could feel my own saliva all over my mouth and cheeks...but I didn't care.
Greg applied a good amount of lube to Dee's ass and I was instructed to fuck him like a whore. I normally like to start fucking slow and easy but Dee wanted it hard and fast, so I jammed my cock as deep into his ass as I could and thrust it in and out repeatedly. "Oh Yes! Fuck my pussy!" Dee yelled at me! "Fuck me hard! Fuck me like the bitch I am!" I fucked faster and harder...I was fucking so hard that I almost pulled the condom off. I stopped briefly to pull it back on and resumed fucking. CLICK! The flash of Greg's camera went off. CLICK CLICK CLICK Greg was catching the entire act on film. That seemed to arouse both Dee and me even more. We were fucking like animals. Dee just kept yelling for me to fuck him harder and faster and I just grunted and groaned with each continuing thrust. Finally, I could feel my cum welling up and I knew I was about to blow. "I'm CUMMIIIIING!!!!!!!!" I yelled and Dee thrust his ass as far onto my dick as he could. I shot load after load while Dee humped his ass against my cock. We collapsed onto each other in a heap on the floor.
"Can I?" Greg asked Dee.
"But of course darling" Dee answered as Greg took off my condom, licked my cock clean, then sucked every last drop of my cum out of the condom. This shocked me a bit but I figured there was still a lot for me to learn.
I stayed the entire weekend. My face seemed buried in Dee's ass half the time and the other half I was sucking Dee, he was sucking me, or Greg was sucking one of us or both of us. Dee told me I was the best ass eater he'd ever known and strongly suggested that I come visit more often. With an offer that good, who could refuse?
The End
Did you enjoy this story? Please feel free to send comments to: kingotbass@yahoo.com
I hope you'll enjoy these other stories I've posted on Nifty.org:
How All of This Got Started We All Make Mistakes Sometime Mistaken Identity Wrong Place, Right Time Wrong Place, Right Time Part 2: Curtis & I Find Out Why It's Called "The Pokey"